Discontinued Operations (Earnings Per Share) (Details) (USD $) In Millions, except Share data, unless otherwise specified	3 Months Ended				6 Months Ended
	Jun. 30, 2013		Jun. 30, 2012		Jun. 30, 2013		Jun. 30, 2012
Basic and diluted earnings (loss) per share numerators (in millions):
Net income (loss) attributable to White Mountains’ common shareholders	$ 22.4		$ 25.6		$ 142.3		$ 128.7
Income (Loss) Allocated to Participating Unvested Restricted Common Shares	(0.4)		(0.4)		(2.0)		(1.6)
Net income attributable to White Mountains' common shareholders, net of restricted common share amounts	26.3		26.1		146.7		119.9
Basic earnings (loss) per share denominators (in thousands):
Total average common shares outstanding during the period	6,176,200		6,638,700		6,224,500		7,033,000
Average unvested restricted common shares	(95,400)	[1],[2]	(93,500)	[1],[3]	(87,200)	[1],[2]	(85,900)	[1]
Basic earnings (loss) per share denominator	6,080,800		6,545,200		6,137,300		6,947,100
Diluted (loss) earnings per share denominator (in thousands):
Total average common shares outstanding during the period	6,176,200		6,638,700		6,224,500		7,033,000
Average unvested restricted common shares	(95,400)	[1],[2]	(93,500)	[1],[3]	(87,200)	[1],[2]	(85,900)	[1]
Average outstanding dilutive options to acquire common shares	0	[2]	0	[2]	0	[2]	0	[2]
Diluted earnings (loss) per share denominator	6,080,800		6,545,200		6,137,300		6,947,100
Segment, Discontinued Operations
Basic and diluted earnings (loss) per share numerators (in millions):
Net income (loss) attributable to White Mountains’ common shareholders	3.9		0.5		4.4		(8.8)
Income (Loss) Allocated to Participating Unvested Restricted Common Shares	0	[4]	0	[4]	0	[4]	0.1	[4]
Net income attributable to White Mountains' common shareholders, net of restricted common share amounts	$ 3.9	[5]	$ 0.5	[5]	$ 4.4	[5]	$ (8.7)	[5]
Basic earnings (loss) per share denominators (in thousands):
Total average common shares outstanding during the period	6,176,200		6,638,700		6,224,500		7,033,000
Average unvested restricted common shares	(95,400)		(93,500)		(87,200)		(85,900)	[3]
Basic earnings (loss) per share denominator	6,080,800		6,545,200		6,137,300		6,947,100
Diluted (loss) earnings per share denominator (in thousands):
Total average common shares outstanding during the period	6,176,200		6,638,700		6,224,500		7,033,000
Average unvested restricted common shares	(95,400)		(93,500)		(87,200)		(85,900)	[3]
Average outstanding dilutive options to acquire common shares	0	[6]	0	[6]	0	[6]	0	[6]
Diluted earnings (loss) per share denominator	6,080,800		6,545,200		6,137,300		6,947,100
Basic and diluted earnings (loss) per share (in dollars):	$ 0.64		$ 0.07		$ 0.71		$ (1.25)

[1] Restricted shares outstanding vest either in equal annual installments or upon a stated date (see Note 13).

[2] The diluted earnings per share denominator for the three and six months ended June 30, 2013 and 2012 do not include common shares issuable upon exercise of the Non-Qualified Options as they are anti-dilutive to the calculation.

[3] Restricted common shares outstanding vest either in equal annual installments or upon a stated date (see Note 13).

[4] Restricted shares issued by White Mountains contain dividend participation features, and therefore, are considered participating securities.

[5] Net earnings (loss) attributable to White Mountains’ common shareholders, net of restricted share amounts, is equal to undistributed earnings (loss) for the three and six months ended June 30, 2013 and 2012.

[6] The diluted earnings (loss) per share denominator for the three and six months ended June 30, 2013 and 2012 do not include common shares issuable upon exercise of the Non-Qualified Options as they are anti-dilutive to the calculation.