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Earnings Per Share (Details) - USD ($) $ / shares in Units, $ in Millions	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Basic and diluted earnings per share numerators (in millions):
Net income (loss) attributable to White Mountains’s common shareholders	$ 20.5	$ 3.5	$ 304.9	$ (44.5)
Less: total income (loss) from discontinued operations	0.0	0.0	0.7	0.1
Net income (loss) from continuing operations attributable to White Mountains’s common shareholders	20.5	3.5	304.2	(44.6)
Allocation of earnings to participating restricted common shares	(0.3)	0.0	(3.6)	0.4
Basic and diluted earnings (losses) per share numerators	$ 20.2	$ 3.5	$ 300.6	$ (44.2)
Basic earnings per share denominators (in thousands):
Total average common shares outstanding during the period	3,183,500	3,432,000.0	3,177,800	3,588,200
Average unvested restricted common shares	(42,800)	(41,500)	(37,600)	(38,700)
Basic earnings (losses) per share denominator	3,140,700	3,390,500	3,140,200	3,549,500
Diluted earnings per share denominator (in thousands):
Total average common shares outstanding during the period	3,183,500	3,432,000.0	3,177,800	3,588,200
Average unvested restricted common shares	(42,800)	(41,500)	(37,600)	(38,700)
Diluted earnings (losses) per share denominator	3,140,700	3,390,500	3,140,200	3,549,500
Basic earnings per share (in dollars) - continuing operations:
Distributed earnings - dividends declared and paid	$ 0	$ 0	$ 1.00	$ 1.00
Undistributed earnings (losses)	6.44	1.02	94.71	(13.44)
Basic and diluted earnings (losses) per share	$ 6.44	$ 1.02	$ 95.71	$ (12.44)

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