UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

(Rule14a-101)

INFORMATION REQUIRED IN PROXY STATEMENT

SCHEDULE 14A INFORMATION

Proxy Statement Pursuant to Section 14(a) of the Securities

Exchange Act of 1934 (Amendment No.              )

Filed by the Registrantþ ☑

Filed by a Party other than the Registrant¨ ☐

Check the appropriate box:

ALLEGHANY CORPORATION

(Name of Registrant as Specified In Its Charter)

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

Payment of Filing Fee (Check the appropriate box):

Alleghany Corporation (“Alleghany”) hereby gives notice that its 20162019 Annual Meeting of Stockholders (the “2016“2019 Annual Meeting”) will be held at The Penn Club, of New York, 30 West 44^th Street, New York, New York, on Friday, April 22, 201626, 2019 at 10:00 a.m., local time, for the following purposes:

Holders of Alleghany common stock at the close of business on March 1, 20162019 are entitled to receive this Notice and vote for the election of directors and on each of the other matters set forth above at the 20162019 Annual Meeting and any adjournments or postponements thereof.

You are cordially invited to attend the 20162019 Annual Meeting. Representation of your shares at the 20162019 Annual Meeting is very important. Whether or not you plan to attend in person, we encourage you to vote your shares promptly by using the Internet or telephone, or by signing and returning the enclosed proxy card in the envelope provided. You may revoke your proxy at any time before it is voted at the 20162019 Annual Meeting by written notice to the Secretary of Alleghany, by submitting a new proxy with a later date, or by voting in person at the 20162019 Annual Meeting.

Important Notice Regarding Internet Availability of Proxy Materials for the Alleghany Corporation 20162019 Annual Meeting of Stockholders to be Held on April 22, 2016:26, 2019: Proxy materials relating to the 20162019 Annual Meeting (notice of meeting, proxy statement, proxy and 20152018 Annual Report to Stockholders onForm 10-K) are also available on the Internet at www.envisionreports.com/www.edocumentview.com/YAL.

Dear Alleghany Stockholder:

Thank you for your continued ownership and support of Alleghany Corporation. On behalf of Alleghany’s Board of Directors, it is my pleasure to invite you to join us at the upcoming Annual Meeting of Stockholders. If you are unable to make the Annual Meeting, I encourage you to cast your vote on the items discussed in the Proxy Statement using the attached proxy card or by voting via telephone or online as detailed in the Proxy Statement.

In 2019, Alleghany Corporation marks the 90th anniversary of its founding. The values that were instilled in this company by earlier generations continue to drive our success today. We believe that our culture is a competitive advantage and a key differentiator when recruiting, attracting acquisition candidates, and growing our business.

Our Board of Directors is comprised of a group of committed and highly qualified individuals who care deeply about our company and bring a diverse set of experiences and perspectives to our Board deliberations. Our directors’ skills and independent thought leadership have been invaluable to me and the management team in establishing our long-term business strategy and executing on that strategy. Appearing for the first time as a director candidate in the Proxy Statement is Lauren Tyler, who was appointed to the Board in January of this year. We are pleased that Lauren has joined the Board, bringing strategic, operational, and leadership capabilities which are only partly covered in the Proxy Statement. We encourage you to vote for her and the other directors on the ballot, as well as the other proposals, at the upcoming Annual Meeting.

As we think about the past year and where we will take the company into the future, we remain committed to ensuring that pay is aligned with performance and the interests of our long-term stockholders. The Compensation Committee letter to stockholders on pages 39 and 40 provides more detailed perspective on this front. The Alleghany Board and management team are focused on creating long-term value for our stockholders, and our governance, strategy and management compensation are designed with this focus in mind.

On behalf of Alleghany’s Board and management, we look forward to seeing you at the upcoming 2019 Annual Meeting of Stockholders. The attached Notice of Annual Meeting of Stockholders and Proxy Statement will serve as your guide to the business to be conducted at the meeting this year. Please participate in Alleghany’s future by casting your vote on the items discussed in the Proxy Statement whether in person or through the other voting options that are described.

Sincerely,

Jefferson W. Kirby

Chairman of the Board

PROXY STATEMENT SUMMARY

This summary highlights selected information that is discussed in more detail elsewhere in this Proxy Statement. This summary does not contain all of the information you should consider, and you should read the full Proxy Statement before voting. Unless the context otherwise requires, references in this Proxy Statement to “Alleghany,” the “Company,” “we,” “our” or “us” refer to Alleghany Corporation, references to the “Board” refer to our Board of Directors, references to the “common stock” refer to our common stock, par value $1.00 per share, and references to the “2016“2019 Annual Meeting” refer to our 20162019 Annual Meeting of Stockholders and any and all adjournments or postponements thereof.

20162019 ANNUAL MEETING INFORMATION

MEETING AGENDA AND BOARD RECOMMENDATIONS

HOW TO VOTE (pages 8 and 9)9 - 11)

You can vote by any of the following methods:

If you vote byusing the Internet or telephone, you must vote no later than 1:00 a.m., Eastern Daylight Time, on April 22, 2016.

BOARD NOMINEES (page 26)28)

Karen Brenner Age 63 Director since 2009 Chair of the Nominating and     Governance Committee Member of the Audit Committee				Ms. Brenner has been an Executive Director of Law and Business Initiatives at New York University since 2012 and Clinical Professor of Business at the Leonard N. Stern School of Business at New York University since 2008. She teaches professional responsibility in law and business, corporate governance in law and business, and corporate transformation and leadership. Ms. Brenner’s qualifications to serve on the Board also include her years of business experience as Chairman/Chief Executive Officer and/or a board member of public and private companies in a wide variety of industries, and as an advisor to private equity firms, venture capital companies, boards of directors and chief executive officers focusing on enhancing the value of operating companies.
John G. Foos Age 69 Director since 2012 Member of the Audit     Committee Member of the Nominating     and Governance Committee						Mr. Foos was Chief Financial Officer of Independence Blue Cross, a health insurance company, from 1989 until his retirement in November 2008. In addition, Mr. Foos currently serves as a director of Blue Cross Blue Shield of South Carolina, a South Carolina-owned and operated health insurance carrier, the HAI Group Companies, a provider of niche insurance programs and services for the public and affordable housing community, and Emerald Shelter Group, anot-for-profit that provides healthcare and affordable housing. Mr. Foos was a director of Transatlantic Holdings, Inc., or “TransRe,” prior to March 6, 2012. Mr. Foos’s qualifications to serve on the Board also include his extensive experience in and knowledge of accounting and finance, which includes service as the Chief Financial Officer of Independence Blue Cross, in addition to his prior experience as a Partner with KPMG LLP and his financial literacy.
Lauren M. Tyler Age 57 Director since 2019				Ms. Tyler has been Head of Human Resources at J.P. Morgan Chase & Co., Asset & Wealth Management, or “J.P. Morgan,” overseeing all aspects of human resources, since 2015. Prior to that, Ms. Tyler was Global Chief Auditor for J.P. Morgan from 2012 to 2015 and Head of Investor Relations from 2009 to 2012. Ms. Tyler’s qualifications to serve on the Board also include her over 30 years of business experience in banking, finance, and accounting, her experience in private equity and service as a Board member of private companies, and her financial expertise.

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GOVERNANCE HIGHLIGHTSSUMMARY

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PERFORMANCE HIGHLIGHTSSUMMARY

2015A summary of 2018 and long-term financial results highlights are as follows:

2015Alleghany Performance in 2018

Additional information regarding Alleghany’s 20152018 results, including audited consolidated financial statements, as well as Management’s Discussion and Analysis of Financial Condition and Results of Operations, or “MD&A,” with respect to 20152018 results, is contained in Alleghany’s Annual Report on Form10-K for the year endedyear-ended December 31, 2015,2018, or the “Form10-K,” which was filed with the U.S. Securities and Exchange Commission, or the “SEC,” on February 23, 2016.20, 2019. Readers are urged to review the Form10-K for a more complete discussion of Alleghany’s financial performance.

Alleghany Long-Term Performance

We believe that Alleghany’s performance is best measured over the long term, and that long-term growth in common stockholders’ equity per share is the best metric for evaluating such performance. In this regard, the table below shows the annual, and three- andten-year average rolling, annualized growth in our common stockholders’ equity per share, adjusted for a 2018 cash dividend and historical stock dividends, during the five-year period from December 31, 20102013 to December 31, 2015:2018:

As can be seen in the table above, Alleghany’s common stockholders’ equity per share has compounded over the various time metricsthree- andten-year periods in the mid-rangerange of Alleghany’s stated financialstrategic objective of7-10% annual growth in common stockholders’ equity per share.share, although it trailed that objective in 2018 and the three-year periods ending in 2017 and 2018 primarily due to a decline in the market value of Alleghany’s equity portfolio in December 2018 and significant catastrophe losses in 2017 and 2018.

The chart below summarizes Alleghany’s common stockholders’ equity per share growth and stock price performance over theten-year period from December 31, 20052008 to December 31, 2015,2018, compared with the Standard & Poor’sS&P 500 Stock Index, or the “S&P 500,” with all values indexed to December 31, 2005.2008. During thisten-year period, Alleghany’s common stockholders’ equity per share increased at a compound annual rate of 8.6%7.2% (adjusted for dividends), compared with a compound annual rate of return of 7.3%13.1% for the S&P 500, and the price of Alleghany common stock (adjusted for stock dividends) appreciated at a 6.6%9.1% compound annual rate of return.

As indicated by the data presented in the chart above, Alleghany’s growth in common stockholders’ equity per share has been relatively consistent.consistent, with the exception of 2018 when it was negatively impacted by a decline in the market value of Alleghany’s equity portfolio and significant catastrophe losses. The trading price of Alleghany’s common stock has been more volatile, reflecting the volatility of the stock market in general. In Alleghany’s view, growth in common stockholders’ equity per share is a better measure of fundamental performance and value creation as compared to the more volatile trading price of Alleghany’s common stock. As such, Alleghany focuses its executive compensation incentive program on building common stockholders’ equity per share over time. As is shown in the chart, Alleghany’s growth in common stockholders’ equity per share has exceeded that of the S&P 500 return over the past ten years and is considerably less volatile.

COMPENSATION HIGHLIGHTS

Compensation PhilosophySUMMARY

Our executive compensation program is intended to provide competitive total compensation to each of Alleghany’s executive officers (as listed on page 21)23), or the “Named Executive Officers,” that is aligned with the interests of our stockholders in increasing our common stockholders’ equity per share at rates of7-10% over the long term without employing excessive amounts of financial leverage and without taking imprudent risks. This approach enables us to manage risk to avoid loss of capital during periods of economic turmoil, which we believe creates maximum value for stockholders in the long term, even if it results in lower levels of capital appreciation during periods when economic conditions are more favorable.

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2018 Named Executive Officer Compensation

Set forth below is the 2018 compensation for each Named Executive Officer as determined under SEC rules. See the 2018 Summary Compensation Table and the accompanying notes to the table beginning on page 59 for more information.

Name and Principal Position		Salary				Bonus				Stock Awards				Non-Equity Incentive Plan Compensation				Change in Pension Value and Nonqualified Deferred Compensation Earnings				All Other Compensation				Total
Weston M. Hicks		$	1,030,000			$	—			$	4,767,823			$	2,163,000			$	—			$	168,529			$	8,129,352
President and chief executive officer
Joseph P. Brandon			875,000				—				2,828,591				1,750,000				—				140,858				5,594,449
Executive Vice President
Christopher K. Dalrymple			690,000				—				1,114,654				690,000				—				109,719				2,604,373
Senior Vice President, General Counsel and Secretary
John L. Sennott, Jr.			690,000				—				1,114,654				690,000				—				110,224				2,604,878
Senior Vice President and chief financial officer

Elements of 2018 Compensation

The principal elements of compensation paid to our Named Executive Officers and the percentage that these elements represent of the 2018 compensation for our chief executive officer and our other Named Executive Officers are reflected below.

 

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For 2015, this compensation philosophy was evidenced by the following compensation highlights:With respect to such components of 2018 compensation:

 

CEO total direct compensation (salary, annual cash incentive and long-term equity basedequity-based awards) was $6.7approximately $8.0 million, representing approximately 0.9%0.2% of 2015 pre-tax earnings and approximately 0.1% of 20152018 revenues, and total direct compensation for our Named Executive Officers as a group was $17.1approximately $18.4 million, representing approximately 2.4% of 2015 pre-tax earnings and approximately 0.4% of 20152018 revenues.

 

85%87.1% of Mr. Hicks’s 2018 total direct compensation for 2015 was linked to performance, while performance-linked compensation for our other Named Executive Officers averaged 74%78.4% of total direct compensation in 2015.2018.

 

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Elements of 2015 Compensation

The principal elements of compensation paid to our Named Executive Officers in respect of 2015 consisted of:

In addition, our Named Executive Officers receive a benefit, assuming the completion of five years of service with Alleghany or a subsidiary of Alleghany, under a retirement plan, although such benefit was frozen in 2013.

The percentage that these elements represent of the 2015 compensation for our chief executive officer and our other Named Executive Officers is reflected below.

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2015 Named Executive Officer Compensation

The following table sets forth the compensation of our Named Executive Officers during 2015, as calculated in accordance with applicable SEC regulations. For a complete schedule and related footnotes, please see the “Summary Compensation Table” on page 54 in the Executive Compensation section of this Proxy Statement.

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QUESTIONS AND ANSWERS ABOUT ALLEGHANY’S 20162019 ANNUAL MEETING

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If you properly sign and return your proxy card or submit your proxy using the Internet or telephone, your shares will be voted as you direct. If you sign and return your proxy card but do not specify how to vote, we will vote your shares in accordance with the Board’s recommendations: “FOR” each of the Board’s nominees for director; “FOR” the ratification of the selection of our independent registered public accounting firm; and “FOR” the advisory resolution on executive compensation.

The 20162019 Annual Meeting will begin promptly on April 22, 2016,26, 2019, at 10:00 a.m., local time. You should allow adequate time forcheck-in procedures.

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A “brokernon-vote” occurs when your broker submits a proxy for your shares but does not indicate a vote for a particular proposal because the broker does not have authority to vote on that proposal and has not received voting instructions from you. “Brokernon-votes” are counted as present to determine whether there is a quorum for the 20162019 Annual Meeting, but are not counted as votes for or against the proposal in question or as abstentions, nor are they counted to determine the number of votes present for the particular proposal.

Proposal 2: Ratification of Selection of Independent Registered Public Accounting Firm. The affirmative vote of a majority of the votes cast on this proposal is required to ratify the selection of our independent registered public accounting firm. Abstentions and broker non-votes will have no effect on the results of this vote. The approval of Proposal 2 is a routine proposal on which a broker or other nominee is generally empowered to vote in the absence of voting instructions from the beneficial owner, so brokernon-votes are unlikely to result from this proposal.

Proposal 3: Advisory Vote on Executive Compensation. The affirmative vote of a majority of the votes cast on this proposal is required to approve the advisory resolution on executive compensation. Abstentions and brokernon-votes will have no effect on the results of this vote. Although this proposal isnon-binding on the Board, the Board and the Compensation Committee will review and consider the voting results when making future decisions about Alleghany’s executive compensation program.

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If, in the future, you wish to receive a separate annual report to stockholders and proxy statement, a separate copy may be obtained, without charge, upon written or oral request to the office of the Secretary, Alleghany Corporation, 7 Times Square Tower,1411 Broadway, 34^th Floor, New York, New York 10036,10018, telephone number(212) 752-1356. Eligible stockholders of record who receive multiple copies of our annual report to stockholders and proxy statement can request householding by contacting us in the same manner. Stockholders who own shares through a bank, broker or other nominee can request householding by contacting the nominee. We hereby undertake to deliver promptly, upon written or oral request, a separate copy of the annual report to stockholders and proxy statement to a stockholder at a shared address to which a single copy of the document was delivered.

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CORPORATE GOVERNANCE

Board of DirectorsComposition

Pursuant to Alleghany’s Restated Certificate of Incorporation andBy-Laws, the Board is divided into three separate classes of directors, which are required to be as nearly equal in number as practicable. At each Annual Meeting of Stockholders, one class of directors is elected to a term of three years. Currently, there are three standing committees of the Board, consisting of annamely the Audit Committee, Compensation Committee and Nominating and Governance Committee. Additional information regarding these committees is set out on pages 13 through 15.16 to 18.

The Board currently consists of tennine directors. Mr. Stephen P. Bradley, who has served asAt a director of Alleghany since 2012, and Mr. Thomas S. Johnson, who has served as a director of Alleghany since 1997 and for 1992-1993, are retiring from the Board effective at the 2016 Annual Meeting in accordance with Alleghany’s director retirement policy as described on page 17. In this regard, because Mr. Bradley and Mr. Johnson are not standing for re-election, in order to make the classesmeeting of the Board as nearly equal in size as practicable,on January 15, 2019, the Board determinedincreased its size from eight to nominate Mr. John G. Foos, whonine directors and elected Lauren M. Tyler to fill the vacancy created by such increase in size. Ms. Tyler was last elected for a term due to the Boardexpire at the 2015 Annual Meeting of Stockholders, to stand for re-election at the 20162019 Annual Meeting. As a result, theThe directors nominated by the Board for election at the 20162019 Annual Meeting to the class of 20192022 are Ms.Karen Brenner, John G. Foos and Mr. Foos. If bothLauren M. Tyler. Each of Ms. Brenner and Mr. Foos are elected, the sizenominees is a current member of the Board will be reduced effectiveand was recommended to the Board for nomination by the Nominating and Governance Committee. Mr. Foos and Ms. Brenner were last elected by stockholders at the 2016 Annual Meeting fromof Stockholders held on April 22, 2016.

As stated in our Corporate Governance Guidelines, the Board “currently believes that it is desirable over time to have a Board of between eight and ten members (allowing that a larger or smaller number may be necessary or advisable in periods of transition or other particular circumstances).” In March 2012, upon the closing of Alleghany’s acquisition of Transatlantic Holdings, Inc., or “TransRe,” three former members of the board of directors of TransRe joined the Alleghany Board, resulting in a14-person Board. Through 2018, Alleghany intentionally allowed the Board to eight directors.decrease in size through the mandatory and elective retirements of six Board members, resulting in an eight-member Board at 2018year-end.

We have strong director engagement on our Board. Cognizant of upcoming mandatory retirements, the Board in 2018 evaluated potential new Board members, as well as the characteristics desired in such potential Board members. In this regard, the Board sought candidates with diverse business and professional backgrounds and outstanding integrity and judgment, and such other skills and experience as would enhance the Board’s ability to best serve Alleghany’s interests. In addition, the Board specifically considered diversity as one of many factors in its evaluation. As discussed above, the Board’s evaluation culminated in the appointment of Ms. Tyler to the Board in January 2019, and she is standing for election at the 2019 Annual Meeting.

The Board held eight meetings in 2015. Eachfollowing charts illustrate the characteristics of our incumbent directors, attended at least 96 percent of the meetings of the Boardincluding independence, diversity, age and committees of the Board on which he or she served in 2015, with nine of our current ten directors attending 100 percent of the Board and committee meetings. Executive sessions for independent directors are held at each regularly scheduled Board meeting. The Chairman of the Board, or the “Chairman,” who is currently an independent director, presides at these executive sessions. Alleghany does not have a policy with regard to attendance by directors at Annual Meetings of Stockholders. Two directors attended the 2015 Annual Meeting of Stockholders.tenure.

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Director Independence

Pursuant to the NYSE’s listing standards, Alleghany is required to have a majority of independent directors, and no director qualifies as independent unless the Board affirmatively determines that the director has no material relationship with Alleghany. The Board has determined that none of ourthe directors who served during any part of 2018, except Weston M. Hicks, our President and chief executive officer, has any material relationship with Alleghany other than in their capacities as members of the Board and committees thereof, and thus all of such directors, except Weston M. Hicks, are independent directors of Alleghany. Therefore, nineWith the January 2019 election of Lauren M. Tyler, whom the Board affirmatively determined has no material relationship with Alleghany, eight of Alleghany’s tennine current directors are independent directors. BothAll of the director nominees are independent. Assuming that all of Ms. Brenner, and Mr. Foos are independent. Following the retirement of Mr. Bradley and Mr. Johnson at the 2016 Annual Meeting, and assuming that both Ms. Brenner and Mr. FoosTyler are elected, eight of nine directors will be independent.

Board Leadership

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

Board Meetings

We have strong director engagement on our Board. The Board held eight meetings in 2018. Each director who was a director during 2018 attended at least 95% of the meetings of the Board and committees of the Board on which he or she served in 2018, with seven of such directors attending 100% of the Board and committee meetings. Executive sessions for independent directors are held at each regularly scheduled Board meeting. The Chairman, who is currently an independent director, presides at these executive sessions. Alleghany does not have a policy with regard to attendance by directors at annual meetings of stockholders. Two directors attended the 2018 Annual Meeting of Stockholders.

Board Evaluation

The Board believes that an effective director evaluation process allows it to gain insights into the effectiveness of the Board, its committees and its individual members, with the goal of continually enhancing Board performance. In this regard, each year the Board and each of its committees conducts an evaluation of their respective performance, effectiveness and fulfillment of fiduciary duties. The evaluation process is overseen by the Nominating and Governance Committee and is reviewed annually to determine whether it is designed effectively and assures that appropriate feedback is being sought and reviewed. Historically, the Board evaluation was done on an overall basis through completion of a written questionnaire by each director on an anonymous basis to encourage candid feedback, supplemented by individual director interviews with the Chairman.

In 2018, the Board determined to enhance the evaluation process by adding an individual director evaluation component, along with the completion of a director skills matrix. In this regard, the Nominating and Governance Committee approved evaluation questions which were to be considered by each director with respect to himself or herself, as well as each other director, along with a skills matrix questionnaire to be completed by each director. The Chairman of the Board, using the evaluation questions as a guide, then solicited a self-evaluation from each director, as well as an evaluation of each other director. The Chair of the Nominating and Governance Committee solicited from each director an evaluation of the Chairman of the Board. At the conclusion of such process, the Chairman of the Board discussed with each director the results of his or her individual evaluation,

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and the Chair of the Nominating and Governance Committee discussed such matters with the Chairman of the Board. The results of the written overall Board and committee evaluations were reported to and reviewed by the full Board. In general, based upon its most recent evaluation, the Board and each committee were satisfied with their respective performance and considered themselves to be operating effectively.

Chief Executive Officer and Senior Management Succession Planning

A key responsibility of our chief executive officer and Board in the area of risk management is ensuring that an effective process is in place to provide continuity of leadership over the long term. At least once each year, our Board conducts a review of chief executive officer and senior management succession planning. During this review, the chief executive officer provides the Board with recommendations on, and evaluations of, potential chief executive officer and senior management successors, succession timing for those positions, and development plans for the potential successors. Our Board reviews potential internal senior management candidates with our chief executive officer, including the qualifications, experience and development priorities for these individuals. Further, our Board periodically reviews the overall composition of our senior management’s qualifications, tenure and experience.

Our Board, in coordination with our Nominating and Governance Committee, also establishes steps to address emergency chief executive officer and senior management succession planning in extraordinary circumstances. Our emergency chief executive officer succession planning is intended to enable us to respond to unexpected position vacancies, including those resulting from a major catastrophe, by continuing our operations and minimizing potential disruption or loss of continuity to our business and operations.

Board Role in Risk Oversight

The Board oversees risk management directly and through its committees. Alleghany management regularly reports to the Board and, as appropriate, to its committees on management’s risk activities, Alleghany’s exposure and risk assessments. Enterprise risk management is a standing agenda item at each Board meeting and the chief risk officer, other Alleghany management and the Board discuss existing and emerging risks, controls and procedures, risk assessments and initiatives at such meetings. Each year, at the 2016 Annual MeetingBoard’s January meeting, the Board receives a formal report on enterprise risk management from tenAlleghany’s chief risk officer and, at the same meeting, considers Alleghany’s three-year financial projections and the evaluation of the President and chief executive officer, allowing the Board to eight directors, sevenconsider risk and risk management in the context of whom will be independent.Alleghany’s strategic plan and management’s performance. Each year, at the Audit Committee’s June meeting, it receives a formal report on enterprise risk management from Alleghany’s chief risk officer and a formal report on legal compliance and ethics from Alleghany’s chief compliance officer, which are also copied to the Board, and the chief risk officer and chief compliance officer subsequently report thereon to the Board. The Board receives updates on material developments with respect to risk management and legal compliance and ethics matters at its other regularly scheduled meetings.

The Audit Committee oversees the integrity of Alleghany’s financial statements, compliance with legal and regulatory requirements, the qualifications, performance and independence of independent auditors and the performance of internal audit and internal controls over financial reporting, all of which contribute to risk oversight. The Nominating and Governance Committee ensures the development of appropriate corporate governance and oversees the evaluation of the Board and management. The Compensation Committee regularly monitors compensation policies, practices and outstanding awards to determine whether Alleghany’s risk management and incentive objectives are being met with respect to group-wide employee incentives. The Board believes that risk oversight is a responsibility of the entire Board, and it does not look to any individual director or committee to lead it in discharging this responsibility.

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Committees of the Board of Directors

Committee Membership

The following table sets forth the current members of each of the committees and the number of meetings held during 2015:2018:

The Board has determined that each committee member is independent as defined in the NYSE’s listing standards with respect to membership on each committee on which he or she serves. The Board also has determined that each member of the Audit Committee has the qualifications set forth in the NYSE’s listing standards regarding financial literacy and accounting or related financial management expertise and is an audit committee financial expert as defined by the SEC.

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Committee Responsibilities

Each of the committees listed below operates pursuant to a charter, a copy of which is available on Alleghany’s website at www.alleghany.com or may be obtained, without charge, upon written request to the Secretary of Alleghany at Alleghany’s principal executive offices. The primary functions of each committee are as follows:

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Board Tenure

We believe that it is important to achieve an appropriate balance on the Board between the number of our longer-tenured directors who have a deep knowledge of Alleghany, and the number of newer directors who provide fresh perspectives. The chart below shows the breakdown by years of service on the Board. To help spur periodic change on the Board, our Corporate Governance Guidelines set a mandatory retirement age, as described on page 17, after which directors may no longer be nominated or re-nominated to the Board.

Board Leadership

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

Chief Executive Officer and Senior Management Succession Planning

A key responsibility of our chief executive officer and Board in the area of risk management is ensuring that an effective process is in place to provide continuity of leadership over the long-term. At least once each year, our Board conducts a review of chief executive officer and senior management succession planning. During this review, the chief executive officer provides the Board with recommendations on, and evaluations of, potential chief executive officer and senior management successors, succession timing for those positions, and

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development plans for the potential successors. Our Board reviews potential internal senior management candidates with our chief executive officer, including the qualifications, experience and development priorities for these individuals. Further, our Board periodically reviews the overall composition of our senior management’s qualifications, tenure and experience.

Our Board, in coordination with our Nominating and Governance Committee, also establishes steps to address emergency chief executive officer and senior management succession planning in extraordinary circumstances. Our emergency chief executive officer succession planning is intended to enable us to respond to unexpected position vacancies, including those resulting from a major catastrophe, by continuing our operation and minimizing potential disruption or loss of continuity to our business and operations.

Board Evaluation

Each year, the Board and each of its committees conducts an evaluation of their respective performance, effectiveness and fulfillment of fiduciary duties. The evaluation process is overseen by the Nominating and Governance Committee and is reviewed annually to determine whether it is designed effectively and assure that appropriate feedback is being sought and reviewed. The Board evaluation is done anonymously to encourage candid feedback, supplemented by individual director interviews with the Chairman. The results of the Board and committee evaluations are reported to and reviewed by the full Board. In general, in 2015 the Board and each committee were satisfied with their respective performance and considered themselves to be operating effectively, with appropriate balance among governance, oversight, strategic and operational matters.

Board Role in Risk Oversight

The Board oversees risk management directly and through its committees. In addition, Alleghany management has several committees that it uses to monitor and manage risk at Alleghany and its subsidiaries, including an Enterprise Risk Management, or “ERM,” Committee, Reinsurance Security Committee and Ethics and Legal Compliance Committee. Alleghany management regularly reports to the Board and, as appropriate, to its committees on management’s risk activities, Alleghany’s exposure and risk assessments. ERM is a standing agenda item at each Board meeting and the chief risk officer, Alleghany management and Board discuss existing and emerging risks, controls and procedures, risk assessments and initiatives at such meetings. Each year, at the Board’s January meeting, the Board receives a formal report on enterprise risk management from Alleghany’s chief risk officer and, at the same meeting, considers Alleghany’s three-year financial estimates and the evaluation of the President and chief executive officer, allowing the Board to consider risk and risk management in the context of Alleghany’s strategic plan and management’s performance. Each year, at the Audit Committee’s June meeting, it receives a formal report on enterprise risk management from Alleghany’s chief risk officer and a formal report on legal compliance from Alleghany’s chief compliance officer, which are also copied to the Board, and the chief risk officer and chief compliance officer subsequently report thereon to the Board. The Board receives updates on material developments with respect to risk management and legal compliance matters at its other regularly scheduled meetings. The Compensation Committee regularly monitors compensation policies, practices and outstanding awards to determine whether Alleghany’s risk management and incentive objectives are being met with respect to group-wide employee incentives. The Board believes that risk oversight is a responsibility of the entire Board, and it does not look to any individual director or committee to lead it in discharging this responsibility.

DirectorsDirectors’ Nominations and Qualifications

The Nominating and Governance Committee identifies and recommends candidates for election to the Board, consistent with general criteria approved by the Board. The Board has not approved any specific criteria that must be met by each director nominee nor established a procedure for identifying and evaluating nominees for director. The Board believes that establishing such criteria is best left to an evaluation of Alleghany’s needs at the time that a nomination is considered. The Board generally seeks members with diverse business and professional backgrounds and outstanding integrity and judgment, and such other skills and experience as will enhance the Board’s ability to best serve Alleghany’s interests. As a general matter, the Nominating and Governance Committee does consider diversity in identifying and evaluating possible nominees for director.

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

A director is required to notify the Nominating and Governance Committee when a director’s principal occupation or business association changes substantially. The Nominating and Governance Committee will

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consider whether any such change may materially interfere with the director’s service as a director of Alleghany and make a recommendation to the Board in this regard.

During 2018, at the request of the Board, the Nominating and Governance Committee undertook a process to identify a new director. The Nominating and Governance Committee determined that it would seek to identify a candidate who would have complementary business experience and would enhance board diversity. The Nominating and Governance Committee solicited directors to determine criteria for a prospective director and engaged Spencer Stuart, a nationally recognized search firm, to assist the Nominating and Governance Committee in identifying and evaluating potential nominees, including those potential nominees proposed by the directors. Spencer Stuart provided background information to the Nominating and Governance Committee regarding potential candidates meeting its search criteria and regularly communicated with the Nominating and Governance Committee to discuss such potential candidates. After review and discussion, the Nominating and Governance Committee and Spencer Stuart identified potential nominees to be interviewed. The Nominating and Governance Committee regularly reported to the Board regarding the search’s progress. The leading candidates were then interviewed by the members of the Nominating and Governance Committee, Jefferson W. Kirby, Chairman of the Board, and Weston M. Hicks, Alleghany’s President and chief executive officer. At its meeting on November 19, 2018, the Nominating and Governance Committee determined to recommend to the Board that Ms. Lauren M. Tyler, a potential nominee who met the criteria outlined by the Board, was qualified to join the Board and that she should meet with directors at the Board’s meeting the following day and, subject to the Board’s concurrence, Ms. Tyler should be elected to the Board at its January 15, 2019 meeting. The Board met with Ms. Tyler at its meeting on November 20, 2018, and Ms. Tyler was elected as a director by the Board at its January 15, 2019 meeting, to serve until the 2019 Annual Meeting.

Communications with Directors

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

Stockholder Engagement

Alleghany is committed to the interests of its stockholders and recognizes that communicating with stockholders on a regular basis is a critical part of this commitment. In this regard, Alleghany actively engages with its stockholders in order to understand fully their viewpoints concerning Alleghany and to help stockholders better understand Alleghany’s strategy and performance. Management regularly engages with investors by participating in industry conferences, and also meets in person and by telephone with stockholders at other times throughout the year to solicit input and answer questions. Management also communicates to stockholders the Board’s willingness to meet with them upon request and shares stockholder viewpoints with the Board. We believe our regular engagement with stockholders has been productive and provides an open exchange of ideas and perspectives for both Alleghany and its stockholders. Although we are open to meeting with all Alleghany stockholders, in 2018, we met withnon-affiliated stockholders who held shares representing approximately 53% of Alleghany’s shares of common stock held bynon-affiliates.

Director Retirement Policy

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

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Codes of Ethics

Alleghany has adopted an Employee Code of Business Conduct and Ethics for all employees of Alleghany and its subsidiaries, a Financial Personnel Code of Ethics for its chief executive officer, chief financial officer, chief accounting officer and all other officers in its Finance Department, a Director Code of Business Conduct and Ethics for members of the Board, a Code of Business Conduct and Ethics for Our Business Partners for third parties with whom we do business, and the Corporate Governance Guidelines. A copy of each of these documents is available on Alleghany’s website at www.alleghany.com or may be obtained, without charge, upon written request to the Secretary of Alleghany at Alleghany’s principal executive offices. Alleghany will disclose on its website any substantive amendments to its codes of ethics and any waivers from the provisions of its codes of ethics made with respect to its chief executive officer, chief financial officer or chief accounting officer (or persons performing similar functions), as well as with respect to any other executive officer or any director of Alleghany.

Majority Election of Directors

TheBy-Laws provide for a majority voting standard for the election of directors for uncontested elections. In connection with such provision of theBy-Laws, the Corporate Governance Guidelines provide that a director nominee, as a condition of his or her nomination, shall tender to the Board at the time of nomination an irrevocable resignation effective if such nominee fails to receive the majority vote required by theBy-Laws and the Board determines to accept such resignation. In the event that a director nominee fails to receive the requisite majority vote, the Nominating and Governance Committee will evaluate such resignation in light of Alleghany’s

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best interests and make a recommendation to the Board as to whether it should accept the resignation. In making its recommendation, the Nominating and Governance Committee may consider any factors it deems relevant, including:

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

Director Stock Ownership Guidelines

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

Hedging and Pledging Policies

Alleghany maintains a policy on insider trading and compliance that prohibits directors from directly or indirectly purchasing or using financial instruments designed to hedge or offset any decrease in the market value of Alleghany securities that they own. In addition, under such policy, directors are prohibited from pledging Alleghany securities as collateral.

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Related Party Transactions

The Board has adopted a written Related Party Transaction Policy, or “the Policy.” Pursuant to the Policy, all related party transactions must be approved in advance by the Board. Under the Policy, a related party transaction means any transaction, other than compensation for services as an officer or director authorized and approved by the Compensation Committee or the Board, in which Alleghany or any of its subsidiaries is a participant and in which any of the following persons has or will have a direct or indirect material interest:

A person who has a position or relationship with a firm, corporation or other entity may be deemed to have an indirect interest in any transaction in which that entity engages. However, a person is not deemed to have an interest if such interest arises only from such person’s position as a director of another corporation and/or such person’s direct and indirect ownership of less than 10% of the equity of such firm, corporation or other entity.

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

As initially disclosed in the proxy statement prepared for the 2017 Annual Meeting of Stockholders, Zachary A. Hicks, a son of Weston M. Hicks, Alleghany’s President and chief executive officer, commenced employment with TransRe as an underwriter in March 2017. Zachary Hicks’s 2018 aggregate compensation was $125,365 and was established in accordance with TransRe’s employment and compensation practices applicable to employees with equivalent qualifications, experience, and responsibilities. Zachary Hicks is also eligible to participate in TransRe’s employee benefit programs on the same basis as other eligible employees. Mr. Hicks did not participate in TransRe’s compensation decisions relating to Zachary Hicks.

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PRINCIPAL STOCKHOLDERS

The following table sets forth the beneficial ownership of each person who, based upon filings made by such person with the SEC, as of March 1, 2016,2019, was the beneficial owner of more than five percent of the outstanding common stock.

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EXECUTIVE OFFICERS

The name, age, current position, date elected and prior business experience of each of the Named Executive Officers is as follows:

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SECURITIES OWNERSHIP OF DIRECTORS AND EXECUTIVE OFFICERS

The following table sets forth, as of March 1, 2016,2019, the beneficial ownership of common stock of each of the nominees named for election as a director, each of the other current directors, each of the executive officers named in the Summary Compensation Table on page 5459 and all nominees, directors and executive officers as a group.

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Section 16(a) Beneficial Ownership Reporting Compliance

Alleghany has determined that, except as set forth below, no person who at any time during 20152018 was a director, officer or beneficial owner of more than 10% of common stock failed to file on a timely basis reports required by Section 16(a) of the Securities Exchange Act of 1934, as amended, or the “Exchange Act,” during 2015.2017. This determination is based solely upon Alleghany’s review of Forms 3, 4 and 5, and written representations that no Form 5 was required, which such persons submitted to Alleghany during or with respect to 2015. Weston M. Hicks filed2018. In February 2018, the Board declared a special dividend of $10.00 per share for stockholders of record on March 5, 2018. Under the 2005 Directors’ Plan, 2010 Directors’ Plan and 2015 Directors’ Plan, when Alleghany pays a cash dividend on its common stock, each director holding restricted stock units, or “RSUs,” awarded under such plans is credited with a corresponding dividend on his or her RSUs in the form of additional RSUs. Due to inadvertent administrative oversight, the Form 4 required to be filed for eachnon-employee director credited with a dividend payment on April 2, 2015 reporting a transaction that occurredhis or her RSUs in the form of additional RSUs was not filed within two business days of the date of the dividend payment. Such Forms 4 were filed on January 2, 2015.

PROPOSAL 1. ELECTION OF DIRECTORS

Nominees for Election

Karen Brenner, and John G. Foos and Lauren M. Tyler have been nominated by the Board for election as directors at the 20162019 Annual Meeting, each to serve for a term of three years, subject to Alleghany’s director retirement policy, until the 20192022 Annual Meeting of Stockholders and until herhis or hisher successor is duly elected and qualified. Each of the nominees is a current member of the Board and was recommended to the Board for nomination by the Nominating and Governance Committee. Following the 2016 Annual Meeting, Mr. BradleyMs. Brenner and Mr. Johnson, members of the class of 2016, will no longer serve as directors of Alleghany. Mr. Foos was last elected to the Board at the 2015 Annual Meeting held on April 24, 2015, and has been added by the Board to the class of directors standing for re-election at the 2016 Annual Meeting in order to make the classes of the Board as nearly equal in size as practicable. Ms. Brenner waswere last elected by stockholders at the 20132016 Annual Meeting of Stockholders held on April 26, 2013.22, 2016. At a Board meeting on January 15, 2019, the Board increased its size from eight to nine directors and elected Lauren M. Tyler to fill the vacancy created by such increase in size. Ms. Tyler was elected for a term to expire at the 2019 Annual Meeting.

Information about Voting

Proxies received from Alleghany stockholders of record will be voted for the election of the twothree nominees named above as Alleghany directors unless such stockholders indicate otherwise. If any of the foregoing nominees is unable to serve for any reason, which is not anticipated, the shares represented by proxy may be voted for such other person or persons as may be determined by the holders of such proxy unless stockholders indicate otherwise. A nominee for director shall be elected to the Board if such nominee receives the affirmative vote of a majority of the votes cast with respect to the election of such nominee. A majority of votes cast means the number of votes cast “for” a nominee’s election must exceed the number of votes cast “against” the nominee’s election. Abstentions and brokernon-votes (see page 10)pages 10 and 11) do not count as votes cast “for” or “against” the nominee’s election, but will be counted as present at the meeting for quorum purposes.

Director Qualifications

The following information includes for each of the nominees named for election as director at the 20162019 Annual Meeting, and each of the other directors of Alleghany:

In addition to the information regarding the specific experience, qualifications, attributes and skills that led the Board to the conclusion that each of the nominees named for election as director should be elected as a director of Alleghany, Alleghany believes that each of the nominees, and each of the other directors of Alleghany, has a reputation for integrity, honesty and adherence to high ethical standards. Alleghany also believes that each of the nominees, and each of the other directors of Alleghany, has demonstrated business acumen and an ability to exercise sound judgment, as well as a commitment to service to Alleghany and to the Board.

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Nominees for Election

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Other Alleghany Directors

Stephen P. BradleyIan H. Chippendale Age 7470 Director since 2012 Member of the AuditCompensation     Committee Member of the Nominating and Governance Committee Retiring effective at the     2016 Annual Meeting				Mr. Bradley is currently the William Ziegler Professor of Business Administration Emeritus at the Harvard Business School where he has been a professor since 1968. In addition, Mr. Bradley currently serves as a director of CRICO/Risk Management Foundation, a medical professional liability carrier. Mr. Bradley was a director of Transatlantic Holdings, Inc. prior to March 6, 2012 and also previously served as a director of CIENA Corp. and i2 Technologies, Inc. Mr. Bradley’s qualifications to serve on the Board also include his academic experience at the Harvard Business School relating to his work as a professor of competitive and corporate strategy and his considerable experience as a consultant and as a director of public companies.
Ian H. Chippendale Age 67 Director since 2012 Chairman of the CompensationGovernance Committee Term expires in 20172020				Mr. Chippendale is the retired Chairman (from September 2003 to December 2006) of RBS Insurance Group, Ltd., an insurance company. In addition, Mr. Chippendale served as a director of HomeServe plc, an insurance company, from January 2007 through March 2015, and was a director of Transatlantic Holdings, Inc.TransRe prior to March 6, 2012.   Mr. Chippendale’s qualifications to serve on the Board also include his insurance industry knowledge and his international experience, including his service as the Chairman of RBS Insurance Group, Ltd.
Weston M. Hicks Age 5962 Director since 2004 Term expires in 20172020				Mr. Hicks has been Alleghany’s President and chief executive officer since December 2004. In addition, Mr. Hicks iswas a director of AllianceBernstein Corporation, an investment management and research company.from July 2005 to April 2017.   Mr. Hicks’s qualifications to serve on the Board also include his years of experience as an executive in the insurance and financial services industry, particularly his experience as Alleghany’s President and chief executive officer during the past eleven13 years, and his experience as an analyst of propertyandproperty and casualty insurance companies.

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Thomas S. Johnson Age 75 Director since 1997     and for 1992-1993 Member of the Compensation     Committee Member of the     Nominating and     Governance Committee Retiring effective at the     2016 Annual Meeting				Mr. Johnson was Chairman and Chief Executive Officer of GreenPoint Financial Corporation and its subsidiary GreenPoint Bank from 1993 until his retirement on December 31, 2004. Mr. Johnson currently serves as a director of Santander Holdings USA, Inc., a subsidiary of global commercial and retail bank Banco Santander, S.A., and as a director of Santander Bank, N.A., a subsidiary of Santander Holdings USA, Inc. Mr. Johnson previously served as a director of the Lower Manhattan Development Corporation, the Institute of International Education, The Phoenix Companies, Inc., R.R. Donnelly & Sons Company and the Federal Home Loan Mortgage Corporation. Mr. Johnson’s qualifications to serve on the Board also include his over 30 years of experience as a financial services industry executive, particularly as Chairman and Chief Executive Officer of GreenPoint Financial Corporation, his experience as a member of the boards of directors of other companies and his financial literacy.
Jefferson W. Kirby Age 5457 Director since 2006 Term expires in 20172020				Mr. Kirby has been Chairman of the Board of Alleghany since July 2010. Mr. Kirby has been the Managing Member of Broadfield Capital Management, LLC, an investment advisory services company, since July 2003. Mr. Kirby was a director of Somerset Hills Bancorp, a bank holding company, from 2008 until May 2013. He has served on numerous corporate boards and continues to serve on several charitable boards.   Mr. Kirby’s qualifications to serve on the Board also include his over 25 years of experience in financial services and investment management, including his service as a Vice President of Alleghany from 1994 until June 2003 and as an investment manager.
William K. Lavin Age 7174 Director since 1992 Chairman of the Audit     Committee Member of the Compensation     Committee Term expires in 20182021				Mr. Lavin has been a financial consultant since October 1994, and currently serves as a director of Artisanal Brands, Inc., a specialty foods company.   Mr. Lavin’s qualifications to serve on the Board also include his business experience as an executive with public and private companies, his extensive experience with public and financial accounting matters for such companies and his financial literacy.

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Compensation of Directors

The information under this heading relates to the compensation during 20152018 of thosenon-employee directors who served on the Board at any time during 2015.2018. Employee directors are not separately compensated for their service on the Board.

20152018 Director Compensation

Fees Earned or Paid in Cash

Following is information regarding fees earned and paid in cash to directors for service on the Board and its Committees: