Earnings Per Share (Details) (USD $) In Millions, except Share data, unless otherwise specified	3 Months Ended
	Mar. 31, 2014	Mar. 31, 2013
Earnings Per Share [Abstract]
Incremental Common Shares Attributable to Dilutive Effect of Share-based Payment Arrangements	125,000	125,000
Basic and diluted earnings per share numerators (in millions):
Net income (loss) attributable to White Mountains’ common shareholders	$ 96.1	$ 119.9
Allocation of income for unvested restricted common shares	(1.1)	(1.5)
Dividends declared on participating restricted common shares	(0.1)	(0.1)
Total allocation to restricted common shares	(1.2)	(1.6)
Net income attributable to White Mountains’s common shareholders, net of restricted common share amounts	94.9	118.3
Undistributed net earnings (in millions):
Net income attributable to White Mountains’s common shareholders, net of restricted common share amounts	94.9	118.3
Dividends declared net of restricted common share amounts	(6.1)	(6.1)
Total undistributed net earnings, net of restricted common share amounts	$ 88.8	$ 112.2
Basic earnings per share denominators
Total average common shares outstanding during the period	6,169,900	6,273,500
Average unvested restricted common shares	(70,400)	(79,000)
Basic earnings per share denominator	6,099,500	6,194,500
Diluted earnings per share denominator
Total average common shares outstanding during the period	6,169,900	6,273,500
Average unvested restricted common shares	(70,400)	(79,000)
Average outstanding dilutive options to acquire common shares	0	0
Diluted earnings (loss) per share denominator	6,099,500	6,194,500
Basic earnings per share (in dollars):
Net income (loss) attributable to White Mountains' common shareholders	$ 15.56	$ 19.10
Dividends declared	$ (1.00)	$ (1.00)
Undistributed earnings (loss) (in dollars per share)	$ 14.56	$ 18.10
Earnings Per Share, Diluted [Abstract]
Net income (loss) attributable to White Mountains' common shareholders (in dollars per share)	$ 15.56	$ 19.10
Dividends declared	$ (1.00)	$ (1.00)
Undistributed earnings (loss) (in dollars per share)	$ 14.56	$ 18.10