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Earnings Per Share (Details) (USD $)
In Millions, except Share data, unless otherwise specified
3 Months Ended 12 Months Ended
Dec. 31, 2014
Sep. 30, 2014
Jun. 30, 2014
Mar. 31, 2014
Dec. 31, 2013
Sep. 30, 2013
Jun. 30, 2013
Mar. 31, 2013
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Earnings Per Share [Abstract]                      
Net income (loss) attributable to White Mountains’ common shareholders                 $ 316.1us-gaap_IncomeLossFromContinuingOperations $ 317.3us-gaap_IncomeLossFromContinuingOperations $ 322.4us-gaap_IncomeLossFromContinuingOperations
Basic and diluted earnings per share numerators (in millions):                      
Allocation of income for unvested restricted common shares(1)                 (4.1)wtm_IncomeLossAllocatedToParticipatingUnvestedRestrictedCommonShares (4.7)wtm_IncomeLossAllocatedToParticipatingUnvestedRestrictedCommonShares (4.3)wtm_IncomeLossAllocatedToParticipatingUnvestedRestrictedCommonShares
Dividends declared on participating restricted common shares(1)                 (0.1)us-gaap_DividendsShareBasedCompensation (0.1)us-gaap_DividendsShareBasedCompensation (0.1)us-gaap_DividendsShareBasedCompensation
Total allocation to restricted common shares                 (4.2)wtm_AggregateAllocationToRestrictedSharesIncludingDividend (4.8)wtm_AggregateAllocationToRestrictedSharesIncludingDividend (4.4)wtm_AggregateAllocationToRestrictedSharesIncludingDividend
Net income attributable to White Mountains’s common shareholders, net of restricted common share amounts                 311.9wtm_IncomeLossFromContinuingOperatingsExcludingPortionAttributableToNoncontrollingInterestNet 312.5wtm_IncomeLossFromContinuingOperatingsExcludingPortionAttributableToNoncontrollingInterestNet 318.0wtm_IncomeLossFromContinuingOperatingsExcludingPortionAttributableToNoncontrollingInterestNet
Undistributed net earnings (in millions):                      
Net income attributable to White Mountains’s common shareholders, net of restricted common share amounts                 311.9wtm_IncomeLossFromContinuingOperatingsExcludingPortionAttributableToNoncontrollingInterestNet 312.5wtm_IncomeLossFromContinuingOperatingsExcludingPortionAttributableToNoncontrollingInterestNet 318.0wtm_IncomeLossFromContinuingOperatingsExcludingPortionAttributableToNoncontrollingInterestNet
Dividends declared net of restricted common share amounts(1)                 (6.1)wtm_DividendsCommonStockCashNetOfRestrictedCommonShareAmounts (6.1)wtm_DividendsCommonStockCashNetOfRestrictedCommonShareAmounts (6.5)wtm_DividendsCommonStockCashNetOfRestrictedCommonShareAmounts
Total undistributed net earnings, net of restricted common share amounts                 $ 305.8us-gaap_UndistributedEarnings $ 306.4us-gaap_UndistributedEarnings $ 311.5us-gaap_UndistributedEarnings
Basic earnings per share denominators (in thousands):                      
Total average common shares outstanding during the period                 6,104,900us-gaap_WeightedAverageNumberOfSharesIssuedBasic 6,200,400us-gaap_WeightedAverageNumberOfSharesIssuedBasic 6,799,800us-gaap_WeightedAverageNumberOfSharesIssuedBasic
Average unvested restricted common shares                 (78,900)us-gaap_WeightedAverageNumberOfSharesRestrictedStock (91,400)us-gaap_WeightedAverageNumberOfSharesRestrictedStock (91,100)us-gaap_WeightedAverageNumberOfSharesRestrictedStock
Basic earnings per share denominator                 6,026,000us-gaap_WeightedAverageNumberOfSharesOutstandingBasic 6,109,000us-gaap_WeightedAverageNumberOfSharesOutstandingBasic 6,708,700us-gaap_WeightedAverageNumberOfSharesOutstandingBasic
Diluted earnings per share denominator (in thousands):                      
Total average common shares outstanding during the period                 6,104,900us-gaap_WeightedAverageNumberOfSharesIssuedBasic 6,200,400us-gaap_WeightedAverageNumberOfSharesIssuedBasic 6,799,800us-gaap_WeightedAverageNumberOfSharesIssuedBasic
Average unvested restricted common shares                 (78,900)us-gaap_WeightedAverageNumberOfSharesRestrictedStock (91,400)us-gaap_WeightedAverageNumberOfSharesRestrictedStock (91,100)us-gaap_WeightedAverageNumberOfSharesRestrictedStock
Average outstanding dilutive options to acquire common shares                 0us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustment 0us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustment 0us-gaap_WeightedAverageNumberDilutedSharesOutstandingAdjustment
Diluted earnings (loss) per share denominator                 6,026,000us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding 6,109,000us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding 6,708,700us-gaap_WeightedAverageNumberOfDilutedSharesOutstanding
Basic earnings per share (in dollars):                      
Net income attributable to White Mountains’s common shareholders $ 13.71us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 7.35us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 15.10us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 15.56us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 19.14us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 9.20us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 3.62us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 19.10us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 51.77us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 51.15us-gaap_IncomeLossFromContinuingOperationsPerBasicShare $ 47.41us-gaap_IncomeLossFromContinuingOperationsPerBasicShare
Dividends declared and paid                 $ (1.00)us-gaap_CommonStockDividendsPerShareDeclared $ (1.00)us-gaap_CommonStockDividendsPerShareDeclared $ (1.00)us-gaap_CommonStockDividendsPerShareDeclared
Undistributed earnings                 $ 50.77us-gaap_EarningsPerShareBasicUndistributed $ 50.15us-gaap_EarningsPerShareBasicUndistributed $ 46.41us-gaap_EarningsPerShareBasicUndistributed
Diluted earnings per share (in dollars)                      
Net income attributable to White Mountains’s common shareholders $ 13.71us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 7.35us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 15.10us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 15.56us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 19.14us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 9.20us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 3.62us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 19.10us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 51.77us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 51.15us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare $ 47.41us-gaap_IncomeLossFromContinuingOperationsPerDilutedShare
Dividends declared and paid                 $ (1.00)us-gaap_CommonStockDividendsPerShareDeclared $ (1.00)us-gaap_CommonStockDividendsPerShareDeclared $ (1.00)us-gaap_CommonStockDividendsPerShareDeclared
Undistributed earnings                 $ 50.77us-gaap_EarningsPerShareDilutedUndistributed $ 50.15us-gaap_EarningsPerShareDilutedUndistributed $ 46.41us-gaap_EarningsPerShareDilutedUndistributed
Incremental common shares attributable to share-based payment arrangements                 125,000us-gaap_IncrementalCommonSharesAttributableToShareBasedPaymentArrangements