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Investments in Unconsolidated Affiliates (Investments in Symetra) (Details) - USD ($)
$ / shares in Units, $ in Millions
3 Months Ended 10 Months Ended 12 Months Ended
Nov. 05, 2015
Dec. 31, 2014
Dec. 31, 2016
Sep. 30, 2016
Jun. 30, 2016
Mar. 31, 2016
Dec. 31, 2015
Sep. 30, 2015
Jun. 30, 2015
Mar. 31, 2015
Nov. 05, 2015
Dec. 31, 2016
Dec. 31, 2015
Dec. 31, 2014
Changes in carrying value of investment in Symetra                            
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 change in pre-tax unrealized investment (losses) gains on investments in unconsolidated affiliates                       0.0 (39.2) 81.2
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
Common shares, issued shares     4,563,814       5,623,735         4,563,814 5,623,735  
Common Stock | Symetra                            
Changes in carrying value of investment in Symetra                            
Equity in earnings of unconsolidated affiliates, net of tax                     $ 25.1      
Net change in pre-tax unrealized investment (losses) gains on investments in unconsolidated affiliates                     (39.2)      
Carrying value of a distribution                     12.4      
Dividends received                     (16.9)      
Carrying value at the end of the period $ 392.8 $ 411.4                 392.8     411.4
Loss from dilutive effect resulting from dividend and issuance of restricted shares                     (0.1)      
Aggregate value of White Mountains common shares of Symetra at quoted market price $ 651.2                   $ 651.2      
Share Price $ 31.67                   $ 31.67      
Common Stock | White Mountains                            
Changes in carrying value of investment in Symetra                            
Net change in pre-tax unrealized investment (losses) gains on investments in unconsolidated affiliates $ (1.6) $ 37.6                        
equity in earnings of unconsolidated affiliates [Member] | Common Stock | Symetra                            
Changes in carrying value of investment in Symetra                            
Income Tax Expense (Benefit)                     $ (1.6)      
Net unrealized gains (losses) of unconsolidated affiliates [Member] | Common Stock | Symetra                            
Changes in carrying value of investment in Symetra                            
Income Tax Expense (Benefit)                     2.9      
Net unrealized gains (losses) of unconsolidated affiliates [Member] | Common Stock | White Mountains                            
Changes in carrying value of investment in Symetra                            
Income Tax Expense (Benefit)                     0.2     $ (2.7)
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 investment (losses) gains on investments in unconsolidated affiliates                     9.4      
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      
Prospector                            
Changes in carrying value of investment in Symetra                            
Common shares, issued shares             513,500           513,500