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SCHEDULE II CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT (Details 2) - USD ($)
$ 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
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
Fair value investments $ 5,039.7       $ 4,050.9       $ 5,039.7 $ 4,050.9 $ 3,343.6
(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
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 (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
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
Comprehensive income attributable to White Mountains’ common shareholders                 557.8 197.2 210.6
Computation of net income (loss) available to common shareholders:                      
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
White Mountains Insurance Group Ltd.                      
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
(Loss) revenues (including realized gains and losses)                 (1.0) 5.0 0.3
Expenses                 68.2 59.9 32.3
Pre-tax loss                 (69.2) (54.9) (32.0)
Income Tax Expense (Benefit)                 (0.5) 0.0 0.9
Net income (loss) from continuing operations                 (69.7) (54.9) (31.1)
Net (loss) income from discontinued operations, net of tax                 0.0 0.0 13.9
Equity in earnings (losses) from consolidated and unconsolidated affiliates                 482.2 352.5 329.4
Net income attributable to White Mountains’s common shareholders                 412.5 297.6 312.2
Other comprehensive income (loss), after-tax                 145.3 (100.4) (101.6)
Comprehensive income attributable to White Mountains’ common shareholders                 557.8 197.2 210.6
Computation of net income (loss) available to common shareholders:                      
Net income attributable to White Mountains’s common shareholders                 412.5 297.6 $ 312.2
Fair value measured on a recurring basis                      
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
Fair value investments 5,195.9       4,134.4       5,195.9 4,134.4  
Level 3 | Fair value measured on a recurring basis                      
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
Fair value investments 177.7       $ 239.5       177.7 $ 239.5  
Level 3 | Forward Contracts [Member] | Fair value measured on a recurring basis                      
CONDENSED FINANCIAL INFORMATION OF THE REGISTRANT                      
Fair value investments $ (1.2)               $ (1.2)