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Segmented Information - Product Line (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2018
Dec. 31, 2017
Disclosure of products and services [line items]    
Net earned premium $ 12,066.0 $ 9,721.4
Interest and dividends 783.5 559.0
Share of profit of associates 221.1 200.5
Net gains on investments 252.9 1,467.5
Gain on sale of subsidiary 0.0 1,018.6
Other revenue 4,434.2 3,257.6
Income 17,757.7 16,224.6
Property    
Disclosure of products and services [line items]    
Net earned premium 4,103.8 3,185.6
Casualty    
Disclosure of products and services [line items]    
Net earned premium 6,786.3 5,500.5
Specialty    
Disclosure of products and services [line items]    
Net earned premium 1,175.9 1,035.3
Operating companies    
Disclosure of products and services [line items]    
Net earned premium 11,661.4 9,701.3
Interest and dividends 544.1 402.3
Share of profit of associates 93.7 23.5
Net gains on investments (524.7) 1,558.3
Gain on sale of subsidiary   1,018.6
Other revenue 0.0 0.0
Operating companies | Property    
Disclosure of products and services [line items]    
Net earned premium 4,103.8 3,185.6
Operating companies | Casualty    
Disclosure of products and services [line items]    
Net earned premium 6,397.2 5,477.6
Operating companies | Specialty    
Disclosure of products and services [line items]    
Net earned premium 1,160.4 1,038.1
Reportable segments | Runoff    
Disclosure of products and services [line items]    
Net earned premium 404.6 20.1
Interest and dividends 43.7 28.9
Share of profit of associates 0.8 (6.1)
Net gains on investments (107.6) 73.3
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Reportable segments | Property | Runoff    
Disclosure of products and services [line items]    
Net earned premium 0.0 0.0
Reportable segments | Casualty | Runoff    
Disclosure of products and services [line items]    
Net earned premium 389.1 22.9
Reportable segments | Specialty | Runoff    
Disclosure of products and services [line items]    
Net earned premium $ 15.5 $ (2.8)
Product Concentration | Net Premiums Earned | Property    
Disclosure of products and services [line items]    
Allocation of net premiums earned 34.00% 32.80%
Product Concentration | Net Premiums Earned | Casualty    
Disclosure of products and services [line items]    
Allocation of net premiums earned 56.30% 56.60%
Product Concentration | Net Premiums Earned | Specialty    
Disclosure of products and services [line items]    
Allocation of net premiums earned 9.70% 10.60%
Northbridge | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium $ 1,119.2 $ 1,019.7
Interest and dividends 67.0 54.1
Share of profit of associates 6.3 3.2
Net gains on investments (55.6) 44.8
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Northbridge | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 490.3 449.1
Northbridge | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 523.2 474.4
Northbridge | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 105.7 96.2
Odyssey Group | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 2,755.4 2,333.4
Interest and dividends 139.9 124.9
Share of profit of associates 65.8 7.2
Net gains on investments (111.4) 253.1
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Odyssey Group | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,398.3 1,206.0
Odyssey Group | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,099.2 901.5
Odyssey Group | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 257.9 225.9
Crum & Forster | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,960.9 1,852.8
Interest and dividends 64.6 33.8
Share of profit of associates 4.1 (1.1)
Net gains on investments (144.2) 27.9
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Crum & Forster | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 253.9 238.9
Crum & Forster | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,623.6 1,518.0
Crum & Forster | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 83.4 95.9
Zenith National | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 804.3 811.6
Interest and dividends 32.3 23.4
Share of profit of associates 4.4 (9.8)
Net gains on investments (57.6) 26.6
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Zenith National | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 35.5 32.1
Zenith National | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 768.8 779.5
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 1,479.7 1,536.9
Interest and dividends 55.3 32.6
Share of profit of associates 5.3 9.2
Net gains on investments (63.1) 79.0
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Brit | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 490.7 427.1
Brit | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 618.5 755.7
Brit | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 370.5 354.1
Allied World | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 2,286.8 1,028.7
Interest and dividends 117.2 65.9
Share of profit of associates (3.8) (17.6)
Net gains on investments (66.9) (26.5)
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Allied World | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 794.5 360.9
Allied World | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,362.4 607.4
Allied World | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 129.9 60.4
Fairfax Asia | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 189.5 327.6
Fairfax Asia | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 75.7 65.6
Fairfax Asia | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 93.0 219.2
Fairfax Asia | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 20.8 42.8
Other | Operating companies | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 1,065.6 790.6
Interest and dividends 46.7 38.5
Share of profit of associates 16.7 3.0
Net gains on investments 45.8 69.5
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Other | Operating companies | Property | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 564.9 405.9
Other | Operating companies | Casualty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium 308.5 221.9
Other | Operating companies | Specialty | Insurance and Reinsurance    
Disclosure of products and services [line items]    
Net earned premium $ 192.2 $ 162.8