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Segmented Information - Geographic Region (Details) - USD ($)
$ in Millions
12 Months Ended
Dec. 31, 2018
Dec. 31, 2017
Disclosure of geographical areas [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 (losses) 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
Canada    
Disclosure of geographical areas [line items]    
Net earned premium 1,306.9 1,196.8
United States    
Disclosure of geographical areas [line items]    
Net earned premium 7,466.8 6,148.7
Asia    
Disclosure of geographical areas [line items]    
Net earned premium 917.0 822.7
International    
Disclosure of geographical areas [line items]    
Net earned premium 2,375.3 1,553.2
Operating companies    
Disclosure of geographical areas [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 (losses) on investments (524.7) 1,558.3
Gain on sale of subsidiary   1,018.6
Other revenue 0.0 0.0
Operating companies | Canada    
Disclosure of geographical areas [line items]    
Net earned premium 1,306.9 1,196.8
Operating companies | United States    
Disclosure of geographical areas [line items]    
Net earned premium 7,460.5 6,125.0
Operating companies | Asia    
Disclosure of geographical areas [line items]    
Net earned premium 917.0 822.7
Operating companies | International    
Disclosure of geographical areas [line items]    
Net earned premium 1,977.0 1,556.8
Insurance and Reinsurance | Operating companies | Northbridge    
Disclosure of geographical areas [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 (losses) on investments (55.6) 44.8
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Insurance and Reinsurance | Operating companies | Odyssey Group    
Disclosure of geographical areas [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 (losses) on investments (111.4) 253.1
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Insurance and Reinsurance | Operating companies | Crum & Forster    
Disclosure of geographical areas [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 (losses) on investments (144.2) 27.9
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Insurance and Reinsurance | Operating companies | Zenith National    
Disclosure of geographical areas [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 (losses) on investments (57.6) 26.6
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Insurance and Reinsurance | Operating companies | Brit    
Disclosure of geographical areas [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 (losses) on investments (63.1) 79.0
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Insurance and Reinsurance | Operating companies | Allied World    
Disclosure of geographical areas [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 (losses) on investments (66.9) (26.5)
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Insurance and Reinsurance | Operating companies | Fairfax Asia    
Disclosure of geographical areas [line items]    
Net earned premium 189.5 327.6
Insurance and Reinsurance | Operating companies | Other    
Disclosure of geographical areas [line items]    
Net earned premium 1,065.6 790.6
Insurance and Reinsurance | Operating companies | Canada | Northbridge    
Disclosure of geographical areas [line items]    
Net earned premium 1,108.2 1,007.2
Insurance and Reinsurance | Operating companies | Canada | Odyssey Group    
Disclosure of geographical areas [line items]    
Net earned premium 70.2 76.8
Insurance and Reinsurance | Operating companies | Canada | Crum & Forster    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Insurance and Reinsurance | Operating companies | Canada | Zenith National    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Insurance and Reinsurance | Operating companies | Canada | Brit    
Disclosure of geographical areas [line items]    
Net earned premium 95.3 83.1
Insurance and Reinsurance | Operating companies | Canada | Allied World    
Disclosure of geographical areas [line items]    
Net earned premium 28.2 20.5
Insurance and Reinsurance | Operating companies | Canada | Fairfax Asia    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.1
Insurance and Reinsurance | Operating companies | Canada | Other    
Disclosure of geographical areas [line items]    
Net earned premium 5.0 9.1
Insurance and Reinsurance | Operating companies | United States | Northbridge    
Disclosure of geographical areas [line items]    
Net earned premium 11.0 12.5
Insurance and Reinsurance | Operating companies | United States | Odyssey Group    
Disclosure of geographical areas [line items]    
Net earned premium 1,858.0 1,539.2
Insurance and Reinsurance | Operating companies | United States | Crum & Forster    
Disclosure of geographical areas [line items]    
Net earned premium 1,958.0 1,852.6
Insurance and Reinsurance | Operating companies | United States | Zenith National    
Disclosure of geographical areas [line items]    
Net earned premium 804.3 811.6
Insurance and Reinsurance | Operating companies | United States | Brit    
Disclosure of geographical areas [line items]    
Net earned premium 1,073.7 1,036.5
Insurance and Reinsurance | Operating companies | United States | Allied World    
Disclosure of geographical areas [line items]    
Net earned premium 1,671.9 773.7
Insurance and Reinsurance | Operating companies | United States | Fairfax Asia    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Insurance and Reinsurance | Operating companies | United States | Other    
Disclosure of geographical areas [line items]    
Net earned premium 83.6 98.9
Insurance and Reinsurance | Operating companies | Asia | Northbridge    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Insurance and Reinsurance | Operating companies | Asia | Odyssey Group    
Disclosure of geographical areas [line items]    
Net earned premium 319.8 247.2
Insurance and Reinsurance | Operating companies | Asia | Crum & Forster    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Insurance and Reinsurance | Operating companies | Asia | Zenith National    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Insurance and Reinsurance | Operating companies | Asia | Brit    
Disclosure of geographical areas [line items]    
Net earned premium 57.9 60.3
Insurance and Reinsurance | Operating companies | Asia | Allied World    
Disclosure of geographical areas [line items]    
Net earned premium 254.9 88.2
Insurance and Reinsurance | Operating companies | Asia | Fairfax Asia    
Disclosure of geographical areas [line items]    
Net earned premium 189.5 319.0
Insurance and Reinsurance | Operating companies | Asia | Other    
Disclosure of geographical areas [line items]    
Net earned premium 94.9 108.0
Insurance and Reinsurance | Operating companies | International | Northbridge    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Insurance and Reinsurance | Operating companies | International | Odyssey Group    
Disclosure of geographical areas [line items]    
Net earned premium 507.4 470.2
Insurance and Reinsurance | Operating companies | International | Crum & Forster    
Disclosure of geographical areas [line items]    
Net earned premium 2.9 0.2
Insurance and Reinsurance | Operating companies | International | Zenith National    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Insurance and Reinsurance | Operating companies | International | Brit    
Disclosure of geographical areas [line items]    
Net earned premium 252.8 357.0
Insurance and Reinsurance | Operating companies | International | Allied World    
Disclosure of geographical areas [line items]    
Net earned premium 331.8 146.3
Insurance and Reinsurance | Operating companies | International | Fairfax Asia    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 8.5
Insurance and Reinsurance | Operating companies | International | Other    
Disclosure of geographical areas [line items]    
Net earned premium 882.1 574.6
Runoff | Reportable segments    
Disclosure of geographical areas [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 (losses) on investments (107.6) 73.3
Gain on sale of subsidiary   0.0
Other revenue 0.0 0.0
Runoff | Reportable segments | Canada    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Runoff | Reportable segments | United States    
Disclosure of geographical areas [line items]    
Net earned premium 6.3 23.7
Runoff | Reportable segments | Asia    
Disclosure of geographical areas [line items]    
Net earned premium 0.0 0.0
Runoff | Reportable segments | International    
Disclosure of geographical areas [line items]    
Net earned premium $ 398.3 $ (3.6)
Geographic | Net Premiums Earned | Canada    
Disclosure of geographical areas [line items]    
Allocation of net premiums earned 10.80% 12.30%
Geographic | Net Premiums Earned | United States    
Disclosure of geographical areas [line items]    
Allocation of net premiums earned 61.90% 63.20%
Geographic | Net Premiums Earned | Asia    
Disclosure of geographical areas [line items]    
Allocation of net premiums earned 7.60% 8.50%
Geographic | Net Premiums Earned | International    
Disclosure of geographical areas [line items]    
Allocation of net premiums earned 19.70% 16.00%