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Investments in Unconsolidated Affiliates (Investments in Symetra Table Rollforward) (Details) - USD ($)
$ / shares in Units, $ in Millions
3 Months Ended 6 Months Ended
Jun. 30, 2015
Jun. 30, 2014
Jun. 30, 2015
Jun. 30, 2014
Changes in carrying value of investment in Symetra        
Carrying value at the beginning of the period     $ 414.4  
Equity in earnings $ 6.8 $ 12.5 14.1 $ 26.3
Carrying value at the end of the period 397.2   397.2  
Income Tax Expense (Benefit) $ (2.7) 24.5 $ 22.3 55.4
Symetra | Common Stock        
Investments in unconsolidated affiliates        
Share Price $ 24.17   $ 24.17  
Changes in carrying value of investment in Symetra        
Carrying value at the beginning of the period $ 447.3 369.0 $ 411.4 317.3
Equity in earnings 6.1 13.1 13.3 27.5
Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio (66.4) 35.4 (35.5) 74.7
Dividends received (2.2) (2.0) (4.4) (4.0)
Carrying value at the end of the period 397.2 415.5 397.2 415.5
Aggregate value of White Mountains common shares of Symetra at quoted market price 497.0   497.0  
Number of Shares Distributed 12.4 0.0 12.4 0.0
White Mountains | Common Stock        
Changes in carrying value of investment in Symetra        
Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio     2.0 31.1
equity in earnings of unconsolidated affiliates | Symetra | Common Stock        
Changes in carrying value of investment in Symetra        
Income Tax Expense (Benefit) 0.4 0.9 0.8 1.9
Net unrealized gains (losses) of unconsolidated affiliates | White Mountains | Common Stock        
Changes in carrying value of investment in Symetra        
Income Tax Expense (Benefit)     0.0 2.1
Amortization of common share basis difference | Symetra | Common Stock        
Changes in carrying value of investment in Symetra        
Equity in earnings 0.7 0.7 1.4 1.5
impairment of net unrealized gains (losses) | Net unrealized gains (losses) of unconsolidated affiliates | Symetra | Common Stock        
Changes in carrying value of investment in Symetra        
Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio $ 2.8 $ 3.1 $ 5.7 $ 6.3