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Fair Value Measurements - Financial Assets Measured on Recurring Basis (Details) - USD ($)
$ in Millions
Dec. 31, 2017
Dec. 31, 2016
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Catastrophe bonds trading, at fair value $ 33.5 $ 42.5
Derivatives at fair value 6.4 7.2
Recurring    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Loan notes issued by variable interest entities, at fair value (44.2) (115.0)
Loan notes issued by variable interest entities, at fair value (included within accrued expenses and other payables) (42.4) (108.4)
Total 7,485.4 7,653.6
Recurring | Equity investments trading    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 491.0 584.7
Recurring | Derivatives at fair value | Foreign Exchange Contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Derivatives at fair value 6.4 7.2
Recurring | Liabilities under derivative contracts | Foreign Exchange Contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value (1.0) (18.4)
Recurring | Total fixed income securities — Available for sale | U.S. government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,159.4 1,206.1
Recurring | Total fixed income securities — Available for sale | U.S. agency    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 52.1 119.6
Recurring | Total fixed income securities — Available for sale | Municipal    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 54.9 24.4
Recurring | Total fixed income securities — Available for sale | Corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 2,415.7 2,586.5
Recurring | Total fixed income securities — Available for sale | Non-U.S. government-backed corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 91.3 89.8
Recurring | Total fixed income securities — Available for sale | Non-U.S government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 484.9 488.7
Recurring | Total fixed income securities — Available for sale | Asset-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 26.2 63.0
Recurring | Total fixed income securities — Available for sale | Non-agency commercial mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value   12.6
Recurring | Total fixed income securities — Available for sale | Agency mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 946.5 1,073.9
Recurring | Fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 5,231.0 5,664.6
Recurring | Short-term Investments    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 89.9 145.3
Recurring | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,649.3 1,265.7
Catastrophe bonds trading, at fair value 32.4 42.5
Recurring | Held for trading financial assets, at fair value | U.S. government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 161.9 82.4
Recurring | Held for trading financial assets, at fair value | Municipal    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 32.2 15.5
Recurring | Held for trading financial assets, at fair value | Corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,046.3 820.6
Recurring | Held for trading financial assets, at fair value | Non-U.S. government-backed corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1.0  
Recurring | Held for trading financial assets, at fair value | Non-U.S government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 202.5 202.8
Recurring | Held for trading financial assets, at fair value | Asset-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 9.9 14.5
Recurring | Held for trading financial assets, at fair value | Agency mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 195.5 129.9
Recurring | Level 1    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Loan notes issued by variable interest entities, at fair value 0.0 0.0
Loan notes issued by variable interest entities, at fair value (included within accrued expenses and other payables) 0.0 0.0
Total 2,338.3 2,411.6
Recurring | Level 1 | Equity investments trading    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 491.0 584.7
Recurring | Level 1 | Derivatives at fair value | Foreign Exchange Contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Derivatives at fair value 0.0 0.0
Recurring | Level 1 | Liabilities under derivative contracts | Foreign Exchange Contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value 0.0 0.0
Recurring | Level 1 | Total fixed income securities — Available for sale | U.S. government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,159.4 1,206.1
Recurring | Level 1 | Total fixed income securities — Available for sale | U.S. agency    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 1 | Total fixed income securities — Available for sale | Municipal    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 1 | Total fixed income securities — Available for sale | Corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 1 | Total fixed income securities — Available for sale | Non-U.S. government-backed corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 1 | Total fixed income securities — Available for sale | Non-U.S government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 341.2 343.7
Recurring | Level 1 | Total fixed income securities — Available for sale | Asset-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 1 | Total fixed income securities — Available for sale | Non-agency commercial mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value   0.0
Recurring | Level 1 | Total fixed income securities — Available for sale | Agency mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 1 | Fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,500.6 1,549.8
Recurring | Level 1 | Short-term Investments    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 87.3 118.6
Recurring | Level 1 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 186.4 82.4
Catastrophe bonds trading, at fair value 0.0 0.0
Recurring | Level 1 | Held for trading financial assets, at fair value | U.S. government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 161.9 82.4
Recurring | Level 1 | Held for trading financial assets, at fair value | Municipal    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 1 | Held for trading financial assets, at fair value | Corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 1 | Held for trading financial assets, at fair value | Non-U.S. government-backed corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0  
Recurring | Level 1 | Held for trading financial assets, at fair value | Non-U.S government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 24.5 0.0
Recurring | Level 1 | Held for trading financial assets, at fair value | Asset-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 1 | Held for trading financial assets, at fair value | Agency mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 2    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Loan notes issued by variable interest entities, at fair value 0.0 0.0
Loan notes issued by variable interest entities, at fair value (included within accrued expenses and other payables) 0.0 0.0
Total 5,233.7 5,465.4
Recurring | Level 2 | Equity investments trading    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 2 | Derivatives at fair value | Foreign Exchange Contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Derivatives at fair value 6.4 7.2
Recurring | Level 2 | Liabilities under derivative contracts | Foreign Exchange Contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value (1.0) (18.4)
Recurring | Level 2 | Total fixed income securities — Available for sale | U.S. government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 2 | Total fixed income securities — Available for sale | U.S. agency    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 52.1 119.6
Recurring | Level 2 | Total fixed income securities — Available for sale | Municipal    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 54.9 24.4
Recurring | Level 2 | Total fixed income securities — Available for sale | Corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 2,415.7 2,586.5
Recurring | Level 2 | Total fixed income securities — Available for sale | Non-U.S. government-backed corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 91.3 89.8
Recurring | Level 2 | Total fixed income securities — Available for sale | Non-U.S government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 143.7 145.0
Recurring | Level 2 | Total fixed income securities — Available for sale | Asset-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 26.2 63.0
Recurring | Level 2 | Total fixed income securities — Available for sale | Non-agency commercial mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value   12.6
Recurring | Level 2 | Total fixed income securities — Available for sale | Agency mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 946.5 1,073.9
Recurring | Level 2 | Fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 3,730.4 4,114.8
Recurring | Level 2 | Short-term Investments    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 2.6 26.7
Recurring | Level 2 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,462.9 1,183.3
Catastrophe bonds trading, at fair value 32.4 42.5
Recurring | Level 2 | Held for trading financial assets, at fair value | U.S. government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 2 | Held for trading financial assets, at fair value | Municipal    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 32.2 15.5
Recurring | Level 2 | Held for trading financial assets, at fair value | Corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1,046.3 820.6
Recurring | Level 2 | Held for trading financial assets, at fair value | Non-U.S. government-backed corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 1.0  
Recurring | Level 2 | Held for trading financial assets, at fair value | Non-U.S government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 178.0 202.8
Recurring | Level 2 | Held for trading financial assets, at fair value | Asset-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 9.9 14.5
Recurring | Level 2 | Held for trading financial assets, at fair value | Agency mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 195.5 129.9
Recurring | Level 3    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Loan notes issued by variable interest entities, at fair value (44.2) (115.0)
Loan notes issued by variable interest entities, at fair value (included within accrued expenses and other payables) (42.4) (108.4)
Total (86.6) (223.4)
Recurring | Level 3 | Equity investments trading    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Derivatives at fair value | Foreign Exchange Contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Derivatives at fair value 0.0 0.0
Recurring | Level 3 | Liabilities under derivative contracts | Foreign Exchange Contracts    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Liabilities under derivative contracts, fair value 0.0 0.0
Recurring | Level 3 | Total fixed income securities — Available for sale | U.S. government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Total fixed income securities — Available for sale | U.S. agency    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Total fixed income securities — Available for sale | Municipal    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Total fixed income securities — Available for sale | Corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Total fixed income securities — Available for sale | Non-U.S. government-backed corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Total fixed income securities — Available for sale | Non-U.S government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Total fixed income securities — Available for sale | Asset-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Total fixed income securities — Available for sale | Non-agency commercial mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value   0.0
Recurring | Level 3 | Total fixed income securities — Available for sale | Agency mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Fixed income securities — Available for sale    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Short-term Investments    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Held for trading financial assets, at fair value    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Catastrophe bonds trading, at fair value 0.0 0.0
Recurring | Level 3 | Held for trading financial assets, at fair value | U.S. government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Held for trading financial assets, at fair value | Municipal    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Held for trading financial assets, at fair value | Corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Held for trading financial assets, at fair value | Non-U.S. government-backed corporate    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0  
Recurring | Level 3 | Held for trading financial assets, at fair value | Non-U.S government    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Held for trading financial assets, at fair value | Asset-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Recurring | Level 3 | Held for trading financial assets, at fair value | Agency mortgage-backed    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 0.0
Fixed income securities — Trading | Recurring    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 73.0 185.4
Fixed income securities — Trading | Recurring | Level 1    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 73.0 76.1
Fixed income securities — Trading | Recurring | Level 2    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value 0.0 109.3
Fixed income securities — Trading | Recurring | Level 3    
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]    
Investments, fair value $ 0.0 $ 0.0