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Investments in Unconsolidated Affiliates (Investments in Symetra Table Rollforward) (Details) - USD ($)
3 Months Ended
Mar. 31, 2016
Mar. 31, 2015
Changes in carrying value of investment in Symetra    
Equity in earnings $ 0 $ 7,300,000
Income Tax Expense (Benefit) (8,700,000) 4,600,000
Symetra | Common Stock    
Changes in carrying value of investment in Symetra    
Carrying value at the beginning of the period   411,400,000
Equity in earnings   7,200,000
Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio   30,900,000
Dividends received   (2,200,000)
Carrying value at the end of the period   447,300,000
White Mountains | Common Stock    
Changes in carrying value of investment in Symetra    
Equity in net unrealized gains (losses) from Symetra's fixed maturity portfolio   68,400,000
equity in earnings of unconsolidated affiliates | Symetra | Common Stock    
Changes in carrying value of investment in Symetra    
Income Tax Expense (Benefit)   400,000
Net unrealized gains (losses) of unconsolidated affiliates | White Mountains | Common Stock    
Changes in carrying value of investment in Symetra    
Income Tax Expense (Benefit)   (4,600,000)
Amortization of common share basis difference | Symetra | Common Stock    
Changes in carrying value of investment in Symetra    
Equity in earnings $ 2,015 700,000
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   $ 2,900,000