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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
Mar. 31, 2014
Mar. 31, 2013
Investments in unconsolidated affiliates    
Income Tax Expense (Benefit) $ 30.3 $ 41.6
Changes in carrying value of investment in Symetra    
Carrying value at the beginning of the period 321.4  
Equity in earnings 13.8 9.2
Carrying value at the end of the period 373.3  
Symetra
   
Changes in carrying value of investment in Symetra    
Carrying value at the beginning of the period 317.3 381.5
Equity in earnings 14.4 9.8
Equity in net unrealized losses from Symetra's fixed maturity portfolio 39.3 (8.7)
Dividends received (2.0) (1.4)
Increase (decrease) in value of warrants 0 (3.7)
Carrying value at the end of the period 369.0 377.5
Symetra | Common shareholders' equity.
   
Changes in carrying value of investment in Symetra    
Carrying value at the beginning of the period 317.3 351.2
Equity in earnings 14.4 9.8
Equity in net unrealized losses from Symetra's fixed maturity portfolio 39.3 (8.7)
Dividends received (2.0) (1.4)
Increase (decrease) in value of warrants 0 0
Carrying value at the end of the period 369.0 350.9
Aggregate value of White Mountains common shares of Symetra at quoted market price 397.4  
Share Price $ 19.82  
Symetra | Warrants
   
Changes in carrying value of investment in Symetra    
Carrying value at the beginning of the period 0 30.3
Equity in earnings 0 0
Equity in net unrealized losses from Symetra's fixed maturity portfolio 0 0
Dividends received 0 0
Increase (decrease) in value of warrants 0 (3.7)
Carrying value at the end of the period 0 26.6
Share Price   $ 13.41
White Mountains | Common shareholders' equity.
   
Changes in carrying value of investment in Symetra    
Equity in net unrealized losses from Symetra's fixed maturity portfolio 39.3 (8.7)
equity in earnings of unconsolidated affiliates [Member] | Symetra | Common shareholders' equity.
   
Investments in unconsolidated affiliates    
Income Tax Expense (Benefit) 1.0 0.8
Net unrealized gains (losses) of unconsolidated affiliates [Member] | White Mountains | Common shareholders' equity.
   
Investments in unconsolidated affiliates    
Income Tax Expense (Benefit) (2.8) 0.7
Amortization of common share basis difference [Member] | Symetra | Common shareholders' equity.
   
Changes in carrying value of investment in Symetra    
Equity in earnings 0.7 0.7
impairment of net unrealized gains (losses) [Member] | Net unrealized gains (losses) of unconsolidated affiliates [Member] | 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