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Selected Quarterly Financial Data (Unaudited) (Details) - USD ($)
$ / shares in Units, $ in Millions
 3 Months Ended 12 Months Ended
Dec. 31, 2019
Sep. 30, 2019
Jun. 30, 2019
Mar. 31, 2019
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Quarterly Financial Information Disclosure [Abstract]                      
Revenues $ 175.3 $ 155.5 $ 129.0 $ 433.6 $ 6.0 $ 198.7 $ 122.3 $ 42.1 $ 893.4 $ 369.1 $ 373.8
Expenses 118.8 104.4 113.2 151.9 150.1 154.4 134.7 108.1 488.3 547.3 366.0
Pre-tax income (loss) 56.5 51.1 15.8 281.7 (144.1) 44.3 (12.4) (66.0) 405.1 (178.2) 7.8
Tax (expense) benefit (10.4) (8.8) 0.1 (10.2) 3.6 3.6 (2.5) (0.7) (29.3) 4.0 7.8
Net income (loss) from continuing operations 46.1 42.3 15.9 271.5 (140.5) 47.9 (14.9) (66.7) 375.8 (174.2) 15.6
Net income from discontinued operations, net of tax (0.8) 0.9 0.0 0.7 0.0 (17.3) 0.0 0.1 0.0 0.0 20.5
Non-controlling interest in consolidated subsidiaries 15.6 5.5 4.6 12.2 3.0 10.2 18.4 18.6 37.9 50.2 34.1
Net income attributable to White Mountains’s common shareholders $ 60.9 $ 48.7 $ 20.5 $ 284.4 $ (137.5) $ 40.8 $ 3.5 $ (48.0) $ 414.5 $ (141.2) $ 627.2
Basic earnings (loss) per share                      
Continuing operations $ 19.37 $ 15.01 $ 6.44 $ 89.42 $ (43.24) $ 18.27 $ 1.02 $ (12.85) $ 130.02 $ (36.67) $ 11.56
Discontinued operations (0.25) 0.28 0 0.22 0 (5.44) 0 0.03 0.25 (5.09) 134.50
Total consolidated operations 19.12 15.29 6.44 89.64 (43.24) 12.83 1.02 (12.82) 130.27 (41.76) 146.06
Diluted earnings (loss) per share                      
Continuing operations 19.37 15.01 6.44 89.42 (43.24) 18.27 1.02 (12.85) 130.02 (36.67) 11.56
Discontinued operations (0.25) 0.28 0 0.22 0 (5.44) 0 0.03 0.25 (5.09) 134.50
Total consolidated operations $ 19.12 $ 15.29 $ 6.44 $ 89.64 $ (43.24) $ 12.83 $ 1.02 $ (12.82) $ 130.27 $ (41.76) $ 146.06