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Discontinued Operations Earnings Per Share (Details) (USD $)
In Millions, except Share data, unless otherwise specified
3 Months Ended
Mar. 31, 2014
Mar. 31, 2013
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]    
Incremental Common Shares Attributable to Dilutive Effect of Share-based Payment Arrangements 125,000 125,000
Basic and diluted (loss) earnings per share numerators (in millions):    
Income (Loss) Allocated to Participating Unvested Restricted Common Shares $ (1.1) $ (1.5)
Net income attributable to White Mountains' common shareholders, net of restricted common share amounts 95.6 120.4
Basic (loss) earnings per share denominators (in thousands):    
Total average common shares outstanding during the period 6,169,900 6,273,500
Average unvested restricted common shares (70,400) (79,000)
Basic (loss) earnings per share denominator 6,099,500 6,194,500
Diluted (loss) earnings per share denominator (in thousands):    
Total average common shares outstanding during the period 6,169,900 6,273,500
Average unvested restricted common shares (70,400) (79,000)
Average outstanding dilutive options to acquire common shares 0 0
Diluted (loss) earnings per share denominator 6,099,500 6,194,500
Segment, Discontinued Operations
   
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]    
Incremental Common Shares Attributable to Dilutive Effect of Share-based Payment Arrangements 125,000 125,000
Basic and diluted (loss) earnings per share numerators (in millions):    
Income (Loss) from Discontinued Operations, Net of Tax, Attributable to Parent (0.5) 0.5
Income (Loss) Allocated to Participating Unvested Restricted Common Shares 0 0
Net income attributable to White Mountains' common shareholders, net of restricted common share amounts $ (0.5) $ 0.5
Basic (loss) earnings per share denominators (in thousands):    
Total average common shares outstanding during the period 6,169,900 6,273,500
Average unvested restricted common shares (70,400) (79,000)
Basic (loss) earnings per share denominator 6,099,500 6,194,500
Diluted (loss) earnings per share denominator (in thousands):    
Total average common shares outstanding during the period 6,169,900 6,273,500
Average unvested restricted common shares (70,400) (79,000)
Average outstanding dilutive options to acquire common shares 0 0
Diluted (loss) earnings per share denominator 6,099,500 6,194,500
Basic and diluted (loss) earnings per share (in dollars): $ (0.08) $ 0.07