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Investments in Unconsolidated Affiliates (Investments in Symetra Table Rollforward) (Details) - USD ($)
$ in Millions
3 Months Ended 6 Months Ended 9 Months Ended
Sep. 30, 2016
Sep. 30, 2015
Jun. 30, 2015
Sep. 30, 2016
Sep. 30, 2015
Changes in carrying value of investment in Symetra          
Equity in earnings $ 0.0 $ 3.9   $ 0.0 $ 18.0
Income Tax Expense (Benefit) $ (6.7) (1.6)   $ (22.4) 0.8
Symetra | Common Stock          
Changes in carrying value of investment in Symetra          
Carrying value at the beginning of the period   397.2 $ 411.4   411.4
Equity in earnings   4.2     17.5
Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio   3.7     (31.8)
Dividends received   (12.5)     (16.9)
Carrying value of a distribution   0.0     12.4
Carrying value at the end of the period   392.6 $ 397.2   392.6
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      
equity in earnings of unconsolidated affiliates | Symetra | Common Stock          
Changes in carrying value of investment in Symetra          
Income Tax Expense (Benefit)   0.3     1.1
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      
Amortization of common share basis difference | Symetra | Common Stock          
Changes in carrying value of investment in Symetra          
Equity in earnings   0.7     2.1
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     $ 8.6