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SCHEDULE II CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT - Statement of Operations and Comprehensive Income (Details) - USD ($)
$ in Millions
 3 Months Ended 12 Months Ended
Dec. 31, 2020
Sep. 30, 2020
Jun. 30, 2020
Mar. 31, 2020
Dec. 31, 2019
Sep. 30, 2019
Jun. 30, 2019
Mar. 31, 2019
Dec. 31, 2020
Dec. 31, 2019
Dec. 31, 2018
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
Revenues (loss) (including realized and unrealized gains and losses) $ 520.8 $ 459.5 $ 259.6 $ (59.2) $ 175.3 $ 155.5 $ 129.0 $ 433.6 $ 1,180.7 $ 893.4 $ 369.1
Expenses 163.5 138.3 126.9 106.8 118.8 104.4 113.2 151.9 535.5 488.3 547.3
Pre-tax income (loss) 357.3 321.2 132.7 (166.0) 56.5 51.1 15.8 281.7 645.2 405.1 (178.2)
Income tax benefit (expense) 117.6 (98.5) (24.1) 25.5 (10.4) (8.8) 0.1 (10.2) 20.5 (29.3) 4.0
Net income (loss) from continuing operations 474.9 222.7 108.6 (140.5) 46.1 42.3 15.9 271.5 665.7 375.8 (174.2)
Net income from discontinued operations, net of tax (1.5) (0.7) (1.0) 0.9 (0.8) 0.9 0.0 0.7      
Net loss attributable to non-controlling interests 15.8 10.9 7.8 10.8 15.6 5.5 4.6 12.2 45.3 37.9 50.2
Net income (loss) attributable to White Mountains’s common shareholders $ 489.2 $ 232.9 $ 115.4 $ (128.8) $ 60.9 $ 48.7 $ 20.5 $ 284.4 708.7 414.5 (141.2)
Other comprehensive income (loss), net of tax                 7.3 (1.4) (4.8)
Comprehensive income (loss) attributable to White Mountains’s common shareholders                 715.5 413.1 (145.7)
White Mountains Insurance Group Ltd.                      
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
Revenues (loss) (including realized and unrealized gains and losses)                 (8.7) 65.0 (47.7)
Expenses                 61.0 47.1 45.9
Pre-tax income (loss)                 (69.7) 17.9 (93.6)
Income tax benefit (expense)                 0.3 0.9 2.5
Net income (loss) from continuing operations                 (70.0) 17.0 (96.1)
Net income from discontinued operations, net of tax                 (2.3) 0.8 (17.2)
Equity in earnings from consolidated and unconsolidated subsidiaries, net of tax                 782.0 398.5 (27.4)
Net loss attributable to non-controlling interests                 (1.0) (1.8) (0.5)
Net income (loss) attributable to White Mountains’s common shareholders                 708.7 414.5 (141.2)
Other comprehensive income (loss), net of tax                 6.8 (1.4) (4.5)
Comprehensive income (loss) attributable to White Mountains’s common shareholders                 715.5 413.1 (145.7)
Swedish Tax Authority | Sirius Group                      
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
Loss contingency accrual, period increase (decrease)                 (2.3) $ 0.8 $ (17.3)
Swedish Tax Authority | Sirius Group | Sirius Group                      
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
Loss contingency accrual, period increase (decrease)                 $ 2.2