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Earnings Per Share (Schedule of Undistributed Net Earnings) (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Earnings Per Share [Abstract]      
Net income (loss) attributable to White Mountains’s common shareholders, net of restricted common share amounts $ 408.4 $ (122.6) $ 49.0
Dividends declared, net of restricted common share amounts (3.2) (3.7) (4.5)
Total undistributed net earnings (losses), net of restricted common share amounts $ 405.2 $ (126.3) $ 44.5