| Annual · values | 2025 | 2024 | 2023 | 2022 | 2021 | 2020 | 2019 | 2018 | 2017 | 2016 | 2015 | 2014 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Operating Cash Flow | 550.50 M USD | 586.80 M USD | 404.10 M USD | 365.00 M USD | 38.60 M USD | -60.60 M USD | -120.50 M USD | -31.10 M USD | 94.60 M USD | -155.30 M USD | 175.70 M USD | 118.80 M USD |
| Depreciation & Amortization | 9.00 M USD | -6.40 M USD | -17.80 M USD | 4.30 M USD | 63.60 M USD | 43.40 M USD | 29.80 M USD | 25.70 M USD | 22.40 M USD | 64.50 M USD | 67.50 M USD | 69.70 M USD |
| Stock-Based Compensation | 18.50 M USD | 16.30 M USD | 15.30 M USD | 14.00 M USD | 14.70 M USD | — | — | — | — | — | — | — |
| Capital Expenditures | — | — | — | — | — | — | — | — | — | — | — | — |
| Cash Flow from Investing | -666.90 M USD | -447.00 M USD | -543.90 M USD | 115.50 M USD | -208.30 M USD | 64.60 M USD | -59.90 M USD | 459.20 M USD | 718.50 M USD | 1.28 B USD | 11.30 M USD | 47.90 M USD |
| Cash Flow from Financing | 35.60 M USD | 4.20 M USD | 7.20 M USD | -344.90 M USD | 217.60 M USD | 49.00 M USD | 230.50 M USD | -414.30 M USD | -699.00 M USD | -942.40 M USD | -214.60 M USD | -129.60 M USD |
| Dividends Paid | 2.60 M USD | 2.50 M USD | 2.60 M USD | 3.00 M USD | 3.10 M USD | 3.20 M USD | 3.20 M USD | 3.80 M USD | 4.60 M USD | 5.40 M USD | 6.00 M USD | 6.20 M USD |
| Stock Buybacks | 202.60 M USD | 7.90 M USD | 32.70 M USD | 615.80 M USD | 100.10 M USD | 78.50 M USD | 0 USD | 511.90 M USD | 714.60 M USD | 881.30 M USD | 268.60 M USD | 128.20 M USD |
| Free Cash Flow | — | — | — | — | — | — | — | — | — | — | — | — |
White Mountains Insurance Group Ltd. is a financial services holding company that focuses on businesses in the insurance and related sectors. The company primarily engages in acquiring, operating, and later divesting insurance and financial services platforms through its subsidiaries. Its activities span property and casualty insurance and reinsurance, municipal bond reinsurance, capital solutions for asset and wealth management firms, and property and casualty insurance distribution, as well as other investment-focused operations. Key operating segments include HG Global/BAM, Ark/MW Outrigger, Kudu, and Other Operations, each targeting distinct niches within insurance and financial services. Through these platforms, White Mountains Insurance Group Ltd. provides specialized risk transfer, reinsurance, and capital partnership solutions to institutions, intermediaries, and other market participants. The company was founded in 1980 and is headquartered in Hanover, New Hampshire. In today’s market, it serves as a specialized vehicle for exposure to insurance, reinsurance, and financial services assets, emphasizing opportunistic and value-oriented ownership of those businesses.