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LETTER FROM THE BOARD OF DIRECTORS

FROM OUR BOARD OF DIRECTORS

Dear Fellow Shareholders:

2019 was a strong year for our Company driven by good operating results in our main businesses and strong absolute investment returns.  Our share price increased 30%.  We also deployed $435 million into businesses during the year, and ended 2019 with undeployed capital at $1.0 billion.  This level of undeployed capital reflects management’s thoughtful and patient redeployment and return of capital over the past several years following sales of a number of our large businesses between 2015 and 2017 that generated $4 billion in proceeds.  Your Board believes that this patient approach to redeployment will serve owners well in the years to come.

Strong Financial Performance

We finished 2019 with book value per share of $1,024 and adjusted book value per share of $1,018, increases of 14% and 15% from the prior year.  Excluding the gain from the MediaAlpha transaction in February 2019, BVPS and ABVPS each grew 8%.  We focus management on growing ABVPS because we believe that, in the long term, growth in market value per share will follow growth in ABVPS.  In 2019, our one-year total shareholder return was 30.2%. Each of our main operating businesses performed well this year, and our total investment portfolio returned 20.4% (15.5% excluding the gain from the MediaAlpha transaction).  A very satisfying result.

Execution of Our Business Strategy

During 2019, your Company made good progress on capital deployment, putting $435 million to work.  Three significant deals emerged from our platform companies: (i) Embrace, a pet insurance MGA acquired by NSM, (ii) the acquisition of NSM’s collector car renewal rights and (iii) our buyout of Oaktree’s 50% interest in Kudu.  At the parent company, we closed the Elementum transaction and strengthened our deal pipeline considerably.

Thoughtful Approach to Board Composition with a Demonstrated Commitment to Refreshment

As part of our ongoing commitment to creating a balanced and effective Board with diverse viewpoints, skills, and deep industry expertise related to our Company strategy, Peter Carlson joined the Board in 2019. Pete brings over thirty years of accounting and audit experience in the insurance industry.  He is the former Executive Vice President and COO of Brighthouse Financial and the former Executive Vice President and CAO of MetLife. Our Board has a robust refreshment process and, since 2017, four new independent directors have joined the Board, replacing three long-serving directors. Average tenure now stands at seven years, and women comprise 25% of our members.

Ongoing Dialogue with Shareholders Through Proactive Engagement

Engaging with our shareholders remains a high priority.  Over the last year, members of the Board and management reached out to shareholders owning 72% of White Mountains’ outstanding shares and met with all shareholders who requested meetings, who represented 26% of our shares outstanding.  Over the past several years, feedback received from these discussions has helped guide changes to our executive compensation program and further enhance our disclosures about the skills and areas of expertise of our Board, the Board’s oversight of risk management, and our human capital management initiatives.  In this year’s proxy statement, we have included a Board skills matrix, enhanced our disclosure around Board oversight of ESG, and added a section on human capital management.

The global pandemic is challenging all of us in 2020, but our core principles serve us equally well in times of calm and times of uncertainty.  We wish you well as you manage through these turbulent times.  It is a privilege to serve as your Board, and we greatly value your support of White Mountains.

Sincerely,

The White Mountains Insurance Group Board of Directors

April 7, 2020

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White Mountains Insurance Group, Ltd. (the “Company”, “Registrant” or “WTM”) is an exempted Bermuda limited liability company whose principal businesses are conducted through its insurance subsidiaries and other affiliates.  Within this proxy statement, the term “White Mountains” is used to refer to one or more entities within the consolidated organization, as the context requires.

White Mountains is engaged in the business of making opportunistic and value-oriented acquisitions of businesses and assets in the insurance, financial services and related sectors, operating these businesses and assets through ourits subsidiaries and, if and when attractive exit valuations become available, disposing of these businesses and assets.

White Mountains currently conducts its business primarily in threefour areas:  municipal bond insurance, marketing technologyspecialty insurance distribution, capital solutions for asset management firms, and other operations.  White Mountains’s municipal bond insurance business is conducted through its subsidiary HG Global Ltd. (“HG Global”) and through its wholly-owned reinsurance subsidiary HG Re Ltd. (“HG Re” and, collectively, “HG Global”).  HG Global was established to fund the startup of and provide reinsurance, through HG Re, to Build America Mutual Assurance Company (“BAM”), a mutual municipal bond insurance company.  White Mountains’s marketing technologyspecialty insurance distribution business is conducted through its subsidiaries QL Holdingssubsidiary NSM Insurance HoldCo, LLC and its subsidiaries (collectively, “NSM”).  White Mountains provides capital solutions for asset management firms through its subsidiary QuoteLab,Kudu Investment Management, LLC and its subsidiaries (collectively, “MediaAlpha”“Kudu”).  White Mountains’s investing activities are conducted throughother operations consist of the Company and its wholly ownedwholly-owned subsidiary, White Mountains Capital, Inc (“WM Capital”), its other intermediate holding companies, its wholly-owned investment management subsidiary, White Mountains Advisors LLC (“WM Advisors”)., investment assets managed by WM Advisors, and certain other consolidated and unconsolidated entities and certain other strategic investments.  White Mountains’s reportable segments are HG Global/BAM, MediaAlpha,NSM, Kudu and Other Operations.

On September 28, 2017, White Mountains completed the disposition of OneBeacon Insurance Group, Ltd. (“OB” or “OneBeacon”) to Intact Financial Corporation.  While owned by White Mountains, OneBeacon was a provider of a wide range of property and casualty insurance products in the United States primarily through independent agencies, regional and national brokers, wholesalers and managing general agencies.   For additional information on our business segments, please refer to the Form 10-K for 20172019, which can be found at www.whitemountains.com.

The 20182020 Annual General Meeting will be confined to a Membershareholder vote on the proposals set forth in this Proxy Statement and on such other matters properly brought before the meeting.

For a reconciliation of non-GAAP measures used in this Proxy Statement to their most comparable GAAP measures, see Annex A.

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PROXY SUMMARY

This summary highlights information contained elsewhere in this Proxy Statement.  This summary does not contain all of the information that you should consider.  You should read the entire Proxy Statement carefully before voting.

This Proxy Statement and the accompanying proxy card are being distributed and made available to shareholders on or about April 23, 2020.

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Chief Executive Officer:

Other NEOs:

The Board is responsible for overseeing the Company’s management of ESG matters.  Following our core operating principle of Thinking Like Owners, we maintain robust and owner-focused corporate governance practices.  With respect to environmental matters, though our business operations do not have a large physical footprint, we strive to make meaningful contributions towards protecting the environment and contributing to our local communities.  As to sustainability, the Board oversees the Company’s corporate culture and reinforces the importance of promoting a respectful and diverse work environment that enables our employees to be productive and feel valued.  We focus on building long-term value for our owners by building enduring partnerships with the management teams and our partners in our various businesses and in the communities in which we operate.  The Board is proud of the Company’s efforts, which can generally be broken down into four main categories: (i) human capital management, (ii) diversity and inclusion, (iii) social impact, and (iv) sustainability.  For further details on our Company’s efforts on these categories, please refer to page 19 of the proxy statement.

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WHITE MOUNTAINS INSURANCE GROUP, LTD.

NOTICE OF 20182020 ANNUAL GENERAL MEETING OF MEMBERS

TO BE HELD MAY 24, 201821, 2020

Notice is hereby given that the 20182020 Annual General Meeting of Members of White Mountains Insurance Group, Ltd. will be held on Thursday, May 24, 201821, 2020 at 8:10:00 am AtlanticEastern Time at Rosewood Bermuda Hotel, 60 Tucker’s Point Drive, Hamilton Parish, Bermuda.White Mountains Insurance Group, 23 South Main Street, Suite 3B, Hanover, New Hampshire.  At this meeting, you will be asked to consider and vote upon the following proposals:

1)election of threetwo directors to Class IIIII with a termterms ending in 2021;2023;

2)approval of the advisory resolution on executive compensation; and

3)approval of the appointment of PricewaterhouseCoopers LLP (“PwC”) as the Company’s Independent Registered Public Accounting Firm for 20182020.

The Company’s audited financial statements for the year ended December 31, 2017,2019, as approved by the Company’s Board of Directors, will be presented at this Annual General Meeting.

MembersShareholders of record of common shares on the record date, Monday,Wednesday, April 2, 2018,1, 2020, (1) who are individuals, may attend and vote at the meeting in person or by proxy or (2) that are corporations or other entities, may have their duly authorized representative attend and vote at the meeting in person or by proxy.  A list of all MembersShareholders entitled to vote at the meeting will be open for public examination during regular business hours beginning on or about April 24, 201820, 2020 at the Company’s registered office located at Clarendon House, 2 Church Street, Hamilton HM 11, Bermuda.

All Members are invited to attend this meeting.

MembersShareholders are invited to complete and sign the accompanying proxy card to be returned to White Mountains Insurance Group, Ltd., Proxy Services, c/o Computershare Investor Services, P.O. Box 505008, Louisville, Kentucky 40233-9814, in the envelope provided, whether or not they expect to attend the meeting.  MembersShareholders may also vote their shares by telephone or via the internet in accordance with the instructions on your proxy card.

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WHITE MOUNTAINS INSURANCE GROUP, LTD.

PROXY STATEMENT

This Proxy Statement is being furnished in connection with the solicitation of proxies on behalf of the Company’s Board of Directors (the “Board”) for the 20182020 Annual General Meeting of Members (the “2018“2020 Annual Meeting”), to be held on Thursday, May 24, 201821, 2020 at Rosewood Bermuda Hotel, 60 Tucker’s Point Drive, Hamilton Parish, Bermuda.White Mountains Insurance Group, 23 South Main Street, Suite 3B, Hanover, New Hampshire.

Holders of the Company’s common shares (“Shareholders”), par value $1.00 per share, as of the close of business on Wednesday, April 1, 2020, the record date, are entitled to vote at the meeting.  The solicitation of proxies will be made primarily by mail, and the Proxy Statement and related proxy materials will be distributed to registered MembersShareholders on or about April 24, 2018.

Holders of the Company’s common shares (“Members”), par value $1.00 per share, as of the close of business on Monday, April 2, 2018, the record date, are entitled to vote at the meeting.23, 2020.

You can ensure that your common shares are properly voted at the meeting by completing, signing, dating and returning the enclosed proxy card in the envelope provided.  MembersShareholders may also vote their shares by telephone or via the internet in accordance with the instructions on your proxy card.  A Member hasShareholders have the right to appoint another person (who need not be a Member)Shareholder) to represent the MemberShareholder at the meeting by completing an alternative form of proxy which can be obtained from the Corporate Secretary or by notifying the Inspectors of Election (see page 37)54).  Every MemberShareholder entitled to vote has the right to do so either in person or by one or more persons authorized by a written proxy executed by such MemberShareholder and filed with the Corporate Secretary.  Any proxy duly executed will continue in full force and effect unless revoked by the person executing it in writing or by the filing of a subsequent proxy.

Sending in a signed proxy will not affect your right to attend the meeting and vote.  If a MemberShareholder attends the meeting and votes in person, his or her signed proxy is considered revoked.

IMPORTANT VOTING INFORMATION

If you hold your shares through a broker, bank or other financial institution, in order for your vote to be counted on any matter other than Proposal 3 (the ratification of the selection of PwC as the Company’s auditor for 2018)2020), you must provide specific voting instructions to your broker, bank or financial institution by completing and returning the proxy card or following the instructions provided to you to vote your shares via telephone or the Internet.internet.  Voting deadlines vary by institution.  Please check with your broker, bank or other financial institution for the voting cut-off date for WTM.

Your Participation in Voting the Shares You Own Is Important

Voting your shares is important to ensure that you have a say in the governance of your company.  Please review the proxy materials and follow the instructions on the proxy card to vote your shares.  We hope you will exercise your rights and fully participate in your company’s future.

More Information Is Available

If you have any questions about this rule or the proxy voting process in general, please contact the broker, bank or other financial institution where you hold your shares.  The U.S. Securities and Exchange Commission (“SEC”) has information available on the internet at: https://www.investor.gov/system/files/publications/documents/english/sec-guide-to-proxy-brochures.pdf with more information about your voting rights as a shareholder.

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PROPOSAL 1 - ELECTION OF THE COMPANY’S DIRECTORS

THE BOARD OF DIRECTORS

The Board is divided into three classes (each a “Class”).  Each Class serves a three-year term.

At the 20182020 Annual General Meeting, G. Manning Rountree and Mary C. Choksi Philip A. Gelston, and Edith E. Holiday are nominated to be elected to Class IIIII with a term ending in 2021.2023.  Mr. Rountree and Ms. Choksi were previously elected by Shareholders.

The Board recommends a vote FOR Proposal 1 which calls for the election of the 20182020 nominees.

The current members of the Board and terms of each Class are set forth below:

* Nominated to be elected at the 2018 Annual General Meeting to Class III with a term ending in 2021.

*Nominated to be elected at the 2020 Annual General Meeting to Class II with a term ending in 2023. **Retiring from the Board, effective as of the 2018 Annual General Meeting. **Retiring from the Board at completion of current term, which ends as of the 2020 Annual General Meeting.

The Board is comprised of eight independent directors and the Chief Executive Officer.  Upon Mr. Frinquelli’s retirement from the Board at the end of the 2018 term, the Board will be comprised of seven independent directors and the Chief Executive Officer.

Board Composition and Refreshment

The Company is committed to maintaining a Board with members from a variety of backgrounds to promote diverse, independent thinking.  Diversity considerations are an important part of the director search process, and the Company believes that continually enhancing the makeup of the Board is important.  Currently, the board has 25% gender diversity, with both women also chairing a Committee.  Out of eight directors, seven are independent, with 100% independence on key committees.  The Company actively refreshes the Board to ensure the directors collectively have the optimal mix of diverse skills and experiences to effectively oversee the business as it evolves.  Our most recent addition in 2019 was Peter Carlson.  Mr. Carlson brings over thirty years of accounting and audit experience and is the former Executive Vice President and COO of Brighthouse Financial.  In December 2019, Mr. Carlson joined MiMedx Group, an industry leader in advanced wound care and an emerging therapeutic biologics company, and became its Chief Financial Officer in March 2020.

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Director Skills and Qualifications

Our Board seeks Directors with a broad range of skills, experience and perspectives in order to ensure effective oversight of the Company’s strategies and risks.  The Board believes its members should have a diversity of skillsmust be willing and experience and be willingable to devote adequate time and effort to Board responsibilities.  In evaluating director candidates, the Compensation/Nominating and& Governance Committee evaluates attributes such as independence, integrity, expertise, breadth of experience, diversity, knowledge about the Company’s business and industry and ownership interest in the Company.  Key aspectsThe skills matrix below highlights our Board’s key skills and qualifications that are directly relevant to our business, strategy and operations.  The Board reviews this matrix and the overall Board composition periodically in order to ensure the appropriate balance of diversity, knowledge and experience.

The lack of a checkmark for a particular item does not mean that the directors’ experiences, qualifications and skills are included in their individual biographies.director does not possess that qualification, skill or experience, but rather the checkmark indicates that the item is a particularly prominent qualification, skill or experience that the director brings to the Board.

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Board of Directors

Class I -– Term Ending in 20192022

Morgan W. Davis has been

Morgan W. Davis Chairman

Qualifications

·Joined in 2006 ·Age: 69 ·Chairman of the Board ·Committees: Compensation/Nominating & Governance, Executive (Chair)

Experience: ·Appointed Chairman of the Board in March 2017 ·Formerly Managing Director of OneBeacon (2001 to 2005) and served in a variety of capacities for White Mountains subsidiaries (1994 to 2001) ·Prior to 1994, Mr. Davis had 21 years of experience in the insurance industry, mostly at Fireman’s Fund Insurance Company and INA/Cigna ·Served as a director of OneBeacon from 2005 until its acquisition by Intact Financial Corporation in September 2017 ·Served as a director of Endurance Specialty Holdings, and as a member of its Finance and Compensation Committees, from 2015 until its acquisition by SOMPO Holdings, Inc. in March 2017 ·Serves on the Board of Trustees of Lipscomb University and on the Board of Directors for the United States African Development Foundation Mr. Davis has extensive executive and board-level experience gained over the course of his more than 45-year career in the property and casualty insurance industry. Select Board Service: ·Compare.com (Private) ·MediaAlpha (Private) ·NSM Insurance Group (Private)

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Table of the Company since 2006 and was appointed as Chairman of the Board on March 1, 2017.  Mr. Davis formerly was a Managing Director of OneBeacon from 2001 to 2005 and served in a variety of capacities for subsidiaries of White Mountains from 1994 to 2001.  Prior to 1994, Mr. Davis had 21 years of experience in the insurance business, mostly at Fireman’s Fund Insurance Company and INA/Cigna.  Mr. Davis served as a director of OneBeacon until September 2017.  He currently serves as a director of Compare.com (formerly Inspop USA LLC) and MediaAlpha.  Mr. Davis served as a director of Endurance Specialty Holdings, and as a member of its Finance and Compensation Committees, from 2015 until its acquisition by SOMPO Holdings, Inc. in March 2017.  Mr. Davis has extensive executive and board-level experience gained over the course of his more than forty-five-year career in the property and casualty insurance industry.

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Class II – To Be Elected to a Term Ending in 20202023

Yves Brouillette has been a director of the Company since 2007.  He has been the President of Beluca Investment, Inc. since 2006.  Previously, Mr. Brouillette had been with ING since 1989, serving in many leadership positions at ING companies, including most recently as the CEO for ING Latin America operations in Mexico, Brazil, Chile and Peru (2002-2005).  From 2004 until May 2017, Mr. Brouillette was a director of Intact Financial Corporation (formerly ING Canada), where he served on the Audit and Risk Committees, and was the Chairman of the Board (2003-2007).  Mr. Brouillette is an actuary and has over 30 years of experience in the property and casualty insurance industry in North and South America.

G. Manning Rountree was appointed as a director and Chief Executive Officer of the Company on March 1, 2017.  Previously, Mr. Rountree served as an Executive Vice President of the Company and President of White Mountains Capital, Inc. (“WM Capital”).  He joined White Mountains in 2004 and served as President of WM Advisors from March 2009 until December 2014.  Prior to joining White Mountains, Mr. Rountree was a Senior Vice President at Putnam Investments for two years.  Prior to joining Putnam Investments, Mr. Rountree spent three years with McKinsey & Company. Mr. Rountree is a director and member of the Risk Management Committee of Admiral Group plc, a large car insurance provider based in the UK.

Class III – To Be Elected to a Term Ending in 20212023

Mary C. Choksi11

has been a directorTable of the company since 2017.  Ms. Choksi was a founding partner of Strategic Investment Group (Strategic), an investment management enterprise founded in 1987 which designs and implements global investment strategies for large institutional and individual investors. She served as a Senior Managing Director/Senior Advisor of Strategic until February 2017. Ms. Choksi has served as a Director of the Avis Budget Group since 2007, where she serves on the Audit and Governance Committees, and of the Omnicom Group since 2011, where she serves on the Audit and Compensation Committees. She is also an Independent Director of the Franklin and Templeton series of mutual funds. Ms. Choksi was a founder and, until May 2011, a Managing Director of Emerging Markets Management LLC, which manages portfolios of emerging market equity securities, primarily for institutional investors. Prior to 1987, Ms. Choksi worked in the Pension Investment Division of the World Bank.

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CORPORATE GOVERNANCE

Corporate governance is the system by which companies are directed and controlled and involves the distribution of rights and responsibilities among the Board, management and theThe Company’s Members.  The Company has established Corporate Governance Guidelines that spell out itsour overall approach towards corporate governance.

The Company also has a Code of Business Conduct that applies to all directors, officers and employees in carrying out their responsibilities to, and on behalf of, the Company.  No waivers of the Code of Business Conduct were requested of, or granted by, the Board for any director or executive officer during 2017.2019.

The Company’s Corporate Governance Guidelines and Code of Business Conduct are available at our website, www.whitemountains.com.  These documents are available in print, free of charge, to any Membershareholder upon request.

The Board

The day-to-day management of the Company, including preparation of financial statements and short-term and long-term strategic planning, is the responsibility of management.  The primary responsibility of the Board is to oversee and review management’s performance of these functions in order to advance the long-term interests of the Company and its Members.shareholders.

In fulfilling this responsibility, directors must exercise common sense business judgment and act in what they reasonably believe to be in the best interests of the Company and its Members.Company.  Directors are entitled to rely on the honesty and integrity of senior management and the Company’s outside advisors and auditors.  However, it is the Board’s responsibility to establish that they have a reasonable basis for such reliance by ensuring that they have a strong foundation for trusting the integrity, honesty and undivided loyalty of the senior management team upon whom they are relying and the independence and expertise of outside advisors and auditors.

Mr. Davis, an independent director, serves as Chairman of the Board.  At meetings of the Board, Mr. Davis presides over a separate session of non-management directors without Company management present.  In addition to being led by an independent Board Chair, the Board is comprised of directors that, together, are knowledgeable and experienced in the Company’s business.  The Board is satisfied that the current structure provides strong oversight of the Company’s affairs.

Shareholder Engagement

Shareholder engagement is of great importance to our Board and management team as a means to solicit feedback and to ensure accountability and responsiveness to our shareholders.  Building on our 2018 engagement efforts, as part of our 2019 shareholder engagement, we reached out to shareholders owning 72% of outstanding shares and met with all shareholders who requested meetings, who represented 26% of outstanding shares.  Our Compensation / Nominating & Governance Committee Chair personally led discussions in meetings with shareholders representing 13% of outstanding shares, which were all meetings where her participation was requested.

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These discussions centered around our business strategy, corporate governance, executive compensation program, and board oversight of risk management.  More specifically, we discussed the changes we made to our compensation program in 2019, our continued board refreshment with the appointment in 2019 of our newest independent director, insurance industry veteran Peter Carlson, and our environmental and sustainability practices.  The 2019 changes to our compensation program were to (i) make our annual bonus program for executive officers entirely formulaic with a pre-established, rigorous and quantifiable performance target relevant for our Company and industry and (ii) adopt share ownership guidelines for our executive officers.  Our shareholders were overwhelmingly supportive of our executive compensation programs, including the performance metrics used in our 2019 annual bonus program and 2019-2021 long-term incentives, and our patient capital redeployment efforts.

Shareholder feedback is regularly communicated to our full Board, and the input we received directly informed enhancements implemented to our executive compensation program in 2019, as well as the expanded disclosure in this year’s proxy statement (e.g., Board’s Role in ESG Oversight and Director Skills and Qualifications with an individual skills matrix).

Director Independence

The Board has determined that a majority of the Company’s current directors are independent, as defined in Section 303A of the New York Stock Exchange (“NYSE”) Listed Company Manual.  Those directors determined to be independent are Messrs. Brouillette,Carlson, Davis, Frinquelli, Gelston, Smith and TolmanTanner and Mmes. Choksi and Holiday.  For a director to be independent, the Board must determine that the director has no relationship with the Company (other than being a director or shareholder of the Company or its subsidiaries) or has only immaterial relationships with the Company.  The Company does not apply categorical standards as a basis for determining director independence.  Accordingly, the Board considers all relevant facts and circumstances, on a case-by-case basis, in making an independence determination.

The Board notes no current relationships (other than being directors or shareholders) with Messrs. Brouillette, Frinquelli,Carlson, Gelston, TolmanSmith and SmithTanner or Mmes. Choksi and Holiday.  The Board notes a relationship with Mr. Davis, as disclosed herein under “Director Compensation”, that it concluded was immaterial and did not impair his independence.  In making its independence determinations, the Board considers all such relationships in light of NYSE standards as well as the attributes it believes should be possessed by independent-minded directors.  Those attributes include the relative impact of the transactions to the director’s personal finances, the perceived degree of dependence by the director or the Company upon the relationship or transactions continuing in the future and whether the transactions were on terms that were reasonable and competitive.

Board Meetings and Committees; Annual Meeting Attendance

During 2017,2019, the following meetings of the Board were held: sevenfour meetings of the full Board, elevennine meetings of the Audit Committee, fourfive meetings of the CompensationCompensation/Nominating & Governance Committee, three meetingsone meeting of the Performance Compensation Subcommittee three meetings of the Nominating and Governance Committee and four meetings of the Finance Committee.  During 2017,2019, each director attended more than 75% of the aggregate of: (1) the total number of meetings of the Board (held during the period for which he or she has been a director); and (2) the total number of meetings held by all committees of the Board on which he or she served.

It is White Mountains practice that all directors are invited to, receive materials for and generally attend all Committee meetings.  In addition, each Committee Chair provides regular updates to the full Board regarding Committee activities.

Directors are encouraged but are not required, to attend annual meetings.  All of the Company’s directors were in attendance at the 20172019 Annual General Meeting, which was held on May 25, 2017.23, 2019.

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Committees of the Board

Nominating and Governance Committee

The primary purposes of the Nominating and Governance Committee are to: (1) identify individuals qualified to become Board members and recommend such individuals to the Board for nomination for election to the Board; (2) make recommendations to the Board concerning committee appointments; (3) develop, recommend and annually review corporate governance guidelines applicable to the Company and oversee corporate governance matters; and (4) oversee the evaluation of the Board and management.

The Nominating and Governance Committee is currently comprised of Ms. Holiday (as Chairwoman) and Messrs. Brouillette, Davis and Smith.  The Board has determined that each current member of the Nominating and Governance Committee satisfies applicable NYSE requirements.

The Nominating and Governance Committee Charter, which outlines the duties and responsibilities of the Nominating and Governance Committee, is available at www.whitemountains.com.  The Nominating and Governance Committee Charter is available in print, free of charge, to any Member upon request.

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Interlocks and Insider Participation

No member of the Compensation/Nominating & Governance Committee was an employee of the Registrant during the last fiscal year or has served as an officer of the Registrant.

Consideration of Director Nominees

General Criteria and Process for Selection of Director Candidates.  In identifying and evaluating director candidates, the Compensation/Nominating & Governance Committee does not set specific criteria for directors.  Under its Charter, the Committee is responsible for determining desired Board skills and evaluating attributes such as independence, integrity, expertise, breadth of experience, diversity and knowledge about the Company’s business and industry and ownership interest in the Company.  In selecting director candidates, the Company seeks a diversity of skills, backgrounds and experience.  Directors must be willing to devote adequate time and effort to Board responsibilities.  As set forth in the Company’s Corporate Governance Guidelines and its Charter, the Committee is responsible for recommending director candidates to the Board.

Consideration of Director Candidates Nominated by Shareholders.  The Company has not adopted a specific policy regarding consideration of director candidates from shareholders.  Shareholders who wish to recommend candidates for consideration by the Committee may submit their nominations in writing to the Corporate Secretary at the address provided in this Proxy Statement.  The Committee may consider such shareholder recommendations when it evaluates and recommends candidates to the Board for submission to shareholders at each annual general meeting.  In addition, shareholders may nominate director candidates for election without consideration by the Committee by complying with the eligibility, advance notice and other provisions of our Bye-laws as described below.

Procedures for Nominating Director Candidates.  Under the Company’s Bye-laws, nominations for the election of directors may be made by the Board or by any shareholder entitled to vote for the election of directors (a “Qualified Shareholder”).  A Qualified Shareholder may nominate persons for election as directors only if written notice of such Qualified Shareholder’s intent to make such nomination is delivered to the Secretary not later than: (1) with respect to an election to be held at an annual general meeting, 90 days prior to the anniversary date of the immediately preceding annual general meeting or not later than 10 days after notice or public disclosure of the date of the annual general meeting is given or made available to Qualified Shareholders, whichever date is earlier, and (2) with respect to an election to be held at a special general meeting for the election of directors, the close of business on the seventh day following the date on which notice of such meeting is first given to Qualified Shareholders.  Each such notice shall set forth: (a) the name and address of the Qualified Shareholder who intends to make the nomination and of the person or persons to be nominated; (b) a representation that the Qualified Shareholder is a holder of record of common shares entitled to vote at such meeting and intends to appear in person or by proxy at the meeting to nominate the person or persons specified in the notice; (c) a description of all arrangements or understandings between the Qualified Shareholder and each such candidate and any other person or persons (naming such person or persons) pursuant to which the nomination or nominations are to be made by the Qualified Shareholder; (d) such other information regarding each candidate proposed by such Qualified Shareholder as would have been required to be included in a proxy statement filed pursuant to the proxy rules of the SEC had each such candidate been nominated, or intended to be nominated, by the Board; and (e) the consent of each such candidate to serve as a director of the Company if so elected.

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Shareholder Communications

Shareholders, employees and others interested in communicating directly with the Board, any of the Board’s Committees or any individual member of the Board should write to the addressee, c/o the Corporate Secretary, at the address presented under “Available Information” (which appears on page 55).

Risk Oversight

The Board, directly and through its Committees, plays an active role in the oversight of the Company’s risk management.  The subject of risk management is a recurring agenda item, for which the Board regularly receives reports from management on capital, investments, and operations, including the risks associated with each and the steps management is taking to manage those risks.  The Board also discusses with management the Company’s business strategy, risk appetite and appropriate levels of risk.

The Board’s committees are assigned oversight responsibility for particular areas of risk.  For example, the Audit Committee receives a report, at least annually, on company-wide risks which considers operational, financial, legal, compliance, cyber and reputational risks, as well as climate risks and sustainability matters.  The Compensation/Nominating & Governance Committee oversees risk related to executive compensation plans and implementation.  The Finance Committee oversees the risks related to managing the Company’s investment portfolio.  Full Board meetings and individual Committee meetings are scheduled so as not to overlap and all directors are encouraged to attend all committee meetings, allowing for every director to participate and provide guidance regarding any risk concerns.

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Board’s Role in ESG Oversight

The Board is responsible for overseeing the Company’s management of ESG matters.  Following our core operating principle of Thinking Like Owners, we maintain robust and owner-focused corporate governance practices.  With respect to environmental matters, while our business operations do not have a large physical footprint, we strive to make meaningful contributions towards protecting the environment and contributing to our local communities.  As to sustainability, the Board oversees the Company’s corporate culture and reinforces the importance of promoting a respectful and diverse work environment that enables our employees to be productive and feel valued.  We focus on building long-term value for our owners by building enduring partnerships with the management teams and our partners in our various businesses and in the communities in which we operate.  The Board is proud of the Company’s efforts, which can generally be broken down into four main categories:

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VOTING SECURITIES AND PRINCIPAL HOLDERS THEREOF

Voting Rights of Shareholders

As of April 1, 2020, there were 3,128,644 common shares outstanding.  Shareholders of record of common shares shall be entitled to one vote per common share, provided that if, and so long as, the votes conferred by “Controlled” common shares (as defined below) of any person constitute ten percent (10%) or more of the votes conferred by the outstanding common shares of the Company, each outstanding common share comprised in such Controlled common shares shall confer only a fraction of a vote that would otherwise be applicable according to the following formula:

[(T divided by 10)-1] divided by C

Where: “T” is the aggregate number of votes conferred by all the outstanding common shares; and “C” is the number of votes conferred by the Controlled common shares of such person.

“Controlled” common shares in reference to any person means:

(1)all common shares directly, indirectly, or constructively owned by such person within the meaning of Section 958 of the Internal Revenue Code of 1986, as amended, of the United States; and

(2)all common shares directly, indirectly, or constructively owned by any person or “group” of persons within the meaning of Section 13(d)(3) of the Exchange Act and the rules and regulations promulgated thereunder; provided that this clause (ii) shall not apply to (a) any person (or any group that includes any person) that has been exempted from the provisions of this clause or (b) any person or group that the Board, by the affirmative vote of at least seventy-five percent (75%) of the entire Board, may exempt from the provisions of this clause.

The limitations set forth above do not apply to any Shareholder which is a “Byrne Entity” (as defined below) for any matter submitted to the vote of Shareholders, except with respect to the election of directors.  “Byrne Entity” means any foundation or trust established by John J. Byrne, Patrick Byrne, and any associate or affiliate of any of them (or any group of which any of them is a part), as defined under Section 13(d) of the United States Securities Exchange Act of 1934, as amended.

If, as a result of giving effect to the foregoing provisions or otherwise, the votes conferred by the Controlled common shares of any person would otherwise represent 10% or more of the votes conferred by all the outstanding common shares, the votes conferred by the Controlled common shares of such person shall be reduced in accordance with the foregoing provisions.  Such process shall be repeated until the votes conferred by the Controlled common shares of each person represent less than 10% of the votes conferred by all common shares.

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Voting Rights of Members

As of April 2, 2018, there were 3,753,405 common shares outstanding.  Members of record of common shares shall be entitled to one vote per common share, provided that if, and so long as, the votes conferred by “Controlled” common shares (as defined below) of any person constitute ten percent (10%) or more of the votes conferred by the outstanding common shares of the Company, each outstanding common share comprised in such Controlled common shares shall confer only a fraction of a vote that would otherwise be applicable according to the following formula:

[(T divided by 10)-1] divided by C

Where: “T” is the aggregate number of votes conferred by all the outstanding common shares; and “C” is the number of votes conferred by the Controlled common shares of such person.

“Controlled” common shares in reference to any person means:

(1)all common shares directly, indirectly, or constructively owned by such person within the meaning of Section 958 of the Internal Revenue Code of 1986, as amended, of the United States; and

(2)all common shares directly, indirectly, or constructively owned by any person or “group” of persons within the meaning of Section 13(d)(3) of the Exchange Act and the rules and regulations promulgated thereunder; provided that this clause (ii) shall not apply to (a) any person (or any group that includes any person) that has been exempted from the provisions of this clause or (b) any person or group that the Board, by the affirmative vote of at least seventy-five percent (75%) of the entire Board, may exempt from the provisions of this clause.

The limitations set forth above do not apply to any Member which is a “Byrne Entity” (as defined below) for any matter submitted to the vote of Members, except with respect to the election of directors.  “Byrne Entity” means any of John J. Byrne, any foundation or trust established by John J. Byrne, Patrick Byrne, and any associate or affiliate of any of them (or any group of which any of them is a part), as defined under Section 13(d) of the United States Securities Exchange Act of 1934, as amended.

If, as a result of giving effect to the foregoing provisions or otherwise, the votes conferred by the Controlled common shares of any person would otherwise represent 10% or more of the votes conferred by all the outstanding common shares, the votes conferred by the Controlled common shares of such person shall be reduced in accordance with the foregoing provisions.  Such process shall be repeated until the votes conferred by the Controlled common shares of each person represent less than 10% of the votes conferred by all common shares.

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(b)   The common shares shown as beneficially owned by (1) Mr. Barrette and (2) all directors, Named Executive Officers and all other executive officers as a group represent 1.0% and 4.0% of the total common shares outstanding at April 2, 2018, respectively.  No other director or executive officer beneficially owned 1% or more of the total common shares outstanding at that date.  Beneficial ownership has been determined in accordance with Rule 13d-3 of the Exchange Act.

(c)   Common shares shown as economically owned include common shares beneficially owned and target unearned performance share awards, less any common shares in which the owner disclaims a pecuniary interest.

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Compensation Discussion and Analysis

Executive Summary

Business Overview and 2019 Performance Highlights

White Mountains is engaged in the business of making opportunistic and value-oriented acquisitions of businesses and assets in the insurance, financial services and related sectors, operating those businesses and assets through its subsidiaries and, if and when attractive exit valuations become available, divesting to realize gains on their sale. Our principal focus is to grow adjusted book value per share (“ABVPS”) because we believe that, over the long term, our share price growth will parallel our growth in ABVPS (see chart and discussion on page 30). Since our IPO, including dividends, White Mountains has delivered 13% annualized growth in ABVPS and 12% annualized growth in market value per share. Having sold off a number of significant businesses from 2015-2017, which generated $1.4 billion in transaction gains and left us with $3.1 billion of pro forma undeployed capital, we remain in a transitional period as we continue to work to thoughtfully redeploy and distribute the proceeds of those transactions.

2019 was a strong year for our Company driven by good operating results in our main businesses and strong absolute investment returns, which led to a strong one-year total shareholder return of 30.2%.  Excluding the gain from the MediaAlpha transaction in February 2019, we grew ABVPS by 8.1% and our total investment portfolio returned 15.5%.

In 2019, we redeployed $435 million into businesses, following $332 million in capital deployments in 2018, and we ended the year with undeployed capital of $1.0 billion.  We expect our returns to continue to normalize and revenues to grow as we finish redeploying and distributing this capital.

Commitment to Ongoing Shareholder Engagement

As part of our ongoing commitment to better understand the views of our shareholders with respect to our business, governance, and compensation practices, we have continued our investor outreach efforts in 2019.  Over the past several years, feedback received from these discussions has helped guide refinements to our executive compensation programs and governance practices, as well as enhancements to our public disclosure.  A summary of these efforts in 2019, feedback received and responsiveness is below:

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The Right Compensation Peer Group

As described in more detail below, the CNG Committee refers to a peer group as part of its evaluation of the Company’s compensation practices.  Importantly, we do not use this peer group to benchmark compensation.   Rather, we evaluate the executive compensation programs of these peers in terms of structure and variability of payouts in good and poor performance scenarios. We seek to structure our compensation program to be more variable than most other insurance and reinsurance peers.  The CNG Committee believes that our compensation structures closely align the financial interests of management with those of our shareholders and encourage appropriate, but not excessive, risk taking.

We have made meaningful progress in redeploying and distributing the proceeds from our sale transactions in recent years.  However, as we continue to have $1 billion of undeployed capital, our returns are not comparable to peers who are fully deployed, and pay level benchmarking comparisons to any peer group, including our own, are not meaningful at this time. The CNG Committee regularly evaluates the continuing appropriateness of our peer group and will revisit our peer group as we continue to redeploy capital. See page 29 for further details on our 2019 peer group.

Compensation Program Aligned with Company Performance

In assessing the design of our executive compensation program, we value input from our shareholders and incorporate their feedback into our assessment. The current design of our compensation program consists of three primary elements: base salary, annual incentive bonus and long-term incentive compensation. Each element isstructured with the primary goal of maximizing shareholder value over long periods of time. Highlights of our 2019 compensation program are as follows:

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Elements and Structure

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We believe that the goal of maximizing shareholder value over long periods of time is best pursued by utilizing a pay-for-performance program that closely aligns the financial interest of management with those of our shareholders while rewarding appropriate risk taking. We accomplish this by emphasizing variable long-term compensation, the value of which is tied to performance over a number of years rather than fixed entitlements. To illustrate, 86% of our CEO’s 2019 target total direct compensation was linked to long-term incentives, while 8% was made up of base salary, and 6% linked to annual cash bonus opportunity at target.

Chief Executive Officer:

Other NEOs:

Named Executive Officers

In this CD&A, we review the philosophy of White Mountains’s executive compensation program, the compensation process, the program’s elements, and the 20172019 and 20182020 compensation decisions for our current named executive officers:

·    Manning Rountree, CEO as of March 1, 2017

·    Reid Campbell, EVP and CFO as of May 17, 2017

·    Robert Seelig, EVP and General Counsel

·    Brian Palmer, Managing Director and CAO

In addition, under applicable SEC rules, we also are required to discuss the 2017 compensation decisions for the following former named executive officers:

·    Ray Barrette, former Chairman and CEO, who served through March 1, 2017

·    David Foy, former CFO, who served through May 16, 2017 and remained an employee until December 31, 2017

·    David Linker, former President of WM Advisors, who served through November 2017 and remained an employee until January 31, 2018

·    Michael Miller, CEO of OneBeacon, who ceased to be an executive officer of White Mountains upon the closing of the sale of OneBeacon on September 28, 2017

2019 Named Executive Officers
G. Manning Rountree	Chief Executive Officer
Reid T. Campbell	Executive Vice President &Chief Financial Officer
Frank R. Bazos	Executive Vice President &Head of Mergers &Acquisitions of WM Capital
Robert L. Seelig	Executive Vice President &General Counsel
J. Brian Palmer	Managing Director &Chief Accounting Officer

Unless otherwise noted, the term named executive officer as usedofficers (or “NEOs”) refers to the group of the five individuals listed in this CD&A does not include Messrs. Barrette, Foy, Linker and Miller,above table, the term “CEO” refers to Mr. Rountree, the term “CFO” refers to Mr. Campbell, and the term “Committee”“CNG Committee” refers to the CompensationCompensation/Nominating & Governance Committee of the Board of Directors of White Mountains.

BackgroundBusiness Overview, Significant Transactions in 2015-2017 and Performance Highlights

White Mountains is engaged in the business of making opportunistic and value-oriented acquisitions of businesses and assets in the insurance, financial services and related sectors, operating these businesses and assets through ourits subsidiaries and, if and when attractive exit valuations become available, disposingdivesting to realize gains on the sale of these businesses and assets.

In recent years,From 2015-2017, White Mountains has sold a number of its businesses—OneBeacon,Sirius, Symetra, Tranzact Sirius and Symetra—OneBeacon—as buyers made compelling offers that resulted in roughly $1.4 billion of transaction gains thatand drove strong growth in adjusted book value per share (“ABVPS”) during 2015-2017.ABVPS.  As a result of these sales, the Company finds itselfis in a transitional period of transition as management works to intelligently redeploy and distribute the transaction proceeds.  Pro forma for the OneBeacon sale, asAs of May 2017, on a pro forma basis for theOneBeacon sale, the Company had an undeployed capital position of $3.1 billion on a capital base of $4.2 billion.  In addition, after the Company’s remaining businessessales, the Company generated much lower revenues than before the sold businesses,sales, and the high level of undeployed capital impliesimplied a low single digit go-forward rate of growth in ABVPS, at least in the short term. WeABVPS. As undeployed capital continues to be deployed or distributed, we expect returns to normalize and revenues to grow over several years, asgrow.

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In 2019, we continued to make good progress and deployed $435 million.  Three significant deals emerged from our platform companies: (i) Embrace, a pet insurance MGA acquired by NSM, (ii) the acquisition of NSM’s collector car renewal rights and (iii) our buyout of Oaktree’s 50% interest in Kudu.  As of December 31, 2019, undeployed capital is deployedwas down to $1.0 billion. In 2019, excluding the gain from the early 2019 MediaAlpha transaction, ABVPS and CVPS grew by 8.1% and 9.1%, respectively.  These results outperformed their respective targets for the year, which were set rigorously by the CNG Committee above the prior period targets.  In addition, for the 2017-2019 performance cycle, the average annual growth in new opportunities or distributed.  ABVPS and CVPS was 8.9% and 7.9%, respectively.

The Company remains focused on economics and creating shareholder value, while targeting redeployment in its areas of expertise: primarily insurance, broader financial services and adjacent sectors.  The Company remains value-oriented, opportunistic and highly flexible.

In making compensation grants in early 2018Shareholder Engagement and setting related performance targets, the Committee took account of the stage of transition of the Company, including the level of deployed and undeployed capital and the expected run rate returns thereon, and made assumptions regarding the timing and magnitude of redeployment and distributions consistent with the Company’s communications with shareholders in May 2017.  In particular, for the new incentive grants, which were the first grants made after the completion of all the aforementioned sales, the Committee decreased the total target number of shares granted under the long-term incentive plan by roughly 24% and increased the performance target applicable to the new performance share cycle by 1 point over the prior cycle.  In addition, the Committee considered the feedback received from owners through the Company’s shareholder outreach conducted in May 2017 and the vote levels from the 2017 “say-on-pay” proposal. The Committee will strongly consider the feedback and vote levels when determining the appropriateness and amounts of any future separation payments to executives.  The Committee has determined that separation payments relating to periods after the date of separation generally will be limited to no more than target levels.

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base salaries and target annual bonuses for our executives that tend to be lower than those paid by comparable property and casualty insurers and reinsurers, while granting the bulk of an executive’s target compensation as long-term incentive compensation.  To illustrate, 86% of our CEO’s 2019 target total direct compensation was linked to long-term incentives, while 8% was made up of base salary and 6% was target annual cash bonus opportunity.

The following principles guide and inform the CNG Committee’s efforts to deliver a highly effective executive compensation program that drives shareholder value and fosters the attraction and motivation of key talent:

Compensation Setting Process

The CNG Committee is responsible for approving our compensation programs for executive officers, and it specifically approves all compensation for our executive officers and for any employee with target annual compensation in excess of $1.5 million.  Our CEO annually presents to the CNG Committee his evaluation of our executives, their individual performance, achievements, and the contributions they made to the Company’s accomplishments over the past year, as well as over the most recent long-term incentive plan cycle.  In connection with this evaluation, the CEO recommends to the CNG Committee appropriate compensation amounts for these executives.  The CNG Committee assesses the performance, responsibilities and contributions of the CEO, considers CEO succession plans, and sets the compensation of the CEO.

We generally have structured ourWith the exception of significant promotions and new hires, compensation matters are usually addressed at the first meeting of the CNG Committee each year (typically late February), following the availability of financial results for the prior year and the current year’s financial plan.  This allows us to determine the results of prior period grantsand to set targets for the current year and newest long-term incentiveperformance cycle.  Performance cycles for long-term compensation as performance shares and restricted shares, which reward company-wide performance.  The numbertypically run for three years beginning on January 1st of WTM common shares earned from a grantthe year of performance shares can be from 0x to 2x the target number granted.  The metric we use to measure performance is our after-tax annual growth in compensation value per share over the performance cycle (“CVPS”, which is defined by the Committee as the average of growth in ABVPS and growth in “intrinsic business value per share”, which is the ABVPS including franchise value and certain other adjustments).  The market value of our shares is not included as a measure of performance, but it determines the value of performance and restricted share awards.  The Committee focuses on performance metrics that relate to growth in book value per share because it believes these are the best metrics for valuing insurance and reinsurance companies.  As Benjamin Graham said in his famous quote: “In the short run, the market is a voting machine, but in the long run it is a weighing machine.”grant.

Performance shares and restricted shares typically are granted annually, and performance is tied to a three-year period.  Under our long-term incentive programs, at any given time an executive usually has three overlapping cycles running.  This approach avoids cliffs that could foster a short-term outlook and also serves as an effective retention tool.

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The companies included in the analysis presented to the CNG Committee prior to it making compensation decisions in 20182019 were:

The Company uses this group of companies as it reflects traditional competitors of White Mountains.  The CNG Committee regularly evaluates the continuing appropriateness of this groupgroup.  Even though sales transactions over the past five years temporarily lowered our go-forward revenues and although the Company is going through a period of transitionnear-term growth in ABVPS expectations, our strategy remains intact as management workswe look to redeploy and distributeour capital.  Therefore, the sales proceeds, theCNG Committee believes this group currently remains appropriate.  appropriate for the Company’s competitive analysis, as a temporary reduction in revenues following significantly value-generating asset sales is not an appropriate catalyst for what would be an interim peer group change at this time.

The CNG Committee concluded that the peer analysis supported its view that the Company’s compensation programs are appropriately sized and more variable than most other insurers,insurance and reinsurance peers, have fewer fixed elements of compensation and perquisites, and do not lead to significant rewards for poor performance.

To measure value sharing, in light of the significant sales of businesses over the past couple of years, the amount of undeployed capital, and the resulting change in the profile of the Company, the Committee has begun focusing on run rate “at target” compensation expense relative to the capital base.  In 2015, 2016 and 2017, the at target run rate compensation expense was 1.3%, 1.4% and 1.6% of total capital.  Despite the substantial shrink in the capital base as a result of the return of over $1.6 billion to shareholders in 2016 and 2017, the 2018 run rate expense is back down to 1.3% of total capital as the Company has aggressively managed total compensation expense while working to redeploy the proceeds of the sale transactions.

The CNG Committee believes that the compensation structures that have been developed for the Company closely align the financial interests of management with those of our shareholders and encourage appropriate, but not excessive, risk taking.

Our Compensation ProcessBest Practices

The Committee is responsible for approvingWe maintain a number of compensation governance best practices which support our overarching compensation philosophy and are fully aligned with our compensation principles, as discussed in the following section. Our compensation practices that affect executive officers, and it specifically approves all compensation for our executive officers and for any employeealso align with target annual compensation in excess of $1.5 million.  Our CEO annually presents the Committee with his evaluation of our executives, their individual performances, responsibilities, and the contributions they made to the Company’s accomplishments over the past year, as well as over the last long-term incentive plan cycle and his expectations for the future and succession plans.  In connection with this evaluation, the CEO presents the Committee with his recommendations for establishing the compensation for these executives for its consideration.  The Committee assesses the performance, responsibilities, and contributions of the CEO, considers CEO succession plans, and sets the compensation of the CEO.

.  Because Mr. Tolman did not satisfy certain requirementsTable of Section 162(m) to be considered an “outside director” for purposes of that rule, the Committee formed the Performance Compensation Subcommittee (the “Subcommittee”) comprised of the other members of the Committee, each of whom met the requirements to be considered an outside director for purposes of Section 162(m).  The Subcommittee administers and approves all performance-based compensation awards made prior to the enactment of the Tax Cuts and Jobs Act of 2017 (the “TCJA”) in order to maintain favorable tax treatment of such awards to the extent applicable. However, the Company may establish compensation that is not tax deductible if in the Committee or Subcommittee’s judgment doing so better promotes its objectives.  Further, as a Bermuda-domiciled company, we do not receive a tax deduction for compensation paid to employees of White Mountains Insurance Group, Ltd. and, accordingly, the limitation of Section 162(m) does not impact compensation paid to our named executive officers who are employees of non-U.S. companies. With the elimination of the performance-based compensation exception from the limits of Section 162(m) under the TCJA, the Committee will administer and approve compensation grants made in 2018 and beyond.Contents

Significant Corporate TransactionsSuperior Track Record and the Alignment of Growth in 2017ABVPS and During the 2015-2017 Long-term Incentive CycleMarket Value Per Share

OverFrom our IPO in 1985 through year-end 2019, we have delivered 13% annualized growth in ABVPS and 12% annualized growth in market value per share to our shareholders.  Importantly, as seen in the coursechart below, ABVPS and market value per share have generally moved in tandem over the last thirty-five years, despite short-term fluctuations.  This is a core reasoning behind the CNG Committee’s selection of the 2015-2017incentive plan performance cycle, White Mountains sold its interestmetrics that relate to growth in four major businesses generating $1.4 billion of transaction gains.  Over the three-year period, ABVPS grew from $664 to $915, representing an annualized ROE of 11.4%, including dividends. In 2017, ABVPS grew from $789 to $915, an ROE of 16.1%, including dividends.book value per share.

In 2017, OneBeacon agreed to be acquired by Intact Financial for $1.7 billion, or 1.7x book value.  In exchange for our 76% stake, we received cash proceeds of about $1.3 billion and recorded an after-tax gain of $555 million.  Over the 16 years from acquisition to sale, White Mountains’s returns on the OneBeacon investment were a 14% after-tax IRR (vs. an S&P 500 annual total return of 6%) and a 2.5 multiple of invested capital.  With the timing and structure of the transaction, we avoided the significant catastrophe losses resulting from the difficult Atlantic hurricane season and the other natural catastrophes experienced by most other insurers and reinsurers.

In 2016, White Mountains sold Tranzact after a 20-month hold generating an $82 million after-tax gain in adjusted book value ($16 per share) and a 35% IRR.30

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In 2015, White Mountains agreed to sell its reinsurance business, Sirius Group, to China Minsheng Investments for approximately $2.6 billion.  The transaction closed in 2016, and White Mountains recorded a total after-tax gain on the sale of $477 million. Over White Mountains’s 20-year history with its reinsurance business, we managed to produce an after-tax IRR of 11%.

Also in 2015, Symetra Financial agreed to be sold to Sumitomo Life.  White Mountains recorded a total after-tax gain relating to the sale of $270 million and generated a 15% IRR over its 11-year ownership period, more than double the S&P 500 return over during that time.

These four transactions generated total proceeds of $4.2 billion and resulted in undeployed capital of roughly $3.1 billion at May 2017 pro forma for the OneBeacon transaction.  As discussed with shareholders through an investor presentation and meetings in May 2017, management expects to shrink the Company over the medium term by distributing $1.5 billion to $2 billion of undeployed capital.  To that end, in 2017 the Company returned $724 million to owners while reducing outstanding shares by 832,725.  In addition, management is seeking to deploy $200 million annually in new opportunities, though we expect these deployments to be lumpy.  In 2017, approximately $275 million was deployed in/committed to new business opportunities. In total, about $1.0 billion was returned or deployed, bringing year-end undeployed capital to $2.1 billion.

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2.            Annual Incentive Bonuses

We provide annual bonus opportunities to our executive officers.officers, which make up a small percentage of each NEO’s target total annual compensation – 6% for our CEO, and 11% on average for the other NEOs in 2019 – as the bulk of our executive officers’ compensation opportunity is tied to long-term incentives.  Each Named Executive Officer participates in the annual bonus pool applicable to the parent holding companies.  For 2017,2019, the target bonus pool was $4.2$5.6 million for 3842 employees.

Following the 2018 annual general meeting, the Company’s management team, along with CNG Committee chair Edith Holiday, who participated in a significant portion of the meetings, engaged with shareholders representing approximately 50% of our outstanding shares.  Based on those discussions and as a direct response to feedback, the CNG Committee has introduced a formulaic annual incentive program in effect for 2019 for our executive officers, with pre-established, rigorous, quantifiable performance targets relevant for our firm and industry.

Under our quantitative annual bonus program, the level of payout is determined by reference to the Company’s growth in CVPS, which is defined by the CNG Committee as the average of growth in ABVPS and growth in “intrinsic business value per share,” which is the ABVPS including franchise value step-ups to reflect the fair value of certain subsidiaries carried at book value.  In choosing this metric for the annual bonus program, the CNG Committee recognized that this is the same metric as used in a portion of the Company’s long-term incentives (albeit for a different time period).  The awarded bonus pool size can rangeCNG Committee considered a number of other metrics but concluded that no other metric is as pertinent to our business as CVPS.  CVPS is the metric that the Board and the management team focus on because it is linked to growth in book value per share metrics, which we believe is what ultimately drives growth in our share price for our shareholders.  As previously disclosed in our 2019 proxy statement, 2019 annual bonuses were eligible to be earned ranging from 0% to 200% of target, depending upon performance.  Individual bonuses can vary widely aroundaccording to the pool average based on individual performance and no cap (other than the sizeharvest scale of the pool) applies to any single individual2%-7%-12%.

For the Named Executive Officers, the annual incentive bonus is designed to reward company-wide performance and the individual NEO’s contributions to those results.  The Committee did not set a quantitative target in 2017 and instead established the size of the awarded pool based on a qualitative assessment of the Company’s performance during the year based on its judgment.  The Committee believes that using a qualitative assessment rather than a quantitative target for the Company’s annual bonus is appropriate given that the Company seeks to maximize shareholder value over long periods of time, whereas quantitative results over a one-year period do not necessarily provide a full picture of the performance of the Company.  In addition, and reflecting this, annual bonus opportunity reflects a small proportion of the total compensation opportunity of our executive officers, (e.g., less than 10% of the total compensation opportunity inCNG Committee maintains the case of our CEO and EVPs), withdiscretion to decrease the bulk of ourindividual annual bonus payouts after the quantitative formula has been applied, however it does not have discretion to increase payouts.  Our executive officers’ compensation opportunity tied to long-term incentives. officers, at most, receive the quantitative result.

For 2017,2019, the Named Executive Officers had target annual bonuses of 75% of salary, which was unchanged from the prior year.

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The CNG Committee selected performance metrics that relate to growth in book value per share because it continues to believe these metrics ultimately drive growth in our share price for our shareholders.  The market value of our shares is not included as a direct measure of performance, but it determines the ultimate value of earned performance and restricted share awards.

From year-to-year when we make new long-term incentive grants, we typically adjust the target number of shares granted to individual employees to reflect the change in CVPS during the prior year, rather than focusing on changes in market values.  This is consistent with our view that the change in book value per share and related metrics provides a better view of the change in value of the Company than metrics reflecting short-term market price fluctuations.  In addition, we generally limit total annual share grants to employees to equal to or less than 1% of the Company’s outstanding shares.  For each of the 2017-2019, 2018-2020, 2019-2021, and 2020-2022 cycles, we adhered to this guideline.

New Grants for the 2017-2019 Performance Cyclein 2019:.  For the CEO and each named executive officer recipient of aour other NEOs, the annual 2019 long-term incentive grant for the 2017-2019 performance cycle, the new grantsawards were allocated 50% as performance shares and 50% as restricted shares, which generally wasconsistent with prior years.  The restricted shares are subject to a three-year cliff vesting provision based on continuous service, in order to promote retention of key executive talent.  The performance shares will vest in a range of 0% - 200% of target, following a three-year performance period.

For the same allocation as in 2016.  The Subcommittee2019-2021 performance period, the CNG Committee established a target of 5%7% annual growth in CVPS as the performance target that would result in the payout of 100% of the target performance shares.  AnnualThere would be no payout for annual growth of 1%2% or less, would result in a payout of 0%, and annual growth of 9%12% or more would result inbe required for a payout of 200%.  Importantly, the target and maximum goals for the 2019-2021 performance cycle (2%-7%-12%) were set higher than the previous 2018-2020 cycle (2%-6%-10%), which in turn were set higher than the previous 2017-2019 cycle (1%-5%-9%).  In setting this performance scale, a primary goal of the SubcommitteeCNG Committee was to set a performance target that would incentivize management to redeploy capital thoughtfully.  The CNG Committee took account of the level of deployed and undeployed capital (and the expected run rate returns thereon) and made assumptions regarding the timing and magnitude of redeploymentfuture deployment and distributions of undeployed capital consistent withcapital.  In addition, the Company’s communications with shareholders in May 2017.CNG Committee considered that the one-year performance scale for the 2019 annual bonus program was the same as the three-year average performance scale being set for the 2019-2021 performance shares.  The Committee determined that this scale was appropriate due to the factors discussed above and their applicability over a longer time frame (which equates to aggregate growth of 6%-23%-40% over a three-year period).

In total, the WTM performance share and restricted share grants made to all employeesA detailed breakdown of the Company forfiscal 2019 grants are included in the 2017-2019 performance cycle totaled approximately 0.8% of the then outstanding shares, within the Committee’s 1% guideline.table below:

CEO.  Mr. Rountree became CEO of the Company on March 1, 2017.  Previously, Mr. Rountree served as EVP of the Company and President of WM Capital.  Mr. Rountree’s promotion to CEO occurred at the same time as the board meeting at which compensation decisions for the year were made.  After reviewing Mr. Rountree’s historical compensation, his share ownership, his existing incentives, compensation granted to CEOs at other property and casualty (re)insurance companies, and the historical run rate compensation level of WTM’s CEO (i.e., in 2015 and prior, which was before the former CEO’s 2016 compensation package was reduced as he moved toward retirement), the Subcommittee determined to grant him 2,900 target performance shares and 2,900 restricted shares for the 2017-2019 performance cycle.  The grant date market value was approximately $5.5 million.  The number of performance shares that will be earned will be determined after the end of 2019 based on the Company’s performance over the cycle compared to the target described above.  The 2017-2019 restricted shares will vest on January 1, 2020, subject to Mr. Rountree’s continued employment.

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in ano payout of 0% and annual growth of 14%9% or more would have resulted in a payout of 200%. At its meeting in March 2018,February 2020, based on an average annual growth in CVPS of 10.7%7.9%, the Performance Compensation Subcommittee confirmed that the payout that was earned was 145%174% of target.