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Held for Sale and Discontinued Operations - Financial Statement Disclosure (Details) - USD ($) $ in Millions |  | 12 Months Ended |
--- | --- | --- | ---
Aug. 01, 2022 | Dec. 31, 2022 | Dec. 31, 2021 | Dec. 31, 2020 | Dec. 31, 2018 | Dec. 31, 2019
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |
Net income (loss) from discontinued operations, net of tax - NSM Group |  | $ 16.4 | $ (22.6) | $ (9.5) |  |
Total income (loss) from discontinued operations attributable to White Mountains’s common shareholders |  | (903.2) | 3.9 | 11.8 |  |
Net (income) loss from discontinued operations attributable to non-controlling interests |  | (0.7) | 1.0 | 0.2 |  |
Other comprehensive income (loss) from discontinued operations, net of tax - NSM Group |  | (5.2) | 0.2 | 5.9 |  |
Net gain (loss) from foreign currency translation from sale of discontinued operations, net of tax - NSM Group |  | 2.9 | 0.0 | 0.0 |  |
Net Cash Provided by (Used in) Discontinued Operations [Abstract] |  |  |  |  |  |
Net cash provided from (used for) operations |  | 38.7 | 42.3 | 35.5 |  |
Net cash provided from (used for) investing activities |  | 7.1 | (56.5) | (124.9) |  |
Net cash used from (used for) financing activities |  | (17.5) | (1.0) | 128.8 |  |
Net decrease in cash during the year |  | 107.3 | 63.1 | 13.6 |  |
Cash balance at beginning of year |  | 147.7 | 84.6 | 71.0 |  |
Cash balance at end of year |  | 255.0 | 147.7 | 84.6 |  |
Net income tax payments to US |  | 10.3 | (0.1) | 15.9 |  |
NSM |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |
Net income (loss) from discontinued operations, net of tax - NSM Group |  | 16.4 | (22.6) | (9.5) |  |
Gain (loss) on sale of discontinued operations |  | 886.8 | 0.0 | 0.0 |  |
Net Cash Provided by (Used in) Discontinued Operations [Abstract] |  |  |  |  |  |
Cash sold as part of the sale of NSM Group (includes restricted cash of $105.1 and $0.0) |  | (143.9) | (0.0) | (0.0) |  |
Sirius Group |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |
Gain (loss) on sale of discontinued operations |  | 0.0 | 18.7 | (2.3) |  |
Held for Sale |  |  |  |  |  |
Net Cash Provided by (Used in) Discontinued Operations [Abstract] |  |  |  |  |  |
Restricted cash balance |  | 0.0 | 89.2 | 78.4 |  | $ 56.3
Held for Sale | NSM |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Balance Sheet Disclosures [Abstract] |  |  |  |  |  |
Short-term investments, at fair value |  |  | 7.8 |  |  |
Cash held for sale |  |  | 111.6 |  |  |
Restricted cash |  |  | 89.2 |  |  |
Premiums and commissions receivable |  |  | 85.0 |  |  |
Goodwill and other intangible assets |  |  | 725.4 |  |  |
Other assets |  |  | 59.2 |  |  |
Total assets held for sale |  |  | 989.0 |  |  |
Debt |  |  | 272.1 |  |  |
Premiums payable |  |  | 135.9 |  |  |
Contingent consideration |  |  | 6.8 |  |  |
Other liabilities |  |  | 80.5 |  |  |
Total liabilities held for sale |  |  | 495.3 |  |  |
Net assets held for sale |  |  | 493.7 |  |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |
Commission revenues |  | 176.9 | 258.0 | 232.5 |  |
Other revenues |  | 48.1 | 72.4 | 52.6 |  |
Total revenues - NSM Group |  | 225.0 | 330.4 | 285.1 |  |
General and administrative expenses |  | 126.8 | 190.4 | 179.5 |  |
Broker commission expenses |  | 52.9 | 80.2 | 75.3 |  |
Change in fair value of contingent consideration |  | 0.1 | 1.0 | (3.3) |  |
Amortization of other intangible assets |  | 9.1 | 35.2 | 26.7 |  |
Loss on assets held for sale |  | 0.0 | (28.7) | 0.0 |  |
Interest expense |  | 12.1 | 23.3 | 22.1 |  |
Total expenses - NSM Group |  | 201.0 | 358.8 | 300.3 |  |
Pre-tax income (loss) from discontinued operations - NSM Group |  | 24.0 | (28.4) | (15.2) |  |
Income tax (expense) benefit |  | (7.6) | 5.8 | 5.7 |  |
Net income (loss) from discontinued operations, net of tax - NSM Group |  | 16.4 | (22.6) | (9.5) |  |
Gain (loss) on sale of discontinued operations |  | 886.8 | 0.0 | 0.0 |  |
Total income (loss) from discontinued operations attributable to White Mountains’s common shareholders |  | 903.2 | (3.9) | (11.8) |  |
Net (income) loss from discontinued operations attributable to non-controlling interests |  | (0.7) | 1.0 | 0.2 |  |
Total income (loss) from discontinued operations attributable to White Mountains’s common shareholders |  | 902.5 | (2.9) | (11.6) |  |
Other comprehensive income (loss) from discontinued operations, net of tax - NSM Group |  | (5.2) | 0.2 | 5.9 |  |
Comprehensive income (loss) from discontinued operations |  | 900.2 | (2.7) | (5.7) |  |
Other comprehensive income (loss) from discontinued operations attributable to non-controlling interests |  | 0.2 | (0.1) | (0.3) |  |
Comprehensive income (loss) from discontinued operations attributable to White Mountains’s common shareholders |  | 900.4 | (2.8) | (6.0) |  |
Net Cash Provided by (Used in) Discontinued Operations [Abstract] |  |  |  |  |  |
Net cash provided from (used for) operations |  | 38.7 | 42.3 | 35.5 |  |
Net cash provided from (used for) investing activities |  | 7.1 | (56.5) | (124.9) |  |
Net cash used from (used for) financing activities |  | (17.5) | (1.0) | 128.8 |  |
Effect of exchange rate changes on cash |  | 4.0 | 0.2 | (2.8) |  |
Net decrease in cash during the year |  | 32.3 | (15.0) | 36.6 |  |
Cash balance at beginning of year |  | 111.6 | 126.6 | 90.0 |  |
Cash sold as part of the sale of NSM Group (includes restricted cash of $105.1 and $0.0) |  | (143.9) | 0.0 | 0.0 |  |
Cash balance at end of year |  | 0.0 | 111.6 | 126.6 |  |
Interest paid |  | (12.0) | (16.6) | (20.9) |  |
Net income tax payments to US |  | 0.0 | 0.0 | 0.0 |  |
Held for Sale | Sirius Group |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |
Gain (loss) on sale of discontinued operations |  | 0.0 | 18.7 | (2.3) |  |
Discontinued Operations, Disposed of by Sale | NSM |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |
Loss on assets held for sale | $ (875.7) |  |  |  |  |
Gain (loss) on sale of discontinued operations | 886.8 |  |  |  |  |
Net gain (loss) from foreign currency translation from sale of discontinued operations, net of tax - NSM Group | $ 2.9 |  |  |  |  |
Net Cash Provided by (Used in) Discontinued Operations [Abstract] |  |  |  |  |  |
Restricted cash balance |  | $ 105.1 | 0.0 | 0.0 |  |
Discontinued Operations, Disposed of by Sale | Sirius Group |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Balance Sheet Disclosures [Abstract] |  |  |  |  |  |
Total liabilities held for sale |  |  |  | $ 18.7 |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |
Gain (loss) on sale of discontinued operations |  |  | $ 17.6 |  | $ 17.3 |

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