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Rollforward of Fair Value Measurements by Level (Details) - USD ($)
$ in Thousands
3 Months Ended 6 Months Ended
Jun. 30, 2016
Jun. 30, 2015
Jun. 30, 2016
Jun. 30, 2015
Dec. 31, 2015
Dec. 31, 2014
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     $ 4,050,900 $ 3,343,600    
Total realized and unrealized gains (losses)     57,600 11,100    
Amortization/Accretion     (8,000) (9,900)    
Purchases     3,622,500 1,293,700    
Sales     (2,631,200) (1,258,900)    
Transfers in     0 34,900    
Transfers out     0 (34,900)    
Balance at June 30, 2016 $ 5,091,800 $ 3,379,600 5,091,800 3,379,600    
Other Investments 329,200   329,200   $ 315,800  
Net realized and unrealized investment gains (losses), after tax 18,200 (10,500) 39,200 7,400    
Net realized and unrealized investment gains (losses) 28,100 (15,000) 57,600 10,000    
Short-term investments, at amortized cost (which approximates fair value) 421,800   $ 421,800   211,200  
Maximum Percentage Differences Between Prices Provided by Pricing Services Considered Outliers     (5.00%)      
Maximum price difference provided by pricing services     $ 1,000      
Level 1 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     1,152,200 550,600    
Total realized and unrealized gains (losses)     7,100 9,000    
Amortization/Accretion     100 0    
Purchases     1,449,700 495,400    
Sales     (2,043,900) (604,200)    
Transfers in     0 0    
Transfers out     0 0    
Balance at June 30, 2016 565,200 450,800 565,200 450,800    
Level 2 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     2,531,400 2,372,900    
Total realized and unrealized gains (losses)     38,300 5,900    
Amortization/Accretion     (8,100) (9,900)    
Purchases     2,076,900 734,300    
Sales     (577,400) (616,000)    
Transfers in     0 34,900    
Transfers out     0 0    
Balance at June 30, 2016 4,061,100 2,522,100 4,061,100 2,522,100    
Fixed maturity investments. | Level 3 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     70,000 76,400    
Total realized and unrealized gains (losses)     1,300 0    
Amortization/Accretion     0 0    
Purchases     84,700 35,300    
Sales     (2,800)      
Transfers in     0 0    
Transfers out     0 (34,900)    
Balance at June 30, 2016 153,200 76,800 153,200 76,800    
Common equity securities | Level 3 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     0 39,500    
Total realized and unrealized gains (losses)     0 6,600    
Amortization/Accretion     0 0    
Purchases     0 0    
Sales     0 (13,100)    
Transfers in     0 0    
Transfers out     0 0    
Balance at June 30, 2016 0 33,000 0 33,000    
Other long-term investments | Level 3 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     169,500 126,900    
Total realized and unrealized gains (losses)     12,900 (6,800)    
Amortization/Accretion     0 0    
Purchases     2,100 22,500    
Sales     0 (2,300)    
Transfers in     0 0    
Transfers out     0 0    
Balance at June 30, 2016 184,500 140,300 184,500 140,300    
Hedge and private equity funds included in other long-term investments | Level 3 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     127,800 177,300    
Total realized and unrealized gains (losses)     (2,000) (3,600)    
Amortization/Accretion     0 0    
Purchases     9,100 6,200    
Sales     (7,100) (23,300)    
Transfers in     0 0    
Transfers out     0 0    
Balance at June 30, 2016 127,800 156,600 127,800 156,600    
Fair value measured on a recurring basis            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     4,134,400      
Balance at June 30, 2016 5,386,100   5,386,100      
Fair value measured on a recurring basis | Level 1 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     1,363,500      
Balance at June 30, 2016 987,300   987,300      
Fair value measured on a recurring basis | Level 2 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     2,531,400      
Balance at June 30, 2016 4,061,100   4,061,100      
Fair value measured on a recurring basis | Level 3 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     239,500      
Balance at June 30, 2016 337,700   337,700      
Fair value measured on a recurring basis | Fixed maturity investments.            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     2,639,700      
Balance at June 30, 2016 4,372,000   4,372,000      
Fair value measured on a recurring basis | Fixed maturity investments. | Level 1 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     134,000      
Balance at June 30, 2016 252,900   252,900      
Fair value measured on a recurring basis | Fixed maturity investments. | Level 2 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     2,435,700      
Balance at June 30, 2016 3,965,900   3,965,900      
Fair value measured on a recurring basis | Fixed maturity investments. | Level 3 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     70,000      
Balance at June 30, 2016 153,200   153,200      
Fair value measured on a recurring basis | Other long-term investments            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     169,500      
Balance at June 30, 2016 184,500   184,500      
Fair value measured on a recurring basis | Other long-term investments | Level 1 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     0      
Balance at June 30, 2016 0   0      
Fair value measured on a recurring basis | Other long-term investments | Level 2 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     0      
Balance at June 30, 2016 0   0      
Fair value measured on a recurring basis | Other long-term investments | Level 3 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     169,500      
Balance at June 30, 2016 184,500   184,500      
Carrying value of investment accounted for using the equity method 3,500 3,900 3,500 3,900 3,800 $ 5,200
Fair value measured on a recurring basis | Short-term investments            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     211,300      
Balance at June 30, 2016 422,100   422,100      
Fair value measured on a recurring basis | Short-term investments | Level 1 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     211,300      
Balance at June 30, 2016 422,100   422,100      
Short-term investments, at amortized cost (which approximates fair value)   401,300   401,300 211,300 376,800
Fair value measured on a recurring basis | Short-term investments | Level 2 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     0      
Balance at June 30, 2016 0   0      
Fair value measured on a recurring basis | Short-term investments | Level 3 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Balance at January 1, 2016     0      
Balance at June 30, 2016 0   0      
Discontinued Operations [Member]            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Net realized and unrealized investment gains (losses) 7,300 (46,100) (1,500) 32,300    
Star & Shield Insurance Exchange | Fair value measured on a recurring basis | Short-term investments | Level 1 Inputs            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Short-term investments, at amortized cost (which approximates fair value) 300 1,100 300 1,100 100 1,900
Prospector Offshore Fund Ltd [Member] | Fair value measured on a recurring basis | Investment related liabilities [Member]            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Net realized and unrealized investment gains (losses)       900    
Affordable Housing Development Fund [Member]            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Other Investments 13,400 15,800 13,400 15,800 14,700 16,800
Affordable Housing Development Fund [Member] | Fair value measured on a recurring basis | Other long-term investments            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Other Investments 13,400   13,400   14,700  
Star & Shield Insurance Exchange            
Schedule of Trading Securities and Other Trading Assets [Line Items]            
Trading Securities Debt Reclassified to Assets Held-for-sale $ 9,200 $ 9,100 $ 9,200 $ 9,100 $ 9,500 $ 10,100