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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 9 Months Ended
Sep. 30, 2015
Sep. 30, 2014
Jun. 30, 2015
Jun. 30, 2014
Sep. 30, 2015
Sep. 30, 2014
Changes in carrying value of investment in Symetra            
Carrying value at the beginning of the period     $ 414.4   $ 414.4  
Equity in earnings $ 3.9 $ 7.0     18.0 $ 33.3
Carrying value at the end of the period 392.6       392.6  
Income Tax Expense (Benefit) $ (1.6) (4.7)     $ 0.8 11.4
Symetra | Common Stock            
Investments in unconsolidated affiliates            
Share Price $ 31.64       $ 31.64  
Changes in carrying value of investment in Symetra            
Carrying value at the beginning of the period $ 397.2 415.5 411.4 $ 317.3 $ 411.4 317.3
Equity in earnings 4.2 7.0     17.5 34.5
Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio 3.7 (10.7)     (31.8) 64.0
Dividends received (12.5) (2.0)     (16.9) (6.0)
Carrying value at the end of the period 392.6 409.8 $ 397.2 $ 415.5 392.6 409.8
Aggregate value of White Mountains common shares of Symetra at quoted market price 650.6       650.6  
Number of Shares Distributed 0.0 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         5.7 20.5
equity in earnings of unconsolidated affiliates | Symetra | Common Stock            
Changes in carrying value of investment in Symetra            
Income Tax Expense (Benefit) 0.3 0.5     1.1 2.4
Net unrealized gains (losses) of unconsolidated affiliates | White Mountains | Common Stock            
Changes in carrying value of investment in Symetra            
Income Tax Expense (Benefit)         0.2 1.4
Amortization of common share basis difference | Symetra | Common Stock            
Changes in carrying value of investment in Symetra            
Equity in earnings 0.7 0.7     2.1 2.2
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 $ 2.9 $ 3.1     $ 8.6 $ 9.4