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Third Party Reinsurance (Written and Earned Premiums) (Details) (USD $)
In Millions, unless otherwise specified
 12 Months Ended
Dec. 31, 2013
Dec. 31, 2012
Dec. 31, 2011
Earned premiums:      
Net earned premiums $ 1,987.3 $ 2,063.6 $ 1,924.5
Losses and LAE:      
Total incurred losses and LAE 1,040.5 1,193.9 1,174.3
OneBeacon
      
Written premiums:      
Direct 1,103.1 1,204.0 1,079.2
Assumed 59.8 55.2 49.1
Gross written premiums 1,162.9 1,259.2 1,128.3
Ceded (74.3) (80.0) (65.6)
Net written premiums 1,088.6 1,179.2 1,062.7
Earned premiums:      
Gross amount 1,043.3 [1] 1,158.3 [1] 1,035.9 [1]
Assumed from other companies 148.5 [1] 52.8 [1] 42.3 [1]
Gross earned premiums 1,191.8 1,211.1 1,078.2
Ceded (71.4) [1] (79.1) [1] (66.0) [1]
Net earned premiums 1,120.4 [1] 1,132.0 [1] 1,012.2 [1]
Losses and LAE:      
Direct 584.9 687.5 551.8
Policyholder Benefits and Claims Incurred, Assumed 76.3 29.6 9.2
Gross losses and LAE 661.2 717.1 561.0
Ceded (39.1) (67.1) (12.7)
Total incurred losses and LAE 622.1 650.0 548.3
Sirius Group
      
Written premiums:      
Direct 177.3 186.1 139.5
Assumed 943.1 992.7 988.6
Gross written premiums 1,120.4 1,178.8 1,128.1
Ceded (243.8) (231.1) (212.4)
Net written premiums 876.6 947.7 915.7
Earned premiums:      
Gross amount 174.0 169.9 128.5
Assumed from other companies 938.6 988.3 989.8
Gross earned premiums 1,112.6 1,158.2 1,118.3
Ceded (246.2) (226.6) (206.0)
Net earned premiums 866.4 931.6 912.3
Losses and LAE:      
Direct 98.1 96.9 80.0
Policyholder Benefits and Claims Incurred, Assumed 455.5 523.9 627.8
Gross losses and LAE 553.6 620.8 707.8
Ceded (135.2) (76.9) (81.8)
Total incurred losses and LAE 418.4 543.9 626.0
OneBeacon and Sirius Group
      
Written premiums:      
Direct 1,280.4 1,390.1 1,218.7
Assumed 1,002.9 1,047.9 1,037.7
Gross written premiums 2,283.3 2,438.0 2,256.4
Ceded (318.1) (311.1) (278.0)
Net written premiums 1,965.2 2,126.9 1,978.4
Earned premiums:      
Gross amount 1,217.3 1,328.2 1,164.4
Assumed from other companies 1,087.1 1,041.1 1,032.1
Gross earned premiums 2,304.4 2,369.3 2,196.5
Ceded (317.6) (305.7) (272.0)
Net earned premiums 1,986.8 2,063.6 1,924.5
Losses and LAE:      
Direct 683.0 784.4 631.8
Policyholder Benefits and Claims Incurred, Assumed 531.8 553.5 637.0
Gross losses and LAE 1,214.8 1,337.9 1,268.8
Ceded (174.3) (144.0) (94.5)
Total incurred losses and LAE $ 1,040.5 $ 1,193.9 $ 1,174.3
[1] The amounts shown excludes balances reclassified to held for sale in the consolidated balance sheets related to the Runoff Transaction as of December 31, 2013 and 2012 and to AutoOne as of December 31, 2011. See Note 21 - “Discontinued Operations”.