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Investments in Unconsolidated Affiliates (Investments in Symetra) (Details) (USD $)
In Millions, except Per Share data, unless otherwise specified
3 Months Ended 6 Months Ended
Jun. 30, 2014
Jun. 30, 2013
Jun. 30, 2014
Jun. 30, 2013
Changes in carrying value of investment in Symetra        
Carrying value at the beginning of the period     $ 321.4  
Equity in earnings 12.5 7.1 26.3 16.3
Carrying value at the end of the period 419.1   419.1  
Income Tax Expense (Benefit) 23.9 (0.6) 54.2 41.0
Symetra
       
Changes in carrying value of investment in Symetra        
Carrying value at the beginning of the period 369.0 377.5 317.3 381.5
Equity in earnings 13.1 7.2 27.5 17.0
Equity in net unrealized losses from Symetra's fixed maturity portfolio 35.4 (71.8) 74.7 (80.5)
Dividends received (2.0) (1.4) (4.0) (2.8)
Increase (decrease) in value of warrants 0 14.5 0 10.8
Carrying value at the end of the period 415.5 326.0 415.5 326.0
Exercise of warrants 0 0 0 0
Symetra | Common shareholders' equity.
       
Changes in carrying value of investment in Symetra        
Carrying value at the beginning of the period 369.0 350.9 317.3 351.2
Equity in earnings 13.1 7.2 27.5 17.0
Equity in net unrealized losses from Symetra's fixed maturity portfolio 35.4 (71.8) 74.7 (80.5)
Dividends received (2.0) (1.4) (4.0) (2.8)
Increase (decrease) in value of warrants 0 0 0 0
Carrying value at the end of the period 415.5 326.0 415.5 326.0
Aggregate value of White Mountains common shares of Symetra at quoted market price 455.9   455.9  
Share Price $ 22.74   $ 22.74  
Exercise of warrants 0 41.1 0 41.1
Symetra | Warrants
       
Changes in carrying value of investment in Symetra        
Carrying value at the beginning of the period 0 26.6 0 30.3
Equity in earnings 0 0 0 0
Equity in net unrealized losses from Symetra's fixed maturity portfolio 0 0 0 0
Dividends received 0 0 0 0
Increase (decrease) in value of warrants 0 14.5 0 10.8
Carrying value at the end of the period 0 0 0 0
Share Price   $ 15.53   $ 15.53
Exercise of warrants 0 (41.1) 0 (41.1)
White Mountains | Common shareholders' equity.
       
Changes in carrying value of investment in Symetra        
Equity in net unrealized losses from Symetra's fixed maturity portfolio 31.1 (17.8) 31.1 (17.8)
equity in earnings of unconsolidated affiliates | Symetra | Common shareholders' equity.
       
Changes in carrying value of investment in Symetra        
Income Tax Expense (Benefit) 0.9 0.6 1.9 1.4
Net unrealized gains (losses) of unconsolidated affiliates | White Mountains | Common shareholders' equity.
       
Changes in carrying value of investment in Symetra        
Income Tax Expense (Benefit) (2.1) 1.4 (2.1) 1.4
Amortization of common share basis difference | Symetra | Common shareholders' equity.
       
Changes in carrying value of investment in Symetra        
Equity in earnings 0.7 0.7 1.5 1.5
impairment of net unrealized gains (losses) | Net unrealized gains (losses) of unconsolidated affiliates | Symetra | Common shareholders' equity.
       
Changes in carrying value of investment in Symetra        
Equity in net unrealized losses from Symetra's fixed maturity portfolio $ 3.1 $ 2.7 $ 6.3 $ 5.5