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Selected Quarterly Financial Data (Unaudited) (Details) (USD $)
In Millions, except Per 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
Quarterly Financial Information Disclosure [Abstract]                      
Revenues (including realized gains and losses) $ 689.7us-gaap_Revenues $ 589.4us-gaap_Revenues $ 652.8us-gaap_Revenues $ 578.3us-gaap_Revenues $ 626.6us-gaap_Revenues $ 574.1us-gaap_Revenues $ 489.3us-gaap_Revenues $ 627.4us-gaap_Revenues $ 2,510.2us-gaap_Revenues $ 2,317.4us-gaap_Revenues $ 2,435.7us-gaap_Revenues
Total expenses 643.5us-gaap_BenefitsLossesAndExpenses 555.0us-gaap_BenefitsLossesAndExpenses 543.8us-gaap_BenefitsLossesAndExpenses 466.2us-gaap_BenefitsLossesAndExpenses 492.4us-gaap_BenefitsLossesAndExpenses 518.8us-gaap_BenefitsLossesAndExpenses 485.7us-gaap_BenefitsLossesAndExpenses 475.6us-gaap_BenefitsLossesAndExpenses 2,208.5us-gaap_BenefitsLossesAndExpenses 1,972.5us-gaap_BenefitsLossesAndExpenses 2,172.9us-gaap_BenefitsLossesAndExpenses
Pre-tax loss 46.2us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 34.4us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 109.0us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 112.1us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 134.2us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 55.3us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 3.6us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 151.8us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 301.7us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 344.9us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments 262.8us-gaap_IncomeLossFromContinuingOperationsBeforeIncomeTaxesMinorityInterestAndIncomeLossFromEquityMethodInvestments
Tax benefit (expense) 8.7us-gaap_IncomeTaxExpenseBenefit (7.8)us-gaap_IncomeTaxExpenseBenefit (23.9)us-gaap_IncomeTaxExpenseBenefit (30.3)us-gaap_IncomeTaxExpenseBenefit (27.4)us-gaap_IncomeTaxExpenseBenefit (8.2)us-gaap_IncomeTaxExpenseBenefit 0.6us-gaap_IncomeTaxExpenseBenefit (41.6)us-gaap_IncomeTaxExpenseBenefit (53.3)us-gaap_IncomeTaxExpenseBenefit (76.6)us-gaap_IncomeTaxExpenseBenefit 15.7us-gaap_IncomeTaxExpenseBenefit
Net income from continuing operations 54.9us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 26.6us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 85.1us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 81.8us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 106.8us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 47.1us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 4.2us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 110.2us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 248.4us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 268.3us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest 278.5us-gaap_IncomeLossFromContinuingOperationsIncludingPortionAttributableToNoncontrollingInterest
Net loss from discontinued operations, net of tax (12.2)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 6.7us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 2.6us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (0.5)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (0.3)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 0.4us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 3.9us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax 0.5us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (1.8)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (42.1)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax (24.0)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTax
Non-controlling interest in consolidated subsidiaries 15.0us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 11.2us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (4.6)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 0.5us-gaap_NetIncomeLossAttributableToNoncontrollingInterest (0.3)us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 1.1us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 11.1us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 0.5us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 22.1us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 12.4us-gaap_NetIncomeLossAttributableToNoncontrollingInterest 14.0us-gaap_NetIncomeLossAttributableToNoncontrollingInterest
Equity in earnings of unconsolidated affiliates, net of tax 12.3us-gaap_IncomeLossFromEquityMethodInvestments 7.0us-gaap_IncomeLossFromEquityMethodInvestments 12.5us-gaap_IncomeLossFromEquityMethodInvestments 13.8us-gaap_IncomeLossFromEquityMethodInvestments 11.7us-gaap_IncomeLossFromEquityMethodInvestments 8.6us-gaap_IncomeLossFromEquityMethodInvestments 7.1us-gaap_IncomeLossFromEquityMethodInvestments 9.2us-gaap_IncomeLossFromEquityMethodInvestments 45.6us-gaap_IncomeLossFromEquityMethodInvestments 36.6us-gaap_IncomeLossFromEquityMethodInvestments 29.9us-gaap_IncomeLossFromEquityMethodInvestments
Net income attributable to White Mountains’s common shareholders $ 70.0us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 51.5us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 95.6us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 95.6us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 117.9us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 57.2us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 26.3us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 120.4us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 312.7us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 321.8us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic $ 207.4us-gaap_NetIncomeLossAvailableToCommonStockholdersBasic
Basic earnings (loss) per share                      
Continuing operations $ 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
Discontinued operations $ (2.03)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ 1.10us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ 0.43us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ (0.08)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ (0.05)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ 0.06us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ 0.64us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ 0.07us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ (0.56)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ 0.74us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare $ (16.91)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerBasicShare
Total consolidated operations $ 11.68us-gaap_EarningsPerShareBasic $ 8.45us-gaap_EarningsPerShareBasic $ 15.53us-gaap_EarningsPerShareBasic $ 15.48us-gaap_EarningsPerShareBasic $ 19.09us-gaap_EarningsPerShareBasic $ 9.26us-gaap_EarningsPerShareBasic $ 4.26us-gaap_EarningsPerShareBasic $ 19.17us-gaap_EarningsPerShareBasic $ 51.21us-gaap_EarningsPerShareBasic $ 51.89us-gaap_EarningsPerShareBasic $ 30.50us-gaap_EarningsPerShareBasic
Diluted earnings (loss) per share                      
Continuing operations $ 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
Discontinued operations $ (2.03)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ 1.10us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ 0.43us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ (0.08)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ (0.05)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ 0.06us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ 0.64us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ 0.07us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ (0.56)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ 0.74us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare $ (16.91)us-gaap_IncomeLossFromDiscontinuedOperationsNetOfTaxPerDilutedShare
Total consolidated operations $ 11.68us-gaap_EarningsPerShareDiluted $ 8.45us-gaap_EarningsPerShareDiluted $ 15.53us-gaap_EarningsPerShareDiluted $ 15.48us-gaap_EarningsPerShareDiluted $ 19.09us-gaap_EarningsPerShareDiluted $ 9.26us-gaap_EarningsPerShareDiluted $ 4.26us-gaap_EarningsPerShareDiluted $ 19.17us-gaap_EarningsPerShareDiluted $ 51.21us-gaap_EarningsPerShareDiluted $ 51.89us-gaap_EarningsPerShareDiluted $ 30.50us-gaap_EarningsPerShareDiluted