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White Mountains Insurance Group Ltd. Form 4 Filings

WTM NYSE

Every Form 4 that White Mountains Insurance Group Ltd. (WTM) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.

A Form 4 covers the transactions officers, directors and large holders report, so if you follow WTM and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full WTM filings page.

Rhea-AI Summary

WHITE MOUNTAINS INSURANCE GROUP LTD (WTM) director David Allen Tanner reported a bona fide gift transfer of 2 Common Shares on 2026-08-31. The transaction carried a stated price of $0.00 per share, and his directly held position after the gift was 2,012 Common Shares.

Rhea-AI Summary

WHITE MOUNTAINS INSURANCE GROUP LTD (WTM) reported that a director received an equity award. Reporting person Stephen Klar acquired 113 common shares of WTM on 2026-08-26 as a pro-rated Annual Director Share Award, recorded at a price of $0.00 per share. Following this grant, he holds 113 common shares directly.

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Tanner David Allen reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD director David Allen Tanner received an equity grant of 135 common shares as an annual director share award. The shares were awarded at no cash cost per share and increased his direct holdings to 2,014 common shares following the transaction.

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SHANK SUZANNE F. reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD director Suzanne F. Shank received an annual director share award of 135 Common Shares on May 21, 2026. The grant was at a stated price of $0.00 per share and increased her direct holdings to 1,006 Common Shares.

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Hicks Weston M reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD director Weston M. Hicks received a grant of 190 Common Shares as an annual chairman share award. The shares were awarded at a price of $0.00 per share, indicating they were compensation rather than a market purchase. Following this award, Hicks directly holds 2,936 Common Shares of the company. The filing reflects a routine equity compensation grant to a director, with no open-market buying or selling activity disclosed.

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WHITE MOUNTAINS INSURANCE GROUP LTD director Philip A. Gelston received an annual director share award of 135 common shares on May 21, 2026. The shares were granted at a stated price of $0.00 per share as equity compensation, not a market purchase.

Following this award, Gelston directly holds 1,703 common shares. This Form 4 reflects a routine grant/award acquisition rather than an open‑market buy or sale.

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Dillon Margaret reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD director Margaret Dillon received an annual share award of 135 Common Shares. The grant was recorded at a price of $0.00 per share as compensation, not a market purchase. Following this award, her direct holdings total 1,080 Common Shares.

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Chu John reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD director John Chu received an award of 135 Common Shares as part of an Annual Director Share Award on May 21, 2026. The shares were granted at no cost and are a compensation-related issuance rather than an open-market purchase or sale.

Following this grant, Chu directly holds 335 Common Shares of the company.

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WHITE MOUNTAINS INSURANCE GROUP LTD director Mary C. Choksi received an Annual Director Share Award of 135 Common Shares on May 21, 2026. The shares were granted at $0.00 per share as equity compensation, not as an open-market purchase.

Following this award, Choksi directly holds 1,993 Common Shares of the company. The filing does not show any sales or option exercises, only this routine grant classified as a “grant, award, or other acquisition.”

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WHITE MOUNTAINS INSURANCE GROUP LTD director Peter M. Carlson received an annual director share award in the form of 135 Common Shares on May 21, 2026. The shares were granted at a price of $0.00 per share as compensation, not as an open-market purchase.

Following this award, Carlson directly holds 852 Common Shares of the company. The filing reports no derivative securities and no sales or disposals, only this grant/award acquisition.

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CAMPBELL REID TARLTON reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD director Campbell Reid Tarlton received an equity award of common shares. He was granted 135 common shares as an annual director share award at no purchase price, which is a stock-based component of his board compensation.

After this grant, Tarlton directly holds 10,575 common shares. In addition, he has an indirect holding of 119 common shares through a 401(k) account. The filing does not report any open-market buys or sales, only this compensation-related share award and existing holdings.

Rhea-AI Summary

WHITE MOUNTAINS INSURANCE GROUP LTD executive Robert Lawrence Seelig, EVP & General Counsel, made a bona fide gift of 50 Common Shares on 2026-03-19. The gift carried no sale proceeds. After this transfer, he directly holds 17,857 Common Shares and 2,500 restricted Common Shares, plus 4 Common Shares held indirectly by his wife and dependent children and 583 Common Shares held indirectly through the WTM Retirement Plan.

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WHITE MOUNTAINS INSURANCE GROUP LTD director David Allen Tanner reported a disposition of shares through a bona fide gift. He transferred 225 common shares at a stated price of $0.00 per share on this Form 4. After the gift, he directly owns 1,879 common shares.

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Caffrey Liam P reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD reported that Chief Executive Officer Liam P. Caffrey received a grant of 1,500 restricted common shares on February 25, 2026. The award carries no purchase price and is scheduled to vest on January 1, 2029, functioning as stock-based compensation.

Following this grant, Caffrey directly holds 3,650 common shares in total, which includes both restricted and unrestricted stock, and also has 8 common shares held indirectly through the WTM Retirement Plan. The filing does not show any open‑market buying or selling, only this equity award and updated holdings.

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Harrison Giles E reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD President Giles E. Harrison reported an equity grant in the form of 775 restricted common shares on February 25, 2026. The award carried a grant price of $0.00 per share and is scheduled to vest on January 1, 2029.

After this grant, his directly held common shares increased to 2,675. In addition, he indirectly holds 2 common shares through a company retirement plan account, reflecting accumulation in that plan report dated as of February 25, 2026.

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Hildreth Michaela reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD executive Michaela Hildreth, MD & Chief Accounting Officer, reported receiving a grant of 600 restricted Common Shares on February 25, 2026, at a price of $0.00 per share. The award will vest on January 1, 2029.

After this grant, she directly held 1,825 restricted Common Shares. As of the same date, she also directly held 2,491 Common Shares and indirectly held 20 Common Shares through a 401(k) account.

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Papamichael Michael A reported acquisition or exercise transactions in this Form 4 filing.

WHITE MOUNTAINS INSURANCE GROUP LTD Chief Financial Officer Michael A. Papamichael was granted 500 restricted common shares on February 25, 2026, at a stated price of $0.00 per share. These restricted shares vest on January 1, 2029, and bring his directly held restricted-share balance to 1,200 shares.

As of this transaction date, he also directly held 772 common shares and indirectly held 12 common shares through the White Mountains Retirement Plan, reflecting his broader equity stake in the company.

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SEELIG ROBERT LAWRENCE reported acquisition or exercise transactions in this Form 4 filing.

White Mountains Insurance Group Ltd. executive vice president and general counsel Robert Lawrence Seelig reported receiving an award of 775 restricted common shares on February 25, 2026. The award was granted at no cost and is scheduled to vest on January 1, 2029.

After this grant, he directly held 2,500 restricted common shares and 17,907 other common shares, along with small indirect holdings of 4 common shares through his wife and dependent children and 583 common shares through the White Mountains Retirement Plan.

Rhea-AI Summary

White Mountains Insurance Group executive MD & Chief Accounting Officer reported a routine change in holdings. On January 1, 2026, 600 restricted common shares became unrestricted, and 274 common shares were withheld by the company to cover the reporting person's tax obligations. This withholding is shown as a disposition transaction.

After this event, the reporting person beneficially owned 2,491 common shares and 1,225 restricted common shares directly, plus 20 common shares held indirectly through a 401(k) plan.

Rhea-AI Summary

White Mountains Insurance Group Ltd. Chief Financial Officer, a reporting officer and insider of the company, reported a routine equity transaction. On January 1, 2026, 400 restricted common shares became unrestricted. To cover tax obligations related to this vesting, 131 common shares were withheld by the company, coded as an "F" transaction for tax withholding. After this event, the reporting person beneficially owns 772 common shares directly, 700 restricted common shares directly, and 12 common shares indirectly through the White Mountains Retirement Plan.

Rhea-AI Summary

White Mountains Insurance Group executive vice president and general counsel reported changes in his holdings of the company’s common shares. On January 1, 2026, 1,000 restricted common shares became unrestricted, and 398 of those shares were withheld by the company to cover tax obligations at a reported value of $2,078.03. Following this transaction, he beneficially owns 17,907 common shares directly, 1,725 restricted common shares directly, 4 common shares indirectly through his wife and dependent children, and 583 common shares indirectly through the White Mountains Retirement Plan, which includes an accumulation of 3 shares since his prior report as of a plan statement dated December 22, 2025.

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White Mountains Insurance Group Chief Executive Officer Wesley C. Bell reported changes in his shareholdings in the company. On January 1, 2026, 1,250 restricted common shares became unrestricted, and 425 common shares were withheld by the company to cover his tax obligations at a reported price of $2,078.03. After this transaction, he directly held 1,655 restricted common shares and 2,150 common shares, and indirectly held 8 common shares through the WTM Retirement Plan. The filing is made by a single reporting person in his capacity as Chief Executive Officer.

Rhea-AI Summary

White Mountains Insurance Group Ltd. executive Wesley C. Bell, the MD & Chief Accounting Officer, reported a stock transaction dated December 23, 2025. He disposed of 60 common shares, coded as a "G" transaction, at a reported price of $0, indicating a gift or similar transfer. Following this activity, he beneficially owns 2,165 common shares directly, plus 1,825 restricted common shares directly and 20 common shares held indirectly through a 401(k) account. An accompanying note explains that the 401(k) position reflects the accumulation of 2 common shares in his company retirement account based on a plan report dated December 22, 2025.

Rhea-AI Summary

White Mountains Insurance Group Ltd director reported a stock sale of company shares. On 12/19/2025, the reporting person sold 5,000 common shares in a transaction coded "S" (sale) at a price of $2,050 per share. After this sale, the director beneficially owned 10,440 common shares directly. In addition, 119 common shares were held indirectly through a 401(k) plan. The filing is submitted as a Form 4/A amendment for an earlier report dated 12/22/2025 and reflects the director’s updated ownership position.

Rhea-AI Summary

White Mountains Insurance Group Ltd. reported an insider share transaction by a company director. On 12/19/2025, the reporting person sold 5,000 common shares of the company, coded as a sale transaction. The reported sale price per share is $0. Following this transaction, the director beneficially owns 10,440 common shares directly and an additional 119 shares indirectly through a 401(k) plan. The filing is made by a single reporting person who serves as a director of White Mountains Insurance Group Ltd.

Rhea-AI Summary

White Mountains Insurance Group's chief executive officer and director reported an insider sale of 5,000 common shares on 12/19/2025 at a price of $2,050 per share. Following this transaction, the insider directly owned 13,809 common shares and 5,425 restricted common shares, plus 122 common shares held indirectly through a 401(k) account. The 401(k) balance reflects the accumulation of 2 additional common shares based on a plan report dated as of December 20, 2025.

Rhea-AI Summary

White Mountains Insurance Group Ltd reported that a director disposed of 165 common shares on 12/16/2025, leaving 1,568 shares beneficially owned in direct form.

The transaction is coded "S" in the filing and lists a price of $2,048.51 for the common shares. The report is filed for one reporting person and identifies the filer’s relationship to the company as a director.

Rhea-AI Summary

White Mountains Insurance Group Ltd. (WTM) director reported a small change in personal holdings. On 11/25/2025, the reporting person disposed of 50 common shares at a stated price of $0 under transaction code "G," which typically indicates a gift. Following this transaction, the reporting person beneficially owns 15,440 common shares directly and 119 common shares indirectly through a 401(k) plan. The filing covers only non-derivative equity and shows no derivative securities activity.

Rhea-AI Summary

White Mountains Insurance Group (WTM) director reported a bona fide gift of 4 common shares on November 10, 2025 at $0 (Code G). Following the transaction, the director beneficially owns 2,104 shares, held directly, per Form 4.