DEF 14A of White Mountains Insurance Group LTD, Apr 1, 2026

DEF 14A of White Mountains Insurance Group LTD

Filed Apr 1, 2026 · FY20250001104659-26-038487

Open on EDGAR
  1. Board of Directors

    Board of Directors

  2. Class I –Term Ending in 2028

    Class I –Term Ending in 2028

  3. Class I –Term Ending in 2028

    | Reid T. Campbell | Qualifications | | ● Joined in 2024 ● Age: 58 ● Committee: Finance | Experience: ● President of White Mountains Insurance Group, Ltd. from 2022 to February 2024 ● Prior to being named President, served as Chief Financial Officer of White Mountains from 2017 to 2022 ● President of White Mountains Advisors from 2015 to 2017 ● Held a variety of financial management positions with White Mountains and its subsidiaries from 1994 to 2015 ● Prior to joining White Mountains, spent three years with KPMG Mr. Campbell has extensive financial and management expertise gained over the course of his more than 30-year career in the insurance and financial services industries. Select Board Service: ● Build America Mutual Assurance Co. (Private) ● Ark Insurance Holdings Limited (Private) |

  4. Class I –Term Ending in 2028

    | Peter M. Carlson | Qualifications | | ● Joined in 2019 ● Age: 61 ● Committees: Audit (Chair), Executive | Experience: ● Chief Executive Officer of Spectral AI, Inc., an artificial intelligence (AI) company focused on medical diagnostics, from February to October 2024 ● Chief Financial Officer of Spectral AI, Inc., from January 2024 to February 2024 ● Chief Financial Officer of MiMedx Group, a biopharmaceutical company, from 2019 to 2023 ● Executive Vice President and Chief Operating Officer of Brighthouse Financial, a U.S. annuity and life insurance company that spun off from MetLife, from 2017 to 2018 ● Executive Vice President and Chief Accounting Officer at MetLife from 2009 to 2017 ● Formerly at Wachovia Corporation from 2002 to 2009, where he served as Executive Vice President and Corporate Controller from 2006 to 2008 ● Joined Wachovia after fifteen years at Arthur Andersen, where he served as an audit partner working in financial services, manufacturing, commercial services and distribution ● Serves as a Trustee of Wake Forest University and National Philanthropic Trust Mr. Carlson has extensive accounting and auditing experience gained over the course of his more than 30-year career in the insurance and financial services industries. Select Board Service: ● Citizens, Inc. – Audit Committee (Public) |

  5. Class I –Term Ending in 2028

    | Suzanne F. Shank | Qualifications | | ● Joined in 2021 ● Age: 64 ● Committees: Compensation/Nominating & Governance, Finance | Experience: ● President, CEO and co-founder of Siebert Williams Shank & Co., LLC (formerly Siebert Cisneros Shank & Co., LLC), a full service investment banking and financial services company established in 1996 ● Prior to her financial services career, she worked as a structural engineer at General Dynamics Corporation ● Serves as Board Member of Skillman Foundation, Kresge Foundation and Spelman College Ms. Shank has extensive experience in investment banking and municipal finance gained over the course of almost 35 years in the financial services industry Select Board Service: ● Consumers Energy Company - Audit Committee (Public) ● Rocket Companies, Inc. - Audit Committee (Public) |

  6. Class II –To Be Elected to a Term Ending in 2029

    Class II –To Be Elected to a Term Ending in 2029

  7. Class II –To Be Elected to a Term Ending in 2029

    | Liam P. Caffrey | Qualifications | | ● Joined in 2026 ● Age: 53 ● Committees: Finance, Executive | Experience: ● Joined White Mountains in 2022 ● Prior to CEO appointment in 2026, served as President & Chief Financial Officer of White Mountains Insurance Group, Ltd. from 2024-2025 ● Prior to being named President, served as Executive Vice President & Chief Financial Officer of White Mountains from 2022 to 2024 ● CEO of Aon’s Global Affinity Business from 2018 to 2020 ● Chief Financial Officer of Aon Risk Solutions from 2015 to 2018 ● Chief Financial Officer of Aon Risk Solutions Americas from 2012 to 2015 ● Principal at McKinsey & Company prior to joining Aon Mr. Caffrey has extensive management and financial expertise gained over the course of his career in the insurance and financial services industries. Select Board Service: ● Various WTM portfolio companies (Private) |

  8. Class II –To Be Elected to a Term Ending in 2029

    | Mary C. Choksi | Qualifications | | ● Joined in 2017 ● Age: 75 ● Committees: Finance (Chair), Executive | Experience: ● Founding Partner (and Senior Managing Director/Senior Advisor until February 2017) of Strategic Investment Group, an investment management enterprise founded in 1987 which designs and implements global investment strategies for institutional and individual investors ● Founder and Managing Director of Emerging Markets Management LLC until May 2011 ● Prior to 1987, worked in the Pension Investment Division of the World Bank ● Served as a director of Avis Budget Group from 2007 to 2020 Ms. Choksi has extensive executive and board-level service and investment management expertise gained over the course of over 40 years in the financial services industry. Select Board Service: ● Omnicom Group – Lead Independent Director, Audit (Chair) and Compensation Committees (Public) ● Franklin Templeton Mutual Funds (24 investment companies) - Audit Committee |

  9. Class II –To Be Elected to a Term Ending in 2029

    | John K. Chu | Qualifications | | ● Nominee for election in 2026 ● Age: 62 | Experience: ● Founder and CEO of Bamboo Insurance since 2018 ● Prior to Bamboo, served as Chairman and CEO of The McGraw Group from 2014 to 2017 ● Operating Partner at Altamont Capital Partners from 2011 to 2014 ● Operating Partner at Golden Gate Capital from 2009 to 2011 ● Senior Vice President, eBusiness & Technology at The Hartford from 2003 to 2008 ● Prior to his role as SVP, served as Chief Financial Officer, Personal Lines at The Hartford from 1999 to 2003 ● Managing Consultant at Tillinghast Tower-Perrin from 1995 to 1999 Mr. Chu has extensive expertise in the insurance and investments industries gained over the course of more than 25 years in the insurance and financial services industries. |

  10. Class II –To Be Elected to a Term Ending in 2029

    | Weston M. Hicks | Qualifications | | ● Joined in 2023 ● Age: 69 ● Chairman of the Board ● Committees: Audit, Executive (Chair) | Experience: ● Appointed Chairman of the Board in May 2023 ● President & CEO of Alleghany Corporation from 2004 to 2021 ● Executive Vice President for Alleghany Corporation from 2002 to 2004 ● Executive Vice President and Chief Financial Officer for The Chubb Corporation from 2001 to 2002 ● Senior Research Analyst for J.P. Morgan Securities from 1999 to 2001 ● Senior Research Analyst for Sanford C. Bernstein from 1991 to 1999 ● Associate Director, Moody’s Investor Service from 1986 to 1991 ● Prior to 1986, Mr. Hicks had several years of experience in the banking and accounting industry ● Served as a director of Alleghany Corporation from 2004 to 2021 Mr. Hicks has extensive experience in finance, insurance, investment management, private equity and executive management gained over the course of over 40 years in the insurance and financial services industries. |

  11. Class III – Term Ending in 2027

    Class III – Term Ending in 2027

  12. Class III – Term Ending in 2027

    | Margaret Dillon | Qualifications | | ● Joined in 2021 ● Age: 66 ● Committees: Audit, Compensation/Nominating & Governance | Experience: ● Served as Executive Vice President and Chief Customer Officer, US Consumer Markets, for Liberty Mutual Insurance Company from 2014 to 2017 ● Senior Vice President and Chief Financial Officer, Personal Lines Insurance, for Liberty Mutual Insurance Company from 2002 to 2014 ● Controller, Personal Markets, for Liberty Mutual Insurance Company from 1998 to 2001 ● Served in various technology and finance roles for International Paper from 1984 to 1993 Ms. Dillon has extensive executive, financial, and property and casualty insurance expertise gained over the course of over 30 years in the insurance and manufacturing industries. Select Board Service: ● Guidewire Software - Audit Committee (Public) |

  13. Class III – Term Ending in 2027

    | Philip A. Gelston | Qualifications | | ● Joined in 2018 ● Age: 73 ● Committees: Audit, Compensation/Nominating & Governance (Chair), Executive | Experience: ● Joined Cravath, Swaine & Moore LLP in 1978, became a partner in 1984, and retired in December 2017 ● Currently advises Cravath regarding governance, risk management, professional responsibility requirements and compliance issues ● Has extensive experience in mergers and acquisitions, joint ventures and general corporate counseling, encompassing complicated negotiated transactions, hostile transactions (both offense and defense), cross border transactions, activist defense, and advising boards and senior executives, particularly on complex transactions, corporate governance and managing crisis situations ● Serves as a Trustee for the Friends of Democracy Prep New York Charter Schools Mr. Gelston has extensive legal and management expertise gained over the course of his 40-year career in the legal field. |

  14. Class III – Term Ending in 2027

    | David A. Tanner | Qualifications | | ● Joined in 2018 ● Age: 67 ● Deputy Chairman of the Board ● Committees: Audit, Finance | Experience: ● Appointed Deputy Chairman of the Board in February 2020 ● Managing Director of Three Mile Capital LLC, a private investment company ● Served as the Managing Director of Arlon Group LLC and as Executive Vice President and a member of the Management Committee of Continental Grain Company from 2006 to 2017 ● Founder and Managing Principal of Quadrangle Group, LLC from 2000 to 2006 ● Managing Director at Lazard Freres & Co. and Managing Principal at Lazard Capital Partners from 1998 to 2000 ● Serves as Chairman of the Board of the New York University School of Law, Trustee of New York University, Director of Lawyers for Children, Director of The Carroll and Milton Petrie Foundation, Trustee of Central Synagogue, Director of The Health Initiative and a member of the Council on Foreign Relations Mr. Tanner has extensive executive and board-level service and financial expertise gained over the course of almost 40 years in the financial services industry. Select Board Service: ● Northeast Bancorp (Public) |

  15. Class III – Term Ending in 2027

    CORPORATE GOVERNANCE We are committed to the ethical conduct of our business. This commitment is reflected in our corporate governance and in our corporate values and culture. Our corporate governance helps us to mitigate and manage risks by providing clear lines of oversight and responsibility for management and the Board. We review and seek to improve our corporate governance regularly. The Company’s Corporate Governance Guidelines spell out our 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 2025. The Company’s Corporate Governance Guidelines and Code of Business Conduct are available on our website, www.whitemountains.com. These documents are available in print, free of charge, to any shareholder upon request.

  16. Consideration of Director Nominees

    Consideration of Director Nominees General Criteria and Process for Selection of Director Candidates. Our Compensation/Nominating & Governance Committee regularly reviews the individual and collective skills and other attributes of Board members. 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 business and life experience, knowledge about the Company’s business and industry and ownership interest in the Company. 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. The Compensation/Nominating & Governance Committee has the authority to retain search firms to be used to identify director candidates. We inform any director search firm that may be retained of our preference to include highly qualified candidates who have diverse identities or backgrounds in the pool of potential candidates it presents for consideration by the Board. Consideration of Diversity in Selection of Director Candidates. We believe that a variety of perspectives, opinions, backgrounds, business and life experiences and tenure among the members of the Board enhances the Board’s ability to perform its duties and effectively oversee the Company’s business. In the selection of director candidates, we welcome a diversity of skills, backgrounds, business and life experiences, identities and viewpoints. 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 Corporate 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.

  17. Compensation Peer Group

    Compensation Peer Group As described in more detail below, the CNG Committee reviews the compensation structures of a peer group as part of its evaluation of the Company’s compensation practices, but not for benchmarking compensation levels. As many of our subsidiaries are engaged in the business of insurance, we evaluate the executive compensation programs of a group of insurance company peers in terms of structure and variability of payouts in good and poor performance scenarios. However, unlike most of our insurance company peers, a primary responsibility of our parent company’s management is allocating capital and opportunistically finding and executing value-creating acquisitions and dispositions of operating businesses. Over the years, transaction gains have been a large driver of success in achieving our principal objective of growing our values per share. Given our differentiated business model relative to traditional insurance companies, we do not use the peer group to benchmark compensation. We believe that benchmarking against the insurance peer group could result in compensation that is not competitive for our talent pool. We seek to structure our compensation program to be less fixed and more variable than a traditional insurance company. When recruiting and retaining talented professionals, we compete against firms whose main business is derived from transactional activity, such as private equity and investment banking firms, and our compensation practices must reflect this reality. The CNG Committee takes account of the transactional component of our business when setting pay that is competitive and tied to rigorous performance goals. We believe our executive compensation program has driven tremendous value for shareholders, as evidenced by our long-term BVPS growth. BVPS reached $2,188 in 2025, up 25% year-over-year, and its growth over the last decade has been created in meaningful part through our transactions, as shown below. Over the Past Decade Our Transactions Have Driven Growth in BVPS The CNG Committee believes that our compensation structure closely aligns the financial interests of management with those of our shareholders and encourages appropriate, but not excessive, risk-taking. The CNG Committee regularly evaluates the continuing appropriateness of our peer group. See page 36 for further details on our peer group.

  18. Compensation Peer Group

    Compensation Peer Group When making new long-term incentive grants, the CNG Committee assesses the impact of different performance scenarios on potential realizable compensation. Further, in order to test our beliefs about the structure and variability of the awards we make, the CNG Committee annually reviews and considers a systematic analysis of the public compensation disclosures made by other property and casualty insurers and reinsurers that the CNG Committee uses as peers. Importantly, our compensation peer group is not used for benchmarking purposes, but rather to analyze whether our compensation programs are appropriately structured and to ensure they are less fixed and more variable than most other insurance and reinsurance peers. As many of our subsidiaries are insurance companies, we evaluate the executive compensation programs of a group of insurance company peers in terms of structure and variability of payouts in good and poor performance scenarios. However, unlike most of our insurance company peers, a primary responsibility of our parent company’s management is allocating capital and opportunistically finding and executing value-creating acquisitions and dispositions of operating businesses. Over the years, transaction gains have been a large driver of success in achieving our principal objective of growing our values per share. Given our differentiated model relative to insurance company peers, we do not use the peer group to benchmark compensation. We believe that benchmarking against the peer group could result in compensation that is not competitive for our talent pool. We seek to structure our compensation program to be less fixed and more variable than our insurance peers. When recruiting and retaining talented professionals, we compete against firms whose main business is derived from transactional activity, such as private equity and investment banking firms, and our compensation practices must reflect this reality. The CNG Committee takes account of the transactional component of our business when setting pay that is competitive and tied to rigorous performance goals. We believe our executive compensation program has driven tremendous value for shareholders, as evidenced by our long-term BVPS growth. BVPS reached $2,188 in 2025, up 25% year-over-year, and has grown steadily over the last decade in meaningful part through our transactions, as shown on pages 31 and 37. In considering its analysis of compensation structure and variability, the Company uses a peer group of insurance companies that engage in business similar to the business conducted by some of our subsidiaries. The CNG Committee regularly evaluates the continuing appropriateness of this group and did so again during 2025. The companies included in the analysis presented to the CNG Committee prior to it making compensation decisions in 2025 were unchanged from the prior year.

  19. Compensation Peer Group

    | 2025 Peer Group | | | | | | | ● | Arch Capital Group | ● | Hanover | ● | RLI Corp. | | ● | Assured Guaranty | ● | Kinsale | ● | Selective Insurance Group | | ● | Axis Capital | ● | Markel Corp | ● | SiriusPoint | | ● | Enstar | ● | RenaissanceRe Holdings | ● | W.R. Berkley | | ● | Everest Group | | | | |

  20. Compensation Peer Group

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

  21. 2. Annual Incentive Bonuses

    2. Annual Incentive Bonuses We provide annual bonus opportunities to our executive officers, which make up a relatively small percentage of each NEO’s target total annual compensation – approximately 8% for our CEO and 14% on average for the other NEOs in 2025 – as the bulk of our executive officers’ compensation opportunity is tied to long-term incentives. Each NEO participates in the annual bonus pool applicable to the parent holding companies. For 2025, the target bonus pool was $11.7 million for 64 employees. Under our formulaic 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 BVPS and growth in “intrinsic value per share,” which is the BVPS including franchise value adjustments to reflect the fair value of certain subsidiaries/affiliates 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 CNG 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. The 2025 annual bonus pool could range from 0% to 200% of target, based on the harvest scale of 6%-11%-16% growth in CVPS. In setting this performance scale, the CNG Committee’s goal was to set a performance target that was reasonable, but with an appropriate degree of stretch. The 11% target was roughly equal to the Company’s return target of the yield on the 10-year Treasury plus 700 basis points. For our executive officers, the CNG Committee maintains the discretion to decrease, but not increase, the individual annual bonus payouts after the quantitative formula has been applied. Our executive officers cannot receive more than the formulaic result. For 2025, the NEOs had base salaries which were unchanged from 2024, and target annual bonuses of 100% of salary, which were increased from 75% of salary in 2024. The CNG Committee believes that, inclusive of the bonus target change in 2025, executive officer salary and bonus target levels remain below general market practice and continue to reflect the CNG Committee’s long-standing philosophy of linking a vast majority of executives’ compensation to long-term incentives in order to align their interests with those of our shareholders, as opposed to awarding high levels of fixed cash compensation. Based on the Company’s performance of a 22.8% increase in CVPS in 2025, the CNG Committee awarded the NEOs bonuses of 200% of target.

  22. 2. Annual Incentive Bonuses

    | | 2025 Annual Bonus Decisions | | | | Executive | Target Bonus | Earned Bonus | % of Target | | G. Manning Rountree | $600,000 | $1,200,000 | 200% | | Liam P. Caffrey | $600,000 | $1,200,000 | 200% | | Giles E. Harrison(1) | $600,000 | $1,200,000 | 200% | | Robert L. Seelig | $600,000 | $1,200,000 | 200% | | Michaela J. Hildreth | $600,000 | $1,200,000 | 200% | | (1) Excludes a $250,000 sign-on bonus that was paid to Mr. Harrison in March 2025. | | | |

  23. 3. Long-Term Incentive Compensation

    3. Long-Term Incentive Compensation Long-term equity awards generally consist of an equal mix of restricted shares and performance shares, rewarding long-term value creation and aligning executives’ interests with shareholders’ interests. Restricted shares are subject to a three-year cliff-vesting provision, rather than annual vesting, in order to promote executive retention that balances incentives to redeploy capital aggressively and to remain patient for optimal opportunities for the Company and its shareholders. The number of WTM common shares earned from a grant of performance shares can range from 0%-200% of target, based on after-tax annual growth in CVPS over the three-year performance cycle. 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. 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. 2025 Long-Term Incentive Grants: For the CEO and each of our other NEOs, the annual 2025 long-term incentive awards were allocated 50% as performance shares and 50% as restricted shares, consistent with prior years. With respect to the total grants made to employees across the Company, the CNG Committee granted 21,340 target shares for the 2025-2027 performance cycle, which represented an approximately 6% decrease, year-over-year, in the number of shares granted. These grants totaled approximately 0.8% of the then outstanding shares. The restricted shares are subject to a three-year cliff-vesting provision based on continuous service in order to promote the retention of key executive talent. The performance shares vest in a range of 0% - 200% of target following a three-year performance period. For the 2025-2027 performance period, the CNG Committee established a target of 11.5% annual growth in CVPS as the performance target that would result in the payout of 100% of the target performance shares. There would be no payout for annual growth of 6% or less, and annual growth of 17% or more would be required for a payout of 200%. In setting this performance scale, the CNG Committee’s goal was to set a performance target that was reasonable, but with an appropriate degree of stretch. Importantly, the 11.5% target was roughly equal to the Company’s long-term return target of the yield on the 10-year Treasury plus 700 basis points, consistent with the Company’s practice for several years. A detailed breakdown of the 2025 grants is included in the table below:

  24. 3. Long-Term Incentive Compensation

    | | 2025 Long-Term Incentive Grants | | | | | | | | Grant Date | Restricted Shares | | Performance Shares | | Total 2025 LTI Grant Value | | Executive | | # Shares | Grant Value | # Shares | Grant Value | | | G. Manning Rountree | 2/26/2025 | 1,625 | $2,977,309 | 1,625 | $2,977,309 | $5,954,618 | | Liam P. Caffrey | 2/26/2025 | 1,025 | $1,877,995 | 1,025 | $1,877,995 | $3,755,990 | | Giles E. Harrison | 2/26/2025 | 900 | $1,648,971 | 900 | $1,648,971 | $3,297,942 | | Robert L. Seelig | 2/26/2025 | 825 | $1,511,557 | 825 | $1,511,557 | $3,023,114 | | Michaela J. Hildreth | 2/26/2025 | 625 | $1,145,119 | 625 | $1,145,119 | $2,290,238 |

  25. 3. Long-Term Incentive Compensation

    In determining the amount of new long-term incentive compensation grants for our NEOs for 2025, the CNG Committee assessed each executive’s scope of authority and ability to impact the success of the Company. Based on the CNG Committee’s general experience, familiarity with the Company and its compensation practices and the recommendation of the CEO (for NEOs other than himself), the CNG Committee established a grant level that it believed was appropriate to reflect each such executive’s expected contribution to the Company over the next performance cycle. Payout of 2023-2025 Performance Cycle: For the 2023-2025 performance cycle, long-term incentives were granted to the NEOs as follows: 50% as performance shares and 50% as restricted shares. For the performance shares, which matured at the end of 2025, 11% annual growth in CVPS was the performance target for a payout of 100% of the target performance shares. Annual growth of 6% or less would have resulted in no payout, and annual growth of 16% or more would have resulted in a payout of 200%. At its meeting in February 2026, based on an average annual growth in CVPS of 15.2% during the 2023-2025 performance cycle, the CNG Committee confirmed that the payout that was earned was 184% of target.

  26. 3. Long-Term Incentive Compensation

    | 2023-2025 Performance Share Cycle | | | | | | | Executive | Target Shares | Performance Scale (min / target / max) | Actual Annual Growth | Payout % | Shares Earned | | G. Manning Rountree | 2,000 | 6% - 11% - 16% | 15.2% | 184% | 3,680 | | Liam P. Caffrey | 1,250 | 6% - 11% - 16% | 15.2% | 184% | 2,300 | | Robert L. Seelig | 1,000 | 6% - 11% - 16% | 15.2% | 184% | 1,840 | | Michaela J. Hildreth | 600 | 6% - 11% - 16% | 15.2% | 184% | 1,104 | | Note: Mr. Harrison joined the Company on June 10, 2024 and therefore did not receive a 2023-2025 performance share grant. | | | | | |

  27. Clawback Policy

    Clawback Policy The CNG Committee adopted a recovery policy for the Company which is applicable to performance-based compensation for the Company’s current and former executive officers and complies with NYSE rules. The policy requires the recovery of performance-based compensation in the case of an accounting restatement, without regard to fault. The Company has also adopted a clawback policy applicable to bonuses (including non-equity incentive plan compensation) and long-term incentive awards (including time-based awards). If the Company restates any financial statement included in an SEC filing as a result of an employee’s misconduct, the Board may, without prejudice to any other remedies available to the Company, seek reimbursement of any bonus or long-term incentive award received by such person that relates in whole or in part to any period for which such financial statements were restated. If the misconduct involved fraud, then in addition to other actions, the Board will mandatorily seek such reimbursement.

  28. Employment Agreements; Compensation Arrangement for Mr. Rountree

    Employment Agreements; Compensation Arrangement for Mr. Rountree We typically do not enter into employment agreements with our NEOs. From time to time we have entered into short-term arrangements with (a) newly hired executives governing their compensation and severance for a period of up to their first three years with the Company or (b) departing executives in connection with their transition into advisory roles. On September 2, 2025, the Company announced that Mr. Rountree would retire from the Chief Executive Officer position on December 31, 2025 and become a Senior Advisor to the Company. On January 1, 2026, Mr. Rountree and White Mountains Capital (“WMC”), acting with the approval of the CNG Committee, entered into an employment agreement (the “Rountree Agreement”) relating to Mr. Rountree’s service as a Senior Advisor. Under the Rountree Agreement, Mr. Rountree will (a) be paid a base salary at the annual rate of $300,000, (b) participate in WMC’s employee benefit plans and (c) not be granted any new equity incentives during the period of the Agreement. In addition, Mr. Rountree’s existing 3,425 performance shares and 3,425 restricted shares will remain outstanding and continue to vest in accordance with their terms, except as follows. If the Company were to terminate Mr. Rountree’s employment for Cause, or if Mr. Rountree resigns voluntarily, the Company would terminate any outstanding equity incentives without any payment. If the Company were to terminate Mr. Rountree’s employment without Cause, the Company shall (i) if such termination occurs in 2026, (v) immediately accelerate the vesting of the 2024 restricted share award (“RSA”) and the 2025 RSA, (w) settle the 2024-2026 performance share award (“PSA”) at the same time and in the same amounts as if Mr. Rountree had continued employment until the normal vesting date thereof (assuming the same level of performance achievement applied to other Company executives), (x) settle the 2025-2027 PSA prior to March 15, 2027 based on the same performance achievement through the end of the Company’s 2026 fiscal year applied to other Company executives, and (ii) if such termination occurs during 2027, (x) immediately accelerate the vesting of the 2025 RSA and (y) settle the 2025-2027 PSA at the same time and in the same amounts as if Mr. Rountree had continued employment until the normal vesting date thereof (assuming the same level of performance achievement applied to other Company executives). The Rountree Agreement also provides that Mr. Rountree will be subject to certain restrictive covenants.

  29. Severance Agreements; Change in Control

    Severance Agreements; Change in Control Severance benefits, if any, for our NEOs are determined by the CNG Committee in its sole discretion. Executive officers of our operating subsidiaries participate in the severance plans, if any, generally applicable at those companies. If any of our most senior executives decide to retire, in order to enable the Company to ensure a smooth transition, to receive a non-compete/non-solicit from the executive and to retain access to valuable knowledge, talents and relationships, our general practice has been to enter into arrangements that would permit the executive to earn some or all of such executive’s long-term incentive compensation then outstanding. We have no standalone change in control agreements with our NEOs. However, under our long-term incentive plans, if a change in control of the Company (or a business unit, as applicable) were to occur, certain events, such as involuntary or constructive employment termination or amendments to our incentive plans which are materially adverse to its participants, may cause restricted shares to become immediately vested and performance shares and performance units to become payable in full or in part. Our plans do not provide for tax gross-ups for excess parachute payments that may result from a change in control.

  30. Summary Compensation Table

    Summary Compensation Table The following table presents compensation in 2025, 2024 and 2023 for the Company’s CEO, CFO and its three other most highly compensated executive officers (collectively, the “Named Executive Officers”):

  31. Summary Compensation Table

    | Name and Principal Position | Year | Salary ($) | Bonus (a) ($) | Stock Awards Granted (b) ($) | Option Awards Granted ($) | Non-Equity Incentive Plan Compensation (c) ($) | Change in Pension Value and Nonqualified Deferred Compensation Earnings ($) | All Other Compensation (d) ($) | Total ($) | | G. Manning Rountree (e) | 2025 | 600,000 | - | 5,954,618 | - | 1,200,000 | - | 309,691 | 8,064,309 | | Chief Executive Officer | 2024 | 600,000 | - | 6,352,596 | - | 211,500 | - | 258,862 | 7,422,958 | | | 2023 | 584,615 | - | 5,872,920 | - | 765,000 | - | 354,466 | 7,577,001 | | Liam P. Caffrey (f) | 2025 | 600,000 | - | 3,755,990 | - | 1,200,000 | - | 389,501 | 5,945,491 | | President & | 2024 | 600,000 | 325,000 | 3,970,373 | - | 211,500 | - | 361,121 | 5,467,994 | | Chief Financial Officer | 2023 | 584,615 | 325,000 | 3,670,575 | - | 765,000 | - | 335,884 | 5,681,074 | | Giles E. Harrison (g) | 2025 | 600,000 | 250,000 | 3,297,942 | - | 1,200,000 | - | 20,808 | 5,368,750 | | Executive Vice President & | 2024 | 334,615 | 250,000 | 3,454,400 | - | 211,500 | - | 43,547 | 4,294,062 | | Chief Strategy Officer | | | | | | | | | | | Robert L. Seelig | 2025 | 600,000 | - | 3,023,114 | - | 1,200,000 | - | 119,020 | 4,942,134 | | Executive Vice President & | 2024 | 600,000 | - | 3,176,298 | - | 211,500 | - | 152,703 | 4,140,501 | | General Counsel | 2023 | 584,615 | - | 2,936,460 | - | 765,000 | - | 116,223 | 4,402,298 | | Michaela J. Hildreth | 2025 | 600,000 | - | 2,290,238 | - | 1,200,000 | - | 23,058 | 4,113,296 | | Managing Director & | 2024 | 600,000 | - | 2,117,532 | - | 211,500 | - | 22,131 | 2,951,163 | | Chief Accounting Officer | 2023 | 584,615 | - | 1,761,876 | - | 765,000 | - | 26,220 | 3,137,711 |

  32. Summary Compensation Table

    | (a) For Mr. Caffrey, the amounts in 2024 and 2023 represent the final two tranches of a $975,000 sign-on bonus, payable in three equal annual installments, awarded to incentivize him to join the Company. For Mr. Harrison, the amounts in 2025 and 2024 represent the first two of three tranches of a $750,000 sign-on bonus, payable in three equal annual installments, awarded to incentivize him to join the Company. See “Compensation Discussion and Analysis.” |

  33. Summary Compensation Table

    | (b) Represents the grant date market value of WTM performance shares granted in 2025, 2024 and 2023 and WTM restricted shares issued in 2025, 2024 and 2023. The WTM performance share awards included in the table have a maximum payout of 200% of the shares granted and, at such level, would have a grant date fair value equal to 200% of the amounts shown in the Grants of Plan Based Awards table. See “Grants of Plan Based Awards” and “Outstanding Equity Awards at Fiscal Year End.” |

  34. Summary Compensation Table

    | (c) Amounts presented in 2025 represent annual incentive awards paid in cash in March 2026 for performance in the year ended December 31, 2025. Amounts presented in 2024 represent annual incentive awards paid in cash in March 2025 for performance in the year ended December 31, 2024. Amounts presented in 2023 represent annual incentive awards paid in cash in March 2024 for performance in the year ended December 31, 2023. See “Compensation Discussion and Analysis.” |

  35. Summary Compensation Table

    | (d) See next table for details of All Other Compensation. |

  36. Summary Compensation Table

    | (e) Mr. Rountree retired as CEO on December 31, 2025, and remains employed as a Senior Advisor but is no longer an executive officer. |

  37. Summary Compensation Table

    | (f) Mr. Caffrey was appointed CEO and elected to the board of directors effective January 1, 2026. |

  38. Summary Compensation Table

    | (g) Mr. Harrison was appointed President effective January 1, 2026. |

  39. Grants of Plan-Based Awards

    Grants of Plan-Based Awards The following table presents plan-based awards granted, except as otherwise noted, under the White Mountains Long-Term Incentive Plan (the “WTM Incentive Plan”) to the Named Executive Officers that received such awards during 2025:

  40. Grants of Plan-Based Awards

    | | | | Estimated Future Payouts Under Non-Equity Incentive Plan Awards (a) | | | Estimated Future Payouts Under Equity Incentive Plan Awards (b) | | | All Other Stock Awards: | All Other Option Awards: | Exercise | Grant Date | | Name | Grant Date | Type of Award | Threshold ($) | Target ($) | Maximum ($) | Threshold (#) | Target (#) | Maximum (#) | Number of Shares of Stock or Units (c) (#) | Number of Securities Underlying Options (#) | or Base Price of Option Awards ($/sh) | Fair Value of Stock and Option Awards (d) ($) | | G. Manning Rountree | | Annual Incentive Bonus | 0 | 600,000 | 1,200,000 | - | - | - | - | - | - | - | | | 2/26/25 | WTM Performance Shares | - | - | - | 0 | 1,625 | 3,250 | - | - | - | 2,977,309 | | | 2/26/25 | WTM Restricted Shares | - | - | - | - | - | - | 1,625 | - | - | 2,977,309 | | Liam P. Caffrey | | Annual Incentive Bonus | 0 | 600,000 | 1,200,000 | - | - | - | - | - | - | - | | | 2/26/25 | WTM Performance Shares | - | - | - | 0 | 1,025 | 2,050 | - | - | - | 1,877,995 | | | 2/26/25 | WTM Restricted Shares | - | - | - | - | - | - | 1,025 | - | - | 1,877,995 | | Giles E. Harrison | | Annual Incentive Bonus | 0 | 600,000 | 1,200,000 | - | - | - | - | - | - | - | | | 2/26/25 | WTM Performance Shares | - | - | - | 0 | 900 | 1,800 | - | - | - | 1,648,971 | | | 2/26/25 | WTM Restricted Shares | - | - | - | - | - | - | 900 | - | - | 1,648,971 | | Robert L. Seelig | | Annual Incentive Bonus | 0 | 600,000 | 1,200,000 | - | - | - | - | - | - | - | | | 2/26/25 | WTM Performance Shares | - | - | - | 0 | 825 | 1,650 | - | - | - | 1,511,557 | | | 2/26/25 | WTM Restricted Shares | - | - | - | - | - | - | 825 | - | - | 1,511,557 | | Michaela J. Hildreth | | Annual Incentive Bonus | 0 | 600,000 | 1,200,000 | - | - | - | - | - | - | - | | | 2/26/25 | WTM Performance Shares | - | - | - | 0 | 625 | 1,250 | - | - | - | 1,145,119 | | | 2/26/25 | WTM Restricted Shares | - | - | - | - | - | - | 625 | - | - | 1,145,119 |

  41. Grants of Plan-Based Awards

    | (a) These columns indicate the range of payouts (0%, 100% and 200%) targeted for fiscal 2025 performance under our Annual Incentive Bonus Plan as described in “Compensation Discussion and Analysis”. The actual payout with respect to 2025 for each Named Executive Officer is shown in the Summary Compensation Table in the column titled “Non-Equity Incentive Plan Compensation.” |

  42. Grants of Plan-Based Awards

    | (b) Messrs. Rountree, Caffrey, Harrison and Seelig and Ms. Hildreth were granted WTM performance shares for the 2025-2027 performance cycle. For the 2025-2027 performance cycle, the targeted performance goal for full payment of outstanding WTM performance shares granted under the WTM Incentive Plan for all NEOs is an 11.5% average growth in CVPS. Average growth of 6% or less would result in no payout and average growth of 17% or more would result in a payout of 200%. |

  43. Grants of Plan-Based Awards

    | (c) Messrs. Rountree, Caffrey, Harrison and Seelig and Ms. Hildreth were granted WTM restricted shares that vest on January 1, 2028. |

  44. Grants of Plan-Based Awards

    | (d) Represents the grant date fair value (based on a market price on the date of grant) as determined in accordance with ASC Topic 718 without regard to forfeitures. Assuming a maximum 200% payout, the grant date fair value of the WTM performance shares granted to Messrs. Rountree, Caffrey, Harrison and Seelig and Ms. Hildreth would be $5,954,618, $3,755,990, $3,297,942, $3,023,114 and $2,290,238. |

  45. Outstanding Equity Awards at Fiscal Year-End

    Outstanding Equity Awards at Fiscal Year-End The following table presents outstanding equity awards under the WTM Incentive Plan, except as otherwise noted, to the Named Executive Officers as of December 31, 2025:

  46. Outstanding Equity Awards at Fiscal Year-End

    | Name | | Option Awards | | | | | Stock Awards (a)(b)(c) | | | | | | Type of Award | Number of Securities Underlying Unexercised Options (# Exercisable) | Number of Securities Underlying Unexercised Options (# Unexercisable) | Equity Incentive Plan Awards: Number of Securities Underlying Unexercised Unearned Options (#) | Option Exercise Price ($) | Option Expiration Date | Number of Shares or Units of Stock That Have Not Vested (#) | Market Value of Shares or Units of Stock That Have Not Vested ($) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested (#) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested ($) | | G. Manning Rountree | WTM Performance Shares | - | - | - | - | - | - | - | 3,425 | 14,244,956 | | | WTM Restricted Shares | - | - | - | - | - | 5,425 | 11,273,313 | - | - | | Liam P. Caffrey | WTM Performance Shares | - | - | - | - | - | - | - | 2,150 | 8,942,079 | | | WTM Restricted Shares | - | - | - | - | - | 3,400 | 7,065,302 | - | - | | Giles E. Harrison | WTM Performance Shares | - | - | - | - | - | - | - | 1,900 | 7,902,314 | | | WTM Restricted Shares | - | - | - | - | - | 1,900 | 3,948,257 | - | - | | Robert L. Seelig | WTM Performance Shares | - | - | - | - | - | - | - | 1,725 | 7,174,454 | | | WTM Restricted Shares | - | - | - | - | - | 2,725 | 5,662,632 | - | - | | Michaela J. Hildreth | WTM Performance Shares | - | - | - | - | - | - | - | 1,225 | 5,094,824 | | | WTM Restricted Shares | - | - | - | - | - | 1,825 | 3,792,405 | - | - |

  47. Outstanding Equity Awards at Fiscal Year-End

    | (a) Equity incentive plan awards not yet vested at December 31, 2025 for Messrs. Rountree, Caffrey, Harrison and Seelig and Ms. Hildreth include 1,625, 1,025, 900, 825 and 625 target WTM performance shares, respectively, for the 2025-2027 performance cycle and 1,800, 1,125, 1,000, 900 and 600 target WTM performance shares, respectively, for the 2024-2026 performance cycle. Payout values for WTM performance shares are shown at 200% of target for both the 2025-2027 and the 2024-2026 performance cycles and based on the December 31, 2025 closing market price ($2,078.03) including dividends declared since the grant date. |

  48. Outstanding Equity Awards at Fiscal Year-End

    | (b) Stock awards not yet vested at December 31, 2025 for Messrs. Rountree, Caffrey, Harrison and Seelig and Ms. Hildreth include 1,625, 1,025, 900, 825 and 625 WTM restricted shares, respectively, that vest on January 1, 2028; 1,800, 1,125, 1,000, 900 and 600 WTM restricted shares, respectively, that vest on January 1, 2027; and 2,000, 1,250, 0, 1,000 and 600 WTM restricted shares, respectively, that vested on January 1, 2026. Market values are based on the December 31, 2025 closing market price ($2,078.03). |

  49. Outstanding Equity Awards at Fiscal Year-End

    | (c) Excludes WTM performance shares for the 2023-2025 performance cycle, which vested on December 31, 2025. See “Option Exercises and Stock Vested.” |

  50. Option Exercises and Stock Vested

    Option Exercises and Stock Vested The following table presents stock awards that vested in 2025 for each of the Named Executive Officers. No option awards were exercised by the Named Executive Officers during 2025.

  51. Option Exercises and Stock Vested

    | Name | Option Awards Exercised | | Stock Awards Vested | | | | | Number of Shares Acquired on Exercise (#) | Value Realized on Exercise ($) | Type of Award | Number of Shares Acquired on Vesting (#) | Value Realized on Vesting ($) | | G. Manning Rountree | - | - | WTM Performance Shares(a) | 3,680 | 8,139,608 | | | | | WTM Restricted Shares(b) | 2,700 | 5,251,662 | | Liam P. Caffrey | - | - | WTM Performance Shares(a) | 2,300 | 5,087,255 | | | | | WTM Restricted Shares(b) | 1,250 | 2,431,325 | | Giles E. Harrison | - | - | WTM Performance Shares(a) | - | - | | | | | WTM Restricted Shares(b) | - | - | | Robert L. Seelig | - | - | WTM Performance Shares(a) | 1,840 | 4,069,804 | | | | | WTM Restricted Shares(b) | 1,250 | 2,431,325 | | Michaela J. Hildreth | - | - | WTM Performance Shares(a) | 1,104 | 2,441,882 | | | | | WTM Restricted Shares(b) | 750 | 1,458,795 |

  52. Option Exercises and Stock Vested

    | (a) Represents 2,000, 1,250, 0, 1,000 and 600 target WTM performance shares awarded for the 2023-2025 performance cycle to Messrs. Rountree, Caffrey, Harrison and Seelig and Ms. Hildreth, respectively, which became fully vested on December 31, 2025 at 184% of target. Value realized on vesting is based on the average of the closing price of common shares for the 5 days preceding the CNG Committee meeting in February 2026, as determined by the CNG Committee, plus dividends declared since the shares were granted in 2023. |

  53. Option Exercises and Stock Vested

    | (b) The amounts represent WTM restricted shares that vested on January 1, 2025. |

  54. Pay Versus Performance

    Pay Versus Performance The following table presents “Compensation Actually Paid” to the Principal Executive Officer (“PEO”) and the “Average Compensation Actually Paid” to the Non-PEO NEOs in 2025, 2024, 2023, 2022 and 2021, as calculated pursuant to SEC rules.

  55. Pay Versus Performance

    | Year (a) | Summary Compensation Table Total for PEO ($)(b) | Compensation Actually Paid to PEO ($) | Average Summary Compensation Table Total for Non-PEO NEOs ($)(b) | Average Compensation Actually Paid to Non-PEO NEOs ($) | Value of Initial Fixed $100 Investment Based On: | | Net Income (Loss) (millions $) | Annual Growth in Compensation Value per Share(d) | | | | | | | Total Shareholder Return ($) | Peer Group Total Shareholder Return ($)(c) | | | | 2025 | 8,064,309 | 16,330,438 | 5,092,417 | 8,846,701 | 208.42 | 234.32 | 1,106.4 | 22.8% | | 2024 | 7,422,958 | 14,100,992 | 4,213,430 | 6,247,597 | 175.12 | 227.67 | 230.4 | 8.3% | | 2023 | 7,577,001 | 11,680,222 | 3,697,210 | 4,999,435 | 135.42 | 168.05 | 509.2 | 14.5% | | 2022 | 7,191,754 | 23,147,640 | 3,169,569 | 7,992,051 | 127.17 | 151.65 | 792.8 | 23.9% | | 2021 | 7,185,569 | 4,639,595 | 2,906,827 | 2,095,752 | 91.08 | 127.58 | (275.4) | -1.2% |

  56. Pay Versus Performance

    | (a) The PEO and Non-PEO NEOs for the applicable years were as follows: | | 2025 and 2024: Mr. Rountree served as PEO and Messrs. Caffrey, Harrison and Seelig and Ms. Hildreth served as Non-PEO NEOs | | 2023 and 2022: Mr. Rountree served as PEO and Messrs. Caffrey, Campbell and Seelig and Ms. Hildreth served as Non-PEO NEOs | | 2021: Mr. Rountree served as PEO and Messrs. Frank Bazos, Campbell and Seelig and Ms. Hildreth served as Non-PEO NEOs |

  57. Pay Versus Performance

    | (b) The amounts reported as “Compensation Actually Paid” to our PEO and “Average Compensation Actually Paid” to our Non-PEO NEOs in each of 2025, 2024, 2023, 2022 and 2021 represent the respective amounts as determined in accordance with Item 402(v) of Regulation S-K. The amounts do not reflect the actual amount of compensation earned by or paid to our PEO or Non-PEO NEOs during the applicable year. The Summary Compensation Table totals reported for the PEO and the average of the Non-PEO NEOs for each year were subject to the following adjustments per Item 402(v)(2)(iii) of Regulation S-K to calculate “Compensation Actually Paid”: |

  58. Pay Versus Performance

    | PEO | | | | | | | | 2025 | 2024 | 2023 | 2022 | 2021 | | Summary Compensation Table (“SCT”) total | 8,064,309 | 7,422,958 | 7,577,001 | 7,191,754 | 7,185,569 | | Less: Value Reported in the SCT of Stock Awards | (5,954,618) | (6,352,596) | (5,872,920) | (5,604,282) | (6,478,434) | | Granted in the Covered Year | | | | | | | Plus: Year-end Value for Stock Awards | 8,613,356 | 7,004,016 | 6,775,045 | 11,461,473 | 4,107,645 | | Granted in the Covered Year | | | | | | | Change in Fair Value of Unvested Stock | 6,146,203 | 4,766,206 | 2,602,290 | 9,901,354 | (1,500,285) | | Awards from Prior Years that Remain Unvested | | | | | | | Change in Fair Value of Stock Awards | (538,812) | 1,260,408 | 598,806 | 197,341 | 1,325,100 | | from Prior Years that Vested in Covered Year | | | | | | | Compensation Actually Paid | 16,330,438 | 14,100,992 | 11,680,222 | 23,147,640 | 4,639,595 | | Average of the Non-PEO NEOs | | | | | | | | 2025 | 2024 | 2023 | 2022 | 2021 | | Summary Compensation Table (“SCT”) total | 5,092,417 | 4,213,430 | 3,697,210 | 3,169,569 | 2,906,827 | | Less: Value Reported in the SCT of Stock Awards | (3,091,821) | (3,179,651) | (2,092,228) | (1,686,474) | (2,039,507) | | Granted in the Covered Year | | | | | | | Plus: Year-end Value for Stock Awards | 4,472,319 | 3,526,328 | 2,413,610 | 3,449,054 | 1,293,148 | | Granted in the Covered Year | | | | | | | Change in Fair Value of Unvested Stock | 2,535,929 | 1,500,763 | 808,963 | 3,003,988 | (528,501) | | Awards from Prior Years that Remain Unvested | | | | | | | Change in Fair Value of Stock Awards | (162,143) | 186,727 | 171,880 | 55,912 | 463,785 | | from Prior Years that Vested in Covered Year | | | | | | | Compensation Actually Paid | 8,846,701 | 6,247,597 | 4,999,435 | 7,992,051 | 2,095,752 |

  59. Pay Versus Performance

    | (c) Peer Group Total Shareholder Return “TSR” reflects the S&P 500 Property & Casualty Insurance Index as reflected in our Annual Report on the Form 10-K pursuant to Item 201(e) of Regulation S-K for the fiscal year ended December 31, 2025. Each year reflects what the cumulative value of $100 would be, including the reinvestment of dividends, if such amount had been invested on December 31, 2020. |

  60. Pay Versus Performance

    | (d) For calendar years 2025 and forward, CVPS is the average of growth in book value per share (BVPS) and growth in intrinsic value per share, which is the BVPS including franchise value adjustments to reflect a conservative estimate of the fair value of certain subsidiaries/affiliates carried at book value. For calendar years through 2024, CVPS is the average of growth in adjusted book value per share (ABVPS) and growth in intrinsic value per share. See Annex A for a reconciliation of growth in ABVPS and BVPS to growth in intrinsic value per share. |

  61. Financial Performance Measures

    | Relationship Between Pay and Performance In 2025, strong growth in CVPS positively correlated with growth in Compensation Actually Paid for the following reasons. Based on the Company’s performance of 22.8% growth in CVPS in 2025, the PEO and NEOs received bonuses of 200% of target for 2025. During 2025, the fair value of all performance shares included in the calculation of Compensation Actually Paid to the PEO and Average Compensation Actually Paid to the non-PEO NEOs increased significantly as (1) the level of growth in CVPS resulted in higher projected payout percentages on all outstanding performance cycles and (2) the Company’s share price increased by 6.8% during 2025. The fair value of all restricted shares outstanding used in the calculation of Compensation Actually Paid to the PEO and Average Compensation Actually Paid to the non-PEO NEOs also increased in 2025 as a direct result of the 6.8% increase in the Company’s share price during the year. The increase in the Company’s net income also positively correlated with growth in compensation actually paid as net income drove the increase in growth in CVPS. The Company’s TSR also positively correlated with the level of compensation actually paid, though not as much as growth in CVPS, as the increase in share price partially accounted for the increase in value in outstanding performance shares and restricted shares. In 2024, Compensation Actually Paid to the PEO and Average Compensation Actually Paid to the non-PEO NEOs increased compared to 2023. The primary driver was an increase in the fair value of all performance and restricted shares included in the calculation of Compensation Actually Paid to the PEO and Average Compensation Actually Paid to the non-PEO NEOs as the Company’s share price increased by 29.2% during 2024, compared to a 6.4% increase during 2023. Partially mitigating this increase, CVPS grew at a slower pace in 2024 than in 2023 resulting in a slightly lower projected payout percentage on the 2023-2025 performance cycle in 2024. Based on the Company’s performance of 8.3% growth in CVPS in 2024, the PEO and NEOs received bonuses of 47% of target for 2024 compared to 170% of target for 2023. The Company’s net income of $230.4 million in 2024 compared to $509.2 million in 2023 contributed to the decrease in growth in CVPS. The Company’s TSR positively correlated with the level of Compensation Actually Paid as the increase in the Company’s share price primarily accounted for the increase in value in outstanding performance shares and restricted shares. In 2023, CVPS grew at a slower pace than in 2022 resulting in a decrease in Compensation Actually Paid in 2023 compared to 2022. Based on the Company’s performance of 14.5% growth in CVPS in 2023, the PEO and NEOs received bonuses of 170% of target for 2023. During 2023, the fair value of all performance shares included in the calculation of Compensation Actually Paid to the PEO and Average Compensation Actually Paid to the non-PEO NEOs increased as (1) the level of growth in CVPS resulted in a higher projected payout percentage on the 2021-2023 performance cycle and (2) the Company’s share price increased by 6.4% during 2023. However, both of these factors increased at a lower rate than in 2022. The fair value of all restricted shares outstanding used in the calculation of Compensation Actually Paid to the PEO and Average Compensation Actually Paid to the non-PEO NEOs also increased in 2023 as a direct result of the 6.4% increase in the Company’s share price during the year, which was lower than the 39.5% increase in 2022. The Company’s net income of |

  62. Financial Performance Measures

    | $509.2 million in 2023 positively correlated with growth in compensation actually paid as net income drove the increase in growth in CVPS. The Company’s TSR also positively correlated with the level of compensation actually paid, though not as much as growth in CVPS, as the increase in share price partially accounted for the increase in value in outstanding performance shares and restricted shares. In 2022, strong growth in CVPS positively correlated with growth in Compensation Actually Paid for the following reasons. Based on the Company’s performance of 23.9% growth in CVPS in 2022, the PEO and NEOs received bonuses of 200% of target for 2022. During 2022, the fair value of all performance shares included in the calculation of Compensation Actually Paid to the PEO and Average Compensation Actually Paid to the non-PEO NEOs increased significantly as (1) the level of growth in CVPS resulted in higher projected payout percentages on all outstanding performance cycles and (2) the Company’s share price increased by 39.5% during 2022. The fair value of all restricted shares outstanding used in the calculation of Compensation Actually Paid to the PEO and Average Compensation Actually Paid to the non-PEO NEOs also increased in 2022 as a direct result of the 39.5% increase in the Company’s share price during the year. The increase in the Company’s net income also positively correlated with growth in compensation actually paid as net income drove the increase in growth in CVPS. The Company’s TSR also positively correlated with the level of compensation actually paid, though not as much as growth in CVPS, as the increase in share price partially accounted for the increase in value in outstanding performance shares and restricted shares. In 2021, negative growth in CVPS correlated with a decrease in compensation actually paid. For 2021, the PEO and NEOs received no bonuses and projected payout percentages on outstanding performance shares decreased from the prior year end. The decrease in the Company’s net income also correlated with the decrease in compensation actually paid as the net loss drove the decrease in growth in CVPS. The Company’s TSR of 1.4% somewhat correlated with the lower level of compensation actually paid. The small increase in the value of each restricted share and performance share outstanding was more than offset by the reduction in the projected payout percentages on all outstanding performance share cycles due to the negative growth in CVPS. The following chart provides a graphical representation of the Company's five-year cumulative TSR versus our industry peer group, the S&P 500 Property & Casualty Insurance Index. |

  63. Pension Benefits

    Pension Benefits The Named Executive Officers did not participate in any defined pension plans sponsored by White Mountains in 2025.

  64. Nonqualified Deferred Compensation

    Nonqualified Deferred Compensation The Named Executive Officers did not participate in any nonqualified deferred compensation plans sponsored by White Mountains in 2025.

  65. Potential Payments Upon Termination or Change in Control

    Potential Payments Upon Termination or Change in Control

  66. Director Compensation

    Director Compensation Our CNG Committee has adopted a compensation program for our non-employee directors that is focused on:

  67. Director Compensation

    | ● | attracting and retaining highly-qualified directors with a diversity of skills, backgrounds and experiences |

  68. Director Compensation

    | ● | appropriately valuing the significant time and travel commitment required for our non-employee directors |

  69. Director Compensation

    | ● | encouraging directors’ ownership of our common shares to further the alignment of their interests with those of our shareholders |

  70. Director Compensation

    To that end, our non-employee director compensation program in effect for fiscal 2025 included the following elements:

  71. Director Compensation

    | ● | an annual cash retainer of $135,000 |

  72. Director Compensation

    | ● | an annual equity retainer of 150 common shares |

  73. Director Compensation

    | ● | an additional retainer of $100,000 and 60 common shares for our Board Chair |

  74. Director Compensation

    | ● | an additional cash retainer of $15,000 for each member of the Audit Committee |

  75. Director Compensation

    | ● | additional annual retainers (in addition to member retainer) of $35,000 and $25,000 for chairs of the Audit Committee and all other committees, respectively |

  76. Director Compensation

    Our non-employee directors are not provided with any benefits other than participating in our employee matching gift program on the same terms as our employees, matching gifts up to $10,000 per participating individual. As described in the notes to the table below, due to his extensive insurance industry expertise, Mr. Campbell served on the board of a subsidiary of the Company during 2025. For his service, he received director fees, which are included under “All Other Compensation.” The following table summarizes director compensation for 2025 (for directors other than Named Executive Officers):

  77. Director Compensation

    | Director | Fees Paid in Cash (a) ($) | Stock Awards (b) ($) | Option Awards ($) | Non-Equity Incentive Plan Compensation ($) | Change in Pension Value and Nonqualified Deferred Compensation Earnings ($) | All Other Compensation (c) ($) | Total ($) | | Reid T. Campbell | 135,000 | 269,648 | - | - | - | 103,701 | 508,349 | | Peter M. Carlson | 185,000 | 269,648 | - | - | - | 8,519 | 463,167 | | Mary C. Choksi | 160,000 | 269,648 | - | - | - | 10,000 | 439,648 | | Margaret Dillon | 150,000 | 269,648 | - | - | - | - | 419,648 | | Philip A. Gelston | 175,000 | 269,648 | - | - | - | 3,000 | 447,648 | | Weston M. Hicks | 250,000 | 377,507 | - | - | - | - | 627,507 | | Suzanne F. Shank | 135,000 | 269,648 | - | - | - | - | 404,648 | | David A. Tanner | 150,000 | 269,648 | - | - | - | - | 419,648 | | Steven M. Yi | 135,000 | 269,648 | - | - | - | - | 404,648 |

  78. Director Compensation

    | (a) Mr. Rountree does not receive any additional compensation for his role as a director. Non-management directors receive an annual cash retainer of $135,000. Additional retainers in the following amounts are provided to those directors serving in the following roles: Chairman of the Board ($100,000), Chairman of the Audit Committee ($35,000), Chairman of any other Board committee ($25,000) and members of the Audit Committee ($15,000). Retainers were all paid in cash. Retainers relate to the period from May 2025 to May 2026, inclusive, and are typically pro-rated for partial year service. |

  79. Director Compensation

    | (b) On May 22, 2025, all non-management directors received an annual grant of 150 common shares. Mr. Hicks received an additional 60 common shares for his role as Chairman of the Board. All common shares issued were valued at $1,797.65 per share, the market price on the date the shares were granted. |

  80. Director Compensation

    | (c) Amount shown for Mr. Campbell represents $80,000 in fees paid to him by Ark for service as a director, $7,500 in matching payments from a company-sponsored charitable gift program and $16,201 incremental cost to the Company for the use of corporate aircraft that were not otherwise in use for business. For Company aircraft, the incremental cost is the cost per hour multiplied by the number of hours of use. Amounts shown for Mr. Carlson, Ms. Choksi and Mr. Gelston represent matching payments from a company-sponsored charitable gift program. |

  81. Director Compensation

    CEO PAY RATIO

  82. CEO Pay Ratio

    CEO Pay Ratio Below is (i) the 2025 annual total compensation of our CEO; (ii) the 2025 annual total compensation of our median employee; (iii) the ratio of the annual total compensation of our CEO to that of our median employee, and (iv) the methodology we used to calculate our CEO pay ratio:

  83. CEO Pay Ratio

    | CEO Annual Total Compensation | $8,064,309 | | Median Employee Annual Total Compensation | $117,549 | | CEO to Median Employee Pay Ratio | 69:1 |

  84. Methodology

    | (3) Calculated CEO Pay Ratio. We calculated our median employee’s annual total compensation for 2025 in accordance with SEC rules for preparing the Summary Compensation Table. We compared the median employee’s compensation to our CEO’s annual total compensation in the Summary Compensation Table to determine the pay ratio shown above. |

  85. Methodology

    | (a) SEC rules permit us to omit the employees of a newly-acquired business from the pay ratio calculation for the fiscal year in which the acquisition occurs. Accordingly, the 624 employees at Enterprise Solutions as of December 31, 2025 were excluded from the employee population. |