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Investments in Unconsolidated Affiliates (Investments in Symetra) (Details) - USD ($)
$ / shares in Units, $ in Millions
3 Months Ended 6 Months Ended 10 Months Ended 12 Months Ended
Dec. 31, 2015
Sep. 30, 2015
Jun. 30, 2015
Mar. 31, 2015
Dec. 31, 2014
Sep. 30, 2014
Jun. 30, 2014
Mar. 31, 2014
Jun. 30, 2013
Nov. 05, 2015
Dec. 31, 2015
Dec. 31, 2014
Dec. 31, 2013
Changes in carrying value of investment in Symetra                          
Equity in earnings of unconsolidated affiliates, net of tax $ 7.1 $ 3.9 $ 6.8 $ 7.3 $ 12.3 $ 7.0 $ 12.5 $ 13.8     $ 25.1 $ 45.6 $ 36.6
Net change in pre-tax unrealized gains (losses) on investments in unconsolidated affiliates                     (39.2) 81.2 (106.4)
Carrying value at the end of the period 0.0       414.4         $ 392.8 0.0 414.4  
Tax benefit (expense) $ 1.5 $ 1.6 $ 2.2 $ (4.6) 26.2 $ 4.7 $ (7.1) $ (9.0)     $ 0.7 14.8 (32.6)
Symetra                          
Changes in carrying value of investment in Symetra                          
Equity in earnings of unconsolidated affiliates, net of tax                   25.1   47.0 37.8
Net change in pre-tax unrealized gains (losses) on investments in unconsolidated affiliates                   (39.2)   81.2 (106.4)
Dividends received                   (16.9)   (34.1) (6.4)
Increase (decrease) in value of warrants                         10.8
Carrying value at the end of the period         411.4         392.8   411.4 317.3
Unrealized (losses) gains from Symetra’s fixed maturity portfolio         37.6         (1.6)   37.6  
Exercise of warrants                         0.0
Common Stock | Symetra                          
Changes in carrying value of investment in Symetra                          
Equity in earnings of unconsolidated affiliates, net of tax                   25.1   47.0 37.8
Net change in pre-tax unrealized gains (losses) on investments in unconsolidated affiliates                   (39.2)   81.2 (106.4)
Carrying value of a distribution                   12.4      
Dividends received                   (16.9)   (34.1) (6.4)
Increase (decrease) in value of warrants                         0.0
Carrying value at the end of the period         411.4         392.8   411.4 317.3
Loss from dilutive effect resulting from dividend and issuance of restricted shares                   (0.1)   (0.1) 0.2
Aggregate value of White Mountains common shares of Symetra at quoted market price                   $ 651.2      
Share Price                   $ 31.67      
Exercise of warrants                         41.1
Common Stock | White Mountains                          
Changes in carrying value of investment in Symetra                          
Net change in pre-tax unrealized gains (losses) on investments in unconsolidated affiliates                   $ (1.6)   37.6 (43.6)
Warrants                          
Changes in carrying value of investment in Symetra                          
Increase (decrease) in value of warrants                 $ 10.8        
Warrants | Symetra                          
Changes in carrying value of investment in Symetra                          
Equity in earnings of unconsolidated affiliates, net of tax                   0.0   0.0 0.0
Net change in pre-tax unrealized gains (losses) on investments in unconsolidated affiliates                   0.0   0.0 0.0
Dividends received                   0.0   0.0 0.0
Increase (decrease) in value of warrants                         10.8
Carrying value at the end of the period         $ 0.0         0.0   0.0 $ 0.0
Share Price                         $ 11.49
Exercise of warrants                         $ (41.1)
equity in earnings of unconsolidated affiliates [Member] | Common Stock | Symetra                          
Changes in carrying value of investment in Symetra                          
Tax benefit (expense)                   (1.6)   (3.3) (2.8)
Net unrealized gains (losses) of unconsolidated affiliates [Member] | Common Stock | Symetra                          
Changes in carrying value of investment in Symetra                          
Tax benefit (expense)                   2.9   (5.9) 8.3
Net unrealized gains (losses) of unconsolidated affiliates [Member] | Common Stock | White Mountains                          
Changes in carrying value of investment in Symetra                          
Tax benefit (expense)                   0.2   (2.7) 3.2
impairment of equity in earnings [Member] | equity in earnings of unconsolidated affiliates [Member] | Common Stock | Symetra                          
Changes in carrying value of investment in Symetra                          
Equity in earnings of unconsolidated affiliates, net of tax                         3.0
impairment of net unrealized gains (losses) [Member] | Net unrealized gains (losses) of unconsolidated affiliates [Member] | Common Stock | Symetra                          
Changes in carrying value of investment in Symetra                          
Net change in pre-tax unrealized gains (losses) on investments in unconsolidated affiliates                   9.4   12.7 $ 11.8
Amortization of common share basis difference [Member] | Common Stock | Symetra                          
Changes in carrying value of investment in Symetra                          
Equity in earnings of unconsolidated affiliates, net of tax                   $ 2.3   $ 3.0