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Derivatives (Pre-Tax Operating Results of WM Life Re) (Details) - 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
Pre-tax operating results of WM Life Re                      
Total revenues $ 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
General and administrative expenses                 (299.9) (302.2) (216.5)
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)
White Mountains Life Re                      
Pre-tax operating results of WM Life Re                      
Fees, included in other revenue                 1.2 9.3 18.6
Change in Fair Value of Variable Annuity Liability, included in other revenues                 (0.3) (0.4) 52.9
Change in fair value of derivatives, included in other revenue                 (2.0) (8.8) (72.4)
Foreign exchange, included in other revenue                 1.3 (1.3) (3.2)
Other investment income and losses                 0.0 (0.4) (1.4)
Total revenues                 0.2 (1.6) (5.5)
Change in fair value of variable annuity death benefit liabilities, included in general and administrative expenses                 0.0 0.0 0.6
Death benefit claims paid, included in general and administrative expenses                 (0.3) (0.1) (0.1)
General and administrative expenses                 (2.6) (4.0) (4.3)
Pre-tax (loss) income from continuing operations                 $ (2.7) $ (5.7) (9.3)
Level 3 Inputs | Projected Surrender Assumption [Member] | White Mountains Life Re                      
Pre-tax operating results of WM Life Re                      
Change in fair value of derivatives, included in other revenue                     $ 0.2