UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

(Rule 14a-101)

INFORMATION REQUIRED IN PROXY STATEMENT

SCHEDULE 14A INFORMATION

PROXY STATEMENT PURSUANT TO SECTIONProxy Statement Pursuant to Section 14(a) OF THE SECURITIESof the Securities

EXCHANGE ACT OFExchange Act of 1934 (Amendment No.            )

Filed by the Registrantþ

Filed by a Party other than the Registrant¨

Check the appropriate box:

ALLEGHANY CORPORATION

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than Registrant)

Payment of Filing Fee (Check the appropriate box):

ALLEGHANY CORPORATION

7 Times Square Tower

New York, New York 10036

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

April 27, 201226, 2013 at 10:00 a.m., Local Time

HarvardThe Penn Club of New York City

3530 West 44^thStreet

New York, New York

Alleghany Corporation (“Alleghany”) hereby gives notice that its 20122013 Annual Meeting of Stockholders will be held at the HarvardThe Penn Club, of New York City, 3530 West 44^th Street, New York, New York, on Friday, April 27, 201226, 2013 at 10:00 a.m., local time, for the following purposes:

Holders of Alleghany common stock at the close of business on March 14, 20121, 2013 are entitled to receive this Notice and vote for the election of directors and on each of the other matters set forth above at the 20122013 Annual Meeting and any adjournments of this meeting.

You are cordially invited to be present. Ifattend the 2013 Annual Meeting. Representation of your shares at the meeting is very important. Whether or not you do not expectplan to attend in person, we encourage you mayto vote your shares promptly by telephone, by the Internet, or by signing and returning the enclosed proxy card in the envelope provided. Representation of your shares is very important. We ask that you submit your proxy promptly. You may revoke your proxy at any time prior to its beingbefore it is voted at the 2013 Annual Meeting by written notice to the Secretary of Alleghany, by submitting a new proxy with a later date, or by voting in person at the 20122013 Annual Meeting.

By order of the Board of Directors

March 16, 201215, 2013

Important Notice Regarding Internet Availability of Proxy Materials for the Alleghany Corporation 20122013 Annual Meeting of Stockholders to be Held on April 27, 2012: Our proxy26, 2013: Proxy materials relating to our 20122013 Annual Meeting (notice of meeting, proxy statement, proxy and 20112012 Annual Report to Stockholders on Form 10-K) are also available on the Internet. Please go to www.edocumentview.com/YAL to view and obtain the proxy materials online.

ALLEGHANY CORPORATION

7 Times Square Tower

New York, New York 10036

PROXY STATEMENT

20122013 Annual Meeting of Stockholders to be held April 27, 201226, 2013

Alleghany Corporation, referred to in this proxy statement as “Alleghany,” “we,” “our,” or “us”“us,” is providing these proxy materials in connection with the solicitation of proxies by the Board of Directors of Alleghany, or the “Board,” from holders of Alleghany’s outstanding shares of common stock entitled to vote at our 20122013 Annual Meeting of Stockholders, or the “2012“2013 Annual Meeting,” and at any and all adjournments or postponements, for the purposes referred to belowherein and in the accompanying Notice of Annual Meeting of Stockholders. These proxy materials are being mailed to stockholders on or about March 16, 2012.15, 2013.

References to “common stock” in this proxy statement refer to the common stock, par value $1.00 per share, of Alleghany unless the context otherwise requires.

On March 6, 2012, we completed the acquisition of Transatlantic Holdings, Inc. (“Transatlantic”) pursuant to the merger agreement entered into between Alleghany and Transatlantic on November 21, 2011. As part of the consideration for the merger, we issued 8,360,959 shares of our common stock to the former stockholders of Transatlantic. In addition, in accordance with the terms of the merger agreement, three former directors of Transatlantic became directors of Alleghany effective upon the closing of the acquisition. One of the three former Transatlantic directors, John G. Foos, was appointed to the class of 2012 and will stand for election to the class of 2015 at the 2012 Annual Meeting.

Information About Voting

Alleghany’sThe Board has fixed the close of business on March 14, 20121, 2013 as the record date for the determination of stockholders entitled to notice of, and to vote at, the 20122013 Annual Meeting. Stockholders are entitled to one vote for each share of common stock held of record on the record date with respect to each matter to be acted on at the 20122013 Annual Meeting. As of the close of business on March 14, 2012,1, 2013, there were 16,926,27416,803,490 shares of Alleghany common stock outstanding and entitled to vote.

The presence, in person or by proxy, of holders of a majority of the outstanding shares of Alleghany’s common stock is required to constitute a quorum for the transaction of business at the 20122013 Annual Meeting. Abstentions and “broker non-votes” (shares held by a broker or nominee that does not have discretionary authority to vote on a particular matter and has not received voting instructions from its client) are counted for purposes of determining the presence or absence of a quorum for the transaction of business at the 20122013 Annual Meeting. Under applicable rules of the New York Stock Exchange, brokers may not use discretionary authority to vote shares of Alleghany’s common stock held for clients on any of the matters to be considered at the 20122013 Annual Meeting other than the ratification of our selection of Ernst & Young LLP as Alleghany’s independent registered public accounting firm. Accordingly, it is important that, if your shares are held by a broker, you provide instructions to your broker so that your votes with respect to the election of directors approval of Alleghany’s 2012 Long-Term Incentive Plan, and the advisory vote on executive compensation are counted.

There are three ways to vote by proxy: by calling the toll free telephone number on the enclosed proxy card,card; by using the Internet as described on the enclosed proxy cardcard; or by returning the enclosed proxy card in the envelope provided. YouIf your shares are held by a broker you may be able to vote by telephone or the Internet if those options are offered by your shares are held by a broker; follow their instructions.broker.

TABLE OF CONTENTS

PRINCIPAL STOCKHOLDERS

The following table sets forth the beneficial ownership of each person who, based upon information provided to Alleghany or filings made by such person with the U.S. Securities and Exchange Commission, or the “SEC,” was the beneficial owner of more than five percent our outstanding common stock.

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ALLEGHANY CORPORATE GOVERNANCE

Board of Directors

Pursuant to Alleghany’s Restated Certificate of Incorporation and By-Laws, Alleghany’sthe Board is divided into three separate classes of directors which are required to be as nearly equal in number as practicable. At each Annual Meeting of Stockholders, one class of directors is elected to a term of three years. Currently, there are three standing committees of the Board, consisting of an Audit Committee, Compensation Committee, and Nominating and Governance Committee. Additional information regarding these committees is set out below.

Alleghany’s Board currently consists of fourteentwelve directors. Upon the closing of theAlleghany’s acquisition of Transatlantic Holdings, Inc., or “Transatlantic,” on March 6, 2012, in accordance with the terms of the merger agreement, three former members of the board of directors of Transatlantic, Stephen P. Bradley, Ian H. Chippendale and John G. Foos, were appointed as directors of Alleghany, with one of such new directors being appointed to each of the Board’s three classes (Mr. Foos to the class of 2012, Mr. Bradley to the class of 2013, and Mr. Chippendale to the class of 2014). Consequently, there are currently five members of the Board whose terms will expire at the 2012 Annual Meeting: John J. Burns, Jr., Dan R. Carmichael, Mr. Foos, William K. Lavin and Raymond L.M. Wong. Mr. Burns, a director of Alleghany (or its predecessor, Alleghany Corporation, a Maryland corporation, which we refer to as “Old Alleghany”) since 1968, has not been nominated for re-election as a director of Alleghany. In addition, Dan R. Carmichael, a director of Alleghany since 1993, notified Alleghany on February 23, 2012 of his intention to retire as a director of Alleghany effective as of the 2012 Annual Meeting and, thus, he also has not been nominated for re-election as a director of Alleghany.

Because two directors whose terms expire at the 2012 Annual Meeting have not been nominated for re-election, in order to make the classes of the Board as nearly equal in size as practicable, the Board has determined to nominate Phillip M. Martineau, who was last elected to the Board at the 2010 Annual Meeting, to stand for re-election at the 2012 Annual Meeting. As a result, the directors that have been nominated by the Board for election at the 2012 Annual Meeting to the class of 2015 are Messrs. Foos, Lavin, Martineau, and Wong. Since Messrs. Burns and Carmichael have not been nominated for re-election at the 2012 Annual Meeting, if all of Messrs. Foos, Lavin, Martineau and Wong are elected, the size of the Board will be reduced effective at the 2012 Annual Meeting from fourteen to twelve directors.classes.

The Board held 10eight meetings in 2011.2012. Each director who served as a director of Alleghany any time during 20112012 attended more than 75% of the aggregate number of meetings of the Board and meetings of the committees of the Board on which he or she served that were held in 2011.2012. There are twothree regularly scheduled executive sessions for non-managementindependent directors of Alleghany and one regularly scheduled executive session for independent directors each year. The Chairman, who is currently an independent director, presides at these executive sessions. Alleghany does not have a policy with regard to attendance by directors at Annual Meetings of Stockholders. ThreeTwo directors attended the 20112012 Annual Meeting of Stockholders.

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Director Independence

Pursuant to the New York Stock Exchange’s listing standards, Alleghany is required to have a majority of independent directors, and no director qualifies as independent unless the Board affirmatively determines that the director has no material relationship with Alleghany. The Board has determined that Rex D. Adams, Stephen P. Bradley, Karen Brenner, Dan R. Carmichael, Ian H. Chippendale, John G. Foos, Jefferson W. Kirby, William K. Lavin, Thomas S. Johnson, Phillip M. Martineau, James F. Will and Raymond L.M. Wong have no material relationship with Alleghany (either directly or as a partner, shareholder or officer of an organization that has a relationship with Alleghany) other than in their capacities as members of the Board and committees thereof, and thus are independent directors of Alleghany, based upon the fact that none of such directors has any material relationship with Alleghany either directly or as a partner, shareholder or officer of an organization that has a relationship with Alleghany. As a result, twelveeleven of Alleghany’s current fourteentwelve directors are independent directors. All of the director nominees, Ms. Brenner and Messrs. Foos, Lavin, MartineauBradley, Johnson and Wong,Will, are independent. Assuming that allIn addition, Dan R. Carmichael, who retired as a director of Messrs. Foos, Lavin, Martineau and Wong are elected atAlleghany effective as of the 2012 Annual Meeting the size of Stockholders, qualified as an independent director during his service on the Board will be reduced effective at the 2012 Annual Meeting from fourteen to twelve directors, and eleven of Alleghany’s twelve directors will be independent directors.in 2012.

Board Leadership

Currently, the positionsposition of Chairman and the position of President and chief executive officer, are separate. It is the policy of the Board that the Chairman should not be an Alleghany officer. The current Chairman is an independent director. Pursuant to the Corporate Governance Guidelines of Alleghany, or the “Corporate Governance Guidelines,” the duties of the Chairman include providing leadership to the Board in managing the business of the Board and ensuring that there is an effective structure for the operation of the Board and its committees. The Board believes that its leadership structure is appropriate given the historical development of the composition of the Board and management, the Corporate Governance Guidelines, and the significant tenure of a majority of the Board members.

Board Role in Risk Oversight

The Board oversees risk management directly and through its Audit Committee, Compensation Committee, and Nominating and Governance Committee. In addition, Alleghany management has several committees that it uses group-wide to monitor and manage risk at Alleghany and its subsidiaries, including a Risk Management Committee, Reinsurance Security Committee Investment Committeeand Ethics and Legal Compliance Committee. Alleghany management regularly reports to the Board and, as appropriate, to the committees of the Board on management’s activities and risk tolerances. Each year at the Board’s December or January meeting, the Board receives a formal report on enterprise risk management and, at the same meeting, considers Alleghany’s five-year strategic plan

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financial estimates and the evaluation of the chief executive officer, allowing the Board to consider risk and risk management in the context of theAlleghany’s strategic plan and management’s performance. At the Audit Committee’s June meeting, it receives a formal report on enterprise risk management and legal compliance, which is also copied to the Board, and the Audit Committee subsequently reports thereon to the Board. The Board believes that risk oversight is a responsibility of the entire Board, and it does not look to any individual director or committee to lead it in discharging this responsibility.

Committees of the Board of Directors

Audit Committee

The current members of the Audit Committee are Messrs. Lavin (Chairman), Adams, CarmichaelFoos and Wong and Ms. Brenner. The Board has determined that each of these members

has the qualifications set forth in the New York Stock Exchange’s listing standards regarding financial literacy and accounting or related financial management expertise, and is an audit committee financial expert as defined by the SEC. The Board has also determined that each of the members of the Audit Committee is independent as defined in the New York Stock Exchange’s listing standards. The Audit Committee operates pursuant to a Charter, a copy of which is available on Alleghany’s website at www.alleghany.com or may be obtained, without charge, upon written request to the Secretary of Alleghany at Alleghany’s principal executive offices. Pursuant to its Charter, the Audit Committee is directly responsible for the appointment, compensation, retention and oversight of the work of the independent registered public accounting firm, including approving in advance all audit services and permissible non-audit services to be provided by the independent registered public accounting firm. The Audit Committee is also directly responsible for the evaluation of such firm’s qualifications, performance and independence. The Audit Committee also reviews and makes reports and recommendations to the Board with respect to the following matters:

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The Audit Committee held nine meetings in 2011.2012.

Compensation Committee

The current members of the Compensation Committee are Messrs. CarmichaelWill (Chairman), Chippendale, Johnson, Lavin, Martineau Will and Wong, each of whom the Board has determined is

independent as defined in the New York Stock Exchange’s listing standards. The Compensation Committee operates pursuant to a Charter, a copy of which is available on Alleghany’s website at www.alleghany.com or may be obtained, without charge, upon written request to the Secretary of Alleghany at Alleghany’s principal executive offices. Alleghany’s executive compensation program is administered by the Compensation Committee. Pursuant to its Charter, the Compensation Committee is, among other things, charged with:

In addition, the Compensation Committee also is responsible for reviewing the annual recommendations of the chief executive officer concerning:

The Compensation Committee provides a report on the actions described above to the Board and makes recommendations with respect to such actions to the Board as the

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Compensation Committee may deem appropriate. Compensation adjustments and awards are generally made annually by the Compensation Committee at a meeting in December or January.

In addition, the Compensation Committee is responsible for reviewing the compensation of the directors on an annual basis, including compensation for service on committees of the Board, and proposing changes, as appropriate, to the Board. The Compensation Committee also administers Alleghany’s 2002 Long-Term Incentive Plan, or the “2002 LTIP,” the 2007 Long-Term Incentive Plan, or the “2007 LTIP,” the 2012 Long-Term Incentive Plan, or the “2012 LTIP,” and the 2010 Management Incentive Plan, or the “2010 MIP,MIP.” and, if the 2012 Long-Term Incentive Plan (the “2012 LTIP”) is approved by stockholders at the 2012 Annual Meeting, the Compensation Committee will also administer the 2012 LTIP.

Alleghany’s Senior Vice President, General Counsel and Secretary, Christopher K. Dalrymple, supports the Compensation Committee in its work. In addition, during 2011,from January through September 2012, the

Compensation Committee engaged Grahall Partners as independent outside compensation consultant. In September 2012, following a competitive process, the Compensation Committee engaged Frederic W. Cook & Co., Inc., or the “Compensation Consultant,” as independent outside compensation consultant to advise it on executive compensation matters. The Compensation Consultant also advised the Compensation Committee and management on various executive compensation matters involving Alleghany’s operating subsidiaries. The Chairman of the Compensation Committee reviews and approves all fees Alleghany pays to the Compensation Consultant.

The Compensation Committee held seven meetings in 2011.2012.

Nominating and Governance Committee

The current members of the Nominating and Governance Committee are Messrs. Adams (Chairman), Bradley, Johnson, Martineau and Will and Ms. Brenner, each of whom the Board has determined is independent as defined in the New York Stock Exchange’s listing standards. The Nominating and Governance Committee operates pursuant to a Charter, a copy of which is available on Alleghany’s website at www.alleghany.com or may be obtained, without charge, upon written request to the Secretary of Alleghany at Alleghany’s principal executive offices. Pursuant to its Charter, the Nominating and Governance Committee is charged with:

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The Nominating and Governance Committee will receive at any time and will consider from time to time suggestions from stockholders as to proposed director candidates. In this regard, a stockholder may submit a recommendation regarding a proposed director nominee in writing to the Nominating and Governance Committee in care of the Secretary of Alleghany at Alleghany’s principal executive offices. Any such persons recommended by a stockholder will be evaluated in the same manner as persons identified by the Nominating and Governance Committee.

The Board generally seeks members with diverse business and professional backgrounds and outstanding integrity and judgment, and such other skills and experience as will enhance

the Board’s ability to best serve Alleghany’s interests. The Board has not approved any specific criteria for nominees for director nor established a procedure for identifying and evaluating nominees for director. The Board believes that establishing such criteria is best left to an evaluation of Alleghany’s needs at the time that a nomination is to be considered. In view of the infrequency of vacancies on the Board, the Nominating and Governance Committee does not have an established procedure for identifying and evaluating nominees for director or any specific qualities, skills or minimum qualifications that it believes are necessary for one or more of Alleghany’s directors to possess. However, as a general matter, the Nominating and Governance Committee does consider diversity in identifying and evaluating possible nominees for directordirector.

The Nominating and Governance Committee held fiveeight meetings in 2011.2012.

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Communications with Directors

Interested parties may communicate directly with any individual director, the non-managementindependent directors as a group or the Board as a whole by mailing such communication to the Secretary of Alleghany at Alleghany’s principal executive offices. Any such communications will be delivered unopened:

Director Retirement Policy

Alleghany’s retirement policy for directors who will be in office following the 2012 Annual Meeting provides that a director must retire from the Board at the next Annual Meeting of Stockholders following his or her 75^th birthday.

Related Party Transactions

The Board has adopted a written Related Party Transaction Policy, or “the Policy.” Pursuant to the Policy, all related party transactions must be approved in advance by the Board. Under the Policy, a related party transaction means any transaction, other than compensation

for services as an officer or director authorized and approved by the Compensation Committee or the Board, in which Alleghany or any of its subsidiaries is a participant and in which any:

has or will have a direct or indirect material interest. A person who has a position or relationship with a firm, corporation or other entity may be deemed to have an indirect interest in any transaction in which that entity engages. However, a person is not deemed to have an interest

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if such interest arises only from such person’s position as a director of another corporation and/or such person’s direct and indirect ownership of less than 10% of the equity of such firm, corporation, or other entity.

Under the Policy, all newly proposed related party transactions are referred to the Nominating and Governance Committee for review and consideration of its recommendation to the Board. Following this review, the related party transaction and the Nominating and Governance Committee’s analysis and recommendations are presented to the full Board (other than any directors interested in the transaction) for approval. The Nominating and Governance Committee reviews existing related party transactions annually, with the goals of ensuring that such transactions are being pursued in accordance with all of the understandings and commitments made at the time they were approved, ensuring that payments being made with respect to such transactions are appropriately reviewed and documented, and reaffirming that such transactions remain in the best interests of Alleghany. The Nominating and Governance Committee reports any such findings to the Board.

Upon the closing of the acquisition of Transatlantic on March 6, 2012, Joseph P. Brandon was named an Executive Vice President of Alleghany. During the period from September 15, 2011 through the closing date, Mr. Brandon was engaged by Alleghany as a consultant. Mr. Brandon was paid consulting fees of $253,333$400,000 during fiscal 2011.2012.

Codes of Ethics

Alleghany has adopted a Financial Personnel Code of Ethics for its chief executive officer, chief financial officer, chief accounting officer, vice president for tax matters and all professionals serving in a finance, accounting, treasury or tax role, and a Code of Ethics and

Business Conduct for its directors, officers and employees, and the Corporate Governance Guidelines. Copies of each of these documents are available on Alleghany’s website at www.alleghany.com or may be obtained, without charge, upon written request to the Secretary of Alleghany at Alleghany’s principal executive offices. Alleghany will disclose on its website any substantive amendments to these Codes of Ethics and any waivers from the provisions of these Codes of Ethics made with respect to its chief executive officer, chief financial officer or chief accounting officer (or persons performing similar functions) as well as with respect to any other executive officer or any director of Alleghany.

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Majority Election of Directors

Alleghany’s By-Laws provide for a majority voting standard for the election of directors for uncontested elections. In connection with such provision of the By-Laws, the Corporate Governance Guidelines provide that a director nominee, as a condition of his or her nomination, shall tender to the Board, at the time of nomination, an irrevocable resignation in the event that the director fails to receive the majority vote required by the By-Laws, effective upon the Board’s acceptance of such resignation. In the event that a director nominee fails to receive the requisite majority vote, the Nominating and Governance Committee will evaluate such resignation in light of Alleghany’s best interests and make a recommendation to the Board as to whether the Board should accept the resignation. In making its recommendation, the Nominating and Governance Committee may consider any factors it deems relevant, including:

The Board, by vote of independent directors other than the director whose resignation is being evaluated, will act on the tendered resignation and will publicly disclose its decision and rationale within 90 days following certification of the stockholder vote.

Director Stock Ownership Guidelines

Directors are expected to achieve ownership of common stock, or equivalent common stock units, having an aggregate value (based upon the higher of market value or book value) equal to at least five times the annual board retainer within five years of election to the Board, and to maintain such a level thereafter.

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SECURITIES OWNERSHIP OF DIRECTORS AND EXECUTIVE OFFICERS

The following table sets forth, as of March12, 2012,March 1, 2013, the beneficial ownership of common stock of each of the nominees named for election as a director, each of the other current directors, each of the executive officers named in the Summary Compensation Table on page 66,50, and all nominees, directors and executive officers as a group, except for Robert M. Hart who retired as Senior Vice President—Law on April 30, 2011.group.

case of Mr. Adams, 2,1021,010 shares of common stock in the case of Ms. Brenner and Mr. Burns,Martineau and 5,534167 shares of common stock in the case of Mr. Johnson,Messrs. Bradley, Chippendale and Foos, issuable under stock options granted pursuant to the 2010 Directors’ Stock Plan, or the “2010 Directors’ Plan,” the 2005 Directors’ Stock Plan, or the “2005

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(9)	Includes 60200 shares of common stock owned by Mr. Carr’s wife. Mr. Carr had no voting or investment power over these shares, and he disclaims beneficial ownership of them.Wong’s children.

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Section 16(a) Beneficial Ownership Reporting Compliance

Alleghany has determined that, except as set forth below, no person who at any time during 20112012 was a director, officer or beneficial owner of more than 10% of common stock failed to file on a timely basis reports required by Section 16(a) of the Securities Exchange Act of 1934, as amended, during 2011.2012. This determination is based solely upon Alleghany’s review of Forms 3, 4 and 5, and written representations that no Form 5 was required, which such persons submitted to Alleghany during or with respect to 2011. John J. Burns, Jr. filed a Form 4 report on July 12, 2011 reporting, among other things, his indirect acquisition of a total of 1,003 shares of common stock on May 16, 2011 as a result of a gift by Mr. Burns to a trust of which his spouse is sole trustee. Phillip M. Martineau2012. Joseph P. Brandon filed a Form 4 on November 9, 2012 reporting one transaction that occurred on September 3, 2012. Stephen P. Bradley filed a Form 5 on January 22, 2013 reporting one transaction that occurred on April 5, 2011 reporting his purchase of 300 shares on March 11, 2011 and his purchase of 150 shares on March 28, 2011.30, 2012.

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PROPOSALS REQUIRING YOUR VOTEPROPOSAL 1. ELECTION OF DIRECTORS

Proposal 1. Election of Directors

John G. Foos, William K. Lavin, Phillip M. MartineauStephen P. Bradley, Karen Brenner, Thomas S. Johnson and Raymond L. M. WongJames F. Will have been nominated by the Board for election as directors at the 20122013 Annual Meeting, each to serve for a term of three years, until the 20152016 Annual Meeting of Stockholders and until his or her successor is duly elected and qualified. Following the 2012 Annual Meeting, Messrs. Burns and Carmichael, membersEach of the classnominees is a current member of 2012, will no longer serve as directors of Alleghany.the Board and was recommended to the Board for nomination for election to the Board by the Nominating and Governance Committee. Messrs. LavinJohnson and WongWill and Ms. Brenner were last elected by stockholders at the 20092010 Annual Meeting of Stockholders held on April 24, 2009.23, 2010. Mr. Martineau was last elected to the Board at the 2010 Annual Meeting held on April 23, 2010, and has been added by the Board to the class of directors standing for re-election at the 2012 Annual Meeting in order to make the classes of the Board are as nearly equal in size as practicable. Mr. FoosBradley was appointed to the Board as a member of the class of 20122013 upon the closing of the acquisition of Transatlantic on March 6, 2012, in accordance with the terms of the merger agreement, and is standing for election to the Board for the first time at the 20122013 Annual Meeting.

Proxies received from Alleghany stockholders of record will be voted for the election of the four nominees named above as Alleghany directors unless such stockholders indicate otherwise. If any of the foregoing nominees is unable to serve for any reason, which is not anticipated, the shares represented by proxy may be voted for such other person or persons as may be determined by the holders of such proxy unless stockholders indicate otherwise. A nominee for director shall be elected to the Board if such nominee receives the affirmative vote of a majority of the votes cast with respect to the election of such nominee. A majority of votes cast means the number of votes cast “for” a nominee’s election must exceed the number of votes cast “against” the nominee’s election. Abstentions and broker non-votes (see “Information About Voting”) do not count as votes cast “for” or “against” the nominee’s election. Abstentions and broker non-votes will be counted as present at the meeting for quorum purposes.

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The following information includes the age, the year in which first elected as a director of Alleghany, the principal occupation and/or other business experience for the past five years, other public company directorships during the past five years, and the experience, qualifications, attributes and skills of each of the nominees named for election as director, and of each of the other directors of Alleghany. In addition to the information presented below regarding the specific experience, qualifications, attributes and skills that led the Board to the conclusion that each of the nominees named for election as director should be elected as a director of Alleghany, Alleghany believes that each of the nominees, and each of the other directors of Alleghany, has a

reputation for integrity, honesty and for adherence to high ethical standards. Alleghany also believes that each of the nominees named for election as director, and each of the other directors of Alleghany, has demonstrated business acumen and an ability to exercise sound judgment, as well as a commitment to service to Alleghany and to the Board.

Nominees for Election:

John G. Foos Age 62 Director since 2012 Term expires in 2012				Mr. Foos was Chief Financial Officer of Independence Blue Cross, a health insurance company, from 1989 until his retirement in November 2008. In addition, Mr. Foos currently serves as a director of Blue Cross Blue Shield of South Carolina and as a director and Chairman of the Board of Plan Investment Fund. Mr. Foos was a director of Transatlantic prior to March 6, 2012. Mr. Foos’ qualifications to serve on the Alleghany Board include his extensive experience in and knowledge of accounting and finance, which includes service as the Chief Financial Officer of Independence Blue Cross, in addition to his prior experience as a Partner with KPMG LLP, and his financial literacy.
William K. Lavin Age 67 Director since 1992 Chairman of the Audit     Committee Member of the     Compensation     Committee Term expires in 2012				Mr. Lavin has been a financial consultant since October 1994, and currently serves as a director of Artisanal Brands, Inc. Mr. Lavin’s qualifications to serve on the Alleghany Board also include his business experience as an executive with public and private companies, his extensive experience with public and financial accounting matters for such companies, and his financial literacy.

Phillip M. Martineau Age 64 Director since 2009 Member of the Compensation     Committee Member of the     Nominating and     Governance Committee Term expires in 2013				Mr. Martineau has been Chairman, President and Chief Executive Officer of Pittsburgh Corning Corporation and Pittsburgh Corning Europe, building materials companies, since June 2005. Prior to that, Mr. Martineau was Chief Executive Officer and a director of High Voltage Engineering Corporation (“High Voltage”), a designer and manufacturer of power control systems, from December 2004 until February 2005. The Board of Directors of High Voltage hired Mr. Martineau as Chief Executive Officer to lead High Voltage through a restructuring under Chapter 11 of the U.S. Bankruptcy Code, which resulted in its sale to Siemens in February 2005. Mr. Martineau’s qualifications to serve on the Alleghany Board also include his years of executive operational experience with global companies in the materials and manufacturing sectors, particularly his experience as a Chief Executive Officer of such companies, as well as his experience as a director on the boards of directors of other companies.
Raymond L.M. Wong Age 59 Director since 2006 Member of the Audit     Committee Member of the Compensation     Committee Term expires in 2012				Mr. Wong is currently a Managing Director of Spring Mountain Capital, LP, an investment management company which he joined in June 2007. Prior to that, from July 2002 until June 2007, Mr. Wong was the Managing Member of DeFee Lee Pond Capital LLC, a financial advisory and consulting services company. Mr. Wong’s qualifications to serve on the Alleghany Board also include his business experience, particularly his 25 years as a managing director in the investment banking group of Merrill Lynch & Co., Inc., and his financial literacy.

Other Alleghany Directors:Election

Stephen P. Bradley Age 7071 Director since 2012 Member of the Nominating and     Governance Committee Term expires in 2013				Mr. Bradley is currently the William Ziegler Professor of Business Administration Emeritus at the Harvard Business School.School where he has been a professor since 1968. In addition, Mr. Bradley currently serves as a director of CIENA Corp. and of CRICO/Risk Management Foundation. Mr. Bradley was a director of Transatlantic prior to March 6, 2012 and has also previously served as a director of CIENA Corp. and i2 Technologies, Inc.   Mr. Bradley’s qualifications to serve on the Alleghany Board also include his academic experience at the Harvard Business School relating to his work as a professor of competitive and corporate strategy and his considerable experience as a consultant and as a director of public companies.

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Karen Brenner Age 5657 Director since 2009 Member of the Audit     Committee Member of the Nominating and     Governance Committee Term expires in 2013				Ms. Brenner has been aan Executive Director of Law and Business Initiatives at New York University since 2012 and Clinical Professor of Business at the Leonard N. Stern School of Business at New York University since 2008. She teaches professional responsibility in law and business, corporate governance in law and business, and corporate turnarounds in the interdepartmental markets, ethics,transformation and law program.leadership. Ms. Brenner also has been a principal at Brenner & Company, a financial management and advisory firm she founded, since 1998.   Ms. Brenner’s qualifications to serve on the Alleghany Board also include her years of business experience as a Chairman/Chief Executive Officer and/or board member of public and private companies in a wide variety of industries, and as an advisor to private equity firms, venture capital companies, boards of directors and chief executive officers focusing on enhancing value of operating companies, and her experience in corporate governance and management issues.

Thomas S. Johnson Age 7172 Director since 1997 and for 1992-1993 Member of the Compensation     Committee Member of the     Nominating and     Governance Committee Term expires in 2013				Mr. Johnson was Chairman and Chief Executive Officer of GreenPoint Financial Corporation and its subsidiary GreenPoint Bank from 1993 until his retirement on December 31, 2004. In addition, Mr. Johnson currently serves as a director of R.R. Donnelly & Sons Company and The Phoenix Companies, Inc. and served as a director of the Federal Home Loan Mortgage Corporation during the past five years.   Mr. Johnson’s qualifications to serve on the Alleghany Board also include his over 30 years of experience as a financial services industry executive, particularly as Chairman and Chief Executive Officer of GreenPoint Financial Corporation, his experience as a director on the boards of directors of other companies, and his financial literacy.

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James F. Will Age 7374 Director since 1992 MemberChairman of the     Compensation Committee Member of the     Nominating and     Governance Committee Term expires in 2013				Mr. Will was the President of Saint Vincent College from July 2000 until his retirement in June 2006, at which time he was named Vice Chancellor and President Emeritus of Saint Vincent College.   Mr. Will’s qualifications to serve on the Alleghany Board also include his over 20 years of experience as an executive in the steel industry, particularly his tenure as President and Chief Executive Officer of Armco Inc., a steel manufacturing and metals processing company, and his experience as President of Saint Vincent College.

Other Alleghany Directors

Rex D. Adams Age 7273 Director since 1999 Chairman of the     Nominating and     Governance Committee Member of the Audit     Committee Term expires in 2014				Mr. Adams has been a director and Chairman of the Board of Directors of Invesco Ltd., an investment management company, since April 2006, and a director of Invesco Ltd. since 2001. In addition, Mr. Adams has been Dean Emeritus at the Fuqua School of Business at Duke University since December 2004.   Mr. Adams’ qualifications to serve on the Alleghany Board also include his business experience, including over 30 years as an executive of Mobil Corporation, his experience as a director on the boards of directors of other companies, particularly companies in the investment management industry, his financial literacy, his experience as the Dean and as a professor at the Fuqua School of Business at Duke University, and his experience in matters of corporate governance.

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Ian H. Chippendale Age 6364 Director since 2012 Member of the     Compensation Committee Term expires in 2014				Mr. Chippendale is the formerretired Chairman (from September 2003 to December 2006) of RBS Insurance Group, Ltd., an insurance company. In addition, Mr. Chippendale currently serveshas served as a director of HomeServe plc since January 2007 and was a director of Transatlantic prior to March 6, 2012.   Mr. Chippendale’s qualifications to serve on the Alleghany Board includesalso include his insurance industry knowledge and his international experience, including his service as the Chairman of RBS Insurance Group, Ltd.

Weston M. Hicks Age 5556 Director since 2004 Term expires in 2014				Mr. Hicks has been Alleghany’s President and chief executive officer since December 2004. In addition, Mr. Hicks is a director of AllianceBernstein Corporation.   Mr. Hicks’ qualifications to serve on the Alleghany Board also include his years of experience as an executive in the insurance and financial services industry, particularly his experience as Alleghany’s President and chief executive officer during the past seveneight years, and his experience as an analyst of property and casualty insurance companies.
Jefferson W. Kirby Age 5051 Director since 2006 Term expires in 2014				Mr. Kirby has been Chairman of the Board of Alleghany since July 2010. Mr. Kirby has been the Managing Member of Broadfield Capital Management, LLC, an investment advisory services company, since July 2003. Mr. Kirby also currently serves as a director of Somerset Hills Bancorp.   Mr. Kirby’s qualifications to serve on the Alleghany Board also include his over 20 years of experience in financial services and investment management, including his service as a Vice President of Alleghany from 1994 to June 2003 and as an investment manager.

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John G. Foos Age 63 Director since 2012 Member of the Audit     Committee Term expires in 2015				Mr. Foos was Chief Financial Officer of Independence Blue Cross, a health insurance company, from 1989 until his retirement in November 2008. In addition, Mr. Foos currently serves as a director of Blue Cross Blue Shield of South Carolina and served as a director and Chairman of the Board of Plan Investment Fund during the past five years. Mr. Foos was a director of Transatlantic prior to March 6, 2012. Mr. Foos’ qualifications to serve on the Alleghany Board also include his extensive experience in and knowledge of accounting and finance, which includes service as the Chief Financial Officer of Independence Blue Cross, in addition to his prior experience as a Partner with KPMG LLP, and his financial literacy.
William K. Lavin Age 68 Director since 1992 Chairman of the Audit     Committee Member of the     Compensation     Committee Term expires in 2015				Mr. Lavin has been a financial consultant since October 1994, and currently serves as a director of Artisanal Brands, Inc. Mr. Lavin’s qualifications to serve on the Alleghany Board also include his business experience as an executive with public and private companies, his extensive experience with public and financial accounting matters for such companies, and his financial literacy.

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Phillip M. Martineau Age 65 Director since 2009 Member of the Compensation     Committee Member of the     Nominating and     Governance Committee Term expires in 2015				Mr. Martineau has been Chairman, President and Chief Executive Officer of Pittsburgh Corning Corporation and Pittsburgh Corning Europe, building materials companies, since June 2005. Prior to that, Mr. Martineau was Chief Executive Officer and a director of High Voltage Engineering Corporation (“High Voltage”), a designer and manufacturer of power control systems, from December 2004 until February 2005. The Board of Directors of High Voltage hired Mr. Martineau as Chief Executive Officer to lead High Voltage through a restructuring under Chapter 11 of the U.S. Bankruptcy Code, which resulted in its sale to Siemens in February 2005. Mr. Martineau’s qualifications to serve on the Alleghany Board also include his years of executive operational experience with global companies in the materials and manufacturing sectors, particularly his experience as a Chief Executive Officer of such companies, as well as his experience as a director on the boards of directors of other companies.
Raymond L.M. Wong Age 60 Director since 2006 Member of the Audit     Committee Member of the     Compensation     Committee Term expires in 2015				Mr. Wong is currently a Managing Director of Spring Mountain Capital, LP, an investment management company which he joined in 2007. Prior to that, from 2002 until 2007, Mr. Wong was the Managing Member of DeFee Lee Pond Capital LLC, a financial advisory and private investment company. Mr. Wong’s qualifications to serve on the Alleghany Board also include his business experience, particularly his 25 years as a managing director in the investment banking group of Merrill Lynch & Co., Inc., and his financial literacy.

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Compensation of Directors

The information under this heading relates to the compensation during 20112012 of those personsnon-employee directors who served as directors of Alleghanyon the Board at any time during 2011, except for Mr. Hicks, whose compensation is reflected in the Summary Compensation Table on page 66.2012.

20112012 Director Compensation

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Fees Earned or Paid in Cash

EachIn addition to the fees paid to directors for their service on committees, as described below, each director who is not an Alleghany officer or serving as Chairman or Vice Chairman of the Board receives an annual retainer of $40,000, payable in cashcash. The Chairman of the Board receives an annual retainer of $140,000. Arrangements with the Vice Chairman of the Board, including an annual retainer of $200,000, payable in cash, are described below. The Chairman of the Audit Committee receives an annual fee of $30,000, and each other member receives an annual fee of $15,000. The Chairman of the Compensation Committee receives an annual fee of $15,000, and each other member receives an annual fee of $10,000. The Chairman of the Nominating and Governance Committee receives an annual fee of $12,000, and each other member receives an annual fee of $7,000.

Stock Awards and Option Awards

Pursuant to the 2010 Directors’ Plan, each year as of the first business day following the Annual Meeting of Stockholders, each individual who was elected, re-elected or continues as a member of the Board and who is not an employee of Alleghany or any of its subsidiaries receives:

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On May 2, 2011,April 30, 2012, each eligible director received a stock option to purchase 500 shares of common stock at an exercise price of $329.46$341.85 per share and either (i) 250 shares of restricted

common stock or (ii) 250 restricted stock units. Each director is permitted to defer payment of the restricted stock units, and all whole restricted stock units will be paid in the form of whole shares of common stock.

Arrangements with the Former Vice Chairman of the Board

Mr. Burns was Chairman of the Board from January 2, 2007 through June 30, 2010. Subsequent to the election of Mr. Kirby as2010 and Vice Chairman of the Board effectivefrom July 1, 2010 Mr. Burns remained on the Board as Vice Chairman and a director.through April 27, 2012. For his service as Vice Chairman of the Board, Mr. Burns receivesreceived an annual retainer of $200,000 in cash. Mr. Burns previously received an annual retainer of $400,000 in cash for his service as Chairman of the Board. Commencing in 2011, Mr. Burns waived his rights to receive awards under the 2010 Directors’ Plan and any successor plans thereto. Mr. Burns previously received an annual retainer of $400,000 in cash for his service as Chairman of the Board. In 2004, Alleghany established an office in New Canaan, Connecticut which Mr. Burns usesused as his principal office for purposes of attending to Alleghany-related matters. As Mr. Burns also usesused this office to attend to personal matters, since July 1, 2010, Mr. Burns has reimbursed Alleghany for fifty percent of the annual rent and operating costs for this office, amounting to $32,900$15,256 for calendar year 2011.2012 through June 30, 2012. Mr. Burns has indicated to Alleghany his intention to assumeassumed the lease for this office and all associated costs on or prior to July 1, 2012. During the period that Mr. Burns served as Chairman of the Board, he reimbursed Alleghany for twenty-five percent of the annual rent and operating costs for this office.

THE BOARD RECOMMENDS THAT YOU VOTE “FOR” EACH OF THE NOMINEES TO THE BOARD OF DIRECTORS SET FORTH IN THIS PROPOSAL. PROXIES SOLICITED BY THE BOARD WILL BE SO VOTED UNLESS STOCKHOLDERS SPECIFY A CONTRARY VOTE. EACH NOMINEE SHALL BE ELECTED BY THE AFFIRMATIVE VOTE OF A MAJORITY OF THE VOTES CAST WITH RESPECT TO THE ELECTION OF SUCH NOMINEE. A MAJORITY OF VOTES CAST MEANS THE NUMBER OF VOTES CAST “FOR” A NOMINEE’S ELECTION MUST EXCEED THE NUMBER OF VOTES CAST “AGAINST” THE NOMINEE’S ELECTION. ABSTENTIONS AND BROKER NON-VOTES (SEE “INFORMATION ABOUT VOTING”) DO NOT COUNT AS VOTES CAST “FOR” OR “AGAINST” THE NOMINEE’S ELECTION.

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ProposalPROPOSAL 2. Approval of 2012 Long-Term Incentive PlanRATIFICATION OF SELECTION OF

Alleghany’s 2007 LTIP, which provides for awards of long-term incentive compensation to its key employees, will terminate by its terms on the date of the 2012 Annual Meeting. The Board believes it to be in the best interests of Alleghany and its stockholders to adopt a new plan at this time in order to be able to continue to provide long-term incentives to employees who are responsible for Alleghany’s continued success and growth without a gap after the expiration of the 2007 LTIP. Adoption of a new plan at this time will also assure that there will be an adequate supply of shares to fashion appropriate incentives for any new senior level executives. To provide a continuation of those incentives and to assist Allegheny in attracting and retaining executives of experience and ability on a basis competitive with industry practices, the Board has adopted the 2012 Long-Term Incentive Plan, or the “2012 LTIP,” effective upon stockholder approval. The 2012 LTIP permits Alleghany to provide equity-based incentive compensation, payable in stock or cash, of the types commonly known as restricted stock, restricted stock units, stock appreciation rights, performance shares, performance units, phantom stock and stock options, as well as other types of equity-based incentive compensation. No awards may be granted under the 2012 LTIP after the Annual Meeting of Stockholders in 2017.

The following is a summary of the 2012 LTIP and it is qualified in its entirety by reference to the plan, a copy of which is attached as Exhibit A.

Description of the 2012 LTIP

General. The Compensation Committee administers the 2012 LTIP. Each member of the Compensation Committee shall be both an “outside director” within the meaning of Section 162(m) of the Internal Revenue Code of 1986, as amended (the “Code”), and a “non-employee director” within the meaning of Rule 16b-3(b)(3)(i) promulgated under the Securities Exchange Act of 1934, as amended, or successor rule or regulation (the “Exchange Act”). The Compensation Committee has the authority to determine, within the limits of the 2012 LTIP, the individuals to whom awards will be granted, and the type and size of such awards, including any objectives or conditions for earning payment pursuant to such awards.

Participation. The Compensation Committee may select participants in the 2012 LTIP from among employees of Alleghany and its subsidiaries. The term “employee,” as used in the 2012 LTIP, means any person, including any officer, employed by Alleghany or a subsidiary on a salaried basis. The term “subsidiary,” as used in the 2012 LTIP, means any corporation,

partnership or limited liability company, a majority of the total combined voting power of whose stock or other equity interest is beneficially owned, directly or indirectly, by Alleghany. Alleghany and its subsidiaries currently have approximately 1,394 employees.

Awards. Awards available under the 2012 LTIP may be paid in cash and/or shares of Alleghany common stock, and include, but need not be limited to, grants of:

The Compensation Committee also may make awards in any other form deemed by it to be consistent with the purposes of the 2012 LTIP.

Performance-based Compensation/Performance Goals. The Compensation Committee may, but is not required to, grant an award to any participant who is or who becomes a “Covered Employee” within the meaning of Section 162(m) of the Code that is intended to qualify as “performance-based compensation” within the meaning of Section 162(m) of the Code (a “Qualifying Award”). Covered Employees include primarily those officers of the companies who qualify as Named Executive Officers for purposes of the Company’s proxy disclosure and reporting. Compensation in excess of $1 million to a Covered Employee may not be deductible by the Company if such compensation is not “performance based compensation.” In order for the value of awards other than certain stock options and stock appreciation rights under the 2012 LTIP to be performance based compensation, such awards must be conditional upon the achievement of performance goals established by the Compensation Committee in writing not later than the time period required by Section 162(m) of the Code. Such performance goals, which may vary from participant to participant and award to award, may be expressed in terms

of any, but not limited to, the following business criteria: the attainment of specific amounts of, or increases in, one or more of the following:

in each case, whether applicable to Alleghany or any relevant subsidiary or business unit or entity in which Alleghany has a significant investment, or any combination thereof as the Compensation Committee may deem appropriate. Prior to the payment of any Qualifying Award (other than stock options or stock appreciation rights granted at Fair Market Value), the Compensation Committee must certify in writing that the performance goals were satisfied.

Shares of Stock Subject to the Plan. The 2012 LTIP provides for a maximum of 600,000 shares of common stock to be paid to participants under the 2012 LTIP and/or purchased pursuant to stock options granted under the 2012 LTIP, subject to anti-dilution and other adjustments in certain events specified in the 2012 LTIP. In this regard, awards based upon, or measured by, the value or changes in the value of shares of common stock (whether paid in cash or shares of common stock), any shares of common stock retained by Alleghany in satisfaction of a participant’s obligation for withholding taxes, and shares of common stock not issued as a result of a net exercise of a stock option will be treated as shares of common stock paid to participants. If any award is forfeited or otherwise terminates, in whole or part, or if a stock option expires or terminates without being exercised, the shares of common stock with respect to such awards or stock options will remain available under the 2012 LTIP. Shares of common stock that Alleghany issues through the assumption or substitution of outstanding grants in connection with the acquisition of another entity will not reduce the maximum number of shares available under the 2012 LTIP. The shares of common stock available under the 2012 LTIP may be either authorized but unissued shares or shares held by Alleghany as treasury shares, The Compensation Committee may grant a maximum of 50,000 shares of common stock as Qualifying Awards to any participant in any calendar year, subject to anti-dilution and other adjustments in certain events specified in the 2012 LTIP. The maximum number of shares of common stock available for issuance under the 2012 LTIP in respect of awards granted as stock options is 100,000, and the maximum number of shares with respect to which Qualifying Awards may be granted to any participant in any calendar year in the form of stock options (all of which may be granted in the form of incentive stock options) or stock appreciation rights is 10,000, subject, in each case, to anti-dilution and other adjustments in certain events specified in the 2012 LTIP. There is no limit specified in the 2012 LTIP on the amount of cash which may be paid pursuant to awards granted under the 2012 LTIP.

Stock Options. The 2012 LTIP provides that no stock option granted under the 2012 LTIP shall be exercisable more than ten years after its grant and the price at which shares of common stock may be purchased under any such stock option shall not be less than 100 percent of its Fair Market Value, as defined below, on the date of grant. Upon exercise of a stock option, the option price is required to be paid in cash, or, at the discretion of the Compensation Committee, in shares of common stock valued at the Fair Market Value, as defined below, thereof on the date of payment, or in a combination of cash and shares of common stock. The 2012 LTIP authorizes the Compensation Committee, in the event of any tender offer or exchange offer other than by Alleghany for shares of Alleghany common stock, to take such action as it may deem appropriate to enable recipients of outstanding awards to avail themselves of the benefits of such offer, including acceleration of payment or exercise dates and purchase of outstanding stock options.

Fair Market Value. “Fair Market Value” is defined in the 2012 LTIP generally as (i) the closing sales prices of the common stock on the relevant date as reported on the stock exchange or market on which the common stock is primarily traded, or (ii) if no sale is made on such date, then fair market value is the weighted average of the closing sales prices of the common stock on the next preceding day and the next succeeding day on which such sales were made as reported on the stock exchange or market on which the common stock is primarily traded. The per share Fair Market Value of Alleghany’s common stock on March 12, 2012 was $331.80 and the aggregate market value on such date of the 600,000 shares of common stock subject to the 2012 LTIP was $199,080,000.

Transferability. Under the 2012 LTIP, unless otherwise authorized by the Compensation Committee, any cash payment on account of awards under the 2012 LTIP to a deceased participant shall be paid to such beneficiary as has been designated by the participant in writing to the Secretary of Alleghany, or in the absence of such designation and in the case of awards payable in shares of common stock, according to the Participant’s will or the laws of descent and distribution. However, the Compensation Committee may provide that awards granted pursuant to the 2012 LTIP, other than an option granted as an incentive stock option, be transferable without consideration to a participant’s immediate family members (i.e., children, grandchildren or spouse), to trusts for the benefit of such immediate family members, and to partnerships in which such family members are the only partners.

Time and Deferral of Payments. At the time the Committee grants each award under the 2012 LTIP, the Committee will specify in writing the time of the payment of the award. In making any such award, the Committee may permit the participant to elect to receive all or a portion of an award at a later date. Any such deferrals shall be for such periods and upon such other terms as the Committee may determine to be appropriate and shall be reflected in a written agreement in compliance with the requirements of Section 409A of the Code.

Amendment or Termination of the Plan. The Board, without the consent of any participant, may amend or terminate the 2012 LTIP at any time,provided, however, that no such action shall adversely affect any rights or obligations with respect to any awards previously made under the 2012 LTIP, andprovided further, that no such amendment, without approval of the holders of a majority of the shares of common stock voted thereon in person or by proxy, shall:

Federal Income Tax ConsequencesINDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM FOR FISCAL 2013

The grant and payment of awards under the 2012 LTIP may have varying tax consequences to Alleghany and each participant, depending upon the nature of the award and certain other considerations. The following description is a summary of the federal income tax treatment of awards under the 2012 LTIP payable in shares of common stock; because the applicable rules are quite technical, the description is general in nature and does not purport to be complete.

Non-Qualified Stock Options. A participant who is granted a non-qualified stock option under the 2012 LTIP will not recognize any taxable income at the time the option is granted. Upon exercise of the non-qualified option, the participant will recognize ordinary income, and Alleghany will be entitled to a deduction, in an amount equal to the excess of the fair market value on the date of exercise of the shares of common stock acquired upon exercise of the option over the exercise price paid. The participant’s basis for purposes of determining gain or loss on a subsequent disposition of the shares of common stock acquired upon exercise of the option will be the fair market value of those shares on the date the participant exercised the option, and any such subsequent gain or loss will be taxable as a capital gain or loss, short-term or long-term depending upon the participant’s holding period for the shares of common stock. A participant is permitted to pay the exercise price with existing shares. The existing shares will be treated as if exchanged for new shares in the same number in a non-taxable transaction and balance of the shares will be subject to the tax rule outlined above.

Incentive Stock Options.If a participant is granted an option under the 2012 LTIP that constitutes an incentive stock option, the participant will not recognize any taxable income either

at the time the option is granted or upon exercise of the option, provided the participant was an employee of Alleghany or a subsidiary of Alleghany from the date the option was granted until the date of exercise (or exercises the option within three months following a termination of his or her employment). Alleghany will not be entitled to any deduction. However, the excess of the fair market value of the shares of common stock acquired upon exercise of the incentive stock option on the date of exercise over the exercise price paid will be an “item of tax preference” that may subject the participant to alternative minimum tax liability. If the participant does not dispose of the shares of common stock acquired upon exercise of the incentive stock option for at least two years after the incentive stock option was granted and at least one year after the shares were acquired, all gain realized upon the disposition of the shares will be treated as long-term capital gain, and any loss will be treated as long-term capital loss. If these holding periods are met, Alleghany will not be allowed any deduction with respect to the value of the incentive stock option. If the participant disposes of the shares of common stock acquired upon exercise of the incentive stock option within the one-year and two-year periods specified above, the participant will recognize ordinary income, and Alleghany will be entitled to a deduction, in an amount equal to the lesser of (i) the excess of the fair market value on the date of exercise of the shares of common stock acquired over the exercise price paid, or (ii) the gain recognized, provided the shares of common stock were disposed of by sale or exchange. Any amount recognized in excess of the fair market value (on the date of exercise) of the shares of common stock will be taxable as long-term or short-term capital gain, depending upon the participant’s holding period for the shares of common stock.

Other Awards of Common Stock. A participant who is granted any other award entitling the participant to receive shares of common stock will generally not recognize any income upon the grant of the award. However, upon the delivery of any shares of common stock, the participant generally will recognize ordinary income in an amount equal to the fair market value of any common stock received, and Alleghany will be entitled to a deduction equal to the amount recognized by the participant as ordinary income.

If the shares of common stock received by a participant are subject to a substantial risk of forfeiture, then, unless the participant makes the election described below, the participant will not recognize any income on the date that the shares of common stock were received. Instead, the participant will recognize ordinary income in an amount equal to the fair market value of the common stock on the date that the restrictions constituting a substantial risk of forfeiture with respect to such shares lapse (or are deemed to lapse), and Alleghany will be entitled to a deduction equal to the amount recognized by the participant as ordinary income. The participant’s basis for purposes of determining gain or loss on a subsequent disposition of the shares of common stock will be the fair market value of the common stock on the date that the

restrictions constituting a substantial risk of forfeiture with respect to such shares lapsed (or were deemed to lapse), and any subsequent gain or loss will be taxable as a capital gain or loss, short-term or long-term depending upon the participant’s holding period for the shares of common stock.

A participant receiving shares subject to a substantial risk of forfeiture may elect within thirty days after receipt of the shares to recognize ordinary income in an amount equal to the fair market value of such shares (less the amount, if any, paid therefor) as of the date of receipt. In that case, the participant’s basis in the shares of common stock will be the fair market value of the shares on the date that the shares were received, and any subsequent gain or loss will be taxable as a capital gain or loss, short-term or long-term depending upon the participant’s holding period for the shares. However, if the restricted shares of common stock are subsequently forfeited, the participant will not be entitled to any tax deduction. Under the federal income tax laws, shares that are subject to restrictions on resale under Section 16(b) of the Exchange Act are deemed subject to a substantial risk of forfeiture for a prescribed period, notwithstanding any longer period during which resale of such shares may actually be restricted.

Section 162(m) of the Code disallows a deduction to Alleghany for compensation paid to Alleghany’s Covered Employees in excess of $1 million for any taxable year of Alleghany, subject to certain exceptions. Among other exceptions, the deduction limit does not apply to compensation that meets the requirements for “performance-based compensation” and in respect of certain stock options and stock appreciation rights awards granted that constitute Qualifying Awards under the 2012 LTIP are intended to qualify as “performance-based compensation.”

New Plan Benefits

As of the date hereof, no benefits or amounts have been granted, awarded or received under the 2012 LTIP. Any future awards under the 2012 LTIP will be made in the discretion of the Compensation Committee. Thus, it is not possible to determine the benefits that will be received by eligible participants if the 2012 LTIP is approved by our stockholders. Information concerning awards granted during the last fiscal year under the 2007 LTIP is set forth in the table captioned “Grants of Plan-Based Awards in 2011” on page 68, and information regarding outstanding restricted stock and performance shares granted under the 2007 LTIP and under the 2002 LTIP is set forth in the table captioned “Outstanding Equity Awards at 2011 Fiscal Year-End” on page 73.

Equity Compensation Plan Information

The following table summarizes information, as of December 31, 2011, relating to Alleghany’s equity compensation plans under which its equity securities are authorized for issuance:

2005 Directors’ Plan and 2010 Directors’ Plan (the “Director Restricted Stock Units”) are paid out in the form of common stock, with one share of common stock being paid for each Director Restricted Stock Unit. Matching Grant Restricted Stock Units are to be paid in cash and/or common stock, at the discretion of the Compensation Committee, with one share of common stock or, if payment is made in cash, the market value of one share of common stock on the payment date, being paid for each Matching Grant Restricted Stock Unit. Performance shares outstanding under the 2007 LTIP are paid, at the end of a four-year award period, in a maximum amount equal to one and one-half shares of common stock for each performance share, depending upon the level of performance achieved. Payments in respect of performance shares are made based upon the market value of common stock on the payment date. Recipients of performance shares are permitted to elect to receive payment for performance shares in the form of cash and/or common stock, subject to certain limitations. Since there is no exercise price for restricted stock units or for performance shares, they are not taken into account in calculating the weighted-average exercise price in column (b).

Stockholder Approval of the 2012 LTIP

An affirmative vote of a majority of the shares of common stock present in person or represented by proxy and entitled to vote at the 2012 Annual Meeting is required to approve the 2012 LTIP.

A copy of the 2012 LTIP is set forth in full in Exhibit A to this proxy statement. The foregoing description is a summary of some, but not all, of the essential provisions of the 2012 LTIP, and is qualified by reference to the full text of the 2012 LTIP.

THE BOARD RECOMMENDS A VOTE “FOR” THE APPROVAL OF THE 2012 LTIP. PROXIES SOLICITED BY THE BOARD OF DIRECTORS WILL BE SO VOTED UNLESS STOCKHOLDERS SPECIFY A CONTRARY VOTE. THIS PROPOSAL SHALL BE ADOPTED BY THE AFFIRMATIVE VOTE OF A MAJORITY OF THE SHARES OF OUTSTANDING COMMON STOCK PRESENT IN PERSON OR REPRESENTED BY PROXY AT THE 2012 ANNUAL MEETING AND ENTITLED TO VOTE. ABSTENTIONS WILL HAVE THE SAME EFFECT AS A VOTE AGAINST THIS PROPOSAL. BROKER NON-VOTES (SEE “INFORMATION ABOUT VOTING”) WILL NOT BE CONSIDERED AS SHARES ENTITLED TO VOTE WITH RESPECT TO THE APPROVAL OF THE 2012 LTIP AND WILL NOT BE COUNTED AS VOTES CAST “FOR” OR “AGAINST”.

Proposal 3. Ratification of Selection of

Independent Registered Public Accounting Firm for the year 2012

On February 13, 2012, following a competitive process undertaken by the Audit Committee the Audit Committee approved the selection ofhas selected Ernst & Young LLP (“E&Y”) to serve as Alleghany’s independent registered public accounting firm for the fiscal year ending December 31, 2012. Alleghany is submitting a proposal to stockholders at the 2012 Annual Meeting for ratification of this selection.2013. Although ratification by stockholders is not a prerequisite to the ability of the Audit Committee to select E&Y as Alleghany’s independent registered public accounting firm, the Audit Committee and the Board believe that such ratification is desirable. If stockholders do not ratify the selection of E&Y, the Audit Committee will reconsider its selection of an independent registered public accounting firm. The Audit Committee may, however, select E&Y notwithstanding the failure of stockholders to ratify its selection. Alleghany expects that representatives of E&Y will be present at the 2013 Annual Meeting, will have an opportunity to make a statement if they desire to do so, and will be available to respond to appropriate questions.

Change in Independent Registered Public Accounting Firm

On February 13, 2012, following a competitive process undertaken by the Audit Committee, the Audit Committee approved the selection of E&Y to serve as Alleghany’s independent registered public accounting firm for the fiscal year ending December 31, 2012.

Prior to the engagement of E&Y, KPMG LLP (“KPMG”) had been Old Alleghany’s independent auditors from 1947 until its liquidation in 1986 and had been Alleghany’s independent auditors since its incorporation in November 1984.auditors. KPMG was notified on February 13, 2012 that it would not be retained as Alleghany’s independent registered public accounting firm for the fiscal year ending December 31, 2012. KPMG’s engagement as Alleghany’s independent registered public accounting firm to audit Alleghany’s consolidated financial statements for the fiscal year endingended December 31, 2011, was unaffected by the selection of E&Y, as KPMG’s dismissal became effective on February 24, 2012, following the completion of KPMG’s audit of Alleghany’s consolidated financial statements as of and for the fiscal year ended December 31, 2011 and the filing of the related Annual Report on Form 10-K.

The audit reports of KPMG on the consolidated financial statements of Alleghany and its subsidiaries as of and for the years ended December 31, 2011 and 2010 did not contain any adverse opinion or disclaimer of opinion nor were they qualified or modified as to uncertainty, audit scope or accounting principles.

The audit reports of KPMG on the effectiveness of internal control over financial reporting as of December 31, 2011 and 2010 did not contain any adverse opinion or disclaimer of opinion, nor were they qualified or modified as to uncertainty, audit scope, or accounting principles.

During the two fiscal years ended December 31, 2011 and 2010, and the subsequent interim period through the filing of Alleghany’s Form 10-K for the fiscal year ended December 31, 2011 on February 24, 2012, there were (i) no disagreements between Alleghany and KPMG on any matter of accounting principles or practices, financial statement disclosure, or auditing scope or procedures, which, if not resolved to the satisfaction of KPMG, would have caused KPMG to make reference thereto in their reports on the consolidated financial statements for such years, and (ii) no “reportable events” as that term is defined in Item 304(a)(1)(v) of Regulation S-K.

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During the two fiscal years ended December 31, 2011 and 2010, and the subsequent interim period through February 24, 2012, Alleghany did not consult with E&Y regarding either (i) the application of accounting principles to a specified transaction, either completed or proposed; or the type of audit opinion that might be rendered on Alleghany’s consolidated financial statements, and neither a written report was provided to Alleghany nor oral advice was provided that E&Y concluded was an important factor considered by Alleghany in reaching a decision as to the accounting, auditing or financial reporting issue; or (ii) any matter that was either the subject of a “disagreement,” as that term is defined in Item 304(a)(1)(iv) of Regulation S-K and the related instructions to Item 304 of Regulation S-K, or a “reportable event,” as that term is defined in Item 304(a)(1)(v) of Regulation S-K.

Alleghany provided KPMG with a copy of a Form 8-K/A disclosing the above matters, which was filed on February 28, 2012. KPMG furnished Alleghany with a letter addressed to the SEC stating that KPMG agreed with the statements made in the Form 8-K/A, except that KPMG was not in a position to agree or disagree with Alleghany’s statement that E&Y’s engagement was approved by the Audit Committee or with Alleghany’s statement that E&Y was not engaged regarding the application of accounting principles to a specified transaction or the type of audit opinion that might be rendered on Alleghany’s consolidated financial statements, or the effectiveness of internal control over financial reporting. A copy of such letter, dated February 28, 2012, was filed as Exhibit 16 to the Form 8-K/A.

Alleghany expects that representatives of KPMG2012 and E&Y will be present at the 2012 Annual Meeting, will have an opportunity to make a statement if they desire to do so, and will be available to respond to appropriate questions.2011 Fees

The following table summarizes the fees (i) for professional audit services rendered by E&Y for the audit of Alleghany’s 2012 annual consolidated financial statements and (ii) E&Y incurred for other services rendered to Alleghany for 2012. In addition, the table summarizes the fees (i) for professional audit services rendered by KPMG for the audit of Alleghany’s 2011 annual consolidated financial statements and fees(ii) KPMG billedincurred for other services rendered to Alleghany for 2011 and 2010:2011:

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The amounts shown for “Audit Fees” represent the aggregate fees for professional services E&Y and KPMG rendered for the audit of Alleghany’s annual consolidated financial statements for each of the last two fiscal years, the reviews of Alleghany’s financial statements included in its Quarterly Reports on Form 10-Q, and the services provided in connection with statutory and regulatory filings during each of the last two fiscal years. “Audit Fees” also include fees for professional services E&Y and KPMG rendered for the audit of the effectiveness of internal control over financial reporting. The amounts shown for “Audit-Related Fees” represent the aggregate fees E&Y and KPMG billedincurred for each of the last two fiscal years for assurance and related services that are reasonably related to the performance of the audit or review of Alleghany’s financial statements and that are not reported under “Audit Fees.” These services include due diligence assistance in connection with acquisitions, consents and procedures for registration statements, consultations on accounting and audit matters, and review of certain subsidiary material contracts. The amount shownamounts for “All Other“Tax Fees” for 2010 represents the aggregateE&Y represent fees KPMG billed in 2010E&Y incurred for access2012 with respect to its electronic databasetax compliance work for accounting research.Transatlantic. E&Y was engaged to perform such tax compliance work prior to Alleghany’s acquisition of Transatlantic.

Pre-Approval Policies and Procedures

Audit and permissible non-audit services that Alleghany’s independent registered public accounting firm may provide to Alleghany must be pre-approved by the Audit Committee or, between meetings of the Audit Committee, by its Chairman pursuant to authority delegated by the Audit Committee. The Chairman reports all pre-approval decisions made by him at the next meeting of the Audit Committee, and he has undertaken to confer with the Audit Committee to the extent that any engagement for which his pre-approval is sought is expected to generate fees for the independent registered public accounting firm in excess of $100,000. When considering the independence of the independent registered public accounting firm, the Audit Committee

considers, among other matters, whether the provision of non-audit services by the independent registered public accounting firm to Alleghany is compatible with maintaining the independence of the independent registered public accounting firm. All audit and permissible non-audit services rendered in 20112012 and 20102011 were pre-approved pursuant to these procedures.

THE BOARD RECOMMENDS THAT YOU VOTE “FOR” THIS PROPOSAL. PROXIES SOLICITED BY THE BOARD WILL BE SO VOTED UNLESS STOCKHOLDERS SPECIFY A CONTRARY VOTE. THIS PROPOSAL SHALL BE ADOPTED BY THE AFFIRMATIVE VOTE OF A MAJORITY OF THE VOTES CAST ON THIS PROPOSAL.

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Audit Committee Report

The Audit Committee is currently composed of the five independent directors whose names appear at the end of this report. Management is responsible for Alleghany’s internal controls and the financial reporting process. Alleghany’s independent registered public accounting firm is responsible for performing an independent audit of Alleghany’s annual consolidated financial statements in accordance with generally accepted auditing standards and for issuing a report thereon. The Audit Committee’s responsibility is to monitor and review these processes and the activities of Alleghany’s independent registered public accounting firm. The Audit Committee members are not acting as professional accountants or auditors, and their responsibilities are not intended to duplicate or certify the activities of management and the independent registered public accounting firm or to certify the independence of the independent registered public accounting firm under applicable rules.

For fiscal 2011, KPMG2012, Ernst & Young LLP acted as Alleghany’s independent registered public accounting firm. In this context, the Audit Committee has met to review and discuss Alleghany’s audited consolidated financial statements as of December 31, 20112012 and for the fiscal year then ended, including Alleghany’s specific disclosure under management’s discussion and analysis of financial condition and results of operations and critical accounting estimates, with management and KPMGErnst & Young LLP, Alleghany’s independent registered public accounting firm. The Audit Committee has discussed with KPMGErnst & Young LLP the matters required to be discussed by Statement on Auditing Standards No. 61, as amended, as adopted by the Public Company Accounting Oversight Board in Rule 3200T. KPMGErnst & Young LLP reported to the Audit Committee regarding the critical accounting estimates and practices and the estimates and assumptions used by management in the preparation of the audited consolidated financial statements as of December 31, 20112012 and for the fiscal year then ended, all alternative treatments of financial information within generally accepted accounting principles that have been discussed with management, the ramifications of use of such alternative treatments and the treatment preferred by KPMGErnst & Young LLP.

KPMGErnst & Young LLP provided a report to the Audit Committee describing KPMGErnst & Young LLP’s internal quality-control procedures and related matters. KPMGErnst & Young LLP also provided to the Audit Committee the written disclosures and the letter required by the applicable requirements of the Public Company Accounting Oversight Board regarding KPMGErnst & Young LLP’s communications with the Audit Committee concerning independence, and the Audit Committee discussed with KPMGErnst & Young LLP its independence. When considering KPMGErnst Young LLP’s independence, the Audit Committee considered, among other matters, whether KPMGErnst & Young LLP’s provision of non-audit services to Alleghany is compatible with

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maintaining the independence of KPMGErnst & Young LLP. All audit and permissible non-audit services in 20112012 and 20102011 were pre-approved pursuant to these procedures.

Based on the reviews and discussions with management and KPMGErnst & Young LLP referred to above, the Audit Committee has recommended to the Board that the audited consolidated financial statements as of December 31, 20112012 and for the fiscal year then ended be included in Alleghany’s Annual Report on Form 10-K for such fiscal year.

The Audit Committee has selected Ernst & Young LLP as Alleghany’s independent registered public accounting firm for the year 2012, subject to stockholder ratification.

William K. Lavin

Rex D. Adams

Karen Brenner

Dan R. CarmichaelJohn G. Foos

Raymond L.M. Wong

Audit Committee

of the Board of Directors

Proposal 4. Advisory Vote on Executive Compensation

In accordance with Section 14A of the Exchange Act, Alleghany is providing its stockholders with the opportunity to cast an advisory vote on the compensation paid to Alleghany’s named executive officers as reported in this proxy statement. For 2011, our named executive officers were Weston M. Hicks, Roger B. Gorham, Christopher K. Dalrymple, Jerry G. Borrelli, John Carr and our former Senior Vice President — Law, Robert M. Hart, who retired from Alleghany effective April 30, 2011, each of whom is named in the Summary Compensation Table on page 66. As described below in the Compensation Discussion and Analysis section of this proxy statement, we seek to increase book value per share at double digit rates over the long term without employing excessive amounts of financial leverage and without taking risks that we do not deem prudent. We believe that such management of risk is required in order to avoid loss of capital during periods of economic turmoil, even if it results in lower levels of capital appreciation during periods when economic conditions are more favorable. The intent of our executive compensation program is to provide competitive total compensation to our named executive officers on a basis that links their interests with the interests of our stockholders in creating and preserving stockholder value. Although we do not have a policy that a specified percentage of the named executive officers’ compensation be performance-based, our objective is that a significant portion of their compensation be tied to performance objectives. In general, the proportion of the compensation that is performance-based is greater for our more senior named executive officers, reflecting their greater levels of responsibility and associated greater opportunity to contribute to the attainment of our joint objectives of creating and preserving stockholder value.-28-

The primary components of our 2011 compensation program for our named executive officers are summarized below.

Annual Compensation Component		Key Features		Purpose
		Compensation Committee determines individual results for participants and payouts, based on, for more senior named executive officers, overall financial and operational performance of management and, for less senior named executive officers, individual performance.
Long-Term Equity Based Incentives		Grant of performance shares, with number of shares awarded determined as shares having a value at the date of grant equal to a percentage of base salary, which percentage is individually determined by the Compensation Committee for each named executive officer. Performance shares granted for the award period beginning on January 1, 2011 will be paid out on basis of performance over the four-year award period ending December 31, 2014 based on the average annual compound growth in Alleghany’s book value per share, subject to adjustment for performance relative to the S&P 500 Index over the same period.		Provides pay-for-performance component focused on achievement of longer-term objective of increasing book value per share at double digit rates over the long term without employing excessive amounts of financial leverage and without taking risks that we do not deem prudent.
Retirement Benefit		Completion of five years of service is required to receive any retirement benefit and payout of the full retirement benefit requires 15 years of service. Prior to January 1, 2011, the benefit payable under the retirement plan was based		Provides a fixed component of total compensation. Since Alleghany’s senior executives are typically recruited mid-career, assists in attracting senior level talent.

Annual Compensation Component		Key Features		Purpose
		upon a formula that considered both annual base salary and annual cash incentives. Effective January 1, 2011, annual cash incentives earned for years subsequent to 2010 are not considered in the computation of the retirement benefit. Long-term incentives are not taken into account in computing retirement benefits.
Savings Benefit under Deferred Compensation Plan		Annual credit of an amount equal to 15% of base salary.		Provides a stable component of total compensation.

In addition to the components of executive compensation described above, during 2011, Weston M. Hicks, Alleghany’s President and chief executive officer, participated in the ACP Incentive Program, a cash incentive plan that was established by the Compensation Committee under the 2010 MIP in January 2011. In January 2012, the Compensation Committee determined to discontinue the ACP Incentive Program.

Please read the Compensation Discussion and Analysis beginning on page 49 of this proxy statement as well as the Summary Compensation Table and other related compensation tables, notes and narrative appearing on pages 61 through 81 of this proxy statement, which provide detailed information on the compensation of our named executive officers.

The Compensation Committee and the Board believe that Alleghany’s executive compensation program has been designed appropriately and is working to assure that management’s interests are aligned with the interests of Alleghany stockholders. Accordingly, we are asking our stockholders to vote in favor of the following advisory resolution at the 2012 Annual Meeting:

RESOLVED, that the stockholders of Alleghany Corporation (“Alleghany”) approve, on an advisory basis, the compensation of Alleghany’s named executive officers as disclosed pursuant to Item 402 of Securities and Exchange Commission Regulation S-K in the Compensation Discussion and Analysis, the Summary Compensation Table, and the

related compensation tables, notes and narrative set forth in the proxy statement for Alleghany’s 2012 Annual Meeting of Stockholders.

Although this advisory resolution, commonly referred to as a “say-on-pay” resolution, is non-binding on the Board, the Board and the Compensation Committee will review and consider the voting results when making future decisions about our executive compensation program. Abstentions and broker non-votes (see “Information About Voting”) will not be counted in evaluating the results of the vote.

THE BOARD RECOMMENDS THAT YOU VOTE “FOR” THIS PROPOSAL.

All Other Matters That May Come Before the 2012 Annual Meeting

As of the date of this proxy statement, the Board knows of no business that will be presented for consideration at the 2012 Annual Meeting other than that referred to above. As to other business, if any, that may come before the 2012 Annual Meeting, shares represented by proxy will be voted in accordance with the judgment of the person or persons voting the proxies.

EXECUTIVE OFFICERS

The name, age, current position, date elected and five-yearprior business historyexperience of each of Alleghany’s executive officers (the “Named Executive Officers”) is as follows:

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COMPENSATION COMMITTEE REPORT

The Compensation Committee has met to review and discuss with Alleghany’s management the specific disclosure contained under the heading “Compensation Discussion and Analysis and Compensation Matters” appearing on pages 49 through8132 through 71 below. Based on its review and discussions with management regarding such disclosure, the Compensation Committee has recommended to the Board that the Compensation Discussion and Analysis and Compensation Matters be included in this proxy statement and incorporated by reference in Alleghany’s Annual Report on Form 10-K for the year ended December 31, 2011.2012.

Dan R. CarmichaelJames F. Will

Ian H. Chippendale

Thomas S. Johnson

William K. Lavin

Phillip M. Martineau

James F. Will

Raymond L.M. Wong

Compensation Committee

of the Board of Directors

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COMPENSATION DISCUSSION AND ANALYSIS

AND COMPENSATION MATTERS

Compensation Philosophy and General DescriptionPhilosophyand Objectives

We are managed byOur corporate objective is to create stockholder value through the ownership and management of a small professional staff, includinggroup of operating subsidiaries and investments. The intent of our President, our Executive Vice President, two Senior Vice Presidents and four Vice Presidents. Our executive compensation program is administeredto provide competitive total compensation to our Named Executive Officers (as defined on page 29) in a manner that links their interests with the interests of our stockholders in creating and preserving stockholder value. In addition, our compensation program is intended to support our strategic objective of increasing common stockholders’ equity per share at rates of 7-10% over the long term without employing excessive amounts of financial leverage and without taking imprudent risks. This approach enables us to manage risk to avoid loss of capital during periods of economic turmoil, which we believe creates maximum value for stockholders in the long run even if it results in lower levels of capital appreciation during periods when economic conditions are more favorable.

The foundation of our compensation program rests on the following principles that we believe align our compensation program with the interests of our stockholders:

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Components of our 2012 Compensation Table setting forth theProgram

The primary components of our 2012 compensation of Messrs. Hicks, Gorham, Dalrymple, Borrelli, Carr and Robert M. Hart, whoprogram for our Named Executive Officers are summarized below.

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Alleghany Performance in 2012

2012 was our Senior Vice President – Law until April 30, 2011,a transformational year for 2011, 2010 and 2009 as our “Named Executive Officers.” Joseph P. Brandon, who was appointed as Executive Vice President of Alleghany upon the closing ofdue to the acquisition of Transatlantic on March 6, 2012. The acquisition resulted in Alleghany’s entry into the global reinsurance business, a more than doubling of Alleghany’s market capitalization and almost four-fold increase in net invested assets, and a greatly expanded stockholder base. In addition, the acquisition provided our stockholders with a number of strategic and financial benefits, including a more diversified spread of risk, both in terms of type of exposure and geography, and it was immediately highly accretive to our earnings and common stockholders’ equity per share. The impact of the Transatlantic acquisition was reflected in our year-end 2012 results. Despite losses at Transatlantic and RSUI Group, Inc., or “RSUI,” from Super Storm Sandy, our common stockholders’ equity per share at year-end 2012 was $379.13, an increase of 10.8% from common stockholders’ equity per share of $342.12 at year-end 2011.

Additional information regarding Alleghany’s 2012 results, including audited consolidated financial statements, as well as management’s discussion and analysis with respect to 2012 results, is not includedcontained in Alleghany’s Annual Report on Form 10-K for the year ended December 31, 2012, which was filed with the SEC on February 21, 2013. Readers are urged to review such Form 10-K for a more complete discussion of Alleghany’s financial performance.

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Alleghany Long-Term Performance

We believe that Alleghany’s performance is best measured over the long-term. In this regard, the chart below summarizes Alleghany’s performance over the ten-year period from December 31, 2002 to December 31, 2012, with all values indexed to December 31, 2002. During the ten-year period, Alleghany’s common stockholders’ equity per share increased at a compound annual rate of 8.9%, compared with a compound annual rate of return of 7.1% for the S&P 500, and Alleghany’s share price (adjusted for stock dividends) appreciated at a compound annual rate of return of 8.5%.

Alleghany’s performance during this period occurred during a time of re-invention and major change in the focus and geographic scope of Alleghany’s operating subsidiaries. At the time Mr. Hicks joined Alleghany in October 2002, Alleghany consisted of approximately $900 million of cash and liquid investments at the holding company level and $500 million of capital deployed in several U.S.-based operating subsidiaries engaged in disparate businesses, including an industrial minerals business (Alleghany’s largest subsidiary at the time), a steel fastener import and export business, a Midwest-based regional property and casualty insurer, and a

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landowner in the Sacramento, California region. Since then, Alleghany has divested the industrial minerals business and the steel fastener import and export business. In 2012, Alleghany completed the acquisition of Transatlantic. At year-end 2012, Alleghany had approximately $1.0 billion of cash and liquid investments at the holding company level, with approximately $6.4 billion of capital deployed at operating subsidiaries, substantially all of which were engaged in the global reinsurance business and specialty property and casualty insurance business. During this period, stockholders’ equity in Alleghany increased to $6.4 billion at December 31, 2012 from $1.4 billion at December 31, 2002.

Summary of Recent Changes and Adjustments

to Executive Compensation TableProgram in 2013

Subsequent to our acquisition of Transatlantic in March 2012, the Compensation Committee undertook a review of Alleghany’s executive compensation program and is not includedprocess to ensure that it continued to support the objectives and principles discussed on pages 32 and 33. As part of this review, in September 2012 after a competitive process, the Compensation Committee selected a new compensation consultant, Frederic W. Cook & Co, Inc., or “FW Cook.” As part of its determination to select FW Cook, the Compensation Committee reviewed and assessed the independence of FW Cook as a “Named Executive Officer” herein because hefirm and the individuals providing advice to the Compensation Committee. The Compensation Committee determined that FW Cook as a firm and the relevant individual advisers were independent.

At the direction of the Compensation Committee, FW Cook reviewed our executive compensation program and process, including by meeting with the Compensation Committee and with members of management. In December 2012, although FW Cook concluded that our existing compensation program was simple and effective in supporting Alleghany’s compensation philosophy and business strategy, FW Cook recommended some refinements for consideration by the Compensation Committee. After further discussion regarding these recommendations with FW Cook and management, the Compensation Committee at its January 2013 meeting adopted some of the recommendations and took additional actions with respect to our 2013 compensation program. A summary of the significant changes and actions taken by the Compensation Committee which will affect compensation in 2013 and future years, includes:

Annual Incentive Plan

The concept of a target and maximum annual incentive opportunity under the 2010 MIP has been eliminated for all participants in favor of a single target bonus opportunity. This revision removes upside/leverage from the 2010 MIP and recognizes the subjective nature of evaluating

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annual financial and individual performance in a long-term results-oriented company like Alleghany. In addition, in light of the greater volatility and larger catastrophe exposure Transatlantic brings to Alleghany and to parallel the four-year measurement period for performance shares awarded under the 2012 LTIP, the formula used to calculate the level of funding for the MIP Pool was revised to use a four-year, rather than a three-year, average catastrophe loss experience for each of Transatlantic and RSUI.

Long-Term Incentive Plan

For our more senior officers (Messrs. Hicks, Brandon, Dalrymple and Gorham), long-term incentive opportunities in 2013 will continue to be denominated solely in performance shares, the payout of which is based on achievement of the specified performance goal of growth in book value per share. For Mr. Borrelli and other Alleghany officers, 2013 long-term incentive opportunities will be evenly divided between performance shares and shares of time-based restricted stock which cliff-vest four years from date of grant. This move to time-based vesting for a portion of the long-term incentive opportunities for these officers recognizes that they have less ability to impact Alleghany’s overall long-term financial performance, while also providing a retention element to their compensation, particularly in years where performance share payout thresholds are not an executive officermet.

The Compensation Committee also increased the book value per share growth target for performance shares for the 2013-2016 award period to 7% from 6% and increased the threshold percentage below which no payout will be made to 5% from 3.5%. In addition, the Compensation Committee revised the calculation to be used in determining whether the required growth in book value per share has been achieved to eliminate the adjustment for performance relative to the S&P 500 Index (as described on pages 45 and 46).

Finally, the target performance share award for the 2013-2016 award period for Mr. Hicks was increased to 300% of salary from 200% and for Mr. Brandon was increased to 200% from 160%. These target increases reflect the Compensation Committee’s consideration of the transformative increase in size and complexity of Alleghany in 2011.

after the acquisition of Transatlantic, as well as the challenge of achieving a payout of 2013-2016 award period performance shares due to the current low interest rate environment, overall economic volatility, the continuing challenging (re)insurance market conditions, and the tightened performance metrics described above. These target increases will increase the percentage of direct compensation of Mr. Hicks Presidentand Mr. Brandon that is dependent upon Alleghany’s long-term financial performance which the Compensation Committee determined is appropriate in light of Alleghany, is our chief executive officer and chief operating officer. Subject to the control of the Board,their responsibility for such performance.

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For open award periods, Mr. Hicks has direct powerthe following outstanding equity-based awards, consisting of performance share awards made under the 2007 LTIP and authority over2012 LTIP:

See “Long-Term Equity Based Incentive Compensation — 2012 Awards” on pages 44 through 46 for general information regarding the business and affairsterms of Alleghany. Mr. Gorham, Senior Vice President-Finance and Investments, is chief financial officer of Alleghany and his responsibilities include management and oversight of our group-wide fixed income portfolios. Mr. Dalrymple, Senior Vice President, General Counsel and Secretary, is the chief legal officer of Alleghany. His responsibilities include structuring and implementation of business acquisitions and dispositions, assisting the performance shares awarded under Alleghany’s long-term incentive plans.

Compensation Committee with respect to group-wide executive compensation arrangements and advising the Board and its Committees regarding corporate governance matters. Mr. Borrelli, Vice President, is the chief accounting officer of Alleghany and his responsibilities include the development, implementation, and administration of accounting policies and oversight of Alleghany’s accounting and financial controls functions, including as they relate to filings with the SEC and other regulatory reports. Mr. Carr, Vice President, is the Tax Director of Alleghany and his responsibilities include oversight of Alleghany’s core tax compliance, tax planning, and tax accounting functions, including in connection with business acquisitions and dispositions. Mr. Brandon, our Executive Vice President, is primarily responsible for the oversight of Alleghany’s insurance and reinsurance subsidiaries.Process

At our Annual Meeting of Stockholders in April 2011,2012, we conducted our firstan advisory vote on the compensation of our executive officers named in the Summary Compensation Table

included in the proxy statement for our 20112012 Annual Meeting of Stockholders and approximately 98.8%90% of the votes cast on such proposal were voted in favor of the proposal. As the Compensation Committee had already made its determinations regarding 2011 compensation prior to the time of our 2011 Annual Meeting of Stockholders, none of the Committee’s subsequent actions or decisions with respect to the compensation of our executive officers in 2011 was directly attributable to the results of the vote. However, theThe Compensation Committee reviewed the outcome of the 2012 advisory vote and believes that the strong level of support achieved reflects favorably on our executive compensation philosophy. Based on the advisory vote of our shareholdersstockholders at the 2011 Annual Meeting of Stockholders in favor of holding an annual vote on executive compensation, the Board determined that Alleghany will hold stockholder advisory votes on executive compensation every year. The Compensation Committee intends to review the outcome of the 20122013 advisory vote and future advisory votes on the compensation of our Named Executive Officers as one of the relevant factors in structuring our executive compensation program.

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Compensation adjustments and awards are made annually by the Compensation Committee at a meeting in January. Mr. Dalrymple supports the Compensation Committee in its work. In addition to Mr. Dalrymple,Additionally, the Compensation Committee has retained the Compensation Consultant, Grahall Partners,FW Cook as a compensation consultant to assist the Compensation Committee in its review of executive and director compensation practices, including the competitiveness of Alleghany executive salaries,compensation, executive compensation program design matters, market trends and technical considerations. The nature and scope of services that the Compensation ConsultantFW Cook provides to the Compensation Committee include: competitive market compensation analyses, assistance with the redesign of any compensation or benefit programs as necessary or requested, assistance with respect to analyzing the impact of regulatory and/or accounting developments on Alleghany compensation plans and programs, and preparation for and attendance at selected Compensation Committee meetings. The Compensation ConsultantFW Cook is also advisesavailable to advise the Compensation Committee and management on various executive compensation matters involving Alleghany’s operating subsidiaries. The Chairman of the Compensation Committee reviews and approves all services provided by the Compensation ConsultantFW Cook and fees to be paid by Alleghany pays to the Compensation Consultant.

Our corporate objective is to create stockholder value through the ownership and management of a small group of operating subsidiaries and investments. In this regard, we seek to increase book value per share at double digit rates over the long term without employing excessive amounts of financial leverage and without taking risks that we do not deem prudent. We believe that such management of risk is required in order to avoid loss of capital during periods of economic turmoil, even if it results in lower levels of capital appreciation during

periods when economic conditions are more favorable. The intent of our executive compensation program is to provide competitive total compensation to the Named Executive Officers on a basis, as discussed below, that links their interests with the interests of our stockholders in creating and preserving stockholder value.FW Cook.

In evaluating our executive compensation program, the Compensation Committee has been advised from time to time by the Compensation ConsultantFW Cook as to the compensation levels of other companies including companies much larger than ours, that might compete with us for executive talent. Competitive market data have been periodically developed by the Compensation ConsultantFW Cook from several different sources, including proxy statements and various published compensation survey sources regarding various layers of the market to which Alleghany executives might be recruited, including larger companies, private equity and hedge funds.statements. We do not seek to set our executive compensation to any benchmarks or peer group but use the competitive market data to provide insights into our compensation levels, mix and strategies. Our senior officers have all been recruited in mid-career, and our compensation must be reasonably competitive with that of their former employers. However, we do not seek to compete for executive talent solely on the basis of compensation. Rather, we also compete by offering a unique professional opportunity to work in a high integrity environment where the focus is on building long-term stockholder value.

Although we do not have a policy that a specified percentage of the Named Executive Officers’ compensation be performance-based, ourOur objective is that a significant portion of the Named Executive Officers’ compensation be tied to Alleghany’s financial performance. We seek to incentivize achievementperformance without encouraging the use of realistic performance goals without employing excessive financial leverage or undue operating risk.and the taking of imprudent risks. Thus, annual cash incentive compensation under the 2010 MIP and long-term equity-based incentives under the 2002 LTIP, 2007 LTIP and 20072012 LTIP are “capped” at a maximum payout once a certain level of financial performance is attained. If approved by stockholdersattained, and performance goals are set at the 2012 Annual Meeting, any long-term equity-based incentives granted under the 2012 LTIP will be similarly capped at a maximum payout.realistic levels. Finally, we do not grant stock options to our officers. Our goal is to promote risk-adjusted long-term growth in the intrinsic value of our common stock and not just its market price. We believe that over time intrinsic value will be reflected in the market price of our common stock.

The components of compensation paid to the Named Executive Officers in respect of 2011 consisted principally of:

The Compensation Committee determined 20112012 salaries and incentive awards for all of the Named Executive Officers except Mr. Brandon at a meeting in January 2011,2012, which followed a January 20112012 meeting of the Board, at which the Board reviewed and discussed an evaluation of Mr. Hicks’ 2010 performance and priorities for 2011, a report by Mr. Hicks on management succession and development throughout the Alleghany group, the recommendation of Mr. Hicks regarding the individual performance of each Named Executive Officer and Alleghany’s strategic plan for 2011-2015. The Compensation Committee determined payouts of 2011 incentive awards for the Named Executive Officers at a meeting in February 2012, following a January 2012 meeting of the Board, at which the Board discussed and reviewed an evaluation of Mr. Hicks’ 2011 performance and priorities for 2012, a report by Mr. Hicks on management succession and development throughout the Alleghany group, the recommendation of Mr. Hicks regarding the individual performance of each Named Executive Officer except Mr. Brandon, and Alleghany’s strategic plan for 2012-2016. Mr. Brandon’s 2012 salary and incentive awards were negotiated as part of his employment agreement with Alleghany dated as of November 20, 2011, which became effective on March 6, 2012.

In determining Mr. Hicks’ 20112012 compensation, the Compensation Committee reviewed Mr. Hicks’ 20102011 performance and 20112012 priorities, as described above, as well as all components of Mr. Hicks’ 20102011 compensation, including annual salary, annual cash incentive compensation in respect of 20102011 under the 2005 Management Incentive Plan (“2005 MIP”),2010 MIP, long-term incentive compensation under the 2002 LTIP and 2007 LTIP, values of previous awards of restricted stock and benefits under Alleghany’s Deferred Compensation Plan, Alleghany’s Retirement Plan and the medical, long-term disability and other employee welfare plans.

Perquisites

Our general practice is to not provide perquisites or other personal benefits to ourThe Compensation Committee determined payouts of 2012 incentive awards for the Named Executive Officers. In 2011, noOfficers at a meeting in February 2013, following the January 2013 meeting of the Board, at which the Board reviewed and discussed an evaluation of Mr. Hicks’ 2012 performance, the recommendation of Mr. Hicks regarding the individual performance of the other Named Executive Officer received more than $10,000 in perquisites or other personal benefits.Officers, and Alleghany’s financial performance for 2012 and applicable award periods.

Components of Compensation

The components of compensation paid to the Named Executive Officers in respect of 2012 consisted principally of:

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Set out below in more detail is a description and analysis of theeach of these components of our compensation program.

Salary

We seek to pay salaries that are sufficiently competitive to attract and retain executive talent. The Compensation Committee generally makes salary adjustments annually, in consultation with the Compensation Consultant,our compensation consultant, based on salaries for the prior year, general inflation, individual performance and internal comparability considerations. In light of continued economic uncertainty, the Compensation Committee and senior management agreed2012, Mr. Hicks received a 25% increase in salary, after taking into account that there would be no 2011his last salary increase for the President, the Senior Vice President — Financehad occurred six years before, his effective leadership during that time, and Investments or the Senior Vice President — Law. Messrs. Borrelli and Carrinternal comparability considerations. Mr. Gorham received 2011no 2012 salary increases of 3% andincrease. Mr. Dalrymple received a salary increase of 19%,18% and Mr. Borrelli received an increase of 5% based upon recommendationsthe recommendation of Mr. Hicks, taking into account general inflation, individual performance, internal comparability considerations and, with respect to Mr. Dalrymple, his increased responsibilities assumed by Mr. Dalrymple.upon his promotion to Senior Vice President.

Annual Cash Incentive Compensation

We generally pay annual cash incentives to the Named Executive Officers under the 2010 MIP. Target annual incentive awards under the 2010 MIP are stated as a percentage of each Named Executive Officer’s base salary. Target annual incentive awards in respect of performance for 20112012 were made to all of the Named Executive Officers except Mr. Brandon by the Compensation Committee on January 18, 2011,27, 2012, and target bonus opportunities were 110% of salary for Mr. Hicks, 65% of salary for each of Messrs. Gorham and Dalrymple and 40% for Messrs. Borrelli and Carr.Mr. Borrelli. Mr. Brandon’s target bonus opportunity of 80% of salary was set forth in his employment agreement with Alleghany. Maximum incentive opportunities for 20112012 were 150% of target awards. Mr. Hart did not participate in the annual incentive program for 2011 due to his pending retirement. The differing target awards as a percentage of salary reflect the Compensation Committee’s determinations of appropriate levels and mix of compensation components taking into account competitive considerations, varying levels of responsibility within Alleghany, internal comparability and the implicit impact of the various Named Executive Officer levels on the accomplishment of our financial, strategic and operational objectives.

For 2011,2012, payout of awards under the 2010 MIP to our most senior named executive officers,Named Executive Officers, Messrs. Hicks, Brandon, Dalrymple and Gorham, was tied to the achievement of specified financial performance objectives subject to reduction in respect of Alleghany performance and/or individual performance. The 20112012 financial performance goal established by the Compensation Committee for annual incentive awards to Messrs. Hicks, Brandon, Dalrymple

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and Gorham under the 2010 MIP was based on a funding approach, with a 2011 Incentive Pool2012 incentive pool to consist of 4% of 20112012 earnings before income taxes, as reported in Alleghany’s audited financial statements, excluding effects of accounting changes, charges for goodwill or intangibles impairment (including other than temporary impairment charges), expenses incurred in connection with actual and potential

acquisitions, and after deduction of average catastrophe losses of (i) RSUI, Group, Inc., Alleghany’s principal insurance subsidiary, (“RSUI”), for 2008-20102009-2011 of $43.9 million (the “RSUI CAT Average”), but excluding RSUI catastrophe losses in excess of the RSUI CAT Average and (ii) Transatlantic, Alleghany’s principal reinsurance subsidiary, for 2009-2011 of $349.5 million (the “2011“TRH CAT Average”), but excluding TRH catastrophe losses in excess of the TRH CAT Average (the “2012 Incentive Pool”). The use of the RSUI CAT Average and TRH CAT Average rather than the actual amount of RSUI and Transatlantic catastrophe losses in determining the amount of the 2011 Incentive Pool2012 incentive pool was based upon the Compensation Committee’s acknowledgement that RSUI is aand Transatlantic are significant writerwriters of catastrophe exposed property (re)insurance and that management cannot predict the occurrence or severity of catastrophe losses in any particular year.

Based upon our 2011 Plan, 4% of our 2011 earnings before income taxes, adjusted to set RSUI catastrophe losses at the RSUI CAT Average, was $3.3 million. The Compensation Committee set the aggregate maximum for all payouts of awards made in respect of the 20112012 Incentive Pool at $2.2$4.3 million.

For 2012, 4% of our earnings before income taxes, adjusted to set RSUI catastrophe losses at the RSUI CAT Average and Transatlantic catastrophe losses at the TRH CAT Average, was $32.6 million. Such amount exceeded the $4.3 million allowing a cushion to provide it with more flexibility when evaluating 2011 results.aggregate maximum for all payouts of awards made in respect of the 2012 Incentive Pool set by the Compensation Committee in January 2012, so the total amount paid in respect of such awards was capped at $4.3 million. As required for an award intended to be a qualifying award under Section 162(m) of the Internal Revenue Code of 1986, as amended (the “Code”), each of Messrs. Hicks, Brandon, Dalrymple and Gorham was allocated an interest in the 20112012 Incentive Pool based upon his target award as a percentage of the aggregate target awards in respect of the 20112012 Incentive Pool. Thus, for 20102012 MIP awards made to Messrs. Hicks, Brandon, Dalrymple and Gorham, financial performance was based upon the 20112012 Incentive Pool (as defined above) with the Compensation Committee specifically empowered to reduce awards, individually or in the aggregate, in its discretion and in any amount, based on its evaluation of the overall financial and operational performance of Messrs. Hicks, Brandon, Dalrymple and Gorham and their individual performance.

Based on actual 2011 results, the amount of the 2011 Incentive Pool was $9.7 million, which exceeded the $2.2 million aggregate maximum set by the Compensation Committee for the 2011 Incentive Pool when it made awards to Messrs. Hicks and Gorham under the 2010 MIP in January 2011. At its meeting on February 23, 2012,21, 2013, the Compensation Committee determined thatevaluated the goals for 2011 Incentive Pool awards to Messrs. Hicks and Gorham were achieved for maximum payout. The Compensation Committee then evaluated individual performance of the President, the President’sMr. Hicks, Mr. Hicks’ recommendation regarding the individual performance of Mr.Messrs. Brandon, Dalrymple and Gorham, and Alleghany’s overall corporate performance. Regarding individual performance, Mr. Hicks’ recommendations reflected the substantial work that Messrs. Brandon, Dalrymple and Gorham had done in 2012 with respect to completing the

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Transatlantic acquisition, integrating the Transatlantic operations with those of Alleghany, particularly with respect to finance, legal and investment oversight, and superior performance in their areas of primary responsibility. With respect to Mr. Hicks’ individual performance, the Compensation Committee noted his leadership in completing the Transatlantic acquisition, his overall responsibility for the successful integration of Transatlantic and superior work with Alleghany’s expanded stockholder base and investor relations development. Following such evaluation, the Compensation Committee authorized individual payouts of 20112012 Incentive Pool awards to Messrs. Hicks, Brandon, Dalrymple and Gorham.Gorham in an aggregate amount equal to the $4.3 million maximum available award payout.

Payouts of awards under the 2010 MIP for 2011 for our Named Executive Officers at the Vice President level, Messrs. Dalrymple,For 2012, Mr. Borrelli and Carr, were based on individual performance goals for each particular Named Executive Officer reflecting his primary area of responsibility (as discussed(who did not participate in the second paragraph of the Compensation Discussion and

Analysis above). As described above, each of Messrs. Dalrymple, Borrelli and Carr2012 Incentive Pool) was assigned a target bonus opportunity as a percentage of salary under the 2010 MIP, with a maximum incentive opportunitiesopportunity equal to 150% of his target awards.award. Payout of the award under the 2010 MIP for 2012 for Mr. Borrelli was based on individual performance goals relating to his primary responsibilities including the development, implementation, and administration of accounting policies and oversight of Alleghany’s accounting and financial controls functions, including as they relate to filings with the SEC and other regulatory reports. At its meeting on February 23, 2012,21, 2013, the Compensation Committee evaluated the President’s recommendationsMr. Hicks’ recommendation regarding theMr. Borrelli’s superior individual performance of each of Messrs. Dalrymple, Borrelli and Carr.with respect to his primary responsibilities, particularly with respect to integrating Transatlantic’s financial reporting function. Following such evaluation, the Compensation Committee authorized individual payoutspayout of 2011 awardsa 2012 award under the 2010 MIP to Messrs. Dalrymple,Mr. Borrelli. The award to Mr. Borrelli and Carr. Awards to Messrs. Dalrymple, Borrelli and Carr for 20112012 under the 2010 MIP werewas not intended to be a qualifying awardsaward for purposes of Section 162(m) of the Code.

Annual cash incentives for 20122013 under the 2010 MIP will be paid pursuant to target awards established by the Compensation Committee for the Named Executive Officers in January 2012.2013.

Long-Term Equity Based Incentive Compensation

2011 Awards

We payIn 2012, we made awards of long-term incentive compensation to the Named Executive Officers under our 2002 LTIP and 2007 LTIP, and we intend to continue to pay long-term incentive compensation under our 2012 LTIP, if it is approved by stockholders at the 2012 Annual Meeting. The provisions of the 2007 LTIP are essentially the same as the provisions of the 2002 LTIP and the provisions of the 2012 LTIP being submitted to stockholders for approval at the 2012 Annual Meeting are essentially the same as the provisions of the 2007 LTIP. The 2002 LTIP expired on December 31, 2006 and in December 2006, the Board adopted the 2007 LTIP which was approved by our stockholders at the 2007 Annual Meeting. The 2007 LTIP will expire by its terms at the 2012 Annual Meeting and we have submitted the 2012 LTIP for stockholder approval at the 2012 Annual Meeting. Historically, long-term incentive awards have been made in the form of performance shares and, in a few cases, performance-based restricted stock, and have been structured in a manner intended to qualify as performance-based for purposes of Section 162(m) of the Internal Revenue CodeCode. The 2007 LTIP expired by its terms in April 2012, and stockholders approved the 2012 LTIP, the provisions of 1986,which are essentially the same as amended (the “Code”). the provisions of the 2007 LTIP, at the 2012 Annual Meeting of Stockholders.

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For the 2011-20142012-2015 award period, the Compensation Committee based the number of performance shares awarded to theeach Named Executive OfficersOfficer upon a percentage of such executive officer’s 20112012 salary divided by the average closing price of our common stock for the 30-day period prior to the mailing of material for the meeting of the Compensation Committee at which such awards were made. Such percentages of 20112012 salary were 200% for Mr. Hicks, 160% for Mr. Brandon, 120% for each of Mr. Dalrymple and Mr. Gorham and 60% for each of Messrs. Dalrymple, Borrelli and Carr. Mr. Hart did not participate in the 2011-2014 long-term incentive program due to his pending retirement.Borrelli. The differing target awards as a percentage of salary reflect the Compensation Committee’s determinations of

appropriate levels and mix of compensation components taking into account competitive considerations, varying levels of responsibility within Alleghany, internal comparability and the implicit impact of the various Named Executive Officer levelsOfficers on the accomplishment of our financial, strategic and operational objectives.

Long-term incentive awards under the 2002 LTIP and 2007 LTIP (and future awards that may be made under the 2012 LTIP, if approved by stockholders at the 2012 Annual Meeting), includingIn making awards for the award2012-2015 period, beginning January 1, 2011, are intended to promote accomplishmentthe Compensation Committee took account of our stated principal(i) Alleghany’s financial objective to grow Alleghany’sof increasing book value per share at rates of common stock at double digit rates7-10% over the long-termlong term without employing excessive amounts of financial leverage and without taking imprudent risks, that we do not deem prudent. Although our long-term goal is double digit growth in book value, the Compensation Committee seeks to incentivize achievement of performance goals that are realistic under prevailing conditions and avoid incenting excess risk.

In making awards for the 2011-2014 period, the Compensation Committee at its meeting on January 18, 2011 took account of such stated financial objective and(ii) prevailing financial and economic conditions and uncertainties and (iii) the alignment of performance goals with Alleghany’s near-term strategy, with a particular emphasis on avoiding excess risk and maintaining Alleghany’s financial strength. Taking into account such conditions, Alleghany’s strategy, the prevailing 10-year U.S. Treasury rates and prevailing equity risk premiums adjusted for Alleghany’s estimated stock volatility relative to the market, the Compensation Committee set the following performance goals for the 2011-20142012-2015 awards:

ProvidedWith regard to performance shares awarded for the 2012-2015 period, provided that theAlleghany’s average compound annual growth in Book Value Per Share for the 2011-20142012-2015 period as adjusted for stock dividends, is positive, it will be adjusted to include the excess, if any, of such average annual compound growth over the Total Return on the S&P 500 Index (whether positive or negative and

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as calculated by Bloomberg Finance) for such period. In setting the 2011-2014 performance share awards, the Compensation Committee considered that the awards should be appropriately adjusted for relative protection of stockholder value during periods of unusual financial market turmoil, maintenance of Alleghany’s financial strength and should avoid incenting excess risk taking. To the extent that the Total Return on the S&P 500 Index over a four-year period measures the U.S. earnings environment, growth in Alleghany’s Book Value Per Share at a greater rate may be considered a measure of Alleghany’s performance in preserving stockholder value. Since performance share awards are capped and tied to stock price, the Compensation Committee considered that the relative performance adjustment should not create any disconnect with Alleghany’s goal of increasing stockholder value. In this regard,This relative performance adjustment based on comparison with the Compensation Committee considered that it has authority to exercise its negative discretion to reduce payouts in the event that it determines thatTotal Return on the S&P 500 Index adjustment produces payouts inconsistent with Alleghany’s performance.

ACP Incentive Program

At a meeting on January 18, 2011,was eliminated for performance share awards made by the Compensation Committee establishedin January 2013 for the ACP Incentive Program pursuant2013-2016 award period.

Perquisites

Our general practice is to the 2010 MIP. The purpose of the ACP Incentive Program wasnot provide perquisites or other personal benefits to provide cash incentives to select officers of Alleghany and the investment personnel of our subsidiary Alleghany Capital Partners LLC, a wholly-owned subsidiary of Alleghany (“ACP”), the employees of which are responsible, under the supervision of Mr. Hicks, for group-wide equity investments of Alleghany and its subsidiaries. Pursuant to the ACP Incentive Program, a 2011 ACP Incentive Pool was created equal to 5% of the amount by which (a) the performance of a designated portfolio, with an aggregate value of approximately $1.5 billion, of public equities and cash investments held by Alleghany and its subsidiaries and managed by ACP exceeded (b) the performance that would have been achieved if the designated portfolio had a total return equal to the total return of the S&P 500, over the three-year period from January 1, 2011 through December 31, 2013 (the “2011 ACP Incentive Pool”). Mr. Hicks was granted a 50% interest in the 2011 ACP Incentive Pool. Payouts in respect of the 2011 ACP Incentive Pool were subject to certain caps, including a cap of $1 million for interim payments in respect of calendar year 2011. No otherNamed Executive Officers. In 2012, no Named Executive Officer participatedreceived more than $10,000 in the ACP Incentive Program.

At a meeting held on January 17, 2012, the Compensation Committee determined to discontinue the ACP Incentive Program and to make interim pro rata payments to the

participants in the 2011 ACP Incentive Pool based upon performance through December 31, 2011. At its meeting on February 23, 2012, the Compensation Committee determined that, based upon performance through December 31, 2011, the maximum interim payment of $1 million for calendar year 2011 had been achieved. No further payments will be made in respect of the 2011 ACP Incentive Poolperquisites or under the ACP Incentive Program.other personal benefits.

Compensation Policies and Practices Relating to Risk Management

Risk analysis has always been part of Alleghany’s review and design of its group-wide executive incentive plans, and the Compensation Committee regularly monitors compensation policies, practices and outstanding awards to determine whether its risk management and incentive objectives are being met with respect to group-wide employee incentives. Alleghany’s material risks include investment risk (debt and equity), as well as catastrophe losses and material mispricing of risk at Alleghany’s insurance and reinsurance subsidiaries. The Board’s and management’s risk oversight is discussed on pagepages 3 and 4. The Compensation Committee does not believe that risks arising from Alleghany’s group-wide compensation policies and practices for its employees are reasonably likely to have a material adverse effect on Alleghany. AsIn this regard, as discussed above,on page 32, Alleghany’s annual incentivesshort and performance shareslong-term incentive plans are capped and areat individual levels so not intended to incent excessimprudent risk taking to achieve outsized payouts. In addition, Alleghany officers are required to own a substantial amount of common stock to ensure that they maintain a significant stake in Alleghany’s long-term success, Alleghany also has in place a compensation clawback policy applicable to its officers to further discourage imprudent risk taking, and Alleghany does not grant stock options to officers as it does not wish to reward or punish them for exogenous short-term market price movements. The managements of Alleghany’s insurance and reinsurance subsidiaries are incented to write profitable business and have no incentives to grow premium volume by underpricing risk. The Compensation Committee seeks to set realistic

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incentive goals, monitors them in light of economic conditions and Alleghany’s strategy and risk tolerance, and will consider appropriate adjustments in respect thereof in the event of any conflict between incentives and the Board’s strategy and risk tolerance.

Retirement Plan

We offer retirement plan benefits to all our employees. Retirement benefits for our Named Executive Officers are provided under the Retirement Plan. We believe the Retirement Plan provides a competitive advantage in helping Alleghany attract senior “mid-career” levelsenior-level talent. In addition, the benefits offered by the Retirement Plan provide an important stable component of total compensation. Under the Retirement Plan, a participant must have completed five years of service with Alleghany or a subsidiary of Alleghany before he or she is vested in, and thus has a right to receive, any retirement benefits following his or her termination of employment. Prior to January 1, 2011, the annual retirement benefit under the Retirement Plan, if paid in the form of a joint and survivor life annuity to a married participant who retires on reaching age 65 with 15 or more years of service, was equal to 67% of the participant’s highest average annual base

salary and annual cash bonus over a consecutive three-year period during the last ten years or, if shorter, the full calendar years of employment. On December 13, 2010, pursuant to authority delegated by the Board, the Compensation Committee amended the Retirement Plan, effective January 1, 2011, by eliminating the inclusion of annual cash bonuses earned for years subsequent to 2010 in the computation of benefits. As amended, the annual retirement benefit would be the greater of (a)(i) the retirement benefit accrued by the participant at December 31, 2010, based upon eligibility for vesting and years of service credited at such date, pursuant to the benefit formula in effect at December 31, 2010, or (b)(ii) a full service retirement benefit, if paid in the form of a joint and survivor annuity to a married participant who retires on reaching age 65 with 15 or more years of service, equal to 67% of the participant’s highest average annual base salary over a consecutive three-year period during the last ten years or, if shorter, the full calendar years of employment. Long-term incentives are not taken into account in computing retirement benefits.

Deferred Compensation Plan

Alleghany credits an amount equal to 15% of a Named Executive Officer’s base salary to the Deferred Compensation Plan each year. Entitlement to this savings benefit is not based on performance. As it is Alleghany’s intention that a significant portion of compensation for our Named Executive Officers be contingent on performance objectives, the savings benefit offered by the Deferred Compensation Plan provides a stable component of total compensation. In addition, the Deferred Compensation Plan permits our Named Executive Officers to elect to

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defer the receipt, and thus the taxation, of all or part of their base salary and their annual cash bonus. A participant may choose to have savings benefit credit amounts and deferred salary and bonus amounts either credited with interest, or treated as though invested in our common stock or commencing January 1, 2011, a participant may also elect to have savings benefit credit amounts and deferred salary and bonus amount increased or decreased by an amount proportionate to the growth or decline in our stockholders’ equity per share.

Financial Statement Restatements

It is our Board’s policy that the Compensation Committee will, to the extent permitted by governing law, have the sole and absolute authority to make retroactive adjustments to any cash or equity basedequity-based incentive compensation awarded or paid to any of our officers where the award or payment was predicated upon the achievement of performance measuresgoals that were subsequently the subject of a restatementrestated or otherwise adjusted in a manner that would reduce the size of any such award or payment. In this regard, the Compensation Committee is

authorized to have Alleghany seek to recover any amount the Compensation Committee determines was inappropriately received by any officer.

Executive Officer Stock Ownership Guidelines

We expect our executive officers to achieve ownership of our common stock, having an aggregate value (based upon the higher of market value or book value) equal to a multiple of base salary, as follows: for our President and chief executive officer, the multiple is five times base salary; for our Executive Vice President, the multiple is four times base salary; for Senior Vice Presidents, the multiple is three times base salary; and for Vice Presidents, the multiple is one times base salary. We expect our executive officers to retain 75% of the shares of common stock they receive (net of taxes) in respect of awardsawarded under our long-term incentive plans until they achieve their applicable ownership levels, and they are expected to maintain such levels thereafter.

Tax Considerations

We are not allowed a deduction under the Code for any compensation paid to a “covered employee” in excess of $1.0 million per year, subject to certain exceptions. In general, “covered employees” include our President and our three other most highly compensated executive officers (not including our chief financial officer) who are in our employ and are officers at the end of the tax year. Among other exceptions, the deduction limit does not apply to compensation

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that meets the specified requirements under Section 162(m) of the Code for “performance-based compensation.” In general, those requirements include the establishment of objective performance goals for the payment of such compensation by a committee of the board of directors composed solely of two or more outside directors, stockholder approval of the material terms of such compensation prior to payment, and certification by the committee that the performance goals have been achieved prior to the payment of such compensation. Such requirements permit the committee administering the plan to make discretionary adjustments to performance goals that would reduce payouts but do not permit discretionary adjustments to performance goals that would increase payouts.

Although the Compensation Committee believes that establishing appropriate compensation arrangements to retain and incentivizeincent our executive officers best serves our interests and the interests of our stockholders, the Compensation Committee also believes that, when appropriate, consideration should be given to seeking to maximize the deductibility of the compensation paid to our executive officers.

The 2010 MIP permits the Compensation Committee to grant awards that are intended to qualify as “performance-based compensation” for purposes of Section 162(m) of the Code (“qualifying awards”) and awards that are not intended to qualify as “performance-based” compensation (“non-qualifying awards”). Consistent with the 2010 MIP and the Compensation Committee’s consideration and balancing of its executive compensation objectives, the amounts identified under the Non-Equity Incentive Plan column of the Summary Compensation Table on page 6650 paid to Messrs. Hicks, Brandon, Dalrymple and Gorham for 2012, Messrs. Hicks and Gorham for 2011 and for all Named Executive Officers for 2010 and 2009 are intended to qualify as “performance-based compensation” for purposes of Section 162(m) of the Code. The amounts reflected in such column for Messrs. Dalrymple Borrelli and CarrBorrelli for 2011, as well as the cash bonuses paid to Mr. Borrelli for 2011 and to Mr. Dalrymple for 2010 identified under the Bonus column of the Summary Compensation Table, do not qualify as “performance-based compensation” for purposes of Section 162(m). All of the performance shares awarded to the Named Executive Officers, as well as restricted stock awards to such officers, under the 2002 LTIP, and the 2007 LTIP (and any future awards that may be made under theand 2012 LTIP if approved by stockholders at the 2012 Annual Meeting) are intended to quality as “performance-based” compensation for purposes of Section 162(m).

PAYMENTS UPON TERMINATION OF EMPLOYMENT

Certain of our Named Executive Officers would be entitled to payments in the event of the termination of their employment. These payments, other than those that do not discriminate in scope, terms or operation in favor of the Named Executive Officers and that are generally available to all salaried employees, are described below.Code.

Pursuant to his employment agreement with Alleghany, Mr. Hicks would be entitled to receive continued payments of his base salary until such payments aggregate $1.0 million on a gross basis, payable in accordance with our normal payroll and procedures, following termination of his employment other than for Cause or in the event of his death or Total Disability. As described in more detail on pages 70 through 73, the restricted stock award agreements with Messrs. Hicks and Gorham provide for pro rata payments in the event of termination of employment other than termination for Cause or Total Disability, if certain performance conditions have been met, and the restricted stock unit matching grant award agreement with Mr. Hicks provides for a pro rata payment in the event of the termination of employment without Cause or termination of employment by reason of Mr. Hicks’s death or Total Disability. The foregoing agreements generally define “Cause” to mean conviction of a felony; willful failure to implement reasonable directives of the Chairman or the Board of

Directors of Alleghany, as well as the President in Mr. Gorham’s case, after written notice, which failure is not corrected within ten days following notice thereof; or gross misconduct in connection with the performance of any of their duties. “Total Disability” in the foregoing agreements generally is defined to mean inability to discharge duties due to physical or mental illness or accident for one or more periods totaling six months during any consecutive twelve-month period.

Other than the foregoing, there are no individual arrangements that would provide payments to our Named Executive Officers upon termination other than for cause or in the event of death or disability. Further, we do not have any arrangements with our Named Executive Officers that would provide for payments upon a change of control of Alleghany or upon a change of control and subsequent termination of employment.

A number of the plans described in this proxy statement have provisions that may result in payments upon termination of employment under certain circumstances as described below. Awards under our 2002 LTIP and 2007 LTIP provide for the pro rata payment of outstanding awards in the event of the termination of employment prior to the end of the award period. With respect to awards under the 2002 LTIP and 2007 LTIP, the pro rata payment would be based on the elapsed portion of the award period prior to termination and average annual compound growth in Book Value Per Share through the date of termination, as determined by the Compensation Committee. Awards that may be made under the 2012 LTIP, if approved by stockholders at the 2012 Annual Meeting, would be treated in the same manner.

Our 2010 MIP also provides that, in the event of a participant’s death or disability prior to the end of the award period for an outstanding award, the participant (or in the event of the participant’s death, the participant’s beneficiary) shall receive such portion of the award, if any, as determined by the Compensation Committee in its sole discretion. If the employment of a participant who has received a non-qualifying award is otherwise terminated during an award period, the Compensation Committee, in its sole discretion, may determine that the participant shall be entitled to receive all or any part of the outstanding award payable to such participant. If the employment of a participant who has received a qualifying award is otherwise terminated during an award period, the participant shall not be entitled to receive any payment for such award unless the performance goals applicable to such award are achieved and certified by the Compensation Committee, in which case the Compensation Committee, in its sole discretion, may determine that the participant shall be entitled to receive all or any part of the qualifying award that would be payable to the participant upon the achievement of those performance goals.

Additional payments upon any termination of employment would be made under our Retirement Plan and Executive Retiree Health Plan, or “Post-Retirement Medical Plan,” as long as the employee is eligible to receive benefits under the Retirement Plan at the time of the termination of employment. Our Deferred Compensation Plan also provides for payments of a participant’s vested savings benefit in the event of any termination of employment in the form previously elected by a participant subject to the provisions of Section 409A of the Code, as applicable, or if no election has been made, in a lump sum. A termination of employment will not cause an enhanced payment or other benefit to be made under the Deferred Compensation Plan. Information with respect to the Retirement Plan is set forth on pages 76 through 78, and information with respect to the Deferred Compensation Plan is set forth on pages 79 through 81.

The table below provides information regarding the amounts that Messrs. Hicks, Gorham, Dalrymple, Borrelli and Carr would be eligible to receive upon any termination of employment by Alleghany other than for cause, if such termination of employment occurred on December 31, 2011:

(4)

Reflects payment of all outstanding LTIP awards, including amounts paid in February 2012 for the award period ending December 31, 2011, based on the elapsed portion of the award period prior to termination and average annual compound growth in Book Value Per Share through the date of termination, in accordance with the terms of the awards.

Arrangements with Mr. Hart

Mr. Hart retired as Senior Vice President – Law effective April 30, 2011. As a result of his retirement, Mr. Hart:

Following Mr. Hart’s retirement from Alleghany, he and Alleghany entered into a consulting arrangement covering the period from April 30, 2011 to December 31, 2011. Mr. Hart received cash compensation of $140,000 for the consulting services provided to Alleghany during this period.

EXECUTIVE COMPENSATION

The information under this heading relates to the compensation of Alleghany’s Named Executive Officers during 2012, 2011 2010 and 2009. Alleghany does not use stock options to compensate its employees, including its Named Executive Officers. As a result, all tables contained under this heading “Executive Compensation” omit columns pertaining to stock options.2010.

Summary Compensation Table