Earnings Per Share (Details) (USD $) In Millions, except Share data, unless otherwise specified	3 Months Ended		9 Months Ended
	Sep. 30, 2014	Sep. 30, 2013	Sep. 30, 2014	Sep. 30, 2013
Basic and diluted earnings per share numerators (in millions):
Net income (loss) attributable to White Mountains’ common shareholders	$ 44.8	$ 56.8	$ 233.9	$ 199.1
Allocation of income for unvested restricted common shares	(0.6)	(0.9)	(3.0)	(2.9)
Dividends declared on participating restricted common shares	0	0	(0.1)	(0.1)
Total allocation to restricted common shares	(0.6)	(0.9)	(3.1)	(3.0)
Net income attributable to White Mountains’s common shareholders, net of restricted common share amounts	44.2	55.9	230.8	196.1
Undistributed net earnings (in millions):
Net income attributable to White Mountains’s common shareholders, net of restricted common share amounts	44.2	55.9	230.8	196.1
Dividends declared net of restricted common share amounts	0	0	(6.0)	(6.1)
Total undistributed net earnings, net of restricted common share amounts	44.2	55.9	224.8	190.0
Basic earnings per share denominators
Total average common shares outstanding during the period	6,091,500	6,176,600	6,140,900	6,208,400
Average unvested restricted common shares	(81,300)	(95,500)	(77,700)	(90,000)
Basic earnings per share denominator	6,010,200	6,081,100	6,063,200	6,118,400
Diluted earnings per share denominator
Total average common shares outstanding during the period	6,091,500	6,176,600	6,140,900	6,208,400
Average unvested restricted common shares	(81,300)	(95,500)	(77,700)	(90,000)
Average outstanding dilutive options to acquire common shares	0	0	0	0
Diluted earnings (loss) per share denominator	6,010,200	6,081,100	6,063,200	6,118,400
Basic earnings per share (in dollars):
Net income (loss) attributable to White Mountains' common shareholders	$ 7.35	$ 9.20	$ 38.07	$ 32.05
Dividends declared	$ 0.00	$ 0.00	$ (1.00)	$ (1.00)
Undistributed earnings (loss) (in dollars per share)	$ 7.35	$ 9.20	$ 37.07	$ 31.05
Earnings Per Share, Diluted [Abstract]
Net income (loss) attributable to White Mountains' common shareholders (in dollars per share)	$ 7.35	$ 9.20	$ 38.07	$ 32.05
Dividends declared	$ 0.00	$ 0.00	$ (1.00)	$ (1.00)
Undistributed earnings (loss) (in dollars per share)	$ 7.35	$ 9.20	$ 37.07	$ 31.05
Incremental Common Shares Attributable to Dilutive Effect of Share-based Payment Arrangements	125,000	125,000	125,000	125,000
Segment, Discontinued Operations
Basic and diluted earnings per share numerators (in millions):
Allocation of income for unvested restricted common shares	$ (0.1)	$ 0	$ (0.1)	$ 0
Basic earnings per share denominators
Total average common shares outstanding during the period	6,091,500	6,176,600	6,140,900	6,208,400
Average unvested restricted common shares	(81,300)	(95,500)	(77,700)	(90,000)
Basic earnings per share denominator	6,010,200	6,081,100	6,063,200	6,118,400
Diluted earnings per share denominator
Total average common shares outstanding during the period	6,091,500	6,176,600	6,140,900	6,208,400
Average unvested restricted common shares	(81,300)	(95,500)	(77,700)	(90,000)
Average outstanding dilutive options to acquire common shares	0	0	0	0
Diluted earnings (loss) per share denominator	6,010,200	6,081,100	6,063,200	6,118,400
Earnings Per Share, Diluted [Abstract]
Incremental Common Shares Attributable to Dilutive Effect of Share-based Payment Arrangements				125,000