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Investment Securities (Fair Value Measurements) (Details) (Details) (USD $)
In Millions, unless otherwise specified
3 Months Ended
Mar. 31, 2015
Dec. 31, 2014
Investments, Debt and Equity Securities [Abstract]    
Maximum percentage of price difference provided by pricing services 5.00%wtm_MaximumPercentageDifferencesBetweenPricesProvidedByPricingServicesConsideredOutliers  
Maximum price difference provided by pricing services $ 1.0wtm_MaximumDifferencesBetweenPricesProvidedByPricingServicesConsideredOutliers  
Fair value, investment-related liabilities $ 38.8us-gaap_FinancialInstrumentsSoldNotYetPurchasedAtFairValue $ 38.0us-gaap_FinancialInstrumentsSoldNotYetPurchasedAtFairValue