As filed with the Securities and Exchange Commission on August 20, 2004. May 5, 2006.
Registration No. 333-______ ================================================================================ 333-130897
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549
AMENDMENT NO. 2
to
FORM S-4
REGISTRATION STATEMENT
UNDER THE SECURITIES ACT OF 1933
WINTRUST FINANCIAL CORPORATION (Exact
(Exact Name of Registrant as Specified in its Charter)
ILLINOIS
Illinois602236-3873352 (State
(State or Other Jurisdiction of (Primary(Primary Standard Industrial (I.R.S.(I.R.S. Employer
Incorporation or Organization)Classification Code Number)Identification Number)
727 NORTH BANK LANE LAKE FOREST, ILLINOISNorth Bank Lane
Lake Forest, Illinois 60045-1951
(847) 615-4096 (Address,

(Address, including zip code, and telephone number, including area code, of Registrant'sRegistrant’s principal executive offices) DAVID
David A. DYKSTRA SENIOR EXECUTIVE VICE PRESIDENT AND CHIEF OPERATING OFFICER Dykstra
Senior Executive Vice President and Chief Operating Officer
727 NORTH BANK LANE LAKE FOREST, ILLINOISNorth Bank Lane
Lake Forest, Illinois 60045-1951
(847) 615-4096 (Name,

(Name, address, including zip code, and telephone number, including area code, of agent for service) COPIES TO: JOHN R. OBIALA, ESQ. BENJAMIN G. LOMBARD, ESQ. JENNIFER DURHAM KING, ESQ. REINHART BOERNER VAN DEUREN S.C. VEDDER, PRICE, KAUFMAN & KAMMHOLZ, P.C. 1000 NORTH WATER STREET, SUITE 2100 222 NORTH LASALLE STREET, SUITE 2600 MILWAUKEE, WISCONSIN 53202 CHICAGO, ILLINOIS 60601 (414) 298-1000 (312) 609-7500 ______________________________
Copies to:
Lisa J. Reategui
Sidley Austin LLP
One South Dearborn Street
Chicago, Illinois 60603
(312) 853-7000
Edwin S. del Hierro
Barack Ferrazzano Kirschbaum
Perlman & Nagelberg LLP
333 West Wacker Drive, Suite 2700
Chicago, Illinois 60606
(312) 984-3100
     APPROXIMATE DATE OF COMMENCEMENT OF PROPOSED SALE TO THE PUBLIC: As soon as practicable after the Registration Statement becomes effective. ______________________________effective and after the conditions to the completion of the proposed transaction described in the proxy statement/prospectus have been satisfied or waived.
     If the securities being registered on this Form are being offered in connection with the formation of a holding company and there is compliance with General Instruction G, check the following box. [ ]o
     If this Form is filed to register additional securities for an offering pursuant to Rule 462(b) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. [ ]o
     If this Form is a post-effective amendment filed pursuant to Rule 462(d) under the Securities Act, check the following box and list the Securities Act registration statement number of the earlier effective registration statement for the same offering. [ ] ______________________________ CALCULATION OF REGISTRATION FEE
- ----------------------------------------------------------------------------------------------------------------------- PROPOSED MAXIMUM PROPOSED MAXIMUM TITLE OF EACH CLASS OF AMOUNT OFFERING PRICE AGGREGATE AMOUNT OF SECURITIES TO BE REGISTERED TO BE REGISTERED PER SHARE(1) OFFERING PRICE(2) REGISTRATION FEE(2) - ----------------------------------------------------------------------------------------------------------------------- Common stock, without par value* 583,000 $61.18 $1,044,755 $132.37 - ----------------------------------------------------------------------------------------------------------------------- * Including the preferred share purchase rights associated therewith. (1) Estimated solely for the purpose of determining the registration fee pursuant to Rule 457(f)(2), based on the book value of the shares of Town Bankshares, Ltd. common stock computed as of June 30, 2004. (2) Estimated solely for the purpose of determining the registration fee pursuant to Rule 457(f)(3).
______________________________ THE REGISTRANT HEREBY AMENDS THIS REGISTRATION STATEMENT ON SUCH DATE OR DATES AS MAY BE NECESSARY TO DELAY ITS EFFECTIVE DATE UNTIL THE REGISTRANT SHALL FILE A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS REGISTRATION STATEMENT SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE WITH SECTIONo
The registrant hereby amends this registration statement on such date or dates as may be necessary to delay its effective date until the registrant shall file a further amendment which specifically states that this registration statement shall thereafter become effective in accordance withSection 8(a) OF THE SECURITIES ACT OF of the Securities Act of 1933, AS AMENDED, OR UNTIL THE REGISTRATION STATEMENT SHALL BECOME EFFECTIVE ON SUCH DATE AS THE COMMISSION, ACTING PURSUANT TO SAID SECTIONas amended, or until the registration statement shall become effective on such date as the Commission, acting pursuant to said Section 8(a), MAY DETERMINE. may determine.


The information in this proxy statement/prospectus is not complete and may be changed. We may not offer or sell these securities until the registration statement filed with the Securities and Exchange Commission is effective. This preliminary proxy statement/prospectus is not an offer to sell these securities and it is not soliciting an offer to buy these securities in any statejurisdiction where the offer or sale is not permitted.

PRELIMINARY COPY — SUBJECT TO COMPLETION, DATED AUGUST 20, 2004 [TOWN BANKSHARES LOGO] WINTRUST FINANCIAL CORPORATION ________________ MAY 4, 2006
(HINSBROOK LOGO)Wintrust Financial Corporation
PROXY STATEMENT OF TOWN BANKSHARES, LTD. ________________ HINSBROOK BANCSHARES, INC.
PROSPECTUS OF WINTRUST FINANCIAL CORPORATION ________________ MERGER PROPOSED - YOUR VOTE IS VERY IMPORTANT
Merger Proposal – Your Vote Is Important
DEAR TOWN BANKSHARES, LTD.HINSBROOK SHAREHOLDERS:
     You are cordially invited to attend a special meeting of shareholders of Town Bankshares, Ltd.Hinsbrook Bancshares, Inc. which will be held on __________ __, 2004,May 30, 2006, at _____ p.m.4:00 p.m, local time, at _____________________.the main office of Hinsbrook Bank & Trust located at 6262 South Route 83, Willowbrook, Illinois 60527
     At the meeting, you will be asked to approve a merger agreement between Town BanksharesHinsbrook and Wintrust Financial Corporation that provides for Wintrust'sWintrust’s acquisition of Town Bankshares. IfHinsbrook through the merger is completed,of Hinsbrook with and into Wintrust. You may elect to convert each share of Town BanksharesHinsbrook common stock which you own will be converted into cash, shares of Wintrust’s common stock, or a combination of cash and shares of Wintrust common stock.All elections for cash consideration, stock consideration or the rightcombination of cash and stock consideration are subject to proration as described in this proxy statement/prospectus.Subject to possible proration, if you elect to receive all cash consideration, you will receive $41.59 per share in cash. Subject to possible proration, if you elect to receive the merger consideration in all shares of Wintrust'sWintrust common stock, plus cashyou will receive between 0.680 and 0.846 of a share of Wintrust common stock, depending on the average high and low sale price of Wintrust common stock on the Nasdaq National Market during the 10 trading day period ending on the fourth trading day prior to completion of the merger. Assuming that the price of Wintrust common stock on the Nasdaq National Market is between $49.14 and $61.14 per share, the value of the consideration paid in the amount of $58.10. The exact number of shares of Wintrust common stock that you will receive will depend uponin the average pricemerger for each share of WintrustHinsbrook common stock determinedwill be approximately $41.59 at the time the exchange ratio is calculated. The formula for determining the appropriate exchange ratio for each share of closing. If the average price determined at closing of Wintrust'sHinsbrook common stock is at least $41.34 per shareset forth in detail in this proxy statement/prospectus. If you elect to receive merger consideration consisting of cash and no more than $55.34 per share, you would receive a number of shares of Wintrust common stock, equal to $71.00 divided byyou will receive cash consideration for one-half of your Hinsbrook shares and stock consideration for the average price and $58.10 in cash for each shareother half of Town Bankshares common stock whichyour Hinsbrook shares.
The exchange ratio will not be determined until after the date of the special meeting. Therefore, at the time of the special meeting, you own andwill not know the precise value of the total per sharestock merger consideration you may receive on the date the merger is completed.We estimate that you would receive would be $129.10. If the average price of the Wintrust common stock is less than or equalmay issue up to $41.34, you will receive 1.717 shares of common stock and $58.10 in cash for each share of Town Bankshares common stock you own, and if the average price of the Wintrust common stock is greater than $55.34, you will receive 1.2831,500,000 shares of Wintrust common stock and $58.10 in cash for each share of Town Bankshares common stock you own. Subject to certain conditions, Wintrust may terminateHinsbrook shareholders as contemplated by the merger agreement if the average price of its common stock is greater than $58.34, and Town Bankshares may terminate the merger agreement if the average price of Wintrust's common stock is less than $38.34. Wintrust'sagreement.
     Wintrust’s common stock is traded on the Nasdaq National Market under the symbol "WTFC."“WTFC.” The closing price of Wintrust common stock on ______________ __, 2004,May 3, 2006, was $______.$51.05.
     The merger cannot be completed unless the holders of at least a majority of the voting power of the outstanding shares of Town BanksharesHinsbrook common stock vote in favor of the merger agreement. YOUR BOARD OF DIRECTORS HAS UNANIMOUSLY APPROVED THE MERGER AGREEMENT AND RECOMMENDS THAT YOU APPROVE IT.Your board of directors has unanimously approved the merger agreement and recommends that you vote “FOR” the approval of the merger agreement at the special meeting. Your board of directors also unanimously recommends that you vote “FOR” the approval to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to approve the merger agreement and the transactions it contemplates and “FOR” the authorization of the proxies named in the proxy card to vote on such other matters as may properly come before the special meeting or any adjournment or postponement thereof.
     Additional information regarding the transaction, the merger agreement, Town BanksharesHinsbrook and Wintrust is set forth in the attached proxy statement/prospectus. This document also serves as the prospectus for up to 583,0001,500,000 shares of Wintrust common stock that may be issued by Wintrust in connection with the merger.We urge you to read this entire document carefully, including "Risk Factors"“Risk Factors” beginning on page 15. 17.
Sincerely, William J. Hickmann Chairman
Robert K. Buhrke
President and Chief Executive Officer
Hinsbrook Bancshares, Inc.
Neither the Securities and Exchange Commission nor any state securities regulatory body has approved or disapproved of the Boardsecurities to be issued under this proxy statement/prospectus or determined if this proxy statement/prospectus is accurate or adequate. Any representation to the contrary is a criminal offense.
The securities to be issued in connection with the merger are not savings or deposit accounts or other obligations of Directors Town Bankshares, Ltd. NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES REGULATORY BODY HAS APPROVED OR DISAPPROVED OF THE SECURITIESany bank or nonbank subsidiary of any of the parties, and they are not insured by the Federal Deposit Insurance Corporation, the Bank Insurance Fund or any other governmental agency.
This proxy statement/prospectus is dated ___, 2006, and is first being mailed to Hinsbrook shareholders on or about ___, 2006.


REFERENCES TO BE ISSUED UNDER THIS PROXY STATEMENT/PROSPECTUS OR DETERMINED IF THIS PROXY STATEMENT/PROSPECTUS IS TRUTHFUL OR COMPLETE. ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL OFFENSE. THE SECURITIES TO BE ISSUED IN CONNECTION WITH THE MERGER ARE NOT SAVINGS OR DEPOSIT ACCOUNTS OR OTHER OBLIGATIONS OF ANY BANK OR NONBANK SUBSIDIARY OF ANY OF THE PARTIES, AND THEY ARE NOT INSURED BY THE FEDERAL DEPOSIT INSURANCE CORPORATION, THE BANK INSURANCE FUND OR ANY OTHER GOVERNMENTAL AGENCY. THIS PROXY STATEMENT/PROSPECTUS IS DATED ___________ __, 2004, AND IS FIRST BEING MAILED TO TOWN BANKSHARES SHAREHOLDERS ON OR ABOUT ___________ __, 2004. AVAILABLEADDITIONAL INFORMATION
     As permitted by the rules of the Securities and Exchange Commission, this documentproxy statement/prospectus incorporates certain important business and financial information about Wintrust from other documents that are not included in or delivered with this document.proxy statement/prospectus. These documents are available to you without charge upon your written or oral request. Your requests forYou can obtain documents incorporated by reference in this proxy statement/prospectus through the Securities and Exchange Commission’s website atwww.sec.gov or by requesting them in writing or by telephone at the following address and telephone number:
Wintrust Financial Corporation
727 North Bank Lane
Lake Forest, Illinois 60045-1951
Attention: David A. Dykstra
Senior Executive Vice President and Chief Operating Officer
(847) 615-4096
In order to ensure timely delivery of these documents, you should be directedmake your request by May 12, 2006 to receive them before the following: WINTRUST FINANCIAL CORPORATION 727 NORTH BANK LANE LAKE FOREST, ILLINOIS 60045 ATTENTION: DAVID A. DYKSTRA CHIEF OPERATING OFFICER (847) 615-4096 IN ORDER TO ENSURE TIMELY DELIVERY OF THESE DOCUMENTS, YOU SHOULD MAKE YOUR REQUESTspecial meeting.
See “Where You Can Find More Information” beginning on page 61.
VOTING BY ___________ __, 2004 TO RECEIVE THEM BEFORE THE SPECIAL MEETING. YOU CAN ALSO OBTAIN DOCUMENTS INCORPORATED BY REFERENCE IN THIS DOCUMENT THROUGH THE SEC'S WEBSITE AT WWW.SEC.GOV. SEE "WHERE YOU CAN FIND MORE INFORMATION" BEGINNING ON PAGE 54. TOWN BANKSHARES, LTD. 400 Genesse Street Delafield, Wisconsin 53018 ___________________________________ MAIL
     Hinsbrook shareholders of record may submit their proxies by mail, by signing and dating each proxy card you receive, indicating your voting preference on each proposal and returning each proxy card in the prepaid envelope which accompanied that proxy card.


HINSBROOK BANCSHARES, INC.
6262 South Route 83
Willowbrook, Illinois 60527
Notice of Special Meeting of Shareholders to be held ___________ __, 2004 ___________________________________ DATE: TIME: PLACE: To Town Bankshares, Ltd. Shareholders: We are pleased to notify you of and invite you to
Date:
May 30, 2006
Time:
4:00 p.m., local time
Place: Main office of Hinsbrook Bank & Trust located at 6262 South Route 83, Willowbrook, Illinois 60527
TO HINSBROOK BANCSHARES, INC. SHAREHOLDERS:
     NOTICE IS HEREBY GIVEN that Hinsbrook Bancshares, Inc. will hold a special meeting of shareholders. Atshareholders on May 30, 2006 at 4:00 p.m., local time, at the main office of Hinsbrook Bank & Trust located at 6262 South Route 83, Willowbrook, Illinois 60527. The purpose of the meeting you will be askedis to consider and vote on the following matters: o Approval of the Agreement and Plan of Merger, dated as of June 14, 2004, that provides for Wintrust Financial Corporation to acquire Town Bankshares, Ltd., as described in the attached proxy statement/prospectus. o To transact any other business that properly comes before the special meeting, or any adjournments or postponements of the special meeting.
A proposal to approve the Agreement and Plan of Merger, dated as of December 5, 2005 by and between Wintrust Financial Corporation and Hinsbrook Bancshares, Inc. A copy of the merger agreement is included asAnnex Ato the proxy statement/prospectus accompanying this notice.
The approval to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to approve the merger agreement and the transactions it contemplates.
To transact any other business that properly comes before the special meeting, or any adjournments or postponements thereof.
Holders of record of Town BanksharesHinsbrook common stock at the close of business on ___________ __, 2004 mayApril 24, 2006 are entitled to receive this notice and to vote at the special meeting.meeting and any adjournments or postponements thereof. Approval of the merger agreement requires the affirmative vote at the special meeting of holders of at least a majority of the voting power of the outstanding shares of Town BanksharesHinsbrook common stock. THE BOARD OF DIRECTORS OF TOWN BANKSHARES UNANIMOUSLY RECOMMENDS THAT YOU VOTE "FOR" APPROVAL OF THE MERGER AGREEMENT. Town Banksharesstock entitled to vote.
The board of directors of Hinsbrook unanimously recommends that you vote “FOR” approval of the merger agreement. Your board of directors also unanimously recommends that you vote “FOR” approval to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to approve the merger agreement and the transactions it contemplates and “FOR” the authorization of the proxies named in the proxy card to vote on such other matters as may properly come before the special meeting or any adjournment or postponement thereof.
Hinsbrook shareholders may dissent from the merger and, upon complying with the requirements of WisconsinIllinois law, receive cash equal to the fair value of their shares instead of the merger consideration. See "Special“Information about the special meeting of Town Bankshares shareholders--Dissenters' rights"Hinsbrook shareholders—Dissenters’ rights” in the accompanying proxy statement/prospectus for additional information.
Your vote is important. To ensure that your shares are voted at the special meeting, please promptly complete, sign and return the proxy form in the enclosed prepaid envelope whether or not you plan to attend the meeting in person. Shareholders who attend the special meeting may revoke their proxies and vote in person, if they so desire. Delafield, Wisconsin ___________ __, 2004 To make a timely election of merger consideration, please complete, sign and return the election form in the enclosed prepaid envelope. To be considered timely, election forms must be received by 5:00 p.m., Chicago time, on the fifth business day before the effective time of the merger.
Willowbrook, Illinois
May 4, 2006
By Order of the Board of Directors William J. Hickmann Chairman of the Board of Directors
Robert K. Buhrke
President and Chief Executive Officer


TABLE OF CONTENTS
PAGE QUESTIONS AND ANSWERS ABOUT THE MERGER........................................1 SUMMARY .....................................................................4 Information about Wintrust and Town Bankshares.......................4 The merger and the merger agreement..................................4 Reasons for the merger...............................................4 Board recommendation to Town Bankshares' shareholders................5 Fairness opinion of Town Bankshares' Financial Advisor...............6 Town Bankshares special meeting......................................6 Record date for the special meeting; revocability of proxies.........6 Vote required........................................................6 Voting by participants in the ESOP...................................6 What Town Bankshares shareholders will receive.......................6 Cash redemption of the Town Bankshares common stock in the ESOP......7 Regulatory approvals.................................................7 New Wintrust shares will be eligible for trading on Nasdaq...........8 Conditions to the merger.............................................8 Termination..........................................................8 Termination fee......................................................8 Interests of officers and directors in the merger that are different from yours.....................................9 Voting agreement.....................................................9 Accounting treatment of the merger...................................9 Certain differences in shareholder rights............................9 Dissenters' rights...................................................9 Tax consequences of the merger.......................................9 Historical Comparative Per Share Data; Pro Forma Per Share Data.....10 Selected Financial Data of Wintrust.................................12 RISK FACTORS.................................................................15 There is fluctuation in the trading market of Wintrust's common stock and the market price of the common stock you will receive in the merger is uncertain....................15 Town Bankshares' shareholders will not control Wintrust's future operations..........................................15 De novo operations and branch openings impact Wintrust's profitability..............................................15 Wintrust's allowance for loan losses may prove to be insufficient to absorb losses that may occur in its loan portfolio.............................................16 Wintrust's premium finance business involves unique operational risks and could expose it to significant losses............16 Wintrust may be adversely affected by interest rate changes.........17 Wintrust's shareholder rights plan and provisions in its articles of incorporation and by-laws may delay or prevent an acquisition of Wintrust by a third party........17 CAUTION ABOUT FORWARD-LOOKING STATEMENTS.....................................17 SPECIAL MEETING OF TOWN BANKSHARES SHAREHOLDERS..............................19 Date, place, time and purpose.......................................19 Record date, voting rights, quorum and required vote................19 Voting and revocability of proxies..................................19 Voting rights of participants in the ESOP...........................19 Dissenters' rights..................................................21 i TABLE OF CONTENTS (continued) PAGE DESCRIPTION OF THE MERGER....................................................23 General ...........................................................23 The Companies.......................................................23 Background of the merger............................................24 Wintrust's reasons for the merger...................................27 Town Bankshares' reasons for the merger and recommendation of the board of directors.........................27 Fairness Opinion of Town Bankshares' Financial Advisor..............29 Accounting treatment................................................32 Tax consequences of the merger......................................32 Regulatory approvals................................................34 Interests of certain persons in the merger..........................34 Voting agreement....................................................36 Restrictions on resale of Wintrust common stock.....................36 DESCRIPTION OF THE MERGER AGREEMENT..........................................37 Time of completion..................................................37 Consideration to be received in the merger..........................37 Exchange of certificates............................................38 Conduct of business pending the merger and certain covenants........39 Representations and warranties......................................40 Conditions to completion of the merger..............................41 Minimum net worth and loan loss reserve requirements closing condition................................................43 Termination.........................................................43 Termination fee.....................................................43 Management of Wintrust and Town Bank after the merger...............44 Employee benefit matters............................................44 Termination of ESOP and redemption of ESOP shares...................44 Expenses............................................................45 Nasdaq stock listing................................................45 COMPARISON OF SHAREHOLDER RIGHTS.............................................45 Authorized capital stock............................................46 Payment of dividends................................................46 Advance notice requirements for presentation of business and nominations of directors at annual meetings of shareholders..................................46 Quorum ...........................................................47 Election, classification and size of Board of Directors.............47 Removal of directors................................................47 Filling vacancies on the Board of Directors.........................47 Amendment of Articles of Incorporation and By-laws..................47 Mergers, acquisitions and other transactions........................48 Business combinations with interested shareholders..................48 Limitations on directors' liability.................................49 Indemnification.....................................................50 Action by shareholders without a meeting............................51 Special meetings of shareholders....................................51 Preemptive rights...................................................52 Dissenters' rights..................................................52 Certain anti-takeover effects of Wintrust's articles and by-laws and Illinois law.....................................52 Rights plan.........................................................53 ii TABLE OF CONTENTS (continued) PAGE LEGAL MATTERS................................................................53 EXPERTS ....................................................................54 SHAREHOLDER PROPOSALS........................................................54 WHERE YOU CAN FIND MORE INFORMATION..........................................54 INCORPORATION OF CERTAIN INFORMATION BY REFERENCE............................54 ANNEX A: AGREEMENT AND PLAN OF MERGER......................................A-1 ANNEX B: WISCONSIN DISSENTERS' RIGHTS LAW..................................B-1 ANNEX C: VOTING AGREEMENT..................................................C-1 ANNEX D: FAIRNESS OPINION OF TOWN BANKSHARES' FINANCIAL ADVISOR............D-1
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QUESTIONS AND ANSWERS ABOUT THE MERGER Q: WHAT AM I BEING ASKED TO VOTE ON? WHAT IS THE PROPOSED TRANSACTION? A: You are being asked to vote on the approval of a merger agreement that provides for Wintrust's acquisition of Town Bankshares. Wintrust will own all of Town Bankshares' outstanding common stock after
Q:What am I being asked to vote on? What is the proposed transaction?
A:You are being asked to vote on the approval of a merger agreement that provides for Wintrust’s acquisition of Hinsbrook through the merger of Hinsbrook with and into Wintrust. If you elect to receive shares of Wintrust common stock in exchange for half or all of your Hinsbrook shares or, if as a result of the proration procedures described in this proxy statement/prospectus, your cash election is prorated to include shares of Wintrust common stock, you will become a shareholder of Wintrust as a result of the merger.
Q:What will Hinsbrook shareholders be entitled to receive in the merger?
A:If the merger is completed, the shares of Hinsbrook common stock that you own immediately before the completion of the merger will be converted into the right to receive cash, shares of Wintrust common stock, or a combination of 50% cash and 50% shares of Wintrust common stock (in each case subject to possible proration). For each of your shares of Hinsbrook common stock, you will receive the “per share merger consideration” to be calculated as set forth in the merger agreement. All elections for cash consideration, stock consideration or the combination of cash and stock consideration are subject to proration as described in this proxy statement/prospectus. For example, if you elect to receive all cash consideration, depending on the elections made by other Hinsbrook shareholders, it is possible that you will receive a portion of the merger consideration in cash and a portion in stock. The same might be true if you elect to receive all stock consideration. For a description of the possible proration of elections, see “Description of the merger agreement – Consideration to be received in the merger – Proration of merger consideration.”
You may elect to receive the “per share merger consideration” in cash, shares of Wintrust’s common stock, or a combination of cash and shares of Wintrust common. Subject to possible proration, if you elect to receive all cash consideration, you will receive $41.59 per share in cash. Subject to possible proration, if you elect to receive the merger consideration in all shares of Wintrust common stock, you will receive between 0.680 and 0.846 of a share of Wintrust common stock for each share of Hinsbrook common stock, depending on the average high and low sale price of Wintrust common stock on the Nasdaq National Market during the 10 trading day period ending on the fourth trading day prior to completion of the merger. If you elect to receive merger consideration consisting of cash and shares of Wintrust common stock, you will receive merger consideration consisting of cash consideration of $41.59 for one-half of your Hinsbrook shares and the above-described stock consideration for the other half of your Hinsbrook shares.
In this proxy statement/prospectus, we refer to the fraction of a share of Wintrust common stock to be issued for each share of Hinsbrook common stock subject to the stock election or the combination election as the “exchange ratio” and we refer to the average high and low sale price of Wintrust common stock on the Nasdaq National Market during the 10 trading day period ending on the fourth trading day prior to completion of the merger (which we refer to as the “reference period”) as the “reference price.” The merger agreement provides that:
The exchange ratio will adjust upward or downward to ensure that the fraction of a share of Wintrust common stock you receive for each share of Hinsbrook common stock that you own will be equal to $41.59 divided by the reference price so long as the reference price is between $49.14 and $61.14. However, the market value of the fraction of a share of Wintrust common stock that you receive in the merger may be greater or less than $41.59, as the trading price of Wintrust common stock on the date the merger is completed may be greater or less than the reference price used to determine the exchange ratio.
If the reference price is less than $49.14, the exchange ratio will no longer adjust upward, and you will receive 0.846 of a share of Wintrust common stock for each share of Hinsbrook common stock that you own. This means that the value of the fraction of a share of Wintrust common stock you will receive will be below $41.59 per share to the extent the market price of Wintrust common stock is below $49.14 when the merger is completed.

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If the reference price is greater than $61.14, the exchange ratio will no longer adjust downward, and you will becomereceive 0.680 of a shareholdershare of Wintrust. Q: WHAT WILL I BE ENTITLED TO RECEIVE IN THE MERGER? A: If the merger is completed,Wintrust common stock for each share of Town BanksharesHinsbrook common stock that you own immediately beforeown. This means that the completionvalue of the merger will be converted into the right to receive sharesfraction of Wintrust common stock, plus cash in the amounta share of $58.10. For each of your shares of Town BanksharesWintrust common stock you will receive a number of shares of Wintrust common stock equalwill be above $41.59 per share to the "per share stock consideration" to be calculated as set forth inextent the merger agreement. The per share stock consideration will be determined by dividing $71.00 by the average of the high and low sale prices of Wintrust common stock during the 10-day trading period ending two trading days before the merger closing date, if the average price is at least $41.34 per share but not more than $55.34 per share. If the average price of the Wintrust common stock during this period is less than or equal to $41.34, you will receive 1.717 shares of Wintrust common stock and $58.10 in cash for each share of Town Bankshares common stock you own, and if the average price of the Wintrust common stock is greater than $55.34 per share, you will receive 1.283 shares of Wintrust common stock and $58.10 in cash for each share of Town Bankshares common stock you own. However, subject to certain conditions, Wintrust may terminate the merger agreement if the averagemarket price of Wintrust common stock is greater than $58.34 and Town Bankshares may terminate the merger agreement if the average price of Wintrust common stock is less than $38.34. Town Bank's Employee Stock Ownership Plan, or the ESOP, will not receive shares of Wintrust common stock and cash in the merger in exchange for the shares of Town Bankshares common stock held in the ESOP. Instead, the merger agreement provides that prior to the effective time of the merger, Town Bankshares will terminate the ESOP and redeem each share of Town Bankshares common stock in the ESOP for cash in the amount of $58.10, plus the cash value of the per share stock consideration received by Town Bankshares' shareholders in the merger. However, the termination of the ESOP and redemption of the shares of Town Bankshares common stock in the ESOP will not be effective unlessabove $61.14 when the merger is subsequently completed. Q: WHY DO TOWN BANKSHARES AND WINTRUST WANT TO MERGE? A: Town Bankshares believes that the proposed merger will provide Town Bankshares shareholders with substantial benefits, and Wintrust believes that the merger will further its strategic growth plans. Wintrust does not currently have any banking offices in Wisconsin, and believes the acquisition of Town Bankshares provides an attractive opportunity to expand into southeastern Wisconsin. As a larger company, Wintrust can provide the capital and resources that Town Bank needs to compete more effectively and to offer a broader array of products and services to better serve its banking customers. To review the reasons for the merger in more detail, see "Description of the merger--Wintrust's reasons for the merger" on page 27 and "Description of the merger--Town Bankshares' reasons for the merger and recommendation of the board of directors" on page 27. Q: WHAT DOES THE TOWN BANKSHARES BOARD OF DIRECTORS RECOMMEND? A: Town Bankshares' board of directors unanimously recommends that you vote "FOR" adoption of the merger agreement. Town Bankshares' board of directors has determined that the merger agreement and the merger are in the best interests of Town Bankshares and its shareholders. To review the background and reasons for the merger in greater detail, see pages 24 to 29. 1 Q: WHAT VOTE IS REQUIRED TO ADOPT THE MERGER AGREEMENT? A: Holders of at least a majority of the voting power of the outstanding shares of Town Bankshares common stock must vote in favor of the merger. All of Town Bankshares' directors and executive officers have agreed to vote their shares in favor of the merger at the special meeting. These shareholders owned approximately 16.9% of Town Bankshares' outstanding common stock on the record date. Wintrust shareholders will not be voting on the merger agreement. See "Description of the merger--Interests of certain persons in the merger" on page 34 and "Description of the merger--Voting agreement" on page 36. Q: WHAT DO I NEED TO DO NOW? HOW DO I VOTE? A: After you have carefully read and considered the information contained in this proxy statement/prospectus, please complete, sign, date and mail your proxy form in the enclosed return envelope as soon as possible. This will enable your shares to be represented at the special meeting. You may also vote in person at the meeting. If you do not return a properly executed proxy form and do not vote at the special meeting, this will have the same effect as a vote against the approval of the merger agreement. If you sign, date and send in your proxy form, but you do not indicate how you want to vote, your proxy will be voted in favor of approval of the merger agreement. You may change your vote or revoke your proxy prior to the special meeting by filing with the secretary of Town Bankshares a duly executed revocation of proxy, submitting a new proxy form with a later date or voting in person at the special meeting. Q: DO PARTICIPANTS IN THE ESOP HAVE ANY VOTING RIGHTS WITH RESPECT TO THE MERGER? A: Yes. If you are a participant in the ESOP and shares of Town Bankshares common stock have been allocated to your account under the ESOP as of _________, the record date for the special meeting, you will receive with this proxy statement/prospectus a "Direction to ESOP Administrator" form. This form will direct the ESOP's trustees to vote the shares allocated to your account in accordance with the instructions that accompany the form. You should return this form to the ESOP's trustees as indicated in the instructions that accompany the form. Shares of Town Bankshares common stock which are not yet allocated to participant accounts under the ESOP will be voted as directed by the ESOP's administrator. Q: WHAT IF I OPPOSE THE MERGER? DO I HAVE DISSENTER'S RIGHTS? A: Town Bankshares shareholders who do not vote in favor of the merger agreement and otherwise comply with all of the procedures of Sections 180.1301 through 180.1331 of the Wisconsin Business Corporation Law will be entitled to receive payment in cash of the estimated fair value of their shares of Town Bankshares common stock as ultimately determined under the statutory process. A copy of these provisions is attached as Annex B to this proxy statement/prospectus. This value could be more but could also be less than the merger consideration. Q: WHAT ARE THE TAX CONSEQUENCES OF THE MERGER TO ME? A: It is a condition to the closing of the merger that Town Bankshares' legal counsel render an opinion to Town Bankshares that the merger will constitute a reorganization under Section 368(a) of the Internal Revenue Code. If the merger constitutes a reorganization, the conversion of your shares of Town Bankshares common stock into Wintrust common stock may permit you to defer a portion of your "realized gain" in the exchange. For United States federal income tax purposes, your "realized gain" will be equal to the aggregate consideration (both stock and cash) you receive in the reorganization less your basis in your Town Bankshares' stock exchanged. The portion of your "realized gain" which must be "recognized" will be equal to the lesser of the cash received (excluding cash received in lieu of fractional shares) or the realized gain as a result of the merger (adjusted for any gain recognized for cash received in lieu of fractional shares). In general, the tax basis in your shares of Town Bankshares common stock will carry over to the shares of Wintrust common stock you receive in the merger. The tax basis of the Wintrust common stock you receive in the merger will equal the tax basis in your Town Bankshares common stock exchanged for the merger consideration, decreased by the amount of any cash received (other than cash received in lieu of fractional shares of Town Bankshares common stock) and increased by the amount of any cash received which was treated as a dividend and the amount of any gain recognized in the exchange.
Subject to certain conditions, Hinsbrook may terminate the merger agreement if the reference price of Wintrust’s common stock during the reference period is less than $47.14.
Q:What will Hinsbrook option holders be entitled to receive in the merger?
A:If the merger is completed, each outstanding and unexercised option to purchase Hinsbrook common stock will automatically be converted into an option to purchase shares of Wintrust common stock, exercisable on generally the same terms and conditions that applied before the merger. The number of shares of Wintrust common stock subject to the substitute Wintrust option will equal the number of shares of Hinsbrook common stock subject to the option immediately prior to the merger, multiplied by the “option exchange ratio,” rounded down to the nearest whole share. The per share exercise price of each substitute Wintrust option will equal the exercise price of the option immediately prior to the merger divided by the option exchange ratio, rounded down to the nearest whole cent. The “option exchange ratio” is equal to 41.59 divided by the reference price.
Q:How do I make an election for the merger consideration?
A:You have been provided with an election form to select whether you desire to receive merger consideration of cash, Wintrust common stock or a combination of cash and Wintrust common stock. The election form is separate from the proxy form and should be returned to Illinois Stock Transfer Company in the enclosed prepaid return envelope. Depending on the results of all shareholders’ elections, the amount of stock or cash you receive may be prorated under certain circumstances. The completed election form must be received by Wintrust’s exchange agent, Illinois Stock Transfer Company, on or before the fifth business day before the effective time of the merger. Do not send in your stock certificates with your stock election form.
Q:What if I fail to make an election specifying how I desire to receive the merger consideration?
A:If you do not submit a properly completed election form by the fifth business day before the effective time of the merger, you will be deemed to have elected to receive the merger consideration in a combination of cash consideration for 50% of your Hinsbrook shares and Wintrust common stock consideration for the other 50% of your Hinsbrook shares, subject to proration.
Q:Will I get the form of consideration that I specify on my merger consideration election form?
A:There can be no assurances that you will receive the merger consideration in exactly the form you specify on your election form. The merger agreement provides that all elections for cash consideration, stock consideration or the combination of cash and stock consideration are subject to proration so that the actual number of shares of Hinsbrook common stock that may be converted into the right to receive cash consideration, in the aggregate, may not exceed 50% of Hinsbrook’s outstanding common stock and the number of shares that may be converted into the right to receive stock consideration (including any shares subject to the stock portions of a combination election), in the aggregate, may not exceed 50% of Hinsbrook’s outstanding common stock. As a result, if you elect to receive all cash consideration, depending on the elections made by other Hinsbrook shareholders, it is possible that you will receive a portion of the merger consideration in cash and a portion in stock. The same might be true if you elect to receive all stock consideration. For a description of the possible proration of elections, see “Description of the merger agreement – Consideration to be received in the merger – Proration of merger consideration.”

2 The gain recognized as a result of cash received in lieu of a fractional share will be equal to the excess of such cash over the tax basis attributable to the share or shares of Town Bankshares common stock exchanged therefor. The holding period of your Wintrust common stock received in the merger will include the period during which you held Town Bankshares common stock, provided that the Town Bankshares common stock surrendered was held as a capital asset as of the time of the merger. You should consult your tax adviser for the specific tax consequences of the merger to you. The tax opinion of Town Bankshares' legal counsel will be subject to a number of representations and assumptions summarized under "Description of the merger--Tax consequences of the merger" on page 32. Q: SHOULD I SEND IN MY STOCK CERTIFICATES NOW? A: No. Either at the time of closing or shortly after the merger is completed, Wintrust's exchange agent will send you a letter of transmittal with instructions informing you how to send in your stock certificates to the exchange agent. You should use the letter of transmittal to exchange your Town Bankshares stock certificates for new certificates representing the shares of Wintrust common stock you will own after the merger is complete. DO NOT SEND IN YOUR STOCK CERTIFICATES WITH YOUR PROXY FORM. Q: WHEN IS THE MERGER EXPECTED TO BE COMPLETED? A: We will try to complete the merger as soon as possible. Before that happens, the merger agreement must be approved and adopted by Town Bankshares' shareholders and we must obtain the necessary regulatory approvals. Assuming shareholders vote at least a majority of Town Bankshares' outstanding shares of common stock in favor of the merger agreement and we obtain the other necessary approvals, we expect to complete the merger during the third quarter of 2004. Q: IS COMPLETION OF THE MERGER SUBJECT TO ANY CONDITIONS BESIDES SHAREHOLDER APPROVAL? A: Yes. The transaction must receive the required regulatory approvals, and there are other closing conditions that must be satisfied. For example, as a condition to Wintrust's obligation to close, as of the closing date, Town Bankshares must satisfy certain financial measures set forth in the merger agreement. Q: WHO CAN ANSWER MY OTHER QUESTIONS? A: If you have more questions about the merger or how to submit your proxy, or if you need additional copies of this proxy statement/prospectus or the enclosed proxy form, you should contact Jay C. Mack, Town Bankshares' President and Chief Executive Officer, at (262) 646-6888.


Q:Why do Hinsbrook and Wintrust want to merge?
A:Hinsbrook believes that the proposed merger will provide Hinsbrook shareholders with substantial benefits, and Wintrust believes that the merger will further its strategic growth plans. As a larger company, Wintrust can provide the capital and resources that Hinsbrook Bank & Trust needs to compete more effectively and to offer a broader array of products and services to better serve its banking customers. To review the reasons for the merger in more detail, see “The merger—Wintrust’s reasons for the merger” on page 29 and “The merger—Hinsbrook’s reasons for the merger and recommendation of the board of directors” on page 28.
Q:What does the Hinsbrook board of directors recommend?
A:Hinsbrook’s board of directors unanimously recommends that you vote “FOR” approval of the merger agreement. Hinsbrook’s board of directors has determined that the merger agreement and the merger are in the best interests of Hinsbrook and its shareholders. To review the background and reasons for the merger in greater detail, see pages 26 to 29.
Q:What vote is required to approve the merger agreement?
A:Holders of at least a majority of the voting power of the outstanding shares of Hinsbrook common stock entitled to vote must vote in favor of the merger. Absentations and broker non-votes have the effect of votes against the approval of the merger agreement. On December 5, 2005, all of Hinsbrook’s directors and executive officers, including one executive officer who has since resigned, agreed to vote their shares in favor of the merger at the special meeting. These shareholders and their affiliates owned approximately 39.4% of Hinsbrook’s outstanding common stock on the record date. Wintrust’s shareholders will not be voting on the merger agreement. See “The merger—Interests of certain persons in the merger” on page 39 and “The merger—Voting agreement” on page 41.
Q:Why is my vote important?
A:Hinsbrook shareholders are being asked to approve the merger agreement and thereby approve the proposed merger. If you do not submit your proxy by mail or vote in person at the special meeting, it will be more difficult for Hinsbrook to obtain the necessary quorum to hold the special meeting. In addition, your failure to submit your proxy or attend the special meeting will have the same effect as a vote against the merger agreement and make it more difficult to obtain approval of the merger agreement.
Q:What do I need to do now? How do I vote?
A:You may vote at the special meeting if you own shares of Hinsbrook common stock of record at the close of business on April 24, 2006. After you have carefully read and considered the information contained in this proxy statement/prospectus, please complete, sign, date and mail your proxy form, which is separate from the election form, in the enclosed prepaid return envelope as soon as possible. This will enable your shares to be represented at the special meeting. You may also vote in person at the special meeting. If you do not return a properly executed proxy form and do not vote at the special meeting, this will have the same effect as a vote against the approval of the merger agreement.
Q:How will my proxy be voted?
A:If you complete, sign, date and mail your proxy form, your proxy will be voted in accordance with your instructions. If you sign, date and send in your proxy form, but you do not indicate how you want to vote, your proxy will be votedFOR approval of the merger agreement and the other proposals in the notice.
Q:Can I revoke my proxy and change my vote?
A:You may change your vote or revoke your proxy prior to the special meeting by filing with the secretary of Hinsbrook a duly executed revocation of proxy, submitting a new proxy form with a later date or voting in person at the special meeting.

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Q:What if I oppose the merger? Do I have dissenters’ rights?
A:Hinsbrook shareholders who do not vote in favor of approval of the merger agreement and otherwise comply with all of the procedures of Sections 11.65 and 11.70 of the Illinois Business Corporations Act (the IBCA), will be entitled to receive payment in cash of the fair value of their shares of Hinsbrook common stock as ultimately determined under the statutory process. A copy of these sections of the IBCA is attached asAnnex Bto this document. This value could be more than the merger consideration but could also be less.
Q:What are the tax consequences of the merger to me?
In general, the conversion of your shares of Hinsbrook common stock into Wintrust common stock in the merger will be tax-free for United States federal income tax purposes. However, you will recognize gain (but not loss) in an amount limited to the amount of cash you receive in the merger. Additionally, you will recognize gain or loss on any cash that you receive instead of fractional shares of Wintrust’s common stock.You should consult with your tax adviser for the specific tax consequences of the merger to you.See “The merger – Certain federal income tax consequences of the merger” on page 37.
Q:When and where is the special meeting?
A:The Hinsbrook special meeting will take place on May 30, 2006, at 4:00 p.m. local time, at the main office of Hinsbrook Bank & Trust located at 6262 South Route 83, Willowbrook, Illinois 60527.
Q:Should I send in my stock certificates now?
A:No. Either at the time of closing or shortly after the merger is completed, Wintrust’s exchange agent will send you a letter of transmittal with instructions informing you how to send in your stock certificates to the exchange agent. You should use the letter of transmittal to exchange your Hinsbrook stock certificates for new certificates representing the shares of Wintrust common stock you will own after the merger is complete.Do not send in your stock certificates with your proxy form or your stock election form.
Q:When is the merger expected to be completed?
A:We will try to complete the merger as soon as reasonably possible. Before that happens, the merger agreement must be approved by Hinsbrook’s shareholders and we must obtain the necessary regulatory approvals. Assuming shareholders vote at least a majority of Hinsbrook’s outstanding shares of common stock in favor of the merger agreement and we obtain the other necessary approvals, we expect to complete the merger in the second quarter of 2006.
Q:Is completion of the merger subject to any conditions besides shareholder approval?
A:Yes. The transaction must receive the required regulatory approvals, and there are other closing conditions that must be satisfied. For example, as a condition to Wintrust’s obligation to close, as of the closing date, Hinsbrook must satisfy certain financial measures set forth in the merger agreement.
Q:Are there risks I should consider in deciding to vote on approval of the merger agreement?
A:Yes, in evaluating the merger agreement, you should read this proxy statement/prospectus carefully, including the factors discussed in the section titled “Risk Factors” beginning on page 17.
Q:Who can answer my other questions?
A:If you have more questions about the merger or how to submit your proxy, or if you need additional copies of this proxy statement/prospectus or the enclosed proxy form, you should contact either Robert K. Buhrke, Hinsbrook’s President and Chief Executive Officer, at (630) 920-2700, or Illinois Stock Transfer Company, which is assisting Hinsbrook in the solicitation of proxies, at (312) 427-2951.

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SUMMARY
This summary highlights selected information in this proxy statement/prospectus and may not contain all of the information that is important to you. To understand the merger more fully, you should read this entire documentproxy statement/prospectus carefully, including the annexes and the documents referred to in this proxy statement/prospectus. A listcopy of the documentsmerger agreement is attached as Annex A to this proxy statement/prospectus and is incorporated by reference appearsherein. See “Where You Can Find More Information” beginning on page 54. INFORMATION ABOUT WINTRUST AND TOWN BANKSHARES WINTRUST FINANCIAL CORPORATION (See61.
Information about Wintrust and Hinsbrook(See page 23) 26)
Wintrust Financial Corporation
727 North Bank Lane
Lake Forest, Illinois 60045
(847) 615-4096
     Wintrust Financial Corporation, an Illinois corporation, is a financial holding company headquartered in Lake Forest, Illinois. As of December 31, 2005, Wintrust operates tenoperated 13 community banks, all located in the greater Chicago and Milwaukee metropolitan area,areas, which provide community-oriented, personal and commercial banking services primarily to individuals and small to mid-size businesses through 4262 banking facilities asfacilities. Wintrust, through various of June 30, 2004. Wintrustits subsidiaries, also provides wealth management services, through itsincluding trust, company, investment adviserasset management and broker-dealer subsidiariesbrokerage services, to customers located primarily in the Midwest, as well as to customers of its banks. Wintrust also originates and purchases residential mortgage loans, many of which are sold into the secondary market. In addition, Wintrust is involved in specialty lending through a number of operating subsidiaries or divisions of certain of its banks. As of June 30, 2004,December 31, 2005, Wintrust had consolidated total assets of $5.33$8.17 billion, deposits of $4.32$6.73 billion and shareholders'stockholders’ equity of $374$628 million. Wintrust'sWintrust’s common stock trades on the Nasdaq National Market under the symbol "WTFC." TOWN BANKSHARES, LTD. (See page 23) 400 Genesse Street Delafield, Wisconsin 53018 (262) 646-6888 Town Bankshares, Ltd.“WTFC.”
Hinsbrook Bancshares, Inc.
6262 South Route 83
Willowbrook, Illinois 60527
(630) 920-2700
     Hinsbrook Bancshares, Inc., a Wisconsinan Illinois corporation, is a bank holding company headquartered in Delafield, Wisconsin.Willowbrook, Illinois. Its primary business is operating its bank subsidiary, TownHinsbrook Bank a Wisconsin& Trust, an Illinois state bank, with officesIllinois branch locations in DelafieldWillowbrook, Downers Grove, Darien, Glen Ellyn and Madison, Wisconsin. In addition to TownGeneva. Hinsbrook Bank Town Bankshares conducts limited business activities through Town Investment Corp., a Nevada corporation. We sometimes refer to Town Bank and Town Investment Corp. as the "subsidiaries."& Trust began operations in 1987. As of June 30, 2004, Town BanksharesDecember 31, 2005, Hinsbrook had consolidated total assets of approximately $238.0$500.0 million, deposits of $204.3$430.6 million and shareholders'shareholders’ equity of $17.8$41.4 million. Town BanksharesHinsbrook is not a public company and, accordingly, there is no established trading market for Town Bankshares'Hinsbrook’s common stock. THE MERGER AND THE MERGER AGREEMENT (See
The merger and the merger agreement(See page 37) Wintrust's42)
     Wintrust’s acquisition of Town BanksharesHinsbrook is governed by a merger agreement. The merger agreement provides that, if all of the conditions set forth in the merger agreement are satisfied or waived, Town BanksharesHinsbrook will be merged with and into Wintrust and will cease to exist. After the consummation of the merger, TownHinsbrook Bank & Trust will become a wholly owned subsidiary of Wintrust. The merger agreement is included asAnnex Ato this proxy statement/prospectus and is incorporated by reference herein. We encourageurge you to read the merger agreement carefully and fully, as it is the legal document that governs the merger.
What Hinsbrook shareholders will receive(See page 42)
     If the merger is completed, the shares of Hinsbrook common stock that you own immediately before the completion of the merger will be converted into the right to receive cash, shares of Wintrust common stock, or a combination of cash and shares of Wintrust common stock. For each of your shares of Hinsbrook common stock, you will receive the “per share merger consideration” to be calculated as set forth in the merger agreement. All elections for cash consideration, stock consideration or the combination of cash and stock consideration are subject

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to proration as described in this proxy statement/prospectus. For example, if you elect to receive all cash consideration, depending on the elections made by other Hinsbrook shareholders, it is possible that you will receive a portion of the merger consideration in cash and a portion in stock. The same might be true if you elect to receive all stock consideration. For a description of the possible proration of elections, see “Description of the merger agreement – Consideration to be received in the merger – Proration of merger consideration.”
     You may elect to receive the “per share merger consideration” in cash, shares of Wintrust’s common stock, or a combination of cash and shares of Wintrust common stock. Subject to possible proration, if you elect to receive all cash consideration, you will receive $41.59 per share in cash. Subject to possible proration, if you elect to receive the merger consideration in all shares of Wintrust common stock, you will receive between 0.680 and 0.846 of a share of Wintrust common stock for each share of Hinsbrook common stock, depending on the average high and low sale price of Wintrust common stock on the Nasdaq National Market during the 10 trading day period ending on the fourth trading day prior to completion of the merger. If you elect to receive merger consideration consisting of cash and shares of Wintrust common stock, you will receive cash consideration of $41.59 per share for one-half of your Hinsbrook shares and the above-described stock consideration for the other half of your Hinsbrook shares. The merger agreement provides that:
The exchange ratio will adjust upward or downward to ensure that the fraction of a share of Wintrust common stock you receive for each share of Hinsbrook common stock that you own will be equal to $41.59 divided by the reference price so long as the reference price is between $49.14 and $61.14. However, the market value of the fraction of a share of Wintrust common stock that you receive in the merger may be greater or less than $41.59, as the trading price of Wintrust common stock on the date the merger is completed may be greater or less than the reference price used to determine the exchange ratio.
If the reference price is less than $49.14, the exchange ratio will no longer adjust upward, and you will receive 0.846 of a share of Wintrust common stock for each share of Hinsbrook common stock that you own. This means that the value of the fraction of a share of Wintrust common stock you will receive will be below $41.59 per share to the extent the market price of Wintrust common stock is below $49.14 when the merger is completed.
If the reference price is greater than $61.14, the exchange ratio will no longer adjust downward, and you will receive 0.680 of a share of Wintrust common stock for each share of Hinsbrook common stock that you own. This means that the value of the fraction of a share of Wintrust common stock you will receive will be above $41.59 per share to the extent the market price of Wintrust common stock is above $61.14 when the merger is completed.
     However, subject to certain conditions, Hinsbrook may terminate the merger agreement if the reference price of Wintrust’s common stock during the reference period is less than $47.14.
     Hinsbrook shareholders will not receive fractional shares of Wintrust common stock. Instead, they will receive a cash payment for any fractional shares based on the value of Wintrust common stock determined in the manner described above.
Merger consideration election(See page 44)
     With this proxy statement/prospectus, you have been provided with an election form in order to select whether you will receive merger consideration consisting of cash, Wintrust common stock or a combination of 50% cash and 50% shares of Wintrust common stock (subject to possible proration as described in this proxy statement/prospectus). The completed election form should be returned in the enclosed prepaid envelope and must be received by Wintrust’s exchange agent, Illinois Stock Transfer Company, by 5:00 p.m., Chicago time, on the fifth business day before the effective time of the merger. Once made, elections are irrevocable. If your election form is not received by this deadline, you will be deemed to have elected to receive the combination of cash and Wintrust common stock. Despite your particular election, the merger agreement provides that the aggregate number of shares that may be converted into the right to receive cash consideration (including any shares subject to the cash portion of a combination election) may not exceed 50% of Hinsbrook’s outstanding common stock, and the aggregate number of shares that may be converted into the right to receive Wintrust common stock (including any shares subject to the

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stock portion of a combination election) may not exceed 50% of Hinsbrook’s outstanding common stock. If Hinsbrook’s shareholders elect to receive, in the aggregate, more than the maximum number of shares that may be converted into cash consideration or stock consideration under the merger agreement, Illinois Stock Transfer Company may prorate these elections so that the maximum amount of each type of consideration is not exceeded. For example, if elections to receive all cash consideration are made with respect to 80% of the shares of Hinsbrook’s common stock, Illinois Stock Transfer Company may prorate the elections so that shareholders electing all cash may receive some portion of the merger consideration in cash and some portion in stock. However, taking into account the actual results of the election process, Wintrust may direct, at any time prior to the consummation of the merger, that the proration and redesignation procedures be waived, in whole or in part, so long as such actions do not adversely affect the tax-free reorganization treatment of the merger.
     Once the merger is complete, Illinois Stock Transfer Company will mail you materials and instructions for exchanging your Hinsbrook stock certificates for Wintrust stock certificates. You should not send in your Hinsbrook stock certificates with your completed proxy card or election form, and should wait until you receive the transmittal materials and instructions from the exchange agent.
Hinsbrook Employee Stock Options(See page 44)
     The merger agreement provides that at the effective time of the merger, each outstanding and unexercised option granted by Hinsbrook under its 1992 Employee Stock Option Plan, as amended, will be automatically converted into an option to purchase shares of Wintrust common stock, exercisable on generally the same terms and conditions that applied before the merger. The number of shares of Wintrust common stock subject to the substitute Wintrust option will equal the number of shares of Hinsbrook common stock subject to the option immediately prior to the merger, multiplied by the “option exchange ratio,” rounded down to the nearest whole share. The per share exercise price of each substitute Wintrust option will equal the exercise price of the option immediately prior to the merger divided by the option exchange ratio, rounded down to the nearest whole cent. The “option exchange ratio” is equal to 41.59 divided by the reference price.
Fairness opinion of Hinsbrook’s Financial Advisor(See page 30)
     In deciding to approve the merger, Hinsbrook’s board of directors considered, among other things, the opinion of Capital Market Securities, Inc. that the merger consideration is fair, from a financial point of view, to the holders of Hinsbrook common stock. You should read the full text of the fairness opinion, which is included as Annex Aattached to this proxy statement/prospectus. REASONS FOR THE MERGER (Seeprospectus asAnnex D, to understand the assumptions made, limits of the reviews undertaken and other matters considered by Capital Market Securities, Inc. in rendering its opinion.
Certain federal income tax consequences of the merger(See page 27) Town Bankshares'37)
     Your receipt of shares of Wintrust common stock as part of the merger consideration generally will be tax-free for United States federal income tax purposes. However, you will recognize gain (but not loss) in an amount limited to the amount of cash you receive in the merger. Additionally, you will recognize gain or loss on any cash that you receive instead of fractional shares of Wintrust common stock.You are urged to consult your tax adviser for a full understanding of the federal, state, local and foreign tax consequences of the merger to you.
Reasons for the merger(See page 28)
     Hinsbrook’s board of directors believes that the merger is in the best interests of Town BanksharesHinsbrook and its shareholders, has unanimously approved the merger agreement and unanimously recommends that its shareholders vote "FOR"FOR the approval of the merger agreement.
     In its deliberations and in making its determination, Town Bankshares'Hinsbrook’s board of directors considered numerous factors, including the following: o Wintrust's proposal offered
information with respect to the highest price and more certainty to closing than any other proposal; 4 o the merger consideration of $129.10 per share, payable in cash and shares of Wintrust common stock, as compared to Town Bankshares' net income and book value per share and historical sales prices for shares of Town Bankshares common stock; o the business,businesses, earnings, operations, competitive position, financial condition, operating results, management, objectivesprospects, capital levels and prospectsasset quality of Town Bankshares; o information concerning the business, financial condition, operating resultsHinsbrook and competitive position of Wintrust, including the recent performance of Wintrust common stock; o its belief that the resourcesboth individually and expertise of Wintrust as a larger organization will benefit the customers and employees of Town Bankshares; o Wintrust's commitment to community banking and to maintaining local management and decision-making at its subsidiary banks; o the opinion of Edelman & Co., Ltd. that the merger consideration was fair, from a financial point of view, to Town Bankshares shareholders; o the fact that Wintrust common stock is publicly held and traded on the Nasdaq National Market and would provide greater liquidity than Town Bankshares common stock, which is not publicly traded; o the terms and conditions of the merger agreement, including the floating exchange ratio, the agreement by Town Bankshares not to solicit third-party offers, the termination fee applicable in some circumstances, and the determination of the board of directors that these terms and conditions were appropriate in a strategic transaction of this type; and o the option of Town Bankshares to terminate its obligation to complete the merger if the average trading price per share of Wintrust common stock over a 10-trading day period before the closing of the merger is less than $38.34. Wintrust'scombined company;

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the perceived risks and uncertainties attendant to Hinsbrook’s execution of its strategic growth plans as an independent banking organization, including the need to access additional capital on a cost-effective basis to support future growth;
the belief that the market value of Wintrust’s common stock prior to the execution of the merger agreement was very attractive and offered favorable prospects for future appreciation as a result of the proposed merger and other strategic initiatives being implemented by Wintrust;
the strategic vision of the management of Wintrust to seek profitable future expansion in the Chicago metropolitan area, leading to continued growth in overall shareholder value;
the fact that Wintrust is publicly held and the merger would provide access to a public trading market for Hinsbrook shareholders whose investments currently are in a privately held company, as well as enhanced access to capital markets to finance the combined company’s capital requirements; and
the likelihood that the merger will be approved by the relevant bank regulatory authorities.
     Wintrust’s board of directors concluded that the merger is in the best interests of Wintrust and its shareholders. In deciding to approve the merger, Wintrust'sWintrust’s board of directors considered a number of factors, including: o management's view that the acquisition of Town Bankshares provides an attractive opportunity
Hinsbrook’s community banking orientation and its compatibility with Wintrust and its subsidiaries;
a review of the demographic, economic and financial characteristics of the markets in which Hinsbrook operates, including existing and potential competition and history of the market areas with respect to financial institutions;
management’s review of Hinsbrook’s business, operations, earnings and financial condition, including its management, capital levels and asset quality, since Hinsbrook Bank & Trust’sde novoformation in 1987; and
the likelihood of regulators approving the merger without undue conditions or delay.
Board recommendation to expand into certain markets in southeastern Wisconsin in which Wintrust does not currently operate and which management considers to be desirable markets; o Town Bankshares' community banking orientation and its compatibility with Wintrust and its subsidiaries; o a review of the demographic, economic and financial characteristics of the markets in which Town Bankshares operates, including existing and potential competition and history of the market areas with respect to financial institutions; o management's review of Town Bankshares' business, operations, earnings and financial condition, including its management, capital levels and asset quality, since its de novo formation in 1998; and o the likelihood of regulators approving the merger without undue conditions or delay. BOARD RECOMMENDATION TO TOWN BANKSHARES' SHAREHOLDERS (SeeHinsbrook’s shareholders(See page 27) Town Bankshares'28)
     Hinsbrook’s board of directors believes that the merger of Town BanksharesHinsbrook with Wintrust is in the best interests of Town BanksharesHinsbrook and its shareholders. TOWN BANKSHARES' BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT YOU VOTE "FOR" THE MERGER. 5 FAIRNESS OPINION OF TOWN BANKSHARES' FINANCIAL ADVISOR (See page 29) In deciding to approve the merger, Town Bankshares'Hinsbrook’s board of directors considered, among other things,unanimously recommends that you vote “FOR” the opinionmerger.
Interests of Edelman & Co., Ltd. thatofficers and directors of Hinsbrook in the merger considerationmay be different from, or in addition to, yours(See page 39)
     When you consider the Hinsbrook board of directors’ recommendation to vote in favor of the approval of the merger agreement, you should be aware that some of Hinsbrook’s directors and officers may have interests in the merger that are different from, or in addition to, your interests as shareholders. Hinsbrook’s board of directors was aware of these interests and took them into account in approving the merger. For example, the merger agreement obligates Hinsbrook Bank & Trust to enter into an employment agreement with each of Jeffrey D. Baker, Andrew M. Collins, Jr., L. Thomas McNamara and Regina R. Miller upon completion of the merger. The employment agreements between Hinsbrook Bank & Trust and Jeffrey D. Baker, Andrew M. Collins, Jr., L. Thomas McNamara and Regina R. Miller, obligate Hinsbrook Bank & Trust to make severance and other benefit payments under certain circumstances.
     In addition, Jeffrey D. Baker, Robert K. Buhrke, Andrew M. Collins, Jr., James R. Hannon, Jr., L. Thomas McNamara and Regina R. Miller have previously entered into change of control agreements with Hinsbrook Bank & Trust, and, in connection with the merger, each will be paid change of control payments to terminate such agreements.

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     Wintrust is also obligated under the merger agreement to provide continuing indemnification to Hinsbrook’s and Hinsbrook Bank & Trust’s directors and officers, and to provide such directors and officers with directors’ and officers’ liability insurance for a period of five years following the merger, subject to certain conditions set forth in the merger agreement.
Hinsbrook shareholders will have dissenters’ rights in connection with the merger(See page 23)
     Hinsbrook shareholders may dissent from the merger and, upon complying with the requirements of the IBCA, receive cash in the amount of the fair from a financial pointvalue of view,their shares instead of the merger consideration.
     A copy of the section of the IBCA pertaining to the holders of Town Bankshares common stock.dissenters’ rights is attached asAnnex Bto this proxy statement/prospectus. You should read the full textstatute carefully and consult with your legal counsel if you intend to exercise these rights.
The merger and the performance of the fairness opinion, which is attachedcombined company are subject to a number of risks(See page 17)
     There are a number of risks relating to the merger and to the businesses of Wintrust, Hinsbrook and the combined company following the merger. See “Risk Factors” beginning on page 17 of this proxy statement/prospectus as Annex D, to understand the assumptions made, limitsfor a discussion of the reviews undertakenthese and other matters consideredrisks and see also the documents that Wintrust has filed with the Securities and Exchange Commission and which we have incorporated by Edelman & Co., Ltd. in rendering its opinion. TOWN BANKSHARES SPECIAL MEETING (See page 19) The special meeting of shareholdersreference into this proxy statement/prospectus.
Hinsbrook shareholder approval will be held at _________________________, located at _______________________________, on _____________ ___, 2004 at __________, local time. Town Bankshares' board of directors is soliciting proxies for use atrequired to complete the special meeting. At the special meeting, Town Bankshares shareholders will be asked to vote on a proposal to approve the merger agreement. RECORD DATE FOR THE SPECIAL MEETING; REVOCABILITY OF PROXIES (See(See page 19) You may vote at the special meeting if you own shares of Town Bankshares common stock of record at the close of business on _____________ ___, 2004. You will have one vote for each share of Town Bankshares common stock you owned on that date. You may revoke your proxy at any time before the vote at the special meeting. VOTE REQUIRED (See page 19)22)
     To approve the merger, at least a majority of the voting power of the outstanding shares of Town BanksharesHinsbrook common stock entitled to vote must be voted in favor of the merger agreement at the special meeting. To satisfy the quorum requirements set forth in Town Bankshares'Hinsbrook’s by-laws, shareholders holding at least a majority of the voting power of the outstanding shares of Town BanksharesHinsbrook common stock entitled to vote at the special meeting must be present in person or by proxy at the special meeting. Shareholders may vote their shares in person at the special meeting or by signing and returning the enclosed proxy form. All
     On December 5, 2005, all of Town Bankshares'Hinsbrook’s directors and executive officers, haveincluding one executive officer who has since resigned, committed to vote their shares of common stock in favor of the merger. At the record date, these shareholders owned 50,3581,089,433 shares, constituting approximately 16.9%39.4% of the shares entitled to vote at the meeting. See "Description of the merger--Voting agreement"“The merger—Voting agreement” on page 36. VOTING BY PARTICIPANTS IN THE ESOP (See41.
Hinsbrook special meeting(See page 19) Each participant in22)
     The special meeting of shareholders will be held at the ESOP whose account has sharesmain office of Town Bankshares common stock allocatedHinsbrook Bank & Trust located at 6262 South Route 83, Willowbrook, Illinois 60527 on May 30, 2006 at 4:00 p.m., local time. Hinsbrook’s board of directors is soliciting proxies for use at the special meeting. At the special meeting, Hinsbrook shareholders will be asked to it as of _____________,vote on a proposal to approve the recordmerger agreement.
Record date for the special meeting; revocability of proxies(See pages 22 and 23)
     You may vote at the special meeting is eligible to direct the ESOP trustees to vote theif you own shares allocated to such participant's account by completing, signing and timely returning the "Direction to ESOP Administrator" form. These individuals include employees of Town Bankshares as of the record date who have shares allocated to their ESOP accounts as well as former employees of Town Bankshares who have not received a final distribution from the ESOP as of the record date. WHAT TOWN BANKSHARES SHAREHOLDERS WILL RECEIVE (See page 37) If the merger is completed, each share of Town BanksharesHinsbrook common stock that you own immediately beforeof record at the completionclose of the mergerbusiness on April 24, 2006. You will be converted into the right to receive shares of Wintrust common stock, plus cash in the amount of $58.10. For each of your shares of Town Bankshares common stock, you will receive a number of shares of Wintrust common stock equal to the "per share stock consideration" to be calculated as set forth in the merger agreement. The per share stock consideration will be determined by dividing $71.00 by the average of the high and low sale prices of Wintrust common stock during the 10-day trading period ending two trading days before the merger closing date, if the average price is at least $41.34 per share but not more than $55.34 per share. If the average price of the Wintrust common stock during this period is less than or equal to $41.34, you will receive 1.717 shares of Wintrust common stockhave one vote for each share of Town BanksharesHinsbrook common stock you own, and ifowned on that date. You may revoke your proxy at any time before the average pricevote at the special meeting.
Completion of the Wintrust common stock is greater than $55.34 per share, you will receive 1.283 shares of Wintrust common stock for each share of Town Bankshares common stock you own. 6 In effect, the merger agreement provides that the average high and low per share price of Wintrust common stock to be used in determining the per share stock consideration may not be higher than $55.34 nor less than $41.34. Within that price range, the per share stock consideration varies as the average price of Wintrust common stock changes so that the per share value of merger consideration which Town Bankshares shareholders receive remains constant and the number of Wintrust shares you receive will change. However, if the average price of Wintrust common stock is outside of that range, then the per share stock consideration does not change as Wintrust's stock price changes. As a result, if the average price of Wintrust common stock is less than $41.34, then you will receive a lower per share value of merger consideration at closing than you would receive if the average price of Wintrust common stock is within or above the range and, if the average price of Wintrust common stock is greater than $55.34, then you will receive a higher per share value of merger consideration at closing than you would if the average price of Wintrust common stock is within or below the range. However, subject to certain conditions, Wintrust may terminate the merger agreement if the average price of Wintrust common stock is greater than $58.34, and Town Bankshares may terminate the merger agreement if the average price of Wintrust common stock is less than $38.34. Town Bankshares shareholders will not receive fractional shares of Wintrust common stock. Instead, they will receive a cash payment for any fractional shares based on the value of Wintrust common stock determined in the manner described above. Once the merger is complete, Illinois Stock Transfer Company, Wintrust's exchange agent, will mail you materials and instructions for exchanging your Town Bankshares stock certificates for Wintrust stock certificates. You should not send in your Town Bankshares stock certificates until you receive the transmittal materials and instructions from the exchange agent. CASH REDEMPTION OF THE TOWN BANKSHARES COMMON STOCK IN THE ESOP (See page 44) The ESOP will not receive shares of Wintrust common stock and cash in the merger in exchange for the shares of Town Bankshares common stock held in the ESOP. Instead, the merger agreement provides that prior to the effective time of the merger, Town Bankshares will terminate the ESOP and redeem each share of Town Bankshares common stock in the ESOP for cash in the amount of $58.10 per share, plus the cash value of the per share stock consideration received by Town Bankshares' shareholders in the merger. We refer to such cash payment as the "ESOP cash redemption price" in this proxy statement/prospectus. Each participant's account will be credited with an amount equal to the number of shares of Town Bankshares common stock allocated to such participant's account multiplied by the ESOP cash redemption price. The ESOP cash redemption price for the unallocated shares of Town Bankshares common stock will be used first to repay the loan from Town Bankshares to the ESOP trust which had a total balance due of approximately $375,100 as of June 30, 2004. Town Bankshares has amended the ESOP to provide that the remainder of the ESOP cash redemption price for the unallocated shares will be allocated to the accounts of the ESOP participants pro rata based on compensation earned between January 1, 2004 and the date of termination of the ESOP. ESOP participants must be employed by Town Bankshares or its subsidiaries as of the date of the termination of the ESOP to share in this allocation. However, to the extent this allocation exceeds certain limitations under the Internal Revenue Code, the amount in excess of such limitations will be allocated to the accounts of all ESOP participants pro rata based on the account balances immediately prior to the redemption. The termination of the ESOP and the redemption of the shares of Town Bankshares common stock in the ESOP will not be effective unless the merger is subsequently completed. Termination of the ESOP will also cause all of the account balances of the ESOP participants to become fully vested. Following termination of the ESOP, subject to receipt of a favorable determination letter from the Internal Revenue Service, each ESOP participant will receive a distribution of the value of his or her account balance under the ESOP, which can be paid directly to the participant or rolled over to an IRA or eligible employer plan. REGULATORY APPROVALS (Seeregulatory approvals(See page 34)39)
     The merger cannot be completed until Wintrust receives the necessary regulatory approval of each of the Board of Governors of the Federal Reserve System, or the Federal Reserve, and the Division of Banking of the Illinois Department of Financial Institutions of the State of Wisconsin,and Professional Regulation, or the WDFI.IDFPR. Wintrust submitted an application toapplications with each of the Federal Reserve Bank of Chicago seeking approvaland the IDFPR in January of 2006 and received approvals from the Federal Reserve on February 24, 2006 and from the IDFPR on April 12, 2006.

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Conditions to the merger which application is still pending. Town 7 Bankshares has filed the required application with the Division of Banking of the WDFI, which application is still pending. NEW WINTRUST SHARES WILL BE ELIGIBLE FOR TRADING ON NASDAQ (See(See page 45) The shares of Wintrust common stock to be issued in the merger can be traded on the Nasdaq National Market. CONDITIONS TO THE MERGER (See page 41)47)
     The completion of the merger is subject to the fulfillment of a number of conditions, including: o
approval of the merger agreement at the special meeting by the holders of at least a majority of the outstanding shares of Hinsbrook common stock entitled to vote;
approval of the transaction by the appropriate regulatory authorities, including the Federal Reserve and the IDFPR, and expiration or termination of all waiting periods required by law;
absence of any threatened or pending suit, judgment or other action seeking to enjoin the consummation of the merger or seeking other relief that either Wintrust or Hinsbrook reasonably believes, subject to certain conditions, would have a material adverse effect on the other party;
authorization for listing the shares of Wintrust common stock issuable pursuant to the merger agreement on the Nasdaq National Market, subject to notice of final issuance;
maintenance by Hinsbrook of certain minimum net worth and loan loss reserve requirements;
receipt of an opinion of counsel to Hinsbrook that the merger constitutes a “reorganization” within the meaning of Section 368(a) of the Code;
the holders of not more than 5% of the outstanding shares of Hinsbrook common stock giving written demand for dissenters’ rights in accordance with the IBCA;
no material adverse change in Wintrust or Hinsbrook since December 5, 2005;
the execution of amendments to certain deferred compensation agreements;
the execution of an employment agreement by Jeffrey D. Baker, Andrew M. Collins, Jr., L. Thomas McNamara and Regina R. Miller; and
the representations and warranties made by the parties in the merger agreement must be materially true and correct as of the effective date of the merger or as otherwise required in the merger agreement.
How the merger agreement at the special meetingmay be terminated by the holders of at least a majority of the outstanding shares of Town Bankshares common stock; o approval of the transaction by the appropriate regulatory authorities, including the Federal ReserveWintrust and the Division of Banking of the WDFI,Hinsbrook(See page 49)
     Wintrust and expiration or termination of all waiting periods required by law; o maintenance by Town Bankshares of certain minimum shareholders' equity and loan loss reserve requirements; o the holders of not more than 10% of the outstanding shares of Town Bankshares common stock give written demand for dissenters' rights in accordance with Wisconsin law; o no material adverse change in Wintrust or Town Bankshares since June 14, 2004; o the execution of employment agreements by Jay C. Mack and Jeffrey A. Olsen; and o the representations and warranties made by the parties inHinsbrook may mutually agree to terminate the merger agreement must be materially true and correct asabandon the merger at any time prior to completion of the effective date of the merger or as otherwise required in the merger agreement. TERMINATION (See page 43)merger. Subject to conditions and circumstances described in the merger agreement, either Wintrust or Town BanksharesHinsbrook may terminate the merger agreement if, among other things, any of the following occur: o the merger is not completed by November 30, 2004 (or February 28, 2005,
the merger is not completed by July 31, 2006 (or August 31, 2006, if there is a delay due to regulatory approval);
in certain circumstances, if a condition to the merger has become impossible to satisfy;
in certain circumstances, if Hinsbrook has received and accepted a superior offer to sell to a third party; or
in certain circumstances by Hinsbrook if the average of the high and low sales price of Wintrust’s common stock on the Nasdaq National Market during the 10 days ending four trading days before the closing date is less than $47.14.

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Termination fees and expenses may be payable under some circumstances(See page 49)
     Generally, if there is a delay due to regulatory approval); o in certain circumstances, if a condition to the merger has become impossible to satisfy; o a party has materially breached the merger agreement is terminated by either Hinsbrook or Wintrust because the other party has committed a material breach, subject to certain limitations, the breaching party will be required to reimburse the non-breaching party for up to $250,000 in out-of-pocket costs and failed to cure the breach; o the holders of at least a majority of the voting power of Town Bankshares common stock do not approve the merger; o in certain circumstances, if Town Bankshares has received and accepted a superior offer to sell to a third party; or o the average of the high and low sales price of Wintrust's common stock during the 10-day trading period ending two trading days before the closing date is less than $38.34 or greater than $58.34. TERMINATION FEE (See page 43)expenses.
     Under certain circumstances described in the merger agreement, including (i) the breach by Hinsbrook of its agreement not to solicit alternative proposals or (ii) the entry into, consummation of or Hinsbrook’s board’s determination to accept, an unsolicited acquisition proposal from a third party, Wintrust may be owed a $1,000,000 termination fee from Town Bankshares if the transaction is not consummated.Hinsbrook. See "Description“Description of the merger agreement--Terminationagreement—Termination fee." 8 INTERESTS OF OFFICERS AND DIRECTORS IN THE MERGER THAT ARE DIFFERENT FROM YOURS (See
Voting agreement(See page 34) You should be aware that some of Town Bankshares' directors and officers may have interests in the merger that are different from, or in addition to, their interests as shareholders. Town Bankshares' board of directors was aware of these interests and took them into account in approving the merger. For example, the merger agreement obligates Wintrust to enter into employment agreements with Jay C. Mack, Town Bankshares' President and Chief Executive Officer and a director of Town Bankshares, and Jeffrey A. Olsen, Town Bankshares' Senior Vice President - Senior Lender. Town Bankshares also agreed to pay bonuses of $330,000 to Mr. Mack and $220,000 to Mr. Olsen contingent on (1) the execution by each executive officer of his employment agreement with Wintrust, (2) the execution by each executive officer of a release for the benefit of Town Bankshares, and (3) the closing of the merger. One-half of each stay bonus payment will be payable on the closing date of the merger and the other half will be payable on the later of the 60th-day following the closing date or January 2,41)
     On December 5, 2005, if the executive officer continues to be employed under the terms of his employment agreement as of such date, unless involuntarily or constructively terminated by Wintrust prior to such date. Wintrust is also obligated under the merger agreement to provide continuing indemnification to Town Bankshares' and Town Bank's directors and officers, and to provide such directors and officers with directors' and officers' liability insurance for a period of five years following the merger, subject to certain conditions set forth in the merger agreement. VOTING AGREEMENT (See page 36) Allall of the directors and executive officers of Town Bankshares haveHinsbrook, including one executive officer who has since resigned, agreed to vote all of their shares of common stock in favor of the merger agreement at the special meeting. Together, they ownThe voting agreement covers approximately 16.9%39.4% of Town Bankshares'Hinsbrook’s outstanding shares of common stock. These voting agreements terminate if the merger agreement is terminated in accordance with its terms. A copy of the form of voting agreement is attached to this proxy statement/prospectus asAnnex C. ACCOUNTING TREATMENT OF THE MERGER (SeeC.
Accounting treatment of the merger(See page 32)37)
     The merger will be accounted for as a purchase transaction in accordance with accounting principles generally accepted in the United States. CERTAIN DIFFERENCES IN SHAREHOLDER RIGHTS (See
Certain differences in shareholder rights(See page 45) When the merger is completed, Town Bankshares52)
     The rights of shareholders whose rightsof both Wintrust and Hinsbrook are governed by Wisconsin lawIllinois law. However, there are differences in the rights of Wintrust shareholders and Town Bankshares'Hinsbrook shareholders as a result of the provisions of the articles of incorporation, by-laws and by-laws, automaticallyother corporate documents of each company. After completion of the merger, Hinsbrook shareholders will become Wintrust shareholders and their rights will be governed by Illinois law, as well as Wintrust'sWintrust’s articles of incorporation and by-laws, in addition to laws and requirements that apply to public companies. DISSENTERS' RIGHTS (See page 21) Town Bankshares shareholders may dissent from the merger and, upon complying with the requirements of Wisconsin law, receive cash in the amount of the fair value of their
Wintrust shares instead of the merger consideration. Neither the ESOP nor its participants, however, will have dissenters' rights because all of the shares in the ESOP will be redeemed for cash prior to the completion of the merger. A copy of the sections of the Wisconsin Business Corporation Law pertaining to dissenters' rights is attached as Annex B to this proxy statement/prospectus. You should read the statute carefully and consult with your legal counsel if you intend to exercise these rights. TAX CONSEQUENCES OF THE MERGER (Seequoted on Nasdaq(See page 32) It is a condition to the closing of the merger that Town Bankshares' legal counsel render an opinion to Town Bankshares that the merger will constitute a reorganization under Section 368(a) of the Internal Revenue Code. If the merger constitutes a reorganization, the conversion of your shares of Town Bankshares common stock into Wintrust common stock may permit you to defer a portion of your "realized gain" in the exchange. For United States federal income tax purposes, your "realized gain" will be equal to the aggregate consideration (both stock and 9 cash) you receive in the reorganization less your basis in your Town Bankshares' stock exchanged.51)
     The portion of your "realized gain" which must be "recognized" will be equal to the lesser of the cash received (excluding cash received in lieu of fractional shares) or the realized gain as a result of the merger (adjusted for any gain recognized for cash received in lieu of fractional shares). In general, the tax basis in your shares of Town Bankshares common stock will carry over to the shares of Wintrust common stock you receiveto be issued pursuant to the merger will be quoted on the Nasdaq National Market under the symbol “WTFC.”

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Recent Developments
        Wintrust’s first quarter ended March 31, 2006. Wintrust has not finalized its financial statements for this period, and it is possible that actual results may vary from the information discussed below. Set forth below is a discussion of Wintrust’s preliminary unaudited financial information for the quarter ended March 31, 2006 with comparisons to the unaudited financial information for the quarter ended March 31, 2005. Wintrust’s results of operations for the quarter ended March 31, 2006 are not necessarily indicative of the results to be expected for the entire fiscal year 2006.
        Net income for the quarter ended March 31, 2006 was $19.0 million, an increase of $3.3 million, or 21%, over the $15.7 million recorded in the merger.first quarter of 2005. On a per share basis, net income for the first quarter of 2006 totaled $0.76 per diluted common share, an increase of $0.08 per share, or 12%, compared to the first quarter of 2005 total of $0.68 per diluted common share. The tax basisresults for the first quarter of 2006, when compared to the first quarter of 2005, benefited from additional trading income on the increase in the fair market value of debt swaps (approximately $0.09 per share) and a gain, net of sales expenses, from the sale of the Wayne Hummer Growth Fund (approximately $0.06 per share). Partially offsetting these increases was the impact of adopting the expensing of options under Statement of Financial Accounting Standards No. 123(R) (as amended) Share-Based Payments (approximately $0.03 per share).
        Total assets rose to $8.38 billion at March 31, 2006, an increase of $1.04 billion, or 14%, compared to $7.35 billion in total assets at March 31, 2005. Total deposits as of March 31, 2006 were $6.88 billion, an increase of $956 million, or 16%, as compared to $5.93 billion at March 31, 2005. Total loans grew to $5.44 billion as of March 31, 2006, an increase of $577 million, or 12%, over the $4.86 billion as of March 31, 2005.
        Additional details about Wintrust’s first quarter results can be found in Wintrust’s Current Report on Form 8-K filed with the SEC on April 21, 2006 incorporated by reference in this proxy statement/prospectus. See the section entitled “Incorporation of Certain Information by Reference” beginning on page 61.
Per Share Market Price and Dividend Information
     Wintrust common stock you receive inis quoted on the merger will equalNasdaq National Market under the tax basis in your Town Bankshares common stock exchanged for the merger consideration, decreased by the amount of any cash received (other than cash received in lieu of fractional shares of Town Bankshares common stock) and increased by the amount of any cash received which was treated as a dividend and the amount of any gain recognized in the exchange. The gain recognized as a result of cash received in lieu of a fractional share will be equal to the excess of such cash over the tax basis attributable to the share or shares of Town Bankshares common stock exchanged therefor. The holding period of your Wintrust common stock received in the merger will include the period during which you held Town Bankshares common stock, provided that the Town Bankshares common stock surrendered was held as a capital asset as of the time of the merger. You should consult your tax adviser for a full understanding of the federal, state, local and foreign tax consequences of the merger to you. HISTORICAL COMPARATIVE PER SHARE DATA; PRO FORMA PER SHARE DATAsymbol “WTFC.” The table below shows, for the quarters indicated, based on published financial sources, the reported high and low sales prices of Wintrust'sWintrust’s common stock during the periods indicated. This information gives effect to a 3-for-2 stock split, effected inindicated and the formcash dividends paid per share of a 50% stock dividend, as of March 14, 2002. HIGH LOW -------- -------- YEAR ENDED DECEMBER 31, 2002 First Quarter............................... $22.99 $18.33 Second Quarter.............................. 34.58 22.22 Third Quarter............................... 36.00 26.54 Fourth Quarter.............................. 32.66 25.45 YEAR ENDING DECEMBER 31, 2003 First Quarter............................... $33.65 $27.19 Second Quarter.............................. 32.40 27.74 Third Quarter............................... 38.89 29.30 Fourth Quarter.............................. 46.85 37.64 YEAR ENDING DECEMBER 31, 2004 First Quarter............................... $50.44 $41.85 Second Quarter.............................. 50.80 45.18 Third Quarter (through ________, 2004)...... __.__ __.__ 10 Wintrust common stock.
             
  High  Low  Dividend 
Year Ending December 31, 2003
            
First Quarter $33.65  $27.19  $0.08 
Second Quarter  32.40   27.74   0.00 
Third Quarter  38.89   29.30   0.08 
Fourth Quarter  46.85   37.64   0.00 
Year Ending December 31, 2004
            
First Quarter $50.44  $41.85  $0.10 
Second Quarter  50.80   45.18   0.00 
Third Quarter  58.42   49.82   0.10 
Fourth Quarter  63.39   54.33   0.00 
Year Ending December 31, 2005
            
First Quarter $57.23  $46.78  $0.12 
Second Quarter  52.93   45.00   0.00 
Third Quarter  55.50   49.01   0.12 
Fourth Quarter  59.63   48.00   0.00 
Year Ending December 31, 2006
            
First Quarter $58.94  $49.79  $0.14 
Second Quarter (through May 3) $59.64  $50.00  $0.00 

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Comparative Historical and Unaudited Pro Forma Per Share Data
     The following table presents selected comparative per share data for Wintrust common stock and Town BanksharesHinsbrook common stock on a historical and pro forma basis and unaudited pro forma condensed combined basis,consolidated per share information giving effect to the merger using the purchase method of accounting,accounting. You should read this information in conjunction with the selected historical financial information, included elsewhere in this proxy statement/prospectus, and the historical financial statements of Wintrust and related notes that are incorporated by reference in this proxy statement/prospectus by reference. The historical per share data is derived from audited financial statements as of and for Wintrust common stock on a pro forma combined basis, giving effect to the merger with both Town Bankshares and Wintrust's pending acquisition of Northview Financial Corporation, or Northview.year ended December 31, 2005.
     The consummation of Wintrust's merger with Town Bankshares is not conditioned upon completion of its pending acquisition of Northview. See "Description of the Merger--Business of Wintrust--Recent Developments." Theunaudited pro forma combined information isdoes not necessarily indicative ofpurport to represent what the actual results thatof operations of Wintrust and Hinsbrook would have occurredbeen had the mergercompanies been consummated atcombined during the beginningperiods presented or to project Wintrust’s and Hinsbrook’s results of operations that may be achieved after completion of the periods indicated, ormerger.
      
   Year Ended
   December 31, 2005
Wintrust Historical:
     
Diluted earnings per share  $2.75 
Cash dividends declared per share   0.24 
Book value per share (at period end)   26.23 
Wintrust Pro Forma Combined:(1)
     
Diluted earnings per share  $2.82 
Cash dividends declared per share   0.24 
Book value per share (at period end)   27.36 
Hinsbrook Historical:
     
Diluted earnings per share  $2.55 
Cash dividends declared per share   0.35 
Book value per share (at period end)   15.03 
Hinsbrook Pro Forma Combined:(1)
     
Diluted earnings per share  $2.31 
Cash dividends declared per share   0.20 
Book value per share (at period end)   22.38 
(1)Computed using per share merger consideration of $41.59 per share, assuming a Wintrust common stock price of $50.87 for the anticipated acquisition of Hinsbrook.

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Selected Historical Financial Data of the future operations of the combined entity. SIX MONTHS ENDED YEAR ENDED JUNE 30, 2004 DECEMBER 31, 2003 ---------------- ----------------- WINTRUST HISTORICAL: Diluted earnings per share............ $ 1.12 $ 1.98 Cash dividends declared per share..... 0.10 0.16 Book value per share (at period end).. 18.26 17.43 WINTRUST PRO FORMA COMBINED(1): Diluted earnings per share............ $ 1.14 $ 2.01 Cash dividends declared per share..... 0.10 0.16 Book value per share (at period end).. 19.10 18.30 WINTRUST PRO FORMA COMBINED (TOWN BANKSHARES AND NORTHVIEW)(1)(2): Diluted earnings per share............ $ 1.15 $ 2.05 Cash dividends per share.............. 0.10 0.16 Book value per share (at period end).. 19.96 19.20 TOWN BANKSHARES HISTORICAL: Diluted earnings per share............ $ 2.79 $ 4.19 Cash dividends declared per share..... -- -- Book value per share (at period end).. 59.70 56.98 TOWN BANKSHARES PRO FORMA COMBINED(1): Diluted earnings per share............ $ 1.55 $ 2.74 Cash dividends declared per share..... 0.14 0.22 Book value per share (at period end).. 26.09 25.00 - ---------------------- (1) Computed using per share stock consideration of 1.3664 shares of Wintrust common stock per share of Town Bankshares common stock, assuming a Wintrust common stock price of $51.96. (2) Computed using per share stock consideration of 2.9109 shares of Wintrust common stock per share of Northview common stock, assuming a Wintrust common stock price of $51.96. The following table sets forth the last sales prices as reported by Nasdaq for Wintrust common stock on the dates indicated, and the equivalent per share value of Town Bankshares common stock, giving effect to the merger, as of the same dates: HISTORICAL PRICE TOWN CLOSING PRICE TOWN BANKSHARES WINTRUST BANKSHARES EQUIVALENT PER COMMON STOCK COMMON STOCK SHARE VALUE ------------- -------------- --------------- June 14, 2004(1).......... $46.85 (2) $129.10(3) _________ __, 2004........ $____ (2) $______(4) - ---------------------- (1) Trading date immediately preceding the date of public announcement of the proposed merger. (2) There is currently no market value for the shares of Town Bankshares being acquired since Town Bankshares is not a publicly traded company. (3) Based on per share stock consideration of 1.515 shares of Wintrust common stock and per share cash consideration of $58.10. (4) Based upon per share stock consideration of _____ shares of Wintrust common stock and per share cash consideration of $_____. 11 SELECTED FINANCIAL DATA OF WINTRUST
     The selected consolidated financial data presented below is being provided to assist you in your analysis of the financial aspects of the merger. The annual Wintrust historical information as of orand for each of the years in the five-year period ended December 31, 2003,2005, are derived from Wintrust'sWintrust’s audited historical financial statements. The selected consolidated financial data presented below, as of or for the six-month periods ended June 30, 2004 and 2003, are derived from unaudited consolidated financial statements. In Wintrust's opinion, all adjustments, consisting only of normal recurring adjustments, necessary for a fair statement of results as of or for the six-month periods, have been included. Share and per share amounts have been adjusted to reflect the 3-for-2 stock split effected as a stock dividend effective as of March 14, 2002. This information is only a summary and should be read in conjunction with "Management's“Management’s Discussion and Analysis of Financial Condition and Results of Operations"Operations” and the consolidated financial statements and the notes thereto incorporated by reference into this proxy statement/prospectus from Wintrust'sWintrust’s Annual Report on Form 10-K for the fiscal year ended December 31, 2003, and Wintrust's Quarterly Report on Form 10-Q for the period ended June 30, 2004. Results for past periods2005. The historical results below or contained elsewhere in this proxy statement/prospectus are not necessarily indicative of results that may be expected for anythe future period, and results forperformance of Wintrust or the six-month period ended June 30, 2004 are not necessarily indicative of results that may be expected for the entire year ending December 31, 2004. combined company.
                    
         
  Year Ended December 31,
  2005(1)  2004(2)  2003(3)  2002(4)  2001
  (Dollars in thousands, except per share amounts)
Statement of Income Data:
                   
Total interest income $407,036  $261,746  $203,991  $182,233  $166,455
Total interest expense  197,227   103,922   83,499   84,105   92,441
               
Net interest income  216,759   157,824   120,492   98,128   74,014
Provision for loan losses  6,676   6,298   10,999   10,321   7,900
               
Net interest income after provision for loan losses  210,083   151,526   109,493   87,807   66,114
 
Non-interest Income:
                   
Gain on sale of premium finance receivables  6,499   7,347   4,911   3,374   4,564
Mortgage banking revenue  25,913   18,250   16,718   13,271   8,106
Wealth management fees  30,008   31,656   28,871   25,229   1,996
Services charges on deposit account  5,983   4,100   3,525   3,121   2,504
Administrative services revenue  4,539   3,984   4,151   3,501   4,084
Premium finance Defalcation-partial settlement(5)
        500   1,250   
Securities (losses) gains, net  1,063   1,863   642   107   337
Other  19,552   18,252   13,274   10,819   7,207
               
Total non-interest Income  93,557   85,452   72,592   60,672   28,798
               
(See footnotes on page 16)

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  Year Ended December 31,
  2005(1)  2004(2)  2003(3)  2002(4)  2001
  (Dollars in thousands, except per share amounts)
Non-interest Expense:
                   
Salaries and employee benefits $118,071  $94,049  $74,775  $63,442  $35,628
Equipment expense  11,779   9,074   7,957   7,191   6,297
Occupancy expense, net  16,176   10,083   7,436   6,691   4,821
Data processing  7,129   5,560   4,304   4,161   3,393
Advertising and marketing  4,970   3,403   2,215   2,302   1,604
Professional fees  5,609   5,376   3,342   2,801   2,055
Amortization of intangibles  3,394   1,110   640   324   685
Premium finance defalcation(5)
              
Other non-interest expenses  31,562   27,436   22,072   19,072   11,300
               
Total non-interest expenses  198,690   156,091   122,741   105,984   65,783
               
                    
Income before taxes and cumulative effect of accounting change  104,950   80,887   59,344   42,495   29,129
Income tax expense  37,934   29,553   21,226   14,620   10,436
               
Income before cumulative effect of accounting change $67,016   51,334   38,118   27,875   18,693
Cumulative effect of change in accounting for derivatives, net of tax              (254)
               
Net income $67,016  $51,334  $38,118  $27,875  $18,439
               
                    
Common Share Data:
                   
Earnings per share:                   
Basic $2.89  $2.49  $2.11  $1.71  $1.34
Diluted  2.75   2.34   1.98   1.60   1.27
Cash dividends per common share(6)
  0.24   0.20   0.16   0.12   0.093
Book value per share  26.23   21.81   17.43   13.19   9.72
                    
Weighted average common shares outstanding:                   
Basic  23,198   20,646   18,032   16,334   13,734
Diluted:  24,337   21,972   19,219   17,445   14,545
                    
Selected Financial Condition Data (at end of period):
                   
Total assets $8,117,042  $6,419,048  $4,747,398  $3,721,555  $2,705,422
Total loans  5,213,871   4,348,346   3,297,794   2,556,086   2,018,479
Mortgage loans held-for-sale  85,985   104,709   24,041   90,446   42,904
Total deposits  6,729,434   5,104,734   3,876,621   3,089,124   2,314,636
Notes payable  1,000   1,000   26,000   44,025   46,575
Subordinated notes  50,000   50,000   50,000   25,000   
Long term debt – trust preferred securities  230,458   204,489   96,811   50,894   51,050
Total stockholders’ equity  627,911   473,912   349,837   227,002   141,278
(See footnotes on following page)

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  Year Ended December 31,
  2005(1) 2004(2) 2003(3) 2002(4) 2001
Selected Financial Ratios and Other Data:
                    
Performance Ratios:
                    
Net interest margin(7)(8)
  3.16%  3.17%  3.20%  3.34%  3.49%
Net interest spread(7)(9)(10)
  2.92   2.96   2.99   3.06   3.08 
Non-interest income to average assets(7)
  1.23   1.57   1.76   1.89   1.24 
Non-interest expense to average assets(5)(7)
  2.62   2.86   2.98   3.30   2.83 
Net overhead ratio(5)(7)(11)
  1.39   1.30   1.22   1.41   1.59 
Efficiency ratio(5)(12)
  63.97   64.45   63.52   66.41   63.66 
Return on average assets(5)(7)
  0.88   0.94   0.93   0.87   0.79 
Return on average equity(5)(7)
  11.00   13.12   14.36   14.76   15.24 
Average loan-to-average deposit ratio  83.4   87.7   86.4   88.5   87.4 
Dividend payout ratio(6)(7)
  8.7   8.5   8.1   7.5   7.4 
                     
Asset Quality Ratios:
                    
Non-performing loans to total loans  0.50%  0.43%  0.72%  0.49%  0.64%
Allowance for credit losses to:                    
Total loans  0.78   0.79   0.77   0.72   0.68 
Non-performing loans  155.69   184.13   107.59   146.63   105.63 
Net charge-offs to average loans(5)(7)
  0.10   0.07   0.18   0.24   0.26 
Non-performing assets to total assets  0.34   0.29   0.51   0.34   0.48 
                     
Other data at end of period:
                    
Number of banking facilities  62   50   36   31   29 
SIX MONTHS ENDED JUNE 30, YEAR ENDED DECEMBER 31, 2004(1) 2003 2003(2) 2002(3) 2001 2000 1999 --------- --------- --------- --------- --------- --------- --------- (IN THOUSANDS, EXCEPT PER SHARE AMOUNTS) STATEMENT OF INCOME DATA: Total interest income.....$ 119,307 $ 96,504 $ 203,991 $ 182,233 $ 166,455 $ 148,184 $ 109,331 Total interest expense.... 46,079 41,572 83,499 84,105 92,441 87,184 61,597 ---------- ---------- ---------- ---------- ---------- ---------- ---------- Net interest income.... 73,228 54,932 120,492 98,128 74,014 61,000 47,734 Provision for loan losses................. 3,762 5,493 10,999 10,321 7,900 5,055 3,713 ---------- ---------- ---------- ---------- ---------- ---------- ---------- Net interest income after provision for loan losses..... 69,466 49,439 109,493 87,807 66,114 55,945 44,021 Non-interest Income: Gain on sale of premium finance receivables......... 3,539 2,270 4,911 3,374 4,564 3,831 1,033 Mortgage banking revenue............. 7,256 9,797 16,718 13,271 8,106 3,139 3,423 Wealth management fees................ 16,496 12,953 28,871 25,229 1,996 1,971 1,171 Service charges on deposit accounts.... 1,946 1,722 3,525 3,121 2,504 1,936 1,562 Administrative services revenues 1,887 2,159 4,151 3,501 4,084 4,402 996 Premium finance defalcation-partial settlement(4)....... -- -- 500 1,250 -- -- -- Securities (losses) gains, net.......... 853 606 642 107 337 (40) 5 Other.................. 8,204 7,341 13,274 10,819 7,207 3,067 1,618 ---------- ---------- ---------- ---------- ---------- ---------- ---------- Total non-interest income............ 40,181 36,848 72,592 60,672 28,798 18,306 9,808 ---------- ---------- ---------- ---------- ---------- ---------- ---------- (See footnotes on page 14)
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SIX MONTHS ENDED JUNE 30, YEAR ENDED DECEMBER 31, 2004(1) 2003 2003(2) 2002(3) 2001 2000 1999 --------- --------- --------- --------- --------- --------- --------- (IN THOUSANDS, EXCEPT PER SHARE AMOUNTS) Non-interest Expense: Salaries and employee benefits $ 43,073 $ 35,715 $ 74,775 $ 63,442 $ 35,628 $ 28,119 $ 20,808 Equipment expense...... 4,351 3,758 7,957 7,191 6,297 5,101 3,199 Occupancy expense, net................. 4,497 3,785 7,436 6,691 4,821 4,252 2,991 Data processing........ 2,652 2,079 4,304 4,161 3,393 2,837 2,169 Advertising and marketing........... 1,590 1,043 2,215 2,302 1,604 1,309 1,402 Professional fees...... 2,143 1,704 3,342 2,801 2,055 1,681 1,203 Amortization of intangibles......... 393 298 640 324 685 713 251 Premium finance defalcation(4)...... -- -- -- -- -- 4,320 -- Other non-interest expenses......... ... 12,944 11,038 22,072 19,072 11,300 9,471 7,655 ---------- ---------- ---------- ---------- ---------- ---------- ---------- Total non-interest expense........... 71,643 59,420 122,741 105,984 65,783 57,803 39,678 ---------- ---------- ---------- ---------- ---------- ---------- ---------- Income before taxes and cumulative effect of accounting change...... 38,004 26,867 59,344 42,495 29,129 16,448 14,151 Income tax expense (benefit).............. 13,917 9,585 21,226 14,620 10,436 5,293 4,724 ---------- ---------- ---------- ---------- ---------- ---------- ---------- Income before cumulative effect of accounting change... 24,087 17,282 38,118 27,875 18,693 11,155 9,427 Cumulative effect of change in accounting for derivatives, net of tax.................... -- -- -- -- (254) -- -- ---------- ---------- ---------- ---------- ---------- ---------- ---------- Net income.............$ 24,087 $ 17,282 $ 38,118 $ 27,875 $ 18,439 $ 11,155 $ 9,427 ========== ========== ========== ========== ========== ========== ========== COMMON SHARE DATA: Earnings per share: Basic..................$ 1.19 $ 1.00 $ 2.11 $ 1.71 $ 1.34 $ 0.85 $ 0.76 Diluted................ 1.12 0.94 1.98 1.60 1.27 0.83 0.73 Cash dividends per common share(5)........ 0.10 0.08 0.16 0.12 0.093 0.067 -- Book value per share...... 18.26 14.31 17.43 13.19 9.72 7.92 7.06 Weighted average common shares outstanding: Basic.................. 20,250 17,360 18,032 16,334 13,734 13,066 12,373 Diluted................ 21,564 18,473 19,219 17,445 14,545 13,411 12,837 SELECTED FINANCIAL CONDITION DATA (AT END OF PERIOD): Total assets..............$5,326,179 $4,132,394 $4,747,398 $3,721,555 $2,705,422 $2,102,806 $1,679,382 Total loans............... 3,695,551 2,896,148 3,297,794 2,556,086 2,018,479 1,547,596 1,270,126 Total deposits............ 4,324,368 3,419,946 3,876,621 3,089,124 2,314,636 1,826,576 1,463,622 Notes payable............. 1,000 26,000 26,000 44,025 46,575 27,575 8,350 Subordinated notes........ 50,000 50,000 50,000 25,000 -- -- -- Long term debt - trust preferred securities 139,587 76,816 96,811 50,894 51,050 51,050 31,050 Total shareholders' equity................. 374,152 249,399 349,837 227,002 141,278 102,276 92,947 (See footnotes on following page)
13
SIX MONTHS ENDED JUNE 30, YEAR ENDED DECEMBER 31, 2004(1) 2003 2003(2) 2002(3) 2001 2000 1999 --------- --------- --------- --------- --------- --------- --------- SELECTED FINANCIAL RATIOS AND OTHER DATA: Performance Ratios: Non-interest income to average assets(6)........... 1.60% 1.92% 1.76% 1.89% 1.24% 0.99% 0.66% Non-interest expense to average assets(4)(6)........ 2.85 3.10 2.98 3.30 2.83 3.12 2.65 Net overhead ratio(4)(6)(7)...... 1.25 1.18 1.22 1.41 1.59 2.13 2.00 Return on average assets(4)(6)........ 0.96 0.90 0.93 0.87 0.79 0.60 0.63 Return on average equity(4)(6)........ 13.41 14.74 14.36 14.76 15.24 11.51 11.58 Average loan-to-average deposit ratio....... 87.5 86.1 86.4 88.5 87.4 87.7 86.6 Dividend payout ratio(5)(6)......... 8.9 8.5 8.1 7.5 7.4 8.0 -- Asset Quality Ratios: Non-performing loans to total loans............... 0.40% 0.47% 0.72% 0.49% 0.64% 0.63% 0.55% Allowance for loan losses to: Total loans......... 0.76 0.74 0.77 0.72 0.68 0.67 0.69 Non-performing loans............. 191.34 156.42 107.59 146.63 105.63 107.75 126.10 Net charge-offs to average loans(4)(6)......... 0.07 0.19 0.18 0.24 0.26 0.24 0.19 Non-performing assets to total assets.............. 0.31 0.35 0.51 0.34 0.48 0.46 0.41 Other data at end of period: Number of banking facilities.......... 42 32 36 31 29 28 24 - ----------------------
(1)Wintrust completed its acquisitionacquisitions of Antioch Holding Company on January 18, 2005 and First Northwest Bancorp, Inc. on March 31, 2005. The results for the fiscal year ended December 31, 2005 include the results of Antioch Holding Company and First Northwest Bancorp, Inc. since the effective date of the acquisitions.
(2)Wintrust completed its acquisitions of SGB Corporation d/b/a WestAmerica Mortgage Company and its affiliate, Guardian Real Estate Services, Inc., effective as of on May 1,19, 2004, and Northview Financial Corporation on September 30, 2004. The results for the six monthsyear ended June 30,December 31, 2004 include the results of such companiesWestAmerica and Guardian since that date. (2) the effective date of the acquisition.
(3)Wintrust completed its acquisitions of Lake Forest Capital Management Company on February 1, 2003, Advantage National Bancorp, Inc. on October 1, 2003 and Village Bancorp, Inc. effective as of February 1, 2003, October 1, 2003 andon December 1, 2003, respectively.5, 2003. The results for the year ended December 31, 2003 include the results of Lake Forest Capital Management Company, Advantage National Bancorp, Inc.the companies acquired as of and Village Bancorp, Inc. since their respective datesthe effective date of acquisition. (3) the acquisitions only.
(4)Wintrust completed its acquisition of the Wayne Hummer Companies effective as of February 1, 2002. The results for the year ended December 31, 2002 include the results of the Wayne Hummer Companies since February 1, 2002. (4)
(5)In 2000, Wintrust recorded a $4.3 million pre-tax charge ($2.6 million after-tax) related to a fraudulent loan scheme perpetrated against its premium finance subsidiary. The amount of this charge was not included in loans charged-off because a lending relationship had never been established. In the first quarter of 2002, Wintrust recovered $1.25 million (pre-tax) of this amount ($754,000 after-tax). Additionally,, and in the fourth quarter of 2003, Wintrustit recovered $500,000 (pre-tax) of this amount ($302,000 after-tax). (5)
(6)Wintrust declared its first semi-annual dividend payment in January 2000. Dividend data reflected for the interim periods reflect semi-annual, not quarterly, dividends. (6) Certain
(7)These financial ratios for interim periods have been annualized. (7)
(8)Net interest income on a tax-equivalent basis divided by average interest-earning assets.
(9)Calculated on a tax-equivalent basis.
(10)Yield earned on average interest-earning assets less rate paid on average interest-bearing liabilities.
(11)Non-interest expense less non-interest income divided by average total assets.
(12)Non-interest expense (excluding non-recurring items) divided by the sum of net interest income on a tax equivalent basis plus non-interest income (excluding securities gains and losses).
14

16


RISK FACTORS
In addition to the other information contained in or incorporated by reference into this proxy statement/prospectus, including the matters addressed under the caption "Caution About Forward-Looking Statements"“Forward-Looking Statements” on page 17,21, you should consider the following risk factors carefully in deciding whether to vote for the adoptionapproval of the merger agreement. THERE IS FLUCTUATION IN THE TRADING MARKET OF WINTRUST'S COMMON STOCK AND THE MARKET PRICE OF THE COMMON STOCK YOU WILL RECEIVE IN THE MERGER IS UNCERTAIN. You will receiveAdditional risks and uncertainties not presently known to Wintrust common stockand Hinsbrook or that are not currently believed to be important to you, if they materialize, also may adversely affect the merger and Wintrust and Hinsbrook as a combined company.
In addition, Wintrust’s and Hinsbrook’s respective businesses are subject to numerous risks and uncertainties, including the risks and uncertainties described, in the merger. The number of shares you receive will depend on the average pricecase of Wintrust, common stock priorin its Annual Report onForm 10-K for the year ended December 31, 2005, which is incorporated by reference into this proxy statement/prospectus. These risks and uncertainties will continue to apply to Wintrust and Hinsbrook as independent companies if the merger is not consummated.
Risks relating to the merger. Changes inmerger
Because the market price of Wintrust common stock may result from a varietyfluctuate, you cannot be certain of factors, including general market and economic conditions, the future financial condition and operating resultsprecise value of Wintrust, changesthe stock portion of the merger consideration you may receive in Wintrust's business, operations and prospects and regulatory considerations, manythe merger.
     You cannot be certain of which are beyond Wintrust's control. The pricethe precise value of the stock portion of the merger consideration to be received at closing. If the merger is completed, you will be entitled to receive, for each share of Hinsbrook common stock that you elect to convert into shares of Wintrust common stock, at completiona fraction of the merger may vary from its pricea share of Wintrust common stock equal to an exchange ratio based on the date the merger agreement was signed, from its price on the date of this proxy statement/prospectus, from its price on the date of the special meeting and from the averagereference price during the 10-day pricing period usedreference price determination period. The exchange ratio will adjust to determineensure that the numberfraction of sharesa share of Wintrust common stock you arereceive will be equal to receive. You will not$41.59 divided by the reference price so long as the reference price is between $49.14 and $61.14. However, the market value of that fraction of a share of Wintrust common stock you receive may be entitled to receive additional cashgreater or shares inless than $41.59, as the merger if thetrading price of Wintrust common stock on the closing date of the merger may be greater or less than the reference price used to determine the exchange ratio. If the reference price is less than $49.14, the average price duringexchange ratio will no longer adjust upward. This means that the pricing period. Because the merger will be completed after the datevalue of the special meeting, at the timefraction of the special meeting you will not know what the market valuea share of the Wintrust common stock you will receive afterwill be below $41.59 to the mergerextent the reference price is below $49.14. If the reference price is greater than $61.14, the exchange ratio will be. See "Descriptionno longer adjust downward. This means that the value of the fraction of a share of Wintrust common stock you will receive will be above $49.14 to the extent the reference price is above $49.14. The formula for calculating the exchange ratio is set forth in the section entitled “Description of the merger agreement--Considerationagreement—Consideration to be received in the merger." Wintrust'smerger” beginning on page 42.
     Wintrust’s common stock is traded on the Nasdaq National Market under the symbol "WTFC".“WTFC.” The maintenance of an active public trading market depends, however, upon the existence of willing buyers and sellers, the presence of which is beyond Wintrust'sWintrust’s control or the control of any market maker. In addition to the shares of Wintrust common stock to be issued in the merger, Wintrust also has shares of common stock covered by resale registration statements andstatements. Wintrust estimates that there are currently approximately up to 1,075,000967,000 of those shares outstanding that have not yet been resold. These remaining shares may be freely sold from time to time in the market. The market price of Wintrust'sWintrust’s common stock could drop significantly if shareholders sell or are perceived by the market as intending to sell large blocks of its shares. TOWN BANKSHARES' SHAREHOLDERS WILL NOT CONTROL WINTRUST'S FUTURE OPERATIONS.
Wintrust and Hinsbrook may be unable to successfully integrate their operations and may not realize the anticipated benefits of combining Wintrust and Hinsbrook.
     Wintrust and Hinsbrook entered into the merger agreement with the expectation that they would be able to successfully integrate their operations and that the merger would result in various benefits, including, among other things, enhanced revenues and revenue synergies, an expanded market reach and operating efficiencies. Achieving the anticipated benefits of the merger is subject to a number of uncertainties, including whether Wintrust integrates and operates Hinsbrook in an efficient and effective manner, and general competitive factors in the market place. The process of integrating operations could cause an interruption of, or loss of momentum in, the activities of one or more of the combined company’s businesses or the loss of key personnel. The diversion of management’s attention and any delays or difficulties encountered in connection with the merger and the integration of the two companies’

17


operations could have an adverse effect on the business, financial condition, operating results and prospects of the combined company after the merger. Failure to achieve these anticipated benefits could result in increased costs, decreases in the amount of expected revenues and diversion of management’s time and energy and could have an adverse effect on the combined company’s business, financial condition, operating results and prospects.
     Among the factors considered by the boards of directors of Wintrust and Hinsbrook in connection with their respective approvals of the merger agreement were the benefits that could result from the merger. We cannot give any assurance that these benefits will be realized within the time periods contemplated or even that they will be realized at all.
Hinsbrook will be subject to business uncertainties while the merger is pending, which could adversely affect its business.
     Uncertainty about the effect of the merger on employees and customers may have an adverse effect on Hinsbrook, and, consequently, the combined company. Although Hinsbrook intends to take steps to reduce any adverse effects, these uncertainties may impair Hinsbrook’s ability to attract, retain and motivate key personnel until the merger is consummated and for a period of time thereafter, and could cause customers and others that deal with Hinsbrook to seek to change their existing business relationships with Hinsbrook. Employee retention at Hinsbrook may be particularly challenging during the pendency of the merger, as employees may experience uncertainty about their roles with the combined company following the merger.
Some of the directors and executive officers of Hinsbrook have interests and arrangements that could have affected their respective decision to support or approve the merger.
     The interests of some of the directors and executive officers of Hinsbrook in the merger are different from, and may be in addition to, those of Hinsbrook shareholders generally and could have affected their decision to support or approve the merger. These interests include:
The change of control payments, pursuant to existing contracts, to each of Jeffrey D. Baker, Robert K. Buhrke, Andrew M. Collins, Jr., James R. Hannon, Jr., L. Thomas McNamara and Regina R. Miller in connection with the merger;
The entry into employment agreement with each of Jeffrey D. Baker, Andrew M. Collins, Jr., L. Thomas McNamara and Regina R. Miller upon completion of the merger;
Wintrust’s agreement to provide severance and other benefit payments under certain circumstances to Jeffrey D. Baker, Andrew M. Collins, Jr., L. Thomas McNamara and Regina R. Miller;
Wintrust’s agreement to provide officers and directors of Hinsbrook with continuing indemnification rights; and
Wintrust’s agreement to provide directors’ and officers’ insurance to the officers and directors of Hinsbrook for five years following the merger.
     As a result, the directors and officers of Hinsbrook may be more likely to recommend to Hinsbrook’s shareholders the approval of the merger agreement than if they did not have these interests.
Risks relating to the businesses of Wintrust and the combined company
Hinsbrook’s shareholders will not control Wintrust’s future operations.
     Currently, Town Bankshares'Hinsbrook’s shareholders own 100% of Town BanksharesHinsbrook and have the power to approve or reject any matters requiring shareholder approval under WisconsinIllinois law and Town Bankshares'Hinsbrook’s articles of incorporation and by-laws. After the merger, Town BanksharesHinsbrook shareholders will become owners of less than ___%7% of the outstanding shares of Wintrust common stock. Even if all former Town BanksharesHinsbrook shareholders voted together on all matters presented to WintrustWintrust’s shareholders, from time to time, the former Town BanksharesHinsbrook shareholders most likely would not have a significant impact on the approval or rejection of future Wintrust proposals submitted to a shareholder vote. DE NOVO OPERATIONS AND BRANCH OPENINGS IMPACT WINTRUST'S PROFITABILITY. Wintrust's

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De novo operations and branch openings impact Wintrust’s profitability.
     Wintrust’s financial results have been and will continue to be impacted by its strategy ofde novobank formations and branch openings. Wintrust has employed this strategy to build an infrastructure that management believes can support additional internal growth in its banks'banks’ respective markets. Wintrust opened its eighth operatesde novo bank in April 2004,banks, and expects to undertake additionalde novo bank formations or branch openings as it expands into additional communities in and around Chicago and southeasternsoutheast Wisconsin. In addition, Wintrust's recent and pending acquisitions involve relatively recently formed fact, on December 8, 2005, Wintrust announced plans to open ade novo banks. bank in the south suburbs of Chicago with three locations. Thisde novo bank began operations in March of 2006. Based on Wintrust'sWintrust’s experience, its management believes that it generally takes from 13 to 24 months for new de novobanks to first achieve operational profitability, depending on the number of branchbanking facilities opened, the impact of organizational and overhead expenses, the start-up phase of generating deposits and the time lag typically involved in redeploying deposits into attractively priced loans and other higher yielding earning assets. However, it may take longer than expected or than the amount of time Wintrust has historically experienced for new banks and/or branchbanking facilities to reach 15 profitability, and there can be no guarantee that these new banks or branches will ever be profitable. To the extent Wintrust undertakes additionalde novobank, branch and business formations, its level of reported net income, return on average equity and return on average assets will be impacted by start-up costs associated with such operations, and it is likely to continue to experience the effects of higher expenses relative to operating income from the new operations. These expenses may be higher than Wintrust expected or than its experience has shown. WINTRUST'S ALLOWANCE FOR LOAN LOSSES MAY PROVE TO BE INSUFFICIENT TO ABSORB LOSSES THAT MAY OCCUR IN ITS LOAN PORTFOLIO. Wintrust's
Wintrust’s allowance for credit losses may prove to be insufficient to absorb losses that may occur in its loan portfolio.
     Wintrust’s allowance for loan losses is established in consultation with management of its operating subsidiaries and is maintained at a level considered adequate by management to absorb loan losses that are inherent in the portfolios. At June 30, 2004, Wintrust'sDecember 31, 2005, Wintrust’s allowance for loan losses was 191.34%155.69% of total nonperforming loans and 0.76%0.78% of total loans. The amount of future losses is susceptible to changes in economic, operating and other conditions, including changes in interest rates, that may be beyond its control, and such losses may exceed current estimates. Rapidly growing andde novobank loan portfolios are, by their nature, unseasoned. As a result, estimating loan loss allowances for Wintrust'sWintrust’s newer banks is more difficult, and, therefore, the banks may be more susceptible to changes in estimates, and to losses exceeding estimates, than banks with more seasoned loan portfolios. Although management believes that the allowance for loan losses is adequate to absorb losses that may develop in Wintrust'sWintrust’s existing portfolios of loans and leases, there can be no assurance that the allowance will prove sufficient to cover actual loan or lease losses in the future. WINTRUST'S PREMIUM FINANCE BUSINESS INVOLVES UNIQUE OPERATIONAL RISKS AND COULD EXPOSE IT TO SIGNIFICANT LOSSES.
Wintrust’s premium finance business involves unique operational risks and could expose it to significant losses.
     Of Wintrust'sWintrust’s total loans at June 30, 2004, 21%December 31, 2005, 16%, or $790.9approximately $815 million, were comprised of commercial insurance premium finance receivables that it generates through First Insurance Funding Corporation. These loans, intended to enhance the average yield of earning assets of its banks, involve a different, and possibly higher, level of risk of delinquency or collection than generally associated with loan portfolios of more traditional community banks. First Insurance also faces unique operational and internal control challenges due to the relatively rapid turnover of the premium finance loan portfolio and high volume of new loan originations. The average term to maturity of these loans is less than 12 months, and the average loan size when originated is approximately $30,000.less than $50,000.
     Because Wintrust conducts lending in this segment primarily through relationships with a large number of unaffiliated insurance agents and because the borrowers are located nationwide, risk management and general supervisory oversight may be more difficult than in its banks. Wintrust may also be more susceptible to third party fraud. Acts of fraud are difficult to detect and deter, and Wintrust cannot assure investors that its risk management procedures and controls will prevent losses from fraudulent activity. For example, in the third quarter of 2000, Wintrust recorded a non-recurring after-tax charge of $2.6 million in connection with a series of fraudulent loan transactions perpetrated against First Insurance by one independent insurance agency located in Florida. Although Wintrust has since enhanced its internal controls system at First Insurance, it may continue to be exposed to the risk of significant loss in its premium finance business.
     Due to continued growth in origination volume of premium finance receivables, since the second quarter of 1999, Wintrust has been selling some of the loans First Insurance originates to an unrelated third party. Wintrust has

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recognized gains on the sales of the receivables, and the proceeds of sales have provided it with additional liquidity. Consistent with its strategy to be asset driven, Wintrust expects to pursue similar sales of premium finance receivables in the future; however, it cannot assure you that there will continue to be a market for the sale of these loans and the extent of Wintrust'sWintrust’s future sales of these loans will depend on the level of new volume growth in relation to its capacity to retain the loans within its subsidiary banks'banks’ loan portfolios. Because Wintrust has a recourse obligation to the purchaser of premium finance loans that it sells, it could incur losses in connection with the loans sold if collections on the underlying loans prove to be insufficient to repay to the purchaser the principal amount of the loans sold plus interest at the negotiated buy-rate and if the collection shortfall on the loans sold exceeds Wintrust'sWintrust’s estimate of losses at the time of sale. 16 WINTRUST MAY BE ADVERSELY AFFECTED BY INTEREST RATE CHANGES. Wintrust's
Wintrust may be adversely affected by interest rate changes.
     Wintrust’s interest income and interest expense are affected by general economic conditions and by the policies of regulatory authorities, including the monetary policies of the Federal Reserve. Changes in interest rates may influence the growth rate of loans and deposits, the quality of the loan portfolio, loan and deposit pricing, the volume of loan originations in Wintrust'sWintrust’s mortgage banking business and the value that Wintrust can recognize on the sale of mortgage loans in the secondary market. Wintrust expects the results of its mortgage banking business in selling loans into the secondary market will be impacted during periods of rising interest rates. While Wintrust has taken measures intended to manage the risks of operating in a changing interest rate environment, there can be no assurance that such measures will be effective in avoiding undue interest rate risk. If market interest rates should move contrary to Wintrust's "gap"Wintrust’s “gap” position on interest earning assets and interest-bearing liabilities, the "gap"“gap” will work against it and Wintrust'sWintrust’s net interest income may be negatively affected. The success of Wintrust's covered call option program, which Wintrust has used in effect to hedge its interest rate risk, may also be affected by changes in interest rates.
     With the decline inrelatively low interest rates that prevailed over the last three years, to historically low levels, Wintrust has been able to augment the total return of its investment securities portfolio by selling put options and call options on fixed-income securities it owns. Wintrust recorded fee income of $7.9approximately $11.4 million during 2003,2005, compared to $6.0approximately $11.1 million in 2002,2004, from premiums earned on these covered call option transactions. During the first six months of 2004, Wintrust recorded fee income of $4.6 million on these transactions. In a rising interest rate environment, particularly if the yield curve remains steep,interest rates continue to increase, the amount of premium income Wintrust earns on these transactions will likely decline. Wintrust'sWintrust’s opportunities to sell covered call options may be limited in the future if rates continue to rise. WINTRUST'S SHAREHOLDER RIGHTS PLAN AND PROVISIONS IN ITS ARTICLES OF INCORPORATION AND BY-LAWS MAY DELAY OR PREVENT AN ACQUISITION OF WINTRUST BY A THIRD PARTY. Wintrust's board
Provisions in Wintrust’s articles of directors has implementedincorporation and by-laws may delay or prevent an acquisition of Wintrust by a shareholder rights plan. The rights, which are attached to Wintrust's shares and trade together with its common stock, have certain anti-takeover effects. The plan may discourage or make it more difficult for another party to complete a merger or tender offer for Wintrust's shares without negotiating with Wintrust's board of directors or to launch a proxy contest or to acquire control of a larger block of Wintrust's shares. If triggered, the rights will cause substantial dilution to a person or group that attempts to acquire Wintrust without approval of its board of directors and, under certain circumstances, the rights beneficially owned by the person or group may become void. The plan also may have the effect of limiting shareholder participation in certain transactions such as mergers or tender offers whether or not such transactions are favored by Wintrust's incumbent directors and key management. In addition, Wintrust's executive officers may be more likely to retain their positions with the company as a result of the plan, even if their removal would be beneficial to shareholders generally. Wintrust'sthird party.
     Wintrust’s articles of incorporation and by-laws contain provisions, including a staggered board provision, that make it more difficult for a third party to gain control or acquire Wintrust without the consent of its board of directors. These provisions also could discourage proxy contests and may make it more difficult for dissident shareholders to elect representatives as directors and take other corporate actions. These provisions of Wintrust'sWintrust’s governing documents may have the effect of delaying, deferring or preventing a transaction or a change in control that might be in the best interest of Wintrust'sWintrust’s shareholders. CAUTION ABOUT

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FORWARD-LOOKING STATEMENTS Certain
     We have made forward-looking statements contained in this document,proxy statement/prospectus, including informationin the documents incorporated into this documentproxy statement/prospectus by reference, that are not historical facts may constitutesubject to risks and uncertainties. These statements are based upon current expectations of each company’s management. Generally, forward-looking statements withininclude information concerning possible or assumed future actions, events or results of operations of Wintrust and the meaningcombined company. Forward-looking statements include the information in this proxy statement/prospectus regarding:
management forecasts, projections and estimates;
efficiencies and cost savings;
business and growth strategies (including anticipated internal growth, plans to form additionalde novobanks and to open new branch offices, and to pursue additional potential development or acquisition of banks, wealth management entities, specialty finance business or fee-related businesses);
regulatory matters;
combined operations;
the economy;
future economic performance;
conditions to, and the timetable for, completing the merger;
future acquisitions or dispositions;
litigation;
potential and contingent liabilities;
management’s plans;
taxes; and
merger and integration expenses.
     Forward-looking statements may be preceded by, followed by or include the words “may,” “will,” “should,” “could,” “would,” “plan,” “potential,” “possible,” “hope,” “estimate,” “project,” “believe,” “intend,” “anticipate,” “expect,” “target” and similar expressions. We claim the protection of Section 27A of the Securities Act of 1933, as amended, or the Securities Act, and Section 21E of the Securities Exchange Act of 1934, as amended, or the Securities Exchange Act, and are intended to be covered by the safe harbor provisions offor forward-looking statements contained in the Private Securities Litigation Reform Act of 1995. The sections of this document which containfor 1995 for all forward-looking statements include, but are not limited to, "Questions and answers about the merger," "Summary," "Risk Factors," "Description of the merger--Background of the merger," "Description of the merger--Wintrust's reasons for the merger" and "Description of the merger--Town Bankshares' reasons for the merger and recommendation of the board of directors." You can identify these statements from our use of the words "may," "will," "should," "could," 17 "would," "plan," "potential," "estimate," "project," "believe," "intend," "anticipate," "expect," "target" and similar expressions.statements.
     These forward-looking statements include statements relating to: o Wintrust's goals, intentions and expectations; o Wintrust's business plans and growth strategies; and o estimates of Wintrust's risks and future costs and benefits. These forward-looking statements are subject toinvolve significant risks, assumptions and uncertainties, and could be affected by many factors including, among other things, changes in general economic and business conditions and the risks and other factors set forth in the "Risk Factors"“Risk Factors” section beginning on page 15 as well as changes in economic conditions, competition, or other factors that may influence the anticipated growth rate of loans17, and deposits, slower than anticipated development and growth of Tricom and the trust and investment business, unanticipated changes in the temporary staffing industry, the ability to adapt successfully to technological changes to compete effectively in the marketplace, competition and the related pricing of brokerage and asset management products and Wintrust's ability to pursue acquisitions and expansion.documents that are incorporated by reference into this proxy statement/prospectus. Because of these and other uncertainties, Wintrust'sWintrust’s actual future results, performance or achievements, or industry results, may be materially different from the results indicated by these forward-looking statements. In addition, Wintrust'sWintrust’s past results of operations do not necessarily indicate Wintrust'sWintrust’s future results. You should not place undue reliance on any forward-looking statements, which speak only as of the dates on which they were made. Wintrust is not undertaking an obligation to update these forward-looking statements, even though its situation may change in the future, except as required under federal securities law. Wintrust qualifies all of its forward-looking statements by these cautionary statements. Further information on other factors which could affect the financial results of Wintrust before and after the merger is included in Wintrust's filings with the SEC, incorporated by reference into this proxy statement/prospectus. See "Where You Can Find More Information" on page 54. 18

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INFORMATION ABOUT THE SPECIAL MEETING OF TOWN BANKSHARESHINSBROOK SHAREHOLDERS DATE, PLACE, TIME AND PURPOSE Wintrust's and Town Bankshares' boards
     Hinsbrook’s board of directors are sending youis using this proxy statement/prospectus and proxy form to solicit proxies from the holders of Hinsbrook common stock for use at the special meeting.meeting of Hinsbrook’s shareholders.
Date, time and place of the special meeting
     The special meeting will be held at the main office of Hinsbrook Bank & Trust located at 6262 South Route 83, Willowbrook, Illinois 60527 on May 30, 2006 at 4:00 p.m., local time.
Purpose of the special meeting
     At the special meeting, the Town BanksharesHinsbrook board of directors will ask you to vote on a proposal to approveupon the merger agreement. Town Banksharesfollowing:
a proposal to approve the merger agreement and thereby approve the merger;
a proposal to approve an adjournment of the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to approve the merger agreement and the transactions it contemplates; and
any other business that properly comes before the special meeting and any adjournment or postponement thereof.
Record date and Wintrust will share equally the costs associated with the solicitation of proxiesvoting rights for the special meeting. The special meeting will be held at ________________________________________, on ____________ ___, 2004 at _______, local time. RECORD DATE, VOTING RIGHTS, QUORUM AND REQUIRED VOTE Town Bankshares
     Hinsbrook has set the close of business on __________ ___, 2004,April 24, 2006, as the record date for determining the holders of its common stock entitled to notice of and to vote at the special meeting. Only Town BanksharesHinsbrook shareholders at the close of business on the record date are entitled to notice of and to vote at the special meeting. As of the record date, there were __________2,761,723 shares of Town BanksharesHinsbrook common stock outstanding and entitled to vote at the special meeting. There must be
Quorum and abstentions required vote
     The presence in person or by proxy of at least a majority of Town Bankshares'Hinsbrook’s outstanding shares present in person or by proxy at the special meeting is required in order for the vote on the merger to occur. Abstentions from voting or any failure to vote will have the same effect as voting against the merger agreement.
Vote required
Approval of (1) the merger agreement will requireproposal, (2) the proposal to adjourn the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to approve the merger agreement and the transactions it contemplates and (3) any other business that properly comes before the special meeting and any adjournment or postponement thereof, each requires the affirmative vote of at least a majority of Town Bankshares'Hinsbrook’s outstanding shares.shares entitled to vote.
Shares held by Hinsbrook officers and directors; voting agreements
     Certain shareholdersofficers and directors of Town Bankshares,Hinsbrook, including one officer who has since resigned, whose aggregate ownership represents approximately 16.9%39.4% of Town Bankshares'Hinsbrook’s outstanding shares, have committed to vote their shares in favor of the merger. Wintrust does not own any shares of Town BanksharesHinsbrook common stock. See "Description of the merger--Voting agreement"“The merger—Voting agreement” on page 3641 for a description of the provisions of the voting agreement. Abstentions from voting or any failure
How to vote will have the same effect as voting against the merger agreement. VOTING AND REVOCABILITY OF PROXIES
     You may vote in person at the special meeting or by proxy. To ensure your representation at the special meeting, we recommend you vote by proxy even if you plan to attend the special meeting. You can always change your vote at the meeting.

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     Voting instructions are included on your proxy form.form, which should be returned in the enclosed prepaid envelope. If you properly complete and timely submit your proxy, your shares will be voted as you have directed. You may vote for, against, or abstain with respect to the approval of the merger.merger and the other proposals. If you are the record holder of your shares and submit your proxy without specifying a voting instruction, your shares will be voted "FOR"as the Hinsbrook board of directors recommends and will be voted“FOR” approval of the merger agreement.agreement and“FOR” the adjournment of the special meeting to permit further solicitation in the event that an insufficient number of shares are present in person or by proxy to approve the merger agreement and the transactions it contemplates.
     In addition to your proxy form, you have received a separate election form for use in electing the merger consideration you will receive in the merger. The election form should be completed and returned to Illinois Stock Transfer Company in the enclosed prepaid envelope.
Revocability of proxies
     You may revoke your proxy at any time before it is voted by: o filing with Town Bankshares' secretary a duly executed revocation of proxy; o submitting a new proxy with a later date; or o
filing with Hinsbrook’s secretary a duly executed revocation of proxy;
submitting a new proxy with a later date; or
voting in person at the special meeting.
     Attendance at the special meeting will not, in and of itself, constitute a revocation of a proxy. All written notices of revocation and other communication with respect to the revocation of proxies should be addressed to: Town Bankshares, Ltd.Hinsbrook Bancshares, Inc., 400 Genesse Street, Delafield, Wisconsin 53018,6262 South Route 83, Willowbrook, Illinois 60527, Attention: Secretary. VOTING RIGHTS OF PARTICIPANTS IN THE ESOP As
Proxy solicitation
     In addition to this mailing, proxies may be solicited by directors, officers or employees of ___________, 2004,Hinsbrook in person or by telephone or electronic transmission. None of such directors, officers or employees will be directly compensated for such services. Hinsbrook has retained Illinois Stock Transfer Company to assist in the record datedistribution and solicitation of proxies. Illinois Stock Transfer Company will be paid a fee of approximately $750, plus reasonable expenses, for these services. Hinsbrook and Wintrust will share equally the costs associated with the solicitation of proxies for the special meeting.
Other business; adjournments
     Hinsbrook is not currently aware of any other business to be acted upon at the Hinsbrook special meeting. If, however, other matters are properly brought before the special meeting, or any adjournment or postponement thereof, your proxies include discretionary authority on the ESOP owned 7,700part of the individuals appointed to vote your shares to act on those matters according to their best judgment.
     Adjournments may be made for the purpose of, Town Banksharesamong other things, soliciting additional proxies. Any adjournment may be made from time to time by the affirmative vote of the majority of the votes cast by holders of Hinsbrook common stock including 1,449 shares allocatedpresent in person or by proxy at the special meeting, whether or not a quorum is present, without further notice other than by announcement at the special meeting. Hinsbrook does not currently intend to participants' accounts. Eligible ESOP participants are being offered the opportunity to direct the ESOP administrator, who will in turn direct the ESOP trustees, as to whether to vote such participants' allocated shares of common stock for or against the merger. The ESOP is 19 administered by Town Bankshares. The trusteesseek an adjournment of the ESOP are Jay C. Mack, Jeffrey A. Olsen, Randall R. Tiedt and Dennis Haefer. To direct the ESOP administrator, an ESOP participant should complete the "Direction to ESOP Administrator" Form (the "Direction Form") that accompanies this proxy statement/prospectus and return it to the ESOP administrator (c/o The Pension Specialists, Ltd., Attention: Jean Southworth, P.O. Box 4247, Rockford,special meeting.
Dissenters’ rights
     Under Illinois 61110-0747), all in accordance with the instructions set forth below. Each participant in the ESOP whose account contains shares of Town Bankshares common stock as of the record date is eligible to vote by completing, signing and timely returning the Direction Form to the ESOP administrator. These individuals include employees of Town Bankshares as of the record date who have shares allocated in their ESOP accounts as well as former employees of Town Bankshares who have not received a final distribution from the ESOP. ESOP participants may direct the ESOP administrator to vote their allocated shares of Town Bankshares common stock for or against the merger. Under the terms of the ESOP, subject to the fiduciary obligations described below, the ESOP administrator will direct the ESOP trustees to vote the common stock allocated to participant accounts as directed by participants. The voting rights of such common stock will be exercised only to the extent directed by the participant, unless the ESOP trustees determine that their fiduciary obligations require them to vote any common stock for which no directions are received. Any fractional share of common stock allocated to participants' accounts will be combined with fractional shares in other participants' accounts to be voted to reflect, to the extent the ESOP administrator deems it possible, the directions of the participants with fractional shares in their accounts. The voting directions with respect to the common stock of all participants will be communicated by the ESOP administrator to the ESOP trustee for voting in accordance therewith. The voting rights of any common stock held unallocated by the ESOP will be voted as directed by the ESOP administrator in a manner it determines to be in the best interests of participants. As of the record date, 1,449 shares of Town Bankshares common stock held by the ESOP were allocated to ESOP participant accounts, and 6,251 shares were unallocated. The ESOP trustees and administrator are subject to certain fiduciary obligations imposed by the Employee Retirement Income Security Act of 1974. In general, the ESOP trustees and administrator are obligated under the ESOP to follow the ESOP participants' directions with respect to the vote, to the extent described above, unless the ESOP trustees or the administrator independently determines that to do so would be imprudent or contrary to the best interests of ESOP participants. Therefore, it could be possible that, notwithstanding the outcome of the ESOP participants' instructions, the ESOP trustees or administrator could, in the exercise of their fiduciary obligations, decide to vote all the ESOP shares in favor of or against the merger. An ESOP participant who wishes to vote his or her allocated shares of Town Bankshares common stock must properly complete and timely return the Direction Form. To do so, after reading this proxy statement/prospectus, an ESOP participant should: o mark, date and sign the Direction Form. o mail the Direction Form so that it will be received by the ESOP administrator, c/o The Pension Specialists, Ltd., Attention: Jean Southworth, P.O. Box 4247, Rockford, Illinois 61110-0747, no later than __________, 2004. In order to be effective, a Direction Form must be received by the administrator no later than __________, 2004. If an ESOP participant fails to sign or timely return a Direction Form, the ESOP administrator will consider the shares of Town Bankshares common stock represented by such Direction Form to be shares with respect to which no instruction has been submitted. Therefore, if an ESOP participant does not want the ESOP administrator to consider his or her allocated shares as shares with respect to which no instruction has been submitted, the ESOP participant must specifically mark a box on the Direction Form, sign the Direction Form and return it to the ESOP administrator so that the ESOP administrator receives it no later than ________, 2004. An ESOP participant who decides to change his or her vote after having submitted a Direction Form must obtain a new Direction Form by contacting the ESOP administrator. By properly completing and timely returning a new Direction Form, an ESOP participant's previously submitted Direction Form will be revoked automatically. The ESOP administrator may be reached at the following address: 20 c/o The Pension Specialists, Ltd. Attention: Jean Southworth P.O. Box 4247 Rockford, Illinois 61110-0747 An ESOP participant may also revoke a Direction Form by notifying the ESOP administrator in writing of the ESOP participant's direction to revoke, but if a new Direction Form is not timely received by the ESOP administrator, the ESOP participant's allocated shares covered by the revoked Direction Form will be considered by the ESOP administrator to be shares with respect to which no instruction has been submitted. After _________, 2004, no Direction Form will be accepted and no Direction Form will be permitted to be changed or revoked. Each Direction Form received by The Pension Specialists, Ltd. will be held in confidence and will not be released or divulged to representatives of Town Bankshares. Any participant in the ESOP should contact the ESOP trustees or administrator if he or she has been subject to pressure or coercion by any party or if he or she is concerned about the confidentiality of instructions submitted to The Pension Specialists, Ltd. DISSENTERS' RIGHTS Under Wisconsin law, Town Bankshares shareholdersyou are entitled to exercise dissenters'dissenters’ rights and obtain a cash payment for theirthe “fair value” of your shares of Town Bankshares common stock as a result of Wintrust'sWintrust’s acquisition of Town Bankshares,Hinsbrook, provided that such shareholdersyou comply with the applicable provisions of Sections 180.1301 through 180.133111.65 and 11.70 of the Wisconsin Business Corporation Law, or the WBCL. Neither the ESOP nor its participants will have dissenters' rights because all of the shares in the ESOP will be redeemed for cash prior to the completion of the merger. AIBCA. The following is a brief summary of those sectionsthe statutory procedures that you must follow in order to perfect your dissenters’ rights under Illinois law.This summary is set forth belownot a complete statement of the law pertaining to dissenters’ rights under the IBCA and is qualified in its entirety by reference to Sections 11.65 and 11.70 of the IBCA, a copy of themwhich is attachedincluded asAnnex C and incorporated inBto this proxy statement/prospectus by reference. If you comply withprospectus.

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     Shareholders of Hinsbrook who follow the applicable provisions of Sections 180.1301 through 180.1331procedures set forth in Section 11.70 of the WBCL, then, uponIBCA will be entitled to dissent from the merger and to obtain payment, after the merger, for the “fair value” of their shares, if any, calculated immediately before the consummation of the merger, you willexclusive of any appreciation or depreciation in anticipation of the merger, unless such exclusion would be entitled to receive payment from Wintrust for the "fair value" of your shares, with accrued interest. If Wintrust and you cannot agree on the inequitable (“fair value of your shares or thevalue”), plus accrued interest thenfrom the WBCL provides for a judicial determination of these amounts. The fair value determined by a Wisconsin court could be more or less than the value of the consideration that you are entitled to receive under the merger agreement. If you desire to exercise dissenters' rights, you should refer to the applicable provisions of the WBCL in their entirety and consult with legal counsel before taking any action to ensure that you comply strictly with the WBCL. In summary, to exercise dissenters' rights you must initially do the following: o before the vote to approvetime the merger is held, delivereffective until the date of payment, at the average interest rate currently paid by Wintrust on its principal bank loans, or if none, at a rate that is fair and equitable under the circumstances (the “interest”).
     A record owner may assert dissenters’ rights as to Town Bankshares afewer than all the shares recorded in such person’s name only if such person dissents with respect to all shares beneficially owned by any one person and notifies Wintrust in writing of the name and address of each persons on whose behalf the record owner asserts such rights. A beneficial owner of shares who is not the record owner may assert dissenters’ rights only if the beneficial owner submits to Wintrust the record owner’s written notice of your intentconsent to dissent before or at the same time the beneficial owner asserts dissenters’ rights.
     To dissent from the merger and demand payment ofappraisal, you must satisfy the fair value of your shares of Town Bankshares; and o not vote your shares of Town Bankshares common stock in favor of the merger.following conditions:
deliver a written demand for appraisal of your shares to Hinsbrook before the vote on the approval of the merger agreement at the special meeting (voting against the merger agreement will not satisfy this requirement);
not vote in favor of the merger agreement (if you return your signed proxy and do not specify a vote against the merger agreement or a direction to abstain, your shares will be voted in favor of the merger agreement and you will waive your right to dissent); and
continuously hold your Hinsbrook shares from the date of making the demand through the time the merger is completed.
     Your failure to vote against the proposal to adoptapprove the merger agreement will not constitute a waiver of your dissenters'dissenters’ rights under the WBCL. Additionally,IBCA. Also, a vote in person or by proxy, against approval of the merger agreement will not by itself be sufficient to satisfy your obligations if you are seeking to exercise dissenters' rights.an appraisal. You must follow each of the procedures of Sections 180.1301 through 180.1331sent forth in Section 11.70 of the WBCLIBCA to obtain dissenters'perfect dissenters’ rights. Each outstanding share of Town Bankshares common stock for whichIf you fail to so comply with these procedures and the merger becomes effective, you will receive the consideration provided in the merger agreement.
     If you make a legally sufficient demand, in accordance with the WBCL and which you do not vote in favor of approval of the merger will, after the effective time of the merger, represent only the rights of a dissenting shareholder under the WBCL. This includes the right to obtain payment for the estimated fair value of those as provided under the WBCL. If shareholders of Town Bankshares approve the merger and you make a legally sufficient demand, then Wintrust will send you, within 10 days of approval of the merger, a written dissenters' notice to be used to demand payment for your shares of Town Bankshares common stock. The dissenters' notice will: o supply a form for demanding payment that includes the date of the first announcement of the merger and requires each shareholder asserting dissenters' rights to certify whether he or she acquired beneficial ownership of the shares before that date; 21 o include a statement indicating where shareholders should send the payment demand and when and where certificated shares must deposited; o include, for holders of uncertificated shares, an explanation of the extent to which transfer of the shares will be restricted after the payment demand is received; o set a date by which Wintrust must receive your payment demand, which must be no fewer than 30 and no more than 60 days after the date on which the dissenters' rights noticemerger is delivered; and o be accompanied by a copy of Sections 180.1301 through 180.1331 of the WBCL. Upon receipt ofeffective or 30 days after you deliver the written dissenters' notice, if you still wish to exercise your dissenters' rights, you must: o demand for payment, in writing and certify that you acquired your shares of Town Bankshares common stock before the date specified in the dissenters' notice; and o deposit any certificated shares in accordance with the terms of the written dissenters' notice. At the effective time of the merger or upon receipt of a payment demand, whichever is later, Wintrust will pay each dissenting shareholder who has complied with the applicable provisions of the WBCL the amount which Wintrust estimates to be the fair value of his or her shares of Town Bankshares common stock, plus accrued interest. The payment will be accompanied by: o Town Bankshares' and Wintrust's latest available audited financial statements, including footnotes and the latest available interim financial statements; o a statement of Wintrust's estimate of the fair value of the shares of Town Bankshares common stock; o an explanation of how interest was calculated; o a statement of a dissenting shareholder's right to demand payment under Section 180.1328 of the WBCL, ifmust send you:
a statement setting forth its opinion of the fair value of the shares;
Hinsbrook’s latest balance sheet as of the end of a fiscal year ending not earlier than 16 months before delivery of the statement, together with the statement of income for that year;
the latest available interim financial statements; and
a commitment to pay for the shares held by the dissenting shareholder at the estimated fair value upon the transmittal to Wintrust of the certificate(s), or other evidence of ownership.
     If the dissenting shareholder is dissatisfied with the payment; and o a copy of Sections 180.1301 through 180.1331 of the WBCL. Under Section 180.1328 of the WBCL, you may send Wintrust your own estimate of the fair value of your shares and the amount of any interest due and demand payment of the difference between your estimate and the amount Wintrust paid you, if any, in the following cases: o if you believe that the amount Wintrust paid you is less than the fair value of your shares or that the interest due is incorrectly calculated; o if you fail to receive payment within 60 days after the date set forth in the dissenters' notice for demanding payment; or o if the merger is not consummated, and Town Bankshares does not return deposited certificates or release any transfer restrictions imposed on uncertificated shares within 60 days afteragree with Wintrust as to the date set forth in the dissenters' notice for demanding payment. Within 30 days of receiving payment or the initial offer to pay, you must demand payment of the difference between your estimate of the fair value of your shares, plus interest, and the amount paid to you, or you will lose your rights to demand payment of any such difference. Under Section 180.1330 of the WBCL, if an agreement cannot be reached on theestimated fair value of the shares or the amount of interest due, thensuch shareholder may, within 30 days from the delivery of Wintrust’s statement of value, notify Wintrust of such shareholder’s estimated fair value and amount of interest due. Such notice must commence a proceeding in courtdemand payment for the difference between such shareholder’s estimate of fair value and interest and the amount of payment offered by Wintrust. If within 60 days after receiptfrom delivery of your demand for payment,the dissenting shareholder’s notification of estimated fair value and interest due, no written agreement has been reached, Wintrust must either pay the difference in value demanded by the dissenting shareholder with interest or file a petition in the circuit court of Lake County, Illinois, requesting the court to determine the fair value of yourthe shares and accrued interest. If 22 interest due. Wintrust does not commence this proceeding within sixty days, then it must pay you the unsettled amount that you demand. If Wintrust commences this proceeding, then it will make all dissenting shareholders whosedissenters with unsettled demands remain unsettled (even if they are not resident of Wisconsin) parties to the proceeding as an action against their shares, and shall serve all such parties will be served with a copy of the petition. If Wintrust fails to commence an action in circuit court, the dissenting shareholders may commence an action as permitted by law. The court mayhas power to appoint appraisersone or more appraisers. Each dissenter

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who is a party to such action is entitled to receive evidence and recommend a decision on the question of fair value. Ifamount, if any, by which the court finds that the amount paid to you is less than the fair value of a dissenting holder'shis or her shares, plus accrued interest, exceeds the amount paid by Wintrust.
     In a proceeding brought by Wintrust to determine fair value, the court will order Wintrust to paydetermine the difference to the dissenting shareholder. The court will determine all costs of the appraisal proceeding, including the reasonable compensation of expenses of the appraisers appointed by the court and excluding fees and expenses of court-appointed appraisers,counsel and assessexperts for the respective parties. If the fair value of the shares, as determined by the court, materially exceeds the price that Wintrust estimated to be the fair value of the shares or, if no estimate was given, then all or any part of the costs may be assessed against Wintrust. However,If the amount that any dissenter estimated to be the fair value of the shares materially exceeds the fair value of the shares, as determined by the court, may order somethen all or allany part of the dissenting shareholderscosts may be assessed against that dissenter. The costs may be awarded to pay some of these costs, in amounts that the court finds equitable,dissenter if the court finds that Wintrust did not substantially comply with the dissentersprocedures in the statute. In addition, costs can be assessed against either party if the court finds that that party acted arbitrarily vexatiously or not in good faith with respect to the dissenter’s rights.
     Shareholders of Hinsbrook who are considering seeking an appraisal should bear in demanding paymentmind that the fair value of their Hinsbrook shares as determined under Section 180.132811.70 of the WBCL.IBCA could be more than, the same as, or less than the merger consideration they are to receive pursuant to the merger agreement if they do not seek appraisal of their shares.
     All written demands for appraisal should be addressed to: Hinsbrook Bancshares, Inc., 6262 South Route 83, Willowbrook, Illinois 60527, Attention: President and Chief Executive Officer. A demand must be received before the vote concerning the merger agreement at the special meeting occurs, and should be executed by, or on behalf of, the holder of record.
     If you give notice ofproperly exercise your intentdissenters’ rights and follow the correct procedures in the IBCA, your Hinsbrook shares will not be converted into, or represent, a right to demand dissenters'receive the consideration provided for in the merger agreement and you will not be entitled to vote or receive any dividends or other distributions on any such shares. If, however, you fail to properly perfect, effectively withdraw, waive, lose, or otherwise become ineligible to exercise dissenting shareholder’s rights for your shares under the applicable provisions ofIBCA, then at such time, the WBCL but fail to return your payment demand or withdraw or lose your rights to demand payment, each of your shares of Town Bankshares common stockheld by you will be converted into the right to receive shares of Wintrust common stock and cashconsideration provided in the amountmerger agreement.
     Failure to comply strictly with these procedures will cause you to lose your dissenters’ rights. Consequently, if you desire to exercise your dissenters’ rights you are urged to consult a legal advisor before attempting to exercise these rights.
THE MERGER
This section of $58.10 in accordance with the proxy statement/prospectus describes material aspects of the merger. While Wintrust and Hinsbrook believe that the description covers the material terms of the merger agreement. DESCRIPTION OF THE MERGER The followingand the related transactions, this summary may not contain all of the information describes certain aspectsthat is important to you. You should carefully read this entire proxy statement/prospectus, the attached Annexes, and the other documents to which this proxy statement/prospectus refers for a more complete understanding of the merger. The agreement and plan of merger, agreement,not this summary, is the legal document which you should read carefully,governs the merger.
General
     The Hinsbrook board of directors is attached as Annex A tousing this proxy statement/prospectus to solicit proxies from the holders of Hinsbrook common stock for use at the Hinsbrook special meeting, at which Hinsbrook shareholders will be asked to vote on approval of the merger agreement and incorporated herein by reference. GENERALthereby approve the merger. When the merger is consummated, Town BanksharesHinsbrook will merge with and into Wintrust and will cease to exist. Wintrust will survive the merger and TownHinsbrook Bank & Trust will become a wholly-owned subsidiary of Wintrust. At the effective time of the merger, holders of Town BanksharesHinsbrook common stock will exchange their shares for cash, shares of Wintrust common stock or a combination of 50% cash and cash.50% of shares of Wintrust common stock, in each case subject to proration. Each share of Town BanksharesHinsbrook common stock will be exchanged for a numberthe “per share merger consideration” the stock component of Wintrust shares equal to the "per share stock consideration" which cannot be determined until twofour trading days before completion of the merger and cash in the amount of $58.10.merger. See "Description“Description of the merger agreement--Considerationagreement—Consideration to be received in the merger"merger” for a detailed description of the method for determining the per share stockmerger consideration.

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     Only whole shares of Wintrust common stock will be issued in the merger. As a result, cash will be paid instead of any fractional shares based on the average of the high and low salesreference price of Wintrust'sWintrust’s common stock during the 10-day trading period ending two trading days before the merger is completed.reference period. Shares of Town BanksharesHinsbrook common stock held by Town BanksharesHinsbrook shareholders who elect to exercise their dissenters'dissenters’ rights will not be converted into cash, Wintrust common stock or the combination of cash and cash. THE COMPANIES Business of Wintrust--GeneralWintrust common stock.
The Companies
Wintrust
     Wintrust Financial Corporation, an Illinois corporation, is a financial holding company headquartered in Lake Forest, Illinois. As of December 31, 2005, Wintrust operates tenoperated 13 community banks, all located in the greater Chicago and Milwaukee metropolitan area,areas, which provide community-oriented, personal and commercial banking services primarily to individuals and small to mid-size businesses through 4262 banking facilities asfacilities. Wintrust, through various of June 30, 2004. Wintrustits subsidiaries, also provides wealth management services, through itsincluding trust, company, investment adviserasset management and broker-dealer subsidiariesbrokerage services, to customers located primarily in the Midwest, as well as to customers of its banks. Wintrust also originates and purchases residential mortgage loans, many of which are sold into the secondary market. In addition, Wintrust is involved in specialty lending through a number of operating subsidiaries or divisions of certain of its banks. Its specialty lending niches include commercial insurance premium finance, accounts receivable financing and administrative services to the temporary staffing industry and indirect auto lending in which Wintrust purchases loans through Chicago-area automobile dealerships. 23 As of June 30, 2004,December 31, 2005, Wintrust had consolidated total assets of $5.33$8.17 billion, deposits of $4.32$6.73 billion and shareholders'stockholders’ equity of $374.2$628 million. Wintrust’s common stock trades on the Nasdaq National Market under the symbol “WTFC.”
     Financial and other information relating to Wintrust, including information relating to Wintrust'sWintrust’s current directors and executive officers, is set forth in Wintrust's 2003Wintrust’s 2005 Annual Report on Form 10-K, Wintrust'sWintrust’s Proxy Statement for its 20042006 Annual Meeting of Shareholders filed with the SEC on April 23, 2004, Wintrust's Quarterly Reports on Form 10-Q for each of the quarters ended March 31, 200424, 2006 and June 30, 2004 and Wintrust'sWintrust’s Current Reports on Form 8-K filed during 2004,2006, which are incorporated by reference to this proxy statement/prospectus. Copies of these documents may be obtained from Wintrust as indicated under "Where“Where You Can Find More Information"Information” on page 54.61. See "Incorporation“Incorporation of Certain Information by Reference"Reference” on page 54. Business of Wintrust--Recent Developments On May 10, 2004, Wintrust announced the signing of a definitive agreement to acquire Northview Financial Corporation, or Northview, in a merger transaction. Northview is the parent company of Northview Bank and Trust, or Northview Bank, which has locations in Northfield, Mundelein and Wheaton, Illinois. Northview Bank began operations as a de novo bank in 1993, and Northfield had total assets of approximately $343.9 million as of June 30, 2004. In the proposed merger, each share of Northview's outstanding common stock will be converted into the right to receive cash and a number of shares of Wintrust's common stock to be determined based on Wintrust's average trading price at closing determined in accordance with the definitive merger agreement. The aggregate per share consideration equates to approximately $275, subject to possible adjustment depending on Wintrust's average trading price at closing. At June 30, 2004, Northview had outstanding 164,730 shares of common stock and in-the-money options to acquire approximately 10,850 shares of common stock at exercise prices ranging from $75.00 to $115.00 per share, with a weighted average exercise price of approximately $98.53. The merger is expected to close late in the third quarter of 2004 and is not expected to have a material effect on Wintrust's 2004 earnings per share. Business of Town Bankshares Town Bankshares, Ltd.61.
Hinsbrook
     Hinsbrook Bancshares, Inc., a Wisconsinan Illinois corporation, is a bank holding company headquartered in Delafield, Wisconsin.Willowbrook, Illinois. Its primary business is operating its bank subsidiary, TownHinsbrook Bank a Wisconsin& Trust, an Illinois state bank, with officesIllinois branch locations in DelafieldWillowbrook, Downers Grove, Darien, Glen Ellyn and Madison, Wisconsin. In addition to TownGeneva. Hinsbrook Bank Town Bankshares conducts limited business activities through Town Investment Corp., a Nevada corporation. We sometimes refer to Town Bank and Town Investment Corp. as the "subsidiaries."& Trust began operations in 1987. As of June 30, 2004, Town BanksharesDecember 31, 2005, Hinsbrook had consolidated total assets of approximately $238.0$500.0 million, deposits of $204.3$430.6 million and shareholders'shareholders’ equity of $17.8$41.4 million. BACKGROUND OF THE MERGER Town Bankshares has regularly conductedHinsbrook is not a strategic planning process each year inpublic company and, accordingly, there is no established trading market for Hinsbrook’s common stock.
Hinsbrook’s proposal
     At the summer. As it commenced this process inHinsbrook special meeting, holders of shares of Hinsbrook common stock will be asked to vote on the summer of 2003, Town Bankshares recognized that it was faced with a number of strategic challenges that resulted from its rapid growth rate. These challenges included: (1) keeping its capital base growing as rapidly as its assets were growing, (2) generating core deposit growth to keep up with its loan growth, (3) pursuing new lending business with a legal lending limit below what was desirable in the marketplace, and (4) pursuing new private banking business with a limited portfolio of product and service offerings. On June 12, 2003, Town Bankshares retained Corporate Financial Advisors, LLC, or CFA, to review its strategic alternatives to respond to these challenges as partapproval of the strategic planning process. At a meetingmerger agreement and thereby approve the merger.The merger will not be completed unless Hinsbrook’s shareholders approve the merger agreement and thereby approve the merger.
Background of Town Bankshares'the merger
     Hinsbrook’s board of directors held on July 31, 2003, CFA presentedand senior management regularly review and evaluate Hinsbrook’s business, strategic direction, performance, prospects and strategic alternatives. This review and evaluation included regular consultation with Hinsbrook’s financial consultants, Young & Associates, Inc. In early 2005, Hinsbrook began such a numberreview. As part of this review, Hinsbrook discussed the advantages and disadvantages of remaining an independent operating concern, the historical performance and strategic alternativesdirection of Hinsbrook Bank & Trust and the lack of liquidity for Hinsbrook’s shareholders. As part of this discussion, Hinsbrook considered the increasing

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amount of competition in Hinsbrook’s primary markets, anticipated costs and capital requirements necessary to fund Hinsbrook’s continued expansion, the manner in which Hinsbrook would continue to address loan concentration and funding challenges and trends in mergers and acquisitions in the financial services sector.
     Following this discussion, the board authorized management to investigate a strategic transaction, including a possible sale transaction. To that end, the board authorized management to contact financial advisors and legal counsel for assistance with this investigation. Hinsbrook retained Capital Market Securities, an affiliate of directors of Town Bankshares, and discussed the merits of each. These strategic alternatives included: (1) slowing Town Bankshares' growth rate to a level whereby its capital needs could be funded by earnings, (2) obtaining significant outside financing from an institutional investor to expand Town Bankshares' capital base to permit faster growth, (3) obtaining more limited financing from current shareholders or through a private placement of trust preferred securities, and (4) selling or merging Town Bankshares into a larger institution that could provide the resources to maximize its perceived opportunities. 24 The board of directors continued to discuss these strategic alternatives at meetings held on August 27, 2003 and September 17, 2003. Also, in August 2003, Town Bankshares solicited proposals from several investment banking firms and CFA to actYoung & Associates, Inc., as its financial advisor in connection with exploring its strategic alternatives and a possible sale transaction.
     Hinsbrook and Capital Market Securities signed a formal engagement letter on June 3, 2005. Also on that date, representatives of Capital Market Securities met with representatives of Hinsbrook’s management to assistdiscuss Hinsbrook’s strategic alternatives and provided a market analysis, which included an analysis of trends in exploringbank pricing and financial performance along with an analysis of bank merger activity. Capital Market Securities also discussed with Hinsbrook potential pricing Hinsbrook might anticipate should it decide to consider a possible sale transaction. Capital Market Securities began gathering information about Hinsbrook’s business operations and primary markets.
     Shortly after the June 3, 2005 meeting, Capital Market Securities began a more comprehensive due diligence review of Hinsbrook and Hinsbrook Bank & Trust, meeting with members of Hinsbrook’s management on June 16 and June 17, 2005 and began developing confidential marketing materials concerning Hinsbrook.
     At the regular meeting of Hinsbrook’s board held on July 26, 2005, the board continued its discussions concerning the evaluation of Hinsbrook’s strategic alternatives.alternatives and a possible sale transaction. A representative of Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP, Hinsbrook’s special counsel, attended this meeting and gave a presentation concerning Hinsbrook’s strategic alternatives as well as the fiduciary obligations of the board. Representatives of Capital Market Securities also attended this meeting and reviewed with the board a draft of the confidential marketing materials that had been developed and a proposed list of prospective bidders. Following this meeting, Hinsbrook’s management continued to work with Capital Market Securities on the development of the confidential marketing materials. Capital Market Securities began contacting prospective bidders and distributed confidentiality agreements to those bidders expressing an interest in a possible transaction with Hinsbrook.
     At the regular monthly meeting of Hinsbrook’s board held on August 17, 2005, the board ratified the retention of Capital Market Securities as Hinsbrook’s financial advisor and authorized Capital Market Securities to distribute the approved confidential marketing materials to potential bidders. After this meeting, Capital Market Securities provided copies of the confidential marketing materials to each party that had executed a confidentiality agreement, worked with other potential bidders to obtain executed confidentiality agreements to be able to provide them with the confidential marketing materials and continued working with potential strategic partners with the goal of receiving initial bids by September 8, 2005.
     At a special meeting of the Hinsbrook board on September 12, 2005, Capital Market Securities reviewed the results of the preliminary proposal solicitation process with Hinsbrook’s board. Capital Market Securities reported that it had contacted 26 prospective strategic partners, 20 of which had executed confidentiality agreements and received copies of the marketing materials. Of these parties, six presented Hinsbrook with written, non-binding expressions of interest for a proposed acquisition transaction, subject to due diligence and the negotiation of a definitive agreement. At the September 1712 meeting, Town Bankshares'Capital Market Securities and the board discussed the price range of directors decided to pursue a private placement of trust preferred securities and also to explore a possible saleeach of the company. Givensix proposals received, the interest rate environmentform of consideration offered, the reputation of each party, the strategic opportunity offered by each possible transaction and the need for capitalperceived ability of each party to support Town Bankshares' growth,consummate a transaction. Following this discussion, the board of directors believed it was advisable to complete the trust preferred offering in the near-term. Town Bankshares completed a private placement of $6 million of trust preferred securities in October 2003. At the same time, the board of directors also concluded that Town Bankshares should begin to solicit potential buyers to determine if any buyer would offer both a good strategic fit with Town Bankshares' operations and an attractive purchase price for its shareholders. On September 19, 2003, Town Bankshares formally engaged CFA as its financial advisor to begin a sale process for Town Bankshares and obtain indications of interest for its acquisition. In October 2003, Town Bankshares' board of directors determined to form a special committee of independent directors to create a small group to more effectively oversee the sale process. The special committee consisted ofauthorized three independent directors, William J. Hickmann, Michael J. Pretasky, Sr. and Robert N. Trunzo. Thomas A. Manthy, who is also an independent director, was appointed as an alternate member of the Special Committee and attended a number of meetings of the Special Committee. Over the next several weeks after the board's September 17 meeting, Town Bankshares, with the assistance of CFA, began the sale process, including the preparation of an offering memorandum, the development of a list of potential buyers and the organization of due diligence materials. After receiving advice from CFA and completing these steps, Town Bankshares decided to begin the process of contacting potential buyers on November 1, 2003. Between November 1, 2003 and February 15, 2004, CFA contacted or was contacted by a total of 141 potential buyers, principally consisting of bank holding companies in Wisconsin, Illinois, Minnesota, Indiana, Michigan and Iowa, concerning their possible interest in acquiring Town Bankshares. Of these 141 parties, 31 entered into confidentiality agreements with Town Bankshares and conducted preliminary due diligence regarding Town Bankshares. Between November 1, 2003 and December 15, 2003, Town Bankshares received indications of interest from 11 of these parties, with preliminary valuation ranges from $22.0 million to $38.4 million. These indications of interest were based only on preliminary due diligence. Wintrust's offer was at the upper end of these valuation ranges and, management and the special committee believed, offered a good fit with Town Bankshares' operations and management philosophy. At a meeting held on February 27, 2004, the special committee reviewed the indications of interest submitted by the potential buyers with CFA. At the conclusion of these discussions, the special committee determined that no more than five of the bidders, offered an adequate valuation, a good strategic fit with Town Bankshares and reasonable certainty to closing. The special committee authorized CFA to invite these five biddersincluding Wintrust, to conduct additionaloff-site due diligence. Duringdiligence concerning Hinsbrook in order to obtain final bids from each.
     Due diligence was conducted by each of the coursethree prospective strategic partners, including Wintrust, during the weeks of September 19 through October 3, 2005 with the expectation that final bids would be submitted to Hinsbrook on October 14, 2005. Throughout the due diligence and bidding process, Capital Market Securities remained in contact with the prospective strategic partners to assist in the due diligence process and negotiate the bidders discussed Town Bankshares' operations, capital structure, asset quality and loan portfolio, andterms of the final offers. Wintrust submitted a revised written, non-binding expression of interest on October 14, 2005, while the two other matters raised by their due diligence with CFA and representatives of Town Bankshares. The special committee also decided that it would solicit final bids after Town Bankshares' operating results for the quarter ending March 31, 2004, were available. In May 2004, the special committee invited the remaining biddersprospective strategic partners declined to submit final proposalsbids.

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     Hinsbrook’s board met with Capital Market Securities on October 18, 2005 to acquire Town Bankshares. At this time, two bidders submitted final proposals. Wintrust made areview Wintrust’s revised bid of $129.10approximately $41.59 per share resulting in an aggregate valuation in the $41.0 million range (including the conversioncomprised of Town Bankshares stock options into options to purchaseapproximately 50% cash and 50% shares of Wintrust common stock). The other final bidder's bid was for $110.12 per share, resulting in an aggregate valuation in the $35.0 million range (including the conversion of Town Bankshares' stock options into options to purchase shares of the other bidder's common stock). Both of these bids contemplated merger consideration divided into approximately equal amounts of cash andWintrust’s common stock. Unlike Wintrust, the other bidder's common stock was not actively traded onThis discussion included a public market, and therefore offered significantly less liquidity to Town Bankshares' shareholders. The board of directors met on May 13, 2004, to review the final bids. At this meeting, the board of directors also authorized the engagement of Reinhart Boerner Van Deuren s.c. as legal counsel, and representatives of legal counsel and CFA attended the meeting. CFA made a presentation to the board of directors at the meeting on the bidding process and the merits of the two final bids. Following a detailed review of the final bids, theWintrust’s financial information, Wintrust’s history of prior transactions, Wintrust’s community bank operating philosophy and stock performance history. Following this review, Hinsbrook’s board of directors authorized the special committee and Town Bankshares' legal counsel and financial advisorsdetermined to workpursue a transaction with 25 Wintrust to complete its final due diligence and to negotiate a definitive merger agreement based on its proposal. Representatives of Wintrust were contacted and requested to prepare a draft of the merger agreement for review and consideration by the special committee. The board of directors also authorized the special committee to engage an investment banking firm to deliver an opinion with respect to the fairness of the merger consideration to Town Bankshares' shareholders from a financial point of view. On June 3, 2004, Town Bankshares engaged Edelman & Co., Ltd. to deliver such an opinion. On May 20, 2004, Wintrust's legal counsel delivered a draft of the merger agreement to Town Bankshares and its legal counsel for review. On May 25, 2004, the members of the special committee met with Town Bankshares' legal counsel and a representative from CFA to review the draft merger agreement and the significant issues with Wintrust's draft. Legal counsel also reviewed with the special committee the fiduciary duties of its members in connection with the sale process. On May 26, 2004, Town Bankshare's full board of directors met to review the significant issues in the draft merger agreement with the members of the special committee. At this meeting, legal counsel also reviewed the fiduciary duties of the board of directors in connection with the sale process. On May 28, 2004, representatives of Wintrust and Wintrust's legal counsel metauthorized Barack Ferrazzano and Capital Market Securities to enter into discussions with Mr. Hickmann and Town Bankshares' legal counsel and financial advisorsWintrust to negotiate the terms of a merger agreementagreement.
     On October 20, 2005, Wintrust conducted additional due diligence at Hinsbrook. Further due diligence was conducted throughout the month of November.
     Hinsbrook and other issues related to the proposed transaction. During this meeting, a number of substantive issues were resolved and Wintrust's legal counsel undertook to circulate a revisedits advisors received an initial draft of the merger agreement on June 1. Between June 1 and June 12 legal counsel forOctober 27, 2005. Thereafter, Hinsbrook, Wintrust and Town Bankshares negotiated a numbertheir respective legal advisors engaged in negotiations of the open issues on the merger agreement. Town Bankshares delivered draft disclosure schedules to Wintrust on June 7 and Wintrust's legal counsel conducted additional due diligence with respect to Town Bankshares. As part of its bid, Wintrust required that Jay C. Mack, Town Bankshares' Chief Executive Officer and President, and Jeffrey A. Olsen, Town Bankshares' Senior Vice President - Senior Lender, enter into an employment agreement with Wintrust upon the closing of the merger. During the week of May 24, 2004, Wintrust delivered a draft of a form of employment agreement to Mr. Mack, Mr. Olsen and their legal counsel. At that time, legal counsel to Mr. Mack and Mr. Olsen suggested that each of Mr. Mack and Mr. Olsen should be paid a stay bonus by Town Bankshares in connection with the transaction and their commitment to execute employment agreements with Wintrust. Between May 26 and June 14, Mr. Mack and Mr. Olsen conducted negotiations with Wintrust regarding the terms of their employment agreements and with the special committee regarding the terms of their stay bonus agreements. On June 8, 2004, Town Bankshares' board of directors met with legal counsel and representatives of CFA to review the draft merger agreement in detail and discuss the few remaining issues on the merger agreement. The board of directors authorized the special committee to continue to negotiate the merger agreement, in an effort to resolve allexchanging comments and revised drafts of the open issues. The boardmerger agreement.
     On November 22 and November 23, 2005, representatives of directors also discussed the stay bonus agreements with Mr. MackHinsbrook and Mr. OlsenWintrust and authorized the payment of aggregate stay bonuses of $550,000. On June 11, 2004, Edelman made a presentationboth parties’ legal advisors met by telephone to the full Town Bankshares' board of directors regarding an analysis relating to Edelman's opinion. Legal counsel also summarizednegotiate the terms of the merger agreement that had changed sinceagreement. At a regular monthly meeting of the June 8Hinsbrook board meeting. Between June 11held on November 30, 2005, representatives of Barack Ferrazzano and Capital Market Securities reviewed with the board the process leading to the proposed transaction and the morningcourse of June 14, Wintrust's legal counselnegotiations with Wintrust. Representatives of Barack Ferrazzano reviewed in detail with the board the terms of the current draft of the merger agreement, including the scope of the representations and Town Bankshares' legal counsel negotiatedwarranties, the remaining open issues onnature of Hinsbrook’s operating covenants prior to closing and the proposed closing conditions.
     On December 1, 2005, members of Hinsbrook’s management and representatives of Barack Ferrazzano and Capital Market Securities met with representatives of Wintrust to conduct a due diligence review of Wintrust and its operations.
     On December 2, 2005, the Hinsbrook board held a special meeting that was also attended by representatives of Barack Ferrazzano and Capital Market Securities. At this meeting, the board received a verbal report from management and its advisors concerning the due diligence review of Wintrust. Barack Ferrazzano distributed to the board an updated draft of the merger agreement and reviewed with the relatedboard the changes from the draft received on November 30 and remaining open items. Capital Market Securities provided a financial analysis to the board of the proposed transaction documents. At a meeting held beforewith Wintrust and issued to the openingboard its oral opinion that the proposed merger consideration of $41.59 per share, as adjusted to reflect the market value of the stock markets on June 14, 2004, Edelman issued its opinion concerningportion of the fairness,consideration pursuant to the merger agreement, is fair from a financial point of view to Hinsbrook’s shareholders.
     After the conclusion of the presentations and discussions at the December 2 meeting, the Hinsbrook board unanimously approved the merger agreement and resolved to recommend that Hinsbrook shareholders approve the merger and, subject to the receipt by Hinsbrook of the written fairness opinion from Capital Market Securities, authorized the president and chief executive officer of Hinsbrook to execute the merger agreement on behalf of Hinsbrook in substantially the form reviewed by the board subject to such changes agreed to by such officer.
     On December 5, 2005, Capital Market Securities issued its written opinion to the Hinsbrook board that as of December 5, 2005, the merger consideration of $41.59 per share, as adjusted to reflect the market value of the stock portion of consideration pursuant to the merger agreement, was fair from a financial point of view to Hinsbrook’s shareholders. Also on December 5, the merger agreement was finalized and executed by Hinsbrook and Wintrust. Hinsbrook and Wintrust issued a joint press release on December 5, 2005 announcing the execution of the merger considerationagreement.
Hinsbrook’s reasons for the merger and recommendation of the board of directors
Hinsbrook’s board of directors believes that the merger is in the best interests of Hinsbrook and its shareholders. Accordingly, Hinsbrook’s board of directors has unanimously approved the merger agreement and unanimously recommends that its shareholders vote “FOR” the approval of the merger agreement.
     Hinsbrook’s board of directors has concluded that the proposed merger offers Hinsbrook’s shareholders an attractive opportunity to Town Bankshares'achieve the board’s strategic business objectives, including increasing shareholder value,

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growing the size of the business and enhancing liquidity for Hinsbrook’s shareholders, who will gain the benefit of a public trading market for their shares.
     In deciding to approve the merger agreement and Town Bankshares'the transactions it contemplates, Hinsbrook’s board of directors consulted with Hinsbrook’s management, as well as its legal counsel and financial advisor, and considered numerous factors, including the following:
information with respect to the businesses, earnings, operations, financial condition, prospects, capital levels and asset quality of Hinsbrook and Wintrust, both individually and as a combined company;
the perceived risks and uncertainties attendant to Hinsbrook’s execution of its strategic growth plans as an independent banking organization, including the need to access additional capital and enhance its technology platform on a cost-effective basis to support future growth;
the belief that the market value of Wintrust’s common stock prior to the execution of the merger agreement was very attractive and offered favorable prospects for future appreciation as a result of the proposed merger and other strategic initiatives being implemented by Wintrust;
the strategic vision of the management of Wintrust to seek profitable future expansion in the Chicago metropolitan area, leading to continued growth in overall stockholder value;
the fact that Wintrust is publicly held and the merger would provide access to a public trading market for Hinsbrook’s shareholders whose investments currently are in a privately held company, as well as enhanced access to capital markets to finance the combined company’s capital requirements; and
the likelihood that the merger will be approved by the relevant bank regulatory authorities and the other conditions to closing satisfied.
     The above discussion of the information and factors considered by Hinsbrook’s board of directors is not intended to be exhaustive, but includes all material factors considered by Hinsbrook’s board. In arriving at its determination to approve the merger agreement and the transaction it contemplates, and recommend that Hinsbrook’s shareholders vote to approve the merger, Hinsbrook’s board of directors did not assign any relative or specific weights to the above factors, and individual directors may have given differing weights to different factors.
Hinsbrook’s board of directors believes that the merger is fair to, and in the best interests of, Hinsbrook and its shareholders. Hinsbrook’s board of directors unanimously approved the merger agreement and recommends that shareholders vote “FOR” approval of the merger agreement.
     Certain directors and unanimously recommended that Town Bankshares' shareholders approveofficers of Hinsbrook have interests in the merger agreementdifferent from or in addition to their interests as shareholders generally, including certain cash payments that will be made as a result of the merger under various benefit plans and agreements currently in place in order to terminate such agreements and to be made under agreements entered into between the individuals and Wintrust in connection with the merger. You may wish to consider these interests in evaluating Hinsbrook’s board of directors’ recommendation that you vote in favor of the merger. See “The merger—Interests of certain persons in the merger.” Hinsbrook’s directors and executive officers have agreed to vote their shares in favor of the merger at the special meeting. Immediately following this meeting, Wintrust and Town Bankshares executed
Wintrust’s reasons for the merger agreement and Wintrust publicly announced the execution of the merger agreement before the opening of the stock markets. 26 WINTRUST'S REASONS FOR THE MERGER Wintrust's
     Wintrust’s board of directors believes that the merger is in the best interests of Wintrust and its shareholders. In deciding to approve the merger, Wintrust'sWintrust’s board of directors considered a number of factors, including: o management's view that the acquisition of Town Bankshares provides an attractive opportunity to expand into desirable markets in southeastern Wisconsin; o Town Bankshares' community banking orientation and its compatibility with Wintrust and its subsidiaries; o
management’s view that the acquisition of Hinsbrook provides an attractive opportunity to expand into desirable markets;
Hinsbrook’s community banking orientation and its compatibility with Wintrust and its subsidiaries;

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a review of the demographic, economic and financial characteristics of the markets in which Hinsbrook operates, including existing and potential competition and history of the market areas with respect to financial institutions;
management’s review of the business, operations, earnings and financial condition, including capital levels and asset quality, of Hinsbrook Bank & Trust since itsde novo formation in 1987;
efficiencies to come from integrating certain of Hinsbrook’s operations into Wintrust’s existing operations; and
the likelihood of regulators approving the merger without undue conditions or delay.
     The above discussion of the demographic, economicinformation and financial characteristics of the markets in which Town Bankshares operates, including existing and potential competition and history of the market areas with respect to financial institutions; o management's review of the business, operations, earnings and financial condition, including capital levels and asset quality, of Town Bank since its de novo formation in 1998; and o the likelihood of regulators approving the merger without undue conditions or delay. While Wintrust'sfactors considered by Wintrust’s board of directors is not intended to be exhaustive, but includes all material factors considered these and otherby Wintrust’s board. In view of the wide variety of factors considered by the Wintrust board of directors in connection with its evaluation of the merger, the Wintrust board did not consider it practical to, nor did it attempt to, quantify, rank or otherwise assign any specific or relative weights to the specific factors considered and did not make any determination with respectthat it considered. In considering the factors described above, individual directors may have given differing weights to any individual factor. Wintrust'sdifferent factors. Wintrust’s board of directors collectively made its determination with respect to the merger based on the conclusion reached by its members, based on the factors that each of them considered appropriate, that the merger is in the best interests of Wintrust'sWintrust’s shareholders. The terms
Fairness opinion of Hinsbrook’s financial advisor
     On June 3, 2005, Hinsbrook retained Capital Market Securities to act as its financial advisor in connection with a review of strategic alternatives, including a possible merger or sale and related matters. As part of its engagement, Capital Market Securities agreed, if requested by Hinsbrook, to render an opinion with respect to the fairness, from a financial point of view, to the holders of the Hinsbrook common stock of the merger wereconsideration as set forth in a definitive merger agreement.
     Capital Market Securities is a NASD registered broker dealer specializing in the resultfinancial services industry. In the ordinary course of arm's-lengthits investment banking business, Capital Market Securities is regularly engaged in the valuation of financial institutions and their securities in connection with mergers and acquisitions and other corporate transactions.
     Capital Market Securities acted as financial advisor to Hinsbrook in connection with the proposed merger and participated in certain aspects of the negotiations between representatives of Wintrust and representatives of Town Bankshares. TOWN BANKSHARES' REASONS FOR THE MERGER AND RECOMMENDATION OF THE BOARD OF DIRECTORS Town Bankshares'leading to the merger agreement. At the December 2, 2005 meeting at which the Hinsbrook board of directors believes that the merger is in the best interests of Town Banksharesconsidered and its shareholders. Accordingly, Town Bankshares' board of directors has unanimously approved the merger agreement, Capital Market Securities delivered its oral opinion, subsequently confirmed in writing on December 5, 2005 that, as of December 5, 2005, the merger consideration was fair to the holders of the Hinsbrook common stock from a financial point of view.
THE FULL TEXT OF CAPITAL MARKET SECURITIES’ WRITTEN OPINION IS INCLUDED ASANNEX DTO THIS PROXY STATEMENT/ PROSPECTUS. THE WRITTEN OPINION SETS FORTH, AMONG OTHER THINGS, THE ASSUMPTIONS MADE, PROCEDURES FOLLOWED, MATTERS CONSIDERED AND LIMITATIONS ON THE REVIEW UNDERTAKEN BY CAPITAL MARKET SECURITIES IN CONNECTION WITH ITS OPINION. HOLDERS OF HINSBROOK COMMON SHARES ARE URGED TO READ THE OPINION CAREFULLY AND IN ITS ENTIRETY IN CONNECTION WITH THEIR CONSIDERATION OF THE PROPOSED MERGER.
     Capital Market Securities’ opinion speaks only as of the date of the opinion. Capital Market Securities provided its opinion for the information and unanimously recommends thatassistance of the Hinsbrook board of directors in connection with its shareholders vote "FOR"consideration of the approvaltransaction contemplated by the merger agreement and is directed only to the fairness of the merger agreement.consideration to the holders of the Hinsbrook common stock from a financial point of view. The opinion does not address the underlying business decision of Hinsbrook to engage in the merger or any other aspect of the merger and is not a recommendation to any Hinsbrook shareholder as to how that shareholder should vote at the special meeting with respect to the merger, the form of consideration such shareholders should elect or any other matter. Capital Market Securities’ opinion will not reflect any developments that have occurred or may occur after

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the date of its opinion and prior to the completion of the merger. Capital Market Securities has no obligation to revise, update or reaffirm its opinion, and Hinsbrook does not currently expect that it will request an updated opinion from Capital Market Securities.
     In connection with rendering its deliberationsDecember 5, 2005 opinion, Capital Market Securities reviewed and considered, among other things:
the merger agreement;
certain publicly available financial statements and other historical financial information of Hinsbrook that Capital Market Securities deemed relevant;
certain publicly available financial statements and other historical financial information of Wintrust that Capital Market Securities deemed relevant;
the pro forma financial impact of the merger on Wintrust based on assumptions relating to transaction expenses, cost savings and other factors;
the publicly reported historical price and trading activity for Wintrust’s common stock, including a comparison of certain financial and stock market information for Wintrust with similar publicly available information for certain other banks which are publicly traded;
the financial terms of certain recent mergers in the banking industry, to the extent publicly available;
the current banking environment and economic conditions generally; and
such other information, financial studies, analyses and investigations and financial, economic and market criteria as Capital Market Securities considered appropriate for purposes of its analysis.
     Capital Market Securities also discussed with certain members of management of Hinsbrook the business, financial condition, results of operations and prospects of Hinsbrook and held similar discussions with certain members of management of Wintrust regarding the business, financial condition, results of operations and prospects of Wintrust.
     In performing its reviews and analyses and in makingrendering its determinationopinion, Capital Market Securities relied upon and assumed, without independent verification, the accuracy and completeness of all of the financial and other information that was available to unanimously approveit from public sources, that was provided by Hinsbrook or Wintrust or either’s respective representatives or that was otherwise reviewed by Capital Market Securities and assumed such accuracy and completeness for purposes of rendering its opinion. Capital Market Securities further relied on the assurances of management of Hinsbrook and Wintrust that they were not aware of any facts or circumstances that would make any of such information inaccurate or misleading. Capital Market Securities was not asked to and did not undertake an independent verification of any of such information and Capital Market Securities does not assume any responsibility or liability for its accuracy or completeness. Capital Market Securities did not make an independent evaluation or appraisal of the specific assets, the collateral securing assets or the liabilities (contingent or otherwise) of Hinsbrook or Wintrust or any of their subsidiaries, or the collectibility of any such assets, nor has Capital Market Securities been furnished with any such evaluations or appraisals. Capital Market Securities did not make an independent evaluation of the adequacy of the allowance for loan losses of Hinsbrook or Wintrust, nor has Capital Market Securities reviewed any individual credit files relating to Hinsbrook or Wintrust. Capital Market Securities assumed, with Hinsbrook’s consent, that the respective allowances for loan losses for both Hinsbrook and Wintrust are adequate to cover such losses.
     Capital Market Securities’ opinion was necessarily based upon market, economic and other conditions as they existed on, and could be evaluated as of, and the information made available to Capital Market Securities as of, the date of its opinion. Capital Market Securities assumed, in all respects material to its analysis, that all of the representations and warranties contained in the merger agreement and all related agreements are true and correct, that each party to such agreements will perform all of the covenants required to be performed by such party under such agreements and that the conditions precedent to the merger contained in the merger agreement are not waived.

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Capital Market Securities also assumed, with Hinsbrook’s consent, that there has been no material change in Hinsbrook’s and Wintrust’s assets, financial condition, results of operations, business or prospects since the date of the last financial statements made available to Capital Market Securities and that Hinsbrook and Wintrust will remain as going concerns for all periods relevant to its analyses. Finally, with Hinsbrook’s consent, Capital Market Securities relied, to the extent such advice was related to Capital Market Securities, upon the advice Hinsbrook received from its legal, accounting and tax advisors as to all legal, accounting and tax matters relating to the merger agreement and the other transactions contemplated by the merger agreement.
     The earnings projections used and relied upon by Capital Market Securities in its analyses of Hinsbrook and Wintrust, projections of transaction costs, estimates of purchase accounting adjustments and expected cost savings relating to the merger were developed by Capital Market Securities and reviewed with the assistancemanagement of Hinsbrook, and Capital Market Securities assumed for purposes of its analyses that they reflected the best currently available estimates and judgments of Hinsbrook management of the expected future financial performance of Hinsbrook and legal advisors, Town Bankshares'Wintrust, respectively, and that such performances would be achieved. These projections, as well as the other estimates used by Capital Market Securities in its analyses, were based on numerous variables and assumptions which are inherently uncertain and, accordingly, actual results could vary materially from those set forth in such projections. Capital Market Securities also assumed that the merger will qualify as a tax-free reorganization for United States federal income tax purposes and that the other transactions contemplated by the merger agreement will be consummated as described in the merger agreement. Capital Market Securities further assumed that all governmental, regulatory or other consents and approvals necessary for the completion of the merger will be obtained without any adverse effect on Hinsbrook, Wintrust or on the contemplated benefits of the merger.
     In performing its analyses, Capital Market Securities also made numerous assumptions with respect to industry performance, business and economic conditions and various other matters, many of which cannot be predicted and are beyond the control of Hinsbrook, Wintrust and Capital Market Securities. The analyses performed by Capital Market Securities are not necessarily indicative of actual values or future results, which may be significantly more or less favorable than suggested by such analyses. Capital Market Securities prepared its analyses solely for purposes of rendering its opinion and provided such analyses to the Hinsbrook board of directors considered numerous factors,at its December 2, 2005 meeting. Estimates of the values of companies do not purport to be appraisals or necessarily reflect the prices at which companies or their securities may actually be sold. Such estimates are inherently subject to uncertainty and actual values may be materially different. Accordingly, Capital Market Securities’ analyses do not necessarily reflect the value of the Hinsbrook common stock or the Wintrust common stock or the prices at which either may be sold at any time.
     In accordance with customary investment banking practice, Capital Market Securities employed generally accepted valuation methods in reaching its opinion. The following is a summary of the material financial analyses that Capital Market Securities used in reaching its opinion and presented by Capital Market Securities to Hinsbrook’s board of directors on December 2, 2005, in connection with its opinion. Some of the summaries of financial analyses are presented in tabular format. In order to understand the financial analyses used by Capital Market Securities more fully, you should read the tables together with the text of each summary. The tables alone do not constitute a complete description of Capital Market Securities’ financial analyses, including the following: o following the multi-step process described under the heading "Backgroundmethodologies and assumptions underlying those analyses, and if viewed in isolation could present a misleading or incomplete view of the merger" pursuantfinancial analyses performed by Capital Market Securities. The summary data set forth below do not constitute conclusions reached by Capital Market Securities with respect to which Town Bankshares contacted or was contacted by 141 prospective buyers, executed confidentiality agreements with 31 of these parties, and then received indications of interest from 11 of these parties over the courseany of the process, Wintrust's proposal offeredanalyses performed by it in connection with its opinion. In arriving at its opinion, Capital Market Securities considered all of the highest pricefinancial analyses it performed and more certaintydid not attribute any particular weight to closing than any other proposal; oindividual analysis or reach any specific conclusion with respect to any such analysis. Rather, Capital Market Securities made its determination as to the fairness to the holders of the Hinsbrook common stock, from a financial point of view, of the merger consideration, on the basis of $129.10its experience and professional judgment after considering the results of all of the analyses set forth in the following pages. Also, no company included in Capital Market Securities’ comparative analyses described below is identical to Hinsbrook or Wintrust and no transaction is identical to the merger. Accordingly, an analysis of comparable companies or transactions involves complex considerations and judgments concerning differences in financial and operating characteristics of the companies and other factors that could affect the public trading values or merger transaction values, as the case may be, of Hinsbrook or Wintrust and the companies to which they are being compared.

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Summary of Merger Pricing Terms. Capital Market Securities reviewed the financial terms of the proposed transaction. Hinsbrook shareholders are to receive in exchange for their Hinsbrook common stock cash consideration, stock consideration or a combination of cash and stock consideration. The per share cash consideration is $41.59. The per share stock consideration is to be calculated as a fraction of Town Bankshares common stock, payable in cash and sharesa share of Wintrust common stock between 0.680 and 0.846, depending on the average high and low sale price of Wintrust common stock on the Nasdaq National Market during the 10 trading day period ending on the fourth trading day prior to the completion of the merger. For purposes of its analysis, Capital Market Securities assumed the per share merger consideration would be equal to $41.59.
     Based upon unaudited financial information for Hinsbrook at September 30, 2005 shown below, Capital Market Securities calculated the pricing ratios set forth below:
September 30, 2005 Financial Information
(Dollar information in thousands)
     
Shareholder equity $39,888 
Tangible shareholder equity $39,888 
LTM net income $6,788 
Total deposits $424,820 
Shares Outstanding  2,750,798 
     
Pricing Ratios
    
     
Price/Tangible Book Value  287%
Price/Book Value  287%
Price to Last Twelve Months Earnings  16.9X
Purchase Price Premium above Tangible Book Value/Deposits  17.5%
Stock Trading Analysis.Capital Market Securities reviewed the history of the reported trading prices and volume of Hinsbrook’s common stock since June 30, 2005. There were a limited number of trades that have occurred, and all of the trades were Hinsbrook purchases at the price of $33.25.
     Capital Market Securities reviewed the reported trading prices and volume of Wintrust’s common stock from the period December 31, 2004 through November 25, 2005. Capital Market Securities compared the relationship between the movements in the prices of Wintrust’s common stock to movements in the prices of the Nasdaq Bank Index, the Nasdaq Composite Index and the performance of a composite peer group of publicly traded banks selected by Capital Market Securities for Wintrust. The composition of the peer group for Wintrust is discussed under the section below under the heading “—Reference Financial Institution Analysis.”
     During the analysis period ended November 25, 2005, Wintrust performed similarly to all of the indices and the peer group to which it was compared.
Reference Financial Institution Analysis. Capital Market Securities used publicly available information to compare selected financial and market trading information for each of Hinsbrook and Wintrust and two different peer groups of banks selected by Capital Market Securities. No company used in the following analyses is identical to Hinsbrook, Wintrust or, following the merger, the combined resulting company. Accordingly, such analyses are not purely mathematical; rather, they involve complex considerations and judgments concerning differences in financial, market and operating characteristics of the companies involved.

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     The comparable peer group for Hinsbrook consisted of the following publicly traded banks located in the Midwest. These companies were selected based upon their having comparable financial characteristics to Hinsbrook including: asset size, net worth ratio, profitability and level of nonperforming assets.
Baraboo Bancorporation, Incorporated
DCB Financial Corp
FNBH Bancorp, Inc.
Guaranty Federal Bancshares, Inc.
Monroe Bancorp
Southern Michigan Bancorp, Incorporated
     The analysis compared financial information for Hinsbrook and financial and market pricing data for the comparable peer group as of and for the most recently available 12-month period. The table below compares the data for Hinsbrook and the average data for the comparable peer group as of and for the 12-month period ending September 30, 2005 with market pricing data as of November 25, 2005.
Comparable Peer Group Analysis — Hinsbrook
         
      Peer Group 
  Hinsbrook  Average 
Total Assets(in millions)
 $497.0  $554.8 
Tangible Equity/Tangible Assets  8.03%  8.30%
Loans/Deposits  94.36%  103.52%
Total Borrowings/Total Assets  3.88%  12.79%
NPAs/Assets  0.34%  0.58%
ALLL/Gross Loans  0.97%  1.38%
LTM Return on Average Assets  1.42%  1.19%
LTM Return on Average Equity  19.36%  13.71%
Net Interest Margin  3.96%  4.04%
Non Interest Income/Average Assets  0.40%  0.95%
Non-Interest Expense/Average assets  1.90%  2.67%
Efficiency Ratio  46.04%  56.12%
Price/Book Value NM  182.60%
Price/Tangible Book Value NM  185.45%
Price/LTM EPS NM  13.82x
     The comparable group for Wintrust consisted of the following publicly traded banks located in the Midwest. These companies were selected based upon their having comparable financial characteristics to Wintrust including: asset size, net worth ratio, profitability and level of nonperforming assets.
First Midwest Bancorp, Inc.
FirstMerit Corporation
MB Financial, Inc.
Old National Bancorp
Park National Corporation.
Republic Bancorp Inc.

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     The analysis compared publicly available financial and market trading information for Wintrust and the data for the comparable peer group as of and for the most recently available 12-month period. The table below compares the data for Wintrust and the average data for the comparable peer group as of and for the 12-month period ended September 30, 2005 and, with market pricing data as of November 25, 2005.
Comparable Peer Group Analysis — Wintrust
         
      Peer Group 
  Wintrust  Average 
Total Assets(in millions)
 $7,894  $7,217 
Tangible Equity/Tangible Assets  5.20%  7.15%
Loans/Deposits  79.39%  94.84%
Total Borrowings/Total Assets  8.91%  21.12%
NPAs/Assets  0.25%  0.51%
ALLL/Gross Loans  0.77%  1.42%
LTM Return on Average Assets  0.90%  1.28%
LTM Return on Average Equity  12.15%  15.06%
Net Interest Margin  3.18%  3.62%
Non Interest Income/Average Assets  1.33%  1.27%
Non-Interest Expense/Average assets  2.71%  2.52%
Efficiency Ratio  63.27%  53.54%
Price/Book Value  216.30%  251.23%
Price/Tangible Book Value  332.50%  299.83%
Price/LTM EPS  20.90x  17.32x
Analysis of Selected Merger Transactions. Capital Market Securities reviewed 19 merger transactions announced in the Midwest from September 30, 2003 through November 30, 2005 involving banks as acquired institutions with a return on equity greater than 15% at the time of the deal announcement. Capital Market Securities also reviewed 11 merger transactions announced from September 30, 2003 through November 30, 2005 involving Chicago area banks as acquired institutions. Capital Market Securities reviewed the multiples of:
transaction price at announcement to book value per share,
transaction price to tangible book value per share,
transaction price to last twelve months earnings, and
purchase price premium above tangible book value to deposits and computed mean and median multiples and premiums for the transactions.
     The median multiples from the Midwest group and the median multiples for the Chicago area group were applied to Town Bankshares'Hinsbrook’s unaudited financial information as of September 30, 2005 to estimate implied transaction values involving Hinsbrook. As illustrated in the following table, Capital Market Securities derived imputed ranges of values per share of Hinsbrook’s common stock of $34.03 to $42.67 based upon the median multiples for the Midwest group and $36.08 to $46.01 based upon the median multiples for the Chicago area bank group.
Comparable Transaction Multiples
                 
          Median  
  Median     Chicago  
  Midwest Implied Area Implied
  Multiple Value Multiple Value
Transaction Price/Book Value  234.6% $34.03   256.1% $37.14 
Transaction Price/Tangible Book Value  244.6% $35.47   281.3% $40.79 
Transaction Price/LTM Earnings  17.3x $42.67   18.6x $46.01 
Transaction Value Premium above Tangible Book Value/Deposits  14.1% $36.26   14.0% $36.08 
Discounted Cash Flow Analysis. Capital Market Securities performed a discounted cash flow analysis to estimate a range of present values per share of Hinsbrook common stock. This range was calculated by adding the present value of the current and projected estimated future cash dividends that Hinsbrook was projected to pay based upon Capital Market Securities’ projections (which were reviewed by Hinsbrook’s management) and the present value of an estimated terminal value of the shares in year five calculated by applying multiples to the projected earnings per share in the fifth year. Capital Market Securities’ projections for Hinsbrook included the following basic assumptions: asset growth of approximately 10% annually, net interest margin declining approximately 2.5%

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from the level recorded in the LTM period ended September 30, 2005, noninterest income and noninterest expense levels remaining similar to historical ratios and dividend growth of 5% annually.
     In calculating a terminal value of Hinsbrook common stock, Capital Market Securities applied a range of pricing multiples between 15.0 and 19.0 to year five projected earnings. These multiples reflect recent bank acquisition pricing that Capital Market Securities believed would be applicable to Hinsbrook. In performing this analysis, Capital Market Securities assumed that there were no restrictions imposed upon Hinsbrook that would impact its ability to pay dividends and that Hinsbrook would increase its per share dividend 5% annually. In addition, Capital Market Securities used Hinsbrook’s 2005 budget and Hinsbrook’s management guidance for the five year projection period as the basis for estimating Hinsbrook earnings. The combined dividend stream and terminal value were then discounted to September 30, 2005 (the date of the most recent quarterly financial information available at the time of the analysis). Capital Market Securities estimated a range of discount rates of 12.5% to 17.5% as the appropriate rate to discount future cash flows for purposes of the analysis. These rates were chosen by Capital Market Securities to reflect different assumptions regarding the required rates of return to holders or prospective buyers of Hinsbrook common stock. As illustrated in the following table, this analysis indicated an imputed range of values per Hinsbrook common share of $25.22 to $43.66.
             
Discount Rate
  15.0x  17.0x  19.0x
          12.5% $34.82  $39.24  $43.66 
          15.0% $28.01  $31.55  $35.09 
  ��       17.5% $25.22  $28.40  $31.58 
     In connection with its analyses, Capital Market Securities considered and discussed with the Hinsbrook board of directors how the present value analyses would be affected by changes in the underlying assumptions, including variations with respect to net income. As indicated above, the projections were prepared with the guidance of the earnings projections prepared by Hinsbrook’s management and are not necessarily indicative of actual values or actual future results and do not purport to reflect the prices at which any securities currently trade or will trade at any time in the future. Capital Market Securities noted that the discounted dividend stream and terminal value analysis is a widely used valuation methodology, but the results of such methodology are highly dependent upon the numerous assumptions that must be made, and the results thereof are not necessarily indicative of actual values or future results.
     Based upon the discounted cash flow analysis as described, given that the proposed per share merger consideration is higher than most of the calculated present values, Capital Market Securities believes that this analysis supports the fairness, from a financial point of view, to Hinsbrook and its shareholders of the consideration to be paid in the merger.
Pro Forma Merger Analysis. Capital Market Securities analyzed certain potential pro forma effects of the merger, assuming the following:
the merger closed on January 1, 2006,
50% of the Hinsbrook shares are exchanged for Wintrust common shares and 50% of Hinsbrook’s shares are exchanged for $41.59 per share in cash,
projections for Hinsbrook estimated by Capital Market Securities are consistent with estimates for 2005 as provided by Hinsbrook’s management,
projections for Wintrust are consistent with Wintrust’s historical results, and,
purchase accounting adjustments, charges and transaction costs associated with the merger and cost savings estimated by Capital Market Securities.
     The analyses indicated that for the year ending December 31, 2006, the merger would be accretive to Wintrust’s projected earnings per share and the merger would be dilutive to Wintrust’s tangible book value per share. From the standpoint of a Hinsbrook shareholder electing to receive Wintrust common stock, for the year

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ending December 31, 2006, the merger would be accretive to earnings per share and historical sales prices for shares of Town Bankshares common stock; odilutive to tangible book value per share. The actual results achieved by the business, operations, competitive position, financial condition, operating results, management, objectives and prospects of Town Bankshares; o information concerning the business, financial condition, operatingcombined company may vary from projected results and competitive position of Wintrust including the recent performance of Wintrust common stock; ovariations may be material.
     Based upon the foregoing analyses and other investigations and assumptions set forth in its beliefopinion, without giving specific weightings to any one factor or comparison, Capital Market Securities determined that the resources and expertise of Wintrust as a larger organization will benefit the customers and employees of Town Bankshares; 27 o Wintrust's commitment to community banking and to maintaining local management and decision-making at its subsidiary banks; o the opinion of Edelman that theaggregate merger consideration was fair from a financial point of view to Town Bankshares shareholders as of the time of the issuance of the opinion and subject to the assumptions, matters considered and qualifications and limitations on the review contained therein; o the fact that Wintrust common stock is publicly held and traded on the Nasdaq National Market and would provide greater liquidity than Town Bankshares common stock, which is not publicly traded; o the terms and conditions of the merger agreement, including the floating exchange ratio if the average trading price per share of Wintrust common stock over a 10-trading day period before the closing of the merger is at least $41.34 and no more than $55.34, the agreement by Town Bankshares not to solicit third-party offers, the termination fee applicable in some circumstances, and the determination of the board of directors that these terms and conditions were appropriate in a strategic transaction of this type; and o the fact that the merger agreement allows Town Bankshares to terminate its obligation to complete the merger if the average trading price per share of Wintrust common stock over a 10-trading day period before the closing of the merger is less than $38.34. Town Bankshares' board of directors also considered certain potential adverse consequences of the merger, including the following: o the possibility that the agreements by Town Bankshares not to solicit third-party offers andHinsbrook’s shareholders.
     Hinsbrook has agreed to pay a termination fee to Wintrust in some circumstances could inhibit or preclude competing purchase offers; o the significant costs involvedCapital Market Securities total transaction fees in connection with the merger and the risk of diverting management's attention and resources from other strategic opportunities and operational mattersequal to focus on combining the companies; o the board of directors acknowledged that the merger will be a taxable transaction to the extent that shares of Town Bankshares common stock are exchanged for cash in the merger and, as a result, holders of shares of Town Bankshares common stock may be required to pay taxes on any taxable gain as a result of receipt of the cash portionone percent of the merger consideration; and o the risks associated with possible delays in obtaining necessary approvals and the terms of such approvals. Town Bankshares' board concluded that the anticipated benefitsconsideration (approximately $1,150,000). Of these transaction fees, as of the merger were likely to substantially outweigh the preceding risks. In reaching its determination to accept the merger agreement proposed by Wintrust, Town Bankshares' boarddate of directors did not assign any relative or specific weights to the factors considered,this proxy statement/prospectus, Capital Market Securities has received $100,000 in retainer fees and individual directors may have given different weights to different factors. Although there can be no assurance, Town Bankshares' board of directors also believes that the merger will provide Town Bankshares' shareholders with increased value and liquidity for their stock and will provide its communities and customers with expanded services and products. TOWN BANKSHARES' BOARD OF DIRECTORS BELIEVES THAT THE MERGER IS FAIR TO, AND IN THE BEST INTERESTS OF, TOWN BANKSHARES AND ITS SHAREHOLDERS. TOWN BANKSHARES' BOARD OF DIRECTORS UNANIMOUSLY APPROVED THE MERGER AGREEMENT AND RECOMMENDS THAT SHAREHOLDERS VOTE "FOR" APPROVAL OF THE MERGER AGREEMENT. Certain directors and officers of Town Bankshares have interests in the merger in addition to their interests as shareholders generally, including entitlement to certain cash payments that will be made as a result of the merger under various benefit plans and agreements currently in place and to be made under agreements entered into between the individuals and Wintrust$100,000 in connection with the merger. You may wish to consider these interests in 28 evaluating Town Bankshares' boarddelivery of directors' recommendation that you vote in favorits fairness opinion. Payment by Hinsbrook of the remainder of the transaction fees is contingent on the closing of the merger. See "DescriptionHinsbrook has also agreed to reimburse certain of the merger--Interests of certain persons in the merger." FAIRNESS OPINION OF TOWN BANKSHARES' FINANCIAL ADVISOR On June 3, 2004, Town Bankshares engaged Edelman & Co., Ltd. ("Edelman") to undertake to render an opinion to the Town Bankshares board of directors as to the fairness, from a financial point of view, to Town Bankshares' shareholders of a proposed acquisition by Wintrust. Edelman is a financial advisory and consulting firm engaged in advising financial institutions and other businesses regarding mergers and acquisition transactions and other matters. Town Bankshares selected Edelman because of its expertise with financial institutions and mergers and acquisitions. No limitations were imposed by Town Bankshares on the scope of Edelman's investigation or the procedures Edelman followed in connection with preparing its opinion. Edelman was not requested to and did not make any recommendation to Town Bankshares' board of directors as to the terms of the transaction, which were determined through negotiations between Town Bankshares and Wintrust in which Edelman did not participate. At a meeting of the Town Bankshares board of directors on June 14, 2004, Edelman provided its verbal fairness opinion to the board. It was noted (1) that Town Bankshares and Wintrust had entered into an Agreement and Plan of Merger ("the Agreement"), providing for the merger of Town Bankshares with and into Wintrust, (2) that the Agreement provided for shares of common stock, $.01 par value per share, of Town Bankshares, other than shares held by Town Bankshares' Employee Stock Ownership Plan which are to be redeemed for cash, to be converted into the right to receive a combination of cash and shares of Wintrust common stock, no par value, having an aggregate value of $129.10 (the "Consideration"), and (3) that the terms and conditions of the merger, including but not limited to provisions concerning the number of Wintrust shares to be issued with respect to Town Bankshares shares, and allowing the parties to terminate the Agreement based on trading levels of Wintrust's shares (the "Termination Right"), were more fully described in the Agreement. Edelman's opinion, subsequently delivered in written form, indicated that the Consideration was fair, from a financial point of view, to the holders of Town Bankshares common stock. THE FULL TEXT OF EDELMAN'S OPINION IS ATTACHED TO THIS PROXY STATEMENT/PROSPECTUS AS ANNEX D AND IS INCORPORATED HEREIN BY REFERENCE. THE SUMMARY SET FORTH IN THIS PROXY STATEMENT/PROSPECTUS IS QUALIFIED IN ITS ENTIRETY BY REFERENCE TO THE FULL TEXT OF THE OPINION, AND SHAREHOLDERS ARE URGED TO READ THE OPINION. In forming its opinion, Edelman reviewed, among other things, (1) Wintrust's Annual Reports on Form 10-K and Annual Reports to Shareholders for the fiscal years ended December 31, 1999 through 2003, and its Quarterly Report on Form 10-Q for the quarter ended March 31, 2004; (2) Town Bankshares' audited financial statements for the fiscal years ended December 31, 1999 through 2003, and its unaudited internal balance sheet and income statement, provided by Town Bankshares, for the quarter ended March 31, 2004; (3) the Agreement; (4) certain other information concerning the future prospects of Wintrust and Town Bankshares, and of the combined entity, as furnished by the respective companies, which Edelman discussed with the senior management of Wintrust and Town Bankshares; (5) historical market price and trading data for Wintrust's common stock and, as provided by Town Bankshares, for Town Bankshares common stock; (6) the financial performance and condition of Wintrust and Town Bankshares and similar data for other financial institutions which Edelman believed to be relevant; (7) the financial terms of other mergers which Edelman believed to be relevant; and (8) such other information as Edelman deemed appropriate. Edelman met with certain senior officers of Wintrust and Town Bankshares to discuss the foregoing as well as other matters relevant to its opinion including Wintrust's and Town Bankshares' past and current business operations, financial condition and future prospects. Edelman also took into account its assessment of general economic, market and financial conditions, and such additional financial and other factors it deemed relevant. In conducting its review and preparing its opinion, Edelman assumed and relied upon the accuracy and completeness of the financial and other information used by it without independently verifying any such information and further relied upon the assurances of Wintrust's and Town Bankshares' respective managements that they were 29 not aware of any facts or circumstances that would make such information misleading or inaccurate. Edelman also relied upon the accuracy and completeness of Wintrust's and Town Bankshares' representations, warranties and covenants contained in the Agreement. Edelman assumed that the merger would be consummated on the terms described in the Agreement in the absence of circumstances creating a Termination Right on the part of Town Bankshares, that all conditions to consummation of the merger set forth in the Agreement would be satisfied, and that the merger would be consummated on a timely basis. Edelman relied upon Wintrust's and Town Bankshares' respective managements in forming a view of Wintrust's and Town Bankshares' future prospects, and in forming assumptions regarding a variety of matters. Edelman assumed, without independent verification, that Wintrust's and Town Bankshares' allowances for loan losses were adequate to cover such losses. Edelman did not inspect any of Wintrust's or Town Bankshares' properties, assets or liabilities and did not make or obtain any evaluations or appraisals of Wintrust's or Town Bankshares' properties, assets or liabilities. EDELMAN'S OPINION TO TOWN BANKSHARES' BOARD OF DIRECTORS WAS DIRECTED SOLELY TO THE FAIRNESS, FROM A FINANCIAL POINT OF VIEW, OF THE CONSIDERATION AND DID NOT ADDRESS THE DECISION TO EFFECT THE MERGER OR CONSTITUTE A RECOMMENDATION TO ANY TOWN BANKSHARES SHAREHOLDER AS TO HOW SUCH SHAREHOLDER SHOULD VOTE ON THE MERGER. THE OPINION WAS BASED ON ECONOMIC AND MARKET CONDITIONS AND OTHER CIRCUMSTANCES EXISTING AT THE TIME THE OPINION WAS RENDERED ON JUNE 14, 2004. EDELMAN DID NOT EXPRESS ANY OPINION ON THE VALUE OF WINTRUST'S COMMON STOCK, OR THE IMPACT THAT THE MERGER WOULD HAVE ON THE VALUE OF WINTRUST'S COMMON STOCK IN THE FUTURE, OR ON AN APPROPRIATE COURSE OF ACTION BY TOWN BANKSHARES' BOARD OF DIRECTORS SHOULD CIRCUMSTANCES GIVE RISE TO A TERMINATION RIGHT ON THE PART OF TOWN BANKSHARES. EDELMAN EXPRESSED NO OPINION ON MATTERS OF A LEGAL, REGULATORY, TAX OR ACCOUNTING NATURE. In connection with rendering its opinion to the Town Bankshares board, Edelman performed a variety of financial analyses that are summarized below. The preparation of a fairness opinion is a complex process involving subjective judgments and quantitative analysis and is not necessarily susceptible to partial analysis or summary description. Edelman believes that its analyses and this summary must be considered as a whole and that selecting portions of its analyses and the factors it considered, without considering all factors and analyses, creates an incomplete view of the analyses and processes underlying Edelman's opinion. Any estimates or assumptions used in Edelman's analyses are not necessarily indicative of actual future value or results, which may be significantly more or less favorable than is suggested by these estimates. No company or previous transaction used in Edelman's analyses was identical to Wintrust or Town Bankshares or the merger. The fact that any specific analysis has been referred to in the summary below is not meant to indicate that such analysis was given more weight than any other analysis. Edelman may have given various analyses more or less weight than other analyses, and may have deemed various assumptions more or less probable than other assumptions. The following is a brief summary of the analysis performed by EdelmanCapital Market Securities’ reasonable out-of-pocket expenses incurred in connection with its opinion. 1. Comparable Company Analysis. Edelman comparedengagement and to indemnify Capital Market Securities and its affiliates, their respective partners, directors, officers, agents and employees of Capital Markets Securities and its affiliates, and each other person, if any, controlling Capital Markets Securities or its affiliates against certain expenses and liabilities, including liabilities under securities laws.
     Capital Market Securities is affiliated with Young & Associates, Inc., a firm that provides consulting, outsourcing and educational services to financial ratios of Town Bankshares and Wintrustinstitutions. Young & Associates has provided consulting services to those of banks and bank holding companies (1) nationwide, (2) headquartered in the Midwest, (3) with assets of $2 billion to $8 billion (publicly traded only), and (4) with assets of $100 million to $350 million. Ratios included return on average assets (ROA), return on average equity (ROE), tangible equity to tangible assets (Capital), and non-performing assets to total assets (NPA/A). Adjustments were made for Wintrust's and Town Bankshares' securities gains, and for Town Bankshares' expensesHinsbrook since approximately 1990, including consulting services related to the merger. Based on last 12 months dataHinsbrook’s strategic planning. In 2004, 2005 and median industry data from SNL Financial, L.C., these results were as follows: ROA ROE CAPITAL NPA/A ----- ----- ------- ----- Town Bankshares.............. 0.80% 9.9% 7.4% 0.00% Wintrust..................... 0.92% 13.4% 6.5% 0.34% Nationwide................... 1.03% 10.2% 9.3% 0.35% Midwest...................... 1.06% 10.4% 9.5% 0.37% $2 billion - $8 billion...... 1.17% 13.4% 6.9% 0.37% $100 million-$350 million.... 1.07% 11.0% 9.0% 0.37% 2. Contribution Analysis. Edelman calculated the proportions of total Town Bankshares2006, Young & Associates received fees totaling approximately $32,800, $27,900 and Wintrust tangible equity, assets, deposits, and net income that were contributed by Town Bankshares. Net income was calculated with adjustment for securities gains and Town Bankshares expenses related to the merger. Results of 30 Town Bankshares$8,120, respectively, for its most recent quarter were also adjusted for a non-recurring income item. Usingservices to Hinsbrook, which does not include the sum of the respective company values atabove described fees paid or for the period ended March 31, 2004, the Town Bankshares contribution was 5.3% of tangible equity, 4.5% of assets, 4.9% of deposits, 3.7% of most recent quarter income, and 3.9% of last 12 months income. By comparison, Town Bankshares contributed 3.8% of the sum of Wintrust's market capitalization (based on latest available diluted shares) and Town Bankshares' value as measured by the $41.4 million combined value of Consideration to be paid to Town Bankshares' shareholders and consideration received by Town Bankshares' option holders in the merger ("Deal Value"). 3. Trading. Edelman analyzed various characteristics of the trading markets for Town Bankshares and Wintrust common stock. During the period from May 1, 2003 through June 10, 2004, Wintrust common stock had an average daily trading volume of 105,012 shares, or .52% of its shares outstanding as of March 31, 2004, compared to 50 shares and .02% for Town Bankshares. Edelman further analyzed the trading value of Wintrust shares in relation to its last 12 months earnings per share and tangible book value per share (based on latest announced quarterly balance sheet values) in comparison to values for all publicly traded banks (1) nationwide, (2) headquartered in the Midwest, and (3) with assets of $2 billion to $8 billion. Using Wintrust's recent trading pricing and median industry data (excluding pink sheet companies) as of June 2, 2004 from SNL Financial, these results were as follows: P/E P/TB ----- ---- Wintrust.......................... 23.4 308% All nationally.................... 16.9 222% Midwest only...................... 16.9 220% Assets $2 billion - $8 billion.... 17.2 272% Edelman further determined that based on the current dividend rate and recent trading value of Wintrust common stock, Town Bankshares' shareholders would receive in the merger a dividend yield of approximately .4% in relation to the value of their holdings of Town Bankshares common stock (valued at its latest trading price prior to announcement of the merger). Town Bankshares has not historically paid dividends on its common stock. 4. Comparable Transaction Analysis. Edelman analyzed certain industry pricing statistics regarding bank acquisitions and compared these to pricing ratios in the merger. The following table shows median price to tangible book value (P/TB), price to earnings (P/E) and price to total deposits (P/D) ratios for three comparable transactions groups: all acquisitions of banks nationally, acquisitions of banks headquartered in the Midwest, and acquisitions of banks with assets of $125 million to $350 million. P/E P/TB P/D ----- ---- ----- All nationally............... 24.7 240% 23.3% Midwest only................. 24.4 216% 21.6% Assets (M) $125 - $350....... 24.1 246% 23.8% The data above was gathered from the SNL Financial database with respect to transactions announced from May 1, 2003 through June 1, 2004. Mergers of equals, acquisitions of thrifts, terminated transactions and transactions with pricing data unavailable were excluded. Statistics as of transaction announcement were used unless closing pricing data was available. The number of transactions in the respective groups was as follows: All nationally (167), Midwest only (43), and assets of $125 million - $350 million (50). By comparison, in the merger P/TB and P/D were 236% and 19.9%, respectively. In calculating P/E with respect to the merger, different earnings inputs and calculation methodologies were used. Based on last 12 months income, as adjusted for securities gains and expenses related to the merger, the P/E was 22.8 using purchase price per share divided by adjusted diluted earnings per share, while it was 24.9 using Deal Value divided by adjusted net income. 5. Wintrust Trading Price Sensitivity Analysis. Edelman noted that Wintrust operates in an environment of several risk factors, some characteristic of the banking industry and some particular to Wintrust, such as those disclosed in Wintrust's SEC filings. Edelman analyzed the implications on the merger pricing ratios 31 calculated in analysis #4 above of an assumption that Wintrust's common stock would trade at the industry P/E ratios set forth under analysis #3 above. For example, the national average bank trading P/E set forth under analysis #3 was 28% lower than Wintrust's trading P/E. It was calculated that a 28% reduction in the dollar value of the stock portion of the Consideration would change the merger P/E ratio of 24.9 set forth above under analysis #4 to 21.3. However, it was noted that the terms of the merger include a pricing mechanism which adjusts for fluctuations in Wintrust trading price during the pendency of the merger. It was determined that as of closing the $129.10 Consideration price per share could fall no more than 4.0% as a result of a decline in Wintrust's trading price without creating a Termination Right on the part of Town Bankshares. It was further determined that upon closing, shares of Wintrust common stock to be received by Town Bankshares' shareholders would be freely tradeable. 6. Premium Analysis. Edelman analyzed the price to be paid for Town Bankshares common stock in comparison to the historical trading value of the stock. It was determined that the Consideration level of $129.10 per share represented a premium of 83% over the latest and highest market sale price recorded for Town Bankshares common stock. 7. Impact Analysis. Edelman analyzed the pro forma impact of the merger on Wintrust's earnings per share ("EPS") under various scenarios and based upon certain assumptions, including but not limited to: (a) Wintrust's guidance suggesting a current 2004 EPS rate of $2.25 to $2.40, and (b) no cost or revenue synergies or purchase accounting adjustments affecting income as a result of the merger. In a scenario reflecting (1) the high end of the EPS guidance, (2) Town Bankshares' net income for the last 12 months adjusted for securities gains and transaction-related expense, and (3) the maximum number of Wintrust shares issued under the Agreement (as driven by Wintrust's common stock price), Wintrust's EPS was shown to decrease by .37%. By altering this scenario to use the low end of the EPS guidance and the minimum Wintrust share issuance, Wintrust's EPS was shown to increase by .35%. Edelman also analyzed the pro forma impact of the merger on Wintrust's tangible book value per share ("TBVPS"). Depending upon the number of Wintrust's shares to be issued in the merger, and based on assumptions including but not limited to an absence of purchase accounting mark-to-market adjustments, TBVPS was shown to decrease 1.9% to 2.5%. Edelman and Town Bankshares entered into an agreement relating to the services Edelman provided in connection with its opinion. Under the agreement, Town Bankshares agreed to indemnify Edelman against certain liabilities. Pursuant to the agreement, Town Bankshares has paid Edelman fees totaling $70,000 and has agreed to reimburse Edelman for out-of-pocket expenses associated with its services. ACCOUNTING TREATMENTCapital Market Securities.
Accounting treatment
     Wintrust will account for the merger under the "purchase"“purchase” method of accounting in accordance with accounting principles generally accepted in the United States. Using the purchase method of accounting, the assets and liabilities of Town BanksharesHinsbrook will be recorded by Wintrust at their respective fair values at the time of the completion of the merger. The excess of Wintrust'sWintrust’s purchase price over the net fair value of the assets acquired and liabilities assumed will then be allocated to identified intangible assets, with any remaining unallocated cost recorded as goodwill. TAX CONSEQUENCES OF THE MERGER General.
Certain federal income tax consequences of the merger
General. The following discussion addresses the materialcertain United States federal income tax consequences of the merger that are generally applicable to Town Bankshares'Hinsbrook’s shareholders. It does not address the tax consequences of the merger under foreign, state, or local tax laws or the tax consequences of transactions completed before or after the merger. Also, the following discussion does not deal with all federal income tax considerations that may be relevant to certain Town BanksharesHinsbrook shareholders in light of their particular circumstances, such as shareholders who: o
are dealers in securities;
are insurance companies or tax-exempt organizations;
are subject to alternative minimum tax;
hold their shares as part of a hedge, straddle, or other risk reduction transaction; or
are foreign persons.
You are dealers in securities; o are insurance companies or tax-exempt organizations; o are subjecturged to alternative minimum tax; 32 o hold their shares as partconsult your own tax advisors regarding the tax consequences of a hedge, straddle, or other risk reduction transaction; or o arethe merger to you based on your own circumstances, including the applicable federal, state, local and foreign persons. YOU ARE URGED TO CONSULT YOUR OWN TAX ADVISORS REGARDING THE TAX CONSEQUENCES OF THE MERGER TO YOU BASED ON YOUR OWN CIRCUMSTANCES, INCLUDING THE APPLICABLE FEDERAL, STATE, LOCAL AND FOREIGN TAX CONSEQUENCES.tax consequences.
     The following discussion is based on the Internal Revenue Code of 1986, as amended, or the Code, applicable Treasury Regulations, judicial decisions, and administrative rulings and practice, all as of the date of this

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document and all of which are subject to change.change, possibly with retroactive effect. Any change could be applied to transactions that were completed before the change, and could affect the accuracy of the statements and conclusions in this discussion andas well as the tax consequences of the merger to Wintrust, Town Bankshares and the Town Bankshares shareholders. merger.
Tax Opinion of Reinhart Boerner Van Deuren s.c. Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP.Neither Wintrust nor Town BanksharesHinsbrook has requested, nor will they request, a ruling from the Internal Revenue Service with regard to the federal income tax consequences of the merger. Instead, as a condition to the closing of the merger, Reinhart Boerner Van Deuren s.c., legalBarack Ferrazzano Kirschbaum Perlman & Nagelberg LLP, special counsel to Town Bankshares,Hinsbrook, will render its opinion to Town Bankshares,Hinsbrook, subject to customary representations and assumptions referred to in the opinion, substantially to the effect that: o the merger will constitute a reorganization within the meaning of Section 368(a) of the Code and Town Bankshares and Wintrust will each be a "party to a reorganization" within the meaning of Section 368(b) of the Code; and o no gain or loss will be recognized by Town Bankshares shareholders upon the receipt of Wintrust common stock in exchange for Town Bankshares common stock, except with respect to the cash portion of the merger consideration and cash received for a fractional share of Wintrust common stock; Reinhart Boerner Van Deuren's
the merger will constitute a reorganization within the meaning of Section 368(a) of the Code and Hinsbrook and Wintrust will each be a “party to a reorganization” within the meaning of Section 368(b) of the Code; and
no gain or loss will be recognized by Hinsbrook shareholders upon the receipt of Wintrust common stock in exchange for Hinsbrook common stock, except with respect to the cash portion of the merger consideration and cash received for fractional shares of Wintrust common stock.
     Barack Ferrazzano’s opinion will be based upon the assumption that the merger will take place substantially in the manner described in the merger agreement and will also assume the truth and accuracy of certain factual representations that will have been made by Wintrust and Town BanksharesHinsbrook and which are customarily given in transactions of this nature. Reinhart Boerner Van Deuren's opinion will require that at least 50% of the value of the total merger consideration issuable to the holders of shares of Town Bankshares common stock in the merger consist of shares of Wintrust common stock (valuing the Wintrust common stock based on the closing price of the Wintrust common stock as of the date of the closing of the merger). If the value of the stock consideration is less than 50% of the total merger consideration, Reinhart Boerner Van Deuren may not be able to issue its opinion. Since the per share stock consideration in the merger will be determined based on average price of Wintrust's common stock during the 10-trading day pricing period ending two trading days before the merger is completed, the closing price of Wintrust's common stock as of the date of the merger may be less than the average price during the pricing period, or the average price during the pricing period may be less than $41.34 per share, resulting in a fixed exchange ratio of 1.717 shares of Wintrust common stock for each share of Town Bankshares common stock, which in either case would decrease the value of the stock consideration as of the closing of the merger as compared to the cash consideration. Also, the value of the cash consideration in the merger will increase if one or more holders of shares of Town Bankshares common stock exercise dissenters' rights and will also be affected by the amount of cash paid in lieu of fractional shares. Reinhart Boerner Van Deuren'sBarack Ferrazzano’s opinion will not be binding on the Internal Revenue Service or the courts and there can be no assurance that the Internal Revenue Service will not take a contrary position to one or more positions reflected herein or that the opinion will be upheld by the courts if challenged by the Internal Revenue Service.
Gain recognition and tax basis. For United States federal income tax purposes, the "realized gain"Recognition on Receipt of a Town Bankshares shareholderCash. Hinsbrook shareholders will be equalrecognize gain (but not loss) with respect to the aggregate consideration (both stock and cash) received in the reorganization less the shareholder's basis in his or her Town Bankshares' common stock exchanged. The portion of the shareholder's "realized gain" which must be "recognized" will be equal to the lesser of the cash received (excluding cash received in lieu of fractional shares) or the realized gain as a result of the merger (adjusted for any gain recognized for cash received in lieu of fractional shares). In general, the tax basis in shares of Town Bankshares common stock will carry over to the shares of Wintrust common stock received in exchange therefor. The tax basis of the Wintrust common stock received by Town Bankshares shareholders in the merger will equal the tax basis in the Town Bankshares common stock exchanged for the merger consideration, decreased by the amount 33 of any cash received (other than cash received in lieu of fractional shares of Town Bankshares common stock) and increased by the amount of any cash received which was treated as a dividend and the amount of any gain recognized in the exchange. The gain recognized as a result of cash received in lieu of a fractional share will be equal to the excess of such cash over the tax basis attributable to the share or shares of Town Bankshares common stock exchanged therefor. Withholding. Any cash payments received in the merger, including the cash portion of the merger consideration andthey receive. The amount of gain will be limited to the amount of cash received. Additionally, any cash received by Hinsbrook shareholders instead of fractional shares of Wintrust’s common stock will result in lieugain or loss. The amount of the recognized gain to Hinsbrook shareholders will generally be treated as capital gain, unless the receipt of cash has the effect of the distribution of a dividend, in which case, the gain recognized will generally be treated as a dividend. Net capital gain recognized by individual and other non-corporate shareholders from the sale or exchange of stock or securities held for more than twelve months, and certain dividend income, are generally taxed at a maximum federal income tax rate of 15%.
Withholding. The cash portion of the merger consideration and any cash payments in respect of a fractional share of Wintrust common stock may be subject to the information reporting requirements of the Internal Revenue Service and to backup withholding at the current rate of 28%. Backup withholding will not apply to a payment made to you if you complete properly and timely and sign the substitute Form W-9W–9 that will be included as part of the transmittal letter and notice from Wintrust'sWintrust’s exchange agent, or you otherwise prove to Wintrust and its exchange agent that you are exempt from backup withholding.
     Backup withholding is not an additional tax, but an advance payment. Any amount withheld from the payment of the merger consideration may be credited against the United States federal income tax liability of the beneficial owner subject to the withholding and may be refunded to the extent it results in an overpayment of tax. You should consult with your tax advisor as to your qualification for exemption from backup withholding and the procedures for obtaining this exemption.
Reporting and Record Keeping.Keeping. If you exchange shares of Town BanksharesHinsbrook common stock in the merger for Wintrust common stock, you are required to retain records of the transaction, and to attach to your federal income tax return for the year of the merger a statement setting forth all relevant facts with respect to the nonrecognition of gain or loss upon the exchange. At a minimum, the statement must include: o your tax basis in the Town Bankshares common stock surrendered; and o
your tax basis in the Hinsbrook common stock surrendered; and
the amount of cash (if any) received and the fair market value, as of the effective date of the merger, of the Wintrust common stock received in exchange therefor.

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The preceding does not purport to be a complete discussion of all potential federal income tax consequences of the merger that may be relevant to a particular Hinsbrook shareholder. You are urged to consult with your own tax advisor regarding the specific tax consequences to you as a result of the merger, including the applicability and effect of foreign, state, local and other tax laws.
Regulatory approvals
     The merger cannot proceed without obtaining all requisite regulatory approvals. Wintrust common stock received in exchange therefor. THE PRECEDING DISCUSSION DOES NOT PURPORT TO BE A COMPLETE ANALYSIS OF ALL POTENTIAL TAX CONSEQUENCES OF THE MERGER THAT MAY BE RELEVANT TO A PARTICULAR TOWN BANKSHARES SHAREHOLDER. YOU ARE URGED TO CONSULT WITH YOUR OWN TAX ADVISOR REGARDING THE SPECIFIC TAX CONSEQUENCES TO YOU AS A RESULT OF THE MERGER, INCLUDING THE APPLICABILITY AND EFFECT OF FOREIGN, STATE, LOCAL AND OTHER TAX LAWS. REGULATORY APPROVALShas agreed to take all appropriate actions necessary to obtain the required approvals.
     The merger of Wintrust and Town BanksharesHinsbrook is subject to prior approval of each of the Federal Reserve and the Division of Banking of the WDFI.IDFPR. Wintrust submitted an application towith the Federal Reserve Bank of Chicago in January of 2006 seeking the necessary approval. Although there can be no assurance that the Federal Reserve will approve the merger or as to the timing of approval, Wintrust currently expects it will receivereceived approval of the merger from the Federal Reserve during the third quarter of 2004.on February 24, 2006. Wintrust filed the required application with the DivisionIDFPR in January of Banking2006 and received approval of the WDFImerger from the IDFPR on July 23, 2004. The Division of Banking of the WDFI is required to render a decision on the application within 30 days after Wintrust satisfied the notice publication requirements with respect to the application filing, which requirements were satisfied on August 11, 2004.April 12, 2006.
     The merger may not be consummated until approximately 15 days after receipt of Federal Reserve approval, during which time the United States Department of Justice may challenge the merger on antitrust grounds. The commencement of an antitrust action would stay the effectiveness of the Federal Reserve'sReserve’s approval, unless a court specifically orders otherwise.
Interests of certain persons in the merger
General. Members of the board of directors and executive officers of Hinsbrook may have interests in the merger that are different from, or are in addition to, the interests of Hinsbrook shareholders generally. The Hinsbrook board of directors was aware of these interests and considered them, among other matters, in approving the merger cannot proceed without obtaining all requisite regulatory approvals. Wintrust has agreedagreement and determining to take all appropriate actions necessaryrecommend to obtainHinsbrook shareholders to vote for approval of the required approvals. INTERESTS OF CERTAIN PERSONS IN THE MERGERmerger agreement. As of August 18, 2004, Town Bankshares'the record date, Hinsbrook’s directors and Town Bank's directors andexecutive officers owned, in the aggregate, 50,3581,061,696 shares of Town Bankshares'Hinsbrook’s common stock, representing approximately 16.9%38.4% of Town 34 Bankshares'Hinsbrook’s outstanding shares of common stock, andstock. None of Hinsbrook’s directors or executive officers own any options to purchase an aggregate of 38,400 shares of Town Bankshares'Hinsbrook’s common stock with a weighted average exercise price of $57.53 per share. Town Bankshares' stock option plan provides that all outstanding unvested stock options to purchase Town Bankshares common stock will immediately vest upon the completion of the merger, which would be considered a "change of control" for purposes of these stock options.stock.
Substitute Stock Options. Wintrust has agreed to assume all outstanding Town BanksharesHinsbrook stock options.options, all of which are already vested. At the time the merger is completed, each outstanding Town BanksharesHinsbrook stock option will be converted into an option to purchase Wintrust common shares exercisable on generally the same terms as in effect immediately prior to completion ofand conditions that applied before the merger, except that the number of shares of Wintrust common stock issuable upon the exercise of the options and the exercise price per share will be adjusted based on the per share merger consideration, and all Town Banksharesconsideration. Hinsbrook’s employees hold options to purchase a total of 3,125 shares of Hinsbrook common stock options outstanding will become fully vested and exercisable at the effective timea weighted average exercise price of $20.00 per share. See “Description of the merger dueagreement—Consideration to be received in the "change in control" provisions discussed above. Accordingly, the completion of the merger will accelerate the vesting of 8,780 options held by Town Bankshares' executive officers to purchase shares of Town Bankshares common stock at an exercise price of $60 per share that were not previously exercisable. merger—Stock Options.”
Employment Agreements.Agreements. The merger agreement requires two of Town Bankshares' executive officers, Jay C. Mack and Jeffrey A. Olsen,Hinsbrook Bank & Trust to enter into an employment agreementsagreement with Town Bank.each of Jeffrey D. Baker, Andrew M. Collins, Jr., L. Thomas McNamara and Regina R. Miller. The termsterm of boththe agreements will commence on the closing date of the merger. In this section, Jeffrey D. Baker, Andrew M. Collins, Jr., L. Thomas McNamara and Regina R. Miller are sometimes referred to individually as an “executive” or together as the “executives.”
The term of each employment agreement will be three years from the closing date of the merger, except for the employment agreement with Mr. McNamara the term of which will expire at the end of 2006. The agreements is five years. Each of the agreements isare subject to automatic renewal for successive one-year terms unless either of the parties to each of the agreements gives notice of its intention not to renew at least 9060 days before the expiration of the then current term. The term of each agreement may be extended upon a “change in control” of Hinsbrook Bank & Trust. Each of the employment agreements containsagreement will contain a non-compete and non-solicitation provision and a confidentiality provision. Each of theThe non-compete and non-solicitation provisions will remain in effect for two years after termination of employment and the confidentiality provisions will survive indefinitely. Each of the

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     The agreements provideswill provide for a base salary as may, from time to time, be agreed upon by the parties, providedand participation in compensation, insurance and benefit plans as may be available to employees of Wintrust or its affiliates. Additionally, the agreements will provide for severance benefits of two times base salary and any bonuses paid during the previous 12 months if the executive is terminated (i) due to death, (ii) due to permanent disability, (iii) without cause, (iv) constructively or (v) following a change of control.
Deferred Compensation Agreements and Deferred Fee Agreements. Hinsbrook Bank & Trust previously entered into deferred compensation agreements and deferred fee agreements with 16 of its officers and two of its directors. The deferred compensation arrangements generally provide that the amountindividual will be permitted to defer a portion of their salary (or fees with respect to directors) and Hinsbrook Bank & Trust will match a portion of such deferrals in a notional account on behalf of the salary may notindividual. The notional accounts accrue interest at a stated rate, which varies by individual and currently ranges from the prime rate as reported in the Wall Street Journal plus 1% to the prime rate plus 5%, until all obligations are paid. As reported in the Wall Street Journal, the prime rate on January 4, 2006 was 7.25%. Although certain individuals have a right to require that accrued amounts be reduced belowheld in a grantor trust, the base salary asobligations to the individuals are at all times an unfunded obligation to pay amounts in the future, with such obligations subject to the claims of creditors of Hinsbrook Bank & Trust. Hinsbrook Bank & Trust’s accrued liability with respect to the effective datedeferred compensation and fee arrangements was approximately $2,986,545 and $2,401,000 at December 31, 2005 and December 31, 2004, respectively. Deferred compensation and fee expense for the year ended December 31, 2005 and December 31, 2004, was approximately $409,061 and $334,000, respectively. As discussed in “Description of the merger unless the reduction is no greater in percentage terms than a general reduction in the base salariesagreement—Conditions to completion of the President, Chief Executive Officer and Vice Presidentmerger,” Wintrust’s obligations under the merger agreement are subject to Hinsbrook Bank & Trust having amended each of Wintrust. As ofthe deferred compensation arrangements prior to the effective time of the merger, to eliminate any future individual deferrals or any required company matching contributions under the annual base salariesarrangements. Other than with respect to the noted amendments, the arrangements will continue in effect per their terms.
Change in Control Agreements. Hinsbrook Bank & Trust previously entered into change of Messrs. Mackcontrol agreements with each of Jeffrey D. Baker, Robert K. Buhrke, Andrew M. Collins, Jr., James R. Hannon, L. Thomas McNamara and Olsen will be $180,000 and $135,000, respectively. Messrs. Mack and Olsen may receive annual discretionary bonuses and salary increases and areRegina R. Miller. The agreements generally provide that:
if the executive terminates his or her employment for any reason during the 12 month period immediately following a change of control of Hinsbrook; or
Hinsbrook Bank & Trust terminates the executive’s employment for any reason other than “cause,” or the executive voluntarily terminates his or her employment for “good reason” during the 24 month period immediately following a change of control,
then the executive is entitled to participate incertain payments from Hinsbrook Bank & Trust based on a multiple of the executive’s salary, and Hinsbrook Bank & Trust is required to continue to provide benefits for a period following termination including, among others, health, life, long term care and disability insurance benefits for the executive and his or her eligible dependents. The benefits provided under the agreements generally include the payment of all accrued compensation through the date of termination, a pro rata payment of the then current bonus cycle, a lump sum severance payment ranging from 1.5 to 3 times salary and the continuation of benefits for a period ranging from 18 to 36 months (through age 65 for Mr. McNamara). Upon the termination of the executive’s employment described above, the executive is required to maintain confidential the matters of Hinsbrook and return any employee insurance and fringe benefit programs of Wintrust, including the Wintrust 1997 Stock Incentive Plan. Stay Bonus Agreements. At the same time as the execution ofall confidential materials.
     Pursuant to the merger agreement, Town Bankshares also entered into a stay bonus agreement with eachthe change of Jay C. Mack and Jeffrey A. Olsen. The stay bonuscontrol agreements provide for the payment of a stay bonus of $330,000 to Mr. Mack and $220,000 to Mr. Olsen contingent on (1) the execution by each executive officer of his employment agreement with Wintrust, (2) the execution by each executive officer of a release for the benefit of Town Bankshares and (3) the closing of the merger. One-half of each stay bonus payment will be payable onterminated immediately prior to the closing dateeffective time of the merger and Hinsbrook Bank & Trust will make payments to the other half will be payable onrespective individuals generally equal in value to the later ofpayments which would have been received had the 60th-day following the closing date or January 2, 2005 if the executive officer continues to be employed under the terms of his employment agreement as of such date unless involuntarily or constructively terminated by Wintrust prior to such date. Amendments to Deferred Compensation Agreements. Town Bank had previously entered into deferred compensation agreements with 12 officers and key employees, including Jay C. Mack, Jeffrey A. Olsen and Roger L. Jensen, Town Bankshares' Vice President - Commercial Lending and a director of Town Bankshares. Each of these deferred compensation agreements had originally provided that upon termination of employment for any reason other than by Town Bank for cause following a "change of control" (which would include the merger), such person would be entitled to payment of the greater of such person's deferred account balance on the date of termination or such person's salary on the date of termination. Each of these officers and key employees entered into an amendment to such person's deferred compensation agreement at the same time as the execution of the merger agreement. With respect to 11 of these persons, the amendments provide that the merger will not constitute a change of control whileagreements been triggered. In consideration for canceling the amendment for the other person provides that the merger will constitute a change of control agreements, the individuals will receive lump sum cash payments in the aggregate of approximately $1,854,000 and thatindividually ranging from approximately $153,000 to $587,000 and each such person would be entitledindividual will provide a release to a payment equalHinsbrook with respect to the greater of such person's deferred account balance on the date of termination or such person's salary on the date of termination upon any termination of employment following the merger but prior to any subsequentterminated change of control of Wintrust other than a voluntary 35 termination by such person or a termination by Town Bank for cause. All ofobligations. Payments and benefits which would have been provided under the amendments provided that upon a termination of employment other than by Town Bank for cause following any subsequent change of control of Wintrust, the officer or key employee would be entitledagreements are subject to paymentSection 280G of the sum of such person's deferred account balance onInternal Revenue Code (golden parachute) cut-back limitations in the date of terminationevent that they are deemed excess parachute payments and such person's salary on the date of termination. Fees Payablepayments to the Membersexecutives in consideration of terminating the Special Committee. The boardchange of directors of Town Bankshares formed a special committee to oversee the sale process and the negotiation of the merger agreement with Wintrust. The members of the special committee met over 10 times in connection with this process, and its members expended significant time and effort in connection with the process. The three members of the special committee, William J. Hickmann, Michael J. Pretasky, Sr. and Robert N. Trunzo,control agreements will receive, in the aggregate, fees of $50,000 in connection with their services on the special committee. be similarly limited.

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Continued Director and Officer Liability Coverage. FollowingCoverage. For five years following the effective time, to the extent required by applicable law, Wintrust has agreed to indemnify and hold harmless the current and former directors and officers of Town BanksharesHinsbrook and each of its subsidiariesHinsbrook Bank & Trust for all actions taken by them prior to the effective time of the merger, to the same extent as Town Banksharesthe indemnification currently provided by Hinsbrook and each of its subsidiaries currently provide for indemnification of their officers and directors.Hinsbrook Bank & Trust. Pursuant to the terms of the merger agreement, Wintrust has agreed to provide to each of the directors and officers of Town BanksharesHinsbrook and each of its subsidiaries,Hinsbrook Bank & Trust, for five years following the effective time, insurance coverage against personal liability for actions taken after the effective time of the merger for a periodthat is substantially the same as is currently provided to directors and officers of five years after the effective time. Wintrust's obligation to provide directors' and officers' liability insurance is conditioned on Town Bankshares' and its subsidiaries' insurer maintaining existing coverage after the completion of the merger. If such insurer terminates or declines to continue coverage, Wintrust has agreed to use commercially reasonable efforts to obtain similar coverage. If Wintrust is unable to obtain such similar coverage, Wintrust is obligated to obtain the best coverage available, in its reasonable judgment, for a cost not exceeding a specified maximum dollar amount. VOTING AGREEMENT AllWintrust.
Voting agreement
     On December 5, 2005, all directors and executive officers of Town Bankshares haveHinsbrook, including one executive officer who has since resigned, entered into a voting agreement with Wintrust. Under this agreement, these shareholders have each agreed to vote their respective shares of Town BanksharesHinsbrook common stock: o
in favor of the merger and the transactions contemplated by the merger agreement;
against any action or agreement that would result in a material breach of any term or obligation of Hinsbrook under the merger agreement; and
against any action or agreement that would impede, interfere with or attempt to discourage the transactions contemplated by the merger agreement.
     Furthermore, subject to their fiduciary duties as officers or directors of the merger and the transactions contemplated by the merger agreement; o against any action or agreement that would result in a material breach of any term or obligation of Town Bankshares under the merger agreement; and o against any action or agreement that would impede, interfere with or attempt to discourage the transactions contemplated by the merger agreement. Furthermore,Hinsbrook, each of these shareholders has also agreed not to grant any proxies, deposit any shares of Town BanksharesHinsbrook common stock into a voting trust or enter into any other voting agreement with respect to any shares of Town BanksharesHinsbrook common stock that they own or, without the prior approval of Wintrust, solicit, initiate or encourage any inquiries or proposals for a merger or other business combination involving Town Bankshares.Hinsbrook. The shares subject to the voting agreement represent approximately 16.9%39.4% of Town Bankshares'Hinsbrook’s outstanding shares of common stock on the record date. The voting agreement will terminate upon the earlier of the consummation of the merger or termination of the merger agreement in accordance with its terms. RESTRICTIONS ON RESALE OF WINTRUST COMMON STOCK
Restrictions on resale of Wintrust common stock
     All shares of Wintrust common stock issued to Town Bankshares'Hinsbrook’s shareholders in connection with the merger will be freely transferable, except that shares received by persons deemed to be "affiliates"“affiliates” of Town BanksharesHinsbrook under the Securities Act at the time of the special meeting may be resold only in transactions permitted by Rule 145 under the Securities Act or otherwise permitted under the Securities Act. This proxy statement/prospectus does not cover any resales of the shares of Wintrust common stock to be received by Town Bankshares'Hinsbrook’s shareholders upon completion of the merger, and no person may use this proxy statement/prospectus in connection with any resale. Based on the number of shares of Wintrust common stock anticipated to be received in the merger, it is expected that Rule 145 will not limit the amount of shares that former Town Bankshares 36 Hinsbrook shareholders will be able to sell into the market. Persons who may be deemed affiliates of Town BanksharesHinsbrook for this purpose generally include directors, executive officers, and the holders of 10% or more of the outstanding shares of Town Bankshares'Hinsbrook’s common stock.

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DESCRIPTION OF THE MERGER AGREEMENT
The following is a summary of the material terms of the merger agreement. This summary does not purport to describe all the terms of the merger agreement and is qualified by reference to the complete text of the merger agreement. A copy of the merger agreement which is attached as Annex A to this proxy statement/prospectus and is incorporated by reference into this proxy statement/prospectus. You should read the merger agreement completely and carefully as it, rather than this description, is the legal document that governs the merger. TIME OF COMPLETION
The completiontext of the merger agreement has been included to provide you with information regarding its terms. The terms of the merger agreement (such as the representations and warranties) are intended to govern the contractual rights and relationships, and allocate risks, between the parties in relation to the merger. The merger agreement contains representations and warranties Wintrust and Hinsbrook made to each other as of specific dates. The representations and warranties were negotiated between the parties with the principal purpose of setting forth their respective rights with respect to their obligations to complete the merger. The statements embodied in those representations and warranties may be subject to important limitations and qualifications as set forth therein, including a contractual standard of materiality different from that generally applicable under federal securities laws.
General
     The merger agreement provides for the merger of Hinsbrook with and into Wintrust, with Wintrust continuing as the surviving corporation. After the consummation of the merger, Hinsbrook Bank & Trust will become a wholly owned subsidiary of Wintrust.
Closing and effective time
Closing.The closing of the merger will take place on the fifth business day afterfollowing the day on which the lastsatisfaction or waiver of the conditions to closing set forth in the merger agreement, have been fulfilled or waived, or at another time that both parties mutually agree upon. See “—Conditions to completion of the merger” below for a more complete description of the conditions that must be satisfied or waived prior to closing. The completion of the merger sometimes is referred to in this proxy statement/prospectus as the closing date.
Completion of the Merger.The merger will become effective on the date when the articles of merger filed by the parties with the Illinois Secretary of State are duly filed by the Illinois Secretary of State, or at such later date and time specified in such filing as the parties mutually agree upon. The time at which the merger becomes effective is sometimes referred to in this proxy statement/prospectus as the "effective“effective time." CONSIDERATION TO BE RECEIVED IN THE MERGER
Consideration to be received in the merger
     If the merger is completed, the shares of Town BanksharesHinsbrook common stock which you own immediately before the completion of the merger will be converted into a right to receive cash (a “cash election”), shares of Wintrust common stock (a “stock election”) or a combination of 50% cash and cash. The number50% shares of Wintrust common stock (a “combination election”). For each of your shares of Hinsbrook common stock, you will receive the “per share merger consideration” to be calculated as set forth in the merger agreement. All elections for cash consideration, stock consideration or the combination of cash and stock consideration are subject to proration. For example, if you elect to receive all cash consideration, depending on the elections made by other Hinsbrook shareholders, it is possible that you will receive for eacha portion of the merger consideration in cash and a portion in stock. The same might be true if you elect to receive all stock consideration. For a description of the possible proration of elections, see “— Proration of merger consideration.”
     Subject to possible proration, if you elect to receive all cash consideration, you will receive $41.59 per share in cash. Subject to possible proration, if you elect to receive the merger consideration in all shares of Wintrust common stock, you will receive between 0.680 and 0.846 of a share of Town BanksharesWintrust common stock, that you own--a number referred to asdepending on the "per share stock consideration"--will be determined by dividing $71.00 by the average of the high and low sales price of Wintrust's common stock during a set "pricing period," provided that such average is not higher than $55.34 or less than $41.34. The pricing period is the 10-day trading period ending two trading days before the merger is completed. In effect, the merger agreement provides that the averagesale price of Wintrust common stock usedon the Nasdaq National Market during the 10 trading day period ending on the fourth trading day prior to calculatecompletion of the exchange ratio will not be higher than $55.34 or less than $41.34. When the average pricemerger. If you elect to receive merger consideration consisting of Wintrust common stock is within that range, there is an inverse relationship between the Wintrust average pricecash and the number of Wintrust shares that you will receive. As the average price of Wintrust common stock approaches $55.34, you would receive a lower number of shares of Wintrust common stock, than you wouldwill receive when the average pricecash consideration of Wintrust common stock nears $41.34. If the Wintrust common stock price is within the range, the

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$41.59 per share for one-half of your Hinsbrook shares and the above-described stock consideration for the other half of your Hinsbrook shares. The merger agreement provides that:
The exchange ratio will adjust upward or downward to ensure that the fraction of a share of Wintrust common stock you receive for each share of Hinsbrook common stock that you own will be equal to $41.59 divided by the reference price so long as the reference price is between $49.14 and $61.14. However, the market value of the fraction of a share of Wintrust common stock that you receive in the merger may be greater or less than $41.59, as the trading price of Wintrust common stock on the date the merger is completed may be greater or less than the reference price used to determine the exchange ratio.
If the reference price is less than $49.14, the exchange ratio will no longer adjust upward, and you will receive 0.846 of a share of Wintrust common stock for each share of Hinsbrook common stock that you own. This means that the value of the fraction of a share of Wintrust common stock you will receive will be below $41.59 per share to the extent the market price of Wintrust common stock is below $49.14 when the merger is completed.
If the reference price is greater than $61.14, the exchange ratio will no longer adjust downward, and you will receive 0.680 of a share of Wintrust common stock for each share of Hinsbrook common stock that you own. This means that the value of the fraction of a share of Wintrust common stock you will receive will be above $41.59 per share to the extent the market price of Wintrust common stock is above $61.14 when the merger is completed.
     Hinsbrook may terminate the merger consideration that you receive would be $129.10. Ifagreement if the averagereference price of Wintrust common stock during the 10-day pricingreference period is greaterless than $55.34 per share, then$47.14, and Wintrust does not, within five business days of notice of such termination, notify Hinsbrook of its election to increase either (a) the per share stock consideration will be $71.00 divided by $55.34, or 1.283number of shares of Wintrust common stock to be issued and/or (b) the amount of cash to be paid in exchange for each sharethose Hinsbrook shares subject to stock elections and the stock portion of Town Bankshares common stock, which meanscombination elections, in either case so that the per share valueconsideration received in exchange for such shares of Hinsbrook common stock is equal to the consideration that would be obtained using $47.14 as the reference price.
     The number of shares of Wintrust common stock you will receive in the merger will be greater than it is withinequal the range, as illustrated innumber, rounded down to the table below. Ifnearest whole number, determined by multiplying the average priceexchange ratio by the number of Wintrust common stock during the 10-day pricing period is less than $41.34 per share, then the per share stock consideration will be $71.00 divided by $41.34, or 1.717 shares of Wintrust common stock to be issued for each share of Town Bankshares common stock, which means the per share value of the consideration you will receive in the merger will be less than it is within the range. However, subject to certain conditions, Wintrust may terminate the merger agreement if the average price of Wintrust common stock is greater than $58.34 and Town Bankshares may terminate the merger agreement if the average price of Wintrust common stock is less than $38.34. 37 The following table illustrates the per share value of merger consideration that Town Bankshares shareholders will receive in the merger based on a range of Wintrust common stock prices.
VALUE OF PER SHARE TOTAL PER SHARE WINTRUST AVERAGE PER SHARE STOCK STOCK VALUE OF PER SHARE VALUE OF MERGER STOCK PRICE CONSIDERATION(1) CONSIDERATION(2) CASH COMPENSATION CONSIDERATION ---------------- ---------------- ------------------ ------------------ --------------- $58.34 1.283 $74.85 $58.10 $132.95 57.34 1.283 73.57 58.10 131.67 56.34 1.283 72.28 58.10 130.38 55.34 1.283 71.00 58.10 129.10 54.34 1.307 71.00 58.10 129.10 53.34 1.331 71.00 58.10 129.10 52.34 1.357 71.00 58.10 129.10 51.34 1.383 71.00 58.10 129.10 50.34 1.410 71.00 58.10 129.10 49.34 1.439 71.00 58.10 129.10 48.34 1.469 71.00 58.10 129.10 47.34 1.500 71.00 58.10 129.10 46.34 1.532 71.00 58.10 129.10 45.34 1.566 71.00 58.10 129.10 44.34 1.601 71.00 58.10 129.10 43.34 1.638 71.00 58.10 129.10 42.34 1.677 71.00 58.10 129.10 41.34 1.717 71.00 58.10 129.10 40.34 1.717 69.28 58.10 127.38 39.34 1.717 67.57 58.10 125.67 38.34 1.717 65.85 58.10 123.95 - ---------------------- (1) The numbers in this column represent the number of shares of Wintrust common stock which you will receive for each share of Town BanksharesHinsbrook common stock that you own. (2) Assumes the closing price of Wintrust common stock on the date of the merger is the same as the average price during the pricing period. The actual trading price of Wintrust common stock is subject to market fluctuations, and Town Bankshares shareholders will not be entitled to receive additional shares in the merger if the trading price of Wintrust's common stock on the closing date of the merger is less than the average price during the pricing period.
Instead of issuing a fractional share of Wintrust common stock in connection with payment of the stock consideration, cash will be paid in an amount determined by multiplying the fractional share by the average pricereference price.
     The following table illustrates the per share value of merger consideration that Hinsbrook’s shareholders will receive in the merger based on a range of Wintrust’s common stock prices and based on whether a stock election or a combination election is made. The table is for illustrative purposes only. The actual prices at which Wintrust common stock trades during the pricing period. Stock Options. Optionsreference period will establish the actual reference price and therefore the actual exchange ratio and consideration.
           
    STOCK  
Wintrust CASH ELECTION ELECTION COMBINATION ELECTION
Reference Per Share Cash Per Share Stock Cash Stock Total Per Share
Price Consideration Consideration(1)(2) Consideration Consideration Consideration(1)(2)
$46.00 $41.59  $38.92  $20.795  $19.458  $40.25 
  47.00 41.59 39.76 20.795 19.881 40.68
  48.00 41.59 40.61 20.795 20.304 41.10
  49.00 41.59 41.45 20.795 20.727 41.52
  50.00 41.59 41.60 20.795 20.800 41.60
  51.00 41.59 41.57 20.795 20.783 41.58
  52.00 41.59 41.60 20.795 20.800 41.60
  53.00 41.59 41.61 20.795 20.803 41.60
  54.00 41.59 41.58 20.795 20.790 41.59

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    STOCK  
Wintrust CASH ELECTION ELECTION COMBINATION ELECTION
Reference Per Share Cash Per Share Stock Cash Stock Total Per Share
Price Consideration Consideration(1)(2) Consideration Consideration Consideration(1)(2)
55.00 41.59 41.58 20.795 20.790 41.59
56.00 41.59 41.61 20.795 20.804 41.60
57.00 41.59 41.61 20.795 20.805 41.60
58.00 41.59 41.59 20.795 20.793 41.59
59.00 41.59 41.60 20.795 20.798 41.59
60.00 41.59 41.58 20.795 20.790 41.59
61.00 41.59 41.60 20.795 20.801 41.60
62.00 41.59 42.16 20.795 21.080 41.88
63.00 41.59 42.84 20.795 21.420 42.22
64.00 41.59 43.52 20.795 21.760 42.56
65.00 41.59 44.20 20.795 22.100 42.90
66.00 41.59 44.88 20.795 22.440 43.24
(1)Assumes the closing price of Wintrust’s common stock on the date of the merger is the same as the reference price during the reference period. The actual trading price of Wintrust common stock is subject to market fluctuations, and Hinsbrook shareholders will not be entitled to receive additional shares in the merger if the trading price of Wintrust’s common stock on the closing date of the merger is less than the average price during the pricing period.
(2)The numbers in this column represent the value of the shares of Wintrust common stock which you will receive for each share of Hinsbrook common stock that you own, subject to the assumption in footnote 1.
Proration of Merger Consideration. Despite your election, the merger agreement provides that the actual number of shares that may be converted into the right to purchase Town Banksharesreceive cash consideration, in the aggregate, may not exceed 50% of Hinsbrook’s outstanding common stock (the “Maximum Cash Election”) and the number of shares that may be converted into the right to receive Wintrust common stock (including any shares subject to the stock portion of a combination election), in the aggregate, may not exceed 50% of Hinsbrook’s outstanding common stock (the “Maximum Stock Election”). If, after the results of the election forms are calculated, the number of shares to be converted into cash or Wintrust common stock exceeds either the Maximum Cash Election or the Maximum Stock Election, Wintrust’s exchange agent will, on a pro rata basis, redesignate those shares to reduce the amount of cash or the number of shares in order to achieve the Maximum Cash Election or Maximum Stock Election, as the case may be. Accordingly, the amount of cash and Wintrust common stock you actually receive as part of the merger consideration may be different from your election. Wintrust may, however, taking into account the actual results of all elections, at any time prior to the effective time direct that the redesignation procedures described be waived in whole or in part, in which case the number of shares to be converted into cash or Wintrust common stock may exceed the Maximum Cash Election or Maximum Stock Election, as the case may be, although the redesignation cannot cause the tax consequences to be materially different than as described earlier.
Stock Options. If the merger is completed, each outstanding and unexercised immediatelyoption to purchase Hinsbrook common stock will automatically be converted into an option to purchase shares of Wintrust common stock, exercisable on generally the same terms and conditions that applied before the effective time of the merger will become options to purchase Wintrust common stock.merger. The number of shares of Wintrust common stock subject to the converted stock optionssubstitute Wintrust option will be equal to the number of shares of Town BanksharesHinsbrook common stock subject to Town Bankshares stock optionsthe option immediately prior to the merger, multiplied by the quotient of the aggregate per share merger consideration divided by the average price of Wintrust common stock as of the determination date. We sometimes refer“option exchange ratio,” rounded down to the quotient of the aggregatenearest whole share. The per share merger consideration divided by the average price of the Wintrust common stock as of the determination date as the "option exchange ratio." The exercise price of a converted stockeach substitute Wintrust option will equal the original Town Bankshares stock option's exercise price of the option immediately prior to the merger divided by the option exchange ratio. Except as described above,ratio, rounded down to the nearest whole cent. The “option exchange ratio” is equal to 41.59 divided by the reference price.
Merger consideration election
     With this proxy statement/prospectus, you have been provided with an election form in order to select whether you will receive merger consideration consisting of cash, Wintrust common stock or a converted stock option will havecombination of cash and Wintrust common stock. The completed election form must be received by Wintrust’s exchange agent, Illinois Stock Transfer Company, by 5:00 p.m., central standard time on the same terms and conditions as the original Town Bankshares stock option. All outstanding Town Bankshares stock options will become vested and immediately exercisable atfifth business day before the effective time of

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the merger. EXCHANGE OF CERTIFICATESOnce made, elections are irrevocable. If your election form is not received by this deadline you will be deemed to have elected to receive the combination of cash and Wintrust common stock. See “—Consideration to be received in the merger—Proration of merger consideration.”
Exchange of certificates
     Wintrust has engaged Illinois Stock Transfer Company to act as its exchange agent to handle the exchange of Town BanksharesHinsbrook common stock for the merger consideration and the payment of cash for any fractional share interest. Within five business days after the effective time, the exchange agent will send to each Town Bankshares 38 Hinsbrook shareholder a letter of transmittal for use in the exchange with instructions explaining how to surrender Town BanksharesHinsbrook common stock certificates to the exchange agent. Town BanksharesHinsbrook shareholders that surrender their certificates to the exchange agent, together with a properly completed letter of transmittal, will receive the merger consideration. Town BanksharesHinsbrook shareholders that do not exchange their Town BanksharesHinsbrook common stock will not be entitled to receive the merger consideration or any dividends or other distributions by Wintrust until their certificates are surrendered. After surrender of the certificates representing Town BanksharesHinsbrook shares, any unpaid dividends or distributions with respect to the Wintrust common stock represented by the certificates will be paid. CONDUCT OF BUSINESS PENDING THE MERGER AND CERTAIN COVENANTSpaid without interest.
Conduct of business pending the merger and certain covenants
     Under the merger agreement, Town BanksharesHinsbrook has agreed to certain restrictions on its activities until the merger is completed or terminated. In general, Town BanksharesHinsbrook and its subsidiariesHinsbrook Bank & Trust are required to conduct their business in the usual and ordinary course, consistent with prudent banking practice.
     The following is a summary of the more significant restrictions imposed upon Town Bankshares,Hinsbrook, subject to the exceptions set forth in the merger agreement: o except with respect to the exercise of outstanding options to purchase Town Bankshares common stock, effecting any change in the capitalization or the number of issued and outstanding shares of Town Bankshares or any of its subsidiaries; o paying any dividends or other distributions, except in connection with the ESOP share redemption; o amending its articles of incorporation or by-laws, the charter or by-laws of Town Bank or the organizational documents of the other subsidiaries; o increasing the compensation of the officers or key employees of Town Bankshares or any of its subsidiaries or paying any bonuses unless the amount of the increase or bonus payment does not exceed $10,000 in the aggregate to any individual officer or key employee; o except with respect to the build-out of Town Bank's Madison branch, making any expenditure for fixed assets in excess of $25,000 for any single item, or $100,000 in the aggregate, or entering into any lease for any fixed assets having an annual rental in excess of $25,000; o making or becoming party to a contract, commitment, or transaction, acquiring or disposing of any property or asset, or incurring any liabilities or obligations, other than in the ordinary course of business consistent with prudent banking practice and its current policies; o doing or failing to do anything that will cause a breach or default under any material contract; o making, renewing or restructuring any loan in excess of $1,000,000 other than in the ordinary course of business consistent with prudent banking practice and Town Bank's current loan policies and applicable governmental rules and regulations; o entering into employment, consulting, or similar agreements that cannot be terminated with less than 30 days notice without penalty; o accepting or renewing any brokered deposits to the extent that the total of outstanding brokered deposits at any one time exceeds $60,000,000 in the aggregate; o buying or investing in government securities that have maturities of more than five years and a rating agency rating below "A"; o terminating, curtailing or discontinuing any of its benefit plans; and o changing in any material respect any accounting or recordkeeping procedures, policies or practices. 39
making changes to the charter and by-laws of Hinsbrook and Hinsbrook Bank & Trust;
except with respect to the exercise of outstanding options to purchase Hinsbrook common stock, effecting any change in the capitalization or the number of issued and outstanding shares of Hinsbrook or Hinsbrook Bank & Trust;
except as otherwise set forth in the merger agreement, paying any dividends or other distributions;
except as otherwise set forth in the merger agreement, increasing the compensation of the officers or key employees of Hinsbrook or any of its subsidiaries or paying any bonuses;
making any expenditure for fixed assets in excess of $50,000 for any single item, or $250,000 in the aggregate, or entering into any lease for any fixed assets having an annual rental in excess of $50,000;
making or becoming party to a contract, commitment, or transaction, acquiring or disposing of any property or asset, or incurring any liabilities or obligations, other than in the ordinary course of business consistent with prudent banking practice and its current policies;
doing or failing to do anything that will cause a breach or default under any material contract;
without Wintrust’s prior written consent, making, renewing or restructuring any loan in excess of $1,000,000, except as provided for in the merger agreement;
entering into employment, consulting, or similar agreements that cannot be terminated with less than 30 days notice without penalty;
buying or investing in government securities that have maturities of more than five years and a rating agency rating below “A”;
exceeding, at any time, $65,000,000 in brokered deposits;

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terminating, curtailing or discontinuing any of its benefit plans; and
changing in any material respect any accounting or recordkeeping procedures, policies or practices.
     Wintrust has agreed to file all applications and notices to obtain the necessary regulatory approvals for the transactions contemplated by the merger agreement. Town BanksharesHinsbrook has agreed to cooperate with Wintrust in connection with obtaining the regulatory approvals. Both parties agree: o to use all reasonable and diligent efforts and to cooperate in the preparation and filing of all applications, notices and documents required to obtain regulatory approval and/or consents from governmental authorities for the merger and the merger agreement; o to use reasonable and diligent good faith efforts to satisfy the conditions required to close the merger and to consummate the merger as soon as practicable; o that neither will intentionally act in a manner that would cause a breach of the merger agreement or that would cause a representation made in the merger agreement to become untrue; and o to coordinate publicity of the transactions contemplated by the merger agreement to the media and Town Bankshares' shareholders. Town Bankshares
to use all reasonable and diligent efforts and to cooperate in the preparation and filing of all applications, notices and documents required to obtain regulatory approval and/or consents from governmental authorities for the merger and the merger agreement;
to use reasonable and diligent good faith efforts to satisfy the conditions required to close the merger and to consummate the merger as soon as practicable;
that neither will intentionally act in a manner that would cause a breach of the merger agreement or that would cause a representation made in the merger agreement to become untrue; and
to coordinate publicity of the transactions contemplated by the merger agreement to the media and Hinsbrook’s shareholders.
     Hinsbrook has agreed that it will not and will not permit the Bank to, directly or indirectly, solicit, encourage or facilitate any third-party inquiries or proposals to acquire Town BanksharesHinsbrook and will not participate in any negotiations or discussions regarding a proposal to acquire Town Bankshares.Hinsbrook. However, Town BanksharesHinsbrook may provide information and negotiate with a third party if Town Bankshares'Hinsbrook’s board of directors determines that failure to do so would be inconsistent with its fiduciary duties. Town BanksharesHinsbrook is required under the merger agreement to provide Wintrust notice of any proposal that it receives to acquire Town Bankshares. Town BanksharesHinsbrook.
     Hinsbrook has also agreed to provide Wintrust with certain documents before the closing date, including: o interim financial statements; o prompt notice of any written assertions of dissenters' rights; o reasonable notice of any meetings of the boards and committees of Town Bankshares, Town Bank or Town Investment Corp.; and o certain information regarding the loans in Town Bank's
interim financial statements;
prompt notice of any written assertions of dissenters’ rights;
reasonable notice and minutes of any meetings of the boards and committees of Hinsbrook or Hinsbrook Bank & Trust; and
certain information regarding the loans in Hinsbrook Bank & Trust’s loan portfolio.
     The merger agreement also contains certain covenants relating to employee benefits and other matters pertaining to officers and directors. See "Description of the merger agreement--Employee“—Employee benefit matters"matters” and "Description of the merger--Interests“The merger—Interests of certain persons in the merger." REPRESENTATIONS AND WARRANTIES
Representations and warranties
     The merger agreement contains representations and warranties made by Town BanksharesHinsbrook and Wintrust. These include, among other things, representations relating to: o valid corporate organization and existence; o corporate power and authority to enter into the merger and the merger agreement; o capitalization; o financial statements; o certain tax matters; o absence of material adverse changes; o government approvals required in connection with the merger; 40 o absence of undisclosed investigations and litigation; o compliance with laws; o broker/finder fees; o governmental registrations, licenses, permits, and reports; and o
valid corporate organization and existence;
corporate power and authority to enter into the merger and the merger agreement;
capitalization;
financial statements;
certain tax matters;

46


absence of material adverse changes;
government approvals required in connection with the merger;
absence of undisclosed investigations and litigation;
compliance with laws;
broker/finder fees; and
absence of any breach of organizational documents, law or other agreements as a result of the merger.
     Wintrust also represents and warrants to Town BanksharesHinsbrook in the merger agreement regarding: o compliance with SEC filing requirements; and o filing of necessary reports with regulatory authorities. Town Bankshares
compliance with SEC filing requirements;
filing of necessary reports with regulatory authorities; and
its financial ability to consummate the merger.
     Hinsbrook makes additional representations and warranties to Wintrust in the merger agreement relating to, among other things: o organizational documents and stock records; o
organizational documents, minutes and stock records;
title to real property, personal property and other material assets;
insurance matters;
employee benefits;
environmental matters;
ownership of Hinsbrook Bank & Trust and other subsidiaries;
compliance with, absence of default under and information regarding material contracts;
loans and its allowance for loan losses;
investment securities;
compliance with the Community Reinvestment Act;
conduct of business and maintenance of business relationships;
technology and intellectual property;
absence of undisclosed liabilities; and
affiliate transactions.
Conditions to real property, personal property and other material assets; o insurance matters; o employee benefits; o environmental matters; o ownershipcompletion of Town Bank and the other subsidiaries; o compliance with, absence of default under and information regarding material contracts; o loans and its allowance for loan losses; o investment securities; o compliance with the Community Reinvestment Act; o conduct of business and maintenance of business relationships; o technology and intellectual property; o absence of undisclosed liabilities; and o affiliate transactions. CONDITIONS TO COMPLETION OF THE MERGER merger
Closing Conditions for the Benefit of Wintrust. Wintrust'sWintrust. Wintrust’s obligations are subject to fulfillment of the following conditions: o
the accuracy of representations and warranties of Town BanksharesHinsbrook in the merger agreement as of the closing date, unless the failure to be accurate does not have a material impact on Town Bankshares; o performance by Town Bankshares in all material respects of its agreements under the merger agreement; 41 o the registration statement has been declared effective by the SEC and continues to be effective as of the effective time; o approval of the merger by Town Bankshares' shareholders; o the holders of not more than 10% of the outstanding shares of Town Bankshares common stock give written demand for dissenters' rights in accordance with Wisconsin law; o receipt of all necessary regulatory approvals; o no adverse material change in Town Bankshares since June 14, 2004; o no litigation resulting from the transactions contemplated by the merger agreement; o receipt of certain certificates from Town Bankshares and a legal opinion from Town Bankshares' legal counsel; o execution of an employment agreement by each of Jay C. Mack and Jeffrey A. Olson; o termination of the Town Bank's Employee Stock Ownership Plan, or the ESOP, and completion of the redemption of shares of Town Bankshares common stock in the ESOP; o amendment of certain deferred compensation agreements between Town Bankshares and certain of Town Bank's officers and key employees; and o receipt of necessary consents, permissions and approvals. date;

47


performance by Hinsbrook in all material respects of its agreements under the merger agreement;
the registration statement has been declared effective by the SEC and continues to be effective as of the effective time;
approval of the merger agreement at the special meeting by the holders of at least a majority of the outstanding shares of Hinsbrook common stock entitled to vote;
the holders of not more than 5% of the outstanding shares of Hinsbrook common stock give written demand for appraisal rights in accordance with Illinois law;
receipt of all necessary regulatory approvals;
no material adverse change in Hinsbrook since December 5, 2005;
no threatened or pending litigation resulting from or seeking to enjoin the transactions contemplated by the merger agreement or seeking other relief that Wintrust reasonably believes, subject to certain conditions, would have a material adverse effect on Hinsbrook or its bank subsidiary;
execution of an employment agreement by Jeffrey D. Baker, Andrew M. Collins, Jr., L. Thomas McNamara and Regina R. Miller;
the entry of certain directors and officers of Hinsbrook into voting agreements;
amendment of Hinsbrook’s deferred compensation and deferred fee arrangements;
payment or accrual of an increased purchase price for certain shares of Hinsbrook’s common stock acquired from an individual in August and October of 2005 such that such individual will receive total consideration equal to $41.59 per share; and
receipt of necessary consents, permissions and approvals.
Closing Conditions for the Benefit of Town Bankshares. Town Bankshares'Hinsbrook. Hinsbrook’s obligations are subject to fulfillment of the following conditions: o accuracy of representations and warranties of Wintrust in the merger agreement as of the closing date, unless the failure to be accurate does not have a material impact on Wintrust; o performance by Wintrust in all material respects of their agreements under the merger agreement; o Wintrust's common stock to be issued in the merger shall be approved for trading on the Nasdaq National Market; o approval of the merger by Town Bankshares' shareholders; o receipt of all necessary regulatory approvals; o execution and delivery of articles of merger suitable for filing with the Illinois Secretary of State and the WDFI; o the registration statement has been declared effective by the SEC and continues to be effective as of the effective time; o no litigation resulting from the transactions contemplated by the merger agreement; o no material adverse change in Wintrust since June 14, 2004; o
accuracy of representations and warranties of Wintrust in the merger agreement as of the closing date;
performance by Wintrust in all material respects of their agreements under the merger agreement;
authorization for listing the shares of Wintrust common stock issuable pursuant to the merger agreement on the Nasdaq National Market, subject to notice of final issuance;
receipt of all necessary regulatory approvals;
execution and delivery of articles of merger suitable for filing with the Illinois Secretary of State;
the registration statement has been declared effective by the SEC and continues to be effective as of the effective time;
no threatened or pending litigation resulting from or seeking to enjoin the transactions contemplated by the merger agreement or seeking other relief that Hinsbrook reasonably believes, subject to certain conditions, makes it inadvisable to consummate the merger;
no material adverse change in Wintrust since December 5, 2005; and

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receipt of certain certificates from Wintrust and a tax opinion from Town Bankshares' legalHinsbrook’s special tax counsel that the merger constitutes a “reorganization” within the meaning of Section 368(a) of the Code.
Minimum net worth and a legal opinion from Wintrust's legal counsel; and o receipt of necessary consents, permissions and approvals. 42 MINIMUM NET WORTH AND LOAN LOSS RESERVE REQUIREMENTS CLOSING CONDITIONloan loss reserve requirements closing condition
     Also, as a condition to Wintrust'sWintrust’s obligation to close, as of the closing date: o Town Bankshares' shareholders' equity, after disregarding any adjustments made pursuant to FAS 115, must exceed the sum of (1) $17,400,000, plus (2) any cash receipts and tax benefits recorded by Town Bankshares from the exercise of outstanding options to purchase Town Bankshares common stock, minus (3) fees for attorneys, accountants and other advisors incurred by Town Bankshares in connection with the merger, up to $300,000, minus (4) the amount paid to redeem the ESOP Shares, but not in excess of the sum of $58.10 plus the cash value of the per share stock consideration received by holders of Town Bankshares common stock; and o Town Bankshares may have no more than $6,186,000 in outstanding principal of holding company-level debt (including trust preferred securities)
Hinsbrook’s shareholders’ equity as of the closing date, adjusted to disregard any changes in the “other comprehensive income” account recorded after June 30, 2005, must be equal to or exceed the sum of the following, which we refer to in this proxy statement/prospectus as the “Minimum Adjusted Net Worth,” (1) $40,600,000, plus (2) any cash receipts and tax benefits recorded by Hinsbrook from the exercise of outstanding options to purchase Hinsbrook common stock, minus, on an after-tax basis, as appropriate (3) fees for attorneys, accountants and other advisors incurred by Hinsbrook in connection with the merger, minus (4) change of control payments due to any director or officer of Hinsbrook under existing agreements to terminate such agreements as contemplated in the merger agreement, minus (5) the amount paid by Hinsbrook to the shareholder from whom Hinsbrook repurchased shares of common stock in August and October of 2005; and
Hinsbrook may have no more than $8,000,000 in outstanding holding company-level debt (including any subordinated or senior debt or debentures).
     Additionally, as of the closing date, Town Bank'sHinsbrook Bank & Trust’s reserve for loan losses may not be less than 1%1.00% of its net loans. TERMINATION TheImmediately prior to closing, Hinsbrook may distribute to its shareholders the amount by which its shareholders’ equity exceeds the Minimum Adjusted Net Worth.
Termination
     Wintrust and Hinsbrook may mutually agree to terminate the merger agreement and abandon the merger at any time prior to completion of the merger. Subject to conditions and circumstances described in the merger agreement, either Wintrust or Hinsbrook may be terminated underterminate the merger agreement if, among other things, any of the following circumstances, as set forth in the merger agreement: o at any time by written agreement of Wintrust and Town Bankshares; o by eitheroccur:
the merger is not completed by July 31, 2006 or such later date agreed to by the parties; provided, that the termination date will be extended to August 31, 2005, if the sole impediments to closing are due to delays in receiving regulatory approval from the Federal Reserve or in the SEC declaring the registration statement effective;
the other party if the closing has not occurred by November 30, 2004 or such later date agreed to by the parties; provided, that the termination date will be extended to February 28, 2005 if the sole impediments to closing are due to delays in receiving regulatory approval from the Federal Reserve or the WDFI or in the SEC declaring the registration statement effective; o Town Bankshares receives and accepts a superior proposal for acquisition by a third party; o by Wintrust if Town Bankshares has not satisfied a condition under the merger agreement required to be met by it prior to the closing date, or if it becomes impossible for the other party to satisfy a condition and its inability to satisfy the condition was not caused by the non-breaching party’s failure to meet any of its obligations under the merger agreement and such non-breaching party has not waived such condition; or
Hinsbrook receives and accepts a superior proposal for acquisition by a third party.
     In addition, Hinsbrook may terminate the merger agreement required to be met by Town Bankshares prior toif the closing date, or if it becomes impossible for Town Bankshares to satisfy a conditionreference price of Wintrust’s common stock during the reference period is less than $47.14 and Town Bankshares' inability to satisfy the condition wasWintrust does not, caused by Wintrust's failure to meet anywithin five business days of notice of such termination, notify Hinsbrook of its obligations underelection to increase either (a) the Agreement and Wintrust has not waived such condition; o by Town Bankshares if Wintrust has not satisfied a condition under the merger agreement required to be met by Wintrust prior to the closing date, or if it becomes impossible for Wintrust to satisfy a condition and Wintrust's inability to satisfy the condition was not caused by Town Bankshares' failure to meet anynumber of its obligations under the Agreement and Town Bankshares has not waived such condition; and o by Wintrust, if the average of the high and low sale priceshares of Wintrust common stock duringto be issued or (b) the 10-day trading period ending two trading days beforeamount of cash to be paid in exchange for those Hinsbrook shares subject to the closing date is greater than $58.34, or, by Town Bankshares, ifstock elections and the pricestock portion of Wintrustcombination elections, in either case so that the per share consideration received in exchange for such shares of Hinsbrook common stock (determined inis equal to the same manner) is less than $38.34, subjectconsideration that would be obtained using $47.14 as the reference price.
Termination fee
Termination Fees Payable by Hinsbrook.Hinsbrook has agreed to certain conditions. TERMINATION FEEpay Wintrust may demand a $1,000,000 termination fee from Town Banksharesof $1,000,000 if the merger agreement is terminated under the following circumstances: o

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Wintrust terminates the merger agreement because Hinsbrook breaches its covenant not to solicit an acquisition proposal from a third party;
Hinsbrook terminates the merger agreement upon its receipt and approval of a superior proposal for an acquisition by a third party; or
the merger agreement is terminated (a) by either Wintrust or Hinsbrook because the closing has not occurred by July 31, 2006 or such later date agreed to by the parties (or August 31, 2006, if the sole impediments to closing are due to delays in receiving regulatory approval from the Federal Reserve or in the SEC declaring the registration statement effective) or (b) by Wintrust because Hinsbrook has not satisfied a condition under the merger agreement required to be met by it prior to the closing date, or if it becomes impossible for Hinsbrook to satisfy a condition and its inability to satisfy the condition was not caused by Wintrust’s failure to meet any of its obligations under the merger agreement and Wintrust has not waived such condition, and in each such case, within six months after termination of the merger agreement, Hinsbrook or the Bank consummates or enters into a definitive agreement relating to an acquisition transaction which was made known to any member of Hinsbrook’s board of directors and not disclosed to Wintrust prior to the date of such termination.
     Hinsbrook has agreed to reimburse Wintrust terminates the merger agreement because Town Bankshares breaches its covenant notfor up to solicit an acquisition proposal from a third party; 43 o Town Bankshares terminates the merger agreement upon its receipt$250,000 in out-of-pocket expenses and approval of a superior proposal for an acquisition by a third party; or ocosts if the merger agreement is terminated under the following circumstances:
by Wintrust because Hinsbrook committed a material breach of its material obligations under the merger agreement and such breach is not the result of Wintrust’s failure to comply or perform in all material respects with any of its material obligations under the merger agreement; or
by either party because the closing has not occurred by July 31, 2006 or such later date agreed to by the parties (or August 31, 2006, if the sole impediments to closing are due to delays in receiving regulatory approval from the Federal Reserve or in the SEC declaring the registration statement effective) due to the failure of Wintrust to obtain the necessary regulatory approvals because of matters relating solely to Hinsbrook and Hinsbrook Bank & Trust.
Termination Fees Payable by writtenWintrust.Wintrust has agreed to reimburse Hinsbrook for up to $250,000 in out-of-pocket expenses and costs if the merger agreement is terminated under the following circumstances:
by Hinsbrook because Wintrust committed a material breach of its material obligations under the merger agreement and such breach is not the result of Hinsbrook’s failure to comply or perform in all material respects with any of its material obligations under the merger agreement; or
by either party because the closing has not occurred by July 31, 2006 or such later date agreed to by the parties (or August 31, 2006, if the sole impediments to closing are due to delays in receiving regulatory approval from the Federal Reserve or in the SEC declaring the registration statement effective) due to the failure of Wintrust to obtain the necessary regulatory approvals for any reason other than matters relating solely to Hinsbrook and Hinsbrook Bank & Trust.
Management of Wintrust and Town Bankshares or by either Wintrust or Town Bankshares becauseHinsbrook Bank & Trust after the closing has not occurred by November 30, 2004 (or February 28, 2004, if the sole impediments to closing are due to delays in receiving regulatory approval from the Federal Reserve or the WDFI or in the SEC declaring the registration statement effective); and in each such case, within six months after termination of the merger agreement, Town Bankshares consummates or enters into a definitive agreement relating to an acquisition transaction which was made known to any member of Town Bankshares' board of directors and not disclosed to Wintrust prior to the date of such termination. MANAGEMENT OF WINTRUST AND TOWN BANK AFTER THE MERGER
     After the merger, the Wintrust board of directors will remain the same and the TownHinsbrook Bank & Trust board of directors will likely change to include members of Wintrust'sWintrust’s management. EMPLOYEE BENEFIT MATTERS
Employee benefit matters
     The merger agreement requires Town BanksharesHinsbrook to terminate all of its employee benefit plans, other than its 401(k) plan, health, life and disability insurance plans, and long-term care plan, and deferred compensation agreements (which will be amended pursuant to the merger agreement) and to pay or accrue all liabilities relating to the terminated employee benefit plans prior to closing. Wintrust will assume those plans which Town BanksharesHinsbrook does not terminate and former Town BanksharesHinsbrook employees may continue to participate in those plans until Wintrust terminates the plans or merges them with existing Wintrust plans. Effective as of closing, each full-time Hinsbrook employee will

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become eligible and entitled to participate in Wintrust’s benefit plans on the same terms and conditions as all other U.S. employees of Wintrust. Wintrust reserves the right to amend or terminate these plans and arrangements in accordance with the terms of the plans and arrangements and applicable laws. If Wintrust chooses to terminate any Town BanksharesHinsbrook employee benefit or similar plan after the closing date, employees previously covered under the terminated plan will be eligible to participate in a similar Wintrust benefit plan. TERMINATION OF ESOP AND REDEMPTION OF ESOP SHARES Town Bankshares maintains the ESOP and has allocated 1,449 shares of Town Bankshares' common stock to participants in the plan. The ESOP also holds 6,251 shares of Town Bankshares common stock that are unallocated. As of the effective time of the merger, the interests of all participants in and beneficiaries of the ESOP will fully vest and become nonforfeitable. Pursuant to the merger agreement, Town Bankshares must undertake three actions in connection with the ESOP prior to the effective time of the merger. First, prior to the effective time, it must terminate the ESOP and, as promptly as practicable, request from the Internal Revenue Service a favorable determination letter as to the tax qualified status of the ESOP upon its termination under Section 401(a) of the Internal Revenue Code of 1986. Second, Town Bankshares must redeem for cash, in an amount per share equal to the sum of $58.10 plus the cash value of the per share stock consideration received by Town Bankshares' shareholders, all unallocated shares of Town Bankshares common stock held by the ESOP and all shares of Town Bankshares' common stock allocated to the ESOP accounts of current or former employees of Town Bankshares who participated in or are beneficiaries of the ESOP. Third, Town Bankshares must cause the loan between it and the trust formed under the ESOP to be repaid in full from the cash consideration received pursuant to the redemption of unallocated ESOP shares. Each participant's account will be credited with an amount equal to the number of shares of Town Bankshares common stock allocated to such participant's account multiplied by the ESOP cash redemption price. The ESOP cash redemption price for the unallocated shares of Town Bankshares common stock will be used first to repay the loan from Town Bankshares to the ESOP trust which had a total balance due of approximately $375,100 as of June 30, 2004. Town Bankshares has amended the ESOP to provide that the remainder of the ESOP cash redemption price for the unallocated shares will be allocated to the accounts of the ESOP participants pro rata based on compensation earned between January 1, 2004 and the date of termination of the ESOP. ESOP participants must be employed by Town Bankshares or its subsidiaries as of the date of the termination of the ESOP to share in this allocation. However, to the extent this allocation exceeds certain limitations under the Internal Revenue Code, the amount in excess of such limitations will be allocated to the accounts of all ESOP participants pro rata based on the account balances immediately prior to the redemption. The 44 termination of the ESOP and the redemption of the shares of Town Bankshares common stock in the ESOP will not be effective unless the merger is subsequently completed. Town Bankshares, before the effective time, and Wintrust, after the effective time, must use their respective reasonable and diligent efforts to obtain a favorable final determination letter from the IRS. If, before the effective time, Town Bankshares or, after the effective time, Wintrust reasonably determines that the ESOP cannot obtain a favorable final determination letter from the IRS or that the amounts held in the ESOP cannot be applied, allocated or distributed without causing the ESOP to lose its tax qualified status, then Town Bankshares, if before the effective time, or Wintrust, if after the effective time, must take such action as they reasonably determine with respect to the distribution of benefits to ESOP participants or beneficiaries. However, the assets of the ESOP must be held or paid only for the benefit of ESOP participants and beneficiaries and, in no event, may any portion of the amounts held in the ESOP revert, directly or indirectly, to Town Bankshares, or any of its subsidiaries, or Wintrust, or any of its affiliates. Following termination of the ESOP, subject to receipt of a favorable determination letter from the Internal Revenue Service, each ESOP participant will receive a distribution of the value of his or her account balance under the ESOP. An ESOP participant may elect to have the distribution paid to him or her or directly rolled over to an IRA that he or she establishes or an eligible employer plan that will accept it and hold it for the participant's benefit. If an ESOP participant chooses a direct rollover, the distribution will not be taxed in the current year and no income tax will be withheld. The distribution will be taxed later when the ESOP participant takes it out of the IRA or eligible employer plan. If an ESOP participant chooses to have the payment made directly to him or her, the ESOP participant will receive only 80% of the taxable amount of the distribution, because the ESOP administrator will be required to withhold 20% of the distribution as income tax withholding. If an ESOP participant receives a distribution of the amount, he or she can elect to roll the distribution into an IRA or an eligible employer plan within 60 days after receipt of the distribution. If an ESOP participant makes such an election and wants to roll over 100% of the distribution to an IRA or an eligible employer plan, he or she must find other money to replace the 20% of the taxable portion that was withheld. If an ESOP participant rolls over only the 80% that was received, he or she will be taxed on the 20% that was withheld and that is not rolled over. If the ESOP participant does not roll over any part of the distribution into an IRA or an eligible employer plan within 60 days, the full amount of the distribution will be taxed to the ESOP participant in the year he or she receives the distribution. If the ESOP participant receives the payment before age 59 1/2, he or she may have to pay an additional 10% tax. ESOP participants should consult with their tax advisors before deciding whether to receive the distribution or roll over the distribution into an IRA or an eligible employer plan. EXPENSES
Expenses
     All expenses incurred in connection with the merger agreement will be paid by the party incurring the expenses, except that the fees paid in connection with the filing of the registration statement will be borne by Wintrust, and Wintrust and Town BanksharesHinsbrook have agreed to share equally the cost and expense incurred in connection with printing and mailing the registration statement.proxy statement/prospectus. As more fully described above under “—Termination fee,” Wintrust and Town BanksharesHinsbrook have also agreed to reimburse each other for certain expenses incurred not exceeding $300,000$250,000 in the event the merger is terminated prior to the closing date for certain specified reasons relating to its material breach of the merger agreement. NASDAQ STOCK LISTING Wintrust'sreasons.
Nasdaq stock listing
     Wintrust’s common stock currently is listed on the Nasdaq National Market under the symbol "WTFC."“WTFC.” The shares to be issued to the Town BanksharesHinsbrook’s shareholders as merger consideration also will be eligible for trading on the Nasdaq National Market.
Amendment
     The merger agreement may be amended in writing by the parties.
SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT OF HINSBROOK
     The following table shows, as of April 24, 2006, the beneficial ownership of Hinsbrook common stock of each person who beneficially owns more than 5% of Hinsbrook’s outstanding common stock, of each Hinsbrook director, by each of the executive officer of Hinsbrook and certain executive officers of Hinsbrook Bank & Trust and by all of Hinsbrook’s directors and officers as a group. Other than the directors and executive officers listed below, no person or entity is known to Hinsbrook to be the beneficial owner of more than 5% of the outstanding shares of Hinsbrook common stock. Except as otherwise noted in the footnotes to the table, each individual has sole investment and voting power with respect to the shares of common stock set forth.
         
  Common Stock directly,  
  indirectly or beneficially Percent of
Name(1) owned as of December 31, 2005 Outstanding
     
Neal A. Anderson  141,500(2)  5.12%
Robert K. Buhrke  159,377(3)  5.77%
Jeffrey D. Baker  7,363   * 
Andrew M. Collins, Jr.  96,316(4)  3.49%
James R. Hannon  170,969(5)  6.19%
L. Thomas McNamara  80,586(6)  2.92%
Regina R. Miller  10,222(7)  * 
Daniel Regan  214,784(8)  7.78%
Ying-Yih Wu  180,579(9)  6.54%
         
All directors and executive officers as a group (9 persons)  1,061,696   38.44%

*Indicates that the individual or entity owns less than one percent of Hinsbrook’s common stock.

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(1)The address for each of the directors and executive officers named in the table is c/o Hinsbrook Bancshares, Inc., 6262 South Route 83, Willowbrook, Illinois 60527.
(2)The amount shown for Mr. Anderson includes 59,662 shares of common stock which is owned by a trust over which Mr. Anderson shares voting and investment power.
(3)The amount shown for Mr. Buhrke includes 135,185 shares of common stock which is owned by trusts over which Mr. Buhrke shares voting and investment power and 19,776 shares of common stock held through the Hinsbrook Bank & Trust 401(k) Plan, pursuant to which Mr. Buhrke has shared voting and investment power. The amount shown for Mr. Buhrke also includes 4,416 shares of common stock held by Hinsbrook Bank & Trust as custodian for the benefit of an IRA for Geraldine K. Buhrke, Mr. Burke’s spouse, of which Mr. Buhrke disclaims beneficial ownership.
(4)The amount shown for Mr. Collins includes 23,800 shares of common stock which is owned jointly by Mr. Collins and his spouse, Mrs. Margaret M. Collins, and 1,000 shares of common stock held through the Hinsbrook Bank & Trust 401(k) Plan, pursuant to which Mr. Collins has shared voting and investment power.
(5)The amount shown for Mr. Hannon includes 48,092 shares of common stock held through the Hinsbrook Bank & Trust 401(k) Plan, pursuant to which Mr. Hannon has shared voting and investment power. The amount shown for Mr. Hannon also includes 32,318 shares of common stock owned by his spouse, Gail Hannon, and 5,310 shares of common stock held by Hinsbrook Bank & Trust as custodian for the benefit of the Gail Hannon IRA, of which Mr. Hannon disclaims beneficial ownership..
(6)The amount shown for Mr. McNamara includes 67,354 shares of common stock owned jointly by Mr. McNamara and his spouse, Mrs. Margaret McNamara and 13,232 shares of common stock held through the Hinsbrook Bank & Trust 401(k) Plan, pursuant to which Mr. McNamara has shared voting and investment power.
(7)The amount shown for Ms. Miller includes 10,222 shares of common stock owned jointly with her spouse, Mr. Robert Miller.
(8)The amount shown for Mr. Regan includes 54,166 shares of common stock held through the Daniel R. Regan, Inc. Profit Sharing Trust and 15,906 shares of common stock held by Hinsbrook Bank & Trust as custodian for the benefit of the Daniel R. Regan IRA. The amount shown for Mr. Regan also includes 338 shares of common stock held by Hinsbrook Bank & Trust as custodian for the benefit of an IRA for Barbara Regan, Mr. Regan’s spouse, of which Mr. Regan disclaims beneficial ownership.
(9)The amount shown for Dr. Wu includes 95,519 shares of common stock held through the Wu Family Medical Center, 5,717 shares of common stock held by Hinsbrook Bank & Trust as custodian for the benefit of certain of Dr. Wu’s IRAs and 4,427 shares of common stock held by Hinsbrook Bank & Trust as custodian for the benefit of the Wu Family Medical Center IRA.
The information presented in the table is based on information furnished by the specified persons and was determined in accordance with Rule 13d-3 under the Securities Exchange Act of 1934, as required for purposes of this proxy statement/prospectus. Briefly stated, under that Rule shares are deemed to be beneficially owned by any person or group having the power to vote or direct the vote of, or the power to dispose or direct the disposition of, such shares, or who has the right to acquire beneficial ownership thereof within 60 days. Beneficial ownership for the purposes of this proxy statement/prospectus is not necessarily to be construed as an admission of beneficial ownership for other purposes.
COMPARISON OF SHAREHOLDER RIGHTS The
General
As a shareholder of Hinsbrook, your rights of shareholders of Town Bankshares, a Wisconsin corporation, are governed by Town Bankshares'Hinsbrook’s articles of incorporation and its by-laws, each as well as the Wisconsin Business Corporation Law (the "WBCL").currently in effect. Upon completion of the merger, the rights of Town BanksharesHinsbrook shareholders who receive shares of Wintrust common stock in exchange for their shares of Town BanksharesHinsbrook common stock and become shareholders of 45 Wintrust will be governed by theWintrust’s amended articles of incorporation and amended and restated by-laws, of Wintrust. Wintrust is an Illinois corporation governed by the Illinois Business Corporation Act ("IBCA"), as well as the rules and regulations applying to public companies. Both corporations are incorporated in Illinois and are subject to the Illinois Business Corporation Act, as amended (the “IBCA”).

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The following discussion summarizes material differences between the rights of Town BanksharesHinsbrook and Wintrust shareholders and is not a complete description of all of the differences. This discussion is qualified in its entirety by reference to the WBCL, IBCA and Wintrust'sWintrust’s and Town Bankshares'Hinsbrook’s respective articles of incorporation and by-laws. AUTHORIZED CAPITAL STOCK The authorized capital stock of Town Bankshares consists of 500,000 shares of common stock, par value $0.01 per share, and 50,000 shares of preferred stock, par value $0.01 per share. Wintrust is authorized to issue 20 million shares, without par value, of preferred stock, and 30 million shares, without par value, of common stock. At _____________ ___, 2004, Wintrust had ___________ shares of common stock outstanding. Wintrust has not issued any shares of preferred stock. Issuance of shares of Wintrust's preferred stock would affect the relative rights of the holders of its common stock, depending upon the exact terms, qualifications, limitations and relative rights and preferences, if any, of the shares of the preferred stock as determined by Wintrust's Board of Directors. PAYMENT OF DIVIDENDS The ability of Town Bankshares to pay dividends is governed by the WBCL and its articles of incorporation. Under the WBCL, the board of directors of a Wisconsin corporation may not pay dividends or make distributions if, after giving effect to the dividend or distribution, the corporation would not be able to pay its debts as they become due in the usual course of business or the corporation's total assets would be less than the sum of its total liabilities plus, unless the corporation's articles of incorporation permit otherwise, the amount that would be needed, if the corporation were to be dissolved at the time of the dividend or distribution, to satisfy the preferential rights upon dissolution of shareholders who preferential rights are superior to those receiving the dividend or distribution. The articles of incorporation of Town Bankshares do not differ from the WBCL. The IBCA governs the ability of Wintrust to pay dividends. Under the IBCA, an Illinois corporation may not pay dividends or make other distributions to its shareholders if the distribution would have the effect of making the corporation insolvent or if, after payment of the dividend, the net assets of the corporation would be less than zero or less than the maximum amount payable at the time of distribution to shareholders having preferential rights in the liquidation of the corporation if it were to be liquidated. Wintrust may pay dividends if, as and when declared by its Board of Directors. As noted above, Wintrust's ability to pay dividends is subject to limitations imposed by the IBCA. If Wintrust issues any shares of its preferred stock in the future, the holders of its preferred stock may have a priority over the holders of its common stock with respect to dividends. ADVANCE NOTICE REQUIREMENTS FOR PRESENTATION OF BUSINESS AND NOMINATIONS OF DIRECTORS AT ANNUAL MEETINGS OF SHAREHOLDERS Wintrust's by-laws provide that nominations for the election of directors may be made by its board of directors or by any shareholder entitled to vote for the election of directors, subject to the nomination having been made in compliance with certain notice and informational requirements. Wintrust's by-laws provide that Wintrust must receive written notice of any shareholder director nomination or proposal for business at an annual meeting of shareholders no later than 60 days in advance of the meeting if the date of the meeting is within 30 days preceding the anniversary date of the prior year annual meeting. Notice must be delivered to Wintrust no later than 90 days before the meeting if the meeting is to be held on or after the anniversary date of the previous year's annual meeting. With respect to any other annual or special meeting, the required notice must be received no later than the tenth day following the date that the date of such meeting is publicly announced. Town Bankshares' by-laws provide that, for business to be properly brought before an annual meeting by a shareholder and for a shareholder nomination for the election of directors, the shareholder must give timely written notice to Town Bankshares' Secretary. To be timely, all notices must be received by the Secretary not later than 90 days prior to the anniversary date of the annual meeting of shareholders in the immediately preceding year. 46 QUORUM Town Bankshares' by-laws provide that a majority of its outstanding shares entitled to vote on a matter, in person or by proxy, constitutes a quorum for the taking of action at a meeting of shareholders. Wintrust's by-laws contain essentially the same provision. Like Town Bankshares shareholders, Wintrust shareholders are entitled to one vote for each share owned. ELECTION, CLASSIFICATION AND SIZE OF BOARD OF DIRECTORS Under Town Bankshares' articles of incorporation, its board of directors must consist of not less than four and no more than 15 directors, as may determined by the then authorized number of directors. The number of directors currently authorized is 8. The board of directors is divided into three classes with each class to consist, as nearly as possible, one-third of the total number of authorized directors. Each director is elected to a term ending on the date of the third annual meeting following the annual meeting at which such director was elected. Wintrust's board of directors is divided into three classes. Each class serves a staggered term, with one class or approximately one-third of the total number of directors being elected for a three-year term at each annual meeting of shareholders. Wintrust's by-laws state that the number of directors shall be 14; however, the Board of Directors may increase or decrease that number so long as there are not less than six directors at any time. The number of directors currently designated by Wintrust is 14. Shareholders do not have any right to cumulate votes in the election of directors. The staggered election of directors ensures that, at any given time, approximately two-thirds of the directors serving will have had prior experience on the board. Staggered terms for directors also moderate the pace of any change in the board by extending the time required to elect a majority of directors from one to two years. It would be impossible, assuming no resignations or removals of directors, for Wintrust's shareholders to change a majority of the directors at any annual meeting should they consider such a change desirable, unless this provision of Wintrust's articles of incorporation is amended by action of at least 85% of Wintrust's voting shares. REMOVAL OF DIRECTORS Town Bankshares' directors may be removed, but only for cause and only by the affirmative vote of the holders of a majority of outstanding shares entitled to vote with respect to the election of such director at a meeting of shareholders duly called for such purpose. Wintrust's directors may be removed by shareholders, with or without cause, at a duly called meeting of shareholders by the affirmative vote of the holders of a majority of outstanding shares entitled to vote. FILLING VACANCIES ON THE BOARD OF DIRECTORS Wintrust's by-laws provide that any vacancies and newly created directorships on the board of directors shall be filled for the remainder of the unexpired term exclusively by a majority vote of the directors then in office. Shareholders do not have the right to fill vacancies. Town Bankshares' articles of incorporation provide that any vacancy on the board of directors may be filled by the action of a majority of the remaining directors, even if less than a quorum, or by a sole remaining director. If no director remains in office, any vacancy may be filled by the shareholders. A director elected to fill a vacancy will hold office for the remaining term of directors of the class to which he or she has been elected and until a successor has been elected and qualified. AMENDMENT OF ARTICLES OF INCORPORATION AND BY-LAWS Generally, Town Bankshares' articles of incorporation may be amended by the affirmative vote of a majority of the combined voting power of the then outstanding shares of common stock entitled to vote on the matter. However, amendment of certain provisions of the articles of incorporation requires the affirmative vote of holders of 70% or more of the combined voting power of the then outstanding shares entitled to vote on the matter. These provisions relate to composition of the board of directors and shareholder action by unanimous written consent. 47 Town Bankshares' by-laws may generally be amended or repealed by a majority vote of the board of directors or shareholders. However, amendment of certain provisions of the by-laws requires the affirmative vote of holders of 70% or more of the combined voting power of the then outstanding shares entitled to vote on the matter. These provisions relate to shareholder meetings and indemnification of directors and officers. Notwithstanding, the fact that shareholder action regarding those provisions requires a supermajority vote, the articles of incorporation provide that the board of directors may amend or repeal those provisions of the by-laws without a vote of shareholders. The by-laws also limit the power of the board of directors to adopt or amend certain other provisions of the by-laws. First, the board of directors may not amend or repeal a bylaw provision adopted by the shareholders if the provision limits the ability of the board of directors to do so. Second, the board of directors may not amend or repeal a bylaw provision adopted by the shareholders if the provision fixes a greater or lower quorum requirement or a greater voting requirement for the board of directors than otherwise is provided in the WBCL unless the provision expressly provides that it may be amended or repealed by a specified vote of the board of directors. Any amendment of Wintrust's articles of incorporation must be approved by a majority vote of the board of directors and also by a vote of at least two-thirds of the outstanding shares of common stock. However, amendment of certain provisions of Wintrust's articles of incorporation requires a higher vote of 85% or more of the outstanding shares. These include provisions relating to: prohibiting cumulative voting rights; the prohibition of shareholder action by written consent; indemnification of Wintrust's officers and directors; the number and classification of the board of directors; and the provisions of the by-laws relating to the vote required to amend certain sections of the articles of incorporation. Wintrust's by-laws may be amended only by the board of directors. MERGERS, ACQUISITIONS AND OTHER TRANSACTIONS Under the IBCA, unless a corporation's articles of incorporation provide otherwise, approval by two-thirds of the voting power of the corporation is required for mergers and other transactions involving any sale, lease, exchange or disposition of all or substantially all of its assets or dissolution. Wintrust's articles of incorporation do not specify a different percentage than that required by law, except as discussed below regarding business combinations with certain persons. See "Business combinations with interested shareholders." Under the WBCL, Town Bankshares may sell, lease, exchange or otherwise dispose of substantially all of its property and may merge or enter into a share exchange with another entity only if the transaction is approved by a majority of all votes entitled to be cast at a meeting for the purpose of voting on the transaction. BUSINESS COMBINATIONS WITH INTERESTED SHAREHOLDERS As a public company, Wintrust is governed by the provisions of Section 7.85 of the IBCA which applies to a transaction with an "Interested Shareholder" (as defined below) (the "IBCA fair price provision"). Fair price provisions are designed to impede two-step takeover transactions which might otherwise result in disparate treatment of Wintrust's shareholders. Under the IBCA fair price provision, the approval of at least 80% of the shares is required in connection with any transaction involving an Interested Shareholder except (i) in the cases where the proposed transaction has been approved in advance by a majority of those members of the corporation's board of directors who are unaffiliated with the Interested Shareholder and were directors prior to the time when the Interested Shareholder became an Interested Shareholder or (ii) if the proposed transaction meets certain conditions set forth therein which are designed to afford the shareholders a fair price in consideration for their shares, in which case approval of only a majority of the outstanding shares of voting stock is required. The term "Interested Shareholder" is defined in the IBCA to include any individual, corporation, partnership or other entity (other than the corporation or any subsidiary) which owns beneficially or controls, directly or indirectly, 15% or more of the outstanding shares of the corporation's voting stock or is an affiliate or associate of the corporation and was the owner of 15% or more of the outstanding voting stock of the corporation at any time within the three year period immediately before the date on which the determination whether the person is an Interest Shareholder is sought. Town Bankshares has opted to be subject to a parallel provision of the WBCL. The WBCL defines a "business combination" as including a merger or a share exchange, sale of assets, issuance of stock or rights to 48 purchase stock and other transactions with interested shareholders. Under the WBCL, an "interested shareholder" is a person who beneficially owns, directly or indirectly, 10% of the outstanding voting stock of a corporation or who is an affiliate or associate of the corporation and beneficially owned 10% of the voting stock within the last three years. During the initial three-year period after a person becomes an interested shareholder in a Wisconsin corporation, with some exceptions, the WBCL prohibits a business combination with the interested shareholder unless the corporation's board of directors approved the business combination or the acquisition of the stock prior to the acquisition date. Following this three-year period, the WBCL also prohibits a business combination with an interested shareholder unless: o the board of directors approved the business combination or the acquisition of the stock prior to the acquisition date, o the business combination is approved by a majority of the outstanding voting shares not owned by the interested shareholder, o the consideration to be received by shareholders meets the "fair price" and form requirements of the statute, or o the business combination is of a type specifically excluded from the coverage of the statute. As allowed by the WBCL, Town Bankshares has opted to be subject to Sections 180.1130 through 180.1134 of the WBCL which govern mergers or share exchanges between public Wisconsin corporations and significant shareholders and sales of all or substantially all of the assets of public Wisconsin corporations to significant shareholders. These transactions must be approved by 80% of all shareholders and two-thirds of shareholders other than the significant shareholder, unless the shareholders receive a statutory fair price. This is intended to insure that shareholders in a second step merger, share exchange or asset sale receive at least what shareholders received in the first step. Section 180.1130 of the WBCL defines a "significant shareholder" as the beneficial owner, directly or indirectly, of 10% or more of the voting power of the outstanding voting shares, or an affiliate of the Wisconsin corporation that beneficially owned 10% or more of the voting power of the then- outstanding shares within the last two years. The WBCL specifically provides that a person is not a "beneficial owner" of securities for purposes of Section 180.1130 of the WBCL solely because of the existence of an agreement between the person and a record or beneficial owner of such securities under which the owner agrees to vote the securities in favor of a proposed merger, share exchange or sale, lease, exchange or other disposition of assets. LIMITATIONS ON DIRECTORS' LIABILITY Wintrust's articles of incorporation provides that no director will be personally liable to the corporation or any of its shareholders for monetary damages for any breach of fiduciary duty except, as required by the IBCA, as follows: o for breach of duty of loyalty to the corporation or the shareholders; o for acts and omissions not in good faith or which involved intentional misconduct or a knowing violation of law; o for deriving an improper personal benefit from a transaction with the corporation; or o under Section 8.65 of the IBCA, which creates liability for unlawful payment of dividends and unlawful stock purchases or redemptions. Under the WBCL, a director will not be liable to a corporation, its shareholders or any person asserting rights on behalf of the corporation or its shareholders for damages or other monetary liabilities arising from a breach of, or failure to perform, any duty resulting solely from his or her status as a director, unless the person asserting liability proves that the breach or failure to perform constitutes one of the following: o a willful failure to deal fairly with the corporation or its shareholders in connection with a matter in which the director has a material conflict of interest; 49 o a violation of criminal law, unless the director had reasonable cause to believe that his or her conduct was lawful or no reasonable cause to believe that his or her conduct was unlawful; o a transaction from which the director derived an improper personal benefit; or o willful misconduct. INDEMNIFICATION The by-laws of Town Bankshares provide two types of indemnification to its directors and officers. The first type is indemnification for successful defense of claims and the second type covers indemnification for all other claims. As to the first type, within 20 days after receipt of a written request, Town Bankshares must indemnify a director or officer, to the extent that he or she has been successful on the merits or otherwise in the defense of a proceeding, for all reasonable expenses incurred in the proceeding if the director or officer was a party to the proceeding by virtue of his or her status as a director or officer of the corporation or a wholly-owned subsidiary of the corporation. As to the second type, Town Bankshares must indemnify a director or officer against liabilities and expenses incurred by the director or officer in a proceeding to which the director or officer was a party because he or she was a director or officer of the corporation or one of its wholly-owned subsidiaries, unless liability was incurred because the director or officer breached or failed to perform a duty he or she owes the corporation and the breach or failure to perform constitutes any of the following: o a willful failure to deal fairly with the corporation or its shareholders in connection with a matter in which the director has a material conflict of interest; o a violation of criminal law, unless the director had reasonable cause to believe that his or her conduct was lawful or no reasonable cause to believe that his or her conduct was unlawful; o a transaction from which the director derived an improper personal benefit; or o willful misconduct. Unless otherwise provided by a written agreement between a director or officer and the corporation, the director or officer seeking indemnification must select one of the following means for determining his or her right to indemnification: (1) By a majority vote of a quorum of the board of directors consisting of directors not at the time parties to the same or related proceedings. If a quorum of disinterested directors cannot be obtained, by majority vote of a committee duly appointed by the board of directors and consisting solely of two or more directors who are not at the time parties to the same or related proceedings. Directors who are parties to the same or related proceedings may participate in the designation of members of the committee. (2) By independent legal counsel selected by a quorum of the board of directors or its committee in the manner prescribed in (1) above or, if unable to obtain such a quorum or committee, by a majority vote of the full board of directors, including directors who are parties to the same or related proceedings. (3) By a panel of three arbitrators consisting of one arbitrator selected by those directors entitled under (2) above to select independent legal counsel, one arbitrator selected by the director or officer seeking indemnification and one arbitrator selected by the two arbitrators previously selected. (4) By an affirmative vote of shares represented at a meeting of shareholders at which a quorum of the voting group entitled to vote thereon is present. Shares owned by, or voted under the control of, persons who are at the time parties to the same or related proceedings, whether as plaintiffs or defendants or in any other capacity, may not be voted in making the determination. 50 (5) By a court as set forth in the by-laws. (6) By any other method provided for in any additional right to indemnification permitted under the by-laws. In any determination described above, the burden of proof is on the corporation to prove by clear and convincing evidence that indemnification should not be allowed. If it is determined that indemnification is required, the corporation shall pay all liabilities and expenses not prohibited by the by-laws within ten days after receipt of the written determination. The corporation shall also pay all expenses incurred by the director or officer in the determination process described above. Except as provided otherwise by written agreement between the director officer and the corporation, a director or officer who is a party to a proceeding may apply for indemnification to the court conducting the proceeding or to another court of competent jurisdiction. Application shall be made for an initial determination by the court under (5) above or for review by the court of an adverse determination under (1), (2), (3), (4) or (6) above. If the court determines that the director or officer is entitled to indemnification, the corporation shall pay the director's or officer's expenses incurred to obtain the court-ordered indemnification. Under the IBCA, a corporation may indemnify its directors, officers, employees and certain other individuals against expenses, including attorneys' fees, judgments, fines and amounts paid in settlement in connection with actions, suits or proceedings arising because of the person's relationship to the corporation. The indemnification generally will cover expenses regardless of whether it is a civil, criminal, administrative or investigative proceeding if the individual acted in good faith and in a manner he or she reasonably believed to be in, or not opposed to, the best interest of the corporation and, in the case of a criminal proceeding, had no reasonable cause to believe his or her conduct was unlawful. A similar standard applies in an action or suit by or in the right of the corporation, but extends to only expenses, including attorneys' fees, incurred in defense of the proceeding. In these cases, court approval is required before there can be any indemnification when the person seeking indemnification has been found liable to the corporation. To the extent a person otherwise eligible for indemnification is successful on the merits or otherwise in defense of any action, suit or proceeding described above, indemnification for expenses, including attorneys' fees, actually and reasonably incurred is required under the IBCA. Wintrust's

Wintrust Shareholder RightsHinsbrook Shareholder Rights
Authorized
Capital
Stock:
Wintrust is authorized to issue 60 million shares, without par value, of common stock, and 20 million shares, without par value, of preferred stock. On April 6, 2006, Wintrust had 24,243,388 shares of common stock outstanding. Wintrust has not issued any shares of preferred stock. Issuance of shares of Wintrust’s preferred stock would affect the relative rights of the holders of its common stock, depending upon the exact terms, qualifications, limitations and relative rights and preferences, if any, of the shares of the preferred stock as determined by Wintrust’s board of directors.Hinsbrook is authorized to issue 10 million shares of common stock, par value $0.05 per share.

On the record date Hinsbrook had 2,761,723 shares of common stock outstanding.
Rights of Preferred Shareholders:
Wintrust has not issued any of its authorized preferred stock.Hinsbrook is not authorized to issue preferred stock.
Dividends:
Subject to any rights of holders of preferred stock if such stock is ever issued, Wintrust may pay dividends if, as and when declared by its board of directors from any funds legally available therefor.Hinsbrook may pay dividends if, as and when declared by its board of directors from any funds legally available therefor.
Number of Directors, Classification:
The Wintrust board of directors currently consists of fourteen (14) members. Wintrust’s by-laws provide, however, that the number may be increased or decreased (provided the number is never less than nine (9)) by an amendment of the by-laws by the shareholders, or by a resolution adopted by the majority of the board of directors.The Hinsbrook board of directors currently consists of five (5) members. Hinsbrook’s articles of incorporation provide that its board of directors must consist of not less than three (3) and no more than ten (10) directors, as may be established by resolution of the then-current board.
Wintrust’s board of directors is divided into three classes, with each class consisting of approximately one-third of the total number of directors. Directors are elected for three-year terms, with one class of directors up for election at each annual meeting of shareholders.Hinsbrook’s board of directors consists of a single class of directors.
Election of Directors:
Each Wintrust shareholder is entitled to vote the number of shares owned by such shareholder for as many persons as there are directors to be elected.Each Hinsbrook shareholder is entitled to vote the number of shares owned by such shareholder for as many persons as there are directors to be elected.
The Wintrust by-laws provide that no cumulative voting is permitted.The Hinsbrook by-laws provide that no cumulative voting is permitted.
Removal of Directors:
A Wintrust director may be removed at a
shareholders’ meeting, with or without
A Hinsbrook director may be removed at a shareholders’ meeting, with or without

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Wintrust Shareholder RightsHinsbrook Shareholder Rights
cause, by the affirmative vote of a majority of the outstanding shares entitled to vote.cause, by the affirmative vote of a majority of the outstanding shares entitled to vote.
Call of Special Meeting of Directors:
Wintrust’s by-laws provide that a special meeting of the board of directors may be called by or at the request of the chairman of the board, president or a majority of then-acting directors.Hinsbrook’s by-laws provide that a special meeting of the board of directors may be called by or at the request of the chairman of the board, the president, secretary or any two directors.
Limitation on
Director Liability:
Wintrust’s articles of incorporation provide that no director will be personally liable to the corporation or any of its shareholders for monetary damages for any breach of fiduciary duty except for liability:Hinsbrook’s articles of incorporation, provide that a director will not be liable to the corporation or any of its shareholders for monetary damages for breach of fiduciary duty except for liability:
      for any breach of the director’s duty of loyalty to the corporation or its shareholders;
      for any breach of the director’s duty of loyalty to the corporation or its shareholders;
     for acts and omissions not in good faith or that involve intentional misconduct or a knowing violation of law;
     for acts and omissions not in good faith or that involve intentional misconduct or a knowing violation of law;
     under Section 8.65 of the IBCA (which creates liability for unlawful payment of dividends and unlawful stock purchases or redemptions), as it exists or hereafter may be amended; or
     under Section 8.65 of the IBCA (which creates liability for unlawful payment of dividends and unlawful stock purchases or redemptions), as it exists or hereafter may be amended; or
     for any transaction from which the director derived an improper benefit.
     for any transaction from which the director derived an improper personal benefit.
Indemnification:
Wintrust’s articles of incorporation and by-laws provide that the corporation has the power to indemnify its directors, officers, employees and agents to the fullest extent authorized by the IBCA.Hinsbrook’s by-laws provide for indemnification of its officers and directors to the fullest extent authorized by the IBCA.
The by-laws provide that, to the extent a present or former director, officer or employee of the corporation (or of any subsidiary, as the case may be) has been successful on the merits or otherwise in defense of any proceeding, or in connection with any claim, issue or matter therein, the corporationshall indemnify the director or officer against expenses actually and reasonably incurred by him in connection with such proceeding to the extent he was a party as a result of being a director, officer or employee, provided that such person acted in good faith and in a manner he or she reasonably believed to be in, or notThe by-laws provide that, to the extent a present or former director or officer has been successful on the merits or otherwise in defense of any proceeding, or in connection with any claim, issue or matter therein, the corporationshallindemnify the director or officer against expenses actually and reasonably incurred by him in connection with such proceeding to the extent he was a party as a result of being a director or officer. The corporation shall not indemnify, however, if the liability was incurred because the director or officer breached or failed to perform a duty he owes the corporation and the breach or failure to perform constitutes any of the

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Wintrust Shareholder RightsHinsbrook Shareholder Rights
opposed to, the best interests of the corporation. The boardmay indemnify agents of the corporation in this context.following:
     a willful failure to deal fairly with the corporation or its shareholders in connection with a matter in which the director or officer has a material conflict of interest;
     a violation of criminal law, unless the director or officer had reasonable cause to believe his conduct was lawful or no reasonable cause to believe it was unlawful;
     a transaction from which the director or officer derived an improper personal profit; or
     willful misconduct.
In addition to the mandatory indemnification describe above, the by-laws provide that the board of directorsmay, in its sole discretion, provide indemnification to an employee or agent of the corporation who is not a director or officer in connection with any proceeding in which the employee or agent was a defendant because of his actions as an employee or agent, provided that the employee or agent acted in good faith and in a manner he reasonably believed to be in and not opposed to the best interests of the corporation.
Call of Special Meetings of Shareholders:
Wintrust’s by-laws provide that a special meeting of the shareholders may be called by the board of directors, the president or the holders of not less than one-fifth of all the outstanding shares entitled to vote on the matter for which the meeting is called, for the purpose or purposes stated in the call of the meeting.

Written notice stating the place, date, hour and purpose(s) of the special meeting must be delivered, either personally or by mail, not less than ten (10) nor more than sixty (60) days before the date of the meeting.
Hinsbrook’s by-laws provide that a special meeting of the shareholders may be called by the chairman of the board, president or the board of directors, and shall be called by the president at the written request (a) of the holders of not less than one-tenth of all shares of the corporation entitled to vote at the meeting, or (b) of one-third, but in no event less than two, of the directors then in office.

Written notice stating the place, day, hour and purpose(s) of the special meeting must be delivered, either personally or by mail, not less than ten (10) nor more than sixty (60) days before the date of the meeting.
Quorum of Shareholders:
Wintrust’s by-laws provide that a majority of the shares entitled to vote on a matter, present in person or represented by proxy, constitutes a quorum at any meeting of shareholders.Hinsbrook’s by-laws provide that a majority of the shares entitled to vote on a matter, present in person or represented by proxy, constitutes a quorum at any meeting of shareholders.

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Wintrust Shareholder RightsHinsbrook Shareholder Rights
Shareholders
Proposals:
Wintrust’s by-laws provide that for a shareholder to properly bring business before an annual or special meeting of shareholders, written notice of such shareholder’s intent to make such proposal(s) must be given by personal delivery or U.S. mail postage prepaid and received by the secretary of the corporation no later than the following dates: (i) with respect to an annual meeting of shareholders, sixty (60) days in advance of such meeting if such meeting is to be held on a day which is within thirty (30) days preceding the anniversary date of the previous year’s annual meeting or ninety (90) days in advance of such meeting if such meeting is to be held on or after the anniversary of the previous year’s annual meeting; and (ii) with respect to any other annual or special meeting of shareholders, the close of business on the tenth (10th) day following the date of public disclosure of the date of such meeting.Hinsbrook’s by-laws do not contain any restrictions on the making by its shareholders of proposals for annual or special meetings.
A shareholder’s notice to the secretary shall set forth as to each item of business the shareholder proposes to bring before such meeting: (a) a brief description of the business desired to be brought before the meeting; (b) the name and record address of the shareholder who proposes such business; (c) the number of shares of stock of the corporation beneficially owned by such shareholder; and (d) a description of all arrangements or understandings between the shareholder and any other person(s) pursuant to which the proposal or proposals are to be made by the shareholder and any material interest of the shareholder in the business being proposed.
Shareholder Action
by Written
Consent:
Wintrust’s articles of incorporation and by-laws provide that its shareholders are not permitted to act by written consent. Any action required or permitted to be taken at a meeting of the shareholders must be effected at a duly called annual or special meeting.Hinsbrook’s by-laws provide that any action required to be taken at a meeting of the shareholders, or any other action which may be taken at a meeting of the shareholders, may be taken without a meeting if a consent in writing, setting forth the action so taken, is signed by the holders of outstanding shares having not less than the minimum number of votes that would be necessary to authorize or take such action at a meeting at which all shares entitled to vote thereon were present and voting.

56


Wintrust Shareholder RightsHinsbrook Shareholder Rights
Appointment and Removal of Officers:
Wintrust’s by-laws provide that the officers shall be elected annually by the board of directors at the first meeting of the board of directors held after each annual meeting of the shareholders. Each officer will hold office until his successor is duly elected or until his prior death, resignation or removal.Hinsbrook’s by-laws provide that the officers shall be elected annually by the board of directors at the first meeting of the board of directors held after each annual meeting of the shareholders. Each officer will hold office until his successor is duly elected or until his prior death, resignation or removal.
Any officer may be removed by the board of directors whenever in its judgment the best interests of the corporation will be served thereby.Any officer may be removed by the board of directors whenever in its judgment the best interests of the corporation will be served thereby.
Required Vote for
Certain Transactions
The Wintrust articles of incorporation do not specifically discuss transactions involving merger, consolidation, or sale, lease or exchange of all or substantially all of the property or assets of the corporation. But the applicable IBCA provisions state that such a transaction must be approved by two-thirds of the outstanding shares of stock entitled to vote on the matter. The corporation may, however, without approval by a vote of shareholders, merge into itself any corporation of which at least ninety percent (90%) of the outstanding shares of each class is owned by the corporation.As provided in the Hinsbrook articles of incorporation, the following transactions require the affirmative vote of the holders of at least eighty percent (80%) of the outstanding shares of stock entitled to vote on the matter:

     any merger or consolidation of the corporation with one or more other corporations (regardless of which is the surviving corporation); or


     any sale, lease or exchange of all or substantially all of the property and assets of the corporation to or with one or more other corporations, persons or other entities.
However, the affirmative vote of the holders of a simple majority of the outstanding shares of stock entitled to vote on either of these matters shall apply to any such transaction which is approved by resolution adopted by the affirmative vote of the majority of the entire board of directors in office at the time.
In addition, the articles of incorporation provide that the corporation may merge into itself any corporation of which at least ninety percent (90%) of the outstanding shares of each class is owned by the corporation, without approval by a vote of shareholders of either corporation.
Amendment to Charter and By-laws:
Otherwise, as provided by the IBCA or discussed below, the articles of incorporation may be amended by the affirmative vote of at least two-thirds of the shares entitled to vote on the proposal after the board of directors has passed a resolution by majority vote setting forth the proposed amendment and directing that itHinsbrook’s articles of incorporation may be amended, altered, changed or repealed by the affirmative vote of at least two-thirds of all outstanding shares of stock entitled to vote on such amendment; provided, however, that in the case of an amendment relating to the tenure and number of directors, repurchase rights, mergers,

57


Wintrust Shareholder RightsHinsbrook Shareholder Rights
be submitted to a vote at a shareholders’ meeting.

An amendment to the articles of incorporation that relates to certain provisions, including, the prohibition of cumulative voting, shareholder purchase rights, the prohibition of shareholder action by written consent, the number and classification of the board of directors, director liability, indemnification and insurance, number, tenure and qualification of directors or the amendment process, must be approved by the affirmative vote of the holders of eighty-five percent (85%) or more of the voting power of the then-outstanding shares of stock entitled to vote generally in the election of directors, voting together as a single class.

Otherwise, as provided by the IBCA, the articles of incorporation may be amended by the affirmative vote of at least two-thirds of the shares entitled to vote on the proposal after the board of directors has passed a resolution by majority vote setting forth the proposed amendment and directing that it be submitted to a vote at a shareholders’ meeting.

The power to make, alter, amend or repeal the by-laws of the corporation is vested in the shareholders or the board of directors by a resolution adopted by a majority of the board of directors.
consolidations, the sale, lease or exchange of all or substantially all of the corporation’s property and assets, or the amendment process, the affirmative vote of the holders of at least eighty percent (80%) of the outstanding shares of stock entitled to vote on such amendment is required.

However, the affirmative vote of the holders of a simple majority of the outstanding shares entitled to vote is sufficient for any amendment which is approved by resolution of a majority of the board of directors.

Hinsbrook’s by-laws may be amended, altered, changed or repealed by the affirmative vote of at least two-thirds of all outstanding shares of stock entitled to vote on such amendment; provided, however, that in the case of an amendment relating to the tenure and qualifications of directors, the affirmative vote of the holders of at least eighty percent (80%) of the outstanding shares of stock entitled to vote on such amendment is required. However, the affirmative vote of the holders of a majority of the outstanding shares entitled to vote is sufficient for any amendment which is approved by resolution of a majority of the board of directors.

The by-laws may also be altered, amended or repealed and new by-laws may be adopted by the affirmative vote of a majority of the board of directors present at any meeting at which a quorum is in attendance; provided, however, that no by-law adopted by the shareholders may be amended or repealed by the board of directors if the by-law adopted by the shareholders so provides.
Shareholder
Rights
Plan:
None.None.
Preemptive Rights:
None.None.
Certain anti-takeover effects of Wintrust’s articles and by-laws generally provide for the same indemnification as the IBCA, including the advancement of expenses to the extent permitted by law. ACTION BY SHAREHOLDERS WITHOUT A MEETING Under the IBCA, unless the articles of incorporation provide otherwise, shareholders may act by written consent if the consent is signed by shareholders who collectively own the number of shares that would have been required to take action at an actual shareholder meeting. Wintrust's articles of incorporation and by-laws provide that its shareholders are not permitted to act by written consent. All action required or permitted to be taken by Wintrust's shareholders must be effected at a duly called annual or special meeting of its shareholders. Town Bankshares' articles of incorporation provide that shareholders may not act without a meeting unless the unanimous written consent of all shareholders is obtained. SPECIAL MEETINGS OF SHAREHOLDERS Town Bankshares' by-laws state that a special meeting may be called only by the board of directors pursuant to a resolution adopted by three-quarters of the entire board of directors and must be called by the board of directors upon the demand of the holders of record of shares representing 10% of all shares entitled to be cast on any issue proposed to be considered at the special meeting. Wintrust's by-laws state that special meetings only may be called by the chairman of the board of directors or the president of Wintrust. 51 PREEMPTIVE RIGHTS Under both the WBCL and the IBCA, preemptive rights will not be available unless a corporation's articles of incorporation specifically provide for these rights. Neither Wintrust's nor Town Bankshares' articles of incorporation provide for preemptive rights. Accordingly, Wintrust shareholders are not entitled to preemptive rights with respect to any shares that Wintrust may issue in the future. DISSENTERS' RIGHTS Under the WBCL, the rights of dissenting shareholders to obtain the fair value for their shares may be available in connection with a merger or consolidation in certain situations. Dissenters' rights are available to Town Bankshares shareholders in connection with the merger because the merger requires shareholder approval. For a description of dissenters' rights, see "Special meeting of Town Bankshares shareholders--Dissenters' rights." CERTAIN ANTI-TAKEOVER EFFECTS OF WINTRUST'S ARTICLES AND BY-LAWS AND ILLINOIS LAWIllinois law
     Certain provisions of Wintrust'sWintrust’s articles of incorporation, by-laws and the IBCA may have the effect of impeding the acquisition of control of Wintrust by means of a tender offer, a proxy fight, open-market purchases or otherwise in a transaction not approved by Wintrust'sWintrust’s board of directors.

58


     These provisions may have the effect of discouraging a future takeover attempt which is not approved by Wintrust'sWintrust’s board of directors but which individual Wintrust shareholders may deem to be in their best interests or in which Wintrust shareholders may receive a substantial premium for their shares over then-current market prices. As a result, shareholders who might desire to participate in such a transaction may not have an opportunity to do so. Such provisions will also render the removal of Wintrust'sWintrust’s current board of directors or management more difficult.
     These provisions of Wintrust'sWintrust’s articles of incorporation and by-laws include the following:
     (1) Wintrust'sWintrust’s board of directors may issue additional authorized shares of Wintrust'sWintrust’s capital stock to deter future attempts to gain control of Wintrust, including the authority to determine the terms of any one or more series of preferred stock, such as voting rights, conversion rates, and liquidation preferences. As a result of the ability to fix voting rights for a series of preferred stock, the board has the power, to the extent consistent with its fiduciary duty, to issue a series of preferred stock to persons friendly to management in order to attempt to block a merger or other transaction by which a third party seeks control, and thereby assist the incumbent board of directors and management to retain their respective positions;
     (2) Wintrust'sWintrust’s staggered board is intended to provide for continuity of its board of directors and to make it more difficult and time consuming for a shareholder group to fully use its voting power to gain control of the board of directors without the consent of Wintrust'sWintrust’s incumbent board of directors;
     (3) Wintrust'sWintrust’s articles of incorporation do not provide for cumulative voting for any purpose, and its articles of incorporation and by-laws also provide that any action required or permitted to be taken by its shareholders may be taken only at an annual or special meeting and prohibit shareholder action by written consent in lieu of a meeting;
     (4) Wintrust'sWintrust’s articles of incorporation expressly elect to be governed by the provisions of Section 7.85 of the IBCA, as discussed above. Under the IBCA fair price provision and Wintrust'sWintrust’s articles of incorporation, the approval of at least 80% of its shares is required in connection with any transaction involving an Interested Shareholder, subject to certain exceptions. Fair price provisions are designed to impede a two-step takeover transactions which might otherwise result in disparate treatment of Wintrust'sWintrust’s shareholders; and
     (5) Amendment of Wintrust'sWintrust’s articles of incorporation must be approved by a majority vote of the board of directors and also by a two-thirds vote of the outstanding shares of Wintrust common stock, provided, however, that an affirmative vote of at least 85% of the outstanding voting stock entitled to vote is required to amend or repeal certain provisions of the articles of incorporation, including provisions 52 (a) prohibiting cumulative voting rights, (b) relating to certain business combinations, (c) limiting the shareholders'shareholders’ ability to act by written consent, (d) regarding the number, classification of directors, filling of board vacancies and newly created directorships, (e) indemnification of directors and officers by Wintrust and limitation of liability for directors, and (f) regarding amendment of the foregoing supermajority provisions of Wintrust'sWintrust’s articles of incorporation. Wintrust'sWintrust’s by-laws may be amended only by the board of directors.
     The provisions described above are intended to reduce Wintrust'sWintrust’s vulnerability to takeover attempts and certain other transactions which have not been negotiated with and approved by members of its board of directors. RIGHTS PLAN Wintrust has a shareholders rights plan which could discourage unsolicited or hostile takeover attempts which are not negotiated with its board of directors.
DESCRIPTION OF WINTRUST COMMON STOCK
     The plan discourages such attempts by causing substantial dilution to any person who acquires an amount in excess of a specified percentage of Wintrust's common stock and by making an acquisition of Wintrust, without the consent of its board of directors, prohibitively expensive. Thefollowing description of the rights plan set forth belowcapital stock of Wintrust does not purport to be complete and is qualified, in its entiretyall respects, to applicable Illinois law and provisions of Wintrust’s amended and restated articles of incorporation, as amended, and Wintrust’s by-laws. Wintrust’s amended and restated articles of incorporation and Wintrust’s by- laws are incorporated by reference and will be sent to shareholders of Wintrust and Hinsbrook upon request. See “Where You Can Find More Information.”

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Authorized Capital Stock
     Under its amended and restated articles of incorporation, Wintrust has the descriptionauthority to issue 60 million shares of the rights plan set forth in Wintrust's Registration Statement on Form 8-A dated August 28, 1998. See "Incorporationcommon stock, without par value, and 20 million shares of Certain Information by Reference" on page 54. Each sharepreferred stock, without par value. As of April 6, 2006 there were issued and outstanding 24,243,388 shares of Wintrust common stock. No shares of preferred stock has attached to it a stock purchase right having the terms set forth in a rights agreement between are currently outstanding.
Wintrust and IllinoisCommon Stock Transfer Company, as rights agent. Each right will entitle its registered holder to purchase from
Wintrust one one-hundredth of a share of Junior Serial PreferredCommon Stock A, without par value, at a price of $85.00 per one one-hundredth share, subject to certain adjustments. Generally, the rights become exercisable when any person or group (i) acquires or obtains the right to acquire 15% or more of Wintrust's common stock, or (ii) commences (or announces its intention to commence) a tender or exchange offer to acquire 15% or more of Wintrust's common stock. In the event that any person or group becomes the beneficial owner of 15% or more of Wintrust's common stock, rights owned by that person or group will immediately become null and void. Thereafter, other registered rights holders will have the right to receive, upon exercise at the then-current exercise price of the right, Wintrust common stock having a value equal to two times the exercise price of the right. Additionally, if, after any person or group has acquired 15% or more Wintrust's common stock, Wintrust is acquired in a merger or other business combination or 50% or more of Wintrust's assets or earning power are sold, then each registered right holder will receive the right to purchase, for the exercise price, common stock of the entity which acquires or survives Wintrust having a value equal to twice the exercise price of the right. Prior to any person or group acquiring 15% or more of Wintrust's common stock, Wintrust may redeem the rights in whole, but not in part, at a price of $0.01 per right, to be paid in cash,Outstanding. The outstanding shares of Wintrust common stock or other consideration. In addition, at any time after a person or group acquires 15%are, and the shares of Wintrust'sWintrust common stock but priorissued pursuant to such person or group acquiring 50% or morethe merger will be, duly authorized, validly issued, fully paid and non-assessable. The rights, preferences and privileges of Wintrust'sholders of Wintrust common stock are subject to, and may be adversely affected by, the rights of the holders of shares of any series of Wintrust preferred stock which Wintrust may exchangedesignate and issue in the rights, in whole or in part, at an exchange ratiofuture. Shares of one share ofWintrust common stock per right. The rights will expiremay be certificated or uncertificated, as provided by the IBCA.
Voting Rights. Each holder of Wintrust common stock is entitled to one vote for each share held on July 31, 2008 unless exercised, redeemed, exchanged or otherwise cancelled before that date. Town Banksharesall matters submitted to a vote of shareholders of Wintrust and does not have cumulative voting rights. Accordingly, holders of a majority of the shares of Wintrust common stock entitled to vote in any election of directors of Wintrust may elect all of the directors standing for election.
Dividend Rights. The holders of Wintrust common stock are entitled to receive dividends, if and when declared payable by the Wintrust board of directors from any funds legally available for the payment of dividends, subject to any preferential dividend rights of outstanding Wintrust preferred stock. Upon the liquidation, dissolution or winding up of Wintrust, the holders of Wintrust common stock are entitled to share pro rata in the net assets of Wintrust available after the payment of all debts and other liabilities and subject to the prior rights of any outstanding Wintrust preferred stock.
Preemptive Rights. Under its restated articles of incorporation, the holders of Wintrust common stock have no preemptive, subscription, redemption or conversion rights.
Wintrust Preferred Stock
Wintrust Preferred Stock Outstanding. As of the date of this proxy statement/prospectus, no shares of Wintrust preferred stock were issued and outstanding.
Blank Check Preferred Stock. Under its amended and restated articles of incorporation, the Wintrust board of directors has the authority to issue preferred stock in one or more classes or series, and to fix for each class or series the voting powers and the distinctive designations, preferences and relative, participation, optional or other special rights and such qualifications, limitations or restrictions, as may be stated and expressed in the resolution or resolutions adopted by the Wintrust board of directors providing for the issuance of such class or series as may be permitted by the IBCA, including dividend rates, conversion rights, terms of redemption and liquidation preferences and the number of shares constituting each such class or series, without any further vote or action by the shareholders rights plan. of Wintrust.
Exchange Agent and Registrar
     Illinois Stock Transfer Company is the exchange agent and registrar for the Wintrust common stock.
LEGAL MATTERS
     Certain matters pertaining to the validity of the authorization and issuance of the Wintrust common stock to be issued in the proposed merger will behave been passed upon by Vedder, Price, Kaufman & Kammholz, P.C., 222 North LaSalleSidley Austin LLP, One South Dearborn Street, Chicago, Illinois 60601.60603.
     Certain matters pertaining to the federal income tax consequences of the proposed merger will behave been passed upon by Reinhart Boerner Van Deuren s.c., 1000 North Water Street,Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP, 333 West Wacker Drive, Suite 2100, Milwaukee, Wisconsin 53202. Certain shareholders of Reinhart Boerner Van Deuren s.c. hold shares of Town Bankshares common stock. 53 2700, Chicago, Illinois 60606.

60


EXPERTS
     The consolidated financial statements of Wintrust as of December 31, 20032005 and 2002,2004, and for each of the three years in the period ended December 31, 2003,2005, included in Wintrust'sWintrust’s Annual Report on Form 10-K for the year ended December 31, 2003,2005, have been audited by Ernst & Young LLP, an independent registered public accounting firm, as set forth in their report thereon included in Wintrust'sWintrust’s Annual Report on Form 10-K for the year ended December 31, 2003,2005, and are incorporated by reference herein in reliance upon such report given on the authority of Ernst & Young LLP as experts in accounting and auditing.
SHAREHOLDER PROPOSALS
     After the merger is completed, the next annual meeting of Wintrust'sWintrust’s shareholders will be held in 2005.2007. To be considered for inclusion in Wintrust'sWintrust’s proxy materials for that annual meeting, any shareholder proposal must behave been received in writing at Wintrust'sWintrust’s principal office at 727 North Bank Lane, Lake Forest, Illinois 60045, no later thanby December 24, 2004.26, 2006. All shareholder proposals submitted for inclusion in Wintrust'sWintrust’s proxy materials will be subject to the requirements of the proxy rules adopted under the Securities Exchange Act, and, as with any shareholder proposal, Wintrust'sWintrust’s articles of incorporation and by-laws and Illinois law.
     Furthermore, in order for any shareholder to properly propose any business for consideration at Wintrust's 2005Wintrust’s 2007 annual meeting, including the nomination of any person for election as a director, or any other matter raised other than pursuant to Rule 14a-8 of the proxy rules adopted under the Securities Exchange Act, written notice of the shareholder'sshareholder’s intention to make such proposal must be furnished to Wintrust in accordance with its by-laws. Under the existing provisions of Wintrust'sWintrust’s by-laws, if the 20052006 annual meeting is held on May 26, 2005,24, 2006, the deadline for such notice is March 27, 2005. 25, 2007.
WHERE YOU CAN FIND MORE INFORMATION
     Wintrust files annual, quarterly and current reports, proxy statements and other information with the SEC. These filings are available to the public over the Internet at the SEC'sSEC’s website at www.sec.gov. You may also read and copy any document Wintrust files with the SEC at itsthe SEC’s public reference room located at 450 Fifth100 F Street, N.W.N.E., Washington D.C. 20549. Copies of these documents also can be obtained at prescribed rates by writing to the Public Reference Section of the SEC, at 450 Fifth100 F Street, N.W.N.E., Washington D.C. 20549 or by calling 1-800-SEC-0330 for additional information on the operation of the public reference facilities. Wintrust'sWintrust’s SEC filings are also available on its Web site at http://www.wintrust.com, and at the office of the Nasdaq National Market. For further information on obtaining copies of Wintrust'sWintrust’s public filings at the Nasdaq National Market, you should call (212) 656-5060.
     Wintrust filed with the SEC a registration statement on Form S-4 under the Securities Act to register the shares of Wintrust common stock to be issued to Town BanksharesHinsbrook’s shareholders inupon completion of the merger. This proxy statement/prospectus is a part of that registration statement and constitutes a prospectus of Wintrust in addition to being a proxy statement of Town BanksharesHinsbrook for its special meeting. As permitted by the SEC rules, this proxy statement/prospectus does not contain all of the information that you can find in the registration statement or in the exhibits to the registration statement. The additional information may be inspected and copied as set forth above.
INCORPORATION OF CERTAIN INFORMATION BY REFERENCE
     The SEC allows Wintrust to incorporate by reference information into this proxy statement/prospectus. This means that Wintrust can disclose important information to you by referring you to another document filed separately with the SEC. The information incorporated by reference is an important part of this proxy statement/prospectus, except for any information superseded by information in this proxy statement/prospectus. This proxy statement/prospectus incorporates by reference the documents set forth below that Wintrust has filed previously with the SEC: o Wintrust's
Wintrust’s Annual Report on Form 10-K for the year ended December 31, 20032005 (File No. 0-21923); 54 o Wintrust's proxy statement in connection with its 2004 annual meeting of shareholders filed with the SEC on April 23, 2004; o Wintrust's Quarterly Report on Form 10-Q for the three months ended March 31, 2004 (File No. 0-21923); o Wintrust's Quarterly Report on Form 10-Q for the three months ended June 30, 2004 (File No. 0-21923); o Wintrust's Current Report on Form 8-K filed with the SEC on January 21, 2004 (File No. 0-21923); o Wintrust's Current Report on Form 8-K filed with the SEC on April 20, 2004 (File No. 0-21923); o Wintrust's Current Report on Form 8-K filed with the SEC on May 11, 2004 (File No. 0-21923); o Wintrust's Current Report on Form 8-K filed with the SEC on June 14, 2004 (File No. 0-21923); o Wintrust's Current Report on Form 8-K filed with the SEC on July 20, 2004 (File No. 0-21923); and o the description of (a) Wintrust's common stock contained in Wintrust's Registration Statement on Form 8-A dated January 3, 1997 (File No. 0-21923), and (b) the associated preferred share purchase rights contained in Wintrust's Registration Statement on Form 8-A dated August 28, 1998

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Wintrust’s proxy statement in connection with its 2006 annual meeting of shareholders filed with the SEC on April 24, 2006;
Wintrust’s Current Reports on Form 8-K filed with the SEC on January 5, January 20, January 31, February 15, February 28, March 16, March 30 and April 21, 2006; and
the description of Wintrust’s common stock contained in Wintrust’s Registration Statement on Form 8-A dated January 3, 1997 filed pursuant to Section 12 of the Securities Exchange Act of 1934 (File No. 0-21923).
     Wintrust also incorporates by reference any additional filings it makes with the SEC pursuant to Sections 13(a), 13(c), 14 or 15(d) of the Securities Exchange Act after the date of this proxy statement/prospectus and before the special meeting. Any statement contained in a document incorporated by reference in this proxy statement/prospectus shall be deemed to be modified or superseded for purposes of this proxy statement/prospectus to the extent that a statement contained in this proxy statement/prospectus, or in any other document filed later which is also incorporated in this proxy statement/prospectus by reference, modifies or supersedes the statement. Any statement so modified or superseded shall not be deemed to constitute a part of this proxy statement/prospectus except as so modified or superseded. The information relating to Wintrust contained in this proxy statement/prospectus should be read together with the information in the documents incorporated in this proxy statement/prospectus by reference.
     You may request, either orally or in writing, and Wintrust will provide, a copy of these filings without charge by contacting David A. Dykstra, Wintrust'sWintrust’s Chief Operating Officer, at 727 North Bank Lane, Lake Forest, Illinois 60045, (847) 615-4096. IF YOU WOULD LIKE TO REQUEST DOCUMENTS, PLEASE DO SO BY _____________ ___, 2004, TO RECEIVE THEM BEFORE THE SPECIAL MEETING.If you would like to request documents, please do so by May 12, 2006, to receive them before the special meeting.
     All information concerning Wintrust and its subsidiaries has been furnished by Wintrust, and all information concerning Town BanksharesHinsbrook and Hinsbrook Bank & Trust has been furnished by Town Bankshares. 55 ANNEXHinsbrook.
You should rely only on the information contained or incorporated by reference in this proxy statement/prospectus to vote on the proposals to Hinsbrook shareholders in connection with the merger. We have not authorized anyone to provide you with information that is different from what is contained in this proxy statement/prospectus. This proxy statement/prospectus is dated ___, 2006. You should not assume that the information contained in this proxy statement/prospectus is accurate as of any date other than such date, and neither the mailing of this proxy statement/prospectus to shareholders nor the issuance of shares of Wintrust common stock as contemplated by the merger agreement will create any implication to the contrary.

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Annex A
AGREEMENT AND PLAN OF MERGER
BY AND BETWEEN
WINTRUST FINANCIAL CORPORATION
AND TOWN BANKSHARES, LTD. DATED AS OF JUNE 14, 2004
HINSBROOK BANCSHARES, INC.
Dated December 5, 2005


TABLE OF CONTENTS
PAGE Article 1
ARTICLE I THE MERGER...................................................................................A-1 MERGERA-1
1.1The Merger...................................................................................A-1 MergerA-1
1.2Effective Time...............................................................................A-1 TimeA-1
1.3Effect of the Merger.........................................................................A-1 MergerA-1
1.4 Merger Consideration.........................................................................A-1 Conversion of SharesA-1
1.5 Effect on Capital Shares; Dissenting Shares..................................................A-2 1.6 Company Stock Options........................................................................A-2 1.7 OptionsA-2
1.6Cancellation of Treasury Shares..............................................................A-3 SharesA-2
1.7Dissenting SharesA-2
1.8 Recapitalization.............................................................................A-3 RecapitalizationA-3
1.9Tax Treatment................................................................................A-3 TreatmentA-3
1.10 Closing......................................................................................A-3 Article 2ClosingA-3
ARTICLE II CONVERSION AND EXCHANGE OF CERTIFICATES.....................................................................A-3 CERTIFICATES IN MERGERA-3
2.1 Wintrust to Make SharesPer Share Merger ConsiderationA-3
2.2Election ProceduresA-4
2.3Proration and Cash Available...................................................A-3 2.2 Redesignation ProceduresA-4
2.4No Fractional Shares.........................................................................A-4 2.3 SharesA-5
2.5Exchange of Certificates.....................................................................A-4 Article 3CertificatesA-5
ARTICLE III REPRESENTATIONS AND WARRANTIES CONCERNING THE COMPANY........................................A-5 COMPANYA-7
3.1 Organization.................................................................................A-5 OrganizationA-7
3.2Organizational Documents; Minutes and Stock Records..........................................A-6 RecordsA-7
3.3 Capitalization...............................................................................A-6 CapitalizationA-8
3.4Authorization; No Violation..................................................................A-7 ViolationA-8
3.5Consents and Approvals.......................................................................A-7 ApprovalsA-8
3.6Financial Statements.........................................................................A-7 StatementsA-9
3.7No Undisclosed Liabilities...................................................................A-8 LiabilitiesA-9
3.8Loans; Allowance for Loan Losses.............................................................A-8 Loss ReservesA-10
3.9Properties and Assets........................................................................A-8 AssetsA-10
3.10Material Contracts...........................................................................A-9 ContractsA-11
3.11No Defaults.................................................................................A-10 DefaultsA-12
3.12Conflict of Interest Transactions...........................................................A-10 TransactionsA-12
3.13 Investments.................................................................................A-10 InvestmentsA-12
3.14Compliance with Laws; Legal Proceedings.....................................................A-11 ProceedingsA-13
3.15 Insurance...................................................................................A-11 InsuranceA-13
3.16 Taxes.......................................................................................A-12 TaxesA-13
3.17Environmental Laws and Regulations..........................................................A-12 RegulationsA-14
3.18Community Reinvestment Act Compliance.......................................................A-13 ComplianceA-15
3.19Company Regulatory Reports..................................................................A-13 ReportsA-15
3.20Employee Benefit Plans......................................................................A-13 PlansA-15
3.21Technology and Intellectual Property........................................................A-15 PropertyA-17
3.22No Adverse Change...........................................................................A-15 ChangeA-18
3.23Conduct of Business in Ordinary Course......................................................A-16 Normal CourseA-18
3.24Change in Business Relationships............................................................A-16 RelationshipsA-18
3.25 Brokers'Brokers’ and Finders' Fees..................................................................A-16 Finders’ FeesA-18

A-i


3.26 No Omissions................................................................................A-16 3.27 Section 280G Payments.......................................................................A-16 Article 4PaymentsA-18
3.27No OmissionsA-18
ARTICLE IV REPRESENTATIONS AND WARRANTIES CONCERNING WINTRUST..........................................A-16 WINTRUSTA-18
4.1 Organization................................................................................A-16 OrganizationA-18
4.2 Capitalization..............................................................................A-16 CapitalizationA-18
4.3Authorization; No Violations................................................................A-17 ViolationsA-19
4.4Consents and Approvals......................................................................A-17 ApprovalsA-19
4.5Wintrust SEC DocumentsFilings and Financial Statements.............................................A-17
A-i TABLE OF CONTENTS (continued)
PAGE Statements
A-19
4.6Compliance with Laws; Legal Proceedings.....................................................A-17 ProceedingsA-20
4.7Wintrust Regulatory Reports.................................................................A-18 ReportsA-20
4.8No Adverse Change...........................................................................A-18 ChangeA-20
4.9 Brokers'Brokers’ and Finders' Fees..................................................................A-18 Finders’ FeesA-21
4.10Taxation of the Merger......................................................................A-18 MergerA-21
4.11Financial AbilityA-21
4.12No Omissions................................................................................A-18 Article 5OmissionsA-21
ARTICLE V AGREEMENTS AND COVENANTS....................................................................A-19 COVENANTSA-21
5.1Conduct of Business.........................................................................A-19 BusinessA-21
5.2Access to Information.......................................................................A-20 InformationA-22
5.3Meeting of Shareholders of the Company......................................................A-20 CompanyA-23
5.4Registration Statement and Regulatory Filings...............................................A-21 FilingsA-23
5.5Listing of Shares...........................................................................A-21 SharesA-24
5.6Reasonable and Diligent Efforts.............................................................A-21 EffortsA-24
5.7Business Relations and Publicity............................................................A-21 PublicityA-24
5.8No Conduct Inconsistent with this Agreement.................................................A-22 AgreementA-24
5.9Loan Charge-Off; Pre-Closing Loan Review.....................................................................A-22 ReviewA-25
5.10Board of Directors'Directors’ Notices and Minutes.....................................................A-23 MinutesA-25
5.11Untrue Representations and Warranties.......................................................A-23 WarrantiesA-26
5.12Director and Officer Indemnification and Liability Coverage.................................A-23 CoverageA-26
5.13 MonthlyInterim Financial Statements................................................................A-24 StatementsA-26
5.14Dissent Process.............................................................................A-24 ProcessA-26
5.15Section 368(a) Reorganization...............................................................A-24 ReorganizationA-26
5.16 TreatmentExercise of Options........................................................................A-24 OptionsA-26
5.17Converted Options...........................................................................A-25 Article 6OptionsA-26
5.18Termination of Ownership InterestsA-27
ARTICLE VI EMPLOYEE BENEFIT MATTERS....................................................................A-25 MATTERSA-27
6.1Benefit Plans...............................................................................A-25 PlansA-27
6.2 Termination of ESOP; Redemption of ESOP Shares..............................................A-25 6.3 No Rights or Remedies.......................................................................A-26 Article 7RemediesA-27
ARTICLE VII CONDITIONS PRECEDENT TO OBLIGATIONS OF WINTRUST.............................................A-26 WINTRUSTA-28
7.1Representations and Warranties; Performance of Agreements...................................A-26 AgreementsA-28
7.2Closing Certificate.........................................................................A-26 CertificateA-28
7.3Regulatory and Other Approvals..............................................................A-26 ApprovalsA-28
7.4Approval of Merger and Delivery of Agreement................................................A-26 AgreementA-28
7.5Effectiveness of the Registration Statement.................................................A-27 StatementA-28

A-ii


7.6No Litigation...............................................................................A-27 LitigationA-28
7.7 Termination of ESOP.........................................................................A-27 Environmental SurveysA-28
7.8Opinion of Counsel..........................................................................A-27 CounselA-29
7.9Employment Agreements.......................................................................A-27 AgreementsA-29
7.10No Adverse Changes..........................................................................A-27 ChangesA-29
7.11Minimum Net Worth and Loan Loss Reserve Requirements........................................A-27 RequirementsA-29
7.12 Consents....................................................................................A-27 Voting AgreementsA-29
7.13Amendments to Deferred Compensation Agreement...............................................A-28 AgreementsA-29
7.14SettlementA-30
7.15ConsentsA-30
7.16Other Documents.............................................................................A-28 Article 8DocumentsA-30
ARTICLE VIII CONDITIONS PRECEDENT TO OBLIGATIONS OF THE COMPANY..........................................A-28 COMPANYA-30
8.1Representations and Warranties; Performance of Agreements...................................A-28 AgreementsA-30
8.2Closing Certificates........................................................................A-28 CertificatesA-30
8.3Regulatory and Other Approvals..............................................................A-28 ApprovalsA-30
8.4 Approval of Merger and Delivery of Agreement................................................A-28 AgreementA-30
8.5Effectiveness of the Registration Statement.................................................A-28
A-ii TABLE OF CONTENTS (continued)
PAGE Statement
A-30
8.6No Litigation...............................................................................A-28 LitigationA-30
8.7Opinions of Counsel.........................................................................A-29 CounselA-31
8.8No Adverse Changes..........................................................................A-29 ChangesA-31
8.9Nasdaq Listing..............................................................................A-29 ListingA-31
8.10Other Documents.............................................................................A-29 Article 9DocumentsA-31
ARTICLE IX NON-SURVIVAL OF REPRESENTATIONS, WARRANTIES AND COVENANTS...................................A-29 COVENANTSA-31
9.1 Non-Survival................................................................................A-29 Article 10 GENERAL.....................................................................................A-29 Non-SurvivalA-31
ARTICLE X GENERALA-31
10.1 Expenses....................................................................................A-29 ExpensesA-31
10.2 Termination.................................................................................A-30 TerminationA-33
10.3Confidential Information....................................................................A-31 InformationA-34
10.4 Non-Assignment; Third-Party Beneficiaries...................................................A-31 Non-AssignmentA-34
10.5 Notices.....................................................................................A-31 NoticesA-34
10.6 Counterparts................................................................................A-32 CounterpartsA-34
10.7 Knowledge...................................................................................A-32 KnowledgeA-34
10.8InterpretationA-35
10.9Entire Agreement............................................................................A-32 10.9 AgreementA-35
10.10Governing Law...............................................................................A-32 10.10 Severability................................................................................A-32 LawA-35
10.11SeverabilityA-35

A-iii


DEFINED TERMS
Acquisition Proposal...........................................................................................A-22 Agreement.......................................................................................................A-1 ProposalA-24
AgreementA-1
Articles of Merger..............................................................................................A-1 Bank............................................................................................................A-1 MergerA-1
BankA-1
Benefit Plans..................................................................................................A-13 BHCA............................................................................................................A-5 CERCLA.........................................................................................................A-13 Closing.........................................................................................................A-3 PlansA-15
BHCAA-7
Cash ConsiderationA-3
Cash ElectionA-4
Cash Election SharesA-4
CERCLAA-15
ClosingA-3
Closing Date....................................................................................................A-3 Code............................................................................................................A-1 Commission......................................................................................................A-7 Company.........................................................................................................A-1 Balance SheetA-29
Closing DateA-3
CodeA-1
Combination ElectionA-4
CommissionA-9
CompanyA-1
Company Board...................................................................................................A-7 BoardA-8
Company Common Share............................................................................................A-1 Company Common Shares...........................................................................................A-1 Company Material Impact........................................................................................A-26 StockA-1
Company Option Plan.............................................................................................A-2 PlanA-2
Company Regulatory Reports.....................................................................................A-13 ReportsA-15
Company Share Certificates......................................................................................A-3 Stock CertificatesA-5
Confidentiality Agreement......................................................................................A-20 AgreementA-23
Conversion Fund.................................................................................................A-3 FundA-6
Converted Option................................................................................................A-2 CRA............................................................................................................A-13 Deferred Compensation Agreements...............................................................................A-28 OptionA-2
CRAA-15
Dissenting Shares...............................................................................................A-2 SharesA-2
Effective Time..................................................................................................A-1 Employees......................................................................................................A-25 Encumbrances....................................................................................................A-8 TimeA-1
Election DeadlineA-4
Election FormA-4
EmployeesA-27
EncumbrancesA-10
Environmental Laws.............................................................................................A-12 LawsA-14
ERISA Affiliate................................................................................................A-14 AffiliateA-15
ERISA Plans....................................................................................................A-13 ESOP...........................................................................................................A-25 ESOP Participants..............................................................................................A-25 ESOP Share Redemption..........................................................................................A-25 ESOP Share Redemption Price....................................................................................A-25 ESOP Shares....................................................................................................A-25 PlansA-15
Exchange Act...................................................................................................A-17 ActA-19
Exchange Agent..................................................................................................A-3 FDIC...........................................................................................................A-13 AgentA-4
FDICA-10
Federal Reserve.................................................................................................A-7 ReserveA-9
Federal Reserve Application.....................................................................................A-7 Final Determination Letter.....................................................................................A-25 ApplicationA-9
Financial Statements............................................................................................A-7 GAAP............................................................................................................A-5 StatementsA-9
GAAPA-7
Governmental Authority..........................................................................................A-7 AuthorityA-8
Hazardous Substance............................................................................................A-13 SubstanceA-15
IDFPRA-9

A-iv


IDFPR ApplicationA-9
Illinois Act....................................................................................................A-1 ActA-1
Intellectual Property..........................................................................................A-15 PropertyA-17
Interim Balance Sheet...........................................................................................A-7 SheetA-9
Interim Financial Statements....................................................................................A-7 StatementsA-9
Investment Securities..........................................................................................A-10 IRS............................................................................................................A-14 SecuritiesA-12
IRSA-16
IT Assets......................................................................................................A-15
A-iv
knowledge......................................................................................................A-32 Loans...........................................................................................................A-8 Assets
A-17
knowledgeA-34
LicensesA-13
LoansA-10
Material Adverse Effect.........................................................................................A-5 EffectA-7
Material Contracts..............................................................................................A-9 ContractsA-11
Maximum Amount.................................................................................................A-24 Merger..........................................................................................................A-1 Cash Election NumberA-4
Maximum Stock Election NumberA-4
MergerA-1
Minimum Adjusted Net WorthA-29
OCCA-20
Option Conversion Agreement.....................................................................................A-3 Option Exchange Ratio...........................................................................................A-2 AgreementA-2
OptionsA-8
Ordinary Course of Business.....................................................................................A-8 BusinessA-9
OREO
Outstanding Company Option......................................................................................A-2 Parties.........................................................................................................A-1 Per Share Cash Consideration....................................................................................A-2 OptionA-2
PartiesA-1
Per Share Merger Consideration..................................................................................A-1ConsiderationA-3
Permitted EncumbrancesA-10
Plan AmendmentsA-2
Price Per Share Stock Consideration...................................................................................A-1 Permitted Encumbrances..........................................................................................A-9 Plan Amendment..................................................................................................A-3 A-3
Proxy Statement/Prospectus......................................................................................A-7 ProspectusA-9
Registration Statement.........................................................................................A-21 StatementA-23
RepresentativesA-4
Retained Plans.................................................................................................A-25 Returns........................................................................................................A-12 PlansA-27
Securities Act..................................................................................................A-7 ActA-9
Shareholders Meeting...........................................................................................A-20 Subsidiaries....................................................................................................A-5 MeetingA-23
Stock ConsiderationA-3
Stock ElectionA-4
Stock Election SharesA-5
Superior Acquisition Proposal..................................................................................A-22 ProposalA-25
Surviving Corporation...........................................................................................A-1 TIC.............................................................................................................A-5 Trust...........................................................................................................A-5 WDFI............................................................................................................A-1 WDFI Application................................................................................................A-7 Wintrust........................................................................................................A-1 CorporationA-1
Tax ReturnA-14
TaxesA-14
Wintrust Common Stock...........................................................................................A-1 A-1
Wintrust Common Stock Price.....................................................................................A-2 Wintrust Material Impact.......................................................................................A-28 PriceA-3
Wintrust Regulatory Reports....................................................................................A-18 ReportsA-20
Wintrust SEC Documents.........................................................................................A-17 DocumentsA-19
Wintrust Stock Certificates.....................................................................................A-3 Wisconsin Act...................................................................................................A-1 CertificatesA-5

A-v


DISCLOSURE SCHEDULES
DISCLOSURE SCHEDULES Equity Investments
Ownership Interests3.1(b)
Schedule of Option Holders3.3(a)
Stock Owned by the Company...........................................................................3.1(b) Equity Investments of the Bank..............................................................................3.3(b) Bank3.3(b)
Authorization; No Violation.................................................................................3.4Violation3.4
Required Consents and Approvals......................................................................................3.5 3.5
Financial Statements........................................................................................3.6 No Undisclosed Liabilities..................................................................................3.7 Loans; Allowance for Loan Losses............................................................................3.8Statements3.6
Schedule of Real Property...............................................................................................3.9(a)Property3.9(a)
Schedule of Tangible Personal Property...........................................................................................3.9(b) Assets......................................................................................................3.9(c)Property3.9(b)
Schedule of Material Contracts..........................................................................................3.10 ConflictContracts3.10
Schedule of Interest........................................................................................3.12 Investments.................................................................................................3.13(a) Compliance with Laws; Interested Transactions3.12
Schedule of Investments3.13(a)
Schedule of Restricted Investment Securities3.13(b)
Schedule of Disposed Investment Securities3.13(c)
Legal Proceedings.....................................................................3.14 Insurance...................................................................................................3.15 Taxes.......................................................................................................3.16 Proceedings3.14(c)
Schedule of Insurance3.15
Taxes3.16
Environmental Laws and Regulations..........................................................................3.17 EmployeeMatters3.17
Change of Control Provisions Under Benefit Plans......................................................................................3.20 Technology andPlans3.20(b)
Medical Benefits3.20(c)
Exceptions Under Benefit Plans3.20(e)
Schedule of Intellectual Property........................................................................3.21 Brokers' and Finders' Fees..................................................................................3.25 Property3.21
Conduct of Business.........................................................................................5.1 List of Employees...........................................................................................6.1 EXHIBITS Exhibit A.........Form ofBusiness in Normal Course; Exceptions3.23
Brokers’ and Finders’ Fees3.25
280G Payments3.26
Scheduled Compensation Changes5.1(c)
Employees6.1
Employment Agreements7.9
Signatories to Voting Agreement7.12
Deferred Compensation Agreements7.13
Settlement7.14
EXHIBITS
Exhibit B.........FormAForm of Option Conversion Agreement
Exhibit C.........FormBForm of Opinion of Company Counsel
Exhibit D.........FormsCForm of Key Management Employment Agreement
Exhibit E.........FormDForm of Voting Agreement
Exhibit EForms of Amendment to Deferred Compensation Agreements
Exhibit FForm of Opinion of Wintrust Counsel

A-vi


AGREEMENT AND PLAN OF MERGER
      This AGREEMENT AND PLAN OF MERGER (this "Agreement"Agreement), is entered into as of the 14th5th day of June, 2004,December, 2005, by and between WINTRUST FINANCIAL CORPORATION, an Illinois corporation ("Wintrust"(“Wintrust), and TOWN BANKSHARES, LTD.HINSBROOK BANCSHARES, INC., a Wisconsinan Illinois corporation (the "Company"Company). Wintrust and the Company are together referred to collectively in this Agreement as the "Parties." Parties.
RECITALS
      WHEREAS, the boards of directors of each of the Parties have approved and declared it advisable and in the best interest of the Parties and their respective shareholders to effect a reorganization, whereby the Company will merge with and into Wintrust, in the manner and on the terms and subject to the conditions set forth in Article I below (the "Merger"Merger), as a result of which the Company will merge out of existence and TownHinsbrook Bank a Wisconsin& Trust, an Illinois state bank and wholly owned subsidiary of the Company (the "Bank"Bank), will become a wholly owned subsidiary of Wintrust. WHEREAS, as a condition to the willingness of Wintrust to enter into this Agreement, certain shareholders of the Company are simultaneously herewith entering into a Voting Agreement, in the form attached hereto as Exhibit A.
      WHEREAS, for federal income tax purposes the Parties desire and intend that the Merger qualify as a reorganization in accordance with Section 368(a) of the Internal Revenue Code of 1986, as amended (the "Code"Code).
      NOW THEREFORE, in consideration of the premises and the mutual promises herein made, and in consideration of the representations, warranties and covenants herein contained, the Parties hereby agree as follows. follows:
ARTICLE 1 I
THE MERGER
      1.1     The Merger. At the Effective Time, as defined in Section 1.2, in accordance with this Agreement and the Illinois Business Corporation Act (the "Illinois Act") and the Wisconsin Business Corporation Law (the "Wisconsin Act"Illinois Act), the Company shall be merged with and into Wintrust, and Wintrust shall continue as the corporation surviving the Merger (sometimes referred to herein as the "Surviving Corporation"Surviving Corporation).
      1.2     Effective Time. As of the Closing, as defined in Section 1.10, with respect to the Merger the Parties will cause articles of merger (the "ArticlesArticles of Merger"Merger) with respect to the Merger to be executed and filed with the Illinois Secretary of State of the State of Illinois as provided in the Illinois Act and with the Department of Financial Institutions of the State of Wisconsin (the "WDFI") as provided in the Wisconsin Act. The Merger shall become effective on the date and time aton which the Articles of Merger are duly filed by the Secretary of State of the State of Illinois, and the WDFI, or at such othertime on such filing date and time as is agreed among the Parties and specified in the Articles of Merger (the "Effective Time"Effective Time).
      1.3     Effect of the Merger. At and after the Effective Time, the Merger shall have the effecteffects set forth in Section 11.50 of the Illinois Act and Section 180.1106Act.
      1.4     Conversion of the Wisconsin Act. 1.4 Merger Consideration.Shares. At the Effective Time, by virtue of the Merger and without any action on the part of the Parties or the shareholders of the Company, each share of common sharestock of the Company, par value $0.01$0.05 per share (each, a "Company(“Company Common Share" and collectively, "Company Common Shares"Stock), issued and outstanding immediately prior to the Effective Time (other than (i)shares of Company Common SharesStock to be cancelledcanceled pursuant to Section 1.7, (ii)1.6 and Dissenting Shares and (iii) any ESOP Shares)to the extent provided in Section 1.7), shall by reason of the Merger and without any action by the holder thereof, be converted into the right to receive shares of common stock, no par value, of Wintrust ("Wintrust Common Stock") and cash having an aggregate value of $129.10 (the "Per Share Merger Consideration"), determined as follows: (a) Per Share Stock Consideration. The number of shares of Wintrust Common Stock issuable upon conversion of each Company Common Share (the "Per Share Stock Consideration") shall be determined as follows: A-1 (i) If the unweighted average of the high and low sale prices of a share of Wintrust Common Stock as reported on the Nasdaq National Market for each of the ten trading days ending on the second trading day preceding the Closing Date (as defined in Section 1.10) (the "Wintrust Common Stock Price") is at least $41.34 and no more than $55.34 the Per Share Stock Consideration shall be the number of shares, rounded to the nearest thousandth of a share, equal to the quotient obtained by dividing $71.00 by the Wintrust Common Stock Price. (ii) If the Wintrust Common Stock Price is less than $41.34, the Per Share Stock Consideration shall be the number of shares, rounded to the nearest thousandth of a share, equal to the quotient obtained by dividing $71.00 by 41.34. (iii) If the Wintrust Common Stock Price is greater than $55.34, the Per Share Stock Consideration shall be the number of shares, rounded to the nearest thousandth of a share, equal to the quotient obtained by dividing $71.00 by $55.34. (b) Per Share Cash Consideration. The amount of cash payable upon conversion of each Company Common Share (the "Per Share Cash Consideration") shall be equal to $58.10. 1.5 Effect on Capital Shares; Dissenting Shares. (a) Each Company Common Share converted into the right to receive the Per Share Merger Consideration, as defined in accordance with thisand pursuant to Article III. At the Effective Time, each share of Company Common Stock shall no longer be outstanding and shall automatically be cancelledcanceled and retired and shall cease to exist, as of the Effective Time, and each certificate previously representingevidencing any such share (other than shares canceled pursuant to Section 1.6 and Dissenting Shares) shall thereafter represent only the right to receive, upon surrender of such certificate in accordance with Section 2.5, the Per Share Merger Consideration, payable in the manner provided in Article II, and cash in lieu of any fractional shares of Wintrust Common Stock issuable in connection therewith. The holders of such certificates previously evidencing such shares of Company Common SharesStock outstanding immediately prior to the Effective Time shall cease to have any rights with respect thereto except as otherwise provided in this Agreement or by law.

A-1


      1.5     Company Stock Options.
      (a) At the Effective Time, each option granted by the Company under the terms of the Hinsbrook Bancshares, Inc. 1992 Stock Option Plan (the “Company Option Plan”) to purchase shares of Company Common Stock that is outstanding and unexercised immediately prior to the Effective Time (an “Outstanding Company Option”) shall cease to represent a right to receiveacquire shares of Company Common Stock and shall be converted automatically into an option to purchase shares of Wintrust Common Stock in an amount and at an exercise price determined pursuant to this Section 1.5 (a “Converted Option”), subject to the terms, benefits, rights and features of the Company Option Plan and the agreements evidencing grants of such options thereunder as in existence immediately prior to the Effective Time, which shall continue to apply to each Converted Option from and after the Effective Time.
      (b) The number of shares of Wintrust Common Stock to be subject to each Converted Option shall be equal to the product obtained by multiplying (i) the number of shares of Company Common Stock under each Outstanding Company Option by (ii) the quotient of (a) the Price Per Share, as defined in Section 2.1(a)(i), divided by (b) the Wintrust Common Stock Price, as defined in Section 2.1(c),provided that any fractional shares of Wintrust Common Stock resulting from such determination shall be rounded down to the nearest whole share.
      (c) The exercise price per share of Wintrust Common Stock under each Converted Option shall be equal to (i) the exercise price per share of Company Common Stock under the original option divided by (ii) the quotient of (a) the Price Per Share divided by (b) the Wintrust Common Stock Price,provided that such exercise price shall be rounded down to the nearest whole cent.
      (d) The adjustments provided herein with respect to any Outstanding Company Options that are “incentive stock options” as defined in Section 422 of the Code shall be effected in a manner consistent with the requirements of Section 424(a) of the Code.
      (e) The Company Option Plan shall be amended, effective as of the Effective Time, to provide for the conversion of Outstanding Company Options in accordance with this Section 2.3(a)1.5 (the “Plan Amendment”). The Company shall provide to Wintrust, not less than five (5) business days prior to the Closing Date, copies of an agreement in the form ofExhibit A attached hereto (the “Option Conversion Agreement”) from each of the holders of Outstanding Company Options acknowledging their agreement and consent to the Plan Amendment and to such terms of conversion set forth in this Section 1.5.
      1.6     Cancellation of Treasury Shares. At the Effective Time, each share of Company Common Stock held as treasury stock or otherwise held by the Company or the Bank (other than in a fiduciary capacity), if any, immediately prior to the Effective Time shall automatically be canceled and retired and cease to exist, and no Per Share StockMerger Consideration and cash in lieu of any fractional shares thereof determined pursuant to Section 2.2, and (ii) the Per Share Cash Consideration. (b)shall be exchanged therefor.
      1.7     Dissenting Shares. Any holder of Company Common Shares otherwise entitled to receive the Per Share Merger Consideration in exchange for each of his or her Company Common Shares shall be entitled to dissent from the corporate action being taken hereby and demand payment in cash of the fair value for his or her Company Common Shares as specified in Sections 180.1301 to 180.133111.65 and 11.70 of the WisconsinIllinois Act if the holder followsfully complies with the proceduresrequirements specified therein (such shares hereinafter referred to as "Dissenting Shares"Dissenting Shares). No holder of Dissenting Shares shall, after the Effective Time, be entitled to receive any shares of Wintrust Common Stock or the Per Shareany payment of Cash Consideration pursuant to this Agreement, or be entitled to vote for any purpose or receive any dividends or other distributions with respect to such Wintrust Common Stock;provided,however, that Company Common Shares held by a dissenting shareholder who subsequently withdraws a demand for payment, fails to comply with the requirements of the WisconsinIllinois Act, or otherwise fails to establish the right of such shareholder to receive payment in cash of the fair value forof such shareholder'sshareholder’s shares under the WisconsinIllinois Act shall be deemed to be converted into the right to receive the Per Share Merger Consideration pursuantin exchange for each such share, to the terms and conditions specified herein. 1.6 Company Stock Options. (a) At the Effective Time, each option granted by the Company under the termsbe payable as Cash Consideration, without interest thereon, upon surrender of the Town Bankshares, Ltd. 1997 Stock Incentive Plan, as amended (the "Company Option Plan") to purchase Company Commoncertificate or certificates that formerly evidenced such Dissenting Shares that is outstanding and unexercised immediately prior to the Effective Time (an "Outstanding Company Option"), shall be converted into an option to purchase shares of Wintrust Common Stock (a "Converted Option") in such number and at such exercise price as set forth herein and otherwise having the same terms and conditions as in effect immediately prior to the Effective Time except to the extent that such Outstanding Company Options shall be altered in accordance with their terms as a result of the Merger contemplated hereby, as follows: (i) the number of shares of Wintrust Common Stock to be subject to the Converted Option shall be equal to the product obtained by multiplying (1) the number of Company Common Shares subject to the original Outstanding Company Option by (2) the quotient obtained by dividing the Per Share Merger Consideration by the Wintrust Common Stock Price (such quotient, the "Option Exchange Ratio"); (ii) the exercise price per share of Wintrust Common Stock under the Converted Option shall be equal to the quotient obtained by dividing (1) the exercise price per Company Common Share under the original Outstanding Company Option by (2) the Option Exchange Ratio; and (iii) upon exercise of each Converted Option by a holder thereof, the aggregate number of shares of Wintrust A-2 Common Stock deliverable upon such exercise shall be rounded down, if necessary, to the nearest whole share and the aggregate exercise price shall be rounded up, if necessary, to the nearest cent. (b) The adjustments provided herein with respect to any Outstanding Company Options that are "incentive stock options" (as defined in Section 422 of the Code) shall be effected in a manner consistent with the requirements of Section 424(a) of the Code. (c) The Company Option Plan shall be amended, effective as of the Effective Time, to provide for the conversion of Outstanding Company Options in accordance with Section 1.6(a) (the "Plan Amendment"). The Company shall provide to Wintrust, not less than five (5) business days prior to the Closing Date, copies of an agreement in the form of Exhibit B attached hereto (the "Option Conversion Agreement") from each of the holders of Outstanding Company Options acknowledging their agreement and consent to the Plan Amendment and to such terms of conversionmanner set forth in this Section 1.6. 1.7 Cancellation of Treasury Shares. At the Effective Time, each Company Common Share held as treasury stock, if any, immediately prior to the Effective Time shall automatically be cancelled and retired and cease to exist, and no shares of Wintrust Common Stock or other consideration shall be exchanged therefor.2.5.

A-2


      1.8     Recapitalization. In the event that Wintrust changes (or establishes a record date for changing) the number of shares of Wintrust Common Stock issued and outstanding as a result of a stock dividend, stock split, recapitalization, reclassification, combination or similar transaction with respect to the outstanding shares of Wintrust Common Stock and the record date therefor shall be after the date of this Agreement and prior to the Effective Time, then the calculations of the Per Share Stock Considerationconversion provisions described in Section 1.4(a)Article II shall be appropriately and proportionately adjusted.
      1.9     Tax Treatment. It is intended that the Merger shall constitute a reorganization within the meaning of Section 368(a) of the Code, and that this Agreement shall constitute a "plan“plan of reorganization"reorganization” for purposes of Section 368 of the Code.
      1.10     Closing. The consummation of the transactions contemplated by this Agreement shall take place at a closing (the "Closing"Closing) to be held on the fifth business day following the date on which all of the conditions set forth in Sections 7.3Articles VII and 7.4VIII of this Agreement have been satisfied, or on such other date as Wintrust and the CompanyParties may mutually agree (the "Closing Date"Closing Date). In the event of the filing of any motion for rehearing or any appeal from the decision of any regulatory authority approving the transactions contemplated in this Agreement or any legal proceedings of the type contemplated by Sections 7.6 or 8.6, Wintrust or the Company may postpone the Closing by written notice to the other parties until such approvals have been obtained or such motion, appeal or litigation has been resolved, but in no event shall such Closing be postponed beyond the close of business on November 30, 2004July 31, 2006 (except as may be extended pursuant to Section 10.2(b)) without the consent of the boards of directors of Wintrust and the Company. The Closing shall take place at 10:00 a.m., local time, on the Closing Date at the offices of Schiff Hardin LLP, 6600 Sears Tower, Chicago, Illinois, or at such other place and time upon which the partiesParties may agree.
ARTICLE 2II
CONVERSION AND EXCHANGE OF CERTIFICATES IN MERGER
2.1     Wintrust to Make SharesPer Share Merger Consideration.
      (a) Each share of Company Common Stock issued and Cash Available. At oroutstanding immediately prior to the Effective Time (other than shares of Company Common Stock to be canceled pursuant to Section 1.6 and Dissenting Shares) shall be converted into the right to receive the appropriate elected or otherwise assigned Per Share Merger Consideration, subject to the provisions of this Article II. “Per Share Merger Consideration” shall mean one of the following:
      (i) cash in the amount of $41.59 (the “Price Per Share”), without interest (the “Cash Consideration”);
      (ii) that number of shares of Wintrust Common Stock, rounded to the nearest thousandth of a share, equal to the quotient obtained by dividing the Price Per Share by the Wintrust Common Stock Price (as determined in accordance with Section 2.1(b)) (the “Stock Consideration”); or
      (iii) a combination of Cash Consideration and Stock Consideration determined in accordance with Section 2.2(a).
      (b) “Wintrust Common Stock Price” means the unweighted average of the high and low sale prices of a share of Wintrust Common Stock as reported on the Nasdaq National Market for each of the ten (10) trading days ending on the fourth (4th) trading day preceding the Closing Date;provided,however, that if the Wintrust Common Stock Price as calculated above is less than $49.14, the Wintrust Common Stock Price for purposes of this Agreement shall be $49.14, and if the Wintrust Common Stock Price as calculated above is greater than $61.14, the Wintrust Common Stock for purposes of this Agreement shall be $61.14.
      (c) The number of shares of Company Common Stock to be converted into the right to receive Cash Consideration for such shares, consisting of (i) those shares subject to Cash Elections and (ii) those

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shares subject to the cash portion of Combination Elections, as such terms are defined below, shall be 50% of the number of shares of Company Common Stock outstanding immediately prior to the Effective Time (excluding shares to be canceled pursuant to Section 1.6 and Dissenting Shares) (the “Maximum Cash Election Number”). The number of shares of Company Common Stock to be converted into the right to receive Stock Consideration for such shares, consisting of (i) those shares subject to Stock Elections and (ii) those shares subject to the stock portion of Combination Elections, shall be 50% of the number of shares of Company Common Stock outstanding immediately prior to the Effective Time (excluding shares to be canceled pursuant to Section 1.6 and Dissenting Shares) (the “Maximum Stock Election Number”). Notwithstanding the foregoing, the percentages used in the preceding definitions are subject to waiver or modification pursuant to Section 2.3(d) or adjustment pursuant to Section 10.2(f).
      2.2     Election Procedures.
      (a) Subject to the proration and redesignation procedures set forth in Section 2.3 below, each holder of record of shares of Company Common Stock (excluding shares to be canceled pursuant to Section 1.6 and Dissenting Shares) will be entitled to elect to receive (i) Stock Consideration for all such shares (a “Stock Election”), (ii) Cash Consideration for all such shares (a “Cash Election”) or (iii) Cash Consideration for 50% of such shares and Stock Consideration for 50% of such shares (a “Combination Election”). All such elections shall be made on a form designed for that purpose prepared by the Company and acceptable to Wintrust (an “Election Form”). Holders of record of shares of Company Common Stock who hold such shares as nominees, trustees or in other representative capacities (“Representatives”) may submit multiple Election Forms,provided that such Representative certifies that each such Election Form covers all the shares of Company Common Stock held by each such Representative for a particular beneficial owner.
      (b) The Election Form shall be mailed with the Proxy Statement/ Prospectus to all holders of record of shares of Company Common Stock as of the record date of the Shareholders Meeting. Thereafter the Company and Wintrust shall authorize the issuance ofeach use its reasonable and shalldiligent efforts to mail or make available the Election Form to all persons who become holders of shares of Company Common Stock during the period between the record date for the Shareholders Meeting and 5:00 pm., Chicago Time, on the date ten (10) business days prior to the anticipated Effective Time.In order to be effective an Election Form must be received by Illinois Stock Transfer Company, Wintrust’s exchange agent (the "Exchange Agent"Exchange Agent), foron or before 5:00 p.m., Chicago Time, on the benefitfifth (5th) business day prior to the Effective Time (the “Election Deadline”). An election shall have been properly made only if the Exchange Agent shall have actually received a properly completed Election Form by the Election Deadline. Subject to the terms of this Agreement and the Election Form, the Exchange Agent shall have reasonable discretion to determine whether any election has been properly or timely made and to disregard immaterial defects in any Election Form, and any good faith decisions of the holders of certificatesExchange Agent regarding such matters shall be binding and conclusive. All elections will be irrevocable.
      (c) Any Election Form received by the Exchange Agent after the Election Deadline shall be deemed to be a Combination Election and any holder of Company Common Shares (the "Company Share Certificates"),Stock not returning an Election Form to the Exchange Agent shall be deemed to have made a Combination Election. In addition, if the Exchange Agent shall have determined that any purported Stock Election or Cash Election was not properly made, such purported Stock Election or Cash Election shall be deemed to be of no force and effect and the holder of shares of Company Common Stock making such purported Stock Election or Cash Election shall for exchange in accordance withall purposes hereof be deemed to have made a Combination Election.
      2.3     Proration and Redesignation Procedures.
      (a) All shares of Company Common Stock which are subject to Cash Elections, and that portion of shares of Company Common Stock which are subject to Combination Elections and would, but for the application of this Article II, a sufficientSection 2.3, be converted into Cash Consideration, are referred to herein as “Cash Election Shares.” All shares of Company Common Stock which are subject to Stock Elections, and that portion of shares of Company Common Stock which are subject to Combination Elections and would, but

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for the application of this Section 2.3, be converted into Stock Consideration, are referred to herein as “Stock Election Shares.
      (b) If, after the results of the Election Forms are calculated, the number of certificates forshares of Company Common Stock to be converted into shares of Wintrust Common Stock (the "Wintrustexceeds the Maximum Stock Certificates")Election Number, Wintrust shall cause the Exchange Agent to determine the number of Stock Election Shares which must be redesignated as Cash Election Shares in order to reduce the number of such shares to the Maximum Stock Election Number. All holders who have Stock Election Shares shall, on a pro rata basis, have such number of their Stock Election Shares redesignated as Cash Election Shares so that the Maximum Stock Election Number is achieved.
      (c) If, after the results of the Election Forms are calculated, the number of shares of Company Common Stock to be issued pursuantconverted into cash exceeds the Maximum Cash Election Number, Wintrust shall cause the Exchange Agent to determine the number of Cash Election Shares which must be redesignated as Stock Election Shares in order to reduce the amount of such cash to the Maximum Cash Election Number. All holders who have Cash Election Shares shall, on a pro rata basis, have such number of their Cash Election Shares redesignated as Stock Election Shares so that the Maximum Cash Election Number is achieved.
      (d) Notwithstanding the foregoing, Wintrust may, in its sole discretion, taking into account the actual results of the election process described in Section 1.4(a)2.2, direct at any time prior to the Effective Time that the redesignation procedures provided in this Section 2.3 be waived in whole or in part. In such event, the percentage limits specified in Section 2.1(c) for the Maximum Cash Election Number and the Maximum Stock Election Number, respectively, shall be disregarded and the procedures provided for in clause (b) or (c) above shall be applied substituting such percentage limits as Wintrust shall designate between the percentage limits specified in Section 2.1(c) and the percentages reflected in the actual results of such election process,provided,however, and sufficient cash for paymentthat such actions would not adversely affect the Merger from qualifying as a tax-free reorganization under Section 368(a) of (a) the aggregate Per ShareCode.
      (e) After the redesignation procedures, if any, required by this Section 2.3 are completed, all Cash Election Shares shall be converted into the right to receive the Cash Consideration, and all Stock Election Shares shall be converted into the right to receive the Stock Consideration. Certificates previously evidencing shares of Company Common Stock (“Company Stock Certificates”) shall be exchanged, as applicable, for (i) certificates evidencing the Stock Consideration, or (b) the Cash Consideration, multiplied in each case by the number of shares previously evidenced by the canceled Company Stock Certificate, upon the surrender of such certificates in accordance with the provisions of Section 1.4(b) and (b) cash in lieu of any fractional shares of Wintrust Common Stock in accordance with Section 2.2. Such Wintrust Stock Certificates and cash, together with any dividends or distributions with respect thereto paid after the Effective Time, are referred to in this Article II as the "Conversion Fund." Wintrust shall be solely responsible for the payment of any fees and expenses of the Exchange Agent. A-3 2.2 2.5, without interest.
      2.4     No Fractional Shares. Notwithstanding anything to the contrary contained in this Agreement, no fractional shares of Wintrust Common Stock shall be issued as Stock Consideration in the Merger. Each holder of shares of Company Common SharesStock who would otherwise be entitled to receive a fractional part of a share of Wintrust Common Stock pursuant to Section 1.4(a)this Article II shall instead be entitled to receive an amount in cash (without interest) rounded to the nearest whole cent, determined by multiplying the Wintrust Common Stock Price by the fractional share of Wintrust Common Stock to which such former holder would otherwise be entitled. 2.3
      2.5     Exchange of Certificates.
      (a) As soon as practicable At or prior to the Effective Time, Wintrust shall authorize the issuance of and shall make available to the Exchange Agent, for the benefit of the holders of Company Stock Certificates for exchange in accordance with this Article II, (i) a sufficient number of certificates for shares of Wintrust Common Stock (the “Wintrust Stock Certificates”) to be issued pursuant to Section 2.3, (ii) sufficient cash for payment of the Cash Consideration pursuant to Section 2.3, and (iii) sufficient cash for payment of cash in lieu of any fractional shares of Wintrust Common Stock in accordance with Section 2.4. Such Wintrust Stock Certificates and cash, together with any dividends or distributions with respect thereto paid

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after the Effective Time, are referred to in this Article II as the “Conversion Fund.” Wintrust shall be solely responsible for the payment of any fees and in no event later thanexpenses of the Exchange Agent.
      (b) Within five (5) business days thereafter,after the Closing Date, the Surviving Corporation shall cause the Exchange Agent pursuant to documentation reasonably satisfactory to Wintrust and the Company, to mail to each holder of record of one or more Company ShareStock Certificates a letter of transmittal (which shall specify that delivery shall be effected, and risk of loss and title to Company ShareStock Certificates shall pass, only upon delivery of such certificates to the Exchange Agent) and instructions for use in effecting the surrender of the Company ShareStock Certificates pursuant to this Agreement.
      (c) Upon proper surrender of a Company ShareStock Certificate for exchange to the Exchange Agent, after the Effective Time, together with such properly completed letter of transmittal, duly executed, the holder of such Company ShareStock Certificate shall be entitled to receive in exchange therefor (i) a Wintrust Stock Certificate representing that numberhis or her portion of whole shares of Wintrust Common Stock to whichthe Merger Consideration (in the form or forms elected by such holder subject to the provisions of this Article II) deliverable in respect of the shares of Company Common Shares shall have become entitled pursuant to Section 1.4(a) (after taking into account all Company Common Shares then heldStock represented by such holder), (ii) a check (or wire transfer, as described below) representing the aggregate Per Share Cash Consideration to which such holder of Company Common Shares shall have become entitled pursuant to Section 1.4(b) (after taking into account all Company Common Shares then held by such holder)Stock Certificate, and (iii) a check (or wire transfer, as described below) representing the amount of any cash in lieu of fractional shares that such holder has the right to receive pursuant to Section 2.2 in respect of such Company ShareStock Certificate and the Company Share Certificate so surrendered shall forthwith be canceled. No interest will be paid or accrued on any Per Share Cashthe Merger Consideration or cash in lieudeliverable upon surrender of fractional shares payable to holders ofa Company Share Certificates. Any holder of Company Common Shares entitled to receive an aggregate amount of Per Share Cash Consideration and cash in lieu of fractional shares equal to or greater than $500,000 shall be entitled to receive such amount by wire transfer to an account designated in writing by such holder to Wintrust not less than two (2) business days prior to the Closing Date, which wire transfer shall be initiated immediately following the Effective Time. (b)Stock Certificate.
      (d) If any Wintrust Stock Certificate is to be issued in a name other than that in which the Company ShareStock Certificate surrendered in exchange therefor is registered, it shall be a condition of the issuance thereof that the Company ShareStock Certificate so surrendered shall be properly endorsed (or accompanied by an appropriate instrument of transfer) and otherwise in proper form for transfer, and that the person requesting such exchange shall pay to the Exchange Agent in advance any transfer or other taxes required by reason of the issuance of a Wintrust Stock Certificate in any name other than that of the registered holder of the Company ShareStock Certificate surrendered, or required for any other reason, or shall establish to the satisfaction of the Exchange Agent that such tax has been paid or is not payable. (c)
      (e) After the Effective Time, there shall be no transfers on the stock transfer books of the Company of the shares of Company Common SharesStock that were issued and outstanding immediately prior to the Effective Time. (d)
      (f) Any portion of the Conversion Fund that remains unclaimed by the shareholders of the Company for twelve (12) months after the Effective Time shall be paid to the Surviving Corporation.Corporation, or its successors in interest. Any shareholders of the Company who have not theretofore complied with this Article II shall thereafter look only to the Surviving Corporation, or its successors in interest, for the issuance of certificates representing shares of Wintrust Common Stock, the payment of the Per Share Cash Consideration and the payment of cash in lieu of any fractional shares and any unpaid dividends and distributions on Wintrust Common Stock deliverable in respect of each share of Company Common ShareStock such shareholder holds as determined pursuant to this Agreement, in each case, without any interest thereon.Agreement. Notwithstanding the foregoing, none of Wintrust the(including in its capacity as Surviving Corporation,Corporation), the Exchange Agent or any other person shall be liable to any former holder of shares of Company Common Shares,Stock or Outstanding Company Options, for any amount delivered in good faith to a public official pursuant to applicable abandoned property, escheat or similar laws. A-4 (e)
      (g) In the event any Company ShareStock Certificate shall have been lost, stolen or destroyed, upon the making of an affidavit of that fact by the person claiming such Company ShareStock Certificate to be lost, stolen or destroyed and, if reasonably required by the Surviving Corporation, the posting by such person of a bond in such amount as the Exchange Agent may determine is reasonably necessary as indemnity against any claim that may be made against it with respect to such Company ShareStock Certificate, the Exchange Agent will issue in exchange for such lost, stolen or destroyed Company Share Certificate, (i) a Wintrust Stock Certificate, representingand in accordance with Article II, the shares of Wintrust Common StockPer Share Merger Consideration (in the form or forms pursuant to the election procedures set forth in this Article II) and cash in lieu of any fractional shares deliverable in respect thereof pursuant to this Agreement and (ii) the Per Share Cash Consideration. (f)Agreement.
      (h) No dividends or other distributions declared with respect to Wintrust Common Stock and payable to the holders of record thereof after the Effective Time shall be paid to the holder of any unsurrendered Company ShareStock Certificate until the holder thereof shall surrender such Company Share Stock

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Certificate in accordance with this Article II and no interest shall be payable on any cash to be paid in lieu of fractional shares or the Per Share Cash Consideration.II. Promptly after the surrender of a Company ShareStock Certificate in accordance with this Article II, the record holder thereof shall be entitled to receive any such dividends or other distributions, without interest thereon, which theretofore had become payable with respect to shares of Wintrust Common Stock represented by such Company ShareStock Certificate. No holder of an unsurrendered Company ShareStock Certificate shall be entitled, until the surrender of such Company ShareStock Certificate, to vote the shares of Wintrust Common Stock into which Company Common SharesStock shall have been converted.
ARTICLE 3 III
REPRESENTATIONS AND WARRANTIES
CONCERNING THE COMPANY
      The Company hereby represents and warrants to Wintrust as follows:
      3.1     Organization.
      (a) The Company is duly registered as a bank holding company under the Bank Holding Company Act of 1956, as amended (the "BHCA"BHCA), is a corporation duly organized, and validly existing and in good standing under the laws of the State of Wisconsin,Illinois, and has the corporate power and authority to own its properties and to carry on its business as presently conducted. The Company is duly qualified and in good standing as a foreign corporation in each other jurisdiction where the location and character of its properties and the business conducted by it require such qualification, except where the failure to be so qualified would not have a Material Adverse Effect on the Company. As used in this Agreement, "MaterialMaterial Adverse Effect"Effect” shall mean, with respect to a Party shall meanthe Company or Wintrust, as the case may be, a material adverse effect on (i) the business, assets, properties, results of operations or financial condition of thata Party and its subsidiaries, taken as a whole or (ii) the ability of thata Party to consummate the Merger;provided,however, that a Material Adverse Effect shall not be deemed to result from: (1) changes in banking, andmortgage banking or mortgage lending or similar laws of general applicability or interpretations thereof by Governmental Authorities (as defined in Section 3.5), or other changes affecting depository institutions (including banks and their holding companies) generally, including changes in general economic conditions and changes in prevailing interest and deposit rates;rates and factors affecting the financial markets as a whole; (2) changes resulting from transaction expenses incurred in connection with this Agreement and the Merger, including reasonable legal, accounting, appraisal and investment bankers' fees; (3) changes in generally accepted accounting principles ("GAAP"(“GAAP) or regulatory accounting requirements applicable to banks and their holding companies, as such changes would apply to the financial statements of a Party on a consolidated basis,basis; (3) changes resulting from transaction expenses (such as legal, accounting, investment banker or other professional fees) incurred in connection with this Agreement and the Merger, including the costs of litigation defending any of the transactions contemplated by this Agreement; (4) the payment by the Company or the Bank of amounts due to, or provision of any other benefits to, any officers or employees of the Company or the Bank in accordance with the terms of any employment agreements or Benefit Plans.Plans (as defined in Section 3.20(a)); and (5) actions or omissions taken by a Party as required hereunder or taken with the prior written consent of the other Party.
      (b) Except as set forthOther than (i) the Bank and (ii) those inactive subsidiaries and other ownership interests described on Schedule 3.1(b), other than (i)neither the Company nor the Bank (ii) Town Bankshares Capital Trust I, a Delaware statutory trust (the "Trust") and (iii) Town Investment Corp., a Nevada corporation ("TIC", and together with the Bank and the Trust, the "Subsidiaries"), the Company does not own,owns, whether directly or indirectly, any voting stock, equity securities or membership, partnership, joint venture or similar ownership interest in any corporation, association, partnership, limited liability company or other entity.
      (c) The Bank is aan Illinois state bank, duly chartered and organized, validly existing and currently authorized to transact the business of banking under the laws of the Statestate of Wisconsin,Illinois, and has the requisite power and authority to own its properties and to carry on its business as presently conducted. A-5 (d) TIC is a corporation duly organized, validly existing and in good standing under the laws of the State of Nevada, and has the corporate power and authority to own its properties and to carry on its business as presently conducted. TIC is duly qualified and in good standing as a foreign corporation in each other jurisdiction where the location and character of its properties and the business conducted by it require such qualification, except where the failure to be so qualified would not have a Material Adverse Effect on the Company. (e) The Trust is a statutory trust duly organized, validly existing and in good standing under the laws of the State of Delaware, and has the trust power and authority to own its properties and to carry on its business as presently conducted. The Trust is duly qualified and in good standing as a foreign entity in each other jurisdiction where the location and character of its properties and the business conducted by it require such qualification, except where the failure to be so qualified would not have a Material Adverse Effect on the Company.
      3.2     Organizational Documents; Minutes and Stock Records. The Company has furnished Wintrust with copies of the articles of incorporation and by-laws of each of the Company and TIC, the charter and by-laws of the Bank, and the organizational documents of the Trust, in each case as amended to the date hereof, and with such other documents as requested by Wintrust relating to the authority of the Company and its Subsidiariesthe Bank to conduct their respective businesses. All such documents are complete and correct. The stock registers (or equivalent records of ownership) and minute books of the Company and its Subsidiariesthe

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Bank are each complete, correct and accurately reflect, in each case in all material respects, all meetings, consents, and other actions of the organizers, incorporators, shareholders, members, board of directors, partners, managers, and committees of the board of directors or managers of the Company and the Subsidiaries,Bank, respectively, and all transactions reported to the Company or the Subsidiaries, as the case may be, by their respective shareholders, partners or members, in such entity'sentity’s capital stock partnership interests or limited liability interests, as the case may be, occurring since the date of incorporation, formation orinitial organization of the Company and the Subsidiaries, as the case may be.Bank, respectively.
      3.3     Capitalization.
      (a) The Company.Company. The authorized capital stock of the Company consists of 500,00010,000,000 shares of common stock, par value $0.01$0.05 per share, of which 298,2062,751,098 shares are issued and outstanding as of the date of this Agreement and no800 shares are held in treasury and 50,000 shares oftreasury. The Company has no preferred stock par value $0.01 per share, of which no shares areauthorized, issued or outstanding. The issued and outstanding shares of Company Common SharesStock have been duly and validly authorized and issued and are fully paid and nonassessable (except as provided in Section 180.0622(2)(b) of the Wisconsin Act, as interpreted).nonassessable. The Company has no issued and has outstanding warrantsoptions for the purchase of 13,750 shares of Company Common Shares. NoStock (the “Options”), the beneficial and record holders of which are set forth on Schedule 3.3(a). The Options have been duly authorized by all necessary corporate action (including shareholder approval if necessary), have been validly executed, issued and delivered by the Company, constitute the legal, valid and binding obligations of the Company, and are enforceable as to the Company in accordance with their terms. The shares of Company Common SharesStock to be issued upon exercise of the Options are validly authorized and, upon such exercise of the Options in accordance with their terms, including the full payment of the exercise price thereunder, will be validly issued, fully paid, and nonassessable. The Company Common Stock is subject to anyno preferences, qualifications, limitations, restrictions or special or relative rights under the Company'sCompany’s articles of incorporation. Except for the Outstanding Company Options, under the Company Option Plan, there are no options,warrants, agreements, contracts, or other rights in existence to purchase or acquire from the Company any shares of capital stock of the Company, whether now or hereafter authorized or issued.
      (b) The Bank.Bank. The authorized capital stock of the Bank consists of 50,000142,000 shares of common stock, par value $100$9.00 per share, 12,000all of which are issued and outstanding and are owned of record and beneficially by the Company.outstanding. The issued and outstanding shares of common stock of the Bank have been duly and validly authorized and issued and are fully paid and nonassessable (except as provided in Chapter 221 of12 U.S.C. §55) and owned by the Wisconsin Statutes, as interpreted), and are free of preemptive rights.Company. There are no options, agreements, contracts, or other rights in existence to purchase or acquire from the Bank any shares of capital stock of the Bank, whether now or hereafter authorized or issued. Other than as set forth onin Schedule 3.3(b), the Bank does not own, whether directly or indirectly, any voting stock, equity securities or membership, partnership, joint venture or similar ownership interest in any corporation, association, partnership, limited liability company or other entity. (c) TIC. The authorized capital stock of TIC consists of 2,500 shares of common stock, no par value per share, all of which are issued and outstanding and are owned of record and beneficially by the Bank. The issued and outstanding shares of common stock of TIC have been duly and validly authorized and issued and are fully paid and nonassessable, and are free of preemptive rights. There are no options, agreements, contracts, or other rights in existence to purchase or acquire from TIC any shares of capital stock of TIC, whether now or hereafter authorized or issued. TIC does not own, whether directly or indirectly, any voting stock, equity A-6 securities or membership, partnership, joint venture or similar ownership interest in any corporation, association, partnership, limited liability company or other entity. (d) The Trust. The Trust has authorized and issued 186 common securities, liquidation amount $1,000 per common security, all of which are owned of record and beneficially by the Company, and 6,000 capital securities, liquidation amount $1,000 per capital security, all of which are issued and outstanding. The issued and outstanding securities of the Trust have been duly and validly authorized and issued and represent undivided beneficial interests in the assets of the Trust, and are free of preemptive rights. There are no options, agreements, contracts, or other rights in existence to purchase or acquire from the Trust any securities of the Trust, whether now or hereafter authorized or issued. The Trust does not own, whether directly or indirectly, any voting stock, equity securities or membership, partnership, joint venture or similar ownership interest in any corporation, association, partnership, limited liability company or other entity.
      3.4     Authorization; No Violation. The execution and delivery of this Agreement and the performance of the Company'sCompany’s obligations hereunder have been duly and validly authorized by the Board of Directors of the Company (the "Company Board"Company Board), and do not violate or conflict with the Company'sCompany’s articles of incorporation, by-laws, the WisconsinIllinois Act, or any applicable law, court order or decree to which the Company or the SubsidiariesBank is a party or subject, or by which the Company, or the SubsidiariesBank or their respective properties are bound, subject to the approval of this Agreement and the Merger by the shareholders of the Company. Except as set forth on Schedule 3.4, the execution and delivery of this Agreement and the performance of the Company'sCompany’s obligations hereunder do not and will not result in any default or give rise to any right of termination, cancellation or acceleration under any material note, bond, mortgage, indenture or other agreement by which the Company, or the SubsidiariesBank or their respective properties are bound. This Agreement, when executed and delivered, and subject to the approval of the Company's shareholders and the regulatory approvals described in Sections 7.3 and 8.3,Section 3.5, will be a valid, binding and enforceable obligation of the Company, subject to applicable bankruptcy, insolvency, reorganization, moratorium or similar laws affecting creditors generally and to general principles of equity.
      3.5     Consents and Approvals. No consents or approvals of, or filings or registrations with, any court, administrative agency or commission or other governmental authority or instrumentality (each, a "Governmental Authority"Governmental Authority) or with any third party are necessary in connection with the execution and delivery by the Company of this Agreement and the consummation by the Company of the Merger except

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for (a) those third-party consents, approvals, filings or registrations set forth on Schedule 3.5, (b) the filing by Wintrust of an application (the "Federal Reserve Application") with the Board of Governors of the Federal Reserve System (the "Federal Reserve"Federal Reserve) under the BHCA (the “Federal Reserve Application”), (c) the filing by the CompanyWintrust of an application (the "WDFI Application") with the DivisionIllinois Department of Financial and Professional Regulation (the “IDFPR”) under the Illinois Banking of the WDFI,Act (the “IDFPR Application”), (d) the filing with the Securities and Exchange Commission (the "Commission"Commission) of a proxy statement in definitive form and a registration statement on an appropriate form under the Securities Act of 1933, as amended (the "Securities Act"Securities Act), relating to the meeting of the Company'sCompany’s shareholders to be held in connection with this Agreement and the Merger and the registration of the shares of Wintrust Common Stock (the "ProxyProxy Statement/Prospectus" Prospectus), (e) the filing of the Articles of Merger with the Illinois Secretary of State under Section 11.25 of the State of Illinois under the Illinois Act and with the WDFI under the Wisconsin Act, and (f) the approval of this Agreement and the Merger by the requisite vote of the shareholders of the Company.
      3.6     Financial Statements. Schedule 3.6 sets forth true and complete copies of the following financial statements (collectively, the "Financial Statements"Financial Statements): (a) the audited consolidated balance sheets of the Company as of December 31, 2004, 2003 and 2002 and the related statements of income, changes in shareholders'shareholders’ equity and cash flows for the fiscal years then ended, and (b) the unaudited consolidated interim balance sheet of the Company as of March 31, 2004September 30, 2005 (the "InterimInterim Balance Sheet"Sheet) and the related statement of income and changes in shareholders' equity for the three-monthnine-month period then ended (together with the Interim Balance Sheet, the "InterimInterim Financial Statements"Statements). The Financial Statements (i) are complete (ii) are true and correct in all material respects as of their respective dates and (iii) have been prepared in conformity with GAAP applied on a consistent basis throughout the periods involved (except as may be indicated in any notes thereto).involved. Each balance sheet (including any related notes) included in the Financial Statements presents fairly the consolidated financial position of the Company and the Subsidiaries as of the date thereof, and each income statement (including any related notes) and statement of cash flow included in the Financial Statements presents fairly the consolidated results of operations and cash flow, respectively, of the Company and the Subsidiaries for the period set forth therein;provided,however, that the Interim Financial Statements contain all adjustments necessary for a fair presentation, subject to normal, A-7 recurring year-end adjustments (which adjustments will not be, individually or in the aggregate, material), and omission of footnote disclosure.lack footnotes. Each of the audited Financial Statements has been certified by the Company'sCompany’s independent auditor, who havehas expressed an unqualified opinion on such Financial Statements.Statements, and each of the Interim Financial Statements has been certified by the Company’s chief executive officer and principal accounting officer. The books, records and accounts of each of the Company and the Bank accurately and fairly reflect, in reasonable detail, all transactions and all items of income and expense, assets and liabilities and accruals relating to the Company and the Subsidiaries.Bank, as applicable.
      3.7     No Undisclosed Liabilities. Except as set forth on Schedule 3.7, the The Company has no liabilities, whether accrued, absolute, contingent, or otherwise, existing or arising out of any transaction or state of facts existing on or prior to the date hereof, except (a) as and to the extent disclosed, reflected or reserved against in the Financial Statements, (b) as and to the extent arising under contracts, commitments, transactions, or circumstances identified in the Schedules provided for herein, excluding any liabilities for Company breaches thereunder, and (c) liabilities, not material in the aggregate and incurred in the Ordinary Course of Business, which, under GAAP, would not be required to be reflected on a balance sheet prepared as of the date hereof, and (d) liabilities, not materialhereof. An action taken in the aggregate and incurred in the Ordinary Course of Business since March 31, 2004. For purposes” shall mean an action taken in the ordinary course of business of the preceding subsection (d), anyCompany or the Bank, as applicable, consistent with past custom and practice (including with respect to quantity and frequency) and where for such action to be taken, no separate authorization by the Company Board or the board of directors of the Bank, as applicable, is required. Any liabilities incurred in connection with litigation or judicial, administrative or arbitration proceedings or claims against the Company shall not be deemed to be incurred in the Ordinary Course of Business. An action taken inNotwithstanding the "Ordinary Courseforegoing, the making or renewal of Business" shall mean an action taken in the ordinary course of businessloans or other credit arrangements to directors or executive officers of the Company or a Subsidiary, as applicable, consistent with custom and practice (including with respect to quantity and frequency) and where for such action to be taken, no separate authorization by the Company Board or a Subsidiary's board of directors (other thanBank made in accordance with all regulatory requirements and that are consistent with the Company's loan policy), as applicable, is required.Company’s and the Bank’s past practice and custom shall be deemed to have been made in the Ordinary Course of Business.

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      3.8     Loans; Allowance for Loan Losses.Loss Reserves.
      (a) Each outstanding loan, loan agreement, note, lease or other borrowing agreement, any participation therein and any guaranty, renewal or extension thereof (collectively, "Loans"Loans) reflected on the books and records of the Bank is evidenced by appropriate and sufficient documentation and constitutes the legal, valid and binding obligation of the obligor named therein, enforceable in accordance with its terms, except to the extent such enforceability may be limited by applicable bankruptcy, insolvency, reorganization, moratorium or other similar laws affecting the enforcement of creditors'creditors’ rights and remedies generally from time to time in effect and by applicable laws which may effect the availability of equitable remedies. No obligor named in any Loan has provided notice (whether written or, to the knowledge of the Company, oral) to the Company or the Bank that such obligor intends to attempt to avoid the enforceability of any term of any Loan under any such laws or equitable remedies, and no Loan is subject to any valid defense, set-off, or counterclaim that has been asserted with respect to such Loan. All Loans that are secured, as evidenced by the appropriate and sufficient ancillary security documents, are so secured by valid and enforceable liens, except to the extent such enforceability may be limited by applicable bankruptcy, insolvency, reorganization, moratorium or other similar laws affecting the enforcement of creditors' rights and remedies generally from time to time in effect and by applicable laws which may affect the availability of equitable remedies.liens. Neither the Bank nor the Company has entered into any loan repurchase agreements.
      (b) The allowancereserves for loan and lease losses shown on each of the balance sheets contained in the Financial Statements are adequate in the reasonable judgment of the Companymanagement and are consistent with the standards of the Federal Deposit Insurance Corporation (the “FDIC”) and under GAAP to provide for losses, net of recoveries relating to loans and leases previously charged off, on loans and leases outstanding (including accrued interest receivable) as of the applicable date of such balance sheet. The aggregate loan balances of the Bank as of March 31, 2004September 30, 2005 in excess of such reserves as shown on the Interim Balance Sheet are, to the knowledge of the Company, collectible in accordance with their respective terms.
      3.9     Properties and Assets.
      (a) Real Property.Property. Attached as Schedule 3.9(a) is a Schedule of Real Property, which sets forth a complete and correct listdescription of all real property owned or leased by the Company or the SubsidiariesBank or in which either the Company or the SubsidiariesBank has an interest (other than as a mortgagee). None of the Company or the Subsidiaries owns, or has owned, anyNo real property including any real property that may be classified under applicable banking regulationsor improvements are carried on the Bank’s books and records as Other Real Estate Owned. The Company and the SubsidiariesBank own, or have a valid right to use or a leasehold interest in, all real property used by them in the conduct of their respective businesses as such businesses are presently conducted. Except as otherwise set forth on Schedule 3.9(a), the ownership or leasehold interest of the Company or the Bank in such real property is not subject to any mortgage, pledge, lien, option, conditional sale agreement, encumbrance, security interest, title exceptions or restrictions or claims or charges of any kind (collectively, "Encumbrances"Encumbrances), except for Permitted Encumbrances. A-8 As used in this Agreement, "Permitted Encumbrances"Permitted Encumbrances shall mean (i) Encumbrances arising under conditional sales contracts and equipment leases with third parties under which the Company or the SubsidiariesBank is not delinquent or in default, (ii) carriers'carriers’, workers'workers’, repairers'repairers’, materialmen's,materialmen’s, warehousemen liens'liens’ and similar Encumbrances incurred in the Ordinary Course of Business, (iii) Encumbrances for taxes not yet due and payable or that are being contested in good faith and for which proper reserves have been established and reflected on the Interim Balance Sheet, (iv) minor defects in title to real property or easements that do not materially impair the intended use thereof, (v) zoning and similar restrictions on the use of real property, (v)and (vi) in the case of any leased asset,assets, (A) the rights of any lessor under the applicable lease agreement or any Encumbrance granted by any such lessor and (B) any statutory lien for amounts not yet due and payable, or that are being contested in good faith and for which proper reserves have been established and reflected on the Interim Balance Sheet, and (vi) Encumbrances that do not, individually or in the aggregate, materially detract from or interfere with any use of or impair the value of any asset as currently used.Sheet. All material certificates, licenses and permits required for the lawful use and occupancy of any real property by the Company or the Subsidiaries,Bank, as the case may be, have been obtained and are in full force and effect.
      (b) Personal Property.Property. Attached as Schedule 3.9(b) is a Schedule of Tangible Personal Property, which sets forth a complete and correct listdescription of each item ofall tangible personal property owned by the Company or the SubsidiariesBank or used by the Company or the SubsidiariesBank in the conduct of their respective businesses that is reflected as a capital asset onin the Interim Balance Sheet. TheExcept as otherwise set forth on

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Schedule 3.9(b), (i) the Company andor the Subsidiaries own,Bank owns, or havehas a valid right to use or a leasehold interest in, all such personal property, (ii) all such property is owned free and clear of any Encumbrances, except for Permitted Encumbrances and (iii) all such property is in adequategood working condition, for the purposes for which it is being used, normal wear and tear excepted.
      (c) Assets.Assets. The assets reflected on the Interim Balance Sheet or identified in this Agreement or on the Schedules provided for herein include all of the material assets (i) owned by the Company or the Subsidiaries,Bank, except for those assets subsequently disposed of or purchased by the Company or the SubsidiariesBank for fair value in the Ordinary Course of Business, and (ii) used, intended or intendedrequired for use by the Company or the SubsidiariesBank in the conduct of their respective businesses.
      3.10     Material Contracts. Attached as Schedule 3.10 is a complete and correct listSchedule of all Material Contracts, and the Company has previously delivered or made available to Wintrust true and complete copies of allwhich have been delivered to Wintrust, except with respect to those Material Contracts. "Material Contracts" mean each of the following contracts, commitments, or arrangements, whether written or oral (andContracts described in Section 3.10(f) for which the Company has delivered to Wintrust a complete and correct list and made available to Wintrust copies of such items upon request. “Material Contracts” include every contract, commitment, or arrangement (whether written descriptionsor oral) of the terms and conditionsa material nature (or that assumes materiality because of all oral Material Contracts),its continuing nature) under which the Company or the SubsidiariesBank is obligated on the date hereof: (a) all consulting arrangements, and contracts for professional, advisory, and other services,hereof, including contracts under which the Company or the Subsidiaries performs services for others; (b) all leases of real estate; (c) all contracts, commitments and agreements for the acquisition, development or disposition of real or personal property other than conditional sales contracts and security agreements whereunder total future payments are, in each instance, less than $25,000; (d) all contracts relating to the employment, engagement, compensation or termination of directors, officers, employees, consultants or agents of the Company or the Subsidiaries, and all pension, retirement, profit sharing, stock option, stock purchase, stock appreciation, insurance or similar plans or arrangements for the benefit of any employees, officers or directors of the Company or the Subsidiaries, including all Benefit Plans; (e) all loans, loan commitments, promissory notes, letters of credit or other financial accommodations or arrangements or evidences of indebtedness, including modifications, waivers or amendments thereof, extended to or for the benefit of the Company or the Subsidiaries; (f) all loans, loan commitments, promissory notes, letters of credit or other financial accommodations or arrangements or evidences of indebtedness, including modifications, waivers or amendments thereof, extended to or for the benefit of any single borrower or related group of borrowers if the aggregate amount of all such loans, loan commitments, promissory notes, letters of credit or other financial accommodations or A-9 arrangements or evidences of indebtedness extended to such borrower or related group of borrowers exceeds $1,000,000; (g) all union and other labor contracts; (h) all agreements, contracts, mortgages, loans, deeds of trust, leases, commitments, indentures, notes, instruments and other arrangements which are with officers or directors of the Company or the Subsidiaries, any "affiliates" of the Company or the Subsidiaries within the meaning of Section 23A of the Federal Reserve Act or any record or beneficial owner of 5% or more of Company Common Shares, or any member of the immediate family or a related interest (as such terms are defined in 12 C.F.R. ss.215.2(m)) of any such person, excepting any ordinary and customary loans and deposits that comply with applicable banking regulations; (i) any contract involving total future payments by the Company or the Subsidiaries of more than $25,000 or which requires performance by the Company or the Subsidiaries beyond the second anniversary of the Closing Date, that by its terms does not terminate or is not terminable by the Company or the Subsidiaries without penalty within 30 days after the date of this Agreement; (j) except for provisions of the articlesfollowing:
      (a) all consulting arrangements, and contracts for professional, advisory, and other services, including contracts under which the Company or the Bank performs services for others;
      (b) all leases of real estate and personal property;
      (c) all contracts, commitments and agreements for the acquisition, development or disposition of real or personal property other than conditional sales contracts and security agreements whereunder total future payments are, in each instance, less than $50,000;
      (d) all contracts relating to the employment, engagement, compensation or termination of directors, officers, employees, consultants or agents of the Company or the Bank, and all pension, retirement, profit sharing, stock option, stock purchase, stock appreciation, insurance or similar plans or arrangements for the benefit of any employees, officers or directors of the Company, including all Benefit Plans as defined in Section 3.20;
      (e) all loans, loan commitments, promissory notes, letters of credit or other financial accommodations or arrangements or evidences of indebtedness, including modifications, waivers or amendments thereof, extended to or for the benefit of the Company or the Bank;
      (f) all loans, loan commitments, promissory notes, letters of credit or other financial accommodations or arrangements or evidences of indebtedness, including modifications, waivers or amendments thereof, extended to or for the benefit of any single borrower or related group of borrowers if the aggregate amount of all such loans, loan commitments, promissory notes, letters of credit or other financial accommodations or arrangements or evidences of indebtedness extended to such borrower or related group of borrowers exceeds $500,000;
      (g) all union and other labor contracts;
      (h) all agreements, contracts, mortgages, loans, deeds of trust, leases, commitments, indentures, notes, instruments and other arrangements which are with officers or directors of the Company or the Bank, any “affiliates” of the Company or the Bank within the meaning of Section 23A of the Federal Reserve Act or any record or beneficial owner of 5% or more of Company Common Stock, or any member of the immediate family or a related interest (as such terms are defined in 12 C.F.R. §215.2(m)) of any such person, excepting any ordinary and customary loans and deposits that comply with applicable banking regulations;
      (i) any contract involving total future payments by the Company or the Bank of more than $50,000 or which requires performance by the Company or the Bank beyond the second anniversary

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of the Closing Date, that by its terms does not terminate or is not terminable by the Company or the Bank without penalty within 30 days after the date of this Agreement;
      (j) except for provisions of the certificate of incorporation and by-laws of each of the Company and TIC, the charter and by-laws of the Bank, all contracts under which the Company or the Bank has any obligation, direct, indirect, contingent or otherwise, to assume or guarantee any liability or to indemnify any person (other than in a fiduciary capacity);
      (k) all joint venture or marketing agreements with any other person or entity; and
      (l) all other material contracts, made other than in the Ordinary Course of Business of the Company or the Bank, to which the Company or the Bank is a party or under which the Company or the Bank and the organizational documents of the Trust, all contracts under which the Company or the Subsidiaries has any obligation, direct, indirect, contingent or otherwise, to assume or guarantee any liability or to indemnify any person (other than in a fiduciary capacity); (k) all joint venture or marketing agreements with any other person or entity; and (l) all other material contracts, made other than in the Ordinary Course of Business of the Company or the Subsidiaries, to which the Company or the Subsidiaries is a party or under which the Company or the Subsidiaries is obligated.

      3.11     No Defaults. Each of the Company and the SubsidiariesBank has fulfilled and taken all action reasonably necessary to date to enable it to fulfill, when due, all of its material obligations under all Material Contracts to which it is a party. There are no breaches or defaults by the Company or the SubsidiariesBank under any Material Contract that could give rise to a right of termination or claim for material damages under such Material Contract, and no events haveevent has occurred that, with the lapse of time or the election of any other party, will become defaultssuch a breach or default by the Company or the Subsidiaries.Bank. To the Company's knowledge of the Company, no breach or default by any other party under any Material Contract has occurred or is threatened that will or could impair the ability of the Company or the Bank to enforce any of its material rights under such Material Contract.
      3.12     Conflict of Interest Transactions. Except as set forth on Schedule 3.12, no principal officer or director of the Company or the Subsidiaries,Bank, or holder of 10% or more of the Company Common SharesStock or any member of the immediate family or a related interest (as such terms are defined in 12 C.F.R. ss.215.2(m)§215.2(m)) of such person: (a) has any direct or indirect ownership interest in (i) any entity which does business with, or is a competitor of, the Company or the SubsidiariesBank (other than the ownership of not more than 1% of the outstanding capital stock of such entity if such stock is listed on a national securities exchange or market or is regularly traded in theover-the-counter market by a member of a national securities exchange or market) or (ii) any property or asset which is owned or used by the Company or the SubsidiariesBank in the conduct of its business; or (b) has any financial, business or contractual relationship or arrangement with the Company or the Subsidiaries,Bank, excluding any agreements and commitments entered into in respect of the Bank'sBank’s acceptance of deposits and investments or the making of any loans, in each case in the Bank's Ordinary Course of Business.Business of the Bank.
      3.13     Investments.
      (a) Set forth on Schedule 3.13(a) is a complete and correct list and description as of May 31, 2004,September 30, 2005, of all investment and debt securities, mortgage-backed and related securities, marketable equity securities and securities purchased under agreements to resell that are owned by the Company or the Subsidiaries,Bank, other than in a fiduciary or agency capacity (the "Investment Securities"Investment Securities). Each of theThe Company and the SubsidiariesBank each has good and marketable title to all Investment Securities held by it, free and clear of all Encumbrances, except for Permitted Encumbrances, and except to the extent such Investment Securities are pledged in the Ordinary Course of Business consistent with prudent banking practices to secure the obligations of the Company or the Subsidiaries.Bank. The Investment Securities are valued on the books of the Company and each of the SubsidiariesBank in accordance with GAAP. A-10
      (b) Except as set forth on Schedule 3.13(b), and as may be imposed by applicable securities laws and the documents and instruments governing the terms of such securities, none of the Investment Securities is subject to any restriction, whether contractual or statutory, that materially impairs the ability of the Company or the SubsidiariesBank freely to dispose of such investment at any time. With respect to all material repurchase agreements to which the Company or the SubsidiariesBank is a party, the Company or the Subsidiaries,Bank, as the case may be, has a valid, perfected first lien or security interest in the securities or other collateral securing each such repurchase agreement, and the value of the collateral securing each such repurchase agreement equals or exceeds the amount of the debt secured by such collateral under such agreement.

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      (c) NeitherExcept as set forth on Schedule 3.13(c), neither the Company nor the SubsidiariesBank has sold or otherwise disposed of any Investment Securities in a transaction in which the acquiror of such Investment Securities or other person has the right, either conditionally or absolutely, to require the Company or the SubsidiariesBank to repurchase or otherwise reacquire any such Investment Securities.
      (d) There are no interest rate swaps, caps, floors, option agreements or other interest rate risk management arrangements to which the Company or the SubsidiariesBank is bound.
      3.14     Compliance with Laws; Legal Proceedings.
      (a) Except as set forth on Schedule 3.14, theThe Company and each of the SubsidiariesBank are each in compliance in all material respects with all applicable federal, state, county and municipal laws and regulations (i) that regulate or are concerned in any way with the ownership and operation of banks and their holding companies or the business of banking or of acting as a fiduciary, including those laws and regulations relating to the investment of funds, the taking of deposits, the lending of money, the collection of interest, the extension of credit and the location and operation of banking facilities, or (ii) that otherwise relate to or affect the business or assets of the Company or the SubsidiariesBank or the assets owned, used, occupied or managed by anyeither of them, including, without limitation, all applicable fair lending laws and other laws relating to discriminatory business practices, escrow administration, usury, due on sale and loan servicing, the USA Patriot Act of 2001, the Gramm-Leach-Bliley Act of 1999, the International Money Laundering Abatement and Anti-Terrorist Financing Act of 2001, the Fair Credit Reporting Act, the Home Mortgage Disclosure Act of 1975, the Real Estate Settlement Procedures Act of 1974, the Truth in Lending Act, the Homeowners Protection Act of 1998, the Equal Credit Opportunity Act and the Flood Disaster Protection Act of 1973, in each case as in effect and applicableexcept for matters concerning such compliance that would not be material to the Company andor the Subsidiaries and their operations.Bank.
      (b) The Company and each of the SubsidiariesBank hold all material licenses, certificates, permits, authorizations, franchises and authorizationsrights from all appropriate federal, state or other Governmental Authorities necessary for the conduct of their respective businesses and the ownership of their assets and(collectively, “Licenses”), all such licenses, certificates, permits and authorizationsLicenses are in full force and effect, and the Company has received no notice (whether written or, to the knowledge of the Company, no suspension, cancellation or limitationoral) of any of them is threatened.pending or threatened action by any Governmental Authority to suspend, revoke, cancel or limit any License.
      (c) Except as set forth on Schedule 3.143.14(c), there are no claims, actions, suits or proceedings pending or, to the knowledge of the Company, threatened or contemplated against or affecting the Company or the Subsidiaries,Bank, at law or in equity, or before any federal, state or other Governmental Authority or any arbitrator or arbitration panel, whether by contract or otherwise, and there is no decree, judgment or order or supervisory agreement of any kind in existence against or restraining the Company or the SubsidiariesBank from taking any action of any kind in connection with the business of the Company or the Subsidiaries.Bank. Except as set forth on Schedule 3.14, none of3.14(c), neither the Company ornor the SubsidiariesBank has received from any federal, state or other Governmental Authority any notice or threat (whether written or, to the knowledge of the Company, oral) of enforcement actions, or any criticism recommendation or suggestionrecommendation of a material nature, and none ofneither the Company ornor the SubsidiariesBank has any reasonable basis for believing that any such notice or threat, criticism, recommendation or suggestion not otherwise disclosed herein is contemplated.contemplated, concerning capital, compliance with laws or regulations, safety or soundness, fiduciary duties or other banking or business practices that has not been resolved to the reasonable satisfaction of such Governmental Authority.
      3.15     Insurance. Attached as Schedule 3.15 is a Schedule of Insurance, which sets forth a complete and correct list of all policies of insurance (a) in which the Company or the SubsidiariesBank is named as an insured party, which otherwise relate to or (b) pursuant to which the business,cover any assets, properties, premises, operations or propertiespersonnel of the Company or the Subsidiaries are insured andBank, or which areis owned or carried by the Company or the Subsidiaries.Bank. The Company and each of the SubsidiariesBank has in full force and effect policies of insurance issued by reputable insurance companies against loss or damage of the kinds and in the amounts identified in the policy summaries, and all A-11 premiums and costs with respect thereto are set forth on Schedule 3.15. Neither the Company nor the SubsidiariesBank has received notice (whether written or, to the knowledge of the Company, oral) from any party of interest in or to any such policies claiming any breach or violation of any provisions thereof, disclaiming or denying coverage thereof or canceling or threatening cancellation of any such insurance contracts.
      3.16     Taxes.
      (a) Except as set forth on Schedule 3.16(a),3.16, the Company and each of the Subsidiaries hasBank have each duly and timely filed (i) all federal, state and local income, real and personal property and employment tax returns, (ii) all material franchise, excise and value-added tax returns, and (iii) all other material returnsTax Returns required to be filed or delivered by the Company or the SubsidiariesBank, respectively, in connection with the Company'sCompany’s or the Subsidiaries'Bank’s business and operations, (collectively, "Returns"), all information included in such Tax Returns is accurate in all material respects, and all taxesTaxes required to be shown on such Tax Returns

A-13


as payable by the Company or the SubsidiariesBank with respect to the income of the Company or the SubsidiariesBank have been paid when due. Except as set forth on Schedule 3.16(a), noNo application for an extension of time for filing any Tax Return or consent to any extension of the period of limitations applicable to the assessment or collection of any taxTax is in effect with respect to the Company or the Subsidiaries. (b) Except as set forth on Schedule 3.16(b), neitherBank. Neither the Company nor the SubsidiariesBank is delinquent in the payment of any taxesTaxes claimed to be due from the Company or the SubsidiariesBank by any taxing authority, and adequate provisionsreserves for taxesTaxes (including any penalties and interest) payable by the Company have been made on the books of the Company and on the most recent of the Financial Statements. The Company has not received any notice (whether written or, to the knowledge of the Company, oral) of any proposed audit or proposed deficiency for any duty, tax, assessment or governmental chargeTax due from the Company or the Bank with respect to the business and operations of the Company or the Bank, as the case may be, and there are no pending audits or claims with respect thereto.
      (b) Taxes shall mean any and all taxes, charges, fees, levies or other assessments, including net income, gross receipts, excise, real or personal property, sales, withholding, social security, occupation, use, service, service use, value added, license, net worth, payroll, franchise, transfer, recording, gross income, alternative or add-on minimum, environmental, goods and services, capital stock, profits, single business, employment, severance, stamp, unemployment, customs and duties taxes, fees and charges, imposed by any taxing authority (whether domestic or foreign including any state, local or foreign government or any subdivision or taxing agency thereof), whether computed on a separate, consolidated, unitary, combined or any other basis; and such term shall include any interest, penalties or additional amounts attributable to, or imposed upon, or with respect to, any such taxes, charges, fees, levies or other assessments. “Tax Return” shall mean any report, return, document, declaration or other information or filing required to be supplied to any taxing authority or jurisdiction (foreign or domestic) with respect to Taxes.
      3.17     Environmental Laws and Regulations.
      (a) Except as set forth on Schedule 3.17, the Company and each of the Subsidiaries have been and are in compliance in all material respects with all applicable federal, state, county and municipal laws, regulations, authorizations, licenses, approvals, permits and orders relating to air, water, soil, solid waste management, hazardous or toxic substances, or the protection of health or the environment (collectively, "Environmental Laws"), including compliance in all material respects with all such Environmental Laws as they may relate to the conduct of the businesses of the Company (including acting as a trustee or fiduciary) and each of the Subsidiaries and the ownership of their respective properties and assets.Bank:
      (i) have had and now have all environmental approvals, consents, licenses, permits and orders required to conduct the businesses in which they have been or are now engaged;
      (ii) have been and are in compliance in all material respects with all applicable federal, state, county and municipal laws, regulations, authorizations, licenses, approvals, permits and orders relating to air, water, soil, solid waste management, hazardous or toxic substances, or the protection of health or the environment (collectively, “Environmental Laws”).
      (b) Except as set forth on Schedule 3.17: (i) there are no claims, actions, suits or proceedings pending or, to the knowledge of the Company, threatened or contemplated against the Company or the Subsidiaries or any assets of the Company or the Subsidiaries, under any of the Environmental Laws (whether by reason of any failure to comply with any of the Environmental Laws or otherwise); (ii) no decree, judgment or order of any kind under any of the Environmental Laws has been entered against the Company or the Subsidiaries; (iii) neither the Company nor the Subsidiaries, during the period in which the Company or the Subsidiaries was or remains the owner, operator, lessor, sublessor or lessee of the real property or facilities described below or, to the knowledge of the Company, during any such prior period: (1) is or was a generator or transporter of hazardous waste, or the owner, operator, lessor, sublessor or lessee of a treatment, storage, or disposal facility or underground storage tank as those terms are defined under the Resource Conservation and Recovery Act, as amended, or regulations promulgated thereunder, or of real property on which such a treatment, storage or disposal facility or underground storage tank is or was located; or A-12 (2) owns, operates, leases or subleases, or owned, operated, leased or subleased (A) any facility at which any Hazardous Substances (as defined below) were treated, stored, recycled, disposed or are or were installed or incorporated, or (B) any real property on which such a facility is or was located; (iv) neither the Company nor the Subsidiaries arranged for the disposal or treatment, arranged with a transporter for transport for disposal or treatment of Hazardous Substances at any facility from which there is a release or threat of release, or accepts or accepted Hazardous Substances for transport for disposal or treatment at any facility, as those terms are defined under the Comprehensive Environmental Response, Compensation and Liability Act, as amended ("CERCLA"); and (v) neither the Company nor the Subsidiaries is or was the holder of a security interest where the party giving the security is or was the owner or operator of a treatment, storage or disposal facility, underground storage tank or any facility at which any Hazardous Substances are or were treated, stored, recycled or disposed and where either the Company or the Subsidiaries participates or participated in management decisions concerning the facility's
      (i) there are no claims, actions, suits or proceedings pending or, to the knowledge of the Company, threatened or contemplated against, or involving, the Company or the Bank, any assets of the Company or the Bank, under any of the Environmental Laws (whether by reason of any failure to comply with any of the Environmental Laws or otherwise);
      (ii) no decree, judgment or order of any kind under any of the Environmental Laws has been entered against the Company or the Bank;
      (iii) neither the Company nor the Bank:
      (1) is or was a generator or transporter of hazardous waste, or the owner, operator, lessor, sublessor, lessee or, to its knowledge, mortgagee of a treatment, storage, or disposal facility or underground storage tank as those terms are defined under the Resource Conservation and Recovery Act, as amended, or regulations promulgated thereunder, or of real property on which such a treatment, storage or disposal facility or underground storage tank is or was located;
      (2) owns, operates, leases, subleases or, to its knowledge, holds a security interest in, or owned, operated, leased or subleased (A) any facility at which any Hazardous Substances (as defined below) were treated, stored in significant quantities, recycled, disposed or are or were installed or incorporated or (B) any real property on which such a facility is or was located;

A-14


      (3) arranged for the disposal or treatment, arranged with a transporter for transport for disposal or treatment of Hazardous Substances at any facility from which there is a release or threat of release, or accepts or accepted Hazardous Substances for transport for disposal or treatment at any facility, as those terms are defined under the Comprehensive Environmental Response, Compensation and Liability Act, as amended (“CERCLA”); or
      (4) is or was the holder of a security interest where the party giving the security is or was the owner or operator of a treatment, storage or disposal facility, underground storage tank or any facility at which any Hazardous Substances are or were treated, stored in significant quantities, recycled or disposed and where either the Company or the Bank participates or participated in management decisions concerning the facility’s waste disposal activities.
      (c) To the Company'sCompany’s knowledge, there are no other facts, conditions or situations, whether now or heretofore existing, that would likelycould form the basis for any claim against, or result in any liability of, the Company or the SubsidiariesBank under any of the Environmental Laws.
      (d) For purposes of this Section 3.18, "Hazardous Substance"3.17, “Hazardous Substance shall mean a hazardous substance (as defined in CERCLA) and petroleum, including crude oil or any fraction thereof, but excluding underground crude oil in its natural unrefined state, prior to its initial extraction.
      3.18     Community Reinvestment Act Compliance. Neither the Company nor the Bank has received any notice of non-compliance with the applicable provisions of the Community Reinvestment Act ("CRA"(“CRA) and the regulations promulgated thereunder, and the Bank has received a CRA rating of satisfactory or better from the Federal Deposit Insurance Corporation (the "FDIC")FDIC or other applicable Governmental Authority. The Company knows of no facts or circumstances which would cause either the Company or the Bank to fail to comply with such provisions or cause the CRA rating of the Bank to fall belowreceive a rating less than satisfactory.
      3.19     Company Regulatory Reports. Since January 1, 2001,2003, the Company and the SubsidiariesBank have each timely filed all reports, registrations and statements, together with any amendments required to be made with respect thereto, required to be filed (i) with the Federal Reserve, the FDIC and the WDFI, and (ii) with any other Governmental Authority or self-regulatory organization with jurisdiction over any of the activities of the Company or the Subsidiaries (other than filings with such other Governmental Authorities or self-regulating organizations which individually or in the aggregate are not material to the business of the Bank (the “Company or the Subsidiaries taken as a whole) (collectively, the "Company Regulatory Reports"Reports), and have paid all fees and assessments due and payable in connection therewith. As of their respective dates, the Company Regulatory Reports complied in all material respects with the statutes, rules and regulations enforced or promulgated by the applicable regulatory authority with which they were filed and did not contain any untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary to make the statement therein, in light of the circumstances under which they were made, not misleading.
      3.20     Employee Benefit Plans.
      (a) The Schedule of Material Contracts, attached as Schedule 3.10, includes a complete and correct list of each employee benefit plan within the meaning of Section 3(3) of ERISA (the "ERISA Plans"ERISA Plans), each compensation, consulting, employment or collective bargaining agreement, and each stock option, stock purchase, stock appreciation right, life, health, disability or other insurance or benefit, bonus, deferred or incentive compensation, severance or separation, profit sharing, retirement, or other employee benefit plan, practice, policy or arrangement of any kind, oral or written, covering employees or former employees of the Company or the SubsidiariesBank which the Company or the SubsidiariesBank maintains or contributes to (or, with respect to any employee pension benefit plan (as defined in Section 3(2) of ERISA) has maintained or contributed to since the date of its incorporation) or to which the Company or the SubsidiariesBank is a party or by which it is otherwise bound (collectively, together with the ERISA Plans, the "Benefit Plans"Benefit Plans). None of the Benefit Plans is a "defined“defined benefit plan"plan” (as defined in Section 414(j) of the Code). Neither the Company nor the SubsidiariesBank has, norand has ever had, an A-13 affiliate that would be treated as a single employer together with the Company or the SubsidiariesBank (an "ERISA Affiliate"ERISA Affiliate) under Section 414 of the Code. (b) OtherCode other than the Company Stock Option Plan and except as set forth on Schedule 3.20(b), none of the Company and the SubsidiariesBank with respect to each other and the subsidiaries identified on Schedule 3.1(b).

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      (b) Except as set forth in Schedule 3.20(b), neither the Company nor the Bank has entered into or maintained any Benefit Plan which includes any change of control provisions which would cause an increase or acceleration of benefits or benefit entitlements to employees or former employees of the Company or the SubsidiariesBank or any other increase in the liabilities of the Company or the SubsidiariesBank under such Benefit Plan as a result of the transactions contemplated by this Agreement.
      (c) None ofNeither the Company andnor the SubsidiariesBank maintains or participates, norand has it ever maintained or participated, in a multiemployer plan within the meaning of Section 3(37) of ERISA. None of the Company, the Subsidiaries,Bank, any director or employee of the Company or the Subsidiaries,Bank, or any fiduciary of any ERISA Plan has engaged in any transaction in violation of Section 406 or 407 of ERISA or, to the Company’s knowledge, any "prohibited transaction"“prohibited transaction” (as defined in Section 4975(c)(1) of the Code) for which no exemption exists under Section 408(b) of ERISA or Section 4975(d) of the Code in connection with such ERISA Plan. None ofExcept as set forth in Schedule 3.20(c), neither the Company andnor the SubsidiariesBank provides nor has ever provided medical benefits to former employees, except as required by Section 601 of ERISA.
      (d) Except as set forth on Schedule 3.20(d), eachEach ERISA Plan that is intended to qualify under Section 401 and related provisions of the Code is the subject of a favorable determination letter from the Internal Revenue Service ("IRS"(“IRS), or satisfies the provisions of IRS Announcement 2001-77, Section II, if applicable, to the effect that it is so qualified under the Code and that its related funding instrument is tax exempt under Section 501 of the Code. Nothing has occurred since the date of such determination letter that would adversely affect such determination or the qualified tax exempt status of such ERISA Plan and its related funding instrument since their establishment.instrument.
      (e) EachExcept as set forth on Schedule 3.20(e), each Benefit Plan is, and since its inception, has been administered in material compliance with its terms and with all applicable laws, rules and regulations governing such Benefit Plan, including the rules and regulations promulgated by the Department of Labor, the Pension Benefit Guaranty Corporation and the IRS under ERISA, the Code or any other applicable law. Neither the Company nor any affiliate of the Company that is a fiduciary with respect to any Benefit Plan, has breached any of the responsibilities, obligations or duties imposed on it by ERISA. No Benefit Plan is currently the subject of a submission under the IRS Employee Plans Compliance Resolution System or any similar system, nor under any Department of Labor amnesty program, and neither the Company nor any of the Subsidiaries anticipateBank anticipates any such submission of any Benefit Plan.
      (f) There is no litigation, claim or assessment pending or, to the Company'sCompany’s knowledge, threatened by, on behalf of, or against any of the Benefit Plans or against the administrators or trustees or other fiduciaries of any of the Benefit Plans that alleges a violation of applicable state or federal law. To the Company'sCompany’s knowledge, there is no reasonable basis for any such litigation, claim or assessment.
      (g) No Benefit Plan fiduciary or any other person has, or has had, to the Company's knowledge, any liability to any Benefit Plan participant, beneficiary or any other person under any provisions of ERISA or any other applicable law by reason of any action or failure to act in connection with any Benefit Plan, including, but not limited to, any liability by any reason of any payment of, or failure to pay, benefits or any other amounts or by reason of any credit or failure to give credit for any benefits or rights. Every Benefit Plan fiduciary and official is bonded to the extent required by Section 412 of ERISA.
      (h) All accrued contributions and other payments to be made by the Company or the SubsidiariesBank to any Benefit Plan through the date hereof have been made or reserves adequate for such purposes have been set aside therefor and reflected in the Financial Statements. None ofNeither the Company andnor the SubsidiariesBank is in default in performing any of its contractual obligations under any of the Benefit Plans or any related trust agreement or insurance contract. There are no outstanding liabilities with respect to any Benefit Plan other than liabilities for benefits to be paid to participants in such Benefit Plan and their beneficiaries in accordance with the terms of such Benefit Plan. A-14
      (i) No Benefit Plan provides for payment of any amount which, considered in the aggregate with amounts payable pursuant to all other Benefit Plans, would exceed the amount deductible for federal income tax purposes by virtue of Section 280G or 162(m) of the Code.

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      (j) ThereTo the extent the Company or the Bank participates in any “multiple employer welfare arrangements” as defined under Section 3(40) of ERISA, the Company is not delinquent in any contribution that it is obligated to make towards the funding of any such arrangement, and to the knowledge of the Company, such arrangement has been administered in material compliance with its terms and with all applicable state and federal laws, rules and regulations governing such arrangement, including, without limitation, ERISA and the rules and regulations thereunder, and the Company may withdraw from such arrangement at any time without penalty or any further obligation other than required notices, the payment of premiums that become payable prior to the date as of which the trustee shall have procured the exclusion of the Company’s insured employees and beneficiaries from the coverage of the applicable insurance policies, and applicable indemnification obligations of the arrangement, provided such obligations are not material.
      (k) Except as provided on Schedule 3.20(c), there are no obligations or liabilities, whether outstanding or subject to future vesting, for any post-retirement benefits to be paid to participants under any of the Benefit Plans.
      3.21     Technology and Intellectual Property.
      (a) Attached as Schedule 3.21 is a Schedule of Intellectual Property, which sets forth a complete and correct list of all (i) registered trademarks, service marks, copyrights and patents; (ii) applications for registration or grant of any of the foregoing; (iii) unregistered trademarks, service marks, trade names, logos and assumed names; and (iv) licenses for any of the foregoing, in each case, owned by the Company or the SubsidiariesBank or used in or necessary to conduct the Company'sCompany’s or the Subsidiaries'Bank’s business as presently conducted. The items on Schedule 3.21, together with all other trademarks, service marks, trade names, logos, assumed names, patents, copyrights, trade secrets, computer software, licenses, formulae, customer lists or other databases, business application designs and inventions currently used in or necessary to conduct the business of the Company and the Subsidiaries as presently conducted constitute the "Intellectual Property."Intellectual Property.”
      (b) Except as set forth on Schedule 3.21, the Company or the SubsidiariesBank has ownership of, or such other rights by license, lease or other agreement in and to, the Intellectual Property as is necessary to permit the Company and the SubsidiariesBank to use the Intellectual Property in the conduct of their respective businesses as presently conducted. None ofNeither the Company andnor the SubsidiariesBank has received notice (whether written or, to the knowledge of the Company, oral) alleging that the Company or the SubsidiariesBank has infringed or violated any trademark, trade name, copyright, patent, trade secret right or other proprietary right of others, and to the Company'sCompany’s knowledge, it has not committed any such violation or infringement. Other than as set forth on Schedule 3.21, to the Company'sCompany’s knowledge, there is no reason to believe that, upon consummation of the transactions contemplated hereby, the Company or the SubsidiariesBank will be in any way more restricted in its use of any of the Intellectual Property than it was on the date hereof under any contract to which the Company or the SubsidiariesBank is a party or by which it is bound, or that use of such Intellectual Property by the Company or the SubsidiariesBank will, as a result of such consummation, violate or infringe the rights of any person, or subject Wintrust, the Company or the SubsidiariesBank to liability of any kind, under any such contract.
      (c) The IT Assets operate and perform in all material respects in accordance with their documentation and functional specifications and otherwise as required by the Company and the SubsidiariesBank in connection with their respective businesses, and have not materially malfunctioned or failed within the past three (3) years. "IT Assets"IT Assets means the computers, computer software, firmware, servers, workstations, routers, hubs, switches, data communications lines and all other information technology equipment, and all associated documentation, owned or leased by the Company or the Subsidiaries.Bank. To the knowledge of the Company or the Bank, the IT Assets do not contain any worms, viruses, bugs, faults or other devices or effects that (i) enable or assist any person or entity to access without authorization the IT Assets, or (ii) otherwise significantly adversely affect the functionality of the IT Assets, except as disclosed in its documentation. To the knowledge of the Company, no person or entity has gained unauthorized access to the IT Assets. The Company and the SubsidiariesBank have implemented reasonableback-up and disaster recovery technology consistent with industry practices. To the knowledge of the Company and except for “off the shelf” software licensed by the Company or the Bank in the Ordinary Course of Business, none of the IT

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Assets contains any shareware, open source code, or other software the use of which requires disclosure or licensing of any intellectual property.
      3.22     No Adverse Change. Other than as specifically disclosed in this Agreement, the Financial Statements, or the Schedules delivered pursuant to this Agreement, there has not occurred (a) since December 31, 20032004 any Material Adverse Effect on the Company and its Subsidiaries, taken as a whole,or the Bank, or (b) any changechanges or condition, event, circumstance, fact or other occurrence, whether occurring before or since December 31, 2003,2004 that may reasonably be expected to have or result in a Material Adverse Effect on the Company and its Subsidiaries, taken as a whole.or the Bank. No fact or condition exists with respect to the business, operations or assets of the Company or the SubsidiariesBank which the Company has reason to believe may cause the Federal Reserve Application, the IDFPR Application or any of the other regulatory approvals referenced in Section 7.3 or 8.3 to be denied or unduly delayed. A-15
      3.23     Conduct of Business in OrdinaryNormal Course. Except as set forth on Schedule 3.23 and for actions taken in connection with negotiating the process that culminated withsale of the Company and entering into this Agreement, since December 31, 2003,2004 the businesses of each of the Company and the SubsidiariesBank have been conducted only in the Ordinary Course of Business.
      3.24     Change in Business Relationships. As of the date of this Agreement, none of Neither the Company andnor the SubsidiariesBank has received notice (whether written or, to the knowledge of the Company, oral), whether on account of the transactions contemplated by this Agreement or otherwise, (a) that any customer, agent, representative, supplier, vendor or business referral source of the Company or the SubsidiariesBank intends to discontinue, diminish or change its relationship with the Company or the Subsidiaries,Bank, the effect of which would be material to the business ofCompany or the Company and the Subsidiaries taken as a whole,Bank, or (b) that any executive officer of the Company or the SubsidiariesBank intends to terminate or substantially alter the terms of his or her employment. There have been no complaints or disputes (in each case set forth in writing) with any customer, employee, agent, representative, supplier, vendor, business referral source or vendor of the Company or the Subsidiariesother parties that have not been resolved which are reasonably likely to be material to the Company.Company or the Bank.
      3.25     Brokers'Brokers’ and Finders'Finders’ Fees. Except as disclosed onset forth in Schedule 3.25, neither the Company nor any of the SubsidiariesBank has incurred any liability for brokerage commissions, finders'finders’ fees, or like compensation with respect to the transactions contemplated by this Agreement.
      3.26     Section 280G Payments. Except as set forth on Schedule 3.26, neither the execution of this Agreement nor the consummation of the transactions contemplated hereby will result in any payment that would be deemed an “excess parachute payment” under Section 280G of the Code.
      3.27     No Omissions. None of the representations and warranties contained in Article III, in the Schedules provided for herein by the Company or in the Financial Statements is false or misleading in any material respect or omits to state a fact herein or therein necessary to make such statements not misleading in any material respect. 3.27 Section 280G Payments. Neither the execution of this agreement nor the consummation of the transactions contemplated hereby (including, without limitation, such transactions as are embodied in ancillary agreements the forms of which are attached as exhibits hereto) will result in any payment that would be deemed an "excess parachute payment" under Section 280G of the Code.
ARTICLE 4 IV
REPRESENTATIONS AND WARRANTIES
CONCERNING WINTRUST
      Wintrust hereby represents and warrants to the Company as follows:
      4.1     Organization. Wintrust is duly registered as a financial holding company under the BHCA, is a corporation duly organized, validly existing and in good standing under the laws of the State of Illinois, has the corporate power and authority to own its own properties and to carry on its business as it is now being conducted, and is duly qualified and in good standing as a foreign corporation in each jurisdiction where the location and character of its properties and the business conducted by it require such qualification, except where the failure to be so qualified would not have a Material Adverse Effect on Wintrust.Effect.
      4.2     Capitalization. The authorized capital stock of Wintrust consists of (i) 30,000,00060,000,000 shares of common stock, no par value per share, of which 20,470,27723,654,783 shares were issued and outstanding as of May 31, 2004,

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September 30, 2005, (ii) 20,000,000 shares of preferred stock, no par value per share, of which 100,000 shares are designated Junior Serial Preferred Stock A, no par value per share, and no shares of preferred stock are issued and outstanding, and (iii) no shares are held in treasury. As of May 31, 2004September 30, 2005 there were (i) outstanding options in respect of 3,045,3153,440,528 shares of Wintrust Common Stock and (ii) outstanding warrants for the purchase of 177,765110,045 shares of Wintrust Common Stock, and (iii) preferred share purchase rights outstanding pursuant to the Rights Agreement between Wintrust and Illinois Stock Transfer Company, as Rights Agent, dated July 28, 1998.Stock. Such options warrants and rightswarrants have been duly authorized by all necessary corporate action (including shareholder approval, if necessary). Such options and warrants have been validly executed, issued and delivered by Wintrust, and constitute the legal, valid and binding obligations of Wintrust, and are enforceable as to Wintrust in accordance with their terms. The shares of Wintrust Common Stock to be issued upon exercise of such options and warrants are validly authorized and, upon such exercise in accordance with their terms, will be validly issued, fully paid, and nonassessable. The issued and outstanding shares of Wintrust Common Stock have been duly and validly authorized and issued and are fully paid and nonassessable. Wintrust Common Stock is subject to certain preferences, qualifications, limitations, restrictions or special or relative rights under Wintrust'sWintrust’s articles of A-16 incorporation, a true and complete copy of which has been previously provided to the Company. Except for such options and warrants, and preferred share purchase rights, there are no options, agreements, contracts or other rights in existence to purchase or acquire from Wintrust any shares of capital stock of Wintrust, whether now or hereafter authorized or issued, other than shares issuable pursuant to employee benefit or compensation plans referred to in the Wintrust SEC Documents. Wintrust has reserved, and at the Effective Time will have, a number of authorized but unissued shares of Wintrust Common Stock sufficient for that amount required for the Conversion Fund under Section 2.1. The shares of Wintrust Common Stock to be issued pursuant to the Merger, when so issued in accordance with this Agreement, will be duly and validly authorized and issued, and fully-paid and nonassessable.
      4.3     Authorization; No Violations. The execution and delivery of this Agreement and the performance of Wintrust'sWintrust’s obligations hereunder have been duly and validly authorized by the Board of Directors of Wintrust, do not violate or conflict with its articles of incorporation or by-laws, the Illinois Act, or any applicable law, court order or decree to which Wintrust or any of its subsidiaries is a party or subject, or by which Wintrust or any of its subsidiaries or any of their respective properties is bound, and require no further corporate or shareholder approval on the part of Wintrust. The execution and delivery of this Agreement and the performance of Wintrust'sWintrust’s obligations hereunder do not and will not result in any default or give rise to any right of termination, cancellation or acceleration under any material note, bond, mortgage, indenture or other agreement by which Wintrust is bound. This Agreement, when executed and delivered, and subject to the regulatory approval described in Section 4.4, will be a valid, binding and enforceable obligation of Wintrust, subject to applicable bankruptcy, insolvency, reorganization, moratorium or similar laws affecting creditors generally and to general principles of equity.
      4.4     Consents and Approvals. No consents or approvals of, or filings or registrations with, any Governmental Authority or with any third party are necessary in connection with the execution and delivery by Wintrust of this Agreement and the consummation by Wintrust, as of the Effective Date, of the Merger except for (a) the filing by Wintrust of the Federal Reserve Application withand the Federal Reserve under the BHCA,IDFPR Application, (b) the filing of the WDFI Application with the Division of Banking of the WDFI, (c) the filing with the Commission of the Registration Statement (as defined in Section 5.4(a)), and (d)(c) the filing of the Articles of Merger with the Illinois Secretary of State under Section 11.25 of the State of Illinois under the Illinois Act and with the WDFI under the Wisconsin Act.
      4.5     Wintrust SEC DocumentsFilings and Financial Statements.
      (a) Since January 1, 2001,2003, Wintrust has timely filed all reports, registration statements and other documents (including any amendments thereto) required to be filed with the Commission under the Securities Act, the Securities Exchange Act of 1934, as amended (the "Exchange Act"Exchange Act), the Securities Act and the rules and regulations of the Commission (the "WintrustWintrust SEC Documents"Documents), and all such Wintrust SEC Documents have complied in all material respects, as of their respective filing dates and effective dates, as the case may be, with all applicable requirements of the ExchangeSecurities Act andor the SecuritiesExchange Act. As of their respective filing and effective dates, none of the Wintrust SEC Documents contained an untrue statement of a material fact or omitted to state a material fact required to be stated therein or necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading.
      (b) The audited consolidated financial statements contained or incorporated by reference in Wintrust'sWintrust’s Annual Report onForm 10-K for the years ended December 31, 2001, 20022003 and 20032004 and the unaudited interim financial statements included in Wintrust'sWintrust’s most recent Quarterly Report onForm 10-Q have been prepared in conformity with GAAP applied on a consistent basis, throughout the periods involved, and, together with the notes thereto, present fairly the consolidated financial position of Wintrust and its subsidiaries at the dates shown

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and the consolidated results of their operations, changes in shareholders'shareholders’ equity and cash flows for the periods then ended. The interim financial statements as of, and for, the periods ending after December 31, 20032004 included in Wintrust'sWintrust’s Quarterly Reports onForm 10-Q, as filed with the Commission, include all adjustments necessary for a fair presentation of the financial position of Wintrust and its subsidiaries and the results of their operations for the interim periods presented, subject to normal, recurring year-end adjustments (which adjustments will not be, individually or in the aggregate, material) and the omission of footnote disclosure.
      (c) The reserves for loan losses shown on each of the balance sheets contained in the Wintrust SEC Documents are adequate in the judgment of management and consistent with the standards of the FDIC and GAAP to provide for losses, net of recoveries relating to loans previously charged off, on loans outstanding (including accrued interest receivable) as of the applicable date of such balance sheet.
      4.6     Compliance with Laws; Legal Proceedings.
      (a) Wintrust and its subsidiaries are each in compliance in all material respects with all applicable federal, state, county and municipal laws and regulations (i) that regulate or are concerned in any way A-17 with the ownership and operation of banks or the business of banking or of acting as a fiduciary, including those laws and regulations relating to the investment of funds, the taking of deposits, the lending of money, the collection of interest, the extension of credit and the location and operation of banking facilities, or (ii) that otherwise relate to or affect the business or assets of Wintrust or any of its subsidiaries or the assets owned, used, occupied or managed by Wintrust or any of its subsidiaries, including, without limitation, all applicable fair lending laws and other laws relating to discriminatory business practices, escrow administration, usury, due on sale and loan servicing, the USA Patriot Act of 2001, the Gramm-Leach-Bliley Act of 1999, the International Money Laundering Abatement and Anti-Terrorist Financing Act of 2001, the Fair Credit Reporting Act, the Home Mortgage Disclosure Act of 1975, the Real Estate Settlement Procedures Act of 1974, the Truth in Lending Act, the Homeowners Protection Act of 1998, the Equal Credit Opportunity Act and the Flood Disaster Protection Act of 1973, in each case as in effect and applicable to Wintrust and its subsidiaries and their operations, except for such noncompliance which individually or in the aggregate would not have a Material Adverse Effect on Wintrust. Wintrust and its subsidiaries (direct and indirect) hold all material licenses, certificates, permits, franchises and rights from all appropriate federal, state or other Governmental Authorities necessary for the conduct of its businesstheir respective businesses and the ownership of itstheir respective assets.
      (b) Except as may be disclosed in the Wintrust SEC Documents, there are no material claims, actions, suits or proceedings pending or, to the knowledge of Wintrust, threatened or contemplated against or affecting Wintrust or its subsidiaries, or any of their respective institution-affiliated parties, at law or in equity, or before any federal, state or other Governmental Authority or any arbitrator or arbitration panel, whether by contract or otherwise, including any claims, actions, suits or proceedings that might seek to challenge the validity or propriety of the Merger, and there is no decree, judgment or order or supervisory agreement of any kind in existence against or restraining Wintrust or its subsidiaries or their respective institution-affiliated parties from taking any action of any kind in connection with their respective businesses. Except as may be disclosed in the Wintrust SEC Documents, none of Wintrust or its subsidiaries has received from any federal, state or other Governmental Authority any notice or threat (whether written or, to the knowledge of Wintrust, oral) of any enforcement action, criticism or recommendation concerning capital, compliance with laws or regulations, safety or soundness, fiduciary duties or other banking or business practices that has not been resolved to the reasonable satisfaction of such Governmental Authority and that would be materially adverse to Wintrust and its subsidiaries taken as a whole, and Wintrust has no reasonable basis to believe that any such enforcement action, criticism or recommendation not otherwise disclosed herein is contemplated.
4.7     Wintrust Regulatory Reports. Since January 1, 2003, Wintrust and its subsidiaries have each timely filed all reports, registrations and statements, together with any amendments required to be made with respect thereto, required to be filed (i) with the Federal Reserve, and the Office of the Comptroller of the Currency (the “OCC”) and (ii) with any other Governmental Authority or self-regulatory organization with jurisdiction over any of the activities of Wintrust or its subsidiaries (other than filings with such other Governmental Authorities or self-regulating organizations which individually or in the aggregate are not material to the business of (the “Wintrust and its subsidiaries taken as a whole) (collectively, the "Wintrust Regulatory Reports"Reports), and have paid all fees and assessments due and payable in connection therewith. As of their respective dates, the Wintrust Regulatory Reports complied in all material respects with the statutes, rules and regulations enforced or promulgated by the applicable regulatory authority with which they were filed and did not contain any untrue statement of a material fact or omit to state a material fact required to be stated therein or necessary to make the statementstatements therein, in light of the circumstances under which they were made, not misleading.
      4.8     No Adverse Change. Except as disclosed in the Wintrust SEC Documents, this Agreement, or the Schedules delivered pursuant to this Agreement there has not occurred (a) since December 31, 2003, 2004,

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any Material Adverse Effect on Wintrust, or (b) any change, or condition, event, circumstance, fact or other occurrence, whether occurring before or since December 31, 2003,2004 that may reasonably be expected to have or result in a Material Adverse Effect on Wintrust. No fact or condition exists with respect to the business, operations or assets of Wintrust or its subsidiaries which Wintrust has reason to believe may cause the Federal Reserve Application, the IDFPR Application or any of the other regulatory approvals referenced in Section 7.3 or 8.3 to be denied or unduly delayed.
      4.9     Brokers'Brokers’ and Finders'Finders’ Fees. Wintrust has not incurred any liability for brokerage commissions, finders'finders’ fees, or like compensation with respect to the transactions contemplated by this Agreement.
      4.10     Taxation of the Merger. Neither Wintrust nor any subsidiary of Wintrust has engaged intaken any actaction or agreed to take any action that would preclude or adversely affect the Merger from qualifying as a tax-free reorganization under Section 368(a) of the Code.Code and, to the knowledge of Wintrust, there are no agreements or arrangements to which Wintrust or any subsidiary of Wintrust is a party that would prevent the Merger from so qualifying.
      4.11     Financial Ability. On the Effective Date, Wintrust will have all funds necessary to consummate the Merger and pay the aggregate Cash Consideration payable hereunder.
      4.12     No Omissions. None of the representations and warranties contained in Article IV or in the Schedules provided for herein is false or misleading in any material respect or omits to state a fact herein necessary to make such statements not misleading in any material respect. A-18
ARTICLE 5 V
AGREEMENTS AND COVENANTS
      5.1     Conduct of Business. During the period commencing on the date hereof and continuing until the Effective Time, except as otherwise expressly permitted or required by this Agreement, the Company shall conduct the Company'sCompany’s business and shall cause the SubsidiariesBank to conduct their respective businessesits business in the Ordinary Course of Business consistent with prudent banking practices.practice. Without limiting the foregoing, except as set forth on Schedule 5.1 or as otherwise expressly permitted or required by this Agreement, without the prior written consent of Wintrust, which consent shall not be unreasonably withheld, conditioned or delayed: (a) no change shall be made in the articles of incorporation or by-laws of the Company or TIC, the charter or by-laws of the Bank, or the organizational documents of the Trust; (b) except with respect to the exercise of any Outstanding Company Option, no change shall be made in the capitalization of the Company (including the granting of any additional options under the Company Option Plan) or the Subsidiaries or in the number of issued and outstanding Company Common Shares; (c) the compensation of officers or key employees of the Company or the Subsidiaries shall not be increased, nor any bonuses paid, except for any such increases or payments not exceeding $10,000 in the aggregate to any individual officer or employee; (d) no Loans, or renewals or restructurings of Loans, in the amount of $1,000,000 or more (including Loans to any one borrower or related group of borrowers which, in the aggregate, equal or exceed $1,000,000) shall be made by the Bank except in the Ordinary Course of Business and consistent with prudent banking practices and the Bank's current loan policies and applicable rules and regulations of applicable Governmental Authorities with respect to amount, term, security and quality of such borrower's or borrowers' credit; (e) no dividends or other distributions shall be declared or paid by the Company, except in connection with the ESOP Share Redemption as described in Section 6.2; (f) the Company and the Subsidiaries shall each use their commercially reasonable efforts to maintain their present insurance coverage in respect to its properties and business; (g) no significant changes shall be made in the general nature of the business conducted by the Company or the Subsidiaries; (h) no employment, consulting or similar agreements shall be entered into by the Company or the Subsidiaries that are not terminable by the Company or such Subsidiary on 30 days' or fewer notice without penalty or obligation; (i) none of the Company and the Subsidiaries shall take any action that would result in a termination, partial termination, curtailment, discontinuance of a Benefit Plan or merger of any Benefit Plan into another plan or trust; (j) the Company and the Subsidiaries shall file all Returns in a timely manner and shall not make any application for or consent to any extension of time for filing any Return or any extension of the period of limitations applicable thereto; (k) except with respect to the build-out of the Bank's Madison branch, none of the Company and the Subsidiaries shall make any expenditure for fixed assets in excess of $25,000 for any single item, or $100,000 in the aggregate, or shall enter into leases of fixed assets having an annual rental in excess of $25,000; (l) none of the Company and the Subsidiaries shall incur any liabilities or obligations, make any commitments or disbursements, acquire or dispose of any property or asset, make any contract or agreement, or engage in any transaction except in the Ordinary Course of Business consistent with prudent banking practices and the Bank's current policies; A-19 (m) none of the Company and the Subsidiaries shall do or fail to do anything that will cause a breach by the Company or the Subsidiaries of, or default by the Company or the Subsidiaries under, any Material Contract; (n) the Bank shall not engage or agree to engage in any "covered transaction" within the meaning of Sections 23A or 23B of the Federal Reserve Act (without regard to the applicability of any exemptions contained in Section 23A) or any transaction of the kind referred to in Section 3.12, unless the Bank has complied with all requirements of Sections 23A or 23B of the Federal Reserve Act; (o) the Bank shall only purchase or invest in obligations of the government of the United States or agencies of the United States or state or local governments having maturities of not more than five years and which municipal obligations have been assigned a rating of A or better by Moody's Investors Service or by Standard & Poor's; (p) no changes of a material nature shall be made in any of the Company's or the Subsidiaries' accounting procedures, methods, policies or practices or the manner in which the Company or the Subsidiaries maintain their records; and (q) the Bank shall not accept or renew any brokered deposits to the extent that the total of outstanding brokered deposits at any one time exceeds $60,000,000 in the aggregate.Wintrust:
      (a) no change shall be made in the articles of incorporation or by-laws of the Company or the charter or by-laws of the Bank;
      (b) except with respect to the exercise of any Option, no change shall be made in the capitalization of the Company or the Bank or in the number of issued and outstanding shares of Company Common Stock or Options;
      (c) the compensation of officers or key employees of the Company or the Bank shall not be increased, nor any bonuses paid except in each case as set forth on Schedule 5.1(c);
      (d) no Loan, or renewal or restructuring of a Loan, in the amount of $1,000,000 or more (including Loans to any one borrower or related group of borrowers which, in the aggregate, equal or exceed $1,000,000) shall be made by the Bank except after delivering to Wintrust a complete loan package for such Loan, renewal or restructuring, in a form consistent with the Bank’s policies and practice, and obtaining Wintrust’s prior consent, which consent shall not be unreasonably withheld or delayed and shall be deemed given if Wintrust shall have not responded to the Company’s request within two (2) business days after receipt of such complete loan package, and such Loan or renewal or restructuring of a Loan shall be made in the Ordinary Course of Business consistent with prudent banking practices, the Bank’s current loan policies and applicable rules and regulations of applicable Governmental Authorities with respect to amount, term, security and quality of such borrower’s or borrowers’ credit;
      (e) no dividends or other distributions shall be declared or paid by the Company to the extent it would cause the shareholders’ equity in the Company, as adjusted pursuant to Section 7.11 below, to fall below the Minimum Adjusted Net Worth, or as otherwise would not be permitted under applicable law;

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      (f) no dividends or other distributions shall be declared or paid by the Bank to the extent it would cause the minimum net worth of the Bank to fall below well-capitalized status, as defined by applicable FDIC regulations, or as would not be permitted under applicable law;
      (g) the Company and the Bank shall each use their commercially reasonable efforts to maintain their present insurance coverage in respect to its properties and business;
      (h) no significant changes shall be made in the general nature of the business conducted by the Company or the Bank;
      (i) no employment, consulting or similar agreements shall be entered into by the Company or the Bank that are not terminable by the Company or the Bank on 30 days’ or fewer notice without penalty or obligation, nor shall the Bank terminate the employment of any officer without first notifying Wintrust;
      (j) except as expressly provided in this Agreement, neither the Company nor the Bank shall take any action that would result in a termination, partial termination, curtailment, discontinuance of a Benefit Plan or merger of any Benefit Plan into another plan or trust;
      (k) the Company and the Bank shall file all Tax Returns in a timely manner and shall not make any application for or consent to any extension of time for filing any Tax Return or any extension of the period of limitations applicable thereto;
      (l) neither the Company nor the Bank shall make any expenditure for fixed assets in excess of $50,000 for any single item, or $250,000 in the aggregate, or shall enter into leases of fixed assets having an annual rental in excess of $50,000;
      (m) neither the Company nor the Bank shall incur any liabilities or obligations, make any commitments or disbursements, acquire or dispose of any property or asset, make any contract or agreement, or engage in any transaction except in the Ordinary Course of Business consistent with prudent banking practices and the Bank’s current policies;
      (n) neither the Company nor the Bank shall do or fail to do anything that will cause a breach by the Company or the Bank of, or default by the Company or the Bank under, any Material Contract;
      (o) the Bank shall not engage or agree to engage in any “covered transaction” within the meaning of Sections 23A or 23B of the Federal Reserve Act (without regard to the applicability of any exemptions contained in Section 23A) or any transaction of the kind referred to in Section 3.12, unless the Bank has complied with Sections 23A and B of the Federal Reserve Act;
      (p) the Bank shall only purchase or invest in obligations of the government of the United States or agencies of the United States or state or local governments having maturities of not more than five (5) years and which municipal obligations have been assigned a rating of A or better by Moody’s Investors Service or by Standard and Poor’s, which may include purchases by the Bank in the open market of direct debt obligations of the Federal Home Loan Bank of Chicago,provided that such direct debt obligations do not exceed an aggregate amount of $10,000,000 and are not purchased by the Bank at a premium;
      (q) the amount of brokered deposits maintained by the Bank at any time and from time to time shall not exceed $65,000,000; and
      (r) no changes of a material nature shall be made in either the Company’s or the Bank’s accounting procedures, methods, policies or practices or the manner in which the Company or the Bank maintain their records.
      5.2     Access to Information.
      (a) To the extent permissible under applicable law and pending the Closing, representatives of Wintrust shall, during normal business hours and on reasonable advance notice to the Company, be given

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full access to the Company'sCompany’s and the Subsidiaries'Bank’s records and business activities and be afforded the opportunity to observe their business activities and consult with their officers and employees regarding the same on an ongoing basis (without limiting the foregoing, to verify compliance by the Company with all terms of this Agreement);provided,however, that the foregoing actions do not interfere with the business operations of the Company orand the Subsidiaries.Bank.
      (b) Wintrust will use such information as is provided to it by the Company or the SubsidiariesBank, or their respective representatives thereof, solely for the purpose of conducting business, legal and financial reviews of the Company and the SubsidiariesBank and for such other purposes as may be related to this Agreement, and Wintrust will, and will direct all of its agents, employees and advisors to, maintain the confidentiality of all such information in accordance with the terms of the letter agreement regarding confidentiality entered into by and between the Company and Wintrust dated November 4, 2003July 29, 2005 (the "Confidentiality Agreement"Confidentiality Agreement). (c) To the extent permissible under applicable law, pending the Closing and solely for the purpose of permitting the Company to ascertain the correctness of the representations and warranties made in this Agreement by Wintrust, representatives of the Company shall, during normal business hours and on reasonable advance notice to Wintrust, be given access to the records and business activities of Wintrust and its subsidiaries and be afforded the opportunity to observe their business activities and consult with their officers and employees regarding the same, provided, however, that in Wintrust's sole reasonable judgment the foregoing actions do not interfere with the business operations of Wintrust or any of its subsidiaries. The Company will, and will direct all of its agents, employees and advisors to, maintain the confidentiality of all such information in accordance with the terms of the Confidentiality Agreement.
      5.3     Meeting of Shareholders of the Company. As soon as practicable after the date of this Agreement and the effectiveness of the Registration Statement pursuant to Section 5.4, the Company shall through the Company Board, subject to its fiduciary duties, call and hold a meeting of its shareholders for the purpose of voting upon this Agreement, the Merger and the transactions herein contemplated in accordance with the Company'sCompany’s articles of incorporation, its by-laws and the WisconsinIllinois Act (the "Shareholders Meeting"Shareholders Meeting). The Company shall, through the Company Board, recommend to its shareholders, subject to its fiduciary duties, approval of this Agreement and the Merger. A-20
      5.4     Registration Statement and Regulatory Filings. As soon as practicable after the execution of this Agreement:
      (a) Wintrust shall file with the Commission within 30 days after the execution of this Agreement or as soon as practicable thereafter, a registration statement on an appropriate form under the Securities Act covering Wintrust Common Stock to be issued pursuant to this Agreement and shall use its reasonable and diligent efforts to cause the same to become effective as soon as practicable and thereafter, until the Effective Time or termination of this Agreement, to keep the same effective and, if necessary, amend and supplement the same. Such registration statement and any amendments and supplements thereto are referred to herein as the "Registration Statement."Registration Statement.” The Registration Statement shall include a Proxy Statement/Prospectus thereto reasonably acceptable to Wintrust and the Company, prepared by Wintrust and the Company for use in connection with the meeting of shareholders of the Company referred to in Section 5.3,Shareholders Meeting, all in accordance with the rules and regulations of the Commission. Wintrust shall, as soon as practicable after the execution of this Agreement, make all filings, if any, required to obtain all blue sky permits, authorizations, consents or approvals required for the issuance of Wintrust Common Stock. In advance of filing the Registration Statement, Wintrust shall provide the Company and its counsel with a copy of the Registration Statement and provide an opportunity to comment thereon, and thereafter shall promptly advise the Company and its counsel of any material communication received by Wintrust or its counsel from the Commission with respect to the Registration Statement. None of the information furnished by Wintrust or the Company for inclusion in the Registration Statement, the Proxy Statement/Prospectus or any other document filed with the Commission or any state securities commission, at the respective times at which such documents are filed with the Commission or such state securities commission, or, in the case of the Registration Statement, when it becomes effective, or in the case of the Proxy Statement/Prospectus, when mailed or at the time of the Shareholders Meeting, shall be false or misleading with respect to any material fact or shall omit to state any material fact necessary in order to make the statements therein, in light of the circumstances in which they were made, not misleading.
      (b) Wintrust, shallwithin 30 days following execution and delivery of this Agreement, will file with the Federal Reserve Application and the Federal ReserveIDFPR Application and take all other appropriate actions (except as otherwise specified in Section 5.4(a) above) necessary to obtain the regulatory approvals referred to in SectionSections 7.3 and 8.3 hereof, and the Company will use all reasonable and diligent efforts to assist in obtaining all such approvals. The obligation to take all appropriate actions shall not be construed as including an obligation to accept any terms of or conditions to a consent, authorization, order, or approval of, or any exemption by, any Governmental Authority or other party that are not acceptable to Wintrust, in its sole reasonable discretion, or to change the business practices of Wintrust or any of its subsidiaries in

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a manner not acceptable to Wintrust, in its sole reasonable discretion. In advance of filing any applications for such regulatory approvals, Wintrust shall provide the Company and its counsel with a copy of such applications (but excluding any information contained therein regarding Wintrust and its business or operations for which confidential treatment has been requested) and provide an opportunity to comment thereon, and thereafter shall promptly advise the Company and its counsel of any material communication received by Wintrust or its counsel from any regulatory authorities with respect to such applications.
      5.5     Listing of Shares. Wintrust shall use all reasonable and diligent efforts to cause the shares of Wintrust Common Stock issuable in the Merger to be approved for listing on the Nasdaq National Market.
      5.6     Reasonable and Diligent Efforts. The Parties shall use reasonable and diligent efforts in good faith to satisfy the various conditions to Closing and to consummate the Merger as soon as practicable. None of the Parties will intentionally take or intentionally permit to be taken any action that would be in breach of the terms or provisions of this Agreement (including any action that would impair or impede the timely obtainment of the regulatory approvals referenced in Sections 7.3 and 8.3) or that would cause any of the representations contained herein to be or become untrue.
      5.7     Business Relations and Publicity. The Company shall use reasonable and diligent efforts to preserve the reputation and relationship of the Company and the SubsidiariesBank with suppliers, clients, customers, employees, and others having business relations with the Company or the Subsidiaries.Bank. Wintrust and the Company shall coordinate all publicity relating to the transactions contemplated by this Agreement and, except as otherwise required by applicable law or the rules of the Nasdaq National Market, or with respect to employee meetings, neither Party shall issue any press release, publicity statement or other public notice or communication, whether written or oral, relating to this Agreement or any of the transactions contemplated hereby without obtaining the prior consent of the other, which consent shall not be unreasonably withheld, conditioned or delayed. The Company shall obtain the prior consent (which shall not be unreasonably withheld, conditioned or delayed) of Wintrust to the content of A-21 any communication to itsthe Company’s shareholders. In furtherance of the foregoing the Parties acknowledge that immediately after execution of this Agreement Wintrust shall issue a news release (after consultation with the Company as to its content) and file the same with the Commission onForm 8-K.
      5.8     No Conduct Inconsistent with this Agreement.
      (a) The Company shall not, and shall cause each of the SubsidiariesBank to not, during the term of this Agreement, directly or indirectly, solicit, encourage or facilitate inquiries or proposals or enter into any agreement with respect to, or initiate or participate in any negotiations or discussions with any person or entity concerning, any proposed transaction or series of transactions involving or affecting the Company or the SubsidiariesBank (or their respectivethe securities or assets)assets of either) that, if effected, would constitute an acquisition of control of either the Company or the SubsidiariesBank within the meaning of 12 U.S.C.A. ss.1817(j)§1817(j) (disregarding the exceptions set forth in 12 U.S.C.A. ss.1817(j)§1817(j)(17)) and the regulations of the Federal Reserve thereunder (each, an "Acquisition Proposal"Acquisition Proposal), or furnish any information to any person or entity proposing or seeking an Acquisition Proposal.
      (b) Notwithstanding the foregoing, in the event that the Company Board determines in good faith and after consultation with outside counsel, that in light of a Superioran Acquisition Proposal (as defined herein) other than an Acquisition Proposal the terms of which were made known to the Company Board prior to the date hereof, it is necessary to pursueprovide such Superior Acquisition Proposalinformation or engage in such negotiations or discussions in order to act in a manner consistent with such Board'sBoard’s fiduciary duties, the Company Board may, in response to an Acquisition Proposal which was not solicited by or on behalf of the Company or the Subsidiaries after the date of this AgreementBank or which did not otherwise result from a breach of Section 5.8(a), subject to its compliance with Section 5.8(c), (i) furnish information with respect to the Company or the SubsidiariesBank to such person or entity making such Superior Acquisition Proposal pursuant to a customary confidentiality agreement that is no less restrictive than the Confidentiality Agreement and (ii) participate in discussions or negotiations regarding such Acquisition Proposal. In the event that the Company Board determines in good faith and after consultation with outside counsel, that the Acquisition Proposal is a Superior Acquisition Proposal (iii)(as

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defined below) and that it is necessary to pursue such Superior Acquisition Proposal in order to act in a manner consistent with such Board’s fiduciary duties, the Company may (A) withdraw, modify or otherwise change in a manner adverse to Wintrust, the Company'sCompany’s recommendation to its shareholders with respect to this Agreement and the Merger, and/or (iv)(B) terminate this Agreement in order to concurrently enter into an agreement with respect to such Superior Acquisition Proposal;provided,however, that the Company Board may not terminate this Agreement pursuant to this Section 5.8(b) unless and until (x) five (5) business days have elapsed following the delivery to Wintrust of a written notice of such determination by the Company Board and during such five (5) business daybusiness-day period, the Company and the SubsidiariesBank otherwise cooperate with Wintrust with the intent of enabling the Parties to engage in good faith negotiations so that the Merger and other transactions contemplated hereby may be effected and (y) at the end of such five business day(5) business-day period the Company Board continues in its good faith judgmentcontinue reasonably to believe the Acquisition Proposal at issue constitutes a Superior Acquisition Proposal. A "SuperiorSuperior Acquisition Proposal" meansProposal” shall mean any Acquisition Proposal containing terms which the Company Board determines in its good faith judgment (based on the advice of itsan independent financial advisor) to be more favorable to the Company'sCompany’s shareholders than the Merger and for which financing, to the extent required, is then committed or which, in the good faith judgment of the Company Board, is reasonably capable of being obtained by such third party.party, but shall exclude any Acquisition Proposal the terms of which were made known to the Company Board prior to the date of this Agreement.
      (c) In addition to the obligations of the Company set forth in Section 5.8(a) and (b), the Company shall immediately advise Wintrust orally and in writing of any request for information or of any Acquisition Proposal, the material terms and conditions of such request or Acquisition Proposal and the identity of the person or entity making such request or Acquisition Proposal. The Company shall keep Wintrust reasonably informed of the status and details (including amendments or proposed amendments) of any such request or Acquisition Proposal, including the status of any discussions or negotiations with respect to any Superior Acquisition Proposal.
      5.9Loan Charge-Off; Pre-Closing Loan Review.
      (a) The Company shall cause the Bank, prior to the Closing Date, to write off all Loans of the Bank that are required to be written off by the Bank'sBank’s regulators or that, in conformity with past practices and policies of the Bank and GAAP, should be written off as Loan losses.
      (b) The Company shall make available to Wintrust fullthe files maintained by the Bank with respect to, and information regarding the status of, each Loan contained in the Loan portfolio of the Bank, as of a date not more than 15 days prior to the Closing Date. A-22
      (c) Wintrust and the Company shall negotiate in good faith regarding the write down, in conformity with the provisions of Section 5.9(a) above, of potential Loan losses (net of reasonablereasonably conservative estimates of collateral recoveries and of applicable reserves) identified to the Company by Wintrust;provided,however that, that: (i) the Company shall not be required to take any actions as a result of such good faith negotiations (1) more than five (5) days prior to the Closing Date and (2) until such time as the Company shall have received reasonable assurances that all conditions precedent to Wintrust'sWintrust’s obligations under this Agreement (except for the completion of actions to be taken at the Closing) have been satisfied, and (3) solely with respect to those Loans reviewed by Wintrust and identified on Schedule 5.9(c), unless there shall have occurred since the date of this Agreement a material change in the underlying terms, facts or circumstances relating to any such Loans, andsatisfied; (ii) any such actions taken as a result of such good faith negotiation (1) shall not have any effect on, or result in a breach of, the representations and warranties under Section 3.8 made by the Company and the Bank as of the date of this Agreement.Agreement and (2) shall not result in a Material Adverse Effect on the Company, but shall be taken into account in determining the Minimum Adjusted Net Worth (as defined in Section 7.9 below) of the Company as of the Closing Date; and (iii) nothing in this Section 5.9 shall require the Company to make any additional provision to the Bank’s reserve for loan losses so long as such reserve, determined as described in Section 3.8 and in compliance with the second sentence of Section 5.13 below, is adequate and not less than 1.00% of the Bank’s total Loans (gross Loans less unearned discounts).
      5.10     Board of Directors'Directors’ Notices and Minutes. The Company shall give reasonable notice to Wintrust of all meetings of the Company Board and any of its committees, and thosethe board of eachdirectors of

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the Bank TIC and the Trust, respectively,any of its committees, and if known, the agenda for or business to be discussed at such meetings. To the extent permissible under law, the Company shall promptly transmit to Wintrust copies of all notices, minutes, consents board packages and other materials that the Company or the SubsidiariesBank provides to their directors, as the case may be, other than materials relating to any proposed acquisition of the Company or the Bank, or this Agreement or the Merger, subject to the Company'sCompany’s compliance with Section 5.8. Wintrust agrees to hold in confidence and trust all such information pursuant to the Confidentiality Agreement.
      5.11     Untrue Representations and Warranties. During the term of this Agreement, if any Party becomes aware of any facts, circumstances or of the occurrence or impending occurrence of any event that would cause one or more of such Party'sParty’s representations and warranties contained in this Agreement to be or to become untrue as of the Closing Date then: (a) such Party shall promptly give detailed written notice thereof to the other Parties; and (b) such Party shall use reasonable and diligent efforts to change such facts or events to make such representations and warranties true, unless the same shall have been waived in writing by the other Parties.
      (a) such Party shall promptly give detailed written notice thereof to the other Parties; and
      (b) such Party shall use reasonable and diligent efforts to change such facts or events to make such representations and warranties true, unless the same shall have been waived in writing by the other Party.
      5.12     Director and Officer Indemnification and Liability Coverage. (a) Wintrust agrees to provide each of the directors (or managers) and officers of the Company and each of the SubsidiariesBank after the Effective Time substantially the same insurance coverage against personal liability for actions taken after the Effective Time as is provided to current directors and officers of Wintrust. Wintrust further agrees to cause the Surviving Corporation, or its successor in interest,to the extent permitted by applicable law, to indemnify the current and past directors (or managers) and officers of the Company and eachthe Bank, for a period of five (5) years after the SubsidiariesEffective Time, for all actions taken by them prior to the Effective Time in their respective capacities as directors (or managers) and officers of the Company and the SubsidiariesBank to the same extent as the indemnification provided by the Company and each of the SubsidiariesBank under their respective by-laws to such directors (or managers) and officers immediately prior to the Effective Time. (b) Wintrust agrees that for a period of five (5) years after the Effective Time, Wintrust shall cause to be maintained in effect the Company's and the Subsidiaries' current policy (as in effect on the Closing Date) of directors' and officers' liability insurance maintained by the Company with respect to actions and omissions occurring on or prior to the Effective Time, subject to the following conditions: (i) The Company's and each of the Subsidiaries' current directors' and officers' liability insurer shall agree to maintain such coverage from and after the Effective Time. In the event such insurer terminates or declines to continue such coverage after the Effective Time, Wintrust shall use its commercially reasonable efforts, with the cooperation of the former directors and officers of the Company, to identify and obtain similar coverage from another insurance carrier of substantially similar size and reputation to that of such former insurer, if such coverage is reasonably obtainable from the marketplace. If after such reasonable efforts another such insurance carrier is unable or unwilling to provide such similar coverage, Wintrust shall obtain A-23 the best coverage available, in the sole reasonable judgment of Wintrust, for a cost up to but not exceeding the Maximum Amount (as defined below). (ii) Wintrust may substitute therefor policies of at least the same coverage and amount containing terms and conditions which are substantially no less advantageous, in Wintrust's sole reasonable judgment. (iii) In no event shall Wintrust be obligated to expend, in order to maintain or provide insurance coverage pursuant to this Section 5.12(b), any amount, in aggregate, in excess of $40,000 per annum (the "Maximum Amount"). (iv) Prior to the Effective Time, the Company shall notify the appropriate directors' and officers' liability insurers of the Merger and of all pending or threatened claims, actions, suits, proceedings or investigations asserted or claimed against any officer or director of the Company or the Subsidiaries, or circumstances likely to give rise thereto to the extent known by the Company, in accordance with the terms and conditions of the applicable policies. (v) If the amount of the annual premiums necessary to maintain or procure such insurance coverage exceeds the Maximum Amount, Wintrust shall use reasonable efforts, in its sole reasonable judgment, to maintain the most advantageous policies of directors' and officers' insurance obtainable for an annual premium equal to the Maximum Amount. (vi) The Company and its directors and officers shall use reasonable and diligent efforts to cooperate with Wintrust in obtaining the above-described insurance coverages. (c) The obligations under this Section 5.12 shall not be terminated or modified in such a manner (other than with respect to the exercise of Wintrust's sole reasonable judgment as specified therein) as to adversely affect any person to whom this Section 5.12 applies without the consent of such affected persons, which consent shall not be unreasonably withheld, delayed or conditioned, it being expressly agreed that the persons to whom this Section 5.12 applies shall be third-party beneficiaries of this Section 5.12 and shall be entitled to enforce the covenants contained herein in accordance with their terms.
      5.13     MonthlyInterim Financial Statements. Prior to the Closing Date, the Company shall deliver to Wintrust (a) a monthly balance sheet, income statement and statement of shareholders'shareholders’ equity of the Company and each of the Subsidiaries as of the end of each calendar quarter as promptly as practicable after they become available and (b) a monthly balance sheet and income statement of the Bank as of the end of each month as promptly as practicable after they become available. Such monthly financial statements shall be prepared (x) consistent with past practice (to the extent applicable) and (y) in conformity in all material respects with GAAP (excluding footnote disclosure) applied on a basis consistent with the Financial Statements.
      5.14     Dissent Process. The Company shallwill give to Wintrust prompt written notice of any written notice or demands for appraisal for any Company Common Shares,Stock, any attempted withdrawals of any such demands and any other notice given or instrument served relating to the exercise of dissenters'dissenters’ rights granted under the WisconsinIllinois Act, including the name of each dissenting shareholder and the number of shares of Company Common SharesStock to which the dissent relates. Wintrust will have the right to participate in all negotiations and proceedings relating thereto, and exceptionsexcept as otherwise required by law. The Company will not make any payment with respect to, or settle or offer to settle, any appraisal demands without Wintrust'sWintrust’s prior written consent.
      5.15     Section 368(a) Reorganization. Either prior to or after the Closing Date, none of the Parties shall take or cause to be taken any action, or omit to take any action or cause any omission, which would cause the Merger not to qualify as a reorganization under Section 368(a) of the Code.
      5.16     TreatmentExercise of Options. Notwithstanding anything contained in this Agreement to the contrary, Wintrust and the Company each acknowledge and agree that the holder of any Outstanding Company Option may, at any time prior to the fifth (5th) calendar day precedingdate of commencement of the Closing Date,ten trading-day period for determining the Wintrust Common Stock Price pursuant to Section 2.1(b), exercise such Outstanding Company Option in accordance with its terms and conditions. A-24
      5.17     Converted Options. Wintrust agrees to assume and honor each of the Converted Options in accordance with their terms. As soon as reasonably practicable following the Closing Date, Wintrust shall file a registration statement with the Commission with respect to the shares of Wintrust Common Stock to be covered by such Converted Options. Such shares of Wintrust Common Stock shall be duly authorized

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and, upon exercise of such Converted Options, shall be validly issued, fully paid and nonassessable, and not in violation of or subject to any preemptive rights except as set forth in Wintrust'sWintrust’s articles of incorporation. Wintrust shall after the Effective Time have reserved sufficient shares of Wintrust Common Stock for issuance with respect to such options.
      5.18     Termination of Ownership Interests. Prior to the Effective Time the Company shall, and shall cause the Bank to, dissolve, wind up, liquidate or, in a manner reasonably satisfactory to Wintrust, terminate its ownership interest in, each of the subsidiaries and other interests identified on Schedule 3.3(b).
ARTICLE 6 VI
EMPLOYEE BENEFIT MATTERS
      6.1     Benefit Plans. Schedule 6.1 lists all of the employees of the Company and each of the SubsidiariesBank (the "Employees"Employees). Wintrust and the Company Board shall together review the Benefit Plans and the coverages provided thereunder. Effective as of the Closing Date, (i) theThe Company Board shall cause the Company to terminate effective as of the Closing Date all Benefit Plans other than the Company'sCompany’s 401(k) plan, health, life and disability insurance plans, and long-term care plan and other than the Company’s deferred compensation agreements, which are required to be amended under this Agreement pursuant to the terms of Section 7.13 (the "Retained Plans"Retained Plans), and to pay prior to the Closing or accrue fully any liabilities under the Benefit Plans (including the Retained Plans) or arising out of such termination of Benefit Plans, and (ii)Plans. Effective as of the Closing Date each full-time Employee shall become eligible for and entitled to participate in Wintrust'sWintrust’s benefit plans (other than those benefit plans for which such Employee is covered under the Retained Plans) on the same terms and subject to the same conditions as all other U.S. employees of Wintrust and its subsidiaries. From and after the Closing Date Wintrust shall continue coverage for the Employees under the Company's Retained Plans in effect prior to the Closing Date, to the extent not in violation of any statute, law (including common law), ordinance, rule or regulation applicable to such plans or the qualifications or requirements of such plans, until such time as Wintrust determines such plans are to be terminated or merged with existing Wintrust plans, at which time all Employees previously covered under such Retained Plans shall become eligible for and entitled to participate in Wintrust'sWintrust’s similar plans on the same terms and subject to the same conditions as all other U.S. employees of Wintrust and its subsidiaries. To the extent permitted by applicable law, the Company shall notifycause its health insurance provider to (i) provide to Wintrust ona schedule of de-identified information regarding the Closing Dateclaims experience of insured persons under the existenceapplicable Benefit Plans, and (ii) inform Wintrust of whether such health provider is aware of any significant pre-existing conditions of any insureds under the Benefit Plans of which the Company has knowledge.insured persons that are not reflected in such schedule. Wintrust shall use its reasonable and diligent efforts to cause any pre-existing condition limitations under Wintrust'sWintrust’s medical benefit plans to be waived to the extent such conditions have been waived under the Retained Plans.Company’s health insurance plans. For purposes of determining eligibility to participate in and, where applicable, vesting under Wintrust'sWintrust’s applicable retirement savings plan and employee stock purchase plan, Wintrust'sWintrust’s short-term disability plans and vacation policy, each Employee shall receive past service credit for his or her prior employment with the Company or the Subsidiaries as if such Employee had then been employed by Wintrust. Wintrust reserves the right to change or terminate its employee benefit plans at any time.
      6.2     Termination of ESOP; Redemption of ESOP Shares. (a) Prior to the Effective Time, the Company shall (i) terminate the Delafield State Bank (now known as Town Bank) Employee Stock Ownership Plan (the "ESOP"), and as promptly as practicable thereafter request from the IRS a favorable determination letter as to the tax qualified status of the ESOP upon its termination under Section 401(a) of the Code (the "Final Determination Letter"), (ii) redeem for cash, in an amount per share equal to the sum of $58.10 plus the cash value of the Per Share Stock Consideration based on the Wintrust Common Stock Price (or such other amount as may be agreed between the Parties) (the "ESOP Share Redemption Price"), (1) all unallocated Company Common Shares held by the ESOP and (2) all Company Common Shares allocated to the ESOP accounts of those current or former employees of the Company and the Subsidiaries who are ESOP participants and beneficiaries (the "ESOP Participants") (collectively, the "ESOP Shares," and such redemption, the "ESOP Share Redemption"); and (iii) cause the loan between the Company and the ESOP Trust to be repaid in full from the cash consideration received pursuant to the ESOP Share Redemption for such unallocated ESOP Shares. Any remaining cash consideration received for such unallocated ESOP Shares after such repayment shall be allocated as investment earnings to the ESOP accounts of each ESOP Participant in accordance with the terms of the ESOP. The cash proceeds received in the ESOP Share Redemption by each ESOP Participant for the ESOP Shares allocated to such ESOP Participant shall be allocated to each ESOP Participant account. All ESOP Participants shall fully vest and have a nonforfeitable interest in their ESOP accounts (including such allocations of the remaining cash consideration received for the unallocated Company Common Shares and such proceeds from the redemption of the allocated Company Common Shares) determined as of the Effective Time. A-25 (b) As soon as practicable after the receipt of the Final Determination Letter, distributions of the benefits under the ESOP shall be made to the ESOP Participants. (c) From and after the date of this Agreement, in anticipation of such termination and distribution, the Company and its representatives before the Effective Time, and the Surviving Corporation and its representatives after the Effective Time, shall use their reasonable and diligent efforts to obtain such favorable Final Determination Letter from the IRS. If the Company and its representatives, before the Effective Time, and the Surviving Corporation and its representatives, after the Effective Time, reasonably determine that the ESOP cannot obtain a favorable Final Determination Letter, or that the amounts held therein cannot be so applied, allocated or distributed without causing the ESOP to lose its tax qualified status, then the Company before the Effective Time, and the Surviving Corporation after the Effective Time, shall take such action as they may reasonably determine with respect to the distribution of benefits to the ESOP Participants, provided that the assets of the ESOP shall be held or paid only for the benefit of the ESOP Participants and provided further that in no event shall any portion of the amounts held in the ESOP revert, directly or indirectly, to the Company or any Subsidiary, or to Wintrust or any affiliate thereof. 6.3 No Rights or Remedies. Nothing in this Article shall confer upon any Employee or his or her legal representative, any rights or remedies, including any right to employment, or continued employment, for any specified period, or any nature or kind whatsoever under or by reason of this Agreement.

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ARTICLE 7 VII
CONDITIONS PRECEDENT TO
OBLIGATIONS OF WINTRUST
      Unless the conditions are waived by Wintrust, all obligations of Wintrust under this Agreement are subject to the fulfillment, on or before the Closing, of each of the following conditions: 7.1 Representations and Warranties; Performance of Agreements. Each of the representations and warranties contained in Article III of this Agreement shall be true and correct in all respects as of the Closing Date (except to the extent such representations and warranties speak as of an earlier date, they shall be tested as of such earlier date); provided, however, that for purposes of this Section 7.1, such representations and warranties shall be deemed to be true and correct unless the failure or failures of such representations and warranties to be so true and correct shall represent, individually or in the aggregate, a Company Material Impact. As used in this Article VII, "Company Material Impact" shall mean an adverse effect on the Company which would be reasonably likely to cause the Company to suffer (a) damages and expenses (including reasonable attorneys,' accountants' and financial advisors' fees) in excess of a gross amount of $500,000 in the aggregate (without regard to any attendant tax benefits of such damages or expenses), as a result of such failure of the Company's representations and warranties to be true and correct or (b) significant harm to the management, operations, reputation, business or assets of the Company and the Subsidiaries taken as a whole. The Company shall have performed in all material respects all agreements herein required to be performed by the Company on or before the Closing. 7.2 Closing Certificate. Wintrust shall have received a certificate of the Company signed by a senior executive officer of the Company, dated as of the Closing Date, certifying in such detail as Wintrust may reasonably request, as to the fulfillment of the conditions to the obligations of Wintrust set forth in this Agreement that are required to be fulfilled by the Company on or before the Closing. 7.3 Regulatory and Other Approvals. Wintrust shall have obtained the approval of all appropriate regulatory entities of the transactions contemplated by this Agreement and the Merger, all required regulatory waiting periods shall have expired, and there shall be pending on the Closing Date no motion for rehearing or appeal from such approval or any suit or action seeking to enjoin the Merger or to obtain substantial damages in respect of such transaction. 7.4 Approval of Merger and Delivery of Agreement. This Agreement and the Merger shall have been approved by the shareholders of the Company in accordance with the Company's articles of incorporation, by-laws and the Wisconsin Act, and the proper officers of the Company shall have executed and delivered to Wintrust copies of this Agreement and the Articles of Merger, in form suitable for filing with the Secretary of State of the State of Illinois and the WDFI, and shall have executed and delivered all such other A-26 certificates, statements or instruments as may be necessary or appropriate to effect such a filing. The holders, in the aggregate, of not more than 10% of the Company Common Shares shall have given written demand for dissenter's rights in accordance with the Wisconsin Act. 7.5 Effectiveness of the Registration Statement. The Registration Statement shall have become effective with respect to the shares of Wintrust Common Stock to be issued in the Merger, no stop order suspending the effectiveness of such Registration Statement shall have been issued, and no material proceeding for that purpose shall have been instituted or threatened. 7.6 No Litigation. No suit or other action shall have been instituted or threatened seeking to enjoin the consummation of the Merger or to obtain other relief in connection with this Agreement or the transactions contemplated herein that Wintrust believes, in good faith and with the written advice of outside counsel, makes it inadvisable to consummate the Merger by reason of the probability that the proceeding would result in the issuance of an order enjoining the Merger or in a determination that the Company or the Bank has failed to comply with applicable legal requirements of a material nature in connection with the Merger or actions preparatory thereto or would have a Company Material Impact. 7.7 Termination of ESOP. The Company shall have terminated the ESOP and completed the ESOP Share Redemption pursuant to Section 6.2. 7.8 Opinion of Counsel. Wintrust shall have received the opinion of Reinhart Boerner Van Dueren s.c., counsel for the Company, dated as of the Closing Date, and in form substantially similar to Exhibit C and reasonably satisfactory to Wintrust and its counsel. 7.9 Employment Agreements. Those persons identified on Schedule 7.9 shall each have entered into an employment agreement with Wintrust and the Surviving Corporation, dated the Closing Date, in substantially the form attached hereto as Exhibit D. 7.10 No Adverse Changes. Between the date of this Agreement and the Closing Date, there shall not have occurred any change or any condition, event, circumstance, fact or occurrence, other than as provided in this Agreement, that would have a Material Adverse Effect on the Company. 7.11 Minimum Net Worth and Loan Loss Reserve Requirements. (a) As of the Closing Date, as determined in conformity with GAAP applied on a basis consistent with the preparation of the Financial Statements, the shareholders' equity in the Company, after disregarding the effect of any adjustments made pursuant to FAS 115, shall be not less than the sum of (1) $17,400,000 plus (2) any cash receipts and attendant tax benefits recorded from the exercise of Outstanding Company Options in accordance with Section 5.16 minus (3) fees for attorneys, accountants or financial advisors actually incurred by the Company in connection with this Agreement and the transactions contemplated hereby, up to a maximum amount for such fees of $300,000 minus (4) the amount paid to redeem the ESOP Shares pursuant to the ESOP Share Redemption but not in excess of the ESOP Share Redemption Price per each ESOP Share, provided that the Company shall have no more than $6,186,000 in outstanding principal of holding company-level debt (including trust preferred securities). (b) As of the Closing Date, as determined in conformity with past practices and policies of the Bank and GAAP applied on a basis consistent with the preparation of the Financial Statements, the Bank's reserve for loan losses, determined as described in Section 3.8, shall be not less than 1.0% of the Bank's net Loans (gross Loans less unearned discounts). 7.12 Consents. The Company shall have obtained or caused to be obtained (a) all written consents under those Material Contracts as set forth on Schedule 3.5, and (b) all other written consents, permissions and approvals as required under any other agreements, contracts, appointments, indentures, plans, trusts or other arrangements with third parties required to effect the transactions contemplated by this Agreement where the failure to obtain such consents, permissions and approvals would have a Material Adverse Effect on the Company or Wintrust. A-27 7.13 Amendments to Deferred Compensation Agreement. On or before the Closing Date, the Company shall have delivered to Wintrust fully-executed amendments to each of those Incentive Deferred Compensation Agreements entered into between the Bank and those Bank executives named in Section (d)(2) of Schedule 3.10 (the "Deferred Compensation Agreements"), which amendments shall be in form and substance reasonably satisfactory to Wintrust. 7.14 Other Documents. Wintrust shall have received at the Closing such other customary documents, certificates, or instruments as they may have reasonably requested evidencing compliance by the Company with the terms and conditions of this Agreement.
      7.1     Representations and Warranties; Performance of Agreements. Each of the representations and warranties contained in Article III of this Agreement that are qualified by materiality shall be true and correct in all respects as of the Closing Date, and each of the representations and warranties contained in Article III that are not qualified by materiality shall be true and correct in all material respects, except to the extent such representations and warranties speak as of an earlier date, they shall be tested as of such earlier date. The Company shall have performed in all material respects all agreements herein required to be performed by the Company on or before the Closing.
      7.2     Closing Certificate. Wintrust shall have received a certificate of the Company signed by a senior executive officer of the Company, dated as of the Closing Date, certifying in such detail as Wintrust may reasonably request, as to the fulfillment of the conditions to the obligations of Wintrust set forth in this Agreement that are required to be fulfilled by the Company on or before the Closing.
      7.3     Regulatory and Other Approvals. Wintrust shall have obtained the approval of all appropriate regulatory entities of the transactions contemplated by this Agreement and the Merger, all required regulatory waiting periods shall have expired, and there shall be pending on the Closing Date no motion for rehearing or appeal from such approval or any suit or action seeking to enjoin the Merger or to obtain substantial damages in respect of such transaction.
      7.4     Approval of Merger and Delivery of Agreement. This Agreement and the Merger shall have been approved by the shareholders of the Company in accordance with the Company’s articles of incorporation, by-laws and the Illinois Act, and the proper officers of the Company shall have executed and delivered to Wintrust the Articles of Merger, in form suitable for filing with the Illinois Secretary of State, and shall have executed and delivered all such other certificates, statements or instruments as may be necessary or appropriate to effect such a filing. The holders of not more than 5% of the shares of Company Common Stock shall have given written demand for dissenter’s rights in accordance with the Illinois Act.
      7.5     Effectiveness of the Registration Statement. The Registration Statement shall have become effective with respect to the shares of Wintrust Common Stock to be issued in the Merger, no stop order suspending the effectiveness of such Registration Statement shall have been issued and no proceeding for that purpose shall have been instituted or threatened in writing.
      7.6     No Litigation. No suit or other action shall have been instituted or threatened in writing seeking to enjoin the consummation of the Merger or to obtain other relief in connection with this Agreement or the transactions contemplated herein that Wintrust believes, in good faith and with the written advice of outside counsel, makes it undesirable or inadvisable to consummate the Merger by reason of the probability that the proceeding would result in the issuance of an order enjoining the Merger or in a determination that the Company or the Bank has failed to comply with applicable legal requirements of a material nature in connection with the Merger or actions preparatory thereto or would have a Material Adverse Effect on the Company or the Bank.
      7.7     Environmental Surveys. Wintrust shall have the right, at its sole option and cost, to obtain Phase I environmental audits of all real property or facilities owned or used by either the Company or the Bank in the conduct of their respective businesses, conducted by an independent environmental consultant selected by Wintrust. No such environmental audit shall have identified any violation of the Environmental Laws or condition relating to the environment, human health or safety which could reasonably be expected to have a Material Adverse Effect on the Company.

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      7.8     Opinion of Counsel. Wintrust shall have received the opinion of Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP, counsel for the Company, dated as of the Closing Date, and in form substantially similar toExhibit B and reasonably satisfactory to Wintrust and its counsel.
      7.9     Employment Agreements. Those persons identified on Schedule 7.9 shall each have entered into an employment agreement with Wintrust or the Bank, dated the Closing Date, in substantially the form attached asExhibit C, and shall each be capable of performing his or her duties under his or her employment agreement as of the Closing Date.
      7.10     No Adverse Changes. Between the date of this Agreement and the Closing Date, the business of the Company and the Bank, taken as a whole, shall have been conducted in the Ordinary Course of Business, except as otherwise required under this Agreement, in all respects consistent with prudent banking practices, and there shall not have occurred any change or any condition, event, circumstance, fact or occurrence, other than as required under this Agreement, that would have a Material Adverse Effect on the Company.
      7.11     Minimum Net Worth and Loan Loss Reserve Requirements. The Company shall have delivered to Wintrust a balance sheet as of the Closing Date (the “Closing Balance Sheet”), prepared in conformity with past practices and policies of the Company and GAAP applied on a basis consistent with the preparation of the Financial Statements, which shall reflect that shareholders’ equity in the Company, adjusted to reflect the following adjustments, specifications and charges (which adjustments, specifications and charges are each separate conditions hereunder and shall be made by the Company on or prior to the Closing Date), shall be equal to or greater than the sum of $40,600,000.00plus any cash receipts and attendant tax benefits recorded from the exercise of Options in accordance with Section 5.16 (such sum, after giving effect to such adjustments, specifications and charges, the “Minimum Adjusted Net Worth”):
      (a) the Closing Balance Sheet shall reflect accruals for, on an after-tax basis as appropriate, (i) any professional fees and expenses (including legal, investment banking and accounting fees) actually incurred by the Company in connection with this Agreement and the transactions contemplated hereby, (ii) change of control payments due to any officers, directors or employees under any change in control, deferred compensation, employment or other agreements with the Company as a result of the Merger, which shall be paid or accrued by the Company concurrently with the Closing, and (iii) that amount to be paid by the Company in accordance with Section 7.14;
      (b) any changes in the Other Comprehensive Income account recorded as equity after June 30, 2005 shall be disregarded for purposes of determining Minimum Adjusted Net Worth;
      (c) the Company shall have no more than $8,000,000 of indebtedness (including any subordinated or senior debt or debentures); and
      (d) the Bank’s reserve for loan losses, determined as described in Section 3.8, shall be not less than 1.00% of the Bank’s net Loans (gross Loans less unearned discounts).
The Company may distribute to its shareholders immediately prior to Closing the amount by which shareholders’ equity is greater than the Minimum Adjusted Net Worth.
      7.12     Voting Agreements. On or before December 19, 2005, Wintrust shall have received a Voting Agreement, in the form attached hereto asExhibit D, executed by each of those shareholders of the Company identified on Schedule 7.12.
      7.13     Amendments to Deferred Compensation Agreements. Prior to the Effective Time, the Company shall have amended those deferred compensation and deferred fee agreements entered into between the Company and certain employees as set forth on Schedule 7.13, which amendments shall be in the forms attached hereto asExhibit E.

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      7.14     Settlement. The Company shall have accrued on the Closing Balance Sheet that amount described on Schedule 7.14, to be paid at or immediately following Closing in settlement of the potential claim described on Schedule 7.14, and the Company shall have used its best efforts to obtain a release in a form reasonably satisfactory to Wintrust of any claim against the Company or the Bank.
      7.15     Consents. The Company shall have obtained or caused to be obtained (a) all written consents under those Material Contracts set forth on Schedule 3.5, and (b) all other written consents, permissions and approvals as required under any agreements, contracts, appointments, indentures, plans, trusts or other arrangements with third parties required to effect the transactions contemplated by this Agreement where failure to obtain such consents, permissions and approvals would have a Material Adverse Effect on the Company or Wintrust’s rights under this Agreement.
      7.16     Other Documents. Wintrust shall have received at the Closing such other customary documents, certificates, or instruments as they may have reasonably requested evidencing compliance by the Company with the terms and conditions of this Agreement.
ARTICLE 8 VIII
CONDITIONS PRECEDENT TO OBLIGATIONS OF THE COMPANY
      Unless the conditions are waived by the Company, all obligations of the Company under this Agreement are subject to the fulfillment, on or before the Closing, of each of the following conditions: 8.1 Representations and Warranties; Performance of Agreements. Each of the representations and warranties contained in Article IV of this Agreement shall be true and correct in all respects as of the Closing Date (except to the extent such representations and warranties speak as of an earlier date, they shall be tested as of such earlier date); provided, however, that for purposes of this Section 8.1, such representations and warranties shall be deemed to be true and correct unless the failure or failures of such representations and warranties to be so true and correct shall represent, individually or in the aggregate, a Wintrust Material Impact. As used in this Section 8.1, a "Wintrust Material Impact" shall mean an adverse effect on Wintrust which would be reasonably likely to cause Wintrust to suffer (a) damages and expenses (including reasonable attorneys', accountants' and financial advisors' fees) in excess of $10,000,000 in the aggregate (net of any attendant tax benefits of such damages and expenses) as a result of such failure of Wintrust's representations and warranties to be true and correct or (b) significant harm to the management, operations, reputation, business or assets of Wintrust and its subsidiaries taken as a whole. Wintrust shall have performed in all material respects all agreements herein required to be performed by Wintrust on or before the Closing. 8.2 Closing Certificates. The Company shall have received certificates signed by the Chief Executive Officer, a Senior Executive Vice President, an Executive Vice President, or a Senior Vice President of Wintrust dated as of the Closing Date, certifying in such detail as the Company may reasonably request, as to the fulfillment of the conditions to the obligations of the Company as set forth in this Agreement. 8.3 Regulatory and Other Approvals. Wintrust shall have obtained the approval of all appropriate regulatory entities of the transactions contemplated by this Agreement and the Merger, all required regulatory waiting periods shall have expired, and there shall be pending on the Closing Date no motion for rehearing or appeal from such approval or any suit or action seeking to enjoin the Merger or to obtain substantial damages in respect of such transaction. 8.4 Approval of Merger and Delivery of Agreement. This Agreement and the Merger shall have been approved by the shareholders of the Company in accordance with the Company's articles of incorporation, bylaws and the Wisconsin Act, and the proper officers of Wintrust shall have executed and delivered to the Company copies of this Agreement and the Articles of Merger, in form suitable for filing with the Secretary of State of the State of Illinois and the WDFI, and shall have executed and delivered all such other certificates, statements or instruments as may be necessary or appropriate to effect such a filing. 8.5 Effectiveness of the Registration Statement. The Registration Statement shall have become effective with respect to the shares of Wintrust Common Stock to be issued in the Merger, no stop order suspending the effectiveness of such Registration Statement shall have been issued, no proceeding for that purpose shall have been instituted or threatened, and all requests for additional information on the part of the Commission shall have been complied with to the Company's satisfaction. 8.6 No Litigation. No suit or other action shall have been instituted or threatened seeking to enjoin the consummation of the Merger or to obtain other relief in connection with this Agreement or the transactions contemplated herein that the Company believes, in good faith and with the written advice of outside A-28 counsel, makes it inadvisable to consummate the Merger by reason of the probability that the proceeding would result in the issuance of an order enjoining the Merger or in a determination that Wintrust has failed to comply with applicable legal requirements of a material nature in connection with the Merger or actions preparatory thereto or would have a Material Adverse Effect on Wintrust. 8.7 Opinions of Counsel. (a) The Company shall have received the opinion of Schiff Hardin LLP, special counsel for Wintrust, dated as of the Closing Date, and in form substantially similar to Exhibit E and reasonably satisfactory to the Company and its counsel. (b) The Company shall have received the opinion of Reinhart Boerner Van Dueren s.c., counsel to the Company, dated as of the Closing Date, to the effect that the Merger will constitute a "reorganization" within the meaning of Section 368(a) of the Code, that the Company and Wintrust will each be a party to such reorganization within the meaning of Section 368(a) of the Code, and that no gain or loss will be recognized by the holders of Company Common Shares upon the receipt of Wintrust Common Stock in exchange for their Company Common Shares, except to the extent of the Per Share Cash Consideration and any cash received in lieu of fractional share of Wintrust Common Stock. The tax opinion shall be supported by one or more fact certificates or affidavits from Wintrust, in such form and content as may reasonably be requested by counsel to the Company. 8.8 No Adverse Changes. Between the date of this Agreement and the Closing Date, there shall not have occurred any change or any condition, event, circumstance, fact or occurrence that would have a Material Adverse Effect on Wintrust. 8.9 Nasdaq Listing. The Wintrust Common Stock to be issued to holders of Company Common Shares pursuant to the Merger shall have been approved for listing on the Nasdaq National Market subject to official notice of issuance if required. 8.10 Other Documents. The Company shall have received at the Closing all such other customary documents, certificates, or instruments as they may have reasonably requested evidencing compliance by Wintrust with the terms and conditions of this Agreement.
      8.1     Representations and Warranties; Performance of Agreements. Each of the representations and warranties contained in Article IV of this Agreement that are qualified by materiality shall be true and correct in all respects as of the Closing Date, and each of the representations and warranties contained in Article IV that are not qualified by materiality shall be true and correct in all material respects, except to the extent such representations and warranties speak as of an earlier date, they shall be tested as of such earlier date. Wintrust shall have performed in all material respects all agreements herein required to be performed by Wintrust on or before the Closing.
      8.2     Closing Certificates. The Company shall have received certificates signed by the Chief Executive Officer, a Senior Executive Vice President, an Executive Vice President, or a Senior Vice President of Wintrust dated as of the Closing Date, certifying in such detail as the Company may reasonably request, as to the fulfillment of the conditions to the obligations of the Company as set forth in this Agreement.
      8.3     Regulatory and Other Approvals. Wintrust shall have obtained the approval of all appropriate regulatory entities of the transactions contemplated by this Agreement and the Merger, all required regulatory waiting periods shall have expired, and there shall be pending on the Closing Date no motion for rehearing or appeal from such approval or any suit or action seeking to enjoin the Merger or to obtain substantial damages in respect of such transaction.
      8.4     Delivery of Agreement. The proper officers of Wintrust shall have executed and delivered to the Company the Articles of Merger, in form suitable for filing with the Illinois Secretary of State, and shall have executed and delivered all such other certificates, statements or instruments as may be necessary or appropriate to effect such a filing.
      8.5     Effectiveness of the Registration Statement. The Registration Statement shall have become effective with respect to the shares of Wintrust Common Stock to be issued in the Merger, no stop order suspending the effectiveness of such Registration Statement shall have been issued, no proceeding for that purpose shall have been instituted or threatened in writing.
      8.6     No Litigation. No suit or other action shall have been instituted or threatened in writing seeking to enjoin the consummation of the Merger or to obtain other relief in connection with this Agreement or the transactions contemplated herein that the Company believes, in good faith and with

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the written advice of outside counsel, makes it undesirable or inadvisable to consummate the Merger by reason of the probability that the proceeding would result in the issuance of an order enjoining the Merger or in a determination that Wintrust has failed to comply with applicable legal requirements of a material nature in connection with the Merger or actions preparatory thereto or would have a Material Adverse Effect on Wintrust.
      8.7     Opinions of Counsel.
      (a) The Company shall have received the opinion of Schiff Hardin LLP, special counsel for Wintrust, dated as of the Closing Date, and in form substantially similar toExhibit F and reasonably satisfactory to the Company and its counsel.
      (b) The Company shall have received the opinion of Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP, counsel for the Company, dated as of the Closing Date, to the effect that the Merger will constitute a “reorganization” within the meaning of Section 368(a) of the Code, that the Company and Wintrust will each be a party to such reorganization within the meaning of Section 368(a) of the Code, and that no gain or loss will be recognized by the holders of shares of Company Common Stock upon the receipt of shares of Wintrust Common Stock in exchange for their shares of Company Common Stock, except to the extent of any Cash Consideration received in the Merger and any cash received in lieu of fractional shares of Wintrust Common Stock. The tax opinion shall be supported by one or more fact certificates or affidavits from Wintrust and the Company, in such form and content as may reasonably be requested by counsel to the Company.
      8.8     No Adverse Changes. Between the date of this Agreement and the Closing Date, there shall not have occurred any change or any condition, event, circumstance, fact or occurrence, other than as provided in this Agreement, that would have a Material Adverse Effect on Wintrust.
      8.9     Nasdaq Listing. The Wintrust Common Stock to be issued to holders of Company Common Stock pursuant to the Merger shall have been approved for listing on the Nasdaq National Market, subject to official notice of issuance if required.
      8.10     Other Documents. The Company shall have received at the Closing all such other customary documents, certificates, or instruments as they may have reasonably requested evidencing compliance by Wintrust with the terms and conditions of this Agreement.

ARTICLE 9 IX
NON-SURVIVAL OF REPRESENTATIONS, WARRANTIES AND COVENANTS
      9.1     Non-Survival. None of the representations, warranties, covenants and agreements in this Agreement shall survive the Effective Time, except for those covenants or agreements contained herein which by their terms apply and shall survive, in whole or in part after the Effective Time. Without limiting the foregoing, none of the directors or officers of the Parties shall have any liability for any of the representations, warranties, covenants and agreements contained herein.
ARTICLE 10 X
GENERAL
      10.1     Expenses. Except as otherwise provided in this Section 10.1, all costs and expenses incurred in the consummation of this transaction, including any brokers'brokers’ or finders'finders’ fees, shall be paid by the Party incurring such cost or expense. (a) Each of Wintrust and the Company shall bear and pay one-half of the costs and expenses incurred in connection with the printing and mailing of the Registration Statement, excluding legal, appraisal and accounting fees and expenses related thereto which shall be paid by the Party incurring such fees and expenses. Registration Statement filing fees to be paid to the Commission shall be borne and paid by Wintrust. (b) In the event that this Agreement is terminated by Wintrust because the Company or the Subsidiaries committed a material breach of its material obligations under this Agreement, unless such breach is a result of the failure by Wintrust to perform and comply in all material respects with any of its material A-29 obligations under this Agreement which are to be performed or complied with by it prior to or on the date of such termination, then, provided Wintrust is in material compliance with all of its material obligations under this Agreement, the Company shall reimburse Wintrust in an amount equal to $300,000 for the out-of-pocket expenses and costs that Wintrust (x) has incurred in furtherance of this Agreement and the transactions contemplated herein and (y) is reasonably expected to incur as a result of the Company's breach of this Agreement, including, but not limited to, reasonable fees of professionals engaged for such purpose by or on behalf of Wintrust; provided, however, that except as provided in Section 10.1(c), such sum shall constitute liquidated damages and the receipt thereof shall be Wintrust's sole and exclusive remedy under this Agreement. Notwithstanding the foregoing, if this Agreement is terminated by Wintrust as a result of the Company's willful breach of this Agreement, then in addition to recovery of its out-of-pocket expenses and costs, Wintrust shall be entitled to recover such other amounts as it may be entitled to receive at law or in equity. (c) In the event that this Agreement is terminated (i) by Wintrust as a result of a breach by the Company of its covenant in Section 5.8(a), (ii) by the Company pursuant to Section 10.2(e), or (iii) pursuant to Sections 10.2(a) or 10.2(b) and in each such case within six months after the date of such termination described in clause (i), (ii) or (iii) the Company or the Bank has either consummated or entered into a definitive agreement relating to an Acquisition Proposal which was made known to any member of the Company Board and not disclosed to Wintrust prior to the date of such termination, then the Company shall pay to Wintrust a termination fee equal to $1,000,000. Such sum shall constitute liquidated damages and the receipt thereof shall be Wintrust's sole and exclusive remedy under this Agreement, absent fraud or willful misconduct on the part of the Company, in which event Wintrust shall be entitled to recover such other amounts as it may be entitled to receive at law or in equity. (d) In the event that this Agreement is terminated by the Company because Wintrust committed a material breach of its material obligations under this Agreement, unless such breach is a result of the failure by the Company or the Bank to perform and comply in all material respects with any of its material obligations under this Agreement which are to be performed or complied with by it prior to or on the date of such termination, then, provided the Company and the Bank are each in material compliance with all of its material obligations under this Agreement, Wintrust shall reimburse the Company in an amount equal to $300,000 for the out-of-pocket expenses that the Company (i) has incurred in furtherance of this Agreement and the transactions contemplated herein and (ii) is reasonably expected to incur as a result of Wintrust's breach of this Agreement, including, but not limited to, reasonable fees of professionals engaged for such purpose by or on behalf of the Company; provided, however, that such sums shall constitute liquidated damages and the receipt thereof shall be the Company's sole and exclusive remedy under this Agreement. Notwithstanding the foregoing, if this Agreement is terminated by the Company as a result of Wintrust's willful breach of this Agreement, then in addition to recovery of its out-of-pocket expenses and costs, the Company shall be entitled to recover such other amounts as it may be entitled to receive at law or in equity. (e) In the event this Agreement is terminated pursuant to Section 10.2(b) because Wintrust fails to obtain all of the necessary regulatory approvals described in Sections 7.3 and 8.3 for any reason other than regulatory matters relating solely to the Company or the Subsidiaries, Wintrust shall pay to the Company $300,000, provided, however, that such sums shall constitute liquidated damages and the receipt thereof shall be the Company's sole and exclusive remedy under this Agreement. (f) In the event this Agreement is terminated pursuant to Section 10.2(b) because Wintrust fails to obtain all of the necessary regulatory approvals described in Sections 7.3 and 8.3 because of regulatory matters relating solely to the Company or the Subsidiaries, the Company shall pay to Wintrust $300,000, provided, however, that except as provided in Section 10.1(c), such sums shall constitute liquidated damages and the receipt thereof shall be Wintrust's sole and exclusive remedy under this Agreement. (g)
      (a) Each of Wintrust and the Company shall bear and pay one-half of the costs and expenses incurred in connection with the printing and mailing of the Proxy Statement/ Prospectus, excluding legal and accounting fees and expenses related thereto which shall be borne and paid by the Party incurring such fees and expenses. Registration Statement filing fees to be paid to the Commission shall be borne and paid by Wintrust.

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      (b) In the event that this Agreement is terminated by Wintrust because the Company committed a material breach of its material obligations under this Agreement, unless such breach is a result of the failure by Wintrust to perform and comply in all material respects with any of its material obligations under this Agreement which are to be performed or complied with by it prior to or on the date of such termination, then, provided Wintrust is in material compliance with all of its material obligations under this Agreement, the Company shall reimburse Wintrust in an amount, not to exceed $250,000, for theout-of-pocket expenses and costs, subject to verification thereof, that Wintrust (i) has incurred in furtherance of this Agreement and the transactions contemplated herein and (ii) is reasonably expected to incur as a result of the Company’s breach of this Agreement, including, but not limited to, reasonable fees of professionals engaged for such purpose by or on behalf of Wintrust;provided,however, that except as provided in Section 10.1(c), such sums shall constitute liquidated damages and the receipt thereof shall be Wintrust’s sole and exclusive remedy under this Agreement. Notwithstanding the foregoing, if this Agreement is terminated by Wintrust as a result of the Company’s willful breach of this Agreement, then in addition to recovery of itsout-of-pocket expenses and costs, Wintrust shall be entitled to recover such other amounts, including consequential damages, as it may be entitled to receive at law or in equity.
      (c) In the event that this Agreement is terminated (i) by Wintrust as a result of a breach by the Company of its covenant in Section 5.8(a), (ii) by the Company pursuant to Section 10.2(e), or (iii) pursuant to Sections 10.2(b) or 10.2(c) and within six months after the date of such termination the Company or the Bank has either consummated or entered into a definitive agreement relating to an Acquisition Proposal which was made known to any member of the Company Board and not disclosed to Wintrust prior to the date of such termination, then the Company shall pay to Wintrust a termination fee equal to $1,000,000.
      (d) In the event that this Agreement is terminated by the Company because Wintrust committed a material breach of its material obligations under this Agreement, unless such breach is a result of the failure by the Company or the Bank to perform and comply in all material respects with any of its material obligations under this Agreement which are to be performed or complied with by it prior to or on the date of such termination, then, provided the Company is in material compliance with all of its material obligations under this Agreement, Wintrust shall reimburse the Company in an amount, not to exceed $250,000, for theout-of-pocket expenses and costs, subject to verification thereof, that the Company (i) has incurred in furtherance of this Agreement and the transactions contemplated herein and (ii) is reasonably expected to incur as a result of Wintrust’s breach of this Agreement, including, but not limited to, reasonable fees of professionals engaged for such purpose by or on behalf of the Company;provided,however, that such sums shall constitute liquidated damages and the receipt thereof shall be the Company’s sole and exclusive remedy under this Agreement. Notwithstanding the foregoing, if this Agreement is terminated by the Company as a result of Wintrust’s willful breach of this Agreement, then in addition to recovery of itsout-of-pocket expenses and costs, the Company shall be entitled to recover such other amounts, including consequential damages, as it may be entitled to receive at law or in equity.
      (e) In the event this Agreement is terminated pursuant to Section 10.2(b) because Wintrust fails to obtain all of the necessary regulatory approvals described in Sections 7.3 and 8.3 for any reason other than regulatory matters relating solely to the Company or the Bank, Wintrust shall pay to the Company $250,000,provided,however, that such sums shall constitute liquidated damages and the receipt thereof shall be the Company’s sole and exclusive remedy under this Agreement.
      (f) In the event this Agreement is terminated pursuant to Section 10.2(b) because Wintrust fails to obtain all of the necessary regulatory approvals described in Sections 7.3 and 8.3 because of regulatory matters relating solely to the Company or the Bank, the Company shall pay to Wintrust $250,000,provided,however, that except as provided in Section 10.1(c), such sums shall constitute liquidated damages and the receipt thereof shall be Wintrust’s sole and exclusive remedy under this Agreement.

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      All costs and expenses reasonably estimated to have been incurred by the Company shall be either paid or accrued for on or prior to the Closing Date;provided,however, that nothing in this Section 10.1 shall be deemed to relieve the Company of its liability to pay any expenses incurred in connection with this Agreement following the Closing.
      10.2     Termination. This Agreement may be terminated: A-30 (a) at any time by written agreement between Wintrust and the Company; (b) by either Wintrust or the Company if the Closing has not occurred (other than through the failure of any Party seeking to terminate this Agreement to comply fully with its material obligations under this Agreement) by November 30, 2004, or such later date agreed to by the Parties, provided, however, that such termination date shall automatically be extended until February 28, 2005, if the sole impediment to Closing is a delay in either (i) the determination of the effectiveness of the Registration Statement or (ii) the Federal Reserve's approval of the Federal Reserve Application or the WDFI's approval of the WDFI Application; (c) by Wintrust by written notice to the Company, if (i) any of the conditions in Article VII has not been satisfied as of the Closing Date or if satisfaction of such a condition is or becomes impossible (other than through the failure of Wintrust to comply with its obligations under this Agreement); and (ii) Wintrust has not waived such condition on or before the Closing Date; (d) by the Company by written notice to Wintrust, if (i) any of the conditions in Article VIII has not been satisfied as of the Closing Date or if satisfaction of such a condition is or becomes impossible (other than through the failure of the Company or the Subsidiaries to comply with its obligations under this Agreement); and (ii) the Company has not waived such condition on or before the Closing Date; or (e) by the Company, if in compliance with Section 5.8(b) the Company Board determines to accept an Acquisition Proposal from a third party, or by Wintrust if an Acquisition Proposal from a third party is accepted by the Company or consummated, in each case by written notice to the other party; or (f) by Wintrust, by written notice to the Company, in the event the Wintrust Common Stock Price, as determined pursuant to Section 1.4(a), is greater than $58.34 or by the Company, by written notice to Wintrust, if the Wintrust Common Stock Price is less than $38.34, provided, however, that neither Party may terminate this Agreement pursuant to this Section 10.2(f) unless and until five (5) business days have elapsed following the receipt of written notice of such termination, and during such five (5) business day period, the Parties in good faith are unable to reach agreement as to an amendment to this Agreement containing terms acceptable to both Parties so that the Merger and transactions contemplated hereby may be effected. (g)
      (a) at any time by written agreement between Wintrust and the Company;
      (b) by either Wintrust or the Company if the Closing has not occurred (other than through the failure of any Party seeking to terminate this Agreement to comply fully with its material obligations under this Agreement) by July 31, 2006, or such later date agreed to by the Parties,provided,however, that such termination date shall automatically be extended until August 31, 2006, if the sole impediment to Closing is a delay in either (i) the determination of the effectiveness of the Registration Statement or (ii) the Federal Reserve’s approval of the Federal Reserve Application;
      (c) by Wintrust by written notice to the Company, if (i) any of the conditions in Article VII has not been satisfied as of the Closing Date or if satisfaction of such a condition is or becomes impossible (other than through the failure of Wintrust to comply with its obligations under this Agreement); and (ii) Wintrust has not waived such condition on or before the Closing Date;
      (d) by the Company by written notice to Wintrust, if (i) any of the conditions in Article VIII has not been satisfied as of the Closing Date or if satisfaction of such a condition is or becomes impossible (other than through the failure of the Company or the Bank to comply with its obligations under this Agreement); and (ii) the Company has not waived such condition on or before the Closing Date; or
      (e) by the Company, if pursuant to Section 5.8(b) the Company Board determines that its fiduciary duties require it to accept an unsolicited Acquisition Proposal from a third party, or by Wintrust if an Acquisition Proposal from a third party is accepted by the Company or consummated, in each case by written notice to the other party; or
      (f) by the Company, if the Wintrust Common Stock Price is less than $47.14,provided,however, that the Company may not terminate the Agreement pursuant to this Section 10.2(f) unless and until five (5) business days have elapsed following the delivery to Wintrust of written notice of such termination, and prior to the end of such five (5) business-day period Wintrust fails to notify the Company in writing that Wintrust elects to increase (i) the number of shares of Wintrust Common Stock to be issued and/or (ii) the amount of cash to be paid in exchange for each Stock Election Share (after application of the proration and redesignation procedures provided for in Section 2.3 of this Agreement) so that the amount of consideration exchanged for each such Stock Election Share (valuing Wintrust Common Stock at the unweighted average of the high and low sales prices of a share of Wintrust Common Stock as reported on the Nasdaq National Market for each of the ten (10) trading days ending on the fourth (4th) trading day preceding the Closing) is equivalent to that amount of Stock Consideration which would be obtained using $47.14 as the Wintrust Common Stock Price. For example, if the Wintrust Common Stock Price is determined to be $46.14 and the Company notifies Wintrust of its intention to terminate this Agreement, Wintrust shall have the right to elect to increase the number of shares of Wintrust Common Stock and/or the amount of cash to be paid to those holders of Company Common Shares electing to receive Stock Consideration (whether through a Stock Election or a Combination Election) such that the consideration paid in exchange for each Stock Election Share is equivalent to the value (in shares of Wintrust Common Stock valued as described above, cash or a combination thereof) of that number of shares of Wintrust Common Stock, rounded to the nearest thousandth of a share, equal to $41.59 (the Price Per Share) divided by $47.14.
      Any termination of this Agreement shall not affect any rights accrued prior to such termination.

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      10.3     Confidential Information. Wintrust and the Company each covenant that, in the event the transactions contemplated by this Agreement are not consummated, each such Party will keep in strict confidence and return all documents containing any information concerning the properties, business, and assets of the other Parties that may have been obtained in the course of negotiations or examination of the affairs of each other Party either prior or subsequent to the execution of this Agreement (other than such information as shall be in the public domain or otherwise ascertainable from public or outside sources), except to the extent that disclosure is required by judicial process or governmental or regulatory authorities. This Section 10.3 is not intended to supercede any of the provisions of the Confidentiality Agreement, which shall survive the execution of this Agreement.
      10.4     Non-Assignment; Third-Party Beneficiaries.Non-Assignment. Neither this Agreement nor any of the rights, interests or obligations of the Parties under this Agreement shall be assigned by any Party (whether by operation of law or otherwise) without the prior written consent of the other Party. Notwithstanding the foregoing, Wintrust may assign its rights hereunder to aanother wholly owned subsidiary of Wintrust. Subject to the foregoing, this Agreement shall be binding upon and inure to the benefit of the respective successors and assigns of the Parties. From and after the Effective Time, nothing in this Agreement, express or implied, is intended to or shall confer upon any other person any right, benefit or remedy of any nature whatsoever under or by reason of this Agreement, other than Section 5.12 (which is intended to be for the benefit of the applicable directors and officers of the Company and may be enforced by such persons, their heirs or representatives, in accordance with the terms thereof).
      10.5     Notices. All notices, requests, demands, and other communications provided for in this Agreement shall be in writing and shall be deemed to have been given (a) when delivered in person, (b) the third business day after being deposited in the United States mail, registered or certified mail (return receipt requested), or A-31 (c) the first business day after being deposited with Federal Express or any other recognized national overnight courier service, in each case addressed as follows: (i) If to the Company, addressed to: Town Bankshares, Ltd. 400 Genesee Street Delafield, Wisconsin 53018 Attention: William J. Hickmann, Chairman of the Board and Jay C. Mack, President with a copy to: Reinhart Boerner Van Dueren s.c. 1000 North Water Street, Suite 2100 Milwaukee, Wisconsin 53202 Attention: Jerome M. Janzer (ii) If to Wintrust, addressed to: Wintrust Financial Corporation 727 North Bank Lane Lake Forest, Illinois 60045 Attention: David A. Dykstra Senior Executive Vice President and Chief Operating Officer with a copy to: Schiff Hardin LLP 6600 Sears Tower Chicago, IL 60606-6473
(i) If to the Company, addressed to:
Hinsbrook Bancshares, Inc.
6262 S. Route 83
Willowbrook, Illinois 60527
Attention: Mr. Robert K. Buhrke,
                      Chairman, Chief Executive Officer and President
with a copy to:
Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP
333 West Wacker Drive, Suite 2700
Chicago, Illinois 60606
Attention: Edwin S. del Hierro, Esq.
(ii) If to Wintrust, addressed to:
Wintrust Financial Corporation
727 North Bank Lane
Lake Forest, Illinois 60045
Attention: David A. Dykstra,
                      Senior Executive Vice President and
                      Chief Operating Officer
with a copy to:
Schiff Hardin LLP
6600 Sears Tower
Chicago, Illinois 60606-6473
Attention: Matthew G. Galo, Esq.
      10.6     Counterparts. This Agreement may be executed in any number of counterparts with the same effect as if the signatures to each counterpart were upon the same instrument.
      10.7     Knowledge. References in this Agreement to the "knowledge"knowledge of a Partyparty shall mean, (a)with respect to a natural person, the actual knowledge of such Party's executive officersperson after reasonable investigation and (b)with respect to an entity, the actual knowledge of such Party's directors.its officers and directors after reasonable investigation.

A-34


      10.8     Interpretation. The words “hereof,” “herein” and “herewith” and words of similar import shall, unless otherwise stated, be construed to refer to this Agreement as a whole. Article, Section, Exhibit and Schedule references are to the Articles, Sections, Exhibits and Schedules of this Agreement unless otherwise specified. The table of contents and headings contained in this Agreement are for reference purposes only and will not affect in any way the meaning or interpretation of this Agreement. Whenever the words “include,” “includes,” “including” or similar expressions are used in this Agreement, they will be understood to be followed by the words “without limitation.” The words describing the singular shall include the plural and vice versa, and words denoting any gender shall include all genders and words denoting natural persons shall include corporations, partnerships and other entities and vice versa. The parties have participated jointly in the negotiation and drafting of this Agreement. In the event of an ambiguity or question of intent or interpretation arises, this Agreement will be construed as if drafted jointly by the Parties and no presumption or burden of proof will arise favoring or disfavoring any Party by virtue of the authorship of any provision of this Agreement.
      10.9     Entire Agreement. This Agreement, including the Schedules and agreements delivered pursuant hereto, and the Confidentiality Agreement, sets forth the entire understanding of the parties and supersedes all prior agreements, arrangements, and communications, whether oral or written. This Agreement shall not be modified or amended other than by written agreement of the parties hereto. Captions appearing in this Agreement are for convenience only and shall not be deemed to explain, limit, or amplify the provisions hereof. 10.9
      10.10     Governing Law. This Agreement shall be governed by and construed in accordance with the laws of the State of Illinois, without giving effect to the conflicts of laws principles thereof. A-32 10.10
      10.11     Severability. In the event that a court of competent jurisdiction shall finally determine that any provision of this Agreement or any portion thereof is unlawful or unenforceable, such provision or portion thereof shall be deemed to be severed from this Agreement, and every other provision and portion thereof that is not invalidated by such determination shall remain in full force and effect. To the extent that a provision is deemed unenforceable by virtue of its scope but may be made enforceable by limitation thereof, such provision shall be enforceable to the fullest extent permitted under the laws and public policies of the state whose laws are deemed to govern enforceability. [Remainder of page intentionally left blank;
** Signature page follows] A-33 Page Follows **

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IN WITNESS WHEREOF,Wintrust Financial Corporation and Town Bankshares, Ltd.the Company have each executed this Agreement and Plan of Merger as of the day and year first written above. WINTRUST FINANCIAL CORPORATION By: /s/ David A. Dykstra Name: David A. Dykstra Title: Sr. Executive V.P.
WINTRUST FINANCIAL CORPORATION
By: /s/ David A. Dykstra
Name: David A. Dykstra
Title:Senior Executive Vice President
and Chief Operating Officer
HINSBROOK BANCSHARES, INC.
By: /s/ Robert K. Buhrke
Name: Robert K. Buhrke
Title:President and Chief Executive Officer
[Signature Page to Agreement and COO TOWN BANKSHARES, LTD. By: /s/ William J. Hickmann Name: William J. Hickmann Title: Chairman A-34 ANNEXPlan of Merger]

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Annex B SECTIONS 180.1301 THROUGH 180.1331 OF THE WISCONSIN BUSINESS CORPORATION LAW 180.1301 DEFINITIONS. In ss. 180.1301 to 180.1331: (1) "Beneficial shareholder" means a person who is a beneficial owner of shares held by a nominee as the shareholder. (1m) "Business combination" has the meaning given in s. 180.1130(3). (2) "Corporation" means the issuer corporation or, if the corporate action giving rise to dissenters' rights under s. 180.1302 is a merger or share exchange that has been effectuated, the surviving domestic corporation or foreign corporation
Sections 11.65 and 11.70 of the merger or the acquiring domesticIllinois Business Corporation Act of 1983,
as amended Dissenters’ Rights
      § 11.65.     Right to dissent. (a) A shareholder of a corporation or foreign corporation of the share exchange. (3) "Dissenter" means a shareholder or beneficial shareholder who is entitled to dissent from, corporate action under s. 180.1302 and who exercises that right when and in the manner required by ss. 180.1320 to 180.1328. (4) "Fair value", with respect to a dissenter's shares other than in a business combination, means the value of the shares immediately before the effectuation of the corporate action to which the dissenter objects, excluding any appreciation or depreciation in anticipation of the corporate action unless exclusion would be inequitable. "Fair value", with respect to a dissenter's shares in a business combination, means market value, as defined in s. 180.1130(9)(a) 1. to 4. (5) "Interest" means interest from the effectuation date of the corporate action until the date of payment, at the average rate currently paid by the corporation on its principal bank loans or, if none, at a rate that is fair and equitable under all of the circumstances. (6) "Issuer corporation" means a domestic corporation that is the issuer of the shares held by a dissenter before the corporate action. History: 1989 a. 303; 1991 a. 16. 180.1302 RIGHT TO DISSENT. (1) Except as provided in sub. (4) and s. 180.1008(3), a shareholder or beneficial shareholder may dissent from, and obtain payment of the fair value offor his or her shares in the event of any of the following corporate actions: (a) Consummation of a plan of merger to which the issuer corporation is a party if any of the following applies: 1. Shareholder approval is required for the merger by s. 180.1103 or by the articles of incorporation. 2. The issuer corporation is a subsidiary that is merged with its parent under s. 180.1104.
      (1) consummation of a plan of merger or consolidation or a plan of share exchange to which the corporation is a party if (i) shareholder authorization is required for the merger or consolidation or the share exchange by Section 11.20 or the articles of incorporation or (ii) the corporation is a subsidiary that is merged with its parent or another subsidiary under Section 11.30;
      (2) consummation of a sale, lease or exchange of all, or substantially all, of the property and assets of the corporation other than in the usual and regular course of business;
      (3) an amendment of the articles of incorporation that materially and adversely affects rights in respect of a dissenter’s shares because it:
      (i) alters or abolishes a preferential right of such shares;
      (ii) alters or abolishes a right in respect of redemption, including a provision respecting a sinking fund for the redemption or repurchase, of such shares;
      (iii) in the case of a corporation incorporated prior to January 1, 1982, limits or eliminates cumulative voting rights with respect to such shares; or
      (4) any other corporate action taken pursuant to a shareholder vote if the articles of incorporation, by-laws, or a resolution of the board of directors provide that shareholders are entitled to dissent and obtain payment for their shares in accordance with the procedures set forth in Section 11.70 or as may be otherwise provided in the articles, by-laws or resolution.
      (b) Consummation of a plan of share exchange if the issuer corporation's shares will be acquired, and the shareholder or the shareholder holding shares on behalf of the beneficial shareholder is entitled to vote on the plan. B-1 (c) Consummation of a sale or exchange of all, or substantially all, of the property of the issuer corporation other than in the usual and regular course of business, including a sale in dissolution, but not including any of the following: 1. A sale pursuant to court order. 2. A sale for cash pursuant to a plan by which all or substantially all of the net proceeds of the sale will be distributed to the shareholders within one year after the date of sale. (cm) Consummation of a plan of conversion. (d) Except as provided in sub. (2), any other corporate action taken pursuant to a shareholder vote to the extent that the articles of incorporation, bylaws or a resolution of the board of directors provides that the voting or nonvoting shareholder or beneficial shareholder may dissent and obtain payment for his or her shares. (2) Except as provided in sub. (4) and s. 180.1008(3), the articles of incorporation may allow a shareholder or beneficial shareholder to dissent from an amendment of the articles of incorporation and obtain payment of the fair value of his or her shares if the amendment materially and adversely affects rights in respect of a dissenter's shares because it does any of the following: (a) Alters or abolishes a preferential right of the shares. (b) Creates, alters or abolishes a right in respect of redemption, including a provision respecting a sinking fund for the redemption or repurchase, of the shares. (c) Alters or abolishes a preemptive right of the holder of shares to acquire shares or other securities. (d) Excludes or limits the right of the shares to vote on any matter or to cumulate votes, other than a limitation by dilution through issuance of shares or other securities with similar voting rights. (e) Reduces the number of shares owned by the shareholder or beneficial shareholder to a fraction of a share if the fractional share so created is to be acquired for cash under s. 180.0604. (3) Notwithstanding sub. (1)(a) to (c), if the issuer corporation is a statutory close corporation under ss. 180.1801 to 180.1837, a shareholder of the statutory close corporation may dissent from a corporate action and obtain payment of the fair value of his or her shares, to the extent permitted under sub. (1)(d) or (2) or s. 180.1803, 180.1813(1)(d) or (2)(b), 180.1815(3) or 180.1829(1)(c). (4) Except in a business combination or unless the articles of incorporation provide otherwise, subs. (1) and (2) do not apply to the holders of shares of any class or series if the shares of the class or series are registered on a national securities exchange or quoted on the National Association of Securities Dealers, Inc., automated quotations system on the record date fixed to determine the shareholders entitled to notice of a shareholders meeting at which shareholders are to vote on the proposed corporate action. (5) Except as provided in s. 180.1833, a shareholder or beneficial shareholder entitled to dissent and obtain payment for his or her shares under ss. 180.1301 to 180.1331this Section may not challenge the corporate action creating his or her entitlement unless the action is unlawful or fraudulent with respect to the shareholder beneficial shareholder or issuer corporation. History: 1959 a. 303; 1991 a. 16; 2001 a. 44. B-2 180.1303 DISSENT BY SHAREHOLDERS AND BENEFICIAL SHAREHOLDERS. (1)the corporation or constitutes a breach of a fiduciary duty owed to the shareholder.
      (c) A shareholderrecord owner of shares may assert dissenters'dissenters’ rights as to fewer than all of the shares registeredrecorded in his or hersuch person’s name only if the shareholdersuch person dissents with respect to all shares beneficially owned by any one person and notifies the corporation in writing of the name and address of each person on whose behalf he or shethe record owner asserts dissenters'dissenters’ rights. The rights of a shareholder who under this subsection asserts dissenters' rights as to fewer than all of the shares registered in his or her namepartial dissenter are determined as if the shares as to which he or she dissentsdissent is made and his or herthe other shares were registeredrecorded in the names of different shareholders. (2) A beneficial shareholderowner of shares who is not the record owner may assert dissenters'dissenters’ rights as to shares held on his or hersuch person’s behalf only if the beneficial shareholder does all of the following: (a) Submitsowner submits to the corporation the shareholder'srecord owner’s written consent to the dissent not later thanbefore or at the same time that the beneficial shareholderowner asserts dissenters'dissenters’ rights. (b) Submits(Last amended by P.A. 85-1269, eff. 1-1-89.).
      § 11.70.     Procedure to Dissent. (a) If the consent under par. (a)corporate action giving rise to the right to dissent is to be approved at a meeting of shareholders, the notice of meeting shall inform the shareholders of their right to dissent and the procedure to dissent. If, prior to the meeting, the corporation furnishes to the shareholders material information with respect to all shares of which he or she is the beneficial shareholder. History: 1989 a. 303. 180.1320 NOTICE OF DISSENTERS' RIGHTS. (1) If proposed corporate action creating dissenters' rights under a. 180.1302 is submitted to a vote at a shareholders' meeting, the meeting notice shall statetransaction that shareholders and beneficial shareholders are or may be entitled to assert dissenters' rights under ss. 180.1301 to 180.1331 and shall be accompanied by a copy of those sections. (2) If corporate action creating dissenters' rights under s. 180.1302 is authorized without a vote of shareholders, the corporation shall notify, in writing and in accordance with s. 180.0141, all shareholders entitled to assert dissenters' rights that the action was authorized and send them the dissenters' notice described in s. 180.1322. History: 1989 a. 303. 180.1321 NOTICE OF INTENT TO DEMAND PAYMENT. (1) If proposed corporate action creating dissenters' rights under s. 180.1302 is submitted to a vote at a shareholders' meeting,will objectively enable a shareholder to vote on the transaction and to determine whether or beneficialnot to exercise dissenters’ rights, a shareholder who wishes tomay assert dissenters'dissenters’ rights shall do all ofonly if the following: (a) Delivershareholder delivers to the issuer corporation before the vote is taken a written notice that complies with s. 180.0141 of the shareholder's or beneficial shareholder's intent to demand for payment for his or her shares if the proposed action is effectuated. (b) Notconsummated, and the shareholder does not vote his or her shares in favor of the proposed action. (2) A shareholder or beneficial shareholder who fails
      (b) If the corporate action giving rise to satisfy sub. (1)the right to dissent is not entitled to be approved at a meeting of shareholders, the notice to shareholders describing the action taken under Section 11.30 or Section 7.10

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shall inform the shareholders of their right to dissent and the procedure to dissent. If, prior to or concurrently with the notice, the corporation furnishes to the shareholders material information with respect to the transaction that will objectively enable a shareholder to determine whether or not to exercise dissenters’ rights, a shareholder may assert dissenter’s rights only if he or she delivers to the corporation within 30 days from the date of mailing the notice a written demand for payment for his or her shares under ss. 180.1301 to 180.1331. History: 1989 a. 303. 180.1322 DISSENTERS' NOTICE. (1) If proposed corporate action creating dissenters' rights under s. 180.1302 is authorized at a shareholders' meeting, the corporation shall deliver a written dissenters' notice to all shareholders and beneficial shareholders who satisfied s. 180.1321. (2) The dissenters' notice shall be sent no later thanshares.
      (c) Within 10 days after the corporate action is authorized at a shareholders' meeting or without a vote of shareholders, whichever is applicable. The dissenters' notice shall comply with s. 180.0141 and shall include or have attached all of the following: B-3 (a) A statement indicating where the shareholder or beneficial shareholder must send the payment demand and where and when certificates for certificated shares must be deposited. (b) For holders of uncertificated shares, an explanation of the extent to which transfer of the shares will be restricted after the payment demand is received. (c) A form for demanding payment that includes the date of the first announcement to news media or to shareholders of the terms of the proposed corporate action and that requires the shareholder or beneficial shareholder asserting dissenters' rights to certify whether he or she acquired beneficial ownership of the shares before that date. (d) A date by which the corporation must receive the payment demand, which may not be fewer than 30 days nor more than 60 days after the date on which the dissenters' noticecorporate action giving rise to the right to dissent is delivered. (e) A copy of ss. 180.1301effective or 30 days after the shareholder delivers to 180.1331. History: 1989 a. 303. 180.1323 DUTY TO DEMAND PAYMENT. (1) A shareholder or beneficial shareholder who is sent a dissenters' notice described in s. 180.1322, or a beneficial shareholder whose shares are held by a nominee who is sent a dissenters' notice described in s. 180.1322, must demand payment in writing and certify whether he or she acquired beneficial ownership of the shares beforecorporation the date specified in the dissenters' notice under s. 180.1322 (2) (c). A shareholder or beneficial shareholder with certificated shares must also deposit his or her certificates in accordance with the terms of the notice. (2) A shareholder or beneficial shareholder with certificated shares who demands payment and deposits his or her share certificates under sub. (1) retains all other rights of a shareholder or beneficial shareholder until these rights are canceled or modified by the effectuation of the corporate action. (3) A shareholder or beneficial shareholder with certificated or uncertificated shares who does not demand payment by the date set in the dissenters' notice, or a shareholder or beneficial shareholder with certificated shares who does not deposit his or her share certificates where required and by the date set in the dissenters' notice, is not entitled to payment for his or her shares under ss. 180.1301 to 180.1331. History: 1959 a. 303. 180.1324 RESTRICTIONS ON UNCERTIFICATED SHARES. (1) The issuer corporation may restrict the transfer of uncertificated shares from the date that thewritten demand for payment, for those shares is received until the corporate action is effectuated or the restrictions released under a. 180.1326. (2) The shareholder or beneficial shareholder who asserts dissenters' rights as to uncertificated shares retains all of the rights of a shareholder or beneficial shareholder, other than those restricted under sub. (1), until these rights are canceled or modified by the effectuation of the corporate action. History: 1989 a. 303. 180.1325 PAYMENT. (1) Except as provided in s. 180.1327, as soon as the corporate action is effectuated or upon receipt of a payment demand, whichever is later, the corporation shall paysend each shareholder or beneficial shareholder who has complied with s. 180.1323delivered a written demand for payment a statement setting forth the amount thatopinion of the corporation estimatesas to be the estimated fair value of his or herthe shares, plus accrued interest. (2) The payment shall be accompanied by all of the following: B-4 (a) The corporation'scorporation’s latest available financial statements, audited and including footnote disclosure if available, but including not less than a balance sheet as of the end of a fiscal year ending not moreearlier than 16 months before the datedelivery of payment, an incomethe statement, for that year, atogether with the statement of changes in shareholders' equityincome for that year and the latest available interim financial statements, if any. (b) A statementand either a commitment to pay for the shares of the corporation's estimatedissenting shareholder at the estimated fair value thereof upon transmittal to the corporation of the fair valuecertificate or certificates, or other evidence of ownership, with respect to the shares, or instructions to the dissenting shareholder to sell his or her shares within 10 days after delivery of the shares. (c) An explanation of howcorporation’s statement to the interest was calculated. (d) A statement ofshareholder. The corporation may instruct the dissenter's rightshareholder to demand payment under s. 180.1328sell only if there is a public market for the dissenter is dissatisfied withshares at which the payment. (e) A copy of ss. 180.1301 to 180.1331. History: 1989 a. 303. 180.1326 FAILURE TO TAKE ACTION. (1)shares may be readily sold. If an issuer corporationthe shareholder does not effectuate the corporate actionsell within 60 daysthat 10 day period after the date set under s. 180.1322 for demanding payment, the issuer corporation shall return the deposited certificates and release the transfer restrictions imposed on uncertificated shares. (2) If after returning deposited certificates and releasing transfer restrictions, the issuer corporation effectuates the corporate action,being so instructed by the corporation, for purposes of this Section the shareholder shall deliver a new dissenters' notice under s. 180.1322 and repeatbe deemed to have sold his or her shares at the payment demand procedure. History: 1989 a. 303. 180.1327 AFTER-ACQUIRED SHARES. (1) A corporation may elect to withhold payment required by s. 180.1325 from a dissenter unless the dissenter was the beneficial owneraverage closing price of the shares, beforeif listed on a national exchange, or the date specified in the dissenters' notice under s. 180.1322 (2)(c) as the dateaverage of the first announcementbid and asked price with respect to news mediathe shares quoted by a principal market maker, if not listed on a national exchange, during that 10 day period.
      (d) A shareholder who makes written demand for payment under this Section retains all other rights of a shareholder until those rights are cancelled or to shareholders ofmodified by the termsconsummation of the proposed corporate action. (2) To the extentUpon consummation of that action, the corporation electsshall pay to withhold payment under sub. (1) after effectuatingeach dissenter who transmits to the corporate action, it shall estimatecorporation the certificate or other evidence of ownership of the shares the amount the corporation estimates to be the fair value of the shares, plus accrued interest, and shall pay this amount to each dissenter who agrees to accept it in full satisfaction of his or her demand. The corporation shall send with its offeraccompanied by a statement of its estimate of the fair value of the shares, anwritten explanation of how the interest was calculated, and acalculated.
      (e) If the shareholder does not agree with the opinion of the corporation as to the estimated fair value of the shares or the amount of interest due, the shareholder, within 30 days from the delivery of the corporation’s statement of the dissenter's right to demand payment under s. 180.1328 if the dissenter is dissatisfied with the offer. History: 1989 a. 303. 180.1328 PROCEDURE IF DISSENTER DISSATISFIED WITH PAYMENT OR OFFER. (1) A dissenter may, in the manner provided in sub. (2),value, shall notify the corporation in writing of the dissenter's estimate of theshareholder’s estimated fair value of his or her shares and amount of interest due and demand payment for the difference between the shareholder’s estimate of hisfair value and interest due and the amount of the payment by the corporation or herthe proceeds of sale by the shareholder, whichever is applicable because of the procedure for which the corporation opted pursuant to subsection (c).
      (f) If, within 60 days from delivery to the corporation of the shareholder notification of estimate less any payment received under s. 180.1325, or rejectof fair value of the offer under s. 180.1327shares and demand payment ofinterest due, the corporation and the dissenting shareholder have not agreed in writing upon the fair value of his or herthe shares and interest due, if any of the following applies: (a) The dissenter believes that the amount paid under s. 180.1325 or offered under s. 180.1327 is less than the fair value of his or her shares or that the interest due is incorrectly calculated. (b) The corporation fails to make payment under s. 180.1325 within 60 days after the date set under s. 180.1322 for demanding payment. B-5 (c) The issuer corporation, having failed to effectuate the corporate action, does not return the deposited certificates or release the transfer restrictions imposed on uncertificated shares within 60 days after the date set under s. 180.1322 for demanding payment. (2) A dissenter waives his or her right to demand payment under this section unless the dissenter notifies the corporation of his or her demand under sub. (1) in writing within 30 days after the corporation made or offered payment for his or her shares. The notice shall comply with s. 180.0141. History: 1989 a. 303. 180.1329 COURT ACTION. (1) If a demand for payment under s. 180.1328 remains unsettled, the corporation shall bringeither pay the difference in value demanded by the shareholder, with interest, or file a special proceeding within 60 days after receivingpetition in the payment demand under s. 180.1328 and petitioncircuit court of the county in which either the registered office or the principal office of the corporation is located, requesting the court to determine the fair value of the shares and accrued interest. If the corporation does not bring the special proceeding within the 60-day period, it shall pay each dissenter whose demand remains unsettled the amount demanded. (2) The corporation shall bring the special proceeding in the circuit court for the county where its principal office or, if none in this state, its registered office is located. If the Corporation is a foreign corporation without a registered office in this state, it shall bring the special proceeding in the county in this state in which was located the registered office of the issuer corporation that merged with or whose shares were acquired by the foreign corporation. (3)interest due. The corporation shall make all dissenters, whether or not residents of this state,State, whose demands remain unsettled parties to the special proceeding. Each party to the special proceeding as an action against their shares and all parties shall be served with a copy of the petitionpetition. Nonresidents may be served by registered or certified mail or by publication as provided in s. 801.14. (4)by law. Failure of the corporation to commence an action pursuant to this Section shall not limit or affect the right of the dissenting shareholders to otherwise commence an action as permitted by law.
      (g) The jurisdiction of the court in which the special proceeding is broughtcommenced under sub. (2)subsection (f) by a corporation is plenary and exclusive. The court may appoint one or more persons as appraisers to receive evidence and recommend decision on the question of fair value. An appraiser hasThe appraisers have the power described in the order appointing him or herthem, or in any amendment to the order. The dissenters are entitled to the same discovery rights as parties in other civil proceedings. (5)it.

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      (h) Each dissenter made a party to the special proceeding is entitled to judgment for any of the following: (a) The amount, if any, by which the court finds that the fair value of his or her shares, plus interest, exceeds the amount paid by the corporation. (b)corporation or the proceeds of sale by the shareholder, whichever amount is applicable.
      (i) The fair value, plus accrued interest, of his or her shares acquired on or after the date specified in the dissenter's notice under s. 180.1322 (2)(c), for which the corporation elected to withhold payment under s. 180.1327. History: 1989 a. 303. Because this section does not provide for different procedures, all procedural mechanisms under chs. 801 to 847 are available in an action under this section. Kohler Co. v. Sogen International Fund, Inc. 2000 WI App 60, 233 Wis. 2d 592, 608 N.W.2d 746. 180.1330 COURT COSTS AND COUNSEL FEES. (1) (a) Notwithstanding ss. 814.01 to 814.04, the court, in a special proceeding broughtcommenced under s. 180.1330subsection (f), shall determine all costs of the proceeding, including the reasonable compensation and expenses of the appraisers, if any, appointed by the court under subsection (g), but shall exclude the fees and shall assessexpenses of counsel and experts for the respective parties. If the fair value of the shares as determined by the court materially exceeds the amount which the corporation estimated to be the fair value of the shares or if no estimate was made in accordance with subsection (c), then all or any part of the costs may be assessed against the corporation, exceptcorporation. If the amount which any dissenter estimated to be the fair value of the shares materially exceeds the fair value of the shares as provided in par. (b). B-6 (b) Notwithstanding ss. 814.01 and 814.04,determined by the court, may assess costs againstthen all or someany part of the dissenters, in amountscosts may be assessed against that the court finds to be equitable, to the extent that the court finds the dissenters acted arbitrarily, vexatiously or not in good faith in demanding payment under s. 180.1328. (2)dissenter. The parties shall bear their own expenses of the proceeding, except that, notwithstanding ss. 814.01 to 814.04, the court may also assess the fees and expenses of counsel and experts for the respective parties, in amounts that the court finds to be equitable, as follows: (a) Against the corporation and in favor of any dissenter if the court finds that the corporation did not substantially comply with ss. 180.1320 to 180.1328. (b) Against the corporation or against a dissenter, in favor of any other party, if the court finds that the party against whom the fees and expenses are assessed acted arbitrarily, vexatiously or not in good faith with respect to the rights provided by this chapter. (3) Notwithstanding ss. 814.01 to 814.04,
      (1) Against the corporation and in favor of any or all dissenters if the court finds that the corporation did not substantially comply with the requirements of subsections (a), (b), (c), (d), or (f).
      (2) Against either the corporation or a dissenter and in favor of any other party if the court finds that the party against whom the fees and expenses are assessed acted arbitrarily, vexatiously, or not in good faith with respect to the rights provided by this Section.
If the court finds that the services of counsel and experts for any dissenter were of substantial benefit to other dissenters similarly situated and that the fees for those services should not be assessed against the corporation, the court may award to thesethat counsel and experts reasonable fees to be paid out of the amounts awarded to the dissenters who wereare benefited. History: 1989 a. 303. ANNEXExcept as otherwise provided in this Section, the practice, procedure, judgment and costs shall be governed by the Code of Civil Procedure.
      (j) As used in this Section:
      (1) “Fair value”, with respect to a dissenter’s shares, means the value of the shares immediately before the consummation of the corporate action to which the dissenter objects excluding any appreciation or depreciation in anticipation of the corporate action, unless exclusion would be inequitable.
      (2) “Interest” means interest from the effective date of the corporate action until the date of payment, at the average rate currently paid by the corporation on its principal bank loans or, if none, at a rate that is fair and equitable under all the circumstances. (Last amended by P.A. 86-1156, eff. 8-10-90.)

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Annex C FORM OF VOTING AGREEMENT
Voting Agreement
This Agreement ("Agreement"(“Agreement”) is made and entered into as of the ___5th day of June, 2004,December, 2005, by and between the undersigned stockholdersshareholders (each, a "Stockholder," “Shareholder,”and collectively, the "Stockholders") of Town Bankshares, Ltd., a Wisconsin corporation (the "Company"“Shareholders”), and Wintrust Financial Corporation,ofHinsbrook Bancshares, Inc., an Illinois corporation ("Wintrust"(the“COMPANY”). W I T N E S S E T H: WHEREAS, the Company, andWintrust are enteringFinancial Corporation, an Illinois corporation(“WINTRUST”).
Witnesseth:
Whereas, theCompany andWintrust have entered into an Agreement and Plan of Merger simultaneously herewithdated as of the date hereof (the "Merger Agreement"“Merger Agreement”) (capitalized terms used but not defined in this Agreement shall have the meanings given them in the Merger Agreement); WHEREAS,
Whereas, each of the Shareholders is a director or executive officer of the Company or its wholly owned subsidiary, Hinsbrook Bank & Trust;
Whereas, it is a condition precedent to the willingness of Wintrust to enter intoWintrust’s obligations under the Merger Agreement that the StockholdersShareholders shall have executed and delivered this Agreement;Agreement, solely in their capacities as shareholders of the Company; and WHEREAS,
Whereas, each StockholderShareholder owns and is entitled to vote the number of issued and outstanding shares of common stock of the Company (the "Company“Company Common Shares"Shares”) set forth opposite such Stockholder'sShareholder’s name on Schedule 1 attached hereto and has agreed to vote such Stockholder'sShareholder’s Company Common Shares pursuant to the terms set forth in this Agreement. NOW, THEREFORE,
Now,Therefore, in consideration of the premises and the respective representations, warranties, covenants and agreements set forth herein, the StockholdersShareholders and Wintrust hereby agree as follows:
Section 1.     Voting of Shares. Each StockholderShareholder hereby agrees that at any meeting of the stockholdersshareholders of the Company and in any action by written consent of the stockholdersshareholders of the Company, such StockholderShareholder shall vote the Company Common Shares which such StockholderShareholder owns and is entitled to vote (a) in favor of the transactions contemplated by the Merger Agreement, (b) against any action or agreement which would result in a breach of any term of, or any other obligation of the Company under, the Merger Agreement, and (c) against any action or agreement which would impede, interfere with or attempt to discourage the transactions contemplated by the Merger Agreement;provided,however, that nothing in this Agreement shall prevent a Stockholder,Shareholder, in his or her capacity as a director of the Company, from discharging his or her fiduciary dutyduties to the Company.Company nor shall anything in this Agreement prevent a Shareholder who is an officer of the Company from acting in his or her capacity as such. Each StockholderShareholder agrees that the Company shall be authorized to include in any proxy or material transmitted to stockholdersshareholders of the Company, a statement to the effect that the StockholderShareholder is a party to this Agreement and has committed to vote in favor of the transactions contemplated by the Merger Agreement.
Section 2.     Term of Agreement. This Agreement shall be effective from the date hereof and shall terminate and be of no further force and effect upon the earlier of (i) the Effective Time (as defined in the Merger Agreement), or (ii) the termination of the Merger Agreement in accordance with its terms. terms, which includes termination in the event the Company Board determines that its fiduciary duties require it to accept an unsolicited Superior Acquisition Proposal from a third party pursuant to Section 5.8(b) of the Merger Agreement.
Section 3.     Covenants of Stockholders.Shareholders. Each StockholderShareholder agrees not to: except to the extent contained in this Agreement, grant any proxies, deposit any Company Common Shares into a voting trust or enter into a voting agreement with respect to any of the Company Common Shares; or without the prior

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written approval of Wintrust, solicit, initiate or encourage any inquiries or proposals for a merger or other business combination involving the Company; provided, however, that nothing in this Agreement shall prevent a Stockholder, in his or her capacity as a director of the Company, from discharging his or her fiduciary duty to the Company.
Section 4.     Representations and Warranties of Stockholders.Shareholders. Each StockholderShareholder represents and warrants to Wintrust as follows: (a) such StockholderShareholder owns, and is entitled to vote in accordance with such Stockholder'sShareholder’s commitments under this Agreement, the number of Company Common Shares set forth opposite his or her name on Schedule 1 hereto, and, except for options to acquire Company Common Shares listedas disclosed on Schedule 1 as being held by such Stockholder,3.3(a) of the Merger Agreement, does not own or have any right to acquire any other Company Common Shares;Shares not listed on Schedule 1; (b) such StockholderShareholder has the right, power and authority to execute, deliver and perform under this Agreement; such execution, delivery and performance will not violate, or require any consent, approval, or notice under any provision of law or result in the breach of any outstanding agreements or instruments to which such StockholderShareholder is a party or is subject; and this Agreement has been duly executed and delivered by such StockholderShareholder and constitutes a legal, valid C-1 and binding agreement of such Stockholder,Shareholder, enforceable in accordance with its terms; (c) except as set forth in the next sentence, such Stockholder's Company Common Shares and options to acquireShareholder’s Company Common Shares listed as owned or held on Schedule 1 hereto are now and will remain owned or held by such Stockholder,Shareholder, free and clear of all voting trusts, voting agreements, proxies, liens, claims, liabilities, security interests, marital property rights or any other encumbrances whatsoever (other than (i) pledges for loans entered into in the ordinary course (ii) pursuant to a transfer where the transferee has agreed in writing to be bound by the terms of this Agreement, (iii) transfers by will or operation of law, (iv) marital property rights under applicable law that do not adversely affect Wintrust's rights or remedies under this Agreement, and (v)(ii) rights of Wintrust and encumbrances respecting such Company Common Shares created pursuant to this Agreement or the Merger Agreement); and (d) other than this Agreement and the Merger Agreement, there are no outstanding options, warrants or rights to purchase or acquire, or agreements related to, such Stockholder'sShareholder’s Company Common Shares. Notwithstanding anything contained in this Agreement to the contrary, at any time prior to the Closing, each Shareholder shall be permitted to transfer ownership and voting rights of any or all of such Shareholder’s Company Common Shares listed as owned on Schedule 1 without obtaining Wintrust’s prior consent or approval of such transfer provided that any such transferee agrees to be bound by the terms, conditions and obligations of this Agreement in writing by an instrument or agreement satisfactory in form to Wintrust.
Section 5.     Representations and Warranties of Wintrust. Wintrust has the right, power and authority to execute and deliver this Agreement; such execution and delivery will not violate, or require any consent, approval, or notice under any provision of law or result in the breach of any outstanding agreements or instruments to which Wintrust is a party or is subject; and this Agreement has been duly executed and delivered by Wintrust and constitutes a legal, valid and binding agreement of Wintrust, enforceable in accordance with its terms.
Section 6.     Transferability. Except as provided herein, neither Neither this Agreement nor any of the rights, interests or obligations hereunder shall be assigned by any of the parties hereto (whether by operation of law or otherwise) without the prior written consent of the other parties, except that Wintrust may assign this Agreement to a direct or indirect wholly-owned subsidiary or affiliate of Wintrust,provided that no such assignment shall relieve Wintrust of its obligations hereunder.
Section 7.     Specific Performance. The parties hereto agree that irreparable damage would occur in the event that any of the provisions of this Agreement was not performed by any of the StockholdersShareholders in accordance with its specific terms or was otherwise breached. It is accordingly agreed that Wintrust shall be entitled to an injunction(s) to prevent breaches of this Agreement by the StockholdersShareholders and to enforce specifically the terms and provisions hereof in addition to any other remedy to which Wintrust is entitled at law or in equity.
Section 8.     Further Assurances. Each StockholderShareholder agrees to execute and deliver all such further documents and instruments and take all such further action as may be necessary or appropriate in order to consummate the transactions contemplated hereby.
Section 9.     Entire Agreement and Amendment. (a) Except for the Merger Agreement and its ancillary agreements and instruments, this Agreement contains the entire agreement between the parties hereto with respect to the transactions contemplated hereunder and supersedes all prior arrangements or understandings with respect hereto.

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      (b) This Agreement may not be modified, amended, altered or supplemented except upon the execution and delivery of a written agreement executed by the parties hereto.
Section 10.     Notices. Each notice, demand or other communication which may be or is required to be given under this Agreement shall be in writing and shall be deemed to have been properly given when delivered personally at the address set forth herein for Wintrust or the address on Schedule 1 for each of the Stockholders,Shareholders, when sent by facsimile or other electronic transmission to the respective facsimile transmission numbers of the parties with telephone confirmation of receipt, or the day after sending by recognized overnight courier or if by the United States registered or certified mail, return receipt requested, postage prepaid two days after deposit therein.
Section 11.     General Provisions. This Agreement shall be governed by the laws of the State of Illinois. This Agreement may be executed in counterparts, each of which shall be deemed to be an original. Headings are for convenience only and shall not affect the meaning of this Agreement. Any term of this Agreement which is invalid or unenforceable shall be ineffective only to the extent of such invalidity or unenforceability without rendering invalid or unenforceable the remaining terms of this Agreement. [SIGNATURE PAGE FOLLOWS] C-2 IN WITNESS WHEREOF,

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In Witness Whereof, the parties hereto have executed this Agreement as of the day and year first above written. WINTRUST FINANCIAL CORPORATION, an Illinois Corporation By: --------------------------- Its: --------------------------- Address for Notices: With a copy to: Wintrust Financial Corporation Schiff Hardin LLP 727 North Bank Lane 6600 Sears Tower Lake Forest, Illinois 60045 Chicago, Illinois 60606-6473 Attn: David A. Dykstra Attn: Matthew G. Galo Senior Executive Vice President and Chief Operating Officer Facsimile No.: (847) 615-4091 Facsimile No.: (312) 258-5700 Stockholders: - ------------------------------- ------------------------------- William J. Hickmann Fred A. Orlando - ------------------------------- ------------------------------- Roger L. Jensen Janet L. F. Phillips - ------------------------------- ------------------------------- Jay C. Mack Michael J. Petrasky, Sr. - ------------------------------- ------------------------------- Thomas Manthy Randall R. Tiedt - ------------------------------- ------------------------------- Jeffrey Olsen Robert N. Trunzo C-3 SCHEDULE 1
NUMBER OF COMPANY COMMON SHARES NAME, ADDRESS AND FACSIMILE NUMBER NUMBER OF COMPANY COMMON SHARES ISSUABLE UNDER OPTIONS HELD BY OF STOCKHOLDER OWNED BY STOCKHOLDER STOCKHOLDER - ---------------------------------- ------------------------------- ------------------------------ William J. Hickmann 10,606 5,000 Hickmann & Hickmann S.C. 2125 West Washington Street West Bend, WI 53095-2205 262-306-2880 Roger
Wintrust Financial Corporation, an Illinois Corporation:
By: /s/ David A. Dykstra
Its:Senior Executive Vice President and
Chief Operating Officer
Address for Notices:With a copy to
Wintrust Financial Corporation  Matthew G. Galo
727 North Bank Lane  Schiff Hardin LLP
Lake Forest, Illinois 60045  6600 Sears Tower
Attn: David A. Dykstra  Chicago, Illinois 60606-6473
Senior Executive Vice President and
Chief Operating Officer
Facsimile No.: (847) 615-4091  Facsimile No.: (312) 258-5700
[SHAREHOLDER SIGNATURE PAGES FOLLOW]

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/s/ Neal A. Anderson
Neal A. Anderson, individually and as Trustee
Acknowledged by:
/s/ Madeline L. Jensen 2,210 3,000 Town Bankshares, Ltd. 400 Genesee Street Delafield, WI 53018 262-646-6889 Jay C. Mack 3,153 8,500 Town Bankshares, Ltd. 400 Genesee Street Delafield, WI 53018 262-646-6889Anderson
Madeleine L. Anderson, as Trustee
/s/ Robert K. Buhrke
Robert K. Buhrke, individually and as Trustee
Acknowledged by:
Hinsbrook Bank and Trust, as Trustee of the
     Hinsbrook Bank and Trust 401(k) Plan

By: /s/ John H. Lohmeier
Name: John H. Lohmeier
Title:Senior Vice President
/s/ Geraldine K. Buhrke
Geraldine K. Buhrke, as Trustee
/s/ Jeffrey D. Baker
Jeffrey D. Baker
Acknowledged by:
/s/ Gregory R. Baker
Gregory R. Baker, as custodian

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/s/ Andrew M. Collins
Andrew M. Collins
Acknowledged by:
Hinsbrook Bank and Trust, as Trustee of the
     Hinsbrook Bank and Trust 401(k) Plan

By: /s/ John H. Lohmeier
Name: John H. Lohmeier
Title:Senior Vice President
/s/ Margaret M. Collins
Margaret M. Collins
/s/ James R. Hannon
James R. Hannon
Acknowledged by:
Hinsbrook Bank and Trust, as Trustee of the
     Hinsbrook Bank and Trust 401(k) Plan
By: /s/ John H. Lohmeier
Name: John H. Lohmeier
Title:Senior Vice President
/s/ Gail Hannon
Gail Hannon
/s/ L. Thomas A. Manthy 7,043 3,000 2865 North River Birch #B Brookfield, WI 53045 262-567-8710McNamara
L. Thomas McNamara

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Acknowledged by:
Hinsbrook Bank and Trust, as Trustee of the
     Hinsbrook Bank and Trust 401(k) Plan

By: /s/ John H. Lohmeier
Name: John H. Lohmeier
Title:Senior Vice President
/s/ Margaret McNamara
Margaret McNamara
/s/ Daniel Regan
Daniel Regan
Acknowledged by:
Hinsbrook Bank and Trust, as Trustee of the
     Hinsbrook Bank and Trust 401(k) Plan
By: /s/ John H. Lohmeier
Name: John H. Lohmeier
Title:Senior Vice President
/s/ Barbara Regan
Barbara Regan
/s/ Ying-Yih Wu
Ying-Yih Wu

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Acknowledged by:
Wu Med Center

By: /s/ Ying-Yih Wu
Name: Ying-Yih Wu
Title:Trustee
/s/ Regina Miller
Regina Miller
Acknowledged by:
/s/ Robert Miller
Robert Miller
/s/ John H. Lohmeier
John H. Lohmeier
Acknowledged by:
Hinsbrook Bank and Trust, as Custodian
By: /s/ Jeffrey A. Olsen 1,500 4,700 Town Bankshares, Ltd. 400 Genesee Street Delafield, WI 53018 262-646-6889 Fred A. Orlando 4,376 3,000 Town Bankshares, Ltd. 400 Genesee Street Delafield, WI 53018 262-646-6889 Janet L.F. Phillips 4,563 3,000 632 Glenview Avenue Oconomowoc, WI 53066 262-569-7890 Michael J. Pretasky, Sr. 11,781 3,000 Skipper Marine Holdings, Inc. 1030 Silvernail Road Pewaukee, WI 53072 262-544-1030 Randall R. Tiedt 400 1,200 Town Bankshares, Ltd. 400 Genesee Street Delafield, WI 53018 262-646-6889 C-4 NUMBER OF COMPANY COMMON SHARES NAME, ADDRESS AND FACSIMILE NUMBER NUMBER OF COMPANY COMMON SHARES ISSUABLE UNDER OPTIONS HELD BY OF STOCKHOLDER OWNED BY STOCKHOLDER STOCKHOLDER - ---------------------------------- ------------------------------- ------------------------------ Robert N. Trunzo 4,726 3,000 Frank F. Haack & Associates, Inc. 2323 North Mayfair Road, #600 P.O. Box 26997 Milwaukee, WI 53226-0997 414-259-8778 D. Baker
ANNEX
Name: Jeffrey D. Baker
Title:Executive Vice President

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Schedule 1
         
    Number of
    Company Common
  Number of Company Shares Issuable
  Common Shares Under Options
Name, Address and Facsimile Number of Shareholder(1) Owned by Shareholder Held by Shareholder
     
Neal A. Anderson  141,500   0 
Robert K. Buhrke  159,377   0 
Jeffrey D. Baker  7,363   0 
Andrew M. Collins, Jr.   95,316   0 
James R. Hannon  170,969   0 
John Lohmeier  27,737   0 
L. Thomas McNamara  80,586   0 
Regina R. Miller  10,222   0 
Daniel Regan  214,784   0 
Ying-Yih Wu  180,182   0 
(1) The address and facsimile number for each shareholder is c/o Hinsbrook Bank and Trust, 6262 S. Route 83, Willowbrook, Illinois 60527, facsimile number (630) 321-5290.

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Annex D [LETTERHEAD OF EDELMAN & CO., LTD.] June 14, 2004
December 5, 2005
Board of Directors Town Bankshares, Ltd. 400 Genesee St. Delafield, WI 53018 Gentlemen: We understand that Town Bankshares, Ltd. ("TBL") and Wintrust Financial Corporation ("WTFC") have entered into an Agreement and Plan of Merger ("the Agreement"), providing for the merger of TBL with and into WTFC (the "Merger"). The Agreement provides for shares of common stock, $.01 par value per share, of TBL ("TBL Common Stock"), other than shares held by the Employee Stock Ownership Plan of TBL which are to be redeemed for cash, to be converted into the right to receive a combination of cash and shares of WTFC common stock, no par value ("WTFC Common Stock"), having an aggregate value of $129.10 (the "Consideration"). The terms and conditions
Hinsbrook Bancshares, Inc.
6262 S. Route 83
Willowbrook, IL 60527
Members of the Merger, including but not limited to provisions concerning the number of WTFC shares to be issued with respect to TBL shares, and allowing the parties to terminate the Agreement based on trading levels of WTFC shares (the "Termination Right"), are more fully described in the Agreement.Board:
      You have requested our opinion as to the fairness, from a financial point of view, of the consideration to be received by the common shareholders of TBL,Hinsbrook Bancshares, Inc. (the “Company”) pursuant to an Agreement and Plan of Merger to be dated December 5, 2005 (the “Agreement”) by and between the Company and Wintrust Financial Corporation (“Buyer”). At the Effective Time, as defined in the Agreement, the Company will be merged with and into Buyer (the “Merger”) and each share of the Consideration.Company’s common stock, par value $0.05 per share (the “Company Common Stock”), held by the Company’s shareholders shall be converted into the right to receive consideration (the “Merger Consideration”) consisting of a cash amount equal to $41.59 per share or a fractional amount of a share of Buyer’s common stock (the “Buyer Common Stock”) equal to a value of $41.59 at the time of closing subject to certain adjustments as provided in the Agreement. The Agreement provides that the total consideration shall be comprised of 50% cash and 50% Buyer Common Stock and that Company shareholder requests for cash or stock will be prorated to assure that the Merger Consideration actually paid by Buyer consists of cash and Buyer Common Stock in such proportions. The complete terms of the proposed transaction are described in the Agreement, and this summary is qualified in its entirety by reference thereto.
      Capital Market Securities, Inc. as part of its business is regularly engaged in the valuation of businesses and their securities in connection with mergers and acquisitions and valuations for corporate and other purposes. We are familiar with the market for equity securities of publicly traded financial institutions. We are acting as financial advisor to the Company in connection with the Merger and will receive a fee for our services, a significant portion of which is payable upon the consummation of the Merger and a portion of which is payable in connection with this opinion.
      In formingarriving at our opinion, we have, reviewed, among other things, (i) with respect to WTFC, Annual Reports on Form 10-K and Annual Reports to Shareholders for the fiscal years ended December 31, 1999 through 2003, and the Quarterly Report on Form 10-Q for the quarter ended March 31, 2004; (ii) with respect to TBL, audited financial statements for the fiscal years ended December 31, 1999 through 2003, and the unaudited internal balance sheet and income statement, provided by TBL, for the quarter ended March 31, 2004; (iii) the Agreement; (iv) certain other information concerning the future prospects of WTFC and TBL, and of the combined entity, as furnished by the respective companies, which we discussed with the senior management of WTFC and TBL; (v) historical market price and trading data for WTFC Common Stock and, as provided by TBL, for TBL Common Stock; (vi) the financial performance and condition of WTFC and TBL and similar data for other financial institutions which we believed to be relevant; (vii) the financial terms of other mergers which we believed to be relevant; and (viii) such other information as we deemed appropriate. We met with certain senior officers of WTFC and TBL to discuss the foregoing as well as other matters relevant to our opinion, including the past and current business operations, financial condition and future prospects of WTFC and TBL. We also took into account our assessment of general economic, market and financial conditions, and such additional financial and other factors as we deemed relevant.things:
      (i) reviewed the draft form of the Agreement dated December 5, 2005;
      (ii) reviewed certain historical financial and other information concerning the Company for the five fiscal years ended December 31, 2004 and unaudited financial information for the quarters ended March 31, 2005, June 30, 2005 and September 30, 2005;
      (iii) reviewed certain historical financial and other information concerning Buyer for the five fiscal years ended December 31, 2004 and unaudited financial information for the quarters ended March 31, 2005, June 30, 2005 and September 30, 2005;
      (iv) held discussions with the senior management of the Company and Buyer with respect to their past and current financial performance, financial condition and future prospects;
      (v) reviewed certain internal financial data, projections and other information of the Company and Buyer;
      (vi) analyzed certain publicly available information of other financial institutions that we deemed comparable or otherwise relevant to our inquiry, and compared the Company and Buyer from a financial point of view with certain of these institutions;

D-1


      (vii) compared the Merger Consideration to be received by the shareholders of the Company with the consideration received by shareholders in other acquisitions of financial institutions that we deemed comparable or otherwise relevant to our inquiry;
      (viii) reviewed historical trading activity and ownership data of Buyer Common Stock and considered the prospects for dividends and price movement;
      (ix) reviewed historical trading activity and ownership data of the Company Common Stock and considered the prospects for dividends and market pricing; and
      (x) conducted such other financial studies, analyses and investigations and reviewed such other information as we deemed appropriate to enable us to render our opinion. In our review, we have also taken into account an assessment of general economic, market and financial conditions and certain industry trends and related matters.
      In conducting our review and preparinganalysis and in arriving at our opinion we have assumed and relied upon the accuracy and completeness of the publicly-available financial and other information usedthat we have reviewed relating to the Company and Buyer and the internal financial and other information and data provided to us by us without independently verifyingthe Company and Buyer and have not attempted to verify any of such informationinformation. We have assumed (i) that the forecasts prepared with respect to the results of operations likely to be achieved represent a reasonable estimate as to future financial performance and results and (ii) that such forecasts and estimates will be realized in the amounts and in the time periods projected. We have further relied uponon the assurances of management of WTFCBuyer and TBLthe Company that they are not aware of any facts or circumstances that would make such information misleadinginaccurate or inaccurate.misleading. We have also relied upon the accuracy and completeness of the representations, warranties and covenants of D-1 Board of Directors Town Bancshares, Ltd. June 14, 2004 TBL and WTFC contained in the Agreement. We relied upon the management of WTFC and TBL in forming a view of the future prospects of WTFC and TBL, and in forming assumptions regarding a variety of matters. We assumed, without independent verification, that the allowancesaggregate reserves for possible loan losses at WTFCfor the Company and TBL wereBuyer are adequate to cover such losses. We did not inspect any properties, assets or liabilities of WTFC or TBL and did not make or obtain any independent evaluations or appraisals of any properties, assets or liabilities of WTFCthe Company, Buyer or TBL.any of their respective subsidiaries nor did we verify any of the Company’s or Buyer’s books or records or review any individual loan credit files. Our opinion does not address the relative merits of the Merger as compared to other business strategies or transactions that might be available to the Company or the Company’s underlying business decision to effect the Merger. We express no opinion as to what the value of Buyer Common Stock actually will be when issued pursuant to the Merger or the price at which Buyer Common Stock will trade at any time.
      Our opinion is necessarily based upon market, economic, monetary and other conditions as they exist and can be evaluated as of the date of this letter. It should be understood that subsequent developments may affect this opinion and that we do not have any obligation to update, revise or reaffirm this opinion. In rendering our opinion, we have assumed that in the course of obtaining the necessary approvals for the Merger, no restrictions or conditions will be consummatedimposed that would have a material adverse effect on the terms described in the Agreement in the absence of circumstances creating a Termination Right on the part of TBL, that all conditions to consummationcontemplated benefits of the Merger set forth into Buyer or the Agreement will be satisfied,ability to consummate the Merger and that the Merger will be consummated on a timely basis. Our engagement andin accordance with the opinion expressed herein are for the benefitterms of the TBLAgreement in the form of the draft that we have reviewed without waiver, modification or amendment of any material term or condition. This opinion is being directed to the Board of Directors. Our opinion is directed solely to the fairness, from a financial point of view,Directors of the Consideration,Company and doesis not address the decision to effect the Merger or constitute a recommendation to any TBL shareholder as to how such shareholder should vote onwith respect to the Merger. In addition, you have not asked us to address, and this opinion does not address, the fairness to, or any other consideration of, the holders of any class of securities, creditors or constituencies of the Company, other than the holders of the Company Common Stock. This opinion may be included in its entirety in the proxy statement of the Company used to solicit shareholder approval of the Merger, provided that this opinion is reproduced in full and any description of or reference to us or summary of this opinion and the related analysis in such filing is in a form reasonably acceptable to us and our counsel, but may not be otherwise quoted, communicated or reproduced and distributed, in whole or in part without our prior written approval. We are expressingexpress no opinion on matters of a legal, regulatory, tax or accounting nature. It is further understoodnature or the ability of the Merger, as set forth in the Agreement in the form of the draft that our opinion is based on economic and market conditions and other circumstances existing at the time we renderhave reviewed, to be consummated. In furnishing this opinion, on June 14, 2004. Wewe do not admit that we are not expressing any“experts” within the meaning of that term under the Securities Act of 1933, as amended, and the rules and regulations promulgated thereunder, nor do we admit that this opinion onconstitutes a report or valuation within the valuemeaning of WTFC Common Stock or the impact that the Merger will have on the valueSection 11 of WTFC Common Stock in the future, or on an appropriate course of action by you should circumstances give rise to a Termination Right on the part of TBL. TBL has agreed to indemnify us for certain liabilities arising out of our engagement by TBL in connection with the Merger. It is understood that, except for inclusion in full in the Proxy Statement/Prospectus relating to the Merger, this letter may not be disclosed or otherwise referred to without our prior written consent, which will not be unreasonably withheld, except as may otherwise be required by law or by a court of competent jurisdiction. This Opinion is rendered solely to you in your capacity as directors of TBL and may not be relied on by you in any other capacity or by any other person without our express written consent.such Act.

D-2


      Based onupon and subject to the foregoing, and such other factors as we deem relevant, we are of theit is our opinion that as of the date hereof that the Merger Consideration to be received by holders of the Company Common Stock is fair to such holders from a financial point of view, to the holdersview.
Very truly yours,
/s/ Capital Market Securities, Inc.
Capital Market Securities, Inc.

D-3


PART II
Information Not Required in Prospectus
Item 20. Indemnification of TBL Common Stock. Sincerely, /s/ Edelman & Co., Ltd. Edelman & Co., Ltd. D-2 PART II INFORMATION NOT REQUIRED IN PROSPECTUS ITEM 20. INDEMNIFICATION OF OFFICERS AND DIRECTORS.Officers and Directors.
     In accordance with the Illinois Business Corporation Act (being Chapter 805, Act 5 of the Illinois Compiled Statutes), Articles Eight and Nine of the Registrant's CertificateRegistrant’s Articles of Incorporation provide as follows:
ARTICLE EIGHT:EIGHT: No director of the corporation shall be liable to the corporation or its shareholders for monetary damages for breach of fiduciary duty as a director except for liability (a) for any breach of the director'sdirector’s duty of loyalty to the corporation or its shareholders, (b) for acts or omissions not in good faith or that involve intentional misconduct of a knowing violation of law, (c) under Section 8.65 of the BCA, as the same exists or hereafter may be amended, or (d) for any transaction from which the director derived an improper personal benefit.
ARTICLE NINE, PARAGRAPH 1:Paragraph 1: The corporation shall indemnify, to the full extent that it shall have power under applicable law to do so and in a manner permitted by such law, any person made or threatened to be made a party to any threatened, pending or completed action, suit or proceeding, whether civil, criminal, administrative or investigative, by reason of the fact that he or she is or was a director, officer, employee or agent of the corporation, or who is or was serving at the request of the corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise against liabilities and expenses reasonably incurred or paid by such person in connection with such action, suit or proceeding. The corporation may indemnify, to the full extent that it shall have power under applicable law to do so and in a manner permitted by such law, any person made or threatened to be made a party to any threatened, pending or completed action, suit or proceeding, whether civil, criminal, administrative or investigative, by reason of the fact that he or she is or was a director, officer, employee or agent of the corporation, or is or was serving at the request of the corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise against liabilities and expenses reasonably incurred or paid by such person in connection with such action, suit or proceeding. The words "liabilities"“liabilities” and "expenses"“expenses” shall include, without limitation: liabilities, losses, damages, judgments, fines, penalties, amounts paid in settlement, expenses, attorneys'attorneys’ fees and costs. Expenses incurred in defending a civil, criminal, administrative, investigative or other action, suit or proceeding may be paid by the corporation in advance of the final disposition of such action, suit or proceeding in accordance with the provisions of Section 8.75 of the BCA.
     The indemnification and advancement of expenses provided by this Article shall not be deemed exclusive of any other rights to which any person indemnified may be entitled under any statute, by-law, agreement, vote of shareholders, or disinterested directors or otherwise, both as to action in his official capacity and as to action in any other capacity while holding such office, and shall continue as to a person who has ceased to be such director, officer, employee or agent and shall inure to the benefit of the heirs, executors and administrators of such person. PARAGRAPH 2:
Paragraph 2: The corporation may purchase and maintain insurance on behalf of any person referred to in the preceding paragraph against any liability asserted against him or her and incurred by him or her in any such capacity, or arising out of his or her status as such, whether or not the corporation would have the power to indemnify him or her against such liability under the provisions of this Article or otherwise. PARAGRAPH 3:
Paragraph 3: For purposes of this Article, references to "the corporation"“the corporation” shall include, in addition to the resulting corporation, any constituent corporation (including any constituent of a constituent) absorbed in a consolidation or merger which, if its separate existence had continued, would have had power and authority to indemnify its directors, officers, employees or agents, so that any person who is or was a director, officer, employee or agent of such constituent corporation, or is or was serving at the request of such constituent corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise, shall stand in the same position under the provisions of this Article with respect to the resulting or surviving corporation as he or she would have with respect to such constituent corporation if its separate existence had continued. PARAGRAPH 4:
Paragraph 4: The provisions of this Article shall be deemed to be a contract between the corporation and each director or officer who serves in any such capacity at any time while this Article and the relevant provisions of the BCA, or other applicable law, if any, are in effect, and any repeal or modification of any such law or of this II-1

II - 1


Article shall not affect any rights or obligations then existing with respect to any state of facts then or theretofore existing or any action, suit or proceeding theretofore or thereafter brought or threatened based in whole or in part upon any such state of facts. PARAGRAPH 5:
Paragraph 5: For purposes of this Article, references to "other enterprises"“other enterprises” shall include employee benefit plans; references to "fines"“fines” shall include any excise taxes assessed on a person with respect to any employee benefit plan; and references to "serving“serving at the request of the corporation"corporation” shall include any service as a director, officer, employee or agent of the corporation which imposes duties on, or involves services by, such director, officer, employee or agent with respect to any employee benefit plan, its participants, or beneficiaries; and a person who acted in good faith and in a manner he or she reasonably believed to be in the interest of the participants and beneficiaries of an employee benefit plan shall be deemed to have acted in a manner not opposed to the best interests of the corporation.
     Section 6.3 of the Registrant'sRegistrant’s By-laws provides as follows:
SECTION 6.3.6.3 MANDATORY INDEMNIFICATION.INDEMNIFICATION. To the extent that a director, officer, employee or agent of a corporation, or any subsidiary or subsidiaries, as the case may be, has been successful on the merits or otherwise in defense of any action, suit or proceeding referred to in Sections 6.1 and 6.2, or in defense of any claim, issue or matter therein, such person shall be indemnified against expenses (including attorneys'attorneys’ fees) actually and reasonably incurred by him or her in connection therewith.
     The Illinois Business Corporation Act provides for indemnification of officers, directors, employees and agents as follows:
5/8.75 INDEMNIFICATION OF OFFICERS, DIRECTORS, EMPLOYEES AND AGENTS; INSURANCE.(a) A corporation may indemnify any person who was or is a party, or is threatened to be made a party to any threatened, pending or completed action, suit or proceeding, whether civil, criminal, administrative or investigative (other than an action by or in the right of the corporation) by reason of the fact that he or she is or was a director, officer, employee or agent of the corporation, or who is or was serving at the request of the corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise, against expenses (including attorneys'attorneys’ fees), judgments, fines and amounts paid in settlement actually and reasonably incurred by such person in connection with such action, suit or proceeding, if such person acted in good faith and in a manner he or she reasonably believed to be in, or not opposed to the best interests of the corporation, and, with respect to any criminal action or proceeding, had no reasonable cause to believe his or her conduct was unlawful. The termination of any action, suit or proceeding by judgment, order, settlement, conviction, or upon a plea ofnolo contendereor its equivalent, shall not, of itself, create a presumption that the person did not act in good faith and in a manner which he or she reasonably believed to be in or not opposed to the best interests of the corporation or, with respect to any criminal action or proceeding, that the person had reasonable cause to believe that his or her conduct was unlawful.
     (b) A corporation may indemnify any person who was or is a party, or is threatened to be made a party to any threatened, pending or completed action or suit by or in the right of the corporation to procure a judgment in its favor by reason of the fact that such person is or was a director, officer, employee or agent of the corporation, or is or was serving at the request of the corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise, against expenses (including attorneys'attorneys’ fees) actually and reasonably incurred by such person in connection with the defense or settlement of such action or suit, if such person acted in good faith and in a manner he or she reasonably believed to be in, or not opposed to, the best interests of the corporation, provided that no indemnification shall be made with respect to any claim, issue, or matter as to which such person has been adjudged to have been liable to the corporation, unless, and only to the extent that the court in which such action or suit was brought shall determine upon application that, despite the adjudication of liability, but in view of all the circumstances of the case, such person is fairly and reasonably entitled to indemnity for such expenses as the court shall deem proper.
     (c) To the extent that a present or former director, officer or employee of a corporation has been successful, on the merits or otherwise, in the defense of any action, suit or proceeding referred to in subsections (a) and (b), or in defense of any claim, issue or matter therein, such person shall be indemnified against expenses (including attorneys'attorneys’ fees) actually and reasonably incurred by such person in connection therewith if the person II-2

II - 2


acted in good faith and in a manner he or she reasonably believed to be in, or not opposed to, the best interests of the corporation.
     (d) Any indemnification under subsections (a) and (b) (unless ordered by a court) shall be made by the corporation only as authorized in the specific case, upon a determination that indemnification of the present or former director, officer, employee or agent is proper in the circumstances because he or she has met the applicable standard of conduct set forth in subsections (a) or (b). Such determination shall be made with respect to a person who is a director or officer at the time of the determination: (1) by the majority vote of the directors who are not parties to such action, suit or proceeding, even though less than a quorum, (2) by a committee of the directors designated by a majority vote of the directors, even though less than a quorum, (3) if there are no such directors, or if the directors so direct, by independent legal counsel in a written opinion, or (4) by the shareholders.
     (e) Expenses (including attorney'sattorney’s fees) incurred by an officer or director in defending a civil or criminal action, suit or proceeding may be paid by the corporation in advance of the final disposition of such action, suit or proceeding upon receipt of an undertaking by or on behalf of the director or officer to repay such amount if it shall ultimately be determined that such person is not entitled to be indemnified by the corporation as authorized in this Section. Such expenses (including attorneys'attorneys’ fees) incurred by former directors and officers or other employees and agents may be so paid on such terms and conditions, if any, as the corporation deems appropriate.
     (f) The indemnification and advancement of expenses provided by or granted under the other subsections of this Section shall not be deemed exclusive of any other rights to which those seeking indemnification or advancement of expenses may be entitled under any by-law, agreement, vote of shareholders or disinterested directors, or otherwise, both as to action in his or her official capacity and as to action in another capacity while holding such office.
     (g) A corporation may purchase and maintain insurance on behalf of any person who is or was a director, officer, employee or agent of the corporation, or who is or was serving at the request of the corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise, against any liability asserted against such person and incurred by such person in any such capacity, or arising out of his or her status as such, whether or not the corporation would have the power to indemnify such person against such liability under the provisions of this Section.
     (h) If a corporation indemnifies or advances expenses to a director or officer under subsection (b) of this Section, the corporation shall report the indemnification or advance in writing to the shareholders with or before the notice of the next shareholders meeting.
     (i) For purposes of this Section, references to "the corporation"“the corporation” shall include, in addition to the surviving corporation, any merging corporation (including any corporation having merged with a merging corporation) absorbed in a merger which, if its separate existence had continued, would have had the power and authority to indemnify its directors, officers, and employees or agents, so that any person who was a director, officer, employee or agent of such merging corporation, or was serving at the request of such merging corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise, shall stand in the same position under the provisions of this Section with respect to the surviving corporation as such person would have with respect to such merging corporation if its separate existence had continued.
     (j) For purposes of this Section, reference to "other enterprises"“other enterprises” shall include employee benefit plans; references to "fines"“fines” shall include any excise taxes assessed on a person with respect to an employee benefit plan; and references to "serving“serving at the request of the corporation"corporation” shall include any service as a director, officer, employee or agent of the corporation which imposes duties on, or involves services by such director, officer, employee, or agent with respect to an employee benefit plan, its participants, or beneficiaries. A person who acted in good faith and in a manner he or she reasonably believed to be in the best interests of the participants and beneficiaries of an employee benefit plan shall be deemed to have acted in a manner "not“not opposed to the best interest of the corporation"corporation” as referred to in this Section.
     (k) The indemnification and advancement of expenses provided by or granted under this Section shall, unless otherwise provided when authorized or ratified, continue as to a person who has ceased to be a director, officer, employee, or agent and shall inure to the benefit of the heirs, executors, and administrators of that person. II-3

II - 3


     (l) The changes to this Section made by this amendatory Act of the 92nd General Assembly apply only to actions commenced on or after the effective date of this amendatory Act of the 92nd General Assembly. (Last amended by P.A. 92-0033,92 0033, L. '01,‘01, eff. 7-1-01.7 1 01.)
     Wintrust has purchased $30 million of insurance policies which insure Wintrust'sWintrust’s directors and officers against liability which they may incur as a result of actions taken in such capacities. In addition, Wintrust maintains fiduciary liability coverage up to a $5 million limit and trust errors and omissions coverage up to a limit of $15 million. ITEM
Item 21. EXHIBITS AND FINANCIAL STATEMENT SCHEDULES.Exhibits and Financial Statement Schedules.
     (a) Exhibits: A list of the exhibits included as part of this registration statement is set forth on the list of exhibits immediately preceding such exhibits and is incorporated herein by reference.
Exhibit
NumberDescription of Exhibit
2.1Agreement and Plan of Merger by and between Wintrust Financial Corporation and Hinsbrook Bancshares, Inc., dated as of December 5, 2005 (included asAnnex Ato this proxy statement/prospectus).
3.1Amended and Restated Articles of Incorporation of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.1 of the Company’s Form 10-Q for the quarter ended June 30, 2005).
3.2Articles of Amendment of Amended and Restated Articles of Incorporation of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.2 of the Company’s Form 10-Q for the quarter ended June 30, 2005).
3.3Amended and Restated By-laws of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.3 of the Company’s Form 8-K filed with the Securities and Exchange Commission on January 5, 2006).
3.4Statement of Resolution Establishing Series of Junior Serial Preferred Stock A of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.2 of the Company’s Form 10-K for the year ended December 31, 1998).
5.1*Opinion of Sidley Austin LLP.
8.1*Tax Opinion of Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP.
23.1+Consent of Ernst & Young LLP.
23.2+Consent of Capital Market Securities, Inc.
23.3*Consent of Sidley Austin LLP (included in Exhibit 5.1).
23.4*Consent of Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP (included in Exhibit 8.1).
24.1*Power of Attorney (contained in signature page to the registration statement).
99.1+Form of proxy card.
99.2+Form of election card.
* Previously filed
+ Filed herewith
     (b) Financial Statement Schedules:
     All schedules for which provision is made in the applicable accounting regulations of the Securities and Exchange Commission have been omitted because they are not required, amounts which would otherwise be required to be shown with respect to any item are not material, are inapplicable or the required information has already been provided elsewhere or incorporated by reference in the registration statement. II-4 ITEM

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Item 22: UNDERTAKINGS.Undertakings.
     (a) The undersigned registrant hereby undertakesundertakes:
     (1) To file, during any period in which offers or sales are being made, a post-effective amendment to respond to requests for information that is incorporatedthis registration statement:
     (i) To include any prospectus required by reference intoSection 10(a)(3) of the Securities Act of 1933;
     (ii) To reflect in the prospectus pursuant to Item 4, 10(b), 11,any facts or 13 of this form, within one business day of receipt of such request, and to send the incorporated documents by first class mail or other equally prompt means. This includes information contained in documents filed subsequent toevents arising after the effective date of the registration statement through(or the datemost recent post-effective amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set forth in the registration statement. Notwithstanding the foregoing, any increase or decrease in volume of respondingsecurities offered (if the total dollar value of securities offered would not exceed that which was registered) and any deviation from the low or high end of the estimated maximum offering range may be reflected in the form of prospectus filed with the Commission pursuant to Rule 424(b) if, in the aggregate, the changes in volume and price represent no more than a 20 percent change in the maximum aggregate offering price set forth in the “Calculation of Registration Fee” table in the effective registration statement;
     (iii) To include any material information with respect to the request. (b) The undersigned registrant hereby undertakesplan of distribution not previously disclosed in the registration statement or any material change to supplysuch information in the registration statement.
     (2) That, for the purpose of determining any liability under the Securities Act of 1933, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.
     (3) To remove from registration by means of a post-effective amendment all information concerning a transaction, andany of the companysecurities being acquired involved therein, that was notregistered which remain unsold at the subjecttermination of and included in the registration statement when it became effective. (c)offering.
     (b) The undersigned registrant hereby undertakes that, for purposes of determining any liability under the Securities Act of 1933, each filing of the registrant'sregistrant’s annual report pursuant to Section 13(a) or Section 15(d) of the Securities Exchange Act of 1934, as amended, that is incorporated by reference in this Registration Statement shall be deemed to be a new registration statement relating to the securities offered herein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.
     (c)(1) The undersigned registrant hereby undertakes as follows: that prior to any public reoffering of the securities registered hereunder through use of a prospectus which is a part of this registration statement, by any person or party who is deemed to be an underwriter within the meaning of Rule 145(c), the issuer undertakes that such reoffering prospectus will contain the information called for by the applicable registration form with respect to reofferings by persons who may be deemed underwriters, in addition to the information called for by the other items of the applicable form.
     (c)(2) The undersigned registrant hereby undertakes as follows: that every prospectus: (1) that is filed pursuant to the paragraph immediately preceding, or (2) that purports to meet the requirements of Section 10(a)(3) of the Securities Act of 1933 and is used in connection with an offering of securities subject to Rule 415, will be filed as part of an amendment to this registration statement and will not be used until such amendment is effective, and that, for purposes of determining any liability under the Securities Act of 1933, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.
     (d) Insofar as indemnification for liabilities arising under the Securities Act of 1933 may be permitted to directors, officers and controlling persons of the registrant pursuant to the foregoing provisions, or otherwise, the registrant has been advised that in the opinion of the Securities and Exchange Commission such indemnification is against public policy as expressed in the Act and is, therefore, unenforceable. In the event that a claim for

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indemnification against such liabilities (other than the payment by the registrant of expenses incurred or paid by a director, officer or controlling person of the registrant in the successful defense of any action, suit or proceeding) is asserted by such director, officer or controlling person in connection with the securities being registered, the registrant will, unless in the opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification by it is against policy as expressed in the Act and will be governed by the final adjudication of such issue.
     (e) The undersigned registrant hereby undertakes that: (1) For purposes of determining any liability underto respond to requests for information that is incorporated by reference into the Securities Act of 1933, the information omitted from the form of prospectus filed as partpursuant to Item 4, 10(b), 11, or 13 of this form, within one business day of receipt of such request, and to send the incorporated documents by first class mail or other equally prompt means. This includes information contained in documents filed subsequent to the effective date of the registration statement through the date of responding to the request.
     (f) The undersigned registrant hereby undertakes to supply by means of a post-effective amendment all information concerning a transaction, and the company being acquired involved therein, that was not the subject of and included in reliance upon Rule 430A and contained in a form of prospectus filed by the registrant pursuant to Rule 424(b)(1) or (4) or 497(h) under the Securities Act shall be deemed to be part of this registration statement as of the timewhen it was declaredbecame effective. (2) For the purpose of determining any liability under the Securities Act of 1933, each post-effective amendment that contains a form of prospectus shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof. II-5

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SIGNATURES
     Pursuant to the requirements of the Securities Act of 1933, as amended, the registrant has duly caused this amendment to the Registration Statement to be signed on its behalf by the undersigned, thereunto duly authorized, in the City of Lake Forest, State of Illinois, on this 19th5th day of August, 2004. WINTRUST FINANCIAL CORPORATION By:/s/ David A. Dykstra ------------------------------------------- David A. Dykstra Senior Executive Vice President and Chief Operating Officer We, the undersigned directors of Wintrust Financial Corporation, and each of us, do hereby constitute and appoint each and any of Edward J. Wehmer and David A. Dykstra, our true and lawful attorney-in-fact and agents, with full power of substitution and re-substitution, for us and in our name, place and stead, in any and all capacities, to sign any and all amendments to this Registration Statement, and to file the same, with all exhibits thereto, and all other documents in connection therewith, with the Securities and Exchange Commission, granting unto said attorneys-in-fact and agents full power and authority to do and perform each and every act and thing requisite and necessary to be done, as fully to all intents and purposes as we might or could do in person, hereby ratifying and confirming said attorneys-in-fact and agents or their substitutes may lawfully do or cause to be done by virtue hereof.May, 2006.
WINTRUST FINANCIAL CORPORATION
By:/s/ David A. Dykstra
David A. Dykstra
Senior Executive Vice President and Chief
Operating Officer
     Pursuant to the requirements of the Securities Act of 1933, as amended, this amendment to the Registration Statement has been signed by the following persons in the capacities and on the date indicated.
NAME TITLE DATE ---- ----- ---- /s/
NameTitleDate
/s/ Edward J. Wehmer - ---------------------------------------- President, Chief Executive
Edward J. WehmerOfficer and Director August 19, 2004 /s/May 5, 2006
/s/ David L. StoehrExecutive Vice President and - ----------------------------------------
David L. StoehrChief Financial Officer David L. Stoehr (Principal
(Principal Accounting Officer) August 19, 2004 /s/ May 5, 2006
*Chairman and DirectorMay 5, 2006
John S. Lillard - ---------------------------------------- Chairman and
Director August 19, 2004 John S. Lillard /s/
Alan E. Bulley
*DirectorMay 5, 2006
Peter D. Crist - ----------------------------------------
*Director August 19, 2004 Peter D. Crist /s/ May 5, 2006
Bruce K. Crowther - ----------------------------------------
*Director August 19, 2004 Bruce K. Crowther /s/ May 5, 2006
Joseph F. Damico
*DirectorMay 5, 2006
Bert A. Getz, Jr. - ----------------------------------------
*Director August 19, 2004 Bert A. Getz, Jr. /s/ Philip W. Hummer - ---------------------------------------- Director August 19, 2004 Philip W. Hummer /s/ Paul J. Liska - ---------------------------------------- Director August 19, 2004 Paul J. Liska
S-1
NAME TITLE DATE ---- ----- ---- /s/
May 5, 2006
James B. McCarthy - ----------------------------------------

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NameTitleDate
*Director August 19, 2004 James B. McCarthy - ---------------------------------------- Director May 5, 2006
Albin F. Moschner /s/
*DirectorMay 5, 2006
Thomas J. Neis - ----------------------------------------
*Director August 19, 2004 Thomas J. Neis /s/ May 5, 2006
Hollis W. Rademacher - ----------------------------------------
*Director August 19, 2004 Hollis W. Rademacher - ---------------------------------------- Director May 5, 2006
J. Christopher Reyes /s/
*DirectorMay 5, 2006
John J. Schornack - ----------------------------------------
*Director August 19, 2004 John J. Schornack /s/ May 5, 2006
Ingrid S. Stafford - ---------------------------------------- Director August 19, 2004 Ingrid S. Stafford
S-2 INDEX TO EXHIBITS EXHIBIT NUMBER DESCRIPTION OF EXHIBIT - ------- ---------------------- 2.1 Agreement and Plan of Merger by and between Wintrust Financial Corporation and Town Bankshares, Ltd. dated as of June 14, 2004 (included as Annex A to
* David A. Dykstra hereby signs this proxy statement/prospectus). 3.1 Amended and Restated Articles of Incorporation of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.1 of the Company's Form S-1 Registration Statement (No. 333-18699) filed with the Securities and Exchange Commission on December 24, 1996). 3.2 Statement of Resolution Establishing Series of Junior Serial Preferred Stock A of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.2 of the Company's Form 10-K for the year ended December 31, 1998). 3.3 Amended and Restated By-laws of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.3 of the Company's Form 10-Q for the quarter ended March 31, 2003). 4.1 Rights Agreement between Wintrust Financial Corporation and Illinois Stock Transfer Company, as Rights Agent, dated July 28, 1998 (incorporated by reference to Exhibit 4.1 of the Company's Form 8-A Registration Statement (No. 000-21923) filed with the Securities and Exchange Commission on August 28, 1998). 5.1 Opinion of Vedder, Price, Kaufman & Kammholz, P.C.+ 8.1 Tax Opinion of Reinhart Boerner Van Deuren s.c.+ 23.1 Consent of Ernst & Young LLP.+ 23.2 Consent of Edelman & Co., Ltd.+ 24.1 Power of Attorney (contained in signature pageAmendment No. 2 to the registration statement).statement on behalf of each of the persons indicated for whom he is attorney-in-fact on May 5, 2006 pursuant to a power of attorney.
/s/ David A. Dykstra
David A. Dykstra
Attorney-in-Fact

S - ---------------------- 2


INDEX TO EXHIBITS
Exhibit
NumberDescription of Exhibit
2.1Agreement and Plan of Merger by and between Wintrust Financial Corporation and Hinsbrook Bancshares, Inc., dated as of December 5, 2005 (included asAnnex Ato this proxy statement/prospectus).
3.1Amended and Restated Articles of Incorporation of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.1 of the Company’s Form 10-Q for the quarter ended June 30, 2005).
3.2Articles of Amendment of Amended and Restated Articles of Incorporation of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.2 of the Company’s Form 10-Q for the quarter ended June 30, 2005).
3.3Amended and Restated By-laws of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.3 of the Company’s Form 8-K filed with the Securities and Exchange Commission on January 5, 2006).
3.4Statement of Resolution Establishing Series of Junior Serial Preferred Stock A of Wintrust Financial Corporation (incorporated by reference to Exhibit 3.2 of the Company’s Form 10-K for the year ended December 31, 1998).
5.1*Opinion of Sidley Austin LLP.
8.1*Tax Opinion of Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP.
23.1+Consent of Ernst & Young LLP.
23.2+Consent of Capital Market Securities, Inc.
23.3*Consent of Sidley Austin LLP (included in Exhibit 5.1).
23.4*Consent of Barack Ferrazzano Kirschbaum Perlman & Nagelberg LLP (included in Exhibit 8.1).
24.1*Power of Attorney (contained in signature page to the registration statement).
99.1+Form of proxy card.
99.2+Form of election card.
* Previously filed
+ Filed herewith.
herewith