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Earnings Per Share - Undistributed Net Earnings From Continuing Operations (Details) - USD ($)
$ in Millions
3 Months Ended
Mar. 31, 2021
Mar. 31, 2020
Earnings Per Share [Abstract]    
Net loss attributable to White Mountains’s common shareholders, net of restricted common share amounts $ (93.1) $ (128.4)
Dividends declared net of restricted common share amounts (3.1) (3.1)
Total undistributed net losses, net of restricted common share amounts $ (96.2) $ (131.5)