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Selected Quarterly Financial Data (Unaudited) (Details) - USD ($)
$ / shares in Units, $ in Millions
3 Months Ended 12 Months Ended
Dec. 31, 2016
Sep. 30, 2016
Jun. 30, 2016
Mar. 31, 2016
Dec. 31, 2015
Sep. 30, 2015
Jun. 30, 2015
Mar. 31, 2015
Dec. 31, 2016
Dec. 31, 2015
Dec. 31, 2014
Quarterly Financial Information Disclosure [Abstract]                      
(Loss) revenues (including realized gains and losses) $ 268.2 $ 365.0 $ 358.2 $ 369.3 $ 602.6 $ 296.1 $ 368.7 $ 354.3 $ 1,360.7 $ 1,621.7 $ 1,411.1
Total expenses 335.0 345.0 360.3 360.8 356.3 383.0 373.8 351.3 1,401.1 1,464.4 1,440.5
Pre-tax (loss) income from continuing operations (66.8) 20.0 (2.1) 8.5 246.3 (86.9) (5.1) 3.0 (40.4) 157.3 (29.4)
Income Tax Expense (Benefit) 23.0 6.7 6.0 9.7 1.0 1.6 2.2 (4.6) 45.4 0.2 14.8
Net income (loss) from continuing operations (43.8) 26.7 3.9 18.2 247.3 (85.3) (2.9) (1.6) 5.0 157.5 (14.6)
Net (loss) income from discontinued operations, net of tax (6.8) 61.9 358.6 1.1 19.6 6.5 (0.5) 71.3 (0.3) 78.7 260.6
Non-controlling interest in consolidated subsidiaries 17.3 3.1 (21.4) (6.3) (6.1) 16.0 0.9 7.3 (7.3) 18.1 22.2
Equity in earnings of unconsolidated affiliates, net of tax 0.0 0.0 0.0 0.0 7.1 3.9 6.8 7.3 0.0 25.1 45.6
Net income attributable to White Mountains’s common shareholders $ (33.3) $ 91.7 $ 341.1 $ 13.0 $ 267.9 $ (58.9) $ 4.3 $ 84.3 $ 412.5 $ 297.6 $ 312.2
Basic earnings per share                      
Continuing operations $ (5.81) $ 6.12 $ (3.44) $ 2.51 $ 43.82 $ (11.10) $ 0.80 $ 1.76 $ (0.47) $ 34.12 $ 8.70
Discontinued operations (1.49) 12.72 70.37 (0.17) 3.46 1.09 (0.08) 12.33 82.71 16.48 42.43
Total consolidated operations (7.30) 18.84 66.93 2.34 47.28 (10.01) 0.72 14.09 82.24 50.60 51.13
Diluted earnings per share                      
Continuing operations (5.81) 6.11 (3.43) 2.51 43.79 (11.10) 0.80 1.76 (0.47) 34.12 8.70
Discontinued operations (1.49) 12.69 70.22 (0.17) 3.46 1.09 (0.08) 12.33 82.66 16.48 42.43
Total consolidated operations $ (7.30) $ 18.80 $ 66.79 $ 2.34 $ 47.25 $ (10.01) $ 0.72 $ 14.09 $ 82.19 $ 50.60 $ 51.13