It is an honor to serve as iStar's Lead Independent Director. 2019 was an exciting year as we made great progress toward achieving our goals and establishing ourselves as a leader in a new and growing industry. We are gratified that our success rewarded our shareholders with a 64% Total Shareholder Return ("TSR") in 2019. Below are highlights of which our Board and management team are particularly proud. For additional detail, I encourage you to read the letter from Jay Sugarman, our Chairman and CEO, in our Annual Report.

However, before addressing 2019, I'd like to provide some thoughts on the COVID-19 pandemic and the measures iStar is taking to mitigate its impact. The safety and health of our employees and other colleagues are always the highest priority, never more so than now. We have closed all of our offices for the time being and our employees are working from home. We are highly focused on providing a supportive work environment for our people as they adjust to their new "work from home" reality. We are encouraging our employees to observe social distancing protocols. We are also complying with enhanced sanitization measures and other required health and safety steps.

We are maintaining contacts with our business relationships, including tenants, customers, vendors and others, to ensure our business continues to function as effectively as possible during this challenging period. I am proud of the resilience and resolve our team is demonstrating and, with the steps we took last year, believe we will continue moving forward with our strategy once the current crisis abates.

Turning now to our recent progress, detailed below is the three-pronged strategy iStar set forth at the beginning of 2019, along with key accomplishments made throughout the year:

We continued our track record of robust shareholder engagement in 2019. In addition to discussing business strategy, performance, Board oversight and ESG initiatives, we were particularly focused on gathering feedback on executive compensation after the disappointing Say-on-Pay vote at our last two Annual Meetings. For 2019,

our Board and Compensation Committee reached out to shareholders representing nearly 90% of shares outstanding and held discussions with 56% of shares outstanding. We received thoughtful feedback from investors, which was extremely useful and greatly informed the significant changes we have made to directly address shareholders' viewpoints.

I personally participated in 80% of these discussions, many of which were held face to face, along with my fellow Director and Chairman of our Compensation Committee, Barry Ridings. For a detailed discussion of this effort, please read the letter from Barry and our CD&A, which can be found on pages 31 and 34, respectively, of this Proxy Statement.

In a concerted effort to demonstrate responsiveness to shareholder feedback and continue our commitment to a performance-based executive compensation program, the Compensation Committee made a number of meaningful changes to our pay programs:

Director refreshment and Board succession planning have been and continue to be a critical area of focus for our Board. We understand the importance of having the right mix of skills, expertise, and diversity required for oversight of our unique business. We added Richard Lieb to our Board in May 2019 after identifying a need to bring on another director with deep experience in real estate, finance and capital markets. Richard's oversight and contributions have proven invaluable over the last year as we sought to enhance our capital structure and improve our credit quality.

Our Board also identified the need for another director with operational, technology and risk management experience. Anita Sands joined our Board in February 2020 and will stand for election by shareholders at our Annual Meeting. Anita previously served in various senior roles at UBS Financial Services, most recently as Group Managing Director, Head of Change Leadership and a member of the Wealth Management Americas Executive Committee. She is currently on the Board of Pure Storage, Inc. (NYSE: PSTG) and ServiceNow, Inc. (NYSE: NOW).

Moreover, Anita is an internationally known speaker on the future of work, diversity, inclusion and belonging, and leadership for the digital age.

We are proud of all that we accomplished in 2019 and look forward to the exciting challenges ahead. On behalf of the full Board, we are focused on understanding your interests and acting responsibly and thoughtfully to grow and protect your investment. Thank you for your continued investment in and support of iStar.

We cordially invite you to attend our 2016 annual meeting of shareholders. We will hold the meeting at the Harvard Club of New York City, 35 West 44th Street, 3rd Floor, New York, New York 10036 on Wednesday, May 18, 2016 at 9:00 a.m. local time.

At the 2016 annual meeting, Professor John G. McDonald is standing for re-election for the last time, as he has stated that he will retire as a director on December 31, 2016, following more than 17 years of service on our Board. We look forward to continuing to work with Professor McDonald through the current year. We are extremely grateful for his guidance and valuable contributions as a long-standing member of the Board of Directors.

Attached are a notice of meeting and proxy statement that contain information on the proposals to be voted on at the annual meeting and other important matters. We encourage you to read the proxy statement and attachments carefully.

~~YOUR BOARD OF DIRECTORS RECOMMENDS THAT YOU VOTE:~~

Every shareholder vote is important and we encourage you to vote as promptly as possible. All shareholders are invited to attend the annual meeting in person. Any shareholder attending the annual meeting may vote in person even if he or she previously returned a proxy.

As an iStar shareholder, you play an important role in our company by considering and taking action on the matters being presented, as set forth in the attached proxy statement. We appreciate the time and attention you invest in making thoughtful decisions.

~~In addition, at the annual meeting we will transact such other business as may properly come before the meeting or any postponement or adjournment of the meeting.~~

The ~~board~~Board has fixed the close of business on March ~~23, 2016~~20, 2020, as the record date for the determination of shareholders entitled to receive notice of and to vote at the annual meeting or any postponement or adjournment of the meeting.Only holders of record of our common stock ~~par value $0.001 per share,~~ and 8.00% Series D preferred stock ~~par value $0.001 per share,~~ at the close of business on that date will be entitled to vote at the annual meeting.

We are making this proxy statement available to holders of our common stock, par value $0.001 per share, and holders of our 8.00% Series D preferred stock, par value $0.001 per share, on or about April 8, 2016 in connection with the solicitation by our board of directors of proxies to be voted at our 2016 annual meeting of shareholders or at any postponement or adjournment of the annual meeting. Our common stock is listed on the New York Stock Exchange, or the NYSE, and is traded under the symbol “STAR.”

This proxy statement is accompanied by a copy of our Annual Report to Shareholders for the year ended December 31, 2015. Additional copies of the Annual Report, including our financial statements at December 31, 2015, may be obtained from our website at ~~www.istar.com, or by contacting our Investor Relations department at (212) 930‑9400, 1114 Avenue of the Americas, 39~~^th ~~Floor, New York, NY 10036. Copies will be furnished at no additional expense. The~~summary highlights information found on, or accessible through, our website is not incorporated into, and does not form a part of, this proxy statement or any other report or document we file with or furnish to the Securities and Exchange Commission, or the SEC.

Only holders of record of our common stock and our Series D preferred stock at the close of business on March 23, 2016 are entitled to receive notice of and to vote at the annual meeting or at any postponement or adjournment of the meeting. On the record date, there were 75,310,955 shares of common stock and 4,000,000 shares of Series D preferred stock outstanding and entitled to vote.

The presence, either in person or by proxy, of the holders of the outstanding common stock and Series D preferred stock entitled to cast a majority of all the votes entitled to be cast at the meeting, considered as a single class, on the record date is necessary to constitute a quorum at the annual meeting.

~~Each shareholder is entitled to one vote for each share of common stock and 0.25 votes for each share of Series D preferred stock registered in the shareholder’s name on the record date.~~

~~Assuming a quorum is present in person or by proxy at the annual meeting:~~

A “broker non‑vote” occurs when a broker, bank or other nominee returns a properly executed proxy, but indicates on the proxy that it does not have discretionary authority as to certain shares to vote on a particular matter and has not received voting instructions from the beneficial owner of such shares on that matter. Under current NYSE rules, a broker, bank or other nominee does not have discretionary authority to vote shares without specific voting instructions from the beneficial owner on the election of directors (Proposal 1) or the resolution to approve, on a non‑binding, advisory basis, ourGlass Lewis.

The priority topic for off-season outreach this year was executive compensation ~~(Proposal 3). A broker, bank~~and the Chairman of our Compensation Committee and Lead Director participated in 80% of discussions held. For investors who declined outreach or ~~other nominee does, however, have discretionary authority to vote shares without specific voting instructions from the beneficial owner on the ratification~~did not respond, we shared our presentation materials over email for their review.


Proxy Summary · Shareholder Engagement in 2019		iStar Inc. 2020 Proxy Statement\|5

Table of ~~the appointment of the independent registered public accounting firm (Proposal 2).~~

For purposes of votes on all matters described in this proxy statement to be presented at the annual meeting, broker non‑votes and abstentions will not be counted as votes cast and will have no effect on the result of the vote. Both abstentions and broker non‑votes will be considered present for the purpose of determining the presence of a quorum.

If you properly execute a proxy in the accompanying form, and if we receive it prior to voting at the annual meeting, the shares that the proxy represents will be voted in the manner specified on the proxy. If no specification is made, the common stock or Series D preferred stock will be voted FOR the election of directors (Proposal 1), the ratification of the appointment of the independent registered public accounting firm (Proposal 2), the resolution to approve, on a non‑binding, advisory basis, executive compensation (Proposal 3), and as recommended by the board with regard to all other matters in the discretion of the proxy holder.

Votes cast in person or by proxy at the annual meeting will be tabulated by the election inspectors appointed for the meeting, who will determine whether or not a quorum is present. If your shares are held by a broker, bank or other nominee (i.e., in “street name”), you will receive instructions from your nominee which you must follow in order to have your shares voted. Such shareholders who wish to vote in person at the meeting will need to obtain a proxy from the broker, bank or other nominee that holds their shares of record.

~~If you authorize a proxy to vote your shares, you may revoke it at any time before it is voted by:~~

~~We will pay the costs of soliciting proxies from our shareholders.~~ Contents

In addition to ~~solicitation by mail, certain~~providing an update on the evolution of ~~our directors, officers~~iStar's business strategy and ~~regular employees may solicit the return~~compensation program, we discussed a wide variety of ~~proxies by telephone, facsimile, personal interview~~

or otherwise without being paid additional compensation. We will also reimburse brokerage firms and other persons representing the beneficial owners of our shares for their reasonable expenses in forwarding proxy solicitation material to the beneficial owners in accordance with the proxy solicitation rules and regulations of the SEC and the NYSE. Alliance Advisors LLC has been engaged to solicit proxies on our behalf in connectiontopics with our ~~2016 annual meeting~~shareholders in 2019. A summary of key topics discussed is provided in the table below:



		Key Topics				Focus Areas
		Compensation (See the CD&A Summary for more details)				O Structuring CEO compensation program to include an annual bonus (AIP) O Changing / enhancing performance metrics used in AIP O Enhanced transparency of long-term (iPlP) program, including details around the Compensation Committee's process for determining executive compensation

		Governance				O Importance of adding new Directors and expanding Board size O Focus on diversity and mix of skills and experiences O Details around Director search process O Disclosure of a Director skills matrix

		Environmental, Social and Governance (ESG)				O Increased disclosure of ESG initiatives

		Shareholder Outreach				O Increased disclosure around depth and scope of investor outreach, including details of feedback received

Corporate Governance Best Practices

iStar's corporate governance policies and practices support our business and align with best practices.


What we do
	��
	Lead Independent Director with robust role and responsibilities	Annual election of Board members

	Majority Independent Board	Board committees comprised of independent Directors

	Shareholders can call special meetings and amend bylaws	Whistleblower policy

	Majority voting provisions	Robust Director and Committee evaluation process

	Published inaugural ESG Report in 2020


6\|iStar Inc. 2020 Proxy Statement

Table of Contents

Proposal 1—Election of Directors

Our Board of Directors currently has six members. The Board of Directors has nominated all six directors for election at the 2020 Annual Meeting to serve until the 2021 Annual Meeting of shareholders and ~~provide other advisory services for a fee of $27,000, plus expenses.~~

~~At the 2016 annual meeting, seven directors are to be elected to hold office for a term of one year, until the next annual meeting and~~ until their respective successors have been elected and ~~qualified, except that Professor John G. McDonald has informed~~qualified. All current directors were elected at the ~~Company that he will retire as a director on December 31, 2016. In accordance~~2019 Annual Meeting, with the ~~provisions~~exception of Anita Sands, who joined our ~~charter, each member of our board~~Board in February 2020 and is ~~elected annually.~~

~~All~~a nominee for election by the shareholders for the first time.

Each of the nominees ~~for election as a director are presently serving as directors. If a nominee becomes unavailable~~has consented to serve as a director ~~for~~if elected. If, at the time of the Annual Meeting, any ~~reason,~~nominee is unable or declines to serve as a director, the ~~shares represented by any~~discretionary authority provided in the enclosed proxy will be ~~voted~~exercised to vote for ~~the person, if any, who may be~~a substitute candidate designated by the ~~board~~Board of Directors, unless the Board chooses to ~~replace that nominee. At this time, the board~~reduce its own size. The Board of Directors has no reason to believe that any ~~nominee~~of the nominees will be ~~unavailable~~unable or will decline to serve asif elected. Proxies cannot be voted for more than six persons.

We believe that our directors should satisfy several qualifications, including demonstrated integrity, a record of personal accomplishments, a commitment to participation in Board activities and other attributes discussed below in "Director Nominations and Qualifications." We also endeavor to have a Board that represents a range of qualities, skills and depth of experience in areas that are relevant to and contribute to the Board's oversight of the Company's business activities. Following the biographical information for each director ~~if elected.~~

nominee, we describe the key experiences, qualifications, skills and attributes the director nominees bring to the Board that, for reasons discussed in the chart below, are important considering iStar's business and structure. The Board considered these key experiences, qualifications, skills and attributes and the nominees' other qualifications in determining to recommend that they be nominated for election.

All of the nominees, ~~for election as a director,~~ other than Mr. Sugarman, are independent ~~within~~under the standards prescribed by the ~~NYSE.~~

~~The following table sets forth the name, age and the position(s) with us currently held by each person nominated for election as a director:~~

~~Our Nominating~~ (the "Committee") is charged with identifying potential Board members and ~~Governance~~recommending qualified individuals to the Board for its consideration. The Committee ~~believes that our directors should possess~~is authorized to employ third-party search firms to identify potential candidates. In evaluating candidates, the ~~following qualifications:~~

~~The committee endeavors to ensure our board represents a broad range of experience, qualifications, skills~~the Nominating and ~~attributes and, as a whole, reflects an appropriate~~Governance Committee do believe that it is desirable that Board members represent diversity of gender, race and national origin, as well as diversity of viewpoints, background, experience and ~~perspectives.~~ demographics.


Proposal 1—Election of Directors · Director Nominations and Qualifications		iStar Inc. 2020 Proxy Statement\|7

Table of Contents

The Committee generally identifies nominees by first assessing whether the current members of the Board continue to provide the appropriate mix of knowledge, skills, judgment, experience, differing viewpoints and other qualities necessary to the Board's ability to oversee and guide the business and affairs of the organization. The Board generally nominates for re-election current members of the Board who are willing to continue in service, collectively satisfy the criteria listed above and are available to devote enough time and attention to the affairs of the organization. When the Committee seeks new candidates for director roles, it seeks individuals with qualifications that will complement the experience, skills and perspectives of the other members of the Board. The full Board 1) considers candidates that the Committee recommends; 2) considers the optimum size of the Board; 3) determines how to address any vacancies on the Board; and 4) determines the composition of all Board committees.

We believe ~~that the~~our director nominees ~~for election as a director have the qualifications necessary~~are well-equipped to ~~ensure that we are taking appropriate steps to~~oversee management and address the complex issues confronting usiStar as it continues to focus on key strategic objectives, including:

O: becoming the market leader in the ground lease sector
O: increasing the pace at which we monetize our legacy assets
O: continuing to invest our capital where we believe we can capture appropriate risk-adjusted returns

We recently added a ~~challenging business~~new director, Anita Sands, who joined our Board in February 2020 and ~~economic environment. The nominees~~is a nominee for election as a director have held leadership positions in business (and in particular the real estate, investment and financial services business sectors), finance and academia over an extended period of time. Each of the nominees has demonstrated a long record of professional integrity, intellectual acumen, analytic skills, a strong work ethic and the ability to maintain a constructive environment for discussion of matters considered by our ~~board. Additionally, all of our directors have experience as board members of a diverse range of public and private companies.~~

~~Jay Sugarman~~ has served as a director of iStar Inc. (and our predecessor) since 1996 and chief executive officer since 1997. Prior to forming iStar Inc. and its predecessors, Mr. Sugarman managed private investment funds on behalf ofshareholders at the ~~Burden family (a branch of the Vanderbilt family) and the Ziff family. Mr. Sugarman received his undergraduate degree~~ ~~summa cum laude~~ from Princeton University, where he was nominated for valedictorian and received the Paul Volcker Award in Economics, and his M.B.A. with high distinction from Harvard Business School, graduating as a Baker Scholar and recipient of the school’s academic prizes for both finance and marketing. As founder of iStar Inc. and chief executive officer since 1997, Mr. Sugarman has demonstrated the leadership skills and extensive executive experience across a broad range of investment, financial and operational matters that are necessary to lead iStar, a fully‑integrated finance and investment company focused on the commercial real estate industry.

~~Clifford De Souza~~ is the newest member of our board, having served as one of our directors since July 2015. Mr. De Souza is a member of our Audit Committee. Previously, he was chairman of the board of directors and head of international business at Mitsubishi UFJ Securities International, or Mitsubishi, from 2012 to 2014 and served as its chief executive officer from 2008 to 2012. At Mitsubishi, Mr. De Souza was responsible for its securities and investment banking operations and served as the global head of fixed income and commodities for its securities business. From 2005 to 2007, Mr. De Souza served as the chief executive officer and chief investment officer of EMG Investment Management where he managed and developed an alternative asset management business. From 2001 to 2004, Mr. De Souza served as the head of the hedge fund group at Citigroup Alternative Investment where he managed over $40 billion in private equity, real estate, structured product and hedge fund assets. From 1995 to 2000, Mr. De Souza served as global co-head of the UBS Emerging Markets Debt and Currency Trading Franchise where he directed its global secondary debt, derivative, local instrument and foreign exchange trading functions. He holds a B.A. in Physics from the University of Cambridge and a Ph.D. in Theoretical Physics from the University of Maryland. Mr. De Souza’s qualifications for election to our board include his experience as chairman and chief executive officer at Mitsubishi, his involvement and experience leading and developing the management of complex businesses and his in-depth expertise as an investor and allocator of capital.

~~Robert W. Holman, Jr.~~ has served as one of our directors since 1999. He is chairman of our Compensation Committee and a member of our Nominating and Governance Committee. Mr. Holman was co‑founder of TriNet Corporate Realty Trust, Inc., or TriNet, a NYSE‑listed company that we acquired in 1999, and served as its chief executive officer and chairman of the board. He was chief executive officer and chairman of TriNet’s predecessor, Holman/Shidler Corporate Capital, Inc., for ten years. He has structured, acquired, financed and managed several billion dollars of commercial and corporate assets in 40 states and Canada. Mr. Holman co‑founded and was a senior executive and director of Watkins Pacific Corporation, a public multi‑national conglomerate. Mr. Holman currently serves as a director and member of the audit and investment committees of the Parasol Tahoe Community Foundation. Mr. Holman has previously served as a director of Amerivest Properties, Inc., an American Stock Exchange‑listed company, and as a senior executive, director, owner or board advisor for investment and operating companies in the United States, Great Britain, Australia and Mexico. He holds a B.A. degree in international economics from the University of California at Berkeley, an M.A. degree with honors from Lancaster University in England, where he was a British Council Fellow, and did post‑graduate work at Harvard University where he was awarded a Loeb Fellowship. Mr. Holman’s experience as a founder, chief executive and director of TriNet, a public real estate investment firm focused on corporate tenant leasing that remains a key aspect of our business, his involvement in leadership capacities in other companies and

~~organizations engaged in a broad range of business, finance and investment activities and his experience as a private investor all bring valuable skills and qualifications to our board.~~

~~Robin Josephs~~ ~~has served as one of our directors since 1998.~~annual meeting. Ms. Josephs serves as our Lead Director, with duties that include presiding at all executive sessions of the independent directors and serving as principal liaison between the chairman and the independent directors. Ms. Josephs is chair of our Nominating and Governance Committee and a member of our Compensation Committee. From 2005 to 2007, Ms. Josephs was a managing director of Starwood Capital Group L.P., a private equity firm specializing in real estate investments. Previously, Ms. Josephs was a senior executive with Goldman Sachs & Co. in various capacities. She currently serves as a director, chair of the compensation committee and a member of the audit committee of MFA Financial, Inc. (NYSE: MFA), which is primarily engaged in investing in residential mortgage‑backed securities, and as a director and member of the audit committee and compensation committee of QuinStreet, Inc. (NASDAQ: QNST), a vertical marketing and online media company. Ms. Josephs previously served until 2016 as a director and member of the audit and compensation committees of Plum Creek Timber Company, Inc. (NYSE: PCL), which conducted operations in the land, wood products, natural resource and energy businesses. Ms. Josephs is a trustee of the University of Chicago Cancer Research Foundation. Ms. Josephs received a B.S. degree in economics ~~magna cum laude~~ from the Wharton School (Phi Beta Kappa) and an M.B.A. degree from Columbia University. Ms. Josephs’ employment as an investment banking professional brings valuable knowledge of finance and capital markets to our board. Her background working as a managing director of Starwood Capital Group, where she evaluated and managed numerous real estate investments, adds knowledge and expertise in this area of vital importance to our company. Ms. Josephs’ extensive experience as a director of public companies also brings to our board valuable skills and insights into the governance of real estate, investment and operating companies.

~~John G. McDonald~~ has served as one of our directors since 1999. Previously, Professor McDonald served as a director of TriNet from 1993 until we acquired TriNet in 1999. Professor McDonald is a member of our Nominating and Governance Committee and our Compensation Committee. He is the Stanford Investors Professor of Finance in the Graduate School of Business at Stanford University, where he has taught since 1968. Professor McDonald has taught M.B.A. courses and executive programs in subject areas including investment management, private equity, venture capital and corporate finance. He currently serves as a director, a member of the audit committee and chairman of the compensation committee of QuinStreet, Inc. (NASDAQ: QNST), a vertical marketing and online media company. Professor McDonald previously served until 2016 as a director, chairman of the audit committee and a member of the corporate governance and nominating committee of Plum Creek Timber Company, Inc. (NYSE: PCL), until 2014 as a director of Scholastic Corporation (NASDAQ: SCHL), a global children’s publishing, education and media company, until 2012 as a director of 13 mutual funds managed by Capital Research and Management Company, and until 2010 as a director of Varian, Inc. Professor McDonald is an internationally noted finance and investment expert. His background and expertise in equity markets, investment and financial management, entrepreneurial finance, and private equity investing and asset management bringsSands' addition to the ~~board~~Board resulted from a ~~keen understanding of the investor’s perspective of our company~~successful search for a candidate who would bring diversity and ~~its operations. Professor McDonald is standing for re-election at the 2016 annual meeting and has stated that he will retire as a director on December 31, 2016, following more than 17 years of service~~skills valuable to help us execute on our ~~Board.~~go-forward strategy.


8\|iStar Inc. 2020 Proxy Statement

~~Dale Anne Reiss~~

Table of Contents

Candidates for Election as Director

Jay Sugarman

Chairman and Chief Executive Officer, iStar Inc. and Safehold Inc.

Chairman and Directorsince 1996
Age 57

iStar Board Leadership Roles

Chairman

Education:

Princeton University, B.A.

Paul Volcker Award in Economics;summa cum laude; valedictorian nominee

Harvard Business School, M.B.A.

Baker Scholar; Loeb Award in Finance; Copeland Award; Gillette Prize in Marketing

Other Public Company Boards

Safehold Inc.

Select Business Experience

iStar Inc.

Executive Chairman

Safehold Inc., the first public company focused on ground lease investments

Chairman & CEO, June 2017 to present

Select Skills and Qualifications

Business Development & Strategy

Experience building two companies from the ground up as founder and chief executive officer of both iStar and Safehold

Senior Leadership

Serves as CEO of iStar and Safehold, bringing financial, operational and real estate expertise to the Board

Investing

Prior to founding iStar, managed private investment funds on behalf of the Burden family (a branch of the Vanderbilt family) and the Ziff family


Proposal 1—Election of Directors · Candidates for Election as Director		iStar Inc. 2020 Proxy Statement\|9

Table of Contents

Clifford De Souza

Retired Chief Executive Officer, Mitsubishi UFJ Securities International

Independent Directorsince 2015
Age 58

iStar Board Leadership Roles

  Audit Committee Chair
  Investment Committee Member
  Nominating and Governance Committee Member

Education:

Cambridge University, B.A.

University of Maryland, Ph.D.

Other Public Company Boards

None

Select Business Experience

Mistubishi UFJ Securities

Chairman & Head of International Business London, NY, HK, Singapore,

CEO London

Citigroup Alternative Investments

CIO Multi Strategy Hedge Fund Group

Leadership Team -Hedge Fund, Private Equity, Real Estate, and Structured Products

UBS/SBC Warburg Dilion Read

Global Head Emerging Markets

Select Skills and Qualifications

Capital Markets, Business Development, Strategy and Risk Management

At Mitsubishi, responsible for all international securities and investment banking operations including Capital Markets, Secondary Trading, Technology and Operations

At Citigroup, managed over $40 billion in private equity, real estate, structured product, and hedge fund assets

Public Company Executive and Director/Senior Leadership Experience

Chairman—New York, Hong Kong and London MUFG Securities entities, Director NY entity

CEO—London and New York entities

Finance/Accounting

All senior roles required experience with balance sheets, finance and accounting practice


10\|iStar Inc. 2020 Proxy Statement

Table of Contents

Robin Josephs

Former Managing Director, Starwood Capital Group

Lead Independent Director
Independent Director since 1998
Age 59

iStar Board Leadership Roles

  Nominating and Governance Committee Chair
  Compensation Committee Member
  Audit Committee Member

Education:

The Wharton School at the University of Pennsylvania, B.S.

Phi Beta Kappa;magna cum laude

Columbia Business School, M.B.A

Other Public Company Boards

Safehold Inc.

MFA Financial, Inc.

QuinStreet, Inc.

Select Business Experience

Starwood Capital Group, a private equity firm specializing in real estate

Managing Director, 2005 to 2007

Goldman Sachs & Co.

Vice President, Real Estate and Equity Capital Markets, 1986 to 1996

Select Skills and Qualifications

Finance / Accounting

Investment banking and private equity background from roles at Goldman Sachs and Starwood Capital

Capital Markets

Experience as VP of Capital Markets at Goldman Sachs

Real Estate

At Starwood Capital Group, evaluated and managed numerous real estate investments


Proposal 1—Election of Directors · Candidates for Election as Director		iStar Inc. 2020 Proxy Statement\|11

~~has served as one~~Table of ~~our directors since 2008. Ms. Reiss is chair~~Contents

Richard Lieb

Senior Advisor, Greenhill & Co., LLC

Independent Director since 2019
Age 60

iStar Board Leadership Roles

Investment Committee Chair
Compensation Committee Member

Education:

Wesleyan University, B.A.

Phi Beta Kappa

Harvard Business School, M.B.A

Other Public Company Boards

VEREIT, Inc.

AvalonBay Communities, Inc.

CBL Properties, Inc.

Select Business Experience

Greenhill & Co.

Senior Advisor, 2018 to Present

CFO, 2008 to 2012

Chairman of Real Estate, 2005 to 2018

Goldman Sachs & Co.

Head of Real Estate Investment Banking, 2000 to 2005

Select Skills and Qualifications

Finance / Accounting

Served as Greenhill's CFO from 2008 to 2012

Real Estate

More than 30 years of experience focusing on advisory opportunities in the real estate industry

Work has covered the full range of investment banking services for nearly all property sectors, including strategic advisories, IPOs and other securities offerings, asset purchases and sales, property financings, restructurings and M&A


12\|iStar Inc. 2020 Proxy Statement

Table of ~~our Audit Committee. Until her retirement in 2008, she served as Global and Americas~~Contents


		Barry Ridings		Senior Advisor, Lazard Frères & Co. LLC and Chairman, LMDC Holdings LLC
		Independent Director since 2011 Age 68		iStar Board Leadership Roles Compensation Committee Chair Audit Committee Member

Education:

Colgate University, B.A.

Cornell University, Johnson Graduate
School of Management, M.B.A

Other Public Company Boards

Siem Industries, Inc.

Select Business Experience

Lazard Frères & Co.

Senior Advisor, 2015 to Present

Chairman and CEO of LMDC Holdings, 2006 to Present

Chairman and CEO of Lazard Capital Markets, 2006 to 2014

Chairman of LAI Holdings (private equity, technology and real estate funds), 2006 to Present

Vice Chairman of U.S. Investment Banking, 2005 to 2015

Co-head of Restructuring, 1999 to 2015

Chairman of Lazard Middle Market LLC, 2007 to 2019

Fairness Opinion Committee member, 1999 to 2015

Other Current Engagements

Chairman of the Advisory Council, Cornell University Johnson Graduate School of Management

Director, Catholic Charities of the Archdiocese of New York

Select Skills and Qualifications

Finance / Accounting

Over 40 years of experience in investment banking and restructuring at Lazard and BT Alex Brown

Capital Markets

As former Chairman of Lazard Capital Markets, advised on the underwriting of equity and debt offerings, as well as securities trading

Extensive experience in initial public offerings, secondary stock offerings, debt offerings, opinion letters and mergers and acquisitions


Proposal 1—Election of Directors · Candidates for Election as Director		iStar Inc. 2020 Proxy Statement\|13

Table of ~~Real Estate at Ernst & Young LLP, was a Senior Partner there from 1995 through 2008, and subsequently was a senior consultant~~Contents


		Anita Sands		Former Head of Change Leadershp, UBS
		Independent Director since 2020 Age 43		iStar Board Leadership Roles None

Education:

Queens University Beflast, B.S. and Ph.D

Carnegie Mellon University, M.S.

Other Public Company Boards

ServiceNow

Pure Storage

Select Business Experience

UBS

Head of Change Leadership, 2012 to 2013

Chief Operating Officer, UBS Wealth Management, 2010 to 2012

Transformation Consultant, 2009 to 2010

Citigroup

Head of Transformational Management, 2008 to 2009

Select Skills and Qualifications

Technology

At UBS, responsible for technology, operations and corporate shared services, including real estate for 17,000-person division with 7,000 financial advisors and over $1TN in AUM

Operations and Risk Management

At Citigroup, member of Global O&T Operating Committee which oversaw an organization of 140,000 employees and budget in excess of $20B

Business Development & Strategy

As Transformation Consultant at UBS Wealth Management, led the Transformation Program at UBS Wealth Mgt Americas, from strategy and design through to execution


14\|iStar Inc. 2020 Proxy Statement

Table of Contents

Corporate Governance

Board Leadership Structure

In determining the Global Real Estate Center of Ernst & Young LLP from 2008 to 2011. Ms. Reiss serves as Senior Managing Director of Brock Capital Group LLC and Chairperson of Brock Real Estate LLC, its equity and mezzanine financing arm, as well as Managing Director of Artemis Advisors, LLC. Ms. Reiss currently serves as a director and chair of the audit committee of Tutor Perini Corporation (NYSE:TPC), a leading civil and building construction company, as a director and a member of the audit committee of CYS Investments, Inc. (NYSE: CYS), a specialty finance company that invests in residential mortgage‑backed securities, and as a director, chair of the ~~compensation committee and a member of the nominating and governance and executive committees~~ ~~of Care Capital Properties, Inc., a healthcare real estate investment trust with a diversified portfolio of triple-net leased properties~~. ~~Ms. Reiss also serves~~ ~~on the boards of Educational Housing Services, Inc., the Guttmacher Institute and the Police Pension~~appropriate Board ~~of the City of Sanibel, FL.~~ She is a former member of the boards of directors of Post Properties, Inc., where she also served on the audit committee, the Pension Real Estate Association, and ULI-the Urban Land Institute, where she continues to serve as a governor. Ms. Reiss is a Certified Public Accountant. She received a B.S. from the Illinois Institute of Technology and an M.B.A. from the University of Chicago. Ms. Reiss’ qualifications for election to our board include extensive expertise in financial and accounting

matters from her experience over an extended period at several major public accounting firms, her leadership experience in management and operations at those firms and her experience as a director of other public and private companies.

~~Our board has the authority to select the~~ leadership structure it ~~considers appropriate for us. In making leadership structure determinations, the board considers many factors, including the specific needs of our business and what is~~believes will be in the best interests of ~~our shareholders.~~ the organization and shareholders, the Board takes into account a variety of factors, including the business circumstances and needs at a given time. These positions may be held by one individual or by two different individuals. If the Chairman is not an independent director, the Board will designate a lead independent director.

Our current leadership structure consists of a combined ~~chairman~~Chairman of the ~~board~~Board and ~~chief executive officer~~Chief Executive Officer position, aan independent lead ~~independent~~ director, ~~or Lead Director,~~ an active, involved and ~~involved board, a majority~~independent set of ~~which consists of independent~~ directors, and board committees chaired by independent directors.

~~Under~~

Role of the Chairman

Our Board of Directors currently believes it is in our ~~bylaws,~~best interests to have Mr. Sugarman serve as Chairman of our Board of Directors and Chief Executive Officer. When combined with the ~~chairman~~current composition of the ~~board presides over~~Board, the ~~meetings~~use of a lead independent director, and the ~~board and of the shareholders. The chairman of the board shall perform such~~ other ~~duties as may be assigned to him by the board of directors. The chief executive officer has general responsibility for implementation~~elements of our ~~policies, as determined by~~corporate governance structure, the ~~board,~~combined CEO and ~~for the management~~Chairman position strikes an appropriate balance between strong and consistent leadership and independent and effective oversight of our business and affairs. ~~Jay~~

Mr. Sugarman ~~serves~~is an experienced real estate executive and long-time employee with years of board experience. As CEO he has the primary responsibility of developing corporate strategy and managing our day-to-day business operations. As a Board member, he understands the responsibilities and duties of a director and is well positioned to 1) chair regular Board meetings; 2) provide direction to management regarding the needs, interests and opinions of the Board; and 3) help ensure that key business issues and shareholder matters are brought to the attention of the Board. As both CEO and Chairman, Mr. Sugarman promotes unified leadership and direction for the Board and management. In addition, strong corporate governance structure and process ensures our independent directors will continue to effectively oversee management and key issues such as ~~both chairman~~strategy, risk and integrity. Board committees are comprised solely of independent directors. As such, independent directors oversee critical matters, including the integrity of our financial statements, the compensation of our CEO and management executives, financial commitments for capital projects, the selection and annual evaluation of directors, and the development and implementation of corporate governance programs.

Our Board and each Board committee have complete and open access to any member of management and the authority to retain independent legal, financial and other advisors as appropriate. The Non-Employee Directors, all of whom are independent, meet in executive session without management either before or after regularly scheduled Board and Board committee meetings to discuss various issues and matters including the effectiveness of management, as well as our performance and strategic plans.


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Role of the Lead Director

Every year, the independent members of the board ~~and chief executive officer.~~

~~Our board, by vote of its independent members, designates a Lead Director from among the independent directors, whose duties include the following:~~

~~Robin Josephs currently serves as our Lead Director.~~

The board believes that this leadership structure - a combined chairman and chief executive officer, a lead independent director, active and involved independent directors, and board committees led by independent directors - is the most appropriate and effective arrangement for us at this time. Due to the varied and complex nature of our business, the board believes the chief executive officer is in the best position to serve in the critical role of chairman of the board and lead us and the board effectively. Having a chairman who also serves as chief executive officer facilitates timely

communication with directors on critical business matters. The board believes that leadership of both the board and the company by Mr. Sugarman is the optimal structure to guide us and maintain the focus needed to achieve our business goals, while also providing for effective oversight by an independent board throughelect an independent lead director. Robin Josephs is currently designated as our lead independent director and is responsible for the following duties:

Presides at all meetings of the Board at which the Chairman
is not present and all executive sessions of the independent directors

Acts as advisor to CEO and direct liaison between CEO
and independent directors

Plans, reviews, and approves Board meeting agendas and information presented to the Board

Calls meetings of the independent directors as appropriate

Contributes to annual CEO performance review and assists with succession planning

Consults the Nominating and Governance Committee on
the Board's evaluation process

Participates in consultations and direct communication with major shareholders and their representatives when appropriate

Performs such other duties as the Board may determine from time to time

The ~~board also believes~~lead independent director is selected from among the ~~current board leadership structure functions very well and provides an effective balance between strong company leadership and appropriate oversight by independent~~non-employee directors. ~~The board recognizes that circumstances may change, however, and will periodically review its leadership structure.~~

~~All of our directors are elected annually.~~

The Nominating and Governance Committee ~~regularly assesses~~and management discuss candidates for the ~~size~~lead independent director position, and ~~composition~~consider many of the same types of criteria as candidates for the chair of other Board committees including:

O: Tenure
O: Previous service as a Board committee chair
O: Diverse experience
O: Participation in and contributions to activities of the Board
O: Ability and willingness to commit adequate time to the role

Board Composition and Diversity

We recognize the value of nominating individuals who will bring a variety of diverse opinions, perspectives, skills, experiences, backgrounds and orientations to the Board's discussions and decision-making processes. An overriding principle is that all nominations to the Board should be based on merit and suitability of the candidate. Subject to those considerations, the Board recognizes the need to consider director candidates from different backgrounds. The charter of the Nominating and Governance Committee identifies diversity as one factor the committee may consider when nominating a candidate for election to the Board. To that end, the committee strives for diversity not just in terms of innate factors like gender, race and age, but also in the categories of background, experience, skills, accomplishments, personal qualities and specific traits that would contribute to our ~~board to help ensure that our board functions in an effective manner given the size, diversity~~Board.

The Nominating and ~~complexity of our business and the range of business segments and markets in which we operate. The committee~~Governance Committee believes it is important to have a mix of experienced directors with a deep understanding of our business and others who bring fresh perspectives. The committee ~~engages in discussions of~~discusses potential additions to our board on an ongoing basis. In ~~seeking to maintain an engaged, independent board possessing broad experience~~addition, the Nominating and ~~judgment~~Governance Committee regularly assesses the size and ~~committed to representing the long‑term interests~~composition of our ~~shareholders,~~Board to help ensure that the Board functions effectively given the size, diversity and complexity of our business and the range of business segments and markets in which we operate. The committee ~~takes into account~~believes the ~~various factors described above in~~current size of the ~~section~~Board is appropriate considering the need for our directors to communicate and act efficiently, the time commitment required of ~~this proxy statement captioned “ELECTION OF DIRECTORS-Director Qualifications”. Mr. De Souza joined~~ our ~~board in July 2015 following~~directors and the nature of our strategic plans.

Director Independence

Our Corporate Governance Guidelines require that a ~~determination by~~majority of the ~~committee that his background, skills and experience would provide valuable perspectives to our board and enhance our corporate governance.~~

Board consist of directors who the Board has determined are independent. Our ~~board~~Board has determined that all of our current directors, other than our ~~chairman~~ Chairman


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and ~~chief executive officer,~~Chief Executive Officer, are independent. In determining director independence, the ~~board~~Board considers all relevant facts and circumstances, ~~and the NYSE~~as well as New York Stock Exchange (NYSE) listing standards. Under the NYSE listing standards, no director qualifies as independent unless the ~~board~~Board affirmatively determines that the director has no material relationship with ~~us,~~iStar, either directly or as a partner, stockholder, or officer of an organization that has a relationship with us. In addition, the Board has adopted the following standards to assist them in determining director independence

O: The director may not be an employee and no member of the director's immediate family may be an executive officer of iStar, currently or within the preceding 36 months. For purposes of these standards, "immediate family" includes a person's spouse, parents, children, siblings, mothers and fathers-in-law, sons and daughters-in-law, brothers and sisters-in-law, and anyone (other than domestic employees) who shares the person's home.
O: The director is not a current partner or employee of a firm that is iStar's internal or external auditor; no member of the director's immediate family is a current partner of such firm, or an employee of such a firm and personally works on the iStar audit; or neither the director nor any member of his or her immediate family was within the last three years a partner or employee of such a firm and personally worked on iStar's audit within that time.
O: The director does not serve as an executive officer of a charitable or non-profit organization to which iStar has made contributions that, in any of the last three fiscal years, exceed the greater of $1 million or 2% of the charitable or non-profit organization's consolidated gross revenues.
O: Neither the director nor a member of the director's immediate family is employed as an executive officer (and has not been employed for the preceding 36 months) by another company where any of iStar's present executive officers serves or served on that company's compensation committee.

Our Board has determined that each of the following non-employee director nominees qualifies as independent under NYSE rules and satisfies our independence standards: Clifford De Souza, Robin Josephs, Richard Lieb, Barry Ridings and Anita Sands.

The Nominating and Governance Committee ensures that there is a review of each director's employment status and other board commitments and, where applicable, each director's (and his or her immediate family members') affiliation with consultants, service providers or suppliers of the organization. With respect to each non-employee director, the Committee determined that either the director was not providing goods or services to us or the amounts involved were below the monetary thresholds set forth in the independence standards noted above.

No arrangement or understanding exists between any director and any other person or entity pursuant to which any director was, or is, to be selected as a director or nominee.

Nominations by Shareholders

The Nominating and Governance Committee is responsible for recruiting new directors. To contribute to that process, the committee may solicit and consider suggestions regarding possible nominees from current directors, management, or shareholders. In addition, we may retain professional search firms or consultants to help us identify potential directors with desired skills and disciplines.

Shareholder nominations for election to the Board should be sent to the attention of our Corporate Secretary at the address provided under "Communications with the Board." This correspondence should describe the candidate's qualifications and include the candidate's written statement of willingness and affirmative desire to serve as a director and to represent the interests of all shareholders. Shareholders also may nominate candidates directly by following the procedures specified in our bylaws for nominations and other shareholder proposals. See "When are shareholder proposals due for the 2020 annual meeting?" in this proxy statement.

Candidates proposed by shareholders will be considered in the same manner and using the same criteria as candidates identified by the Nominating and Governance Committee.


Corporate Governance · Nominations by Shareholders		iStar Inc. 2020 Proxy Statement\|17

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Board's Role in Risk Oversight

Due to the nature of our business, it is not possible or desirable to eliminate risk from our activities. Instead, we believe our focus should be on identifying, pricing, managing and monitoring risk, with the objective of achieving attractive, long-term, risk-adjusted returns. We have robust internal processes and a strong internal control environment designed to identify, manage, and mitigate material risks and to keep the Board and ~~Committee Annual Assessments~~its committees informed with respect to risk management matters.

The Board's role in risk oversight is consistent with our leadership structure generally.

The Board and its committees receive regular reports from members of senior management, outside auditors and internal audit firm on areas of material risk—including operational, IT, compliance, financial, legal, regulatory, strategic and reputational risk—in order to review and understand risk identification, risk management and risk mitigation strategies.

The Board and management are focused on risk management issues pertaining to our information systems and technology, including cybersecurity. Management is pursuing initiatives intended to identify and, if necessary, remediate weaknesses in our information security; enhance our internal cyber awareness training programs; and improve access to key information for the purpose of promoting operational efficiencies in data management. Management reports regularly to the Board on the status of these initiatives.

~~Our~~

Board and Committee Annual Assessments

To ensure the effectiveness of the Board as a whole and its committees, our directors engage in an annual assessment of the ~~board~~Board and committee ~~performance, for~~performance. For the purpose of ~~increasing~~ensuring the effectiveness of the ~~board~~Board as a whole and its ~~committees. An~~committees, an independent third- party interviews each director individually on a wide range of topics ~~relating to~~ including:

O: board structure and composition
O: communications between management, the Board, and its committees


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O: information furnished to the ~~board,~~ Board
O: the ~~board’s~~Board's relationship with management ~~and~~
O: the effectiveness of the ~~board~~Board and its ~~committees, and~~committees.

The independent third-party then summarizes the individual comments and assessments in an oral report to the ~~board~~Board in executive session. The ~~board~~Board utilizes the results of this process to help refine and improve the operations of the ~~board~~Board and its committees. In 2019, the annual assessment occurred in September and the report was presented to the Board and discussed at the October 2019 meeting.

~~Board Meetings Held during 2015~~

Board Meetings Held during 2019

During ~~the fiscal year ended December 31, 2015,~~2019, the board held 913 meetings, ~~including meetings held~~either in person ~~and~~or by telephone conference call. ~~All directors~~Directors are expected to attend a majority of the ~~board~~Board meetings. All directors attended at least ~~75% of all~~92% of the ~~board~~Board meetings and applicable committee ~~meetings. In addition, all~~meetings held during 2019. The Board also acts by unanimous written consent in appropriate circumstances. All of ~~the~~our directors ~~who were elected at the 2015 annual meeting~~ were present in person ~~or by conference telephone call~~at the 2019 annual meeting and were re-elected at that ~~annual meeting.~~meeting (other than Ms. Sands, who is a nominee for the first time in 2020).

Executive Sessions

Our ~~board~~Board of ~~directors meets~~Directors meet in executive session at least quarterly without management present. ~~Our audit committee~~The Audit Committee also meets in executive session at least quarterly, without management present, with representatives of our independent registered public accounting firm and with representatives with the accounting firm engaged to assist us in the preparation of our documentation, testing, and evaluation of internal controls over financial reporting.

Service on Other Boards

~~Committees Established by the Board~~

Our board has standing Audit, Compensation and Nominating and Governance Committees. These standing committees are comprised entirely of independent directors. Our board appoints special committees from time to time, as deemed necessary or appropriate.

~~Audit Committee~~

The Audit Committee is responsible for, among other things, retaining or dismissing our independent registered public accounting firm, reviewing with the auditors the plan and scope of the audit and audit fees, monitoring the adequacy of reporting and internal controls and meeting periodically with management and our independent registered public accounting firm.

As of the date of this proxy statement, the members of the Audit Committee are Dale Anne Reiss (chair), Clifford De Souza and Barry W. Ridings. The board has determined that each of the current members of the Audit Committee is independent, as defined by the Audit Committee’s charter and the NYSE listing standards, and that the chair of the committee qualifies as an “audit committee financial expert” as defined by the SEC. In addition, the board has determined that each of the current members of the Audit Committee is financially literate and has accounting or related financial management expertise, as such qualifications are defined under the rules of the NYSE. The Audit Committee met 8 times during 2015, including meetings held in person and by telephone conference call.

~~Compensation Committee~~

~~The Compensation Committee is responsible for overseeing our executive compensation programs. The principal responsibilities of the committee are:~~

To review management’s recommendations and advise management and the board on broad compensation programs and policies such as salary ranges, annual incentive bonuses and long‑term incentive plans, including equity‑based compensation programs, as well as other group benefit programs offered to employees generally.

To approve performance objectives that may be established for our senior executives and evaluate the performance of such executives relative to these objectives in connection with the committee’s overall review of executive compensation.

To approve, either as a committee or together with the other independent directors based on a recommendation of the committee, the base salary, annual incentive awards, long‑term incentive awards and other compensation for our chief executive officer.

To approve base salaries, annual incentive awards, long‑term incentive awards and other compensation for our other officers and employees with base salaries in excess of $200,000 per year (which include all officers who are subject to Section 16(b) of the Securities Exchange Act of 1934, as amended).

~~To administer the issuance of any award under our long‑term incentive plans and other equity compensation programs.~~

~~To retain and oversee third party consultants to assist with the committee’s activities, from time to time.~~

~~To oversee our performance evaluation practices and procedures.~~

~~To consider and evaluate “Say on Pay” resolutions and recommend to the board the frequency with which “Say on Pay” resolutions should be voted on by the shareholders.~~

~~To perform such other duties and responsibilities pertaining to compensation matters as may be assigned to the committee by the board.~~

~~To review the Compensation Discussion and Analysis and recommend to the full board that it be included in our proxy statement.~~

As of the date of this proxy statement, the members of the Compensation Committee are Robert W. Holman, Jr. (chairman), Robin Josephs, John G. McDonald and Barry W. Ridings. Each of the current members of the Compensation Committee is independent as defined by the Compensation Committee’s charter and the NYSE listing standards. The

~~Compensation Committee met 8 times during 2015, including meetings held in person and by telephone conference call.~~

~~Nominating and Governance Committee~~

The Nominating and Governance Committee is responsible for, among other things, considering and recommending actions relating to corporate governance matters. In addition, the committee considers and recommends to the board individuals to serve as our directors and executive officers. In making such recommendations, the committee considers such factors as it deems appropriate. These factors may include judgment, skill and experience with businesses and other organizations comparable to us. The charter of our Nominating and Governance Committee also identifies diversity as one factor which the committee may consider when nominating a candidate for election to the board. Diversity includes not only factors such as gender, race and age, but also background, experience, skills, accomplishments, personal qualities and other traits desirable in achieving an appropriate mix of qualified individuals.

The Nominating and Governance Committee may solicit and consider suggestions of the directors or management regarding possible nominees, may consider nominees suggested by shareholders and generally shall guide the process of recruiting new directors. The committee may employ professional search firms or consultants to assist us in identifying potential members of the board with the desired skills and disciplines. Nominations made by shareholders should be made in accordance with the procedures set forth below in this section under “Shareholder Nominations for the Board.” Candidates proposed by shareholders will be considered using the same criteria and in the same manner as all other candidates are considered.

As of the date of this proxy statement, the members of the Nominating and Governance Committee are Robin Josephs (chair), Robert W. Holman, Jr. and John G. McDonald. Each of the current members of the Nominating and Governance Committee is independent as defined by the applicable NYSE listing standards. The Nominating and Governance Committee met 5 times during 2015, including meetings held in person and by telephone conference call.

~~Committee Charters~~

~~Our Audit, Compensation and Nominating and Governance Committees have adopted charters that meet the standards established by the NYSE. Copies of these charters are available on our website at~~ ~~www.istar.com~~ ~~and will be provided in print, without charge, to any shareholder who requests copies.~~

~~Service on Other Boards~~

In view of the commitment of time and effort that is required of a director of a public company, our board has established a guideline that its non-employee directors should not serve on the boards of more than ~~six~~four public ~~companies. For this purpose, we treat service~~companies, including iStar, and that our chief executive officer should not serve on the boards of ~~mutual funds having~~more than two other public companies.

Director Resignation Policy

In an uncontested election, an incumbent nominee for director who fails to receive the ~~same investment adviser as service on~~requisite majority of votes cast for his or her election must offer to resign from the ~~board of one company.~~

~~No Special Arrangements for Service as Directors~~

No arrangement or understanding exists between any director or executive officer and any other person or persons pursuant to which any director or executive officer was, or is, to be selected as a director or nominee.

~~Board’s Role in Risk Oversight~~

Our management is charged with assessing and managing risks associated with our business on a day‑to‑day basis. The board’s role is to oversee management’s execution of these responsibilities and to assess our approach to risk management. In our view, it is not possible or desirable to eliminate risk from our activities. We believe that our focus should be on identifying, pricing, managing and monitoring risk with the objective of achieving attractive, long‑term, risk‑adjusted returns for the benefitBoard promptly following certification of the ~~company~~voting results. The Nominating and ~~our shareholders. We have robust internal processes~~Governance Committee will consider any such resignation offer, determine whether to recommend acceptance of that resignation, and ~~a strong internal control environment designed to identify, manage and mitigate material risks and to communicate with the board. The board exercises~~submit its oversight role periodically as part of its regular meetings and also through its committees, which examine various elements of risk as part of their responsibilities. The full board, or the appropriate board committee in the case of risks under the purview of a particular committee, receives regular reports from members of senior management on areas of material risk to us, including operational, financial, legal, regulatory, strategic and reputational risk, in order to review and understand risk identification, risk management and risk mitigation strategies. The board’s role in risk oversight is consistent with our leadership structure generally, with the chief executive officer and other members of senior management having responsibilityrecommendation for ~~assessing and managing our risk exposure, and the board and its committees providing oversight in connection with those efforts.~~

~~Shareholder Nominations for the Board~~

Shareholder nominations for election to the board should be sent to the attention of our corporate secretary at the address appearing on the notice accompanying this proxy statement, describing the candidate’s qualifications and accompaniedconsideration by the ~~candidate’s written statement~~Board. The director whose offer to resign is under consideration may not participate in any deliberation or vote of willingness and affirmative desire to serve in a manner representing the interest of all shareholders. Shareholders may also make nominations directly by following the procedure specified in our bylaws.

~~Candidates proposed by shareholders will be considered using the same criteria and in the same manner utilized by~~ the Nominating and Governance Committee ~~of the board in considering all candidates for election to the board, set forth above in this section under “Nominating and Governance Committee.”~~

~~Communications with the Board~~

We provide the opportunity for interested parties, including shareholders, to communicate with members of the board. Interested parties may communicate with our Lead Director, the other independent board members or the ~~chair of any of~~Board regarding the ~~committees of the board by e‑mail or regular mail. All communications by e‑mail should be sent to~~ ~~CorporateSecretary@istar.com. Communications sent by regular mail should be sent to the attention of the Lead Director, the independent directors, the Audit Committee chair, the Compensation Committee chair or the~~proposed resignation. The Nominating and Governance Committee ~~chair, as~~and the ~~case~~board may ~~be,~~consider any factors they deem relevant in ~~each instance in care of our corporate secretary at our headquarters at 1114 Avenue~~deciding whether to accept a director's resignation.

Within 90 days after the results of the ~~Americas, 39th Floor, New York, NY 10036.~~

~~Our chief legal officer~~shareholder vote are certified, the Board will disclose its decision in a press release, filing with the SEC, or by other public announcement. If an incumbent director's offer to resign is not accepted by the Board, such director will continue to serve until a successor is elected and ~~our secretary will review each communication received in accordance with this process to determine whether~~qualifies, or until the communication requires immediate action. These officers will forward all appropriate communications received, or a summary of such communications, to the appropriate board member(s). However, we reserve the right to disregard any communication that our chief legal officer and our secretary determine is unduly hostile, threatening, or illegal, does not reasonably relate to us or our business,director dies, resigns, retires, or is ~~similarly inappropriate. These officers have the authority~~removed, whichever shall occur first. If a director's offer to ~~disregard any inappropriate communications or to take other appropriate actions with respect to any such inappropriate communications.~~

~~EXECUTIVE OFFICERS~~

~~Information for Jay Sugarman, our chairman and chief executive officer,~~resign is contained above under the heading “ELECTION OF DIRECTORS.” Information is set forth below with regard to our other executive officers identified in this proxy statement. We have determined we have three executive officers. All of our officers serve at the pleasure ofaccepted by the board, ~~of directors and are customarily appointed as officers at~~then the ~~annual organizational meeting of the board held following each annual meeting of shareholders.~~

~~Nina Matis~~, age 68, serves as our executive vice president, chief legal officer and chief investment officer. She assumed her current position in February 2008 after serving as our general counsel since 1996, executive vice president since November 1999 and chief investment officer since April 2007. Ms. Matis is responsible for overseeing and managing the strategic consideration and execution of our investment and financing transactions, restructurings and resolutions of loans and other problem assets, significant operational responsibilities and litigation and other legal matters. She serves as a member of our Senior Management Investment Committee, which has authority to approve any of our investments in an amount greater than $25 million and up to and including $60 million. Ms. Matis previously served as a partner in the law firm of Katten Muchin Rosenman LLP, one of our principal outside law firms, and was an inactive special capital partner of the firm until her withdrawal from this position during 2010. From 1984 through 1987, Ms. Matis was an adjunct professor at Northwestern University School of Law where she taught real estate transactions. Ms. Matis previously served as a director of New Plan Excel Realty Trust, Inc. She is a director of Signature Theater Company, Thomas Cole House, a National Historic Landmark that includes the home and the studio of painter Thomas Cole, and National Partnership for Women & Families, a nonprofit, nonpartisan 501(c)(3) organization. Ms. Matis received a B.A. degree, with honors, from Smith College and a J.D. degree from New York University School of Law.

~~David DiStaso, age 51,~~serves as our chief financial officer, having assumed this position in December 2010. He previously served as our chief accounting officer since June 2008. Mr. DiStaso is responsible for managing our financial reporting, accounting, treasury, investor relations and other corporate finance functions, and is involved in the execution of all capital markets activities. He serves as a member of our Senior Management Investment Committee. Before joining us, Mr. DiStaso previously spent 11 years with the CIT Group, Inc., most recently as chief financial officer of

the Consumer Finance Division. He spent the first 10 years of his career in public accounting with KPMG, serving as a senior manager within the audit group and providing audit and consulting services to clients within the financial services industry. Mr. DiStaso received a bachelor’s degree from Rutgers College and is a Certified Public Accountant.

~~REPORT OF THE AUDIT COMMITTEE~~

~~The Audit Committee oversees the financial reporting process of iStar Inc. (Company), on behalf of the Board of Directors of the Company in accordance with our Audit Committee charter. The~~ board, in its ~~judgment, has determined that all members of our Audit Committee meet~~sole discretion, may fill the independence requirements of the Securities and Exchange Commission (SEC) and the New York Stock Exchange (NYSE). The board has also determined that at least one member of the Audit Committee, the chair of the Committee, is an “audit committee financial expert” within the meaning of the rules of the SEC and that each member of our Audit Committee is financially literate and has accounting or related financial management expertise, as such qualifications are defined under the rules of the NYSE. We operate under a written charter approved by the board, consistent with the corporate governance rules issued by the SEC and the NYSE. Our charter is available on the Company’s website at ~~www.istar.com~~ ~~and will be provided in print, without charge, to any shareholder who requests a copy.~~

The Company’s management is responsible for the financial reporting process and preparation of the quarterly and annual consolidated financial statements, including maintaining a system of internal controls over financial reporting, as well as disclosure controls and procedures. We are directly responsible for the appointment, compensation, retention, oversight and termination of the Company’s external auditors, PricewaterhouseCoopers LLP, an independent registered public accounting firm. The independent registered public accounting firm is responsible for auditing the effectiveness of the Company’s internal controls over financial reporting and for expressing its opinion thereon, in addition to auditing the annual consolidated financial statements and expressing an opinion on the conformity of those financial statements with generally accepted accounting principles in the United States. We also approve the engagement of an accounting firm to assist the Company in the preparation of its documentation, testing and evaluation of internal controls over financial reporting and reviewed their performance. We do not prepare financial statements or conduct audits.

~~In connection with the December 31, 2015 audited consolidated financial statements, we have:~~

reviewed and discussed with management and the independent registered public accounting firm the Company’s internal controls over financial reporting, including a review of management’s and the independent registered public accounting firm’s assessments of and reports on the effectiveness of internal controls over financial reporting and any significant deficiencies or material weaknesses;

reviewed and discussed with management and the independent registered public accounting firm the Company’s audited financial statements, including discussions regarding critical accounting policies, other financial accounting and reporting principles and practices appropriate for the Company, the quality of such principles and practices, and the reasonableness of significant judgments;

discussed with the independent registered public accounting firm the items that are required to be discussed by Statement on Auditing Standards No. 61, Communication with Audit Committees, as amended by Statement on Auditing Standards No. 90, Audit Committee Communications; and

reviewed and considered the written disclosures in the letter received from PricewaterhouseCoopers LLP, as required by the PCAOB regarding the independent accountant’s communications with the Audit Committee regarding independence, including a discussion about its independence from the Company and management.

Based on the reviews and discussions above, and subject to the limitations on the role and responsibilities of the Audit Committee referred to above and in the Audit Committee charter in effect in 2015, we recommended to the board that the audited consolidated financial statements for 2015 be included in the Company’s Annual Report on Form 10‑K for the year ended December 31, 2015, as amended on Form 10‑K/A on March 9, 2016 (the “2015 10‑K Report”), for filing with the SEC. The board approved our recommendation.

~~Submitted by the Audit Committee:~~

~~Dale Anne Reiss (Chair)~~

~~Clifford De Souza~~

~~Barry W. Ridings~~

The above report will not be deemed to be incorporated by reference into any filing by us under the Securities Act of 1933, as amended, or the Securities Exchange Act of 1934, as amended, except to the extent that we specifically incorporate the same by reference.

~~OTHER CORPORATE GOVERNANCE MATTERS~~

In addition to matters discussed elsewhere in this proxy statement, including above under “INFORMATION REGARDING THE BOARD OF DIRECTORS AND ITS COMMITTEES”, we have implemented the following practices and policies regarding corporate governance:

~~Opt-Out from MUTA Provisions~~

~~After undertaking significant discussions with our shareholders, described further below, our board has adopted a resolution approving an amendment to our charter (the “Articles Supplementary”)~~resulting vacancy pursuant to ~~which we are prohibited from electing to be subject to the provisions~~iStar's Bylaws.


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Table of ~~Sections 3-803, 3-804 and 3-805 of the Maryland General Corporation Law (MGCL).~~ Contents

Defensive Measures Profile

Opt-Out from MUTA Provisions

Subtitle 8, Title 3 of the ~~MGCL is~~ Maryland General Corporation Law—commonly referred to as the Maryland Unsolicited Takeover Act, or ~~MUTA, which would otherwise allow our board~~MUTA—permits companies to unilaterally classify ~~itself~~their boards into staggered classes and adopt certain other takeover defense measures. ~~The Articles Supplementary will become effective upon filing with~~Under an amendment to our charter approved by the ~~State Department of Assessments and Taxation of Maryland. The opt-out~~board in 2015, iStar is prohibited from electing to be subject to those provisions, meaning we cannot implement the takeover defense measures they describe. Our decision to opt out from the MUTA ~~provisions~~ may not be repealed ~~unless~~without the ~~repeal is approved by shareholders by the affirmative vote~~approval of ~~at least~~ a majority of our shareholders.

Shareholder Rights Plan

We do not have a shareholder rights plan, commonly known as a "poison pill," in effect.

"Whistleblower" Policy

Our Code of Conduct includes a policy on reporting suspected misconduct (a "whistleblower" policy) that describes how employees can report any concerns or suspected violations of our standards of conduct, policies, or laws and regulations to a named Compliance Officer, any other member of our Compliance Committee, our chief executive officer, or the ~~votes cast~~chair of the Audit Committee. This reporting may be done on ~~the matter~~an anonymous basis. We also have established an independent "hotline" telephone service that may be used by ~~shareholders which are entitled~~employees who wish to ~~vote generally~~report concerns or suspected violations, on an anonymous basis or otherwise. We prohibit retaliation against employees who report actual or suspected violations; anyone who attempts to retaliate will be subject to disciplinary action, up to and including termination. Reports of misconduct made in bad faith and false or misleading information provided in the ~~election~~course of ~~directors.~~an investigation will be subject to disciplinary action, up to and including termination.

~~Corporate Governance Guidelines~~

Governing Documents

The documents described below are available on our website atir.istar.com/corporate-governance/highlights. We will provide paper copies to our shareholders, without charge, on request.



Corporate Governance Guidelines	Code of Conduct	2020 Proxy

Audit Committee Charter	Compensation Committee Charter	Nominating and Governance Committee Charter

Disclosure Committee Charter

Corporate Governance Guidelines

Our ~~board~~Board has approved a set of general guidelines that provide the framework for our corporate governance. The ~~board~~Board reviews these guidelines and other aspects of our ~~corporate~~ governance ~~periodically,~~annually or as ~~necessary. Our corporate governance guidelines may be found on our website at~~ needed.


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~~www.istar.com~~ Table of Contents

~~and will be provided in print, without charge, to any shareholder who requests a copy.~~

Code of Conduct

Our Code of Conduct documents the principles of conduct and ethics to be followed by our directors, officers, and employees. The purpose of the Code of Conduct is to promote honest and ethical ~~conduct,~~conduct; compliance with applicable governmental rules and ~~regulations,~~regulations; full, fair, accurate, timely and understandable disclosure in periodic ~~reports,~~reports; prompt internal reporting of violations of the Code of ~~Conduct~~Conduct; and a culture of honesty and accountability. ~~A copy of the Code of Conduct has been provided to each~~All of our directors, officers and employees ~~who~~ are required to acknowledge that they have received and will comply with the Code of Conduct. Among its many features, the Code of Conduct describes how employees can report any matter that may be of concern to a named Compliance Officer, any other member of our Compliance Committee, our chief executive officer or the chair of the Audit Committee. This reporting may be done on an anonymous basis. We have also established an independent “hotline” telephone service that may be used by employees who wish to report any concerns or suspected violations of our standards of conduct, policies or laws and regulations, on an anonymous basis or otherwise. We will disclose any material changes to the Code of Conduct, and any waivers that are approved for directors or executive officers, in our public SEC filings and on our website within four business days of any such an event. ~~A copy of our Code of Conduct may be found on our website at~~ ~~www.istar.com~~ ~~and will be provided in print, without charge, to any shareholder who requests a copy.~~

Disclosure Committee

~~We maintain a~~

iStar's Disclosure Committee ~~consisting~~is made up of members of our executive management and senior staff. The purpose of the Disclosure Committee is to oversee our system of disclosure controls and to assist and advise the chief executive officer and chief financial officer in making the required certifications in SEC reports. The Disclosure Committee was established to bring together on a regular basis representatives from our core business lines and employees involved in the preparation of our financial ~~statements~~statements. These individuals meet quarterly, or otherwise as needed, to discuss any issues or matters ~~of which the members are aware that~~they believe should be considered for disclosure in our public SEC filings, and to review our draft periodic SEC reports ~~prior to filing.~~before they are filed. The Disclosure Committee reports to our ~~chief executive officer~~Chief Executive Officer and, as appropriate, to our Audit Committee. ~~The Disclosure Committee meets quarterly and otherwise as needed.~~

The Disclosure Committee has adopted a written charter to memorialize the ~~Committee’s~~committee's purpose and procedures. A copy of the charter will be provided, without charge, to any shareholder who requests one.

Succession Planning

Our Compensation Committee, pursuant to its charter, annually reviews and discusses with the independent directors of the Board the performance of our CEO and certain other senior officers and the succession plans for each management position, including recommendations and evaluations of potential successors to fill these positions. The Compensation Committee also reviews annually our management development and succession planning practices and strategies.

Our Chairman and CEO provides an annual review to the Board of Directors assessing the members of the executive leadership team. This review, which is developed in consultation with Compensation Committee, includes a discussion about development plans for the Company's executive officers and senior officers to help prepare them for future succession and contingency plans. The full board has the primary responsibility to develop succession plans for the Chairman and CEO position.


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Communications with the Board

Interested parties, including shareholders, are welcome to communicate with our lead director, the other independent board members or the Chair of any committee of the Board, by e-mail or regular mail. All communications should be sent to:



		By e-mail to: CorporateSecretary@istar.com				By regular mail, addressed to the particular director or directors desired, to: iStar Inc. c/o Corporate Secretary 1114 Avenue of the Americas 39th Floor New York, NY 10036

Our Chief Legal Officer and our Corporate Secretary will review each communication directed to the Board or individual directors. These officers will forward all appropriate communications received, or a summary of such communications, to the appropriate board member(s). Our Chief Legal Officer and Corporate Secretary have the authority to disregard any inappropriate communications or to take other appropriate actions with respect to inappropriate communications including abusive, repetitive, or in bad taste communications or communications that present safety or security concerns. Communications we receive that relate to accounting, internal accounting controls or auditing matters will be referred to the Audit Committee unless the communication is directed otherwise. You may ~~be found~~communicate anonymously and/or confidentially.


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Board Committees

Our Board has four standing committees—Audit, Compensation, Nominating and Governance and Investment—made up entirely of independent directors. The Audit, Compensation, and Nominating and Governance Committees have adopted charters that meet applicable standards prescribed by the NYSE. These charters are available on our website at~~www.istar.com~~ https://ir.istar.com/corporate-governance/board-of-directors, and will be provided in print, without charge, to any shareholder who requests ~~a copy.~~copies.

Our Board appoints special committees from time to time, as necessary.

~~Shareholder Outreach~~


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Audit Committee

Meetings in 2019:5

Clifford De Souza

Robin Josephs

Barry W. Ridings

Each member of the Audit Committee is independent, as defined by the Audit Committee's charter and the NYSE listing standards.



The Board has determined that each member also qualifies as an "audit committee financial expert" as defined by SEC rules.

Principal Responsibilities The Audit Committee is responsible, among other things, for the following matters: O appoints, compensates, retains, and oversees the work of our independent registered public accounting firm O ensures that procedures are established for handling complaints regarding accounting, internal accounting controls or auditing matters, including the confidential and anonymous submission of "whistleblower" reports by our employees regarding questionable accounting or auditing matters O meets periodically with management and our independent registered public accounting firm to review and discuss iStar's annual audited financial statements and quarterly financial statements O meets separately, on a periodic basis, with management, internal auditors, or our personnel responsible for the internal audit function, and with our independent registered public accounting firm O receives reports from management of (i) any significant deficiencies in the design or operation of our internal controls and (ii) any fraud involving management or other employees who have a significant role in our internal controls O reviews analyses of significant financial reporting issues and judgments made in connection with the preparation of iStar's financial statements				O reviews any accounting adjustments, any communications between the audit team and the audit firm's national office respecting auditing or accounting, and any "management" or "internal control" letter issued, or proposed to be issued, by the auditing firm O reviews our hedging policy and the status of hedging transactions on a quarterly basis O reviews our credit loss reserve policy and establishment of reserves on a quarterly basis O discusses policies with respect to risk assessment and risk management O discusses any material legal matters with senior management and the Board O ensures that policies are established regarding hiring employees or former employees of the independent auditors O reviews annually internal and external audits, if any, of our employee benefit plans and pension plans O reviews annually the adequacy of our insurance, management information systems, internal accounting and financial controls, protection of technology and proprietary information, and policies and procedures relating to compliance with legal and regulatory requirements The Report of the Audit Committee is on page 63 of this proxy statement.


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Compensation Committee

Meetings in 2019:5

Barry W. Ridings

Robin Josephs

Richard Lieb

Each member of the Compensation Committee is independent as defined by the Compensation Committee's charter and the NYSE listing standards.



No member of the Compensation Committee is or was formerly an officer or an employee of iStar. No executive officer serves as a member of the board of directors or compensation committee of any entity that has one or more executive officers serving as a member of our board, nor has such an interlocking relationship existed in the past.

Principal Responsibilities The Compensation Committee is responsible for overseeing our executive compensation programs. The principal responsibilities of the committee include: O approves performance objectives for our senior executives and evaluates the performance of such executives relative to these objectives O approves, either as a committee or together with the other independent directors based on a Compensation Committee recommendation, the base salary, annual incentive awards, long-term incentive awards, and other compensation for our Chief Executive Officer O approves base salaries, annual incentive awards, long-term incentive awards, and other compensation for our other senior officers and highly compensated employees O reviews management's recommendations and advises management and the Board on compensation programs and policies, such as salary ranges, annual incentive bonuses, long-term incentive plans, equity-based compensation programs, and other group benefit programs offered to employees generally				O administers the issuance of any award under our long-term incentive plans and other equity compensation programs O retains and oversees third party consultants as needed to assist with the Committee's activities O considers and evaluates "Say-on-Pay" voting results and recommends to the Board the frequency with which "Say-on-Pay" resolutions should be presented to the shareholders O performs such other duties and responsibilities pertaining to compensation matters as may be assigned by the Board O reviews the Compensation Discussion and Analysis and recommends to the full Board that it be included in our proxy statement The Compensation Committee Report is on page 53 of this proxy statement.


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Nominating and Governance Committee

Meetings in 2019:4

Robin Josephs

Clifford De Souza

Each member of the Nominating and Governance Committee is independent as defined by the applicable NYSE listing standards.

Principal Responsibilities

The Nominating and Governance Committee is responsible, among other things, for the following matters:

provides counsel to the Board of Directors with respect to the organization, function, and composition of the Board of Directors and its committees

oversees the annual self-evaluation of our Board of Directors and its committees, and the Board's annual evaluation of management, and report about those reviews to the Board

periodically reviews and, if appropriate, recommends to the full Board changes to our corporate governance policies and procedures

identifies and recommends to our full Board potential director candidates for nomination

recommends to the full Board the appointment of each of our executive officers

Investment Committee

Meetings in 2019:0

Richard Lieb

Clifford De Souza

Each member of the Investment Committee is independent as defined by the applicable NYSE listing standards.

Principal Responsibilities

The Investment Committee was formed in 2019 for the purpose of considering and, if appropriate, approving any transactions having a value in an amount up to and including $60 million in which both we and Safehold Inc. ("SAFE") are participants. No such transactions were considered by the Investment Committee during 2019. Such related party transactions in excess of $60 million are subject to approval by a majority of the Board's independent directors.


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Director Compensation

The compensation program for our non-employee directors provides for the following annual payments:

Role	Cash Retainer, Paid in Quarterly Installments ($)		Common Stock Equivalents (CSEs) or Restricted Shares of Common Stock, at the Director's Option⁽¹⁾ ($)


Non-Employee Directors	$	100,000	$	125,000

Committee Chairs:

O Audit		40,000		—

O Compensation		40,000		—

O Nominating and Governance		16,000		—

Committee Members:

O Audit		15,000		—

O Compensation		15,000		—

O Nominating and Governance		10,000		—

Lead Director				75,000

(1): The number of CSEs or restricted shares is based on the average NYSE closing price for our common stock for the twenty days prior to the date of the annual shareholders meeting.

Directors do not receive additional fees for attending board or committee meetings.

CSEs and ~~Communication; Shareholder Responsiveness~~

~~On a regular basis throughout~~restricted shares are granted effective on the date of the annual shareholders meeting and generally vest after one year, ~~our management engages~~on the date of the next annual shareholders meeting. Dividends will accrue in ~~communications with our significant investors~~respect of the CSEs and restricted shares from the date of grant as and when dividends are paid on the common stock, but such dividends will not be paid unless and until the associated CSEs or restricted shares vest. Dividends on CSEs are paid in the form of additional CSEs credited to ~~ensure that management~~the directors' accounts, based on the amount of the dividend and the ~~board understand~~value of a share of our common stock on the dividend payment date.

Under the Non-Employee Directors' Deferral Plan, directors may defer the receipt of some or all of their compensation.


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The table below summarizes the compensation information for our non-employee directors for the fiscal year ended December 31, 2019. Jay Sugarman is not included in this table as he is our employee and receives no additional compensation for his services as a director.

Name	Fees Earned or Paid in Cash ($)		Stock Awards⁽¹⁾ ($)		All Other Compensation⁽²⁾ ($)		Total ($)


Clifford De Souza	$	148,750	$	125,279	$	—	$	274,029

Robin Josephs		140,375		200,443		5,000		345,818

Richard Lieb⁽³⁾		81,875		125,279		—		207,154

Barry W. Ridings		147,500		125,279		5,000		277,779

Robert W. Holman, Jr.⁽³⁾		75,000		—		—		75,000

Dale Anne Reiss⁽³⁾		75,000		—		5,000		80,000

(1): Amounts included in the "Stock Awards" column reflect the grant date fair value of restricted share awards made to directors in 2019 computed in accordance with FASB ASC Topic 718 (without regard to forfeitures). These awards were made to the directors under the Non-Employee Directors' Deferral Plan. Directors may elect to receive these awards in the form of CSEs or restricted shares. No directors have presently elected to receive CSEs. The CSEs or restricted share awards are valued using the closing price of our common stock on the date of grant. Restricted shares are subject to a one-year vesting period from the grant date.
: As of December 31, 2019, the directors held the following aggregate amounts of previously-awarded CSEs and restricted shares:




CSEs	—	79,549	—	7,029

Restricted shares	14,334	22,934	14,334	14,334

(2): Our directors are eligible to participate in our broad-based matching gifts program under which we will donate funds equal to contributions made by directors or employees to qualified nonprofit organizations, up to a maximum annual matching contribution per individual of $5,000 for directors and senior officers, $2,500 for other officers, and $1,500 for other employees. Our directors also are eligible for reimbursement of the costs of attending continuing director education programs. Amounts included in the "All Other Compensation" column include any matching gifts made by us on behalf of the director and any education costs reimbursed by us to the director.
(3): Mr. Lieb was elected to our Board by our shareholders in May 2019. Mr. Holman's service as a director ended in May 2019 due to his unexpected death. Ms. Reiss retired from our Board in May 2019.


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Indemnification

Our charter provides that we will indemnify and advance expenses to our directors and officers to the full extent required or permitted by Maryland law. In addition, we have entered into indemnification agreements with each of our directors and executive officers. These agreements provide that we will indemnify our directors and executive officers to the fullest extent permitted by our charter and Maryland law against certain liabilities (including settlements) and expenses actually and reasonably incurred by them in connection with any threatened or pending legal action, proceeding, or investigation to which any of them is, or is threatened to be, made a party because of their status as our director, officer or agent, or because they serve as a director, officer or agent of another company at our request.

To supplement these indemnification provisions, we have obtained directors and officers liability insurance, which covers our directors and executive officers.


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Proposal 2—Advisory Resolution to Approve Executive Compensation

We are asking shareholders to approve, on an advisory basis, the Company's executive compensation as reported in this proxy statement. Although this advisory vote is non-binding upon the Company, the Board and the Compensation Committee will review and consider the ~~issues~~voting results when making future decisions regarding our executive compensation program.

We encourage shareholders to read the entire Compensation Discussion and Analysis section of this proxy statement, which describes how our executive compensation policies and procedures operate and are designed to achieve our compensation objectives, as well as the Summary Compensation Table and other related compensation tables and narrative, which provide detailed information on the compensation of our named executive officers.

The Compensation Committee and the Board of Directors believe that the policies and procedures articulated in the Compensation Discussion and Analysis are ~~important~~effective in achieving our goals and that the compensation of our named executive officers reported in this proxy statement has contributed to ~~our shareholders. We regularly discuss with our investors matters relating~~the Company's recent and sustainable long-term success.

RESOLVED, that the shareholders of iStar Inc. approve, on an advisory basis, the compensation of the Company's named executive officers disclosed in the Compensation Discussion and Analysis, the Summary Compensation Table and the related compensation tables, notes and narrative in the proxy statement for the Company's Annual Meeting of Shareholders.


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A Letter from the Chairman of the Compensation Committee

Dear Fellow Shareholders,

My transition to ~~our business, strategic plans, financial results, corporate governance issues, compensation program~~serve as the new Chairman of iStar's Compensation Committee came about under unfortunate and ~~related matters.~~

~~We significantly expanded these outreach efforts~~tragic circumstances following the ~~2015 annual meeting at which~~unexpected loss of our former Compensation Committee Chairman, Robert Holman, last May. Robert was a highly valued Board member and his presence is greatly missed. In transitioning to Committee Chairman, I knew I had big shoes to fill and also that our Committee had a great deal of work to do, given that a majority of our shareholders ~~expressed support~~had just voted against our Say-on-Pay proposal for the second year in a ~~proposal recommending~~row.

In our first Committee meeting after the Say-on-Pay vote, we determined that ~~we permanently opt out~~a new strategy was required to better demonstrate our commitment to a compensation program that is aligned with shareholders and that shareholder feedback and meaningful changes were core to the solution. We started our process by conducting a comprehensive review of ~~MUTA (as described above). In recent months, we~~iStar's existing compensation program.

The Committee then sought shareholder feedback to augment its preliminary analysis. We reached out to ~~our significant investors~~shareholders representing nearly 90% of outstanding shares and ~~engaged in~~held discussions with ~~holders of approximately~~investors holding 56% of ~~our~~ outstanding shares. ~~The specific purpose~~80% of these discussions ~~was~~included myself, our Lead Independent Director and fellow Compensation Committee member, Robin Josephs, and members of our investor relations and legal teams.

Shareholders told us that they were generally comfortable with the core structure of our long-term performance program and recognized the merit in linking executive compensation with Company returns on specific assets and overall market performance. However, they consistently expressed a desire for greater detail and transparency around our program and the process we use to ~~get~~determine payouts.

Shareholder feedback greatly influenced the Committee's decision-making process and led to the significant changes we have made to our program structure and design. In summary, and further detailed in the CD&A that follows, starting with the 2020 fiscal/performance year:

O: We have reduced our CEO's annual base salary from ~~significant investors, including investors who supported~~$1 million to $600,000
O: Our CEO will participate in the ~~MUTA proposal~~annual incentive plan ("AIP"), increasing the portion of his pay at risk and ~~those who did not,~~aligning him with the rest of the management team
O: We have revised AIP performance metrics to reflect key value drivers of the business by incorporating a second financial metric of adjusted book value per diluted share used to determine the overall size of the bonus pool.
O: We have added individual AIP performance goals to determine individual AIP targets
O: We have provided enhanced disclosure of individual AIP targets and caps for NEOs
O: We have introduced a cap on ~~their goals in supporting (or not supporting)~~individual bonus awards, with the ~~proposal, and what they are looking~~2020 AIP set at a maximum cap of 5 times base salary for the ~~board~~CEO and other NEOs
O: We have established a cap on the value of total annual compensation awarded to ~~do in response. Following these discussions,~~our CEO at $10 million
O: We have provided enhanced disclosure of individual iStar Performance Incentive Plan ("iPIP") scorecard to determine iPIP award allocations
O: We have toughened the ~~board carefully considered~~TSR modifier applicable to iPIP payouts for future iPIP pools, doubling the ~~issues relating~~penalty for poor relative TSR performance vs. the indices.


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These changes were made to ~~MUTA~~better align our compensation with shareholder interests, by further linking pay with performance and ~~determined~~increasing transparency and disclosure. While we believe that the changes outlined above are meaningful and reflective of our shareholders' suggestions, we are also humble enough to ~~adopt the Articles Supplementary~~know that, as time and ~~opt out of MUTA, as described above.~~

circumstances shift, so must our compensation approach. We ~~plan to continue these types of discussions~~will continually seek feedback with our shareholders ~~which provide valuable~~so their interests and iStar's executive compensation program are aligned.

I speak for the entire Committee in saying that we are deeply committed to getting executive compensation right and we encourage shareholders to reach out with any questions or ongoing feedback ~~and enable us~~related to ~~address shareholder concerns and interests~~our program; correspondence may be directed by e-mail toCorporateSecretary@istar.com or by regular mail addressed to the particular director or directors desired, in ~~designing and implementing~~care of our ~~programs and practices.~~Corporate Secretary, at 1114 Avenue of the Americas, 39th Floor, New York, NY 10036.

~~No Poison Pill~~

~~We do not currently have a shareholder rights plan, commonly known as a “poison pill,” in effect.~~


		Best,
		Barry Ridings Chair of Compensation Committee on behalf of the entire Compensation Committee

~~Compensation Related Matters~~


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Compensation Discussion and Analysis Contents


01Summary		34

Compensation Philosophy and Guiding Principles		34

Shareholder Engagement and Consideration of 2020 Say-on-Pay Vote		35

2019 Compensation Program Overview		37

Performance-Based Pay		37

Why We Created iPIP		38

How iPIP Works		38

Summary of 2013-2014 iPiP Plan Performance: Illustrative Example		39

2019 NEO Annual Compensation Determinations		39

Compensation Practices Align with Shareholder Interests		40


02Business Highlights and Performance		41

03Detailed Program Discussion		43

Base Salaries		43

Annual Incentive Plan		43

Long-Term Incentive Compensation—iPIP		45

Risk and Compensation		49

Compensation Governance		50

Roles and Responsibilities in Setting Named Executive Officer Compensation		51

Compensation Committee		51

Independent Compensation Consultant		52

Chief Executive Officer		52

~~See “~~


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~~Compensation Discussion and Analysis~~Table of Contents

- Key Compensation Practices” and “- Other Compensation Design Practices” for additional information on our policies on matters such as our stock ownership guidelines, hedging and pledging restrictions, compensation clawbacks and similar matters.

Compensation Discussion and Analysis

~~EXECUTIVE COMPENSATION~~

~~Compensation Discussion and Analysis~~

~~This compensation discussion and analysis describes the key principles and factors underlying~~

The CD&A details how our executive compensation ~~policies~~programs are designed and ~~decisions for 2015~~operate for our ~~executive officers identified~~Named Executive Officers ("NEOs"), who in ~~this proxy statement.~~ 2019 included:



Jay Sugarman		Chairman and Chief Executive Officer

Marcos Alvarado		President and Chief Investment Officer

Andrew C. Richardson		President of Land & Development and Chief Financial Officer (until May 2019)

Nina B. Matis		Vice Chair (until July 2019) and Chief Legal Officer (until March 2019)

The CD&A is organized into the following ~~discussion~~sections:

01: Summary
02: Business Performance Highlights
03: Detailed Program Discussion

01 Summary

The CD&A summary should be read in conjunction with the detailed compensation discussion and analysis (CD&A) that follows in addition to the other information presented in this proxy ~~statement, including the information in the~~statement.

Compensation Philosophy and Guiding Principles

Our compensation ~~tables~~programs are designed to foster a strong pay-for-performance culture by ensuring we balance emphasis on near-term and long-term performance. The Compensation Committee, and the ~~footnotes to those tables.~~

~~Introduction~~

~~Our compensation program reflects our pay‑for‑performance philosophy and is designed to create~~Board as a ~~strong connection between executive pay and our business performance, including shareholder value creation. The compensation program has the following objectives:~~

To further our current and long‑term strategic, business and financial goals in the creation of shareholder value by enabling us to attract, retain, motivate and reward key executives who contribute to achieving those goals.

To encourage our key executives to improve business performance and increase shareholder value by providing a mix of current compensation and long‑term rewards that is variable and distributed between salary and performance-based pay and includes cash, equity compensation and other benefits.

~~To align shareholder and employee interests by compensating employees for improving our business performance and increasing the value of the company, to the benefit of our shareholders.~~

~~To promote these objectives, a significant part of executive compensation is based on accomplishments that improve the performance of the company and increase the company’s value. We~~whole, believe this approach ~~helps us achieve our objectives and promote~~is essential given the ~~interests~~nature of our ~~shareholders. Our compensation actions during 2015 took into account the performance~~portfolio of assets and accomplishments of our management team towards achieving our current and long‑term strategic, business and financial goals, and reflect our continuing efforts to enhance the alignment between our executive incentives and results realized by our shareholders.

~~Company Performance~~

investment opportunities.

We have continued to originate investments within our core business segments of real estate finance and net lease, which we anticipate should drive future revenue growth. In addition, we have made significant investments within our operating property and land and development portfolios in order to better position assets for sale. Through strategic ventures, we have partnered with other providers of capital within our net lease segment and with developers with residential building expertise within our land and development segment. These partnerships have had a positive impact on our business, particularly in our land and development segment, which experienced an increase in revenue in 2015.

Access to the capital markets has allowed us to extend our debt maturity profile and become primarily an unsecured borrower. In 2015, we entered into the 2015 Revolving Credit Facility with a maximum capacity of $250.0 million. As of December 31, 2015, we had $711.1 million of cash, which we expect to use primarily to fund future investment activities, pay down debt, and for general corporate purposes.

During the year ended December 31, 2015, three of our four business segments, including real estate finance, net lease and operating properties, contributed positively to our earnings. We continue to work on repositioning or redeveloping our transitional operating properties and progressing on the entitlement and development of our land and development assets in order to maximize their value. We intend to continue these efforts, with the objective of having these assets contribute positively to earnings in the future.

For the year ended December 31, 2015, we recorded a net loss allocable to common shareholders of $52.7 million, compared to a net loss of $33.7 million during the prior year. Adjusted Income allocable to common shareholders for the year ended December 31, 2015 was $84.0 million, compared to $109.4 million during the prior year. (See Exhibit A attached to this proxy statement for our calculation of Adjusted Income.)

During the year ended December 31, 2015, we recognized $62.8 million less in equity method earnings than we did in the prior year, primarily associated with the sales of certain investments in 2014. This decrease was partially offset by an increase in total gross margin from our land and development portfolio, which improved to $49.5 million in 2015 from $17.3 million in 2014.

~~Compensation Program Design~~

Our compensation program seeks to enhance the linkage and measurement of employee performance and shareholder value creation through the design of our annual incentive and long‑term incentive compensation programs. Our Compensation Committee (Committee), with the assistance of Pay Governance LLC (Pay Governance), an independent compensation consultant engaged by the Committee, regularly reviews the design and implementation of the compensation programs to achieve this purpose.

In our regular communications with significant shareholders regarding our business, strategic plans, financial results and related matters, we have elicited our shareholders’ views regarding our compensation program and our efforts to enhance the alignment between our performance, our shareholders’ results and our executives’ incentives. The results of our recent Say on Pay vote indicates strong shareholder support of our compensation programs: at our 2015 annual meeting, our Say on Pay resolution received the support of 96.86% of our shareholders who voted. We continue to work to enhance our overall compensation programstrive to provide ~~appropriate incentive compensation~~our employees with meaningful reward opportunities ~~for our executives that are aligned~~while maintaining alignment with ~~our financial performance~~shareholder interests and ~~results for our shareholders.~~

~~Key Compensation Practices~~

~~Our key executive compensation practices are summarized below. We believe these practices promote good governance~~business imperatives. In setting and ~~serve the interests of our shareholders. Certain of these practices are described in more detail elsewhere in this proxy statement.~~

~~WHAT WE DO~~

~~We emphasize variable pay over fixed pay, with a substantial portion of~~overseeing the compensation of our executive officers, ~~identified~~the Compensation Committee believes our compensation philosophy is best enacted by designing programs and policies to achieve three core objectives:


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Shareholder Engagement and Consideration of 2020 Say-on-Pay Vote

Following two consecutive years of a disappointing say-on-pay vote, the Compensation Committee and full Board determined that a more robust and thoughtful approach to engagement and understanding shareholder feedback was required. The Compensation Committee conducted a thorough evaluation of iStar's compensation program with a focus on identifying the aspects of the program believed to cause concern for shareholders. The Compensation Committee then engaged in extensive dialogue with shareholders to understand their perspectives as well as to seek feedback on potential areas of change.

Since the 2019 Annual Meeting, iStar contacted shareholders representing nearly 90% of shares outstanding and held discussions with shareholders representing approximately 56% of shares outstanding. Discussions were held with all shareholders who accepted the invitation to engage, as well as with the two leading proxy advisory firms, ISS and Glass Lewis. In addition, we shared our presentation materials with those shareholders who did not respond or declined our invitation to give them the opportunity to review and comment on our program.

Compensation Committee Chair Barry Ridings and Lead Independent Director Robin Josephs participated in 80% of the discussions, several of which were held face to face, and the feedback from these engagements was then aggregated and shared with the full Board.

As a result of the feedback received in these discussions, the Compensation Committee has made meaningful changes to the executive compensation program. The Compensation Committee and full Board are committed to ensuring iStar's pay program aligns with shareholders' interests and supports long-term, sustainable value creation.


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Below is a list of the key themes from our discussions with shareholders and the direct actions we have taken in response. These actions reflect responsiveness across every aspect of feedback we received.


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2019 Compensation Program Overview

Our executive compensation program for 2019 consists of three primary components:

Performance-Based Pay

The Compensation Committee allocates pay among base salary, short term incentives, and long-term incentives to emphasize performance based, variable compensation. This mix ensures the appropriate alignment of executive compensation with financial performance and shareholder value creation. Notably, a substantial majority of the compensation opportunity for our CEO is delivered through iPIP, a long term, performance-based incentive compensation program.

The chart below illustrates our NEOs' mix of pay for 2019.

In light of the COVID-19 crisis, the Compensation Committee will be carefully evaluating performance metrics and goals in the components of our compensation program and reserves its discretion to alter them, depending on the length and severity of this crisis' disruption to the economy and our business.


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Why We Created iPIP

iPIP was implemented in 2013 and approved by our shareholders in 2014. iPIP has been designed to incentivize executives and other investment professionals to participate in the long-term financial success of iStar by directly linking their pay with the performance of our portfolio assets.

O: iStar's compensation program is intentionally unique because of our differentiated and unique asset mix and business platform
O: iPIP provides a compensation opportunity consistent with expectations of top-tier executives in other high-caliber, investment-based organizations with whom we compete for talent
O: Payout is not guaranteed, is subject to long vesting requirements, and is contingent upon strict performance criteria being met, incentivizing executives to drive the performance of portfolio assets over the long-term

How iPIP Works

One consistent piece of feedback iStar received during shareholder engagement efforts was the request for more transparent disclosure on the iPIP program and how it pays out. Below is a summary of the steps that guide payout decisions. Historically, there have been no payouts to management for five years or more from the date an iPIP pool has been established.

(1): The FTSE NAREIT REITs Index and the Russell 2000 Index.

The ultimate value of awards under iPIP is directly tied to the performance of iStar's portfolio assets and investments over the long-term and is subject to reduction based on our TSR. If iStar's TSR for the period commencing January 1, 2013, when the iPIP was adopted, and ending on the date an iPIP payout is determined is below the average of the median TSR of the select indices on that date, the amount paid out to iPIP participants from an iPIP pool will be reduced by the percentage difference of such underperformance. Effective starting in 2020, this negative TSR modifier for iPIP payouts has been toughened and that penalty for TSR performance vs. index is doubled


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Summary of 2013-2014 iPiP Plan Performance: Illustrative Example

As an example of how an iPiP pool operates:

Our initial iPiP pool was the 2013-2014 pool. Points in this ~~proxy statement being long-term performance-based~~

~~We provide a mix~~pool were initially awarded to 31 employees. In 2013 and 2014, iStar made $1.26 billion of investments, all of which were included in this 2013-2014 iPIP pool. During the first five years (2013 to 2017), there were no payouts to participants in this iPIP pool. As these investment assets were monetized, the first payouts to iPIP pool participants were made in 2018 and totaled $15.6 million. By the end of 2019, substantially all of the pool assets had been monetized and additional payouts were made totaling $7.4 million. Total payouts over this 7-year period to participants in this iPIP pool were $23.0 million, half of which was paid in cash and ~~equity compensation, with equity~~half in iStar common stock (at the then-current price at the time of distribution). Over the same 7- year period of this iPIP pool, iStar realized a round trip profit of $132 million on these iPIP pool investments, representing a net IRR of more than 18%. The Compensation Committee believes that this iPiP pool achieved its intended purpose as a long term incentive compensation ~~for our executive officers identified~~program: It was long term in nature covering 7 years and payouts were tied to strong investment performance. Since the investments in this ~~proxy statement consisting substantially~~Pool performed well, those iStar employees in the iPIP Pool received payouts. Conversely, had the investments in this iPIP Pool performed less well, lower payouts (or no payouts) would have been made.

2019 NEO Annual Compensation Determinations

The following table details the Compensation Committee's principal compensation determinations made during 2019 for iStar's NEOs. AIP awards determined and paid during 2019 represent payments for services in 2018 and are reported in the Summary Compensation Table on page 52 for the year in which the services were performed, in accordance with SEC disclosure rules. This table does not include miscellaneous items reported under "All Other Compensation" in the Summary Compensation Table.


			Annual Incentive (for 2018 service)		Long-Term Incentive

NEO	Salary ($)		Cash ($)	Equity ($)	Cash ($)	Equity ($)	Total ($)

Jay Sugarman Chairman and Chief Executive Officer	1,000,000		—	—	—	3,344,788	4,344,788

Marcos Alvarado President and Chief Investment Officer	500,000		1,900,000	—	—	2,190,493	4,590,493

Nina B. Matis Vice Chair (until July 2019) and Chief Legal Officer (until March 2019)	500,000 (annualized rate	)	1,175,000	—	—	—	1,675,000

Andrew C. Richardson President of Land & Development and Chief Financial Officer (until May 2019)	500,000 (annualized rate	)	650,000	—	—	518,099	1,668,099


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Table of ~~performance-based awards that also require continued service~~Contents

~~We include a variety of objective performance metrics in our incentive~~

Compensation Practices Align with Shareholder Interests

iStar's compensation program reflects best practices and stringent governance.


◦What we do
	~~Under our annual~~


		Provide the majority of compensation in the form of variable, performance-based elements.
		Ensure a strong link between financial and operational goals, shareholder value creation, and executive compensation.
		Maintain a fully independent Compensation Committee.
		Use an independent compensation consultant, engaged directly by the Compensation Committee, to advise on executive compensation matters.
		Enforce robust stock ownership guidelines for executives and non-employee directors.


		Provide for a clawback of incentive ~~bonus plan,~~compensation in the ~~size~~event of a material restatement of financial or operating results.
		Impose a double-trigger change-in-control requirement before any acceleration or payment of change-in-control compensation.
		Conduct shareholder engagement on compensation- and governance-related issues, engage in careful consideration of the annual ~~incentive bonus pool is determined based on our performance in achieving a predetermined financial performance benchmark compared~~Say-on-Pay results, and respond to ~~a target approved by the Committee~~shareholder feedback as appropriate.


◦What we don't do
	~~Under~~


		Executive officers and non-employee directors are prohibited from hedging shares of iStar stock, or from pledging shares of iStar stock except with prior approval in accordance with guidelines approved by our Performance Incentive Plan, or iPIP, which is the primary long-term incentive program for our executive officers identified in this proxy statement and key investment professionals, payouts to participants are based upon the performance of pools of new investments originated during a two-year period. No payouts to participants will occur until the company has realized a full return of our invested capital in the assets included in the pool plus a return based on both the company’s corporate leverage ratio and borrowing rateboard from time to ~~time (or asset specific leverage if applicable to~~time.
		No excise tax gross-ups.
		No repricing of underwater stock options or granting of stock options at a ~~particular investment) and a fixed preferred return rate; in addition, any earned payouts will be reduced if our total shareholder return, or TSR, underperforms~~price less than 100% of fair market value on the ~~TSR of two selected market indices~~grant date.


◦	~~For other employees, payouts~~	No preferential retirement plan or perquisites available to executives that are not generally available to all employees.
		No dividends are paid on equity incentive awards until they are vested.
		No accelerated vesting of ~~our performance-based~~incentive awards ~~under our Long‑Term Incentive Plan, or LTIP, are based on our TSR compared to~~in the ~~TSR of two selected market indices~~event employment terminates involuntarily.

~~We impose stock ownership guidelines~~


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02 Business Highlights and Performance

In 2017, we determined to implement a new vision: to re-establish ourselves as "the best" in a large and growing industry. With confidence that our modernized ground lease solution could benefit real estate investors and maximize value for ~~our senior executives and directors~~

~~We impose sale restrictions on vested annual incentive awards delivered~~iStar shareholders, we took necessary steps to pave the way for a new era of growth while bringing greater efficiency to a $7 trillion industry (as described below). It took several years, but in 2019 we began to realize the ~~form of shares~~

~~We prohibit hedging and significant pledging~~success of our ~~shares by our senior executives and directors~~

~~We include “double trigger” change~~development efforts. The result has been that 2019 was an excellent year for iStar. In brief, in ~~control provisions in incentive award agreements, which require termination~~2019 we successfully implemented a three-pronged strategy:

1.

Scale the ground lease business.

O: Closed $1.8 billion of ~~employment following a change in control for compensation to be paid~~

~~We impose “clawback” provisions in compensation awards, which enable us to recoup incentive compensation in~~transactions at Safehold, more than double the ~~event of misconduct directly related to a material restatement of our financial or operating results~~

~~We utilize an independent compensation consultant to advise the Committee on compensation program design, key compensation trends and internal and external competitiveness of our compensation program~~

~~WHAT WE DON’T DO~~

~~No employment agreements~~

~~No “change in control” agreements~~

~~No excise tax gross‑ups on any compensation paid on a change in control~~

~~No repricing of underwater stock options or granting of stock options at a price less than 100% of fair market value on grant date~~

~~No dividends or dividend equivalents paid on restricted stock units unless and until they vest~~

~~No preferential retirement plan, severance arrangements or perquisites available to executives that are not generally available to all employees~~

~~Primary Compensation Elements~~

~~Our executives are compensated through a combination of the following types of compensation:~~

~~Base salaries~~

~~Annual incentive awards (bonus)~~

~~Long‑term incentive awards, in the form of points in the iPIP and/or equity‑based awards under the LTIP~~

~~Group benefits available to employees generally, including 401(k) retirement plan and group health and welfare benefits~~

~~Tax Considerations~~

Section 162(m) of the Internal Revenue Code (Code) generally limits tax deductibility of compensation paid by a public company to its chief executive officer and certain other highly compensated executive officers (excluding the chief financial officer) to $1original $750 million ~~in the~~full year compensation becomes taxable to the executive, subject to an exception for performance-based compensation that meets specific requirements. The Committee considers the impact of this rule when developing and implementing its executive compensation programs; however, the Committee reserves the right to provide compensation that is not tax deductible if it believes the value in doing so outweighstarget

Increased the value of iStar's interest in Safehold (NYSE: SAFE), resulting in an unrealized gain of $511 million based on market value of SAFE at the ~~lost tax deduction.~~end of 2019

SAFE was the #1 performing REIT in 2019, with 118% total shareholder return

~~2015 Compensation Actions~~

2.

Highlight value in the portfolio and return capital to shareholders through stock buybacks and dividends.

O: Unlocked $400 million of gains through several asset transactions
O: Bought back 7.3 million shares, or 9% of total diluted shares outstanding
O: Raised the dividend by 11% to an annualized rate of $0.40 per share

~~Compensation decisions for our executives are made annually, after reviewing our performance as a~~

3.

Simplify the business by strengthening the balance sheet and ~~evaluating individuals’ performance and contributions~~accelerating the monetization of legacy assets.

O

Executed $2 billion of capital markets transactions during the year, ~~leadership qualities, business responsibilities, career~~resulting in several key credit enhancements:

i.: Reduced annual interest expense by $17.5 million from reduction of weighted average coupon by 53 basis points
ii.: Converted convertible Series J preferred stock into common stock, eliminating $9 million of annual preferred dividend expense
iii.: Increased unencumbered asset base to $3.5 billion
iv.: Extended debt maturity profile to nearly five years, including a 30-month runway with ~~us, current compensation arrangements, long‑term potential~~no corporate debt maturities
v.: Achieved credit rating upgrade from S&P

O

Eliminated distraction and minimized non-core businesses, allowing management to ~~enhance shareholder value and other relevant performance and market data. For 2015, Mr. Sugarman,~~focus on a singular mission:

i.: Sold $250 million of legacy assets for a $33 million gain
ii.: Reduced total legacy assets to just 16% of the portfolio

The Outcome: As a result of successfully executing our ~~chief executive officer, made specific compensation recommendations~~strategy, we were able to ~~the Committee~~deliver strong results for shareholders in 2019.


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Note: SAFE mark-to-market is based on the ~~objectives~~December 31, 2019 stock price of $40.30 with 31.2m shares owned by iStar and ~~approach set~~December 31, 2018 stock price of $18.81 with 7.6m shares owned by ~~the Committee,~~iStar.

(1): Presented diluted for Series J Convertible Preferreds.

On January 3, 2019, when we announced our significant additional $250 million equity investment in SAFE as well as current business conditions and other factors. Specifically, for each executive other than himself, Mr. Sugarman made recommendations regarding base salaries for the following year, annual incentive awards and long‑term incentive awards, for review and discussion with and approval by the Committee. As part of ~~its evaluation, the Committee considered various factors~~an expanded effort to accelerate SAFE's growth, our closing stock price was $9.09 and ~~data, including compensation levels~~SAFE's closing stock price was $17.89. At December 31, 2019, our closing stock price was $14.51 and ~~practices at other companies considered to be relevant for purposes~~SAFE's closing stock price was $40.30.


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Table of comparison, but did not engage in a formal benchmarking process. Mr. Sugarman attended meetings of the Committee at the request of the Committee chair, but did not attend executive sessions and did not participate in any Committee or Board discussions relating to the final determination of his own compensation.

~~In connection with its oversight of our 2015 compensation decisions, the Committee engaged Pay Governance as its independent compensation consultant to assist the Committee on a range of~~Contents

03 Detailed Program Discussion

Our executive compensation ~~matters. The Committee has considered~~program consists of three primary components:



I.		Base Salary

II.		Annual Incentive Plan (AIP)

III.		Long-Term Incentive Plan (iPIP)

For the independence of Pay Governance in light of SEC rules and NYSE listing standards. The Committee reviewed a report from Pay Governance addressing the consultant’s independence and concluded that the work of Pay Governance did not raise any concerns regarding independence, conflicts of interest or related matters.

Pay Governance provided information and advice regarding compensation levels for our executives and generally assisted the Committee in its consideration of (a) compensation for the chief executive officer, (b) recommendations made by the chief executive officer for the othernamed executive officers, ~~identified in this proxy statement and other employees, and (c) an appropriate overall structure and mix~~the Compensation Committee determines the amounts of ~~compensation.~~ these compensation components annually after considering:

Each executive's experience, knowledge, skills and personal contributions

iStar's performance relative to pre-established goals

Individual executives' accomplishments and performance

Real estate industry performance, general economic conditions and other "macro" factors

Each compensation component is discussed below.

Base Salaries

The consultant conferred with the Committee members, as a group and individually, to discuss our recent compensation history and other relevant matters. The consultant met with the Committee regularly, including in executive sessions as requested by the Committee, to discuss guiding compensation principles, competitive market trends and potential pay frameworks.

~~Base Salaries~~

~~The~~Compensation Committee reviews the base salaries of our named executive officers ~~identified in this proxy statement~~ every year. ~~In 2015,~~As shown below, there were no base salary increases in 2019, For 2020, the Compensation Committee has reduced CEO base ~~salaries of our chief executive officer~~salary in an effort to balance the CEO's annual pay across base salary and ~~our other executive officers identified in this proxy statement were not changed and remained as follows: Mr. Sugarman-$1,000,000; Ms. Matis-$500,000; and Mr. DiStaso-$400,000.~~

~~Annual Incentive Awards~~

~~Under our~~an annual incentive ~~program,~~award.


Named Executive Officer	2018 Base Salary ($)	2019 Base Salary ($)	Updated 2020 Base Salary ($)

Jay Sugarman	1,000,000	1,000,000	600,000

Marcos Alvarado	500,000	500,000	550,000

Nina Matis	500,000	500,000	N/A—retired July 2019

Andrew Richardson	500,000	500,000	N/A—left May 2019

Annual Incentive Plan

2019 AIP Structure

Our executives are eligible to earn an annual incentive award if we achieve financial performance goals approved by the Compensation Committee. For the 2019 AIP, the Committee approved Adjusted Income per Diluted Share as the financial metric to determine AIP funding. This performance metric has been used under our ~~total annual incentive~~AIP since 2016. Adjusted Income per Diluted Share measures the quality of the earnings we are generating. We believe our ability to generate high quality earnings directly impacts share price and shareholder value creation.¹ The Compensation Committee approved a range of performance requirements and associated AIP pool funding levels for 2019, as shown in the table below.² The AIP pool is funded based on ~~how we perform compared to a specific~~the level of performance ~~metric, as determined by~~achieved during 2019. All iStar employees participate in the Committee. To comply with Section 162(m) of the Code for 2015, the Committee established a separate performance metric and applicable performance target which is required to be achieved in order for bonuses paid for such fiscal year to the employees covered by Section 162(m) to be tax deductible. For 2015, the Section 162(m) performance target selected by the Committee was $234 million of Adjusted EBITDA, defined as net income (loss) AIP.~~plus~~ ~~interest expense, depreciation and amortization, stock-based compensation expense, provision for loans losses and impairments, and income tax expense, and~~ ~~less~~ ~~gains (losses) on early extinguishment of debt. (See Exhibit A attached to this proxy statement for our calculation of Adjusted EBITDA.)~~

The Committee selected Target Adjusted Income per share as the appropriate performance measure for determining the size of the annual incentive pool to be funded for payment of annual incentive bonuses to all employees.

Performance Metric	Below Threshold		Threshold		Target		Maximum		Actual


Target Adjusted Income per Diluted Share		<$0.77	$	0.77	$	0.92	$	1.07	$	4.91

AIP pool funding ($mil)	$	0.0	$	15.0	$	18.0	$	21.0	$	21.0

(1): Target Adjusted Income is calculated as Adjusted Income less actual economic losses realized on assets. ~~(See~~See Exhibit A ~~attached~~ to this proxy statement for our ~~calculation~~methodology and calculations of Target Adjusted Income.)
(2): A linear scale of performance targets and payout levels is utilized to determine performance and funding for results that fall between the specified amounts.

~~During 2015, the Committee reviewed the Target~~


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AIP pool funding is capped at threshold, regardless of Adjusted Income per ~~share forecast, established~~Diluted Share performance if our TSR is negative for the year. Due to our strong TSR performance during 2019, the cap did not apply.

The Committee approved these performance and payout levels after a multi-step process of reviewing the business plan and budgets, as well as headcount and roles. In approving the specific performance goals for Adjusted Income per Diluted Share for 2019 (threshold, target ~~ranges~~and maximum performance), the Committee considered a number of factors. As mentioned previously, the Company embarked on a new business strategy for ~~potential outcomes,~~2019, focused on growing its ground lease platform and ~~determined~~accelerating the disposition of legacy assets (and the income they produce). Management and the Committee discussed management's forecasts during two meetings at the beginning of 2019. Due to inherent risks regarding this significant strategic shift in our business plan, the process of establishing goals under the AIP was especially challenging. Prior results were not especially meaningful or relevant. Our projected ~~Threshold, Target~~financial performance in 2019 was highly variable and ~~Maximum annual incentive pool amounts~~based on a wide range of assumptions and uncertainties regarding likelihood of success, timing of transactions, market conditions, and other factors, including uncertainty regarding our ability to grow SAFE successfully, whether proceeds from the disposition of legacy assets would be ~~funded~~sufficient to offset anticipated realized losses, and whether the impact of lost income from asset dispositions could be minimized through operating costs reductions and/or other revenue sources. The Committee approved the threshold, target and maximum goals below the prior year's goals and actual performance based on the ~~Target Adjusted Income per share performance achieved~~strategic shift in our business plan, expectations for ~~2015,~~our investments in our portfolio, including Safehold, and macroeconomic factors. Given the ~~amounts~~transition that we began, the relative uncertainties of ~~$17 million (Threshold), $20 million (Target)~~launching a new strategy and ~~$24 million (Maximum).~~

~~In making these determinations relating~~the variable nature of the industry and financial markets from time to time, it is typical that our goals in a particular year may not directly relate to the annual incentive pool for 2015, the Committee conferred with Pay Governance regarding competitive market data and competitive target bonus award levels for individuals, reviewed our historical annual incentive awards levels and other factors, and consulted with the chief executive officer. actual or targeted performance of prior years.

To account for unanticipated circumstances and external economic factors, including the impact of shifts in timing of our asset transactions, the Compensation Committee has discretion to adjust the size of the total AIP bonus pool by up to 25% (up or ~~down by 25%~~down) based on its assessment of our overall ~~performance.~~

~~Following~~performance; factors relevant to how the ~~end~~performance results were achieved; our financial condition, including liquidity; and other relevant considerations. However, the Committee does not have discretion to override the impact of the ~~year,~~TSR modifier when it caps the ~~Committee determined that the~~AIP pool funding amount ~~of Target Adjusted Income per share achieved for 2015 was in the projected range for funding the annual incentive pool~~ at the ~~Target level~~threshold level. There were no discretionary adjustments to the AIP pool for 2019.

AIP Awards for 2019 (approved and paid in February 2020)

Mr. Sugarman was not granted an AIP award in 2019, consistent with the decision in recent years to emphasize long-term incentives as the primary form of ~~$20 million.~~CEO compensation. In light of shareholder feedback and the Committee's belief that a more traditional base salary and annual bonus structure is appropriate our CEO's base salary has been reduced in 2020 with the intent of making more of his annual compensation performance-based. The Compensation Committee ~~then took into consideration various factors~~considers and ~~reduced the amount of the total annual incentive pool to be funded for 2015 to $19 million.~~

~~Once the total funding of the annual incentive pool was determined by the Committee,~~approves individual ~~employees’ payouts~~awards from the AIP pool ~~were determined on a discretionary basis by the Committee~~for our other NEOs based on recommendations ~~from the chief executive officer~~by our CEO, following an assessment of each NEO's individual performance.

~~Under the annual incentive program, annual incentive~~

For services during 2019, 87% of our AIP pool was awarded to employees other than our NEOs. Individual 2019 AIP awards were made to our ~~more highly-paid executives,~~NEOs (not including Mr. Sugarman), based on the considerations described below.

Marcos Alvarado

Mr. Alvarado has served as our Chief Investment Officer since January 2018 and as our President since June 2018. Mr. Alvarado has been charged with overseeing originations and driving growth across iStar's diversified $5 billion investment portfolio, with special focus on the development of the ground lease sector. During 2019, as a key member of our senior executive ~~officers identified~~team, Mr. Alvarado has been a primary driver in ~~this proxy statement, are typically~~our successful execution of the three-part strategy we laid out in beginning of 2019, and was a significant contributor to:

O: Simplifying our business by strengthening the balance sheet and accelerating the monetization of legacy assets.
O: Highlighting value in our portfolio by unlocking gains through asset transactions and returning capital to shareholders through stock buybacks and dividends.


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O: Scaling Safehold, our ground lease business, including origination of $1.8 billion in new ground lease investments.

In recognition of his significant contributions and accomplishments during 2019, Mr. Alvarado was recently awarded an AIP bonus in the amount of $2.75 million, of which $2.20 million was paid in ~~a mix of~~ cash and ~~equity: for annual incentive awards for services performed in 2015, approximately 20% of the annual bonus amount~~$550,000 was paid in the form of fully-vested shares of ~~iStar common stock, which~~our Common Stock, that are ~~fully-vested but~~ subject to transfer restrictions ~~on selling the shares~~ for 18 ~~months, and/or allocations of points in the 2013-14 iPIP pool.~~

~~The Committee made its determinations in January 2016 regarding annual incentive awards for the executive officers identified in this proxy statement for services performed in 2015.~~

No annual incentive cash bonus was awarded to our chief executive officer, based on a determination to emphasize the long-term incentives in his total compensation in the form of Points in the 2015‑2016 iPIP pool described below.

Annual incentive awards for our other executive officers identified in this proxy statement were approved by the Committee based on the amount of the available annual incentive pool and the Committee’s assessment of each officer’s individual contributions to our financial and operating achievements during the year, as follows:


◦	~~Ms. Matis-$1,464,250, of which she received $1,056,250 in cash and $408,000 in the form of an allocation of 2.0 Points in the 2013‑2014 iPIP pool; and~~


◦	~~Mr. DiStaso-$500,000 in cash.~~

~~Pursuant to the SEC’s~~months. In accordance with SEC disclosure rules, ~~and regulations, in~~ the Summary Compensation Table below, the value of equity awards granted in 2016, even if granted in respect of 2015 performance, is not reported as part of the compensation for 2015 for our executive officers identified in this proxy statement but is reported as 2016 compensation. As a result, the equitycash portion of ~~the annual incentive awards described above are not~~this AIP award is reported in the Summary Compensation Table ~~of this proxy statement, but~~on page 52 as compensation for the year in which the services were performed (2019) and the shares portion will be reported in ~~next year’s proxy statement.~~2020, the year in which the shares were granted.

Andrew Richardson

Mr. Richardson served as our President, Land and Development, and Chief Financial Officer until May 2019. In light of our strategic decision in early January 2019 to focus on opportunities in ground lease investment and de-emphasize development activities, Mr. Richardson decided to step down from these positions to pursue other opportunities. Mr. Richardson was awarded an AIP bonus in February 2019 for his services during 2018 and did not receive any AIP bonus for services in 2019.

Nina Matis

Ms. Matis served as our Chief Legal Officer (until March 2019) and Vice Chairman (until July 2019) when she retired. Due to her announced intention to retire, Ms. Matis was not awarded an AIP bonus in February 2019 for services during 2018 and did not receive any AIP bonus for services in 2019.

~~Long‑Term Incentive Compensation: iStar Performance Incentive Plan (iPIP)~~

Long-Term Incentive Compensation—iPIP

Long-term incentive compensation for our NEOs in 2019 was delivered primarily through the iPIP. The ultimate value of awards, if any, under the iPIP is directly tied to the ~~primary vehicle~~ performance of our assets and investments, as well as our relative TSR performance.

iPIP Investment pools

Every other year we designate an investment pool consisting of assets and investments that iStar originates in the succeeding two-year period. The performance of each pool is measured on an ongoing basis during the life of the investments in the pool. Four iPIP investment pools have been designated since the iPIP was established—for ~~providing,~~investments originated in 2013-2014, 2015-2016, 2017-18, and 2019-2020.

Points in iPIP Pools

We grant participation interests, or points, in each iPIP pool, primarily to senior executives and select professionals engaged in our investment ~~activities, long‑term incentive compensation~~activities. In 2019, the Compensation Committee awarded points in the 2019-2020 iPIP pool.

Historically, a significant majority of the iPIP points in a specific pool were granted in annual installments over the applicable two-year period that the pool covered (e.g., points in the 2017-2018 IPIP pool were generally granted in 2017 and 2018). Beginning with the iPIP awards made in 2019 (for the 2019-2020 iPIP pool), awards will now be granted biennially. As such, our NEOs will not receive grants of iPIP points in the 2019-2020 pool in 2020.

Vesting of iPIP Points

iPIP points vest over a six-year period—40% after the initial two years, and 15% at the end of each of the next four years, provided the recipient is still employed at iStar. Vesting occurs even if the pool has ~~a direct relationship to~~not yet reached the ~~realized returns~~payout stage (described below). However, no payouts are made from an iPIP pool on ~~our new investments.~~ vested points unless and until the performance criteria for that pool have been met.

The values of iPIP points shown in ~~particular is designed to provide our management team with appropriate incentives and strengthen~~ the ~~alignment of their interests with those of our shareholders. The iPIP continues~~Summary Compensation Table are based upon the ~~evolution of our incentive compensation programs and enhances the performance‑based orientation of our overall program.~~

~~The iPIP creates compensation pools (which may be short‑term and/or long‑term pools depending~~fair value on the ~~nature~~date the points are granted, but for participants, the realizable value of iPIP points at the ~~investment assets included~~time they are granted is zero. The ultimate value participants may realize from their iPIP points, if any, depends on how well the investments in the iPIP ~~compensation pools) every~~pool perform over time, and that depends on a number of performance factors, including the amount investments originated, realization on those investments, asset-specific leverage, corporate leverage, credit losses, and other relevant factors.


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The below flow chart details the timeline from iPIP pool investment period to payout:

For purposes of illustration, the following table sets forth information on CEO awards and payouts in the 2013-2014 iPIP pool.


2013-14 iPIP—CEO-Specific Data ($000)(1)

Year		2013			2014			2015			2016			2017			2018			2019		Total			2020 & Beyond			Annual Average 2013-2019

Vesting Schedule		0	%		40	%		55	%		70	%		85	%		100	%		100	%	—			100	%

Grant Date Value		N/A		$	5,500		$	0		$	0		$	0		$	0		$	0		—		$	0

Realized Value	$	0		$	0		$	0		$	0		$	0		$	7,903	(3)		3,982	(3)	11,885	(3)		TBD		$	1,698	(3)

Total Cumulative Realized Value as % of Grant Date Value(2)		0	%		0	%		0	%		0	%		0	%		144	%		72	%	216	%		TBD

Each year, profits from the iPIP pool were directly invested back into iStar's business

However, CEO payout did not occur until 2018

Round-trip profit from the 2013-14 Pool (through 2019) was $132M

Net IRR for the 2013-14 Pool exceeded 18% per year

(1): Dollars in thousands
(2): Equals total realized value as a percentage of total grant date value
(3): Realized value paid 50% in our stock and 50% in cash.

iPIP Points Awarded in 2019

In February 2019, the Compensation Committee awarded points in the 2019-2020 iPIP pool to our NEOs as shown in the table below. The awards to the NEOs shown below, including Mr. Sugarman, were granted in recognition of their service and performance during 2018. As previously noted, the 2019 awards are intended to cover two years ~~that track~~of grants (2019 and 2020). The NEOs shown below, including Mr. Sugarman, will not be granted 2019-2020 iPIP points in 2020.

In granting this iPIP award to our CEO in 2019, the ~~investment~~Committee considered Mr. Sugarman's contributions on a range of quantitative financial metrics, such as our share price performance, balance sheet (liquidity and leverage levels), earnings measures and cash flow, and qualitative factors, such as strategic planning and positioning, succession planning and management development, investor relations, and employee engagement and culture. The Committee weighted these factors roughly 70% financial metrics and 30% qualitative factors.


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While this methodology has long been used by the Compensation Committee to determine point allocations for NEOs and ultimately payouts, going forward, in future proxy statements, a formal scorecard will be disclosed for future point allocations. The scorecard will outline the pre-determined goals for each NEO and their ultimate performance against those goals as determined by the Compensation Committee.

An illustrative scorecard is shown below, which describes the types of goals the Committee may consider for new iPIP point allocations to be made in 2021:

Financial Goals (70%)		Qualitative Goals (30%)


O Share price performance	—	O Strategic planning and positioning (i.e. growth targets for ground lease strategy)	—

O Liquidity	—	O Succession planning	—

O Leverage	—	O Personnel management / retention initiatives	—

O Cash Flow	—	O Corporate culture	—

O Adjusted Book Value / Share	—	O Investor relations	—

Executive


Jay Sugarman	40.00	$	3,344,788	40.00

Marcos Alvarado	25.00	$	2,090,493	25.00

Andrew Richardson⁽²⁾	5.00	$	418,099	5.00

(1): The executives realized no value and recognized no income at the time these awards were granted. As described above, actual payments will be made to the executives only if meaningful performance hurdles are achieved by iStar's investments and if long vesting periods are satisfied. In addition, iPIP payouts will be reduced if our TSR underperforms.
(2): Mr. Richardson forfeited these iPIP points, all of which were unvested, upon his voluntary departure from the Company in May 2019.

iPIP Distributions Paid in 2019

Under the iPIP, management makes the appropriate calculations of the performance of the ~~new~~ investments ~~made by us during those periods. iPIP compensation is awarded~~ in the ~~form~~iPIP pools. These calculations, together with supporting materials, are furnished to our independent registered public accounting firm as part of ~~Points,~~the overall audit process. An independent valuation consultant performs the necessary TSR calculations to determine the extent to which reductions in iPIP Pool fundings are ~~distributed at~~required based on TSR performance. Management's calculations, supporting materials, and the ~~outset~~TSR calculations are reviewed by the Compensation Committee before payout distributions are made to iPlP participants.

The initial payouts from the 2013-2014 iPIP pool were first made to participants during 2018, based upon a determination that the performance of anthe investments in the 2013-2014 iPIP ~~compensation~~pool had achieved sufficient net cash to provide for funding of this iPIP pool and ~~may also be held~~payout of distributions to participants, in ~~reserve for subsequent distribution at~~accordance with the ~~discretion~~terms of the ~~Committee. The total number~~iPIP.

During 2019, the investments in the 2013-2014 iPIP pool continued to generate cash sufficient to provide for additional funding of ~~Points~~the pool and payouts to participants. In addition, the performance of the investments in ~~any~~the 2015-2016 iPIP ~~compensation~~ pool ~~will be initially limited~~was determined to ~~100 (in addition, participants may be diluted ratably during~~have generated net cash sufficient to repay the ~~first two years of a pool in order~~interest expense on actual asset-specific debt and interest allocated to ~~admit additional participants, up to a total of 125 Points).~~

~~The iPIP is~~debt capital based on our corporate leverage rate, assure payment of the ~~fundamental principle that participants should only realize compensation benefits from a specified group~~preferred hurdle rate of ~~investments if those particular investments have achieved success for the company. Therefore, there are meaningful hurdles which must be achieved before iPIP participants receive any payout from~~9% on iStar's invested equity capital, repay actual asset-specific debt or


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assumed debt capital, and return iStar's invested equity, and therefore had generated cash available to fund the iPIP ~~compensation pools. Specifically, all payouts from each iPIP compensation~~ pool ~~are fully subordinated to a complete return of our invested capital in the assets included in that pool, together with a return partially~~and, after making necessary adjustments based on ~~a leverage component and partially~~our TSR performance, make payouts to participants based on ~~a preferred return hurdle rate (which is 9% for all of the~~their vested iPIP ~~pools allocated to date). In addition, there is another test designed to further align management and shareholder interests, which has the potential to reduce payouts~~points.

Before distributions are paid out from an iPIP ~~compensation~~ pool, ~~in the event that our long‑term~~a negative TSR modifier is first applied if iStar's relative TSR is below the average of the ~~median~~medians of ~~two market indices equally weighted between REITs (the~~the FTSE NAREIT ~~All~~ REITs ~~Index) and small cap stocks (the~~Index & the Russell 2000 ~~Index).~~

~~No payouts~~Index. Because iStar's TSR from January 1, 2013 to the respective dates payout distributions were determined was below the average of the medians of the two benchmark indices, distributions to participants in the 2013-2014 and 2015-2016 iPIP pools during 2019 were adjusted downward by (4.5)%, for distributions from the 2013-2014 iPIP ~~compensation~~pool calculated as of December 31, 2018, and (1.2)%, for distributions from the 2015-2016 iPIP pool calculated as of September 30, 2019. After such adjustments, distributions were paid out from the 2013-2014 and 2015-2016 iPIP pools ~~will occur until there is a full return of our invested capital~~to participants holding vested points, including distributions to the NEOs as shown below.


		Total distributions in respect of vested iPIP points during 2019⁽¹⁾		Average Annualized Rate of Total Distribution

Executive		Shares($)	Cash($)	($)

Jay Sugarman
	2013-2014 iPIP pool	1,991,139	1,991,139	568,897
	2015-2016 iPIP pool	2,435,261	2,435,261	974,104

Nina Matis
	2013-2014 iPIP pool	633,544	633,544	181,013
	2015-2016 iPIP pool	548,963	548,963	219,585

(1): These distributions were paid 50% in ~~the assets included in a particular pool~~cash and the required return on that capital and, therefore, the initial payouts of an iPIP compensation pool are not expected to occur until a substantial majority of the investment assets included in that particular pool are successfully liquidated. Further, iPIP participants are generally subject to a six‑year vesting period. To promote a further alignment of interests, 50% ~~of iPIP compensation will be payable~~ in shares of our common stock, ~~provided~~net of applicable tax withholdings.

Advantages of the iPIP Structure

iPIP's features foster strong alignment with shareholder interests.

First, the assets and investments in an iPIP pool must perform well before our executives receive any payout for their points. Even if the assets and investments do perform well, payouts will be reduced if iStar's TSR underperforms benchmark indices.

Second, the iPIP instills a long-term mindset. Points vest over the course of six years, and iPIP pools must perform successfully over the long term to satisfy the performance tests that are preconditions to any payout.

Third, to further align our executives' interests with those of our shareholders, iPIP payouts are divided equally between shares of our common stock and cash, rather than all-cash payouts. (However, if there ~~are~~happen to be insufficient shares available ~~shares~~ for issuance under ~~our~~the 2009 LTIP, ~~and~~iPIP payouts may be made in cash.)

Finally, the ~~balance will~~iPIP program is structured to be ~~paid in cash.~~

~~The iPIP is a critical component of accomplishing our long‑term goals~~similar to executive compensation programs offered by other investment platforms with whom we compete for talent (including real estate funds, hedge funds, and ~~is specifically designed to provide an incentive compensation opportunity that is modeled after~~ private equity “carried interest” programs. It is intended to provide a target aggregate compensation opportunity which, when taken together with a participant’s base salary and annual incentive compensation, will be consistent with the expectations of top‑tier investment talent in other high‑caliber, investment‑based organizations.

~~In 2015, the Committee approved long-term incentive compensation in the form of allocations of Points~~firms). We can only compete for the iPIP compensation pool that includes investments made in 2015-2016 (consisting of a long-term investment pool and a short-term investment pool). During 2015, 33.625 Points were initially allocated in the 2015-2016 iPIP Pool, out of a total of 100 Points initially authorized for the 2015-2016 iPIP Pool. The allocations made in 2015 as long-termbest executive talent if we offer market competitive incentive awards to our chief executive officer and our other executive officers identified in this proxy statement were approved by the Committee based on the Committee’s assessment of each officer’s individual contributions to our investment and origination activities in particular and our financial and operating achievements in general, as follows: Mr. Sugarman-20.0 Points (20% of the Points initially authorized in the 2015-2016 iPIP pool); Ms. Matis-3.5 Points (3.5% of the authorized Points); and Mr. DiStaso-1.0 Point (1% of the authorized Points).

~~Long‑Term~~opportunities.

Legacy 2009 Long-Term Incentive ~~Compensation: Equity‑Based Awards under Long‑Term Incentive~~ Plan ~~(LTIP)~~

As noted above, ~~while our~~the iPIP is intended to serve as the primary vehicle for providing ~~long‑term~~long-term incentive compensation to our named executive officers, other senior executives, and investment ~~professionals,~~professionals. However, as deemed appropriate, we will ~~continue to utilize equity‑based~~also grant equity-based awards under ~~our LTIP, which may be~~the 2009 LTIP. These awards typically are in the form of restricted stock units (Units) that ~~are performance‑based or time‑based.~~entitle the holder to receive an equivalent number of shares of our common stock if and when the Units vest.


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In ~~2015,~~February 2019, the ~~long-term incentive~~Compensation Committee granted LTIP awards ~~granted to Mr. DiStaso also included a long‑term incentive equity‑based award~~ in the form of Units ~~consisting of~~to our NEOs as shown in the table below. These Units vest in equal annual installments over a ~~target~~three-year vesting period and, on vesting, entitle the holder to receive an equivalent number of ~~8,052 performance‑based~~shares of our Common Stock, net of applicable tax withholdings. The LTIP awards to the NEOs shown below were granted in recognition of their service and performance during 2018.

Executive		Grant Date Value


Marcos Alvarado	11,429	$	100,000

Andrew Richardson⁽¹⁾	11,429	$	100,000

(1): This LTIP award of Units, all of which ~~may vest~~were unvested, were forfeited upon Mr. Richardson's voluntary departure from the Company in May 2019.

Risk and Compensation

We believe that both the company and our individual employees should focus on ~~December 31, 2017 if we~~identifying, pricing, managing, and monitoring risk, with the objective of achieving attractive, long-term, risk-adjusted returns for our shareholders. Our compensation program is designed to support and motivate our employees in achieving this objective without encouraging excessive risk-taking. We believe the following attributes contribute to an executive compensation program that does not create risks that are reasonably likely to have a material adverse effect on iStar.

Appropriate pay mix. We rely on an assortment of compensation elements—both fixed and variable, cash and equity-based, and short- and long-term—to ensure our executives focus on objectives that help us achieve ~~performance goals~~our business plans and create alignment with ~~respect to TSR over a three‑year performance period measured against two selected market indices, and 3,451 time‑based Units, which will cliff vest in one installment~~long-term shareholder interests.

Focus on ~~December 31, 2017 if he is employed by us on the vesting date. The terms~~long-term performance-based compensation. A significant portion of the ~~performance‑based Units~~compensation we pay our senior executives consists of long-term incentive awards that vest over multiple years. These awards will not pay out until iStar earns a complete return of our invested capital, as well as actual or imputed interest and ~~the time‑based Units~~a preferred return hurdle rate, and any payouts are ~~described below. During 2015,~~subject to reduction if our total shareholder return is below market.

iStar executives are also shareholders. Our NEOs, other executive officers, ~~identified~~and directors must comply with rigorous stock ownership guidelines.

Reduced incentive for misconduct. Our clawback policy allows us to recover incentive compensation paid to an executive in ~~this proxy statement were not granted long‑term~~the event such executive's fraud, willful misconduct, or violation of a company policy leads to a restatement of our financial statements or negative revision of a financial measure used to determine that incentive ~~equity‑based awards under our LTIP.~~

compensation.

No hedging or pledging. Our executives and directors are prohibited from engaging in transactions that hedge the risk of owning iStar common stock. In ~~2015, other~~addition, directors, officers, and other employees ~~were granted long‑term incentive equity‑based awards under~~may not pledge our ~~LTIP program~~securities as collateral for a loan or hold iStar securities in ~~the form of performance‑based Units and time‑based Units.~~

~~Performance‑Based Awards~~

~~LTIP awards delivered~~a margin account except with prior approval in ~~the form of performance‑based Units provide for vesting only if we achieve performance goals~~accordance with ~~respect~~guidelines approved by our board from time to ~~TSR over a three‑year performance period measured against two market indices, the FTSE NAREIT~~time.

No guaranteed employment. We have no employment agreements with executive officers. All ~~REITs Index (one‑half of the target award) and the Russell 2000 Index (one‑half of the target award). In addition, the employee must be employed by us on the vesting date.~~

~~Under these performance‑based LTIP awards, TSR is measured by the increase in the share price~~ of our ~~common stock during~~executives are employed on an "at will" basis and may be terminated with or without cause at any time. Similarly, our executives have no "golden parachute" or "golden coffin" arrangements. Taken as a whole, our compensation arrangements reward executives for appropriately identifying and managing risks, but provide no guaranteed "safety net" if they are ineffective in doing so. Moreover, the relevant performance period by comparing the price at the end of the current period to the price at the end of the prior period, and assuming reinvestment of dividends paid, if any, on common stock during the period. Our share price is calculated as the average of the NYSE closing pricesstructure of our ~~common stock on the last 20 trading days~~incentive compensation program ensures that any loss of ~~each relevant period. Our TSR~~value to our shareholders is ~~compared to that~~shared by management.


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Table of the constituents of the two market indices, which are calculated using a 20 trading day average price. Our stock price, and any companies that are not in the index at the beginning and end of the performance period, will be excluded from the TSR calculation for that index. Performance‑based Units will vest, and shares of our common stock will be earned in the amount of the vested performance‑based Units, based on the performance of our TSR compared to each index (measured as a percentile), as follows:

Contents

< Threshold Threshold Target High
TSR Percentile Achieved Less than 30th Percentile 30th Percentile 50th Percentile 75th Percentile
Shares Earned (as % of Target amount) 0% 50% 100% 200%

Compensation Governance

~~No shares will be earned if performance is below the threshold level,~~

In addition to structuring our compensation programs with objective, predetermined goals, and ~~results are interpolated on~~providing for direct oversight by our Compensation Committee, we employ a ~~linear basis between the levels of threshold, target and high, as shown above. If our TSR is negative, the~~ number of ~~shares earned is capped at the threshold level, regardless of our TSR performance relative~~features to the NAREIT All REITs Index and the Russell 2000 Index. Dividends will accrue but will not be paid unless and until performance‑based Units vest and are settled, that is, by the release and delivery of shares to the employee, net of statutory minimum required tax withholdings.

~~Time‑Based Awards~~

LTIP awards delivered in the form of time‑based Units provide for “cliff” vesting in one installment at the end of a three‑year vesting period if the employee remains employed on the vesting date. Dividends will accrue but will not be paid unless and until time‑based Units vest and are settled.

~~Other Compensation Program Design Features~~

~~We have also adopted the following policies as part of the overall design of~~enhance our compensation ~~program:~~

~~Minimum~~ governance, as described below.

Stock Ownership Guidelines ~~for Non‑Employee Directors and Senior Officers~~

Our ~~non‑employee~~non-employee directors, executive officers, and other senior officers are expected to maintain equity ownership interests having ~~a value~~ at least ~~equal to a specified~~ minimum prescribed values. Our ownership ~~level determined by reference to each such individual’s position,~~guidelines are as ~~set forth below:~~follows:



~~Position~~
5x		~~Minimum Ownership Level~~
~~Non-Employee Directors~~10x		~~5X annual~~6x		3x
Annual cash retainer ($500,000) Non-Employee Director
	Base salary ($6 million) Chairman and Chief Executive Officer (CEO)		~~5X base~~Base salary
~~Chief Legal Officer/~~ ($3.3 million) President and Chief Investment Officer		~~3X base~~Base salary
~~Other CEO Direct Reports (including~~ ($1.5 million) Chief Financial Officer and ~~Executive Vice Presidents)~~		~~1.5X base salary~~other CEO direct reports
~~Senior Vice Presidents (or equivalent)~~		~~1X base salary~~

~~For purposes of these stock ownership guidelines, unvested time‑based Units are counted~~

Non-employee directors and ~~unearned performance‑based Units are not counted. Each non‑employee director and officer has~~officers have five years from the ~~adoption of these guidelines in 2013, or the~~ date ~~of his or her election~~they are elected to the board or ~~appointment~~appointed to an officer position, as the case may be, ~~whichever is later,~~ to satisfy the ownership guidelines. ~~Taking into account any permitted transition period, all~~All of our ~~non‑employee~~non-employee directors and named executive officers ~~identified in this proxy statement~~ are currently in compliance with the guidelines.

Clawback Policy

We have a ~~“clawback”~~"clawback" policy that is reflected in the provisions of our incentive compensation awards. If we determine that an employee has engaged in fraud, willful misconduct, or violation of a company policy, and we further determine that ~~causes~~misconduct caused or ~~contributes~~contributed to a material restatement or adjustment of iStar's financial results within two years after the period presented, or ~~causes~~caused a material negative revision of a financial measure used to ~~award~~determine incentive compensation, the Compensation Committee will review ~~performance‑based~~performance-based compensation awarded to ~~the~~that employee and, if appropriate, seek recoupment of an appropriate portion of such ~~performance‑based compensation.~~

award.

Prohibition on Hedging Transactions

We have adopted a policy that prohibits directors, officers, and other employees from trading in financial instruments or engaging in ~~hedging~~ transactions involving our securities that are designed to hedge or offset the risks of price ~~fluctuations in the value~~fluctuations. Examples of ~~our securities (including but not limited to~~prohibited transactions are collars or forward sale contracts, puts, calls or other ~~exchange traded~~exchange-traded options, orand short sales of our ~~shares).~~

~~Prohibition~~shares.

Insider Trading Policies and Procedures

The federal securities laws prohibit a company's directors, officers, employees and other "insiders" from engaging in securities trading on ~~Pledged Securities~~the basis of material, non-public information. It is our policy, without exception, to comply with all applicable laws and ~~Margin Accounts~~

~~We prohibit directors,~~regulations in conducting our business. Accordingly, iStar has adopted an insider trading policy that prohibits each member of our Board of Directors and each of our officers and other employees from ~~pledging~~buying or selling our securities on the basis of material, non-public information, and from assisting or working in concert with others to do so. We impose "blackout periods" on a quarterly basis, and otherwise as ~~collateral for a loan or holding iStar~~appropriate, that prohibit insiders from trading in our securities, and require that any trading by an insider must be approved in ~~a margin account, except with prior approval in accordance with guidelines approved~~advance by our board from time to time. Exceptions may be granted and approval given on a case‑by‑case basis in circumstances where an individual clearly demonstrates the financial capacity to meet a margin call or repay the loan without resort to the pledged shares, or where the amountcompliance officer.


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Table of pledged shares or shares held in a margin account is not significant in comparison to the individual’s total ownership of our shares, or where the aggregate amount of pledged shares by all insiders is not significant compared to our total outstanding shares.

“Contents

"Double ~~Trigger” Change in Control~~Trigger" Change-in-Control Provision for ~~Long‑Term~~Long-Term Incentive Compensation

All ~~long‑term~~long-term incentive compensation awards for our executive officers ~~in the form of iPIP Points or LTIP Units,~~ include a ~~“double trigger” change in control~~"double trigger" change-in-control provision, meaning that a change in control of ~~the Company alone~~iStar will not alone cause any acceleration of vesting of ~~the incentive compensation awards~~those awards. Only if ~~the change in control~~a change-in-control transaction is followed by termination (or effective termination) of the ~~executive’s~~executive's employment, ~~or effective termination,~~ such as a material reduction in position, responsibilities, compensation, or other significant terms of employment, will the incentive compensation awards continue to vest, either in full or on a prorated basis.

~~Risk and Compensation~~

~~As noted above in the discussion~~

Tax Considerations

Section 162(m) of the ~~board’s role~~Internal Revenue Code generally limits tax deductibility of compensation paid by a public company to its chief executive officer and certain other highly compensated executive officers to $1 million annually. Prior to enactment of the Tax Cuts and Jobs Act in ~~risk oversight,~~November 2017, Section 162(m) included an exception for performance-based compensation that meets specific requirements. This exception has now been repealed, subject to certain grandfathered exceptions, which means employers generally lose the deduction for compensation to covered executives in excess of $1 million. Notwithstanding the loss of the exception for performance-based compensation, the Compensation Committee generally intends to continue to utilize the grandfathering rule under the Tax Cuts and Jobs Act where available. However, the Compensation Committee reserves the right to pay nondeductible compensation.

Roles and Responsibilities in Setting Named Executive Officer Compensation

Compensation Committee

The Committee is currently made up of three independent directors and reports to the Board.

The Compensation Committee reviews and approves overall compensation philosophy and strategy, as well as the compensation programs in which executive officers participate. Ultimately, the Compensation Committee is responsible for:

O: approving specific compensation for the executive officers
O: determining the form and amount of that compensation
O: aligning executive compensation with shareholders' interests

To that end, at the beginning of each year the Compensation Committee works with the CEO to set company performance goals and benchmarks for individual executive performance that we expect will positively influence shareholder value. At the end of each year, the Compensation Committee, taking into consideration the CEO's recommendations for his direct reports, determines and approves specific compensation amounts for our ~~view,~~executive officers.

With respect to the CEO, the Compensation Committee annually:

O: reviews and approves objectives
O: evaluates the CEO's performance against those objectives and iStar's overall performance
O: determines the CEO's compensation level based on that evaluation


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When appropriate, members of the Compensation Committee engage with shareholders and other stakeholders to seek input on executive compensation matters.

The Compensation Committee has authority to retain independent compensation consultants and legal counsel to assist it in fulfilling its obligations.

Independent Compensation Consultant

Pay Governance, an independent executive compensation consultant, has been retained by the Committee since 2012 to provide consulting advice on matters of governance and executive compensation.

As requested by the Compensation Committee, Pay Governance:

O: provides advice and opinion on the appropriateness and competitiveness of our executive compensation programs relative to market practice
O: provides advice on our compensation strategy and our internal compensation-setting processes and governance
O: attends Compensation Committee meetings

Chief Executive Officer

The CEO is ~~not possible or desirable~~supported by other members of the senior management team in setting goals and measuring company and individual performance.

The CEO works with iStar's other executive officers to ~~eliminate risk from our business activities. We believe that both~~set performance goals for the company and ~~our~~ individual ~~employees should focus on identifying, pricing, managing~~executives, as appropriate, at the beginning of each year. Using that collective insight, the CEO recommends incentive plan designs and ~~monitoring risk with~~goals for the ~~objective of achieving attractive, long‑term, risk‑adjusted returns~~Compensation Committee's review and approval.

The CEO makes recommendations to the Compensation Committee regarding compensation for ~~our shareholders. We believe that our compensation program should support~~the NEOs after reviewing iStar's overall performance and ~~motivate our employees in achieving this objective, but should not encourage excessive risk taking. We believe that our compensation program~~each executive's personal contributions. The CEO incorporates numerous qualitative factors into his recommendations.The CEO does not ~~create risks that are reasonably likely to have a material adverse effect on us, based~~participate in ~~part on the following attributes of our program:~~

~~We have no employment agreements with executive officers. All of our executives are employed on an “at will” basis and may be terminated with~~any discussions or ~~without cause at any time.~~

~~Compensation is variable and performance‑based. No individual’s compensation is guaranteed.~~

A significant portion of the compensation we pay our senior executives consists of long‑term equity incentive awards which vest over multiple years, and a substantial portion of the LTIP award opportunity will only vest if our shareholder value creation is above market, measured by comparison to two market indices.

~~Our executives have no “golden parachute” or “golden coffin” arrangements.~~

~~Our equity awards include clawback provisions which enable us to recover the awards in the event of gross negligence or misconduct directly~~deliberations related to ~~a material restatement~~his own compensation.


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Table of ~~our financial or operating results.~~

Contents

Compensation Committee Report

Taken as a whole, our compensation arrangements reward executives for appropriately identifying and managing risks, but provide no guaranteed “safety net” if they are ineffective in doing so. Moreover, the structure of our incentive compensation program ensures that any loss of value to our shareholders is shared by our management.

~~Compensation Committee Report~~

In connection with our oversight of the compensation programs of iStar Inc.~~, a Maryland corporation (the Company)~~, we, the members of the Compensation Committee listed below, have reviewed and discussed with management the Compensation Discussion and Analysis set forth in this proxy statement. Based upon ~~the~~this review and discussion, the Compensation Committee has recommended to ~~the~~iStar's board of directors ~~of the Company~~ that the Compensation Discussion and Analysis be included in this proxy statement and incorporated by reference in iStar's 2019 annual report on Form 10-K.


		Submitted by the Compensation Committee
		Barry W. Ridings (Chairman) Robin Josephs Richard Lieb


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Chief Executive Officer Pay Ratio

For 2019, the ~~Company’s 2015 Form 10‑K Report.~~

~~Submitted by~~ratio of the ~~Compensation Committee:~~

~~Robert W. Holman, Jr. (Chairman)~~

~~Robin Josephs~~

~~John G. McDonald~~

~~Barry W. Ridings~~

~~The above report will not be deemed to be incorporated by reference into any filing by us under the Securities Act~~annual total compensation of ~~1933, as amended, or the Securities Exchange Act of 1934, as amended, except~~Mr. Sugarman, our CEO, to the ~~extent~~median of the annual total compensation of all of our employees other than our CEO ("Median Annual Compensation") was 22 to 1. This ratio is a reasonable estimate calculated in a manner consistent with Item 402(u) of SEC Regulation S-K using the data summarized below. For purposes of this disclosure, we refer to the employee who received Median Annual Compensation as the "Median Employee." The date used to identify the Median Employee was December 31, 2019.

To identify the Median Employee, we first determined our employee population as of December 31, 2019. On that date, iStar and our consolidated subsidiaries collectively had 155 employees. This number includes both full-time and part-time employees, but not independent contractors or "leased" workers. We then measured compensation for the period beginning on January 1, 2019, and ending on December 31, 2019, for these employees. This compensation measurement was calculated by totaling, for each employee, gross taxable earnings, including salary and bonuses as shown in our payroll and human resources records for 2019. We annualized compensation for any employee who worked for less than the full year.

For purposes of calculating this ratio, we ~~specifically incorporate~~used the ~~same by reference.~~

total compensation of $4,367,387 reported for Mr. Sugarman in the Summary Compensation Table for 2019. Median Annual Compensation for 2019 was $196,004. This amount was calculated by totaling all applicable elements of compensation for our Median Employee for 2019 in accordance with Item 402(c)(2)(x) of Regulation S-K.


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Executive Compensation Tables

Summary Compensation Table

The following table and the accompanying footnotes ~~sets~~set forth compensation information for the past three years for ~~Jay Sugarman,~~ our ~~chief~~named executive ~~officer, David DiStaso, our chief financial officer, and Nina Matis, our chief legal officer and chief investment officer, in accordance with the SEC's disclosure rules and regulations.~~officers who served during 2018.


Name and Principal Position	Year	Salary ($)		Bonus ($)		Stock Awards ($)			Non-Equity Incentive Plan Compensation($)			All Other Compensation ($)⁽¹⁾		Total ($)		Year	Salary ($)	Bonus ($)		Stock Awards ($)⁽¹⁾		Non-Equity Incentive Plan Compensation ($)⁽²⁾			All Other Compensation ($)⁽³⁾				Total ($)

Jay Sugarman	2015	$	1,000,000	$	—	$	5,360,000	⁽²⁾	$	—	⁽³⁾	$	11,345	$	6,371,345	2019	1,000,000		—	3,344,788			—	⁽⁴⁾		$	22,599		$	4,367,387

Chairman and	2014	1,000,000		—		5,500,000		⁽²⁾	—		⁽³⁾	11,095		6,511,095		2018	1,000,000		—	5,000,000			—	⁽⁴⁾		11,793			6,011,793

Chief Executive Officer	2013	1,000,000		—		1,423,637		⁽⁴⁾	—		⁽³⁾	11,162		2,434,799		2017	1,000,000		—	3,640,000			1,000,000			12,142			5,652,142
David DiStaso	2015	400,000		—		795,656		^(2)(5)(6)	500,000		⁽⁷⁾	11,345		1,707,001
Chief Financial Officer	2014	400,000		—		467,147		⁽²⁾⁽⁶⁾	747,500		⁽⁷⁾	10,759		1,625,406
	2013	400,000		849,997		551,591		⁽⁴⁾⁽⁸⁾	—			14,838		1,816,426

Marcos Alvarado																2019	500,000			2,190,493	⁽⁵⁾		2,200,000			11,463			4,901,955

President and																2018	490,530		—	3,125,000	⁽⁶⁾		1,900,000			10,470			5,526,000

Chief Investment Officer																2017	—		—	—			—			—			—

Nina Matis	2015	500,000		—		2,001,503		⁽²⁾⁽⁵⁾	1,056,250		⁽⁷⁾	15,712		3,573,465		2019	250,000		—	—			—			1,045,395		⁽⁷⁾	1,295,395
Chief Legal Officer and	2014	500,000		—		1,062,500		⁽²⁾	2,112,500		⁽⁷⁾	15,462		3,690,462
Chief Investment Officer	2013	500,000		2,499,997		1,142,972		⁽⁴⁾	—			15,530		4,158,499

Vice Chairman (until																2018	500,000		—	690,000	⁽⁸⁾		1,175,000			10,595			2,375,595

July 2019) and Chief Legal Officer (until March 2019)																2017	500,000		—	1,152,080			1,950,000			18,989			3,621,069

Andrew Richardson																2019	185,606		—	518,099	⁽⁵⁾		—			189,961		⁽⁹⁾	893,666

President, Land and																2018	376,894		—	1,517,000	⁽¹⁰⁾		650,000			9,655			2,553,549

Development, and Chief Financial Officer (until May 2019)																2017	—		—	—			—			—			—


~~(1)~~	Amounts reported in the "All Other Compensation" column include our matching contributions to the accounts of the executive officers identified in this proxy statement in our 401(k) Plan and additional compensation attributable to certain life and disability insurance premiums.

~~(2)~~

Amounts reported in the "Stock Awards" column for 2015 include the dollar value of iPIP Points granted in January 2015 to the executive officers identified in this proxy statement in the 2013-2014 iPIP compensation pool and/or the 2015-2016 iPIP compensation pool. Amounts reported in the "Stock Awards" column for 2014 include the dollar value of iPIP Points granted to the executive officers identified in this proxy statement in May 2014 in the 2013-2014 iPIP compensation pool.

(1): Amounts reported in the "Stock Awards" column include our performance-based iPIP awards, which vest over six years. Amounts reported in this column include the dollar value of iPIP points granted in the year listed. The executives realized no value and did not receive income at the time these awards were granted. Actual payments will be made to the executives in respect of these awards only if meaningful performance hurdles are achieved by iStar's investments and long vesting periods are satisfied. In addition, iPIP payouts will be reduced if our TSR underperforms. See "Compensation Discussion and Analysis—iPIP distributions paid in 2019," for a discussion of payouts made to our NEOs in 2019.
: The values of the iPIP awards are based on the grant date fair value calculated in accordance with FASB ASC Topic 718 (without regard to forfeitures) based on various assumptions with respect to forecasted investment originations, expected realization dates of investments (including maturities or sale dates), asset-specific leverage, corporate leverage, investment returns, credit losses, and other relevant factors. These assumptions are subject to risks and uncertainties that may cause actual results or outcomes to differ ~~materially~~materially. Refer to Note 15 of our consolidated financial statements in our 201910-K Report for further details.
: Amounts reported in the "Stock Awards" column for 2019 include the dollar value of iPIP points granted in 2019 to our named executive officers in the 2019-2020 iPIP pool. Amounts reported in the "Stock Awards" column for 2018 include the dollar value of iPIP points granted in 2018 to our named executive officers in the 2017-2018 iPIP pool. Amounts reported in the "Stock Awards" column for 2017 include the dollar value of iPIP points granted in 2017 to our named executive officers in the 2013-2014 iPIP pool, the 2015-2016 iPIP pool, and/or the 2017-2018 iPIP pool.
(2): Amounts reported in the "Non-Equity Incentive Plan Compensation" column include cash awards paid under our AIP to our named executive officers. Pursuant to the SEC's disclosure rules and regulations, cash bonuses paid under the AIP are reported under the "Non-Equity Incentive Plan Compensation" column for the year in which services were performed.
(3): Amounts reported in the "All Other Compensation" column include our matching contributions to the accounts of our named executive officers in our 401(k) Plan, additional compensation attributable to certain life and disability insurance premiums, and accrued dividend equivalents paid upon the vesting of our long-term incentive awards.


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(4): No annual incentive awards were paid to Mr. Sugarman under our AIP for services in 2019 and 2018.
(5): Amounts reported in the "Stock Awards" column for 2019 for Mr. Alvarado and Mr. Richardson include the dollar value of LTIP awards granted in 2019, in the amount of $100,000 each. The executives realized no value and did not receive income at the time these awards were granted. These awards vest over a three year period beginning on January 2020. The fair values of these time-based Units were calculated based upon the share price at the date of grant. Mr. Richardson forfeited his LTIP award upon his departure from ~~these assumptions. The fully-vested~~the Company in May 2019.
(6): Amounts reported in the "Stock Awards" column for 2018 for Mr. Alvarado include the dollar value of iPIP points in the 2017-2018 iPIP pool granted to Mr. Alvarado on commencement of his employment on January 8, 2018, based on the grant date fair value of such awards calculated in accordance with FASB ASC Topic 718.
(7): Amounts reported in the "All Other Compensation" column for 2019 for Ms. Matis include amounts paid in connection with her retirement as our Chief Legal Officer (in March 2019) and our Vice Chairman (in July 2019), including special bonus payments in July 2019 and January 2020, consulting services through December 31, 2019, and amounts paid with respect to premiums for health insurance continuation coverage for 6 months, in addition to matching contributions under our 401(k) Plan and additional compensation attributable to certain life and disability insurance premiums.
(8): Amounts reported in the "Stock Awards" column for 2018 for Ms. Matis include shares of our common stock issued in 2018 as part of her annual incentive award for services rendered in 2017. These shares were fully vested but subject to sales restrictions for specified periods.
(9): Amounts reported in the "All Other Compensation" column for 2019 for Mr. Richardson include amount paid to him upon his departure from the Company in May 2019, representing the estimated value of the vested portion of iPIP points previously granted to Mr. Richardson, which were surrendered and cancelled.
(10): Amounts reported in the "Stock Awards" column for 2018 for Mr. Richardson include the dollar value of LTIP awards and iPIP points in the 2017-2018 iPIP pool granted to Mr. Richardson on commencement of his employment on March 30, 2018, based on the grant date fair ~~values were~~value of such awards calculated in accordance with FASB ASC Topic 718. The fair value of the time-based Units was calculated based upon the share price at the date of grant. Refer to Note 14 of our consolidated financial statements in our ~~2015~~2018 10-K Report for further details.


~~(3)~~ 56\|iStar Inc. 2020 Proxy Statement	No annual incentive awards were paid to Mr. Sugarman for services in 2015, 2014 and 2013 in consideration of iPIP Points awarded to him in 2016, 2015 and 2014, respectively. The iPIP Points awarded in 2016 will be reported in next year's proxy statement. The iPIP Points awarded in 2015 and 2014 are reported under the “Stock Awards” column of this Summary Compensation Table in the respective year they were granted.

~~(7)~~

~~See "Compensation Discussion and Analysis~~-Performance-Based Awards" for a discussion of these performance-based Units that will vest on December 31, 2017 at 0%-200% of "target" award amount based on our TSR measured over the performance period relative to the FTSE NAREIT All REITs Index (one-half of the target award) and the Russell 2000 Index (one-half of the target award). The number of Units reported is the maximum amount of the award. The payout value is reported based on achieving the maximum amount of the award and multiplying the number of Units by $11.73, the closing market price of our common stock on December 31, 2015. Assuming the performance period ended on December 31, 2015, this award would have achieved a payout equal to 50% of target payout of the award, resultingStock Vested in ~~a payout value of $47,254.~~Fiscal 2019

~~STOCK VESTED IN FISCAL 2015~~

The following table presents information for ~~the~~our named executive officers ~~identified in this proxy statement~~ relating to stock awards that vested during ~~2015.~~2019.

Stock Awards
Name
Number of Shares Acquired on Vesting (#)⁽¹⁾
Value Realized on Vesting ($)
Jay Sugarman —
$ —

David DiStaso 22,195
284,823

Nina Matis 56,557
737,503


	Stock Awards

Name	Number of Shares Acquired on Vesting (#)	Value Realized on Vesting ($)

Andrew Richardson⁽¹⁾	20,000	168,400

(1): Mr. Richardson received 12,357 net shares of our common stock upon vesting of this award of Units, after deduction of shares for applicable tax withholdings.


~~(1)~~	There were no stock awards that vested during 2015 for Mr. Sugarman. The net amounts of shares received by Mr. DiStaso and Ms. Matis upon vesting of these awards, after deduction of shares withheld by us to cover associated tax liabilities, as applicable, were 13,651 and 24,987 shares, respectively. No Pension or Deferred Compensation

~~Pension Benefits; Deferred Compensation~~

We do not maintain any ~~tax‑qualified~~tax-qualified defined benefit plans, supplemental executive retirement plans, or similar plans for which information is required to be reported in a pension benefits table. Similarly, we do not maintain any ~~non‑qualified~~non-qualified deferred compensation plans for which information is required to be reported.

Employment Agreements with Executive Officers

We do not have employment agreements with any of our named executive officers.

Change-in-Control or Similar Arrangements

None of our named executive officers ~~identified in this proxy statement.~~

~~Severance, Change‑in‑Control or Similar Arrangements~~

~~We do not maintain~~are party to any severance, change‑in‑control or similar programs or arrangements that provide for payments to the executive officers identified in this proxy statement following termination of employment or a change in control of the company, except as described herein. In addition, none of our executive officers identified in this proxy statement have any “single trigger” change in control"single trigger" change-in-control arrangements that provide for compensation ~~including~~(including accelerated vesting of stock ~~awards,~~awards) in the event of a change in control. All ~~long‑term~~long-term incentive compensation awards, including iPIP, equity incentive awards and other arrangements for our named executive officers, ~~identified in this proxy statement~~ include a ~~“double trigger” change in control~~"double trigger" change-in-control provision, meaning that a change in control of ~~the Company alone~~iStar will not alone cause any acceleration of vesting of the incentive compensation awards. ~~Only if~~Vesting and payment of incentive compensation awards will not change unless the ~~change~~recipient's employment is terminated or effectively terminated in ~~control~~connection with a change-in-control transaction, ~~is followed by termination of the executive’s employment or~~An effective termination ~~such as~~would include circumstances including, without limitation, material reduction in position, responsibilities, compensation, or other significant terms of employment.

The iPIP and the terms of applicable award agreements granted to our named executive officers include certain provisions relating to a termination of employment. Except as described below, all unvested iPIP points will be forfeited upon a termination of employment.

Termination for cause. If a participant's employment is terminated for "cause" (as defined in the iPIP), then all iPIP points, whether vested or unvested, will be forfeited.

Termination due to death or disability. If a participant's employment is terminated due to death or disability, then the ~~incentive compensation awards~~participant's number of vested iPIP points will be increased as of the date of such termination to the next vesting level. For example, if the participant was not yet vested in any points at the time of such termination, the participant's vested points will be increased to 40%. If there had been such a termination due to death or disability on December 31, 2019, the vested points of our named executive officers would have increased to the following amounts: Mr. Sugarman—33.94 points in the 2015-2016 iPIP pool, 22.0 points in the 2017-2018 iPIP pool, and 16.0 points in the 2019-2020 iPIP pool; Ms. Matis—7.65 points in the 2015-2016 iPIP pool, and 2.75 points in the 2017-2018 iPIP pool; and Mr. Alvarado—6.88 points in the 2017-2018 iPIP pool and 10.0 points in the 2019-2020 iPIP pool.


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Retirement. If a participant's employment is terminated as a result of the participant's "retirement" (defined in the iPIP and described below) prior to the first anniversary of the commencement of an iPIP pool, the unvested points are forfeited. If a participant's employment is terminated as a result of the participant's "retirement" following the first anniversary of the commencement of an iPIP pool, then 50% of the participant's unvested points in that pool are forfeited and the remaining 50% will continue to vest, ~~either~~pro rata, on the same schedule as if the participant had not retired. Any such points that vest following retirement will be forfeited if the participant competes with iStar, but the participant will not be required to repay any amounts previously received unless the board exercises its authority under our "clawback" policy, described on page 46. For purposes of this partial vesting, "retirement" is defined in ~~full or on prorated basis.~~

~~Under~~the iPIP to mean retirement from iStar after age 60, and with a sum of age plus years of service equal to at least 70.

Nina Matis served as a key member of our senior executive leadership team for more than 20 years. In March 2019, we announced Ms. Matis' retirement as chief legal officer, effective March 2019. She continued to serve as our vice chairman until July 1, 2019 to oversee a smooth transition. In special recognition of her contributions, the Compensation Committee approved special retirement arrangements, pursuant to which Ms. Matis received special bonus compensation for services during 2019, in the form of a payment of $650,000 paid in July 2019 and an additional payment of $250,000 paid in January 2020. In addition, she agreed to provide consulting services through December 31, 2019 and received aggregate payments of $125,000 for providing such services. Ms. Matis also was entitled to retain her previously-granted iPIP points, subject to continued vesting in accordance with the terms of ~~our LTIP and the applicable award agreements, if, on December 31, 2015, employment of our executive officers identified~~such awards.

Termination after a change in ~~this proxy statement had been terminated without cause following~~control. If, after a change in control, a participant's employment is terminated by iStar (or its successor) without cause or by the ~~executive officers identified~~participant for "good reason," (as defined in ~~this proxy statement would have earned~~the iPIP) then the participant's unvested ~~Units having the values, and shares would have been delivered~~iPIP points will continue to vest on the ~~vesting dates, set forth below:~~

Name
Market Value of Earned Units Upon Termination Without Cause ($)⁽¹⁾
Vesting/Delivery Date
Jay Sugarman $ 247,632
2/1/16
David DiStaso 102,635
2/1/16
34,478
12/31/16
13,493
12/31/17
Nina Matis 307,913
2/1/16


~~(1)~~	~~Based on the $11.73 per share NYSE closing price of our common stock as of December 31, 2015 and prorated vesting of the unvested Units in accordance with the terms of the award agreements.~~

~~Under the iPIP, the following rules shall apply upon a termination of employment:~~


~~(i)~~	~~if the participant’s employment is terminated for “cause”, then all Points, whether vested or unvested, shall be forfeited;~~

~~(ii)~~

if the participant’s employment is terminated due to the participant’s death or disability, then the participant’s amount of vested Points shall be increased as of the date of such termination to the next vesting level (for example, if the participant was not yet vested in any Points at the time of such termination, the participant’s vested Points shall be increased to 40%); if this circumstance had occurred on December 31, 2015, the vested Points of our executive officers identified in this proxy statement would have increased to the following amounts: Mr. Sugarman - 24.2 Points in 2013-2014 iPIP Pool and 8.0 Points in 2015-2016 iPIP Pool; Ms. Matis - 5.775 Points in 2013-2014 iPIP Pool and 1.4 Points in 2015-2016 iPIP Pool; and Mr. DiStaso - 1.375 Points in 2013-2014 iPIP Pool and 0.4 Points in 2015-2016 iPIP Pool.

~~(iii)~~

if the participant’s employment is terminated as a result of the participant’s “retirement” (i.e., retirement from the company after age 60, and with a sum of age plus years of service equal to at least 70) following the first anniversary of the commencement of an iPIP compensation pool, then 50% of the participant’s unvested Points in such pool shall continue to vest on the same schedule as if the participant had not incurred such termination (with such vesting occurring pro rata at each vesting level), except that any such Points that vested following retirement shall be forfeited if the participant competes with us (provided, that the participant shall not be required to repay any amounts previously received unless the provisions referred to below under “Clawback” apply); if Ms. Matis (our only executive officer identified in this proxy statement who qualified for “retirement” as defined) had retired on December 31, 2015, 6.3 of her unvested Points in 2013-2014 iPIP Pool and 2.1 Points of her unvested Points in 2015-2016 iPIP Pool would continue to vest on the same schedule as if she had not retired; and


~~(iv)~~	if, after a change in control, the participant’s employment is terminated by us without cause or by the participant for “good reason”, then the participant’s unvested Points shall continue to vest on the same schedule as if the participant had not incurred such termination.

~~For purposes of the table above, no values are being shown attributable to the incremental vesting of iPIP Points upon a termination of employment because the performance hurdles under the iPIP~~ had not ~~been met as of December 31, 2015.~~

~~Except as set forth above, upon a termination of employment, all unvested Points shall be forfeited.~~ incurred such termination.

Following a formal determination by the ~~Board~~board to proceed with a liquidation of the company, ~~a participant shall~~all participants will become 100% vested in ~~his or her Points~~their respective iPIP points if ~~the participant’s~~their employment is terminated thereafter by us without cause or by the participant for good reason.

The iStar Inc. Severance Plan provides separation benefits in the event an employee is terminated without cause, on terms that are available generally to all salaried employees.

~~Compensation~~


60\|iStar Inc. 2020 Proxy Statement

Table of Contents

Proposal 3—Ratification of the Appointment of Independent Registered Public Accounting Firm

The Audit Committee ~~Interlocks and Insider Participation~~

As of the date of this proxy statement, the members of the Compensation Committee are Robert W. Holman, Jr. (Chairman), Robin Josephs, John G. McDonald and Barry W. Ridings. No member of the Compensation Committee is or was formerly an officer or an employee of the company. None of our executive officers serves as a member of the board of directors, ~~or compensation committee of any entity that has one or more executive officers serving as a member~~with the concurrence of the board, has selected Deloitte & Touche LLP, an independent registered public accounting firm, to be our ~~board, nor has such interlocking relationship existed in the past.~~

~~Section 16(a) Beneficial Ownership Reporting Compliance~~

Section 16(a) of the Securities Exchange Act of 1934, as amended, requires our directors, executive officers and persons who own more than 10% of a registered class of our equity securities, to file with the SEC initial reports of ownership and reports of changes in ownership of common stock and other of our equity securities. Directors, officers and greater than 10% shareholders are required to furnish us with copies of all Section 16(a) forms they file. To our knowledge, based solely on a review of the copies of such reports furnished to us, duringauditors for the fiscal year ~~ended~~ending December 31, ~~2015, all Section 16(a) filing requirements applicable~~2019, subject to ratification by our ~~directors, officers and greater than 10% beneficial owners were met.~~

~~DIRECTOR COMPENSATION~~

~~Our compensation program for our non‑employee directors provides for payments~~shareholders. We expect a representative of annual retainers for directors, committee chairs and committee members and annual equity awards for directors. Directors do not receive additional fees for board or committee meetings attended. Currently, we pay all non‑employee directors an annual retainer of $100,000, paid in quarterly cash installments. The chairs of our board committees receive the following annual retainers, paid in quarterly cash installments: Audit Committee-$40,000; Compensation Committee-$40,000; and other committees-$16,000. Committee members receive the following annual retainers, paid in quarterly cash installments: Audit Committee-$15,000; Compensation Committee-$15,000; and other committees-$10,000. Each non‑employee director receives an annual equity award of $125,000, payable at their election in common stock equivalents (CSEs) or restricted shares of our common stock. The number of CSEs or restricted shares is based on the average NYSE closing price for our common stock for the 20 days priorDeloitte & Touche LLP to ~~the date of~~attend the annual shareholders meeting. Our Lead Director receives an additional award of $75,000, in consideration of her services as Lead Director, payable at her election in CSEs or restricted shares based on the average NYSE closing price for our common stock for the 20 days prior to the date of the annual shareholders meeting. The ~~CSEs~~representative may make a statement, and ~~restricted shares generally vest at the time of the next subsequent annual shareholders meeting. An amount equal~~will respond to ~~the dividends~~appropriate questions.

Accounting Fees and Services

Fees paid ~~on an equivalent number of shares of~~to Deloitte & Touche LLP, or Deloitte, our common stock is paid on the CSEs and restricted shares from the date of grant, as and when dividends are paid on the common stock. Under the Non‑Employee Directors’ Deferral Plan, directors have the opportunity to defer the receipt of some or all of their compensation in accordance with the provisions of the plan.

~~The table below summarizes the compensation information for our non-employee directors~~independent registered public accounting firm for the fiscal year ended December 31, ~~2015. Jay Sugarman, our chairman~~2019 and ~~chief executive officer, is not included in this table as he is our employee~~2018, and ~~receives no compensation for his services as a director.~~

Name Fees Earned or Paid in Cash ($)
Stock Awards
($)⁽¹⁾

All Other Compensation
($)⁽²⁾
Total ($)
Clifford De Souza $ 56,250
$ 98,096
$ —
$ 154,346
Robert W. Holman, Jr. 158,750
129,499
5,000
293,249
Robin Josephs 131,000
207,187
5,000
343,187
John G. McDonald 130,000
129,499
5,000
264,499
Dale Anne Reiss 145,000
129,499
5,000
279,499
Barry W. Ridings 138,000
129,499
5,000
272,499

~~(1)~~

Amounts included in the "Stock Awards" column reflect the grant date fair value of CSEs and restricted share awards made to directors in 2015 computed in accordance with FASB ASC Topic 718 (without regard to forfeitures). These awards were made to the directors under the Non-Employee Directors' Deferral Plan. The CSE and restricted share awards are valued using the closing price of our common stock on the date of grant. As of December 31, 2015, the directors held the following aggregate amounts of CSEs and/or restricted shares: Robert W. Holman, Jr.-43,591 CSEs and 8,993 restricted shares; Robin Josephs-75,513 CSEs and 14,388 restricted shares; John G. McDonald-78,529 CSEs; Dale Anne Reiss-43,591 CSEs and 8,993 restricted shares; Barry W. Ridings- 6,670 CSEs and 8,993 restricted shares; and Clifford De Souza 7,494 restricted shares.

~~(2)~~

Our directors are eligible to participate in our broad-based matching gifts program under which we will donate funds equal to contributions made by directors or employees to qualified nonprofit organizations, up to a maximum annual matching contribution per individual of $5,000 for directors and senior officers, $2,500 for other officers and $1,500 for other employees. Our directors are also eligible for reimbursement of the costs of attending continuing director education programs. Amounts included in the "All Other Compensation" column include any matching gifts made by us on behalf of the director and any education costs reimbursed by us to the director.

~~INDEMNIFICATION~~

We have entered into indemnification agreements with each of our directors and executive officers. The indemnification agreements provide that we will indemnify the directors and the executive officers to the fullest extent permitted by our charter and Maryland law against certain liabilities (including settlements) and expenses actually and reasonably incurred by them in connection with any threatened or pending legal action, proceeding or investigation to which any of them is, or is threatened to be, made a party by reason of their status as our director, officer or agent, or by reason of their serving as a director, officer or agent of another company at our request. The Maryland General Corporation Law, or MGCL, permits a corporation to indemnify its present and former directors and officers, among others, against judgments, penalties, fines, settlements and reasonable expenses actually incurred by them in connection with any proceeding to which they may be made, or threatened to be made, a party by reason of their service in those or other capacities unless it is established that (a) the act or omission of the director or officer was material to the matter giving rise to the proceeding and (i) was committed in bad faith or (ii) was the result of active and deliberate dishonesty, (b) the director or officer actually received an improper personal benefit in money, property or services or (c) in the case of any criminal proceeding, the director or officer had reasonable cause to believe that the act or omission was unlawful. However, under the MGCL, a Maryland corporation may not indemnify for an adverse judgment in a suit by or in the right of the corporation or for a judgment of liability on the basis that personal benefit was improperly received, unless in either case a court orders indemnification and then only for expenses. Under the MGCL, a Maryland corporation is required to indemnify any director or officer who has been successful, on the merits or otherwise, in the defense of any proceeding to which he or she is made, or threatened to be made, a party by reason of his or her service in that capacity, unless the charter requires otherwise, which our charter does not. In addition, the MGCL permits a corporation to advance reasonable expenses to a director or officer upon the corporation’s receipt of (a) a written affirmation by the director or officer of his or her good faith belief that he or she has met the standard of conduct necessary for indemnification by the corporation and (b) a written undertaking by him or her or on his or her behalf to repay the amount paid or reimbursed by the corporation if it is ultimately be determined that the standard of conduct was not met. Our charter requires us to indemnify and advance expenses to our directors and officers to the full extent required

~~or permitted by Maryland law. In addition, we have obtained directors and officers liability insurance, which covers our directors and executive officers.~~

~~ACCOUNTING FEES AND SERVICES~~

~~Fees paid~~ to PricewaterhouseCoopers LLP, or PwC, our independent registered public accounting firm ~~during~~for the ~~last two~~ fiscal ~~years~~year ended December 31, 2017, were as follows:

Type of fee	2019 (Deloitte)		2018 (Deloitte)		2019 (PwC)		2018 (PwC)


Audit fees	$	1,293,500	$	928,000	$	57,500	$	170,000

Audit-related fees		30,000		513,550	$	290,000		—

Tax fees		888,860		440,024		—		—

All other fees		3,000		—		24,256		980

Total fees	$	2,215,360	$	1,881,574	$	371,756	$	170,980

Audit ~~Fees:~~Fees. ~~The aggregate~~These fees were incurred ~~during the fiscal years ended December 31, 2015 and December 31, 2014~~ for professional services rendered ~~by PricewaterhouseCoopers LLP~~ in connection with ~~its~~ integrated audits of our consolidated financial statements and our internal control over financial reporting, ~~and its~~ limited reviews of our unaudited consolidated interim financial statements ~~were approximately $1,541,000~~ and ~~$1,706,000, respectively.~~comfort letters. PwC's fees for 2019 and 2018 relate to work associated with the issuance of the 2017 consolidated financial statements included in our 2019 and 2018 Forms 10-K.

Audit-Related ~~Fees:~~Fees. ~~The aggregate~~These fees were incurred ~~during the fiscal years ended December 31, 2015 and December 31, 2014~~ for assurance and related services ~~rendered by PricewaterhouseCoopers LLP~~ that are reasonably related to the performance of the audit or review of our financial statements and are not disclosed under "Audit ~~Fees" above, were approximately $13,000 and $13,000, respectively.~~Fees." These audit-related fees included fees related to ~~the issuance~~Deloitte and PwC's review of ~~mortgage servicing compliance reports.~~SEC filings.

Tax ~~Fees:~~Fees. ~~The aggregate~~These fees were incurred ~~during the fiscal years ended December 31, 2015 and December 31, 2014~~ for professional services rendered ~~by PricewaterhouseCoopers LLP for~~in connection with tax compliance, tax advice, and tax ~~planning were approximately $471,406 and $302,176, respectively.~~planning. These services included income tax compliance and related tax services.

All Other ~~Fees:~~Fees. NoThe 2019 fees were incurred ~~during the years ended December 31, 2015 or December 31, 2014~~ for ~~other~~ professional services rendered by ~~PricewaterhouseCoopers LLP.~~PwC in connection with insurance claims.

Our Audit Committee is responsible for retaining and terminating our independent registered public accounting firm (subject, if applicable, to shareholder ratification) and for approving the performance of any non-audit services by the independent registered public accounting firm. In addition, the Audit Committee is responsible for reviewing and evaluating the qualifications, performance, and independence of the lead partner of the independent registered public accounting firm and for presenting its conclusions ~~with respect to the independent registered public accounting firm~~on those matters to the full board.


Proposal 3—Ratification of the Appointment of Independent Registered Public Accounting Firm · Accounting Fees and Services		iStar Inc. 2020 Proxy Statement\|61

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The Audit Committee has the sole authority to approve all audit engagement fees and terms, as well as significant non-audit services, ~~with~~involving the independent registered public accounting firm. During fiscal ~~2015,~~2019, the Audit Committee approved all audit engagement fees and terms ~~with PricewaterhouseCoopers LLP,~~involving Deloitte, as well as all significant non-audit services performed by ~~PricewaterhouseCoopers LLP.~~Deloitte.


62\|iStar Inc. 2020 Proxy Statement

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Report of the Audit Committee

The Audit Committee oversees the financial reporting process of iStar Inc. on behalf of the board of directors in accordance with our charter. The board has determined that all members of the Audit Committee meet the independence requirements of both the Securities and Exchange Commission, or SEC, and the New York Stock Exchange, or NYSE. The board also has determined that all members of the Audit Committee are "audit committee financial experts" within the meaning of the SEC rules, and are financially literate and have accounting or related financial management expertise, as such qualifications are defined under NYSE rules. We operate under a written charter approved by the board, consistent with the corporate governance rules issued by the SEC and the NYSE. Our charter is available on iStar's website atwww.istar.com (under "Investors" and then "Governance & Proxy") and will be provided in print, without charge, to any shareholder who requests a copy.

iStar's management is responsible for executing the financial reporting process and preparing the quarterly and annual consolidated financial statements, including maintaining a system of internal controls over financial reporting, as well as disclosure controls and procedures.

We are directly responsible for the appointment, compensation, retention, oversight, and termination of the external auditors. We have appointed Deloitte & Touche LLP, or Deloitte, an independent registered public accounting firm, to audit iStar's consolidated financial statements for the year ending December 31, 2020.

The independent registered public accounting firm is responsible for auditing the effectiveness of iStar's internal controls over financial reporting and for expressing its opinion thereon, in addition to auditing the annual consolidated financial statements and expressing an opinion whether those financial statements conform to generally accepted accounting principles in the United States. We also approve the engagement of an accounting firm to assist management in preparing documentation, testing and evaluating internal controls over financial reporting, and reviewing the performance of those controls. We do not prepare financial statements or conduct audits.

In its capacity as iStar's independent registered public accounting firm for 2019, Deloitte issued a report on the consolidated financial statements as of and for the year ended December 31, 2019. In connection with the December 31, 2019, audited consolidated financial statements, we have:

O: reviewed and discussed with management and the independent registered public accounting firm iStar's internal controls over financial reporting, including a review of management's and the independent registered public accounting firm's assessments of and reports on the effectiveness of internal controls over financial reporting and any significant deficiencies or material weaknesses;
O: reviewed and discussed with management and the independent registered public accounting firm iStar's audited financial statements, including discussions regarding critical accounting policies, other appropriate financial accounting and reporting principles and practices, the quality of such principles and practices, and the reasonableness of significant judgments;
O: discussed with the independent registered public accounting firm the items that are required to be discussed by Statement on Auditing Standards No. 61, Communication with Audit Committees, as amended by Statement on Auditing Standards No. 90, Audit Committee Communications; and
O: reviewed and considered the written disclosures in the letter received from Deloitte, as required by the Public Company Accounting Oversight Board, regarding the independent accountant's communications with the Audit Committee regarding independence, including a discussion about its independence from iStar and management.


Report of the Audit Committee		iStar Inc. 2020 Proxy Statement\|63

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Based on the reviews and discussions above, and subject to the limitations on the role and responsibilities of the Audit Committee referred to above and in the Audit Committee charter in effect in 2019, we recommended to the board that the audited consolidated financial statements for 2019 be included in iStar's Annual Report on Form 10-K for the year ended December 31, 2019, for filing with the SEC. The board approved our recommendation.


		Submitted by the Audit Committee
		Clifford De Souza (Chairman) Robin Josephs Barry W. Ridings

The above report will not be deemed to be incorporated by reference into any filing by us under the Securities Act of 1933 or the Securities Exchange Act of 1934 except to the extent that we specifically incorporate the same by reference.


64\|iStar Inc. 2020 Proxy Statement

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~~SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT~~

Stock Ownership Information

Security Ownership of Certain Beneficial Owners and Management

The following table sets forth ~~certain~~ information available to us ~~as of March 23, 2016 (except as otherwise indicated)~~ with respect to any common stock and Series D preferred stock owned by our directors, nominees for director, ~~and~~ executive officers, and any individual or group of shareholders known to be the beneficial owner of more than 5% of our issued and outstanding common stock and Series D preferred ~~stock.~~stock as of March 20, 2020. This table includes options, if any, that are currently exercisable or exercisable within 60 days of the date of this proxy statement, and CSEs and restricted shares of our common stock awarded to non-employee directors under the iStar Inc. Non-Employee ~~Directors~~Directors' Deferral Plan ~~which~~that are or will be fully vested within 60 days.

Name and Address of Beneficial Owner⁽¹⁾

Common Stock Beneficially Owned⁽¹⁾

% of Basic Common Stock Outstanding⁽²⁾

Series D Preferred Stock Beneficially Owned⁽¹⁾

% of Series D Preferred Stock Outstanding⁽²⁾
Clifford De Souza⁽³⁾
7,494
⁽⁴⁾
*

David DiStaso⁽³⁾
93,994
⁽⁵⁾
*
607
⁽⁵⁾
*
Robert W. Holman, Jr.⁽³⁾
118,769
⁽⁶⁾
*

Robin Josephs⁽³⁾
162,512
⁽⁷⁾⁽⁸⁾
*

Nina Matis⁽³⁾
372,611
⁽⁹⁾
*

John G. McDonald⁽³⁾
118,529
⁽¹⁰⁾
*

Dale Anne Reiss⁽³⁾
78,529
^(11)(12)
*
900
*
Barry W. Ridings⁽³⁾
41,608
⁽¹³⁾
*

Jay Sugarman⁽³⁾
2,600,880
⁽¹⁴⁾
3.44 % 2,000
*
Apollo Capital Management, L.P.
⁽¹⁵
⁾

⁽¹⁵
⁾

BlackRock, Inc. 6,259,120
⁽¹⁶⁾
8.29 %
Diamond Hill Capital Management, Inc. 7,261,392
⁽¹⁷⁾
9.62 %
FMR LLC 4,435,191
⁽¹⁸⁾
5.87 %
Morgan Stanley 4,507,988
⁽¹⁹⁾
5.97 %
The Vanguard Group 5,441,597
⁽²⁰⁾
7.21 %
All executive officers, directors and nominees for director as a group (9 persons) 3,594,926
4.76 %

Name and Address of Beneficial Owners(1)


Jay Sugarman(3)	2,565,163	(8)	3.32	%	2,000	0.05	%

Marcos Alvarado(3)	37,875	(4)	*		—	—

Clifford De Souza(3)	57,004	(5)	*		—	—

Robin Josephs(3)	230,403	(6)	*		—	—

Barry W. Ridings(3)	91,477	(7)	*		—	—

Anita Sands(3)	—		—		—	—

BlackRock, Inc. 55 E. 52nd Street New York, New York 10055	10,634,758	(9)	13.77	%	—	—

EJF Capital LLC 2107 Wilson Boulevard Suite 410 Arlington, VA 22201	4,803,980	(10)	6.22	%	—	—

FMR LLC 245 Summer Street Boston, Massachusetts 02210	4,161,573	(11)	5.39	%	—	—

UBS Group AG Bahnhofstrasse 45 PO Box CH-8021 Zurich, Switzerland	6,607,801	(12)	8.55	%	—	—

The Vanguard Group 100 Vanguard Blvd., Malvern, Pennsylvania 19355.	9,869,558	(13)	12.78	%	—	—

Loomis Sayles & Co., L.P. One Financial Center Boston, MA 02111	5,209,767	(14)	6.74	%

All executive officers, directors and nominees for director as a group (7 persons)	2,996,256		3.88	%	2,000	0.05	%

*: Less than 1%.
(1): Except as otherwise indicated and subject to applicable community property laws and similar statutes, the person listed as the beneficial owner of shares has sole voting power and dispositive power with respect to the shares.
(2): As of March 20, 2020, 77,252,306 shares of common stock were deemed outstanding for purposes of this table, of which 77,230,747 were entitled to vote, and 4,000,000 shares of Series D preferred stock were outstanding and entitled to vote.
(3): c/o iStar Inc., 1114 Avenue of the Americas, 39th Floor, New York, NY 10036.


* Stock Ownership Information · Security Ownership of Certain Beneficial Owners and Management	~~Less than 1%.~~	iStar Inc. 2020 Proxy Statement\|65

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(4): Includes 37,875 shares owned directly by Mr. Alvarado.
(5): Includes 42,670 shares owned directly by Mr. De Souza and 14,334 restricted shares of common stock owned directly by Mr. De Souza that are or will be fully vested within 60 days.
(6): Includes 114,780 shares of common stock owned indirectly by Ms. Josephs through a family trust, 13,140 shares owned indirectly through an Individual Retirement Account, 79,549 CSEs held under the iStar Inc. Non-Employee Directors' Deferral Plan that are fully vested, and 22,934 restricted shares of common stock that are or will be fully vested within 60 days.
(7): Includes 70,114 shares held directly by Mr. Ridings, 7,029 CSEs held under the iStar Inc. Non-Employee Directors' Deferral Plan that are fully vested, and 14,334 restricted shares of common stock that are or will be fully vested within 60 days.
(8): Includes 2,524,619 shares of common stock owned directly by Mr. Sugarman and 40,544 shares owned indirectly through Mr. Sugarman's spouse.
(9): This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2019, as amended, filed with the SEC by BlackRock, Inc. and a review of public filings by the funds reported as beneficial owners in that Schedule 13G.
(10): This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2019, as amended, filed with the SEC by EFJ Capital LLC. The shares are held by EJF Debt Opportunities Master Fund, L.P., EJF Debt Opportunities Master Fund II, LP, and EJF Income Fund, LP.
(11): This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2019, as amended, filed with the SEC by FMR LLC.
(12): This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2019, filed with the SEC by UBS Group AG.
(13): This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2019, as amended, filed with the SEC by The Vanguard Group.
(14): This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2019, as amended, filed with the SEC by Loomis Sayles & Co., L.P.

Section 16(a) Beneficial Ownership Reporting Compliance

Section 16(a) of the Securities Exchange Act of 1934 requires our directors, executive officers, and persons who own more than 10% of a registered class of our equity securities to file with the SEC initial reports of ownership and reports of changes in ownership of common stock and our other equity securities. Directors, officers, and greater than 10% shareholders are required to furnish us with copies of all Section 16(a) forms they file. To our knowledge, based solely on a review of the copies of such reports furnished to us, during the fiscal year ended December 31, 2019, all Section 16(a) filing requirements applicable to our directors, officers, and greater than 10% beneficial owners were met.


~~(1)~~ 66\|iStar Inc. 2020 Proxy Statement	Except as otherwise indicated and subject to applicable community property laws and similar statutes, the person listed as the beneficial owner of shares has sole voting power and dispositive power with respect to the shares.

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~~(2)~~	~~As of March 23, 2016, 75,500,999 shares of common stock were outstanding, of which 75,310,955 were entitled to vote,~~ Certain Relationships and ~~4,000,000 shares of Series D preferred stock were outstanding and entitled to vote.~~Related Party Transactions


~~(3)~~	~~c/o iStar Inc., 1114 Avenue of the Americas, 39th Floor, New York, NY 10036.~~


~~(4)~~	~~Includes 7,494 restricted shares of common stock owned directly by Mr. De Souza which are or will be fully vested within 60 days.~~


~~(5)~~	Includes 93,994 shares of common stock and 607 shares of Series D preferred stock owned directly by Mr. DiStaso. Does not include 37,704 unvested restricted stock units awarded to Mr. DiStaso, which represent the right to receive shares of common stock if and when the units vest.


~~(6)~~	Includes 40,240 shares owned indirectly by Mr. Holman through a partnership, 25,945 shares owned directly, 43,591 CSEs held under the iStar Inc. Non-Employee Directors Deferral Plan which are fully vested and 8,993 restricted shares of common stock which are or will be fully vested within 60 days.


~~(7)~~	Includes 15,977 shares of common stock owned indirectly by Ms. Josephs through a family trust, 13,140 shares owned indirectly through an Individual Retirement Account, 43,494 shares owned directly, 75,513 CSEs held under the iStar Inc. Non-Employee Directors Deferral Plan which are fully vested and 14,388 restricted shares of common stock which are or will be fully vested within 60 days.


~~(8)~~	~~Ms. Josephs also indirectly beneficially owns 3,030 shares of non-voting Series F preferred stock.~~


~~(9)~~	~~Includes 372,611 shares of common stock owned directly by Ms. Matis.~~


~~(10)~~	Includes 28,000 shares of common stock owned indirectly by Professor McDonald through an Individual Retirement Account, 12,000 shares owned indirectly through a family trust and 78,529 CSEs held under the iStar Inc. Non-Employee Directors Deferral Plan which are or will be fully vested within 60 days.


~~(11)~~	Includes 25,945 shares held directly by Ms. Reiss, 43,591 CSEs held under the iStar Inc. Non-Employee Directors Deferral Plan which are fully vested and 8,993 restricted shares of common stock which are or will be fully vested within 60 days.


~~(12)~~	~~Ms. Reiss also indirectly beneficially owns 2,768 shares of non-voting Series E preferred stock and 4,142 shares of non-voting Series F preferred stock.~~


~~(13)~~	Includes 25,945 shares held directly by Mr. Ridings, 6,670 CSEs held under the iStar Inc. Non-Employee Directors Deferral Plan which are fully vested and 8,993 restricted shares of common stock which are or will be fully vested within 60 days.


~~(14)~~	~~Includes 2,560,336 shares of common stock owned directly by Mr. Sugarman and 40,544 shares owned indirectly through Mr. Sugarman's spouse.~~

~~(15)~~

Based solely on a Schedule 13G, dated December 31, 2015, as amended, filed with the SEC by Apollo Capital Management, L.P. and certain affiliated persons, many of which disclaim beneficial ownership of such shares, (i) various entities affiliated with Apollo Capital Management, L.P. hold undisclosed amounts of our common stock, 1.5% convertible senior notes due 2016, 3.0% convertible senior notes due 2016 and 4.5% Series J cumulative perpetual preferred stock; and (ii) if the Apollo entities, and only the Apollo entities, converted all of their convertible securities, they would hold up to 7,467,726 shares of our common stock. This amount of holdings would represent approximately 9.89% of our common stock outstanding. This shareholder's address is 9 W. 57^th ~~Street, 43~~^rd ~~Floor, New York, NY 10019. According to the 13G.~~


~~(16)~~	This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2015, filed with the SEC by BlackRock, Inc. and a review of public filings by the funds reported as beneficial owners in that Schedule 13G. This shareholder's address is 55 E. 52nd Street, New York, NY 10055.


~~(17)~~	This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2015, as amended, filed with the SEC by Diamond Hill Capital Management, Inc. This shareholder's address is 325 John H. McConnell Blvd., Suite 200, Columbus, OH 43215.


~~(18)~~	This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2015, as amended, filed with the SEC by FMR LLC. This shareholder's address is 245 Summer Street, Boston, MA 02210.


~~(19)~~	~~This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2015, filed with the SEC by Morgan Stanley. This shareholder's address is 1585 Broadway, New York, NY 10036.~~


~~(20)~~	This beneficial ownership information is based solely on a Schedule 13G, dated December 31, 2015, filed with the SEC by The Vanguard Group. This shareholder's address is 100 Vanguard Blvd., Malvern, PA 19355.

~~CERTAIN RELATIONSHIPS AND RELATED TRANSACTIONS~~

~~Policies and Procedures With Respect to Related Party Transactions~~

It is the policy of our board of directors that all transactions between usiStar and a ~~related party~~"related party" must be approved or ratified by at least a majority of the members of ~~our~~the board who have no financial or other interest in the transaction. AFor this purpose, a related party includes any director or executive officer, any nominee for director, any shareholder owning 5% of more of our outstanding shares, and any immediate family member of any such person.

In determining whether to approve or ratify a related party transaction, the board will take into account, among other factors it deems appropriate, whether the ~~related party~~ transaction is on terms no less favorable than terms generally available to an unaffiliated ~~third‑~~third party under the same or similar circumstances, and the extent of the related ~~party’s~~party's interest in the transaction. No director will participate in any discussion or approval of a related party transaction for which ~~he or she~~such director is a related party, except that ~~the~~such a director will provide all material information concerning the related party transaction to our board.

If a related party transaction will be ongoing, ~~our~~the board may establish guidelines for ~~our~~ management to follow in its ongoing dealings with the related party. The board may delegate to our Nominating and ~~Corporate~~ Governance Committee the authority to review and assess, on at least an annual basis, any such ongoing relationships with the related party to ~~see that~~confirm they are in compliance with the ~~board’s~~board's guidelines.

All related party transactions will be disclosed in our applicable filings with the SEC as required under SEC rules.

~~PROPOSALS~~

~~PROPOSAL 1:~~

~~ELECTION OF DIRECTORS~~

~~The~~

Our subsidiary is the external manager of Safehold Inc. ("SAFE") pursuant to a management agreement, more fully described in our Annual Report on Form 10-K for the fiscal year ended December 31, 2019 [insert link/cross-reference]. We are also SAFE's largest shareholder. Our board has adopted specific procedures with respect to transactions in which SAFE is also a participant: such transactions involving an investment or asset value of more than $60 million must be approved by majority of our independent directors on our Board, ~~has nominated~~and transactions involving an investment or asset value of $60 million or less must be approved by a majority of independent directors ~~Sugarman, De Souza, Holman, Josephs, McDonald, Reiss~~on our Investment Committee.

We have participated in certain of SAFE's ground lease investment transactions, as a seller of land or by providing financing to SAFE's ground lease tenants. These transactions were approved in accordance with our policy with respect to transactions in which SAFE is also a participant, described above. Here is a summary of these transactions:

O: In October 2019, SAFE acquired land and ~~Ridings~~SAFE's Ground Lease tenant acquired the leasehold from a venture in which we have a 50% ownership interest. In addition, we provided a $22.0 million loan to ~~be elected to hold office~~SAFE's Ground Lease tenant for ~~a term of one year, until~~ the ~~next annual meeting and until their successors have been elected and qualified.~~

~~Recommendation Regarding the Election of Directors~~

~~The board recommends that you vote FOR electing the seven named nominees as our directors.~~

~~PROPOSAL 2:~~

~~RATIFICATION OF APPOINTMENT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM~~

~~The Audit Committee~~acquisition of the leasehold. We sold the loan at par to a third-party in November 2019.

In August 2019, we acquired the leasehold interest in a net lease asset and simultaneously entered into a new 99-year Ground Lease with SAFE.

In February 2019, we acquired the leasehold interest in an office property and simultaneously entered into a new 98-year Ground Lease with SAFE.

In January 2019, we committed to provide a $13.3 million loan to the ground lessee of a Ground Lease originated at SAFE. The loan is for the conversion of an office building into a multi-family property in Washington, DC.

In May 2018, we provided a $19.9 million leasehold mortgage loan to the ground lessee of a Ground Lease originated at SAFE. The loan was for the acquisition of two multi-tenant office buildings in Atlanta, GA. The loan was repaid in full in November 2019.


Certain Relationships and Related Party Transactions		iStar Inc. 2020 Proxy Statement\|67

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O: In August 2017, we committed to provide a $24.0 million loan to the ground lessee of a Ground Lease originated at SAFE. The loan was for the renovation of a medical office building in Atlanta, GA. We funded $18.4 million of the loan, which was fully repaid in August 2019.

As previously reported in our SEC filings in respect of 2019, during the year, we purchased 22.3 million shares of SAFE common stock (including partnership interests in SAFE's operating partnership that were subsequently exchanged for shares of SAFE common stock) in private placement transactions from SAFE for an aggregate purchase price of $548 million.


68\|iStar Inc. 2020 Proxy Statement

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Information about the Annual Meeting of Shareholders |To Be Held May 21, 2020

We are making this proxy statement available to holders of our common stock and holders of our 8.00% Series D preferred stock on or about April 10, 2020, in connection with the solicitation by our board of directors ~~with the concurrence~~of proxies to be voted at our 2020 annual meeting of shareholders or at any postponement or adjournment of the ~~board,~~annual meeting.

This proxy statement is accompanied by our Annual Report for the year ended December 31, 2019. The Annual Report, including our financial statements at December 31, 2019, is available on our website atwww.istar.com by choosing "Investors" and then "Governance & Proxy," or you can obtain a print copy, without charge, by contacting Investor Relations at:



			(212) 930-9400				iStar Inc. Attention: Investor Relations 1114 Avenue of the Americas 39th Floor New York, NY 10036

The information found on, or accessible through, our website is not incorporated into, and does not form a part of, this proxy statement or any other report or document we file with or furnish to the SEC. We urge you to authorize a proxy to vote your shares—either by mail, by telephone, or online—at your earliest convenience, even if you plan to attend the annual meeting in person.

Who is entitled to vote at the meeting?

Only holders of record of our common stock and our Series D preferred stock at the close of business on March 20, 2020, are entitled to receive notice of and to vote at the annual meeting or at any postponement or adjournment of the meeting. On the record date, there were 77,230,747 shares of common stock and 4,000,000 shares of Series D preferred stock outstanding and entitled to vote.

What constitutes a quorum?

In order to have a quorum at the annual meeting, we need the presence, either in person or by proxy, of the holders of enough outstanding common stock and Series D preferred stock, in the aggregate, to cast a majority of the votes entitled to be cast at the meeting.

What are the voting rights of shareholders?

Each shareholder is entitled to one vote for each share of common stock owned, and 0.25 votes for each share of Series D preferred stock owned, on the record date.


Information about the Annual Meeting of Shareholders		iStar Inc. 2020 Proxy Statement\|69

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What vote is needed to approve each proposal?

Assuming a quorum is present in person or by proxy at the annual meeting, the proposals require the following votes:


Proposal		Votes Needed to Pass	Effect of Abstentions and Broker Non-Votes

1	Election of six directors	Each nominee must receive a plurality of the votes cast by the holders of our common stock and Series D preferred stock, all voting as one class	Counted toward a quorum but no effect on the vote results

2	Non-binding advisory vote to approve executive compensation	The affirmative vote of a majority of the votes cast by the holders of our common stock and Series D preferred stock, all voting as one class	Counted toward a quorum but no effect on the vote results

3	Ratification of the appointment of Deloitte & Touche LLP as our independent registered public accounting firm	The affirmative vote of a majority of the votes cast by the holders of our common stock and Series D preferred stock, all voting as one class	Abstentions will be counted toward a quorum but will have no effect on the vote results. There should not be any broker non-votes

For the approval of any other matters properly presented at the meeting for shareholder approval, the affirmative vote of a majority of the votes cast by the holders of our common stock and Series D preferred stock, all voting as one class, is required.

How can I attend the annual meeting?

The annual meeting will be a completely virtual meeting of shareholders, which will be conducted exclusively by webcast. You are entitled to participate in the annual meeting only if you were a shareholder of the Company as of the close of business on the record date, March 20, 2020, or if you hold a valid proxy for the annual meeting. No physical meeting will be held. You will be able to attend the annual meeting online and submit your questions during the meeting by visitingwww.meetingcenter.io/270691408. You also will be able to vote your shares online by attending the annual meeting by webcast.

To participate in the annual meeting, you will need to review the information included on your Notice, on your proxy card or on the instructions that accompanied your proxy materials. The password for the meeting isSFI2020.

If you hold your shares through an intermediary, such as a bank or broker, you must register in advance using the instructions below.

The online meeting will begin promptly at 9:00 a.m., Eastern Time. We encourage you to access the meeting prior to the start time leaving ample time for the check in. Please follow the registration instructions as outlined in this proxy statement.

How do I register to attend the Annual Meeting virtually on the Internet?

If you are a registered shareholder (i.e., you hold your shares through our transfer agent, Computershare), you do not need to register to attend the Annual Meeting virtually on the Internet. Please follow the instructions on the notice or proxy card that you received. If you hold your shares through an intermediary, such as a bank or broker, you must register in advance to attend the Annual Meeting virtually on the Internet.


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To register to attend the Annual Meeting online by webcast you must submit proof of your proxy power (legal proxy) reflecting your iStar holdings along with your name and email address to Computershare. Requests for registration should be directed to:

Computershare
iStar Legal Proxy
P.O. Box 43001
Providence, RI 02940-3001

Requests for registration must be labeled as "Legal Proxy" and be received no later than 5:00 p.m., Eastern Time, on May 15, 2020.

You will receive a confirmation of your registration by email after we receive your registration materials.

Why are you holding a virtual meeting instead of a physical meeting?

In light of health, transportation, and other logistical issues raised by the spread of coronavirus, or COVID-19, under the current circumstances we have no assurance that we would be able to hold a physical meeting that is safe for our participants. We believe that hosting a virtual meeting will enable more of our shareholders to participate in the meeting since our shareholders can participate from any location with Internet access.

What are broker non-votes?

A "broker non-vote" occurs when a broker, bank, or other nominee does not have discretionary authority as to certain shares to vote on a particular matter, and has ~~selected PricewaterhouseCoopers LLP,~~not received voting instructions on that matter from the beneficial owner of those shares. Under current NYSE rules, a broker, bank, or other nominee does not have discretionary authority to vote shares without specific voting instructions from the beneficial owner in an election of directors, or on a resolution to approve executive compensation. Brokers, banks, and other nominees do have discretionary authority to vote shares without specific voting instructions on the ratification of the appointment of an independent registered public accounting ~~firm,~~firm.

How is my vote counted?

If you properly vote your proxy prior to ~~be our auditors for the fiscal year ending December 31, 2016, subject to ratification by our shareholders. We expect a representative of PricewaterhouseCoopers LLP to attend~~ the annual meeting, the shares that the proxy represents will be voted in the manner you direct. If your proxy does not specify a choice regarding one or more proposals, your shares will be voted FOR the election of directors, FOR the resolution to ~~make~~approve, on a ~~statement, if he or she desires,~~non-binding, advisory basis, executive compensation, and ~~to respond to appropriate questions.~~

~~Recommendation Regarding Ratification of Appointment of PricewaterhouseCoopers LLP~~

~~The board recommends that you vote~~ FOR the ratification of the appointment of ~~PricewaterhouseCoopers LLP, an~~the independent registered public accounting ~~firm, to~~firm.

Votes cast in person or by proxy at the annual meeting will be ~~our auditors~~tabulated by the election inspectors appointed for the ~~fiscal year ending December 31, 2016.~~meeting, who also will determine whether a quorum is present. If your shares are held by a broker, bank, or other nominee (i.e., in "street name"), you will receive instructions from your nominee that you must follow in order to have your shares voted. Street name shareholders who wish to vote in person at the meeting will need to obtain a proxy from the broker, bank, or other nominee that holds their shares of record.

Can I change my vote after I submit my proxy card or vote electronically?

If you authorize a proxy to vote your shares, you may revoke it at any time before it is voted by:

O: submitting voting instructions at a later time via the Internet or by telephone before those voting facilities close;
O: giving written notice bearing a date later than the date of the proxy to our Secretary expressly revoking the proxy;


Information about the Annual Meeting of Shareholders		iStar Inc. 2020 Proxy Statement\|71

~~PROPOSAL 3:~~

~~SHAREHOLDER NON‑BINDING ADVISORY VOTE ON EXECUTIVE COMPENSATION~~

~~Pursuant~~

Table of Contents

O: signing and forwarding to us a proxy dated later; or
O: attending the annual meeting and personally voting the common stock or Series D preferred stock that you own of record. Merely attending the annual meeting will not revoke a proxy.

Who pays the costs of solicitation?

We will pay the costs of soliciting proxies from our shareholders. In addition to solicitation by mail, certain of our directors, officers, and employees may solicit the return of proxies by telephone, fax, personal interview, or otherwise without being paid additional compensation. We will reimburse brokerage firms and other persons representing the beneficial owners of our shares for their reasonable expenses in forwarding proxy solicitation materials to the Dodd‑Frank Wall Street Reform and Consumer Protection Act, or the Dodd‑Frank Act, and rules adopted by the SEC thereunder, our shareholders are entitled to cast a non‑binding, advisory vote to approve the compensation of our executive officers identifiedbeneficial owners in ~~this proxy statement, commonly referred to as the Say on Pay vote. We conduct an annual, non‑binding Say on Pay vote consistent~~accordance with the ~~recommendation of a majority of our shareholders expressed by vote at our 2011 Annual Meeting.~~

~~Shareholders are urged to read the section of this~~ proxy ~~statement captioned “EXECUTIVE COMPENSATION”,~~solicitation rules and ~~especially the Compensation Discussion and Analysis, which discusses our compensation philosophy and how our compensation policies and practices implement our philosophy.~~

As described more fully in that discussion, our compensation programs have been designed to create a strong connection between executive pay and our business performance, including shareholder value creation, and achieve the following objectives:

To encourage our key executives to improve business performance and increase shareholder value by providing a mix of current compensation and long‑term rewards that is variable and balanced between salary and performance‑based pay and includes cash, equity compensation and other benefits.

~~To align shareholder and employee interests by compensating employees for improving our business performance and increasing the value of the company, to the benefit of our shareholders.~~

To promote these objectives, a significant part of executive compensation is based on accomplishing achievements that increase the value of the company. We believe this approach helps us achieve our objectives and promote the interests of our shareholders.

In conjunction with improving economic and commercial real estate market conditions, we have continued to make meaningful progress towards achieving a number of our strategic corporate objectives. Our compensation actions during 2015 take into account the performance and accomplishments of our management team towards achieving our current and long‑term strategic, business and financial goals, and reflect our continuing efforts to enhance the alignment between our executive incentives and results realized by our shareholders.

~~We are requesting your non‑binding vote on the following resolution:~~

RESOLVED, that the Company’s shareholders approve, on a non‑binding advisory basis, the compensation of the executive officers identified in the Proxy Statement for the 2016 Annual Meeting of Shareholders pursuant to the compensation disclosure rulesregulations of the SEC ~~including the Compensation Discussion and Analysis, the Summary Compensation Table~~ and the NYSE. We have engaged Alliance Advisors LLC to solicit proxies on our behalf in connection with our 2020 annual meeting of shareholders and to provide other ~~related tables and narrative disclosure~~

~~Although your vote is non‑binding and~~ advisory ~~the board and the Compensation Committee will take into account the outcome~~services for a fee of ~~the vote when considering future executive compensation arrangements.~~

~~Recommendation Regarding the Shareholder Advisory Vote on Executive Compensation~~

~~The board recommends that you vote FOR the Say on Pay resolution to approve the compensation of the executive officers identified in this proxy statement.~~

~~OTHER MATTERS~~

$17,500, plus expenses.

When ~~Are Shareholder Proposals Due~~are shareholder proposals due for the ~~2017 Annual Meeting?~~

~~In accordance with Rule 14a‑8 under the Securities Exchange Act of 1934, as amended, shareholder~~2021 annual meeting?

Shareholder proposals intended to be included in our proxy materials and presented at the 2021 annual meeting ~~to be held in 2017~~ must be sent in writing, by certified mail, return receipt requested, to us at our principal office, addressed to our ~~Secretary, and~~Secretary. Such proposals must be received by us no later than December ~~8, 2016 for inclusion in the 2017 proxy materials. In order for~~X, 2020.

If you wish to submit a shareholder proposal ~~submitted outside of Rule 14a‑8~~ to be considered at our ~~2017~~2021 annual meeting but not included in our proxy materials, the proposal must contain the information required by our ~~bylaws and be received by us in accordance with our~~ bylaws. ~~Pursuant to our current bylaws, shareholder~~Such proposals ~~made outside of Rule 14a‑8 under the Exchange Act~~ must be submitted ~~not later than~~between November X, 2020, and December ~~8, 2016 and not earlier than November 8, 2016; provided, however, in the event that~~X, 2020. However, if the date of the ~~2017~~2021 annual meeting is advanced more than 30 days prior to, or delayed more than 30 days after, May ~~18, 2017, in order for a proposal by a shareholder to be timely,~~XX, 2021, such ~~proposal~~proposals must be delivered ~~not earlier than~~between the 150th day prior to the date of the ~~2017~~2021 annual meeting and ~~not later than 5:00 p.m., Eastern time, on~~ the later of ~~(1)~~(i) the 120th day prior to the date of the ~~2017~~2021 annual meeting or ~~(2)~~(ii) the tenth day following the date on which public announcement of the date of the ~~2017~~2021 annual meeting of shareholders is first made.

~~Householding~~

What is householding of ~~Proxy Materials~~

proxy materials?

The SEC has adopted rules that permit companies and intermediaries (such as banks and brokers) to satisfy the delivery requirements for proxy statements and annual reports with respect to two or more shareholders sharing the same address by delivering a single set of proxy ~~statement addressed~~materials to ~~those shareholders.~~that address. This process, which is commonly referred to as ~~“householding,”~~"householding," potentially means extra convenience for stockholders (less bulk mail) and cost savings for companies.

~~This year, a~~

A number of brokers with account holders who are our shareholders ~~will be “householding”~~intend to "household" our proxy materials. A single proxy statement will be delivered to multiple shareholders sharing an address unless contrary instructions have been received from the ~~impacted~~affected shareholders. Once you ~~have received~~receive notice ~~from~~that your broker ~~that they~~ will be ~~“householding”~~householding communications to your address, ~~“householding”~~householding will continue until you are notified otherwise or until you revoke your consent. If, at any time, you no longer wish to participate in ~~“householding”~~householding and would prefer to receive a separate proxy statement and annual report, please notify us by ~~(1) directing your written request to: iStar Inc., 1114 Avenue of the Americas, 39th Floor, New York, New York 10036, Attn: Investor Relations or (2)~~ contacting our Investor Relations department ~~at (212) 930‑9400.~~ at:



			(212) 930-9400				iStar Inc. Attention: Investor Relations 1114 Avenue of the Americas 39th Floor New York, NY 10036


72\|iStar Inc. 2020 Proxy Statement

Table of Contents

Shareholders who currently receive multiple copies of the proxy statement at their address and would like to request ~~“householding”~~householding of their communications should contact us as specified above.

Are there any other matters coming before the ~~2016~~2020 Annual Meeting?

~~Our management~~

Management does not intend to bring any other matters before the annual meeting and knows of no other matters that are likely to come before the meeting. In the event any other matters properly come before the annual meeting or any postponement of the meeting, the ~~persons~~individuals named in the accompanying proxy will vote the shares represented by ~~such~~your proxy in accordance with their discretion.

~~We urge~~

Additional Information

The Securities and Exchange Commission allows us to "incorporate by reference" information into this proxy statement. That means we can disclose important information to you by referring you to ~~authorize a~~another document filed separately with the SEC. The information incorporated by reference is considered to be part of this proxy statement, except to ~~vote your shares~~the extent the information is superseded by ~~completing, signing, dating and returning~~information in this proxy statement.

This proxy statement incorporates by reference: (a) the ~~accompanying proxy card~~information contained in ~~the accompanying postage‑paid return envelope at your earliest convenience, whether or not you presently plan to attend the meeting in person.~~

~~Availability of~~our Annual Report on Form ~~10‑K~~

~~Our 2015 Annual Report to Shareholders, including our audited financial statements~~10-K for the ~~fiscal~~ year ended December 31, ~~2015, is being made available to you along~~2019; and (b) the information contained in all other documents we file with the SEC after the date of this proxy statement and prior to the annual meeting of stockholders. The information contained in any of these documents will be considered part of this proxy statement from the date these documents are filed.

Any statement contained in this proxy statement or in a document incorporated or deemed to be incorporated by reference herein will be deemed to be modified or superseded for purposes of this proxy statement to the extent that a statement contained herein or in any other subsequently filed document which also is or is deemed to be incorporated by reference herein modifies or supersedes such statement. Any statement so modified or superseded will not be deemed, except as so modified or superseded, to constitute a part of this proxy statement.

You may obtain, without charge, a copy of ~~our 2015 10‑K Report, without exhibits, by writing to us at iStar Inc., 1114 Avenue~~any of the ~~Americas, 39th Floor,~~ documents incorporated by reference herein by:



			by writing to: iStar Inc. Attention: Investor Relations 1114 Avenue of the Americas 39th Floor New York, NY 10036				by visiting our website: www.istar.com


		By Order of the Board of Directors, Geoffrey M. Dugan General Counsel and Corporate Secretary

New York, ~~NY 10036, Attention: Investor Relations, or by visiting our website at~~ ~~www.istar.com~~. The 2015 10‑K Report is not part of the proxy solicitation materials, however, and the information found on, or accessible through, our website is not incorporated into, and does not form a part of, this proxy statement or any other report or document we file with or furnish to the SEC.

~~By Order of the Board of Directors~~

~~Geoffrey M. Dugan~~

~~General Counsel, Corporate and Secretary~~

New York NY
April 10, 2020

~~April 8, 2016~~


Information about the Annual Meeting of Shareholders · Additional Information		iStar Inc. 2020 Proxy Statement\|73

Table of Contents

Exhibit A—Non-GAAP Reconciliation

Adjusted Income

~~EXHIBIT A~~

~~Adjusted Income~~

In addition to net income (loss) prepared in conformity with generally accepted accounting principles in the United States of America ("GAAP"), we use ~~Adjusted Income,~~adjusted income, a non-GAAP financial measure, to measure our operating performance. Adjusted ~~Income represents~~income is used internally as a supplemental performance measure adjusting for certain non-cash GAAP measures to give management a view of income more directly derived from operating activities in the period in which they occur. Adjusted income is calculated as net income (loss) allocable to common shareholders, prior to the effect of depreciation and amortization, provision for (recovery of) loan losses, impairment of assets, ~~stock‑based~~stock-based compensation expense, ~~and~~the liquidation preference recorded as a premium above book value on the redemption of preferred stock, the imputed non-cash interest expense recognized for the conversion feature of our senior convertible notes, the non-cash portion of gain (loss) on early extinguishment of ~~debt.~~debt and is adjusted for the effect of gains or losses on charge-offs and dispositions on carrying value gross of loan loss reserves and impairments.


								For the Years Ended December 31,

	For the Years Ended December 31,							2019			2018
	2015			2014

	(in thousands)							(in thousands of dollars)
Adjusted Income

Net income (loss) allocable to common shareholders	$	(52,675	)	$	(33,722	)	$	291,547		$	(64,757	)

Add: Depreciation and amortization⁽¹⁾	72,132			76,287				58,925			68,056
Add/Less: Provision for (recovery of) loan losses	36,567			(1,714		)

Add: Provision for loan losses								6,482			16,937

Add: Impairment of assets⁽²⁾	18,509			34,634				13,419			163,765

Add: Stock-based compensation expense	12,013			13,314				30,436			17,563

Add: Loss on early extinguishment of debt, net	281			25,369				7,118			4,318
Less: HPU/Participating Security allocation	(2,850		)	(4,791		)
Adjusted Income allocable to common shareholders	$	83,977		$	109,377

Add: Non-cash interest expense on senior convertible notes								4,984			4,733

Less: Losses on charge-offs and dispositions⁽³⁾								(121,576	)		(67,506	)

Adjusted Income allocable to common shareholders⁽⁴⁾							$	291,335		$	143,109


~~(1)~~	(1) Depreciation and amortization also includes our proportionate share of ~~depreciation and amortization expense for equity method investments and excludes the portion of depreciation and amortization expense allocable to noncontrolling interests.~~


~~(2)~~	~~For the year ended December 31, 2015, impairment of assets includes impairments on cost and equity method investments.~~

~~Adjusted EBITDA~~

~~Adjusted EBITDA, a non-GAAP financial measure, represents net income (loss) plus the sum of interest expense, income taxes,~~ depreciation and amortization ~~provision~~expense for ~~(recovery of) loan losses, impairment~~equity method investments and excludes the portion of depreciation and amortization expense allocable to noncontrolling interests.

(2)

Impairment of assets ~~stock-based compensation expense~~also includes impairments on equity method investments.

(3)

Represents the impact of charge-offs and dispositions realized during the ~~non-cash portion~~period. These charge-offs and dispositions were on assets that were previously impaired for GAAP and reflected in net income but not in Adjusted Income.

(4)

Adjusted Income for the year ended December 31, 2018, as previously reported, included a $75.9 million add-back attributable to aggregate deferred gains on our retained interests in entities to which we sold or contributed properties prior to 2018 and a $3.3 million add-back for depreciation related to such properties. We recognized those gains in our GAAP retained earnings as of ~~gain (loss) on early extinguishment~~January 1, 2018 when we adopted a new accounting standard that mandated such recognition. We retrospectively modified our presentation of ~~debt.~~Adjusted Income for 2018, as shown in the table above, to reflect the effects of the dispositions in the periods in which they occurred.

For the Years Ended December 31,
2015 2014
(in thousands)
Adjusted EBITDA
Net income (loss) $ (6,157 ) $ 15,765
Add: Interest expense⁽¹⁾
229,297
228,395
Add: Income tax expense 7,639
3,912
Add: Depreciation and amortization⁽²⁾
73,862 79,042
EBITDA 304,641
327,114
Add/Less: Provision for (recovery of) loan losses 36,567 (1,714 )
Add: Impairment of assets⁽³⁾
18,509 34,634
Add: Stock-based compensation expense 12,013 13,314
Add: Loss on early extinguishment of debt, net 281 25,369
Adjusted EBITDA $ 372,011 $ 398,717


~~(1)~~ Exhibit A—Non GAAP Reconciliation · Adjusted Income	~~Interest expense also includes our proportionate share of interest for equity method investments.~~	iStar Inc. 2020 Proxy Statement\|A-1


~~(2)~~	~~Depreciation and amortization includes our proportionate share of depreciation and amortization expense for equity method investments.~~


~~(3)~~	~~For the year ended December 31, 2015, impairment of assets includes impairments on cost and equity method investments.~~

iStar Inc.
1114 Avenue of the Americas
39th Floor
New York, New York 10036
www.istar.com

MMMMMMMMMMMM MMMMMMMMMMMMMMM C123456789 000000000.000000 ext 000000000.000000 ext 000000000.000000 ext 000000000.000000 ext 000000000.000000 ext 000000000.000000 ext 000004 ENDORSEMENT_LINE______________ SACKPACK_____________ MR A SAMPLE DESIGNATION (IF ANY) ADD 1 ADD 2 ADD 3 ADD 4 ADD 5 ADD 6 Your vote matters – here’s how to vote! You may vote online or by phone instead of mailing this card. Online GIof ntoo welwewct.reonnviicsivoontrienpgo, rts.com/STAR delete QR code and control # or scan the QR code — login details are located in the shaded bar below. Phone Call toll free 1-800-652-VOTE (8683) within the USA, US territories and Canada Save paper, time and money! Sign up for electronic delivery at www.envisionreports.com/STAR Using a black ink pen, mark your votes with an X as shown in this example. Please do not write outside the designated areas. q IF VOTING BY MAIL, SIGN, DETACH AND RETURN THE BOTTOM PORTION IN THE ENCLOSED ENVELOPE. q + 1. Election of Directors: For Withhold For Withhold For Withhold 01 - Clifford De Souza 02 - Robin Josephs 03 - Richard Lieb 04 - Barry Ridings 05 - Anita Sands 06 - Jay Sugarman ForAgainst Abstain ForAgainst Abstain 2. Say on Pay – A non-binding advisory vote approving executive compensation 3. Ratification of the appointment of Deloitte & Touche LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2020 Please sign exactly as name(s) appears hereon. Joint owners should each sign. When signing as attorney, executor, administrator, corporate officer, trustee, guardian, or custodian, please give full title. Date (mm/dd/yyyy) — Please print date below. Signature 1 — Please keep signature within the box. Signature 2 — Please keep signature within the box. MMMMMMM C 1234567890 J N T 4 6 7 4 7 MR A SAMPLE (THIS AREA IS SET UP TO ACCOMMODATE 140 CHARACTERS) MR A SAMPLE AND MR A SAMPLE AND MR A SAMPLE AND MR A SAMPLE AND MR A SAMPLE AND MR A SAMPLE AND MR A SAMPLE AND MR A SAMPLE AND + 6 2 D V 4 036GMD MMMMMMMMM B Authorized Signatures — This section must be completed for your vote to be counted. — Date and Sign Below A Proposals — The Board of Directors recommends a vote FOR all the nominees listed and FOR Proposals 2 and 3. Annual Meeting Proxy Card1234 5678 9012 345

The 2020 Annual Meeting of Shareholders of iStar Inc. will be held on Thursday, May 21, 2020 at 9:00 a.m., Eastern time, virtually via the internet at www.meetingcenter.io/270691408. To access the virtual meeting, you must have the 15-digit number that is printed in the shaded bar located on the reverse side of this form. The password for this meeting is — SFI2020. Important notice regarding the Internet availability of proxy materials for the Annual Meeting of Shareholders. The material is available at: www.envisionreports.com/STAR q IF VOTING BY MAIL, SIGN, DETACH AND RETURN THE BOTTOM PORTION IN THE ENCLOSED ENVELOPE. q + Notice of 2020 Annual Meeting of Shareholders Proxy Solicited by Board of Directors for Annual Meeting of Shareholders – May 21, 2020 at 9:00 a.m. Eastern Time Jay Sugarman and Geoffrey M. Dugan, or any of them, each with the power of substitution, are hereby authorized to represent and vote the shares of the undersigned, with all the powers which the undersigned would possess if personally present, at the Annual Meeting of Shareholders of iStar Inc. to be held on May 21, 2020 or at any postponement or adjournment thereof. Shares represented by this proxy will be voted as directed by the shareholder. If no such directions are indicated, the Proxies will have authority to vote FOR Item 1, the election of six nominees as directors, FOR Item 2, approval of the non-binding advisory vote approving executive compensation, and FOR Item 3 the ratification of the appointment of Deloitte & Touche LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2020. In their discretion, the Proxies are authorized to vote upon such other business as may properly come before the meeting. (Items to be voted appear on reverse side.) Change of Address — Please print new address below. Comments — Please print your comments below. Meeting Attendance Mark box to the right if you plan to attend the Annual Meeting. + C Non-Voting Items Proxy — iStar Inc. Small steps make an impact. Help the environment by consenting to receive electronic delivery, sign up at www.envisionreports.com/STAR



~~iSTAR INC.~~Filed by the Registrantý
Filed by a Party other than the Registranto
Check the appropriate box:
o		Preliminary Proxy Statement
o		Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))
ý		Definitive Proxy Statement
o		Definitive Additional Materials
o		Soliciting Material under §240.14a-12

2020		A virtual meeting via the internet at www.meetingcenter.io/ 270691A08.
~~Proposal 3:~~	~~Non-binding, Advisory Vote~~

In addition, we will transact such other business as may properly come before the annual meeting or any postponement or adjournment of the meeting.			Shareholders of record at the close of business on ~~a “Say on Pay” Resolution~~March 20, 2020 are entitled to ~~Approve Executive Compensation~~notice of and to vote

Agenda Item			More Information


Proposal 1	Elect six directors nominated by iStar's Board	FOR each Nominee	Page 7

Proposal 2	Approve, on an advisory basis, executive compensation	FOR	Page 30

Proposal 3	Ratify the selection of the independent auditors	FOR	Page 61


Proxy Season (March—May)		Off-Season (September—February)

O Every year we reach out to our largest institutional shareholders and engage directly with all who respond affirmatively, both in person and by teleconference O Any feedback from these discussions is shared with the full Board and management team ahead of the Annual Meeting		O Each year, members of our management team and the Board engage with shareholders to discuss strategy, performance, executive compensation, Board composition and other ESG topics O Feedback from these discussions is shared with the full Board and management team and ultimately informs the Board's decision-making process



~~Name~~	~~Age~~	~~Title~~
~~Jay Sugarman~~	53	~~Chairman~~ Director Nominations and ~~Chief Executive Officer~~
~~Clifford De Souza~~Qualifications⁽¹⁾	54	~~Independent Director~~
~~Robert W. Holman, Jr.~~⁽²⁾⁽³⁾	72	~~Independent Director~~
~~Robin Josephs~~⁽²⁾⁽³⁾	56	~~Lead Independent Director~~
~~John G. McDonald~~⁽²⁾⁽³⁾	78	~~Independent Director~~
~~Dale Anne Reiss~~⁽¹⁾	68	~~Independent Director~~
~~Barry W. Ridings~~⁽¹⁾⁽²⁾	64	~~Independent Director~~


iStar Inc.
(Name of Registrant as Specified In Its Charter)

(Name of ~~Registrant as Specified In Its Charter)~~




Payment of Filing Fee (Check the appropriate box):
ý		No fee required.
o		Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11.
		(1)	Title of each class of securities to which transaction applies:
		(2)
	~~(2)~~	Aggregate number of securities to which transaction applies:
		(3)
	~~(3)~~	Per unit price or other underlying value of transaction computed pursuant to Exchange Act Rule 0-11 (set forth the amount on which the filing fee is calculated and state how it was determined):
		(4)
	~~(4)~~	Proposed maximum aggregate value of transaction:
		(5)
	~~(5)~~	Total fee paid:
o


¨ o		Check box if any part of the fee is offset as provided by Exchange Act Rule 0-11(a)(2) and identify the filing for which the offsetting fee was paid previously. Identify the previous filing by registration statement number, or the Form or Schedule and the date of its filing.



(1)	~~(1)~~	Amount Previously Paid:
		(2)
	~~(2)~~	Form, Schedule or Registration Statement No.:
		(3)	Filing Party:
		(4)	Date Filed:


A Letter from iStar's Lead Independent Director		iStar Inc. 2020 Proxy Statement



Proposal 1		Election of six directors	Thursday, May 21, 2020 9:00 a.m. Eastern time

Proposal 2		Non-binding, advisory vote to approve executive compensation ("Say-on-Pay")
	~~(3)~~	~~Filing Party:~~
Proposal 3
	~~(4)~~	~~Date Filed:~~

	~~(5)~~	~~Total fee paid:~~


~~Proposal 1.~~	~~Election of Directors: Jay Sugarman, Clifford De Souza, Robert W. Holman, Jr., Robin Josephs, John G. McDonald, Dale Anne Reiss, and Barry W. Ridings.~~


~~Proposal 2:~~	Ratification of the ~~Appointment~~appointment of ~~PricewaterhouseCoopers~~Deloitte & Touche LLP as our ~~Independent Registered Public Accounting Firm~~independent registered public accounting firm for the fiscal year ending December 31, ~~2016.~~



Even if you expect to participate in the annual meeting, please vote your proxy in advance to ensure that your shares will be counted.	IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING OF SHAREHOLDERS TO BE HELD ON MAY 21, 2020 We make proxy materials available to our shareholders online. You can access proxy materials including our 2019 annual report to shareholders athttp://www.envisionreports.com/STAR. You also may request a paper or an e-mail copy of our proxy materials and a paper proxy card by following the instructions included in the Notice of Internet Availability of Proxy Materials.	By Order of the Board of Directors, Geoffrey M. Dugan General Counsel, Corporate and Secretary New York, New York April 9, 2020


Notice of 2020 Annual Meeting of Shareholders		iStar Inc. 2020 Proxy Statement


Proxy Summary		1

Proposal 1—Election of Directors		7

Candidates for Election as Director		9

Corporate Governance		15

Board Leadership Structure		15

Board Composition and Diversity		16

Director Independence		16

Nominations for the Board		17

Board's Role in Risk Oversight		18

Board and Committee Annual Assessments		18

Board Meetings Held during 2018		19

Executive Sessions		19

Service on Other Boards		19

Director Resignation Policy		19

Defensive Measures Profile		20

"Whistleblower Policy"		20

Governing Documents		20

Disclosure Committee		21

Communications with the Board		22

Board Committees		23

Audit Committee		24

Compensation Committee		25

Nominating and Governance Committee		26

Investment Committee		26

Director Compensation		27

Indemnification		29


Proposal 2—Advisory Vote to Approve Executive Compensation		30

Letter from the Chairman of the Compensation Committee		31

Compensation Discussion and Analysis Contents		33

Compensation Discussion and Analysis		34

Summary		34

Business Highlights and Performance		41

Detailed Program Discussion		43

Compensation Committee Report		53

Chief Executive Officer Pay Ratio		54

Executive Compensation Tables		55

Proposal 3—Ratification of the Appointment of Independent Registered Accounting Firm		61

Accounting Fees and Services		61

Report of the Audit Committee		63

Stock Ownership Information		65

Security Ownership of Certain Beneficial Owners and Managers		65

Section 16(a) Beneficial Ownership Reporting Compliance		66

Certain Relationship and Related Party Transactions		67

Information about the Annual Meeting of Shareholders		69

Exhibit A—Non-GAAP Reconciliation		A-1


Proxy Summary · Overview of Our Business		iStar Inc. 2020 Proxy Statement\|1


Proxy Summary · Current Board and Nominees		iStar Inc. 2020 Proxy Statement\|3



	< Threshold	Threshold	Target	High
TSR Percentile Achieved	Less than 30th Percentile	30th Percentile	50th Percentile	75th Percentile
Shares Earned (as % of Target amount)	0%	50%	100%	200%


~~(7)~~	~~These time-based Units will cliff vest in one installment on December 31, 2017 if the officer is employed by us on the vesting date. See discussion in "Compensation Discussion and Analysis~~ ~~-Time-Based Awards".~~


~~(8)~~	~~These annual incentive awards are issued fully-vested and the executive officers identified in this proxy statement are restricted from selling these shares for up to two years from the date of grant.~~



	Stock Awards
Name	Number of Shares or Units of Stock That Have Not Vested (#)		Market Value of Shares or Units of Stock That Have Not Vested ($)⁽¹⁾		Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested (#)		Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested ($)
Jay Sugarman	21,714	⁽²⁾	$	254,705
						⁽³⁾	$	12,536,000	⁽³⁾
David DiStaso	9,000	⁽²⁾	105,570
	4,409	⁽⁴⁾	51,718		20,578	⁽⁵⁾	241,380		⁽⁵⁾
	3,451	⁽⁶⁾	40,480		16,104	⁽⁷⁾	188,900		⁽⁷⁾
						⁽³⁾	688,000		⁽³⁾
Nina Matis	27,000	⁽²⁾	316,710
						⁽³⁾	2,765,000		⁽³⁾


~~(1)~~	~~The market value of unvested Units is calculated by multiplying the number of Units by $11.73, the closing market price of our common stock on December 31, 2015.~~


~~(4)~~ Executive Compensation Tables · Grants of Plan-Based Awards		~~See "~~iStar Inc.~~Compensation Discussion and Analysis~~ 2020 Proxy Statement~~-Time-Based Awards" for a discussion of these time-based Units that will cliff vest in one installment on December 31, 2016 if the officer is employed by us on that date.~~\|57


~~(6)~~ 58\|iStar Inc. 2020 Proxy Statement		~~See "Compensation Discussion and Analysis-Time-Based Awards" for a discussion of these time-based Units that will cliff vest in one installment on December 31, 2017 if the officer is employed by us on that date.~~



	Stock Awards
Name	Number of Shares Acquired on Vesting (#)⁽¹⁾	Value Realized on Vesting ($)
Jay Sugarman	—	$	—
David DiStaso	22,195	284,823
Nina Matis	56,557	737,503



Name	Market Value of Earned Units Upon Termination Without Cause ($)⁽¹⁾		Vesting/Delivery Date
Jay Sugarman	$	247,632	2/1/16
David DiStaso	102,635		2/1/16
	34,478		12/31/16
	13,493		12/31/17
Nina Matis	307,913		2/1/16



Name	Fees Earned or Paid in Cash ($)		Stock Awards ($)⁽¹⁾		All Other Compensation ($)⁽²⁾		Total ($)
Clifford De Souza	$	56,250	$	98,096	$	—	$	154,346
Robert W. Holman, Jr.	158,750		129,499		5,000		293,249
Robin Josephs	131,000		207,187		5,000		343,187
John G. McDonald	130,000		129,499		5,000		264,499
Dale Anne Reiss	145,000		129,499		5,000		279,499
Barry W. Ridings	138,000		129,499		5,000		272,499