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Earnings Per Share - Undistributed Net Earnings (Details) - USD ($)
$ in Millions
3 Months Ended 12 Months Ended
Sep. 30, 2018
Sep. 30, 2017
Dec. 31, 2017
Dec. 31, 2016
Earnings Per Share [Abstract]        
Net income attributable to White Mountains’s common shareholders, net of restricted common share amounts $ 57.3 $ 22.7 $ 13.3 $ 31.1
Dividends declared net of restricted common share amounts 0.0 0.0 (3.7) (4.5)
Total undistributed net losses, net of restricted common share amounts $ 57.3 $ 22.7 $ 9.6 $ 26.6