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Earnings Per Share - Schedule of Undistributed Net Earnings (Details) - USD ($) $ in Millions | 12 Months Ended
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Dec. 31, 2023 | Dec. 31, 2022 | Dec. 31, 2021
Earnings Per Share [Abstract] |  |  |
Net income (loss) attributable to White Mountains’s common shareholders, net of restricted common share amounts | $ 502.0 | $ (108.4) | $ (269.3)
Dividends declared, net of restricted common share amounts | (2.5) | (3.0) | (3.1)
Total undistributed net earnings (losses), net of restricted common share amounts | $ 499.5 | $ (111.4) | $ (272.4)

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