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Caffrey Liam P

Disclosed activity across 1 company

Tapewire entity
64359
SEC CIK
0001915424

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
WHITE MOUNTAINS INSURANCE GROUP LTDWTM · Entity 3904Director · Chief Executive OfficerFebruary 25, 2026February 27, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

WHITE MOUNTAINS INSURANCE GROUP LTD

Report date February 25, 2026 · Filed February 27, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common Shares (Restricted)SEC Table I · non-derivativeDirect3,650 Reported balance After 2026-02-25 transaction · row 1
1 source row

Row 1 · 2026-02-25 · Grant · Acquired 1,500 · Balance 3,650

F1: On February 25, 2026, the Reporting Person received a restricted share award of 1,500 Common Shares, which vests on January 1, 2029.

Common SharesSEC Table I · non-derivativeDirect1,655 Reported balance Holding disclosure · report date 2026-02-25 · row 2 Holding and transaction disclosures are not merged.
1 source row

Row 2 · Balance 1,655

Common SharesSEC Table I · non-derivativeIndirectby WTM Retirement Plan8 Reported balance Holding disclosure · report date 2026-02-25 · row 3 Holding and transaction disclosures are not merged.
1 source row

Row 3 · Balance 8

Filing footnotes · ownership attribution and instrument terms

F1: On February 25, 2026, the Reporting Person received a restricted share award of 1,500 Common Shares, which vests on January 1, 2029.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
February 25, 2026 Filed Feb 27, 2026 16:19 UTC WHITE MOUNTAINS INSURANCE GROUP LTD WTM · Entity 3904 GrantCommon Shares (Restricted) 1,500 $0.00 $0.00
Disclosure

SEC source: 0000776867-26-000021 · form4.xml · nonDerivative · entry 1

Caffrey Liam P · CIK 0001915424 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,650

F1 · shares: On February 25, 2026, the Reporting Person received a restricted share award of 1,500 Common Shares, which vests on January 1, 2029.

Read SEC document
January 01, 2026 Filed Jan 2, 2026 23:02 UTC WHITE MOUNTAINS INSURANCE GROUP LTD WTM · Entity 3904 Tax withholdingCommon Shares 425 $2,078.03 $883,162.75
Disclosure

SEC source: 0000776867-26-000006 · form4.xml · nonDerivative · entry 1

Caffrey Liam P · CIK 0001915424 · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,655

F1 · balance_after: On January 1, 2026, 1,250 restricted Common Shares became unrestricted. 425 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations.

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February 26, 2025 Filed Feb 28, 2025 14:32 UTC WHITE MOUNTAINS INSURANCE GROUP LTD WTM · Entity 3904 GrantCommon Shares (restricted) 1,025 $0.00 $0.00
Disclosure

SEC source: 0001062993-25-003865 · form4.xml · nonDerivative · entry 1

Caffrey Liam P · CIK 0001915424 · EVP& Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,400

F1 · shares: On February 26, 2025, the Reporting Person received a restricted share award of 1,025 Common Shares, which vests on January 1, 2028.

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January 01, 2025 Filed Jan 3, 2025 14:22 UTC WHITE MOUNTAINS INSURANCE GROUP LTD WTM · Entity 3904 Tax withholdingCommon Shares 420 $1,945.06 $816,925.20
Disclosure

SEC source: 0001062993-25-000039 · form4.xml · nonDerivative · entry 1

Caffrey Liam P · CIK 0001915424 · President & CFO

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 830

F1 · balance_after: On January 1, 2025, 1,250 restricted Common Shares became unrestricted. 420 of the Common Shares were withheld by the Company to satisfy the Reporting Person's tax obligations.

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February 22, 2024 Filed Feb 24, 2024 02:28 UTC WHITE MOUNTAINS INSURANCE GROUP LTD WTM · Entity 3904 GrantCommon Shares (restricted) 1,125 $0.00 $0.00
Disclosure

SEC source: 0001062993-24-004346 · form4.xml · nonDerivative · entry 1

Caffrey Liam P · CIK 0001915424 · EVP& Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,625

F1 · shares: On February 22, 2024, the Reporting Person received a restricted share award of 1,125 Common Shares, which vests on January 1, 2027.

Read SEC document
February 22, 2023 Filed Feb 24, 2023 14:01 UTC WHITE MOUNTAINS INSURANCE GROUP LTD WTM · Entity 3904 GrantCommon Shares (restricted) 1,250 $0.00 $0.00
Disclosure

SEC source: 0001062993-23-004720 · form4.xml · nonDerivative · entry 1

Caffrey Liam P · CIK 0001915424 · EVP& Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 2,500

F1 · shares: On February 22, 2023, the Reporting Person received a restricted share award of 1,250 Common Shares, which vests on January 1, 2026.

Read SEC document

Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.