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SCHEDULE IV REINSURANCE (Details) (USD $)
In Millions, unless otherwise specified
12 Months Ended
Dec. 31, 2014
Dec. 31, 2013
Dec. 31, 2012
Premiums earned      
Gross amount $ 1,433.7us-gaap_DirectPremiumsEarned    
Ceded to other companies (371.1)us-gaap_CededPremiumsEarned    
Assumed from other companies 996.3us-gaap_AssumedPremiumsEarned    
Net earned premiums 2,058.9us-gaap_PremiumsEarnedNet 1,987.3us-gaap_PremiumsEarnedNet 2,063.6us-gaap_PremiumsEarnedNet
OneBeacon      
Premiums earned      
Gross amount 1,209.1us-gaap_DirectPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,043.3us-gaap_DirectPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,158.3us-gaap_DirectPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Ceded to other companies (102.9)us-gaap_CededPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
(71.4)us-gaap_CededPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
(79.1)us-gaap_CededPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Assumed from other companies 70.9us-gaap_AssumedPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
148.5us-gaap_AssumedPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
52.8us-gaap_AssumedPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Net earned premiums 1,177.1us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,120.4us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
1,132.0us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Percentage of amount assumed to net 6.00%us-gaap_PremiumsPercentageAssumedToNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
13.30%us-gaap_PremiumsPercentageAssumedToNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
4.70%us-gaap_PremiumsPercentageAssumedToNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_OnebeaconMember
Sirius Group      
Premiums earned      
Gross amount 200.2us-gaap_DirectPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
174.0us-gaap_DirectPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
169.9us-gaap_DirectPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Ceded to other companies (251.7)us-gaap_CededPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
(246.2)us-gaap_CededPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
(226.6)us-gaap_CededPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Assumed from other companies 925.4us-gaap_AssumedPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
938.6us-gaap_AssumedPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
988.3us-gaap_AssumedPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Net earned premiums 873.9us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
866.4us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
931.6us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
Percentage of amount assumed to net 105.90%us-gaap_PremiumsPercentageAssumedToNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
108.30%us-gaap_PremiumsPercentageAssumedToNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
106.10%us-gaap_PremiumsPercentageAssumedToNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_SiriusGroupSegmentMember
HG/BAM      
Premiums earned      
Gross amount 1.8us-gaap_DirectPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HGBAMMember
   
Ceded to other companies 0us-gaap_CededPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HGBAMMember
   
Assumed from other companies 0us-gaap_AssumedPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HGBAMMember
   
Net earned premiums 1.8us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HGBAMMember
   
Percentage of amount assumed to net 0.00%us-gaap_PremiumsPercentageAssumedToNet
/ us-gaap_StatementBusinessSegmentsAxis
= wtm_HGBAMMember
   
Other Segments      
Premiums earned      
Gross amount 22.6us-gaap_DirectPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_AllOtherSegmentsMember
   
Ceded to other companies (16.5)us-gaap_CededPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_AllOtherSegmentsMember
   
Assumed from other companies 0us-gaap_AssumedPremiumsEarned
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_AllOtherSegmentsMember
   
Net earned premiums $ 6.1us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_AllOtherSegmentsMember
$ 0us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_AllOtherSegmentsMember
$ 0us-gaap_PremiumsEarnedNet
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_AllOtherSegmentsMember
Percentage of amount assumed to net 0.00%us-gaap_PremiumsPercentageAssumedToNet
/ us-gaap_StatementBusinessSegmentsAxis
= us-gaap_AllOtherSegmentsMember