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Segmented Information - Product Line (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2019
Dec. 31, 2018
Disclosure of products and services [line items]    
Net earned premium $ 13,229.7 $ 12,066.0
Interest and dividends 880.2 783.5
Share of profit (loss) of associates 169.6 221.1
Net gains on investments 1,716.2 252.9
Other revenue 5,537.1 4,434.2
Income 21,532.8 17,757.7
Property    
Disclosure of products and services [line items]    
Net earned premium 4,575.8 4,103.8
Casualty    
Disclosure of products and services [line items]    
Net earned premium 7,374.2 6,786.3
Specialty    
Disclosure of products and services [line items]    
Net earned premium 1,279.7 1,175.9
Operating companies    
Disclosure of products and services [line items]    
Net earned premium 12,587.6 11,661.4
Interest and dividends 657.0 544.1
Share of profit (loss) of associates 56.0 93.7
Net gains on investments 1,258.5 (524.7)
Other revenue 0.0 0.0
Operating companies | Property    
Disclosure of products and services [line items]    
Net earned premium 4,472.0 4,103.8
Operating companies | Casualty    
Disclosure of products and services [line items]    
Net earned premium 6,995.0 6,397.2
Operating companies | Specialty    
Disclosure of products and services [line items]    
Net earned premium 1,120.6 1,160.4
Reportable segments | Runoff    
Disclosure of products and services [line items]    
Net earned premium 642.1 404.6
Interest and dividends 55.8 43.7
Share of profit (loss) of associates (6.3) 0.8
Net gains on investments 168.2 (107.6)
Other revenue 0.0 0.0
Reportable segments | Property | Runoff    
Disclosure of products and services [line items]    
Net earned premium 103.8 0.0
Reportable segments | Casualty | Runoff    
Disclosure of products and services [line items]    
Net earned premium 379.2 389.1
Reportable segments | Specialty | Runoff    
Disclosure of products and services [line items]    
Net earned premium $ 159.1 $ 15.5
Product Concentration | Net Premiums Earned    
Disclosure of products and services [line items]    
Allocation of net premiums earned 100.00% 100.00%
Product Concentration | Net Premiums Earned | Property    
Disclosure of products and services [line items]    
Allocation of net premiums earned 34.60% 34.00%
Product Concentration | Net Premiums Earned | Casualty    
Disclosure of products and services [line items]    
Allocation of net premiums earned 55.70% 56.30%
Product Concentration | Net Premiums Earned | Specialty    
Disclosure of products and services [line items]    
Allocation of net premiums earned 9.70% 9.70%
Northbridge | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium $ 1,240.3 $ 1,119.2
Interest and dividends 65.0 67.0
Share of profit (loss) of associates 1.1 6.3
Net gains on investments 0.5 (55.6)
Other revenue 0.0 0.0
Northbridge | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 538.0 490.3
Northbridge | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 581.4 523.2
Northbridge | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 120.9 105.7
Odyssey Group | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 3,179.2 2,755.4
Interest and dividends 175.9 139.9
Share of profit (loss) of associates 55.1 65.8
Net gains on investments 149.5 (111.4)
Other revenue 0.0 0.0
Odyssey Group | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,598.8 1,398.3
Odyssey Group | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,288.2 1,099.2
Odyssey Group | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 292.2 257.9
Crum & Forster | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 2,193.8 1,960.9
Interest and dividends 85.9 64.6
Share of profit (loss) of associates 19.1 4.1
Net gains on investments 75.2 (144.2)
Other revenue 0.0 0.0
Crum & Forster | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 293.8 253.9
Crum & Forster | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,771.6 1,623.6
Crum & Forster | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 128.4 83.4
Zenith National | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 735.0 804.3
Interest and dividends 33.1 32.3
Share of profit (loss) of associates (16.4) 4.4
Net gains on investments 22.5 (57.6)
Other revenue 0.0 0.0
Zenith National | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 39.1 35.5
Zenith National | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 695.9 768.8
Zenith National | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 0.0 0.0
Brit | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,641.9 1,479.7
Interest and dividends 73.5 55.3
Share of profit (loss) of associates (2.4) 5.3
Net gains on investments 62.1 (63.1)
Other revenue 0.0 0.0
Brit | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 494.3 490.7
Brit | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 844.3 618.5
Brit | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 303.3 370.5
Allied World | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 2,335.4 2,286.8
Interest and dividends 148.9 117.2
Share of profit (loss) of associates 13.3 (3.8)
Net gains on investments 210.2 (66.9)
Other revenue 0.0 0.0
Allied World | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 832.1 794.5
Allied World | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,394.1 1,362.4
Allied World | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 109.2 129.9
Fairfax Asia | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 215.2 189.5
Fairfax Asia | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 74.7 75.7
Fairfax Asia | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 113.7 93.0
Fairfax Asia | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 26.8 20.8
Other | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,046.8 1,065.6
Interest and dividends 57.0 46.7
Share of profit (loss) of associates (13.7) 16.7
Net gains on investments 106.2 45.8
Other revenue 0.0 0.0
Other | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 601.2 564.9
Other | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 305.8 308.5
Other | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium $ 139.8 $ 192.2