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Investment Securities (Rollforward of Fair Value Measurements by Level) (Details)
3 Months Ended 9 Months Ended
Sep. 30, 2018
USD ($)
Sep. 30, 2017
USD ($)
Sep. 30, 2018
USD ($)
Sep. 30, 2017
USD ($)
Dec. 31, 2017
USD ($)
Dec. 31, 2016
USD ($)
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     $ 3,208,300,000 $ 2,547,300,000    
Net realized and unrealized gains (losses)     31,300,000 125,600,000    
Amortization/Accretion     (2,200,000) (6,600,000)    
Purchases     1,151,900,000 2,078,200,000    
Sales     (2,024,200,000) (2,229,900,000)    
Transfers in     0 13,100,000    
Transfers out     0 (13,100,000)    
Ending balance $ 2,365,100,000 $ 2,509,400,000 2,365,100,000 2,509,400,000    
Net realized and unrealized investment (losses) gains 66,100,000 32,500,000 22,900,000 102,500,000    
Level 1 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     890,400,000 279,500,000    
Net realized and unrealized gains (losses)     51,900,000 52,400,000    
Amortization/Accretion     100,000 0    
Purchases     412,600,000 940,700,000    
Sales     (457,600,000) (539,000,000)    
Transfers in     0 0    
Transfers out     0 0    
Ending balance 897,400,000 733,600,000 897,400,000 733,600,000    
Level 2 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     2,105,400,000 2,093,800,000    
Net realized and unrealized gains (losses)     (33,600,000) 59,800,000    
Amortization/Accretion     (2,300,000) (6,600,000)    
Purchases     673,500,000 1,038,500,000    
Sales     (1,565,000,000) (1,668,200,000)    
Transfers in     0 13,100,000    
Transfers out     0 0    
Ending balance $ 1,178,000,000 1,525,200,000 $ 1,178,000,000 1,525,200,000    
Number of Investments 2   2      
Fixed maturity investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     $ 0 0    
Net realized and unrealized gains (losses)     0 0    
Amortization/Accretion     0 0    
Purchases     0 31,200,000    
Sales     0 (12,500,000)    
Transfers in     0 0    
Transfers out     0 (13,100,000)    
Ending balance $ 0 5,600,000 0 5,600,000    
Other long-term investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     87,200,000 91,400,000    
Net realized and unrealized gains (losses)     (4,200,000) (2,200,000)    
Amortization/Accretion     0 0    
Purchases     55,100,000 2,900,000    
Sales     0 (2,000,000)    
Transfers in     0 0    
Transfers out     0 0    
Ending balance 138,100,000 90,100,000 138,100,000 90,100,000    
Hedge and private equity funds included in other long-term investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     125,300,000 82,600,000    
Net realized and unrealized gains (losses)     17,200,000 15,600,000    
Amortization/Accretion     0 0    
Purchases     10,700,000 64,900,000    
Sales     (1,600,000) (8,200,000)    
Transfers in     0 0    
Transfers out     0 0    
Ending balance 151,600,000 154,900,000 151,600,000 154,900,000    
Short-term investments            
Debt and Equity Securities, FV-NI [Line Items]            
Net realized and unrealized investment (losses) gains     (700,000.0)      
Foreign Exchange Forward            
Debt and Equity Securities, FV-NI [Line Items]            
Net realized and unrealized investment (losses) gains     (3,500,000.0) (23,100,000.0)    
Foreign Currency on Cash and Open Trades            
Debt and Equity Securities, FV-NI [Line Items]            
Net realized and unrealized investment (losses) gains     (4,200,000.0)      
Fair value measured on a recurring basis            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     3,259,100,000      
Ending balance 2,527,200,000   2,527,200,000      
Fair value measured on a recurring basis | Level 1 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     1,041,400,000      
Ending balance 1,198,100,000   1,198,100,000      
Fair value measured on a recurring basis | Level 2 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     2,130,500,000      
Ending balance 1,191,000,000   1,191,000,000      
Fair value measured on a recurring basis | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     87,200,000      
Ending balance 138,100,000   138,100,000      
Fair value measured on a recurring basis | Fixed maturity investments            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     2,129,700,000      
Ending balance 1,031,900,000   1,031,900,000      
Fair value measured on a recurring basis | Fixed maturity investments | Level 1 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     296,500,000      
Ending balance 125,400,000   125,400,000      
Fair value measured on a recurring basis | Fixed maturity investments | Level 2 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     1,833,200,000      
Ending balance 906,500,000   906,500,000      
Fair value measured on a recurring basis | Fixed maturity investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     0      
Ending balance 0   0      
Fair value measured on a recurring basis | Other long-term investments            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     87,200,000      
Ending balance 138,100,000   138,100,000      
Fair value measured on a recurring basis | Other long-term investments | Level 1 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     0      
Ending balance 0   0      
Fair value measured on a recurring basis | Other long-term investments | Level 2 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     0      
Ending balance 0   0      
Fair value measured on a recurring basis | Other long-term investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     87,200,000      
Ending balance 138,100,000   138,100,000      
Fair value measured on a recurring basis | Short-term investments            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     176,100,000      
Short-term investments, at fair value 313,700,000   313,700,000      
Fair value measured on a recurring basis | Short-term investments | Level 1 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     151,000,000      
Ending balance 300,700,000   300,700,000      
Short-term investments, at fair value   786,500,000   786,500,000 $ 176,100,000 $ 175,000,000
Fair value measured on a recurring basis | Short-term investments | Level 2 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     25,100,000      
Ending balance 13,000,000   13,000,000      
Fair value measured on a recurring basis | Short-term investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Beginning balance     0      
Ending balance $ 0   $ 0      
Forward Contracts | Fair value measured on a recurring basis | Other long-term investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Derivative, fair value, net   $ (15,400,000)   (15,400,000) $ (3,700,000) (1,200,000)
Star & Shield Insurance Exchange            
Debt and Equity Securities, FV-NI [Line Items]            
Deconsolidation of SSIE       5,200,000    
Star & Shield Insurance Exchange | Level 1 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Deconsolidation of SSIE       0    
Star & Shield Insurance Exchange | Level 2 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Deconsolidation of SSIE       5,200,000    
Star & Shield Insurance Exchange | Fixed maturity investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Deconsolidation of SSIE       0    
Star & Shield Insurance Exchange | Other long-term investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Deconsolidation of SSIE       0    
Star & Shield Insurance Exchange | Hedge and private equity funds included in other long-term investments | Level 3 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Deconsolidation of SSIE       $ 0    
Star & Shield Insurance Exchange            
Debt and Equity Securities, FV-NI [Line Items]            
Trading securities debt reclassified to assets held-for-sale           6,600,000
Star & Shield Insurance Exchange | Fair value measured on a recurring basis | Short-term investments | Level 1 Inputs            
Debt and Equity Securities, FV-NI [Line Items]            
Short-term investments, at fair value           $ 100,000