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Earnings Per Share - Undistributed Net Earnings From Continuing Operations (Details) - USD ($)
$ in Millions
3 Months Ended 6 Months Ended
Jun. 30, 2023
Jun. 30, 2022
Jun. 30, 2023
Jun. 30, 2022
Earnings Per Share [Abstract]        
Net income (loss) attributable to White Mountains’s common shareholders, net of restricted common share amounts $ 19.3 $ (172.9) $ 196.4 $ (143.7)
Dividends declared net of restricted common share amounts 0.0 0.0 (2.5) (3.0)
Total undistributed net earnings (losses), net of restricted common share amounts $ 19.3 $ (172.9) $ 193.9 $ (146.7)