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Earnings Per Share - Undistributed Net Earnings (Details) - USD ($)
$ in Millions
3 Months Ended
Mar. 31, 2020
Mar. 31, 2019
Earnings Per Share [Abstract]    
Net (loss) income attributable to White Mountains’s common shareholders, net of restricted common share amounts $ (128.4) $ 280.8
Dividends declared net of restricted common share amounts (3.1) (3.2)
Total undistributed net (losses) earnings, net of restricted common share amounts $ (131.5) $ 277.6