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Held for Sale and Discontinued Operations - Financial Statement Disclosure (Details) - USD ($) $ in Millions |  | 3 Months Ended | 9 Months Ended | 12 Months Ended |  |
--- | --- | --- | --- | --- | --- | ---
Aug. 01, 2022 | Sep. 30, 2022 | Sep. 30, 2021 | Sep. 30, 2022 | Sep. 30, 2021 | Dec. 31, 2018 | Dec. 31, 2021 | Dec. 31, 2020
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |  |  |
Net income (loss) from discontinued operations, net of tax - NSM Group |  | $ 6.3 | $ 5.3 | $ 16.4 | $ (23.8) |  |  |
Net gain (loss) from sale of discontinued operations, net of tax |  |  |  | 886.8 | 18.7 |  |  |
Total income (loss) from discontinued operations, net of tax |  | (893.1) | (5.3) | (903.2) | 5.1 |  |  |
Net (income) loss from discontinued operations attributable to non-controlling interests |  | (0.1) | 0.0 | (0.7) | 1.1 |  |  |
Other comprehensive income (loss) from discontinued operations, net of tax - NSM Group |  | 0.7 | (2.2) | (5.2) | 0.9 |  |  |
Net gain (loss) from foreign currency translation from sale of discontinued operations, net of tax - NSM Group |  | 2.9 | 0.0 | 2.9 | 0.0 |  |  |
Net Cash Provided by (Used in) Discontinued Operations [Abstract] |  |  |  |  |  |  |  |
Net cash provided from (used for) operations |  |  |  | 38.7 | 40.3 |  |  |
Net cash provided from (used for) investing activities |  |  |  | 7.1 | (54.6) |  |  |
Net cash used from (used for) financing activities |  |  |  | (17.5) | 13.8 |  |  |
Net change in cash during the period |  |  |  | 98.0 | 99.4 |  |  |
Cash balances at beginning of period (includes restricted cash balances of $4.5 and $0.0 and excludes discontinued operations cash balances of $111.6 and $126.6) |  |  |  | 147.7 | 84.6 |  |  |
Cash balances at end of period (includes restricted cash balances of $8.9 and $4.0 and excludes discontinued operations cash balances of $0.0 and 126.7) |  | 245.7 | 184.0 | 245.7 | 184.0 |  |  |
Restricted cash balance |  | 8.9 | 4.0 | 8.9 | 4.0 |  | $ 4.5 | $ 0.0
Interest paid |  |  |  | (10.9) | (5.3) |  |  |
Net income tax payments |  |  |  | 3.2 | 2.1 |  |  |
NSM Insurance Group |  |  |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |  |  |
Net gain (loss) from sale of discontinued operations, net of tax |  | 886.8 | 0.0 | 886.8 | 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 |  |  |
Sirius Group |  |  |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |  |  |
Net gain (loss) from sale of discontinued operations, net of tax |  | 0.0 | 0.0 | 0.0 | 18.7 | $ 17.3 |  |
Discontinued Operations, Held-for-sale | NSM Insurance Group |  |  |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Balance Sheet Disclosures [Abstract] |  |  |  |  |  |  |  |
Short-term investments, at fair value |  |  |  |  |  |  | 7.8 |
Cash (restricted $89.2) |  |  |  |  |  |  | 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 |  | 26.6 | 67.0 | 176.9 | 194.6 |  |  |
Other revenues |  | 7.0 | 15.3 | 48.1 | 46.8 |  |  |
Total revenues - NSM Group |  | 33.6 | 82.3 | 225.0 | 241.4 |  |  |
General and administrative expenses |  | 15.7 | 48.9 | 126.8 | 142.4 |  |  |
Broker commission expenses |  | 8.2 | 20.4 | 52.9 | 60.9 |  |  |
Change in fair value of contingent consideration |  | 0.0 | 0.6 | 0.1 | 0.8 |  |  |
Amortization of other intangible assets |  | 0.0 | 8.2 | 9.1 | 25.0 |  |  |
Loss on assets held for sale |  | 0.0 | 0.0 | 0.0 | (28.7) |  |  |
Interest expense |  | 1.6 | 5.9 | 12.1 | 17.7 |  |  |
Total expenses - NSM Group |  | 25.5 | 84.0 | 201.0 | 275.5 |  |  |
Pre-tax income (loss) from discontinued operations - NSM Group |  | 8.1 | (1.7) | 24.0 | (34.1) |  |  |
Income tax (expense) benefit |  | (1.8) | 7.0 | (7.6) | 10.3 |  |  |
Net income (loss) from discontinued operations, net of tax - NSM Group |  | 6.3 | 5.3 | 16.4 | (23.8) |  |  |
Net gain (loss) from sale of discontinued operations, net of tax |  | 886.8 | 0.0 | 886.8 | 0.0 |  |  |
Total income (loss) from discontinued operations, net of tax |  | 893.1 | 5.3 | 903.2 | (5.1) |  |  |
Net (income) loss from discontinued operations attributable to non-controlling interests |  | (0.2) | 0.0 | (0.8) | 1.1 |  |  |
Total income (loss) from discontinued operations attributable to White Mountains’s common shareholders |  | 892.9 | 5.3 | 902.4 | (4.0) |  |  |
Other comprehensive income (loss) from discontinued operations, net of tax - NSM Group |  | 0.7 | (1.7) | (5.2) | 0.9 |  |  |
Comprehensive income (loss) from discontinued operations |  | 896.5 | 3.6 | 900.1 | (3.1) |  |  |
Other comprehensive income (loss) from discontinued operations attributable to non-controlling interests |  | (0.1) | 0.0 | 0.2 | (0.1) |  |  |
Comprehensive income (loss) from discontinued operations attributable to White Mountains’s common shareholders |  | 896.4 | 3.6 | 900.3 | (3.2) |  |  |
Net Cash Provided by (Used in) Discontinued Operations [Abstract] |  |  |  |  |  |  |  |
Net cash provided from (used for) operations |  |  |  | 38.7 | 40.3 |  |  |
Net cash provided from (used for) investing activities |  |  |  | 7.1 | (54.6) |  |  |
Net cash used from (used for) financing activities |  |  |  | (17.5) | 13.8 |  |  |
Effect of exchange rate changes on cash |  |  |  | 4.0 | 0.6 |  |  |
Net change in cash during the period |  |  |  | 32.3 | 0.1 |  |  |
Cash balances at beginning of period (includes restricted cash balances of $4.5 and $0.0 and excludes discontinued operations cash balances of $111.6 and $126.6) |  |  |  | 111.6 | 126.6 |  |  |
Cash sold as part of the sale of NSM Group (includes restricted cash of $105.1 and $0.0) |  |  |  | (143.9) | 0.0 |  |  |
Cash balances at end of period (includes restricted cash balances of $8.9 and $4.0 and excludes discontinued operations cash balances of $0.0 and 126.7) |  | 0.0 | 126.7 | 0.0 | 126.7 |  |  |
Restricted cash balance |  | 0.0 | 92.2 | 0.0 | 92.2 |  | $ 89.2 | 78.4
Interest paid |  |  |  | (12.0) | (16.6) |  |  |
Net income tax payments |  |  |  | 0.0 | 0.0 |  |  |
Discontinued Operations, Held-for-sale | Sirius Group |  |  |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |  |  |
Net gain (loss) from sale of discontinued operations, net of tax |  | 0.0 | 0.0 | 0.0 | 18.7 |  |  |
Discontinued Operations, Disposed of by Sale | NSM Insurance Group |  |  |  |  |  |  |  |
Disposal Group, Including Discontinued Operation, Income Statement Disclosures [Abstract] |  |  |  |  |  |  |  |
Loss on assets held for sale | $ (875.7) |  |  |  |  |  |  |
Net gain (loss) from sale of discontinued operations, net of tax | 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 | $ 105.1 | 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] |  |  |  |  |  |  |  |
Net gain (loss) from sale of discontinued operations, net of tax |  |  |  |  | $ 17.6 |  |  |

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