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Earnings Per Share - Basic and Diluted Earnings Per Share from Continuing Operations (Details) - USD ($)
$ / shares in Units, $ in Millions
 3 Months Ended
Mar. 31, 2021
Mar. 31, 2020
Basic and diluted loss per share numerators (in millions):    
Net loss attributable to White Mountains’s common shareholders $ (75.3) $ (128.8)
Less: total income from discontinued operations, net of tax 18.7 0.9
Net loss from continuing operations attributable to White Mountains’s common shareholders (94.0) (129.7)
Allocation of (earnings) losses to participating restricted common shares 0.9 1.3
Basic and diluted losses per share numerators $ (93.1) $ (128.4)
Basic loss per share denominators (in thousands):    
Total average common shares outstanding during the period (in shares) 3,100,200 3,178,000.0
Average unvested restricted common shares (in shares) (32,400) (33,800)
Basic earnings (losses) per share denominator (in shares) 3,067,800 3,144,200
Diluted loss per share denominator (in thousands):    
Total average common shares outstanding during the period (in shares) 3,100,200 3,178,000.0
Average unvested restricted common shares (in shares) (32,400) (33,800)
Diluted earnings (losses) per share denominator (in shares) 3,067,800 3,144,200
Basic and diluted losses per share (in dollars) - continuing operations:    
Distributed earnings - dividends declared and paid (in USD per share) $ 1.00 $ 1.00
Undistributed earnings (losses) (in USD per share) (31.33) (41.82)
Basic and diluted earnings (losses) per share (in USD per share) $ (30.33) $ (40.82)