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Rollforward of Fair Value Measurements by Level (Details) - USD ($)
$ in Millions
6 Months Ended
Jun. 30, 2017
Jun. 30, 2016
Dec. 31, 2016
Dec. 31, 2015
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance $ 2,547.3 $ 1,543.5    
Net realized and unrealized gains (losses) (83.0) 16.3    
Amortization/Accretion (4.7) (2.0)    
Purchases 1,516.4 3,066.7    
Sales 1,503.0 2,019.9    
Transfers in 11.1 0.0    
Transfers out (11.1) 0.0    
Ending balance 2,633.8 2,604.6    
Short-term investments, at amortized cost (which approximates fair value) 71.6   $ 174.9  
Level 1 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 279.5 789.0    
Net realized and unrealized gains (losses) 30.4 3.6    
Amortization/Accretion 0.0 0.1    
Purchases 665.0 1,312.9    
Sales 243.9 1,809.9    
Transfers in 0.0 0.0    
Transfers out 0.0 0.0    
Ending balance 731.0 295.7    
Level 2 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 2,093.8 585.6    
Net realized and unrealized gains (losses) 39.0 13.7    
Amortization/Accretion (4.7) (2.1)    
Purchases 770.7 1,668.7    
Sales 1,255.0 207.0    
Transfers in 11.1 0.0    
Transfers out 0.0 0.0    
Ending balance 1,649.7 2,058.9    
Fixed maturity investments | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 0.0 0.0    
Net realized and unrealized gains (losses) 0.1 0.1    
Amortization/Accretion 0.0 0.0    
Purchases 25.6 67.9    
Sales 0.5      
Transfers in 0.0 0.0    
Transfers out 11.1 0.0    
Ending balance 14.1 68.0    
Other long-term investments | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 91.4 103.6    
Net realized and unrealized gains (losses) (1.5) 1.6    
Amortization/Accretion 0.0 0.0    
Purchases 2.6 2.0    
Sales 2.0      
Transfers in 0.0 0.0    
Transfers out 0.0 0.0    
Ending balance 90.5 107.2    
Hedge and private equity funds included in other long-term investments | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 82.6 65.3    
Net realized and unrealized gains (losses) 15.0 (2.7)    
Amortization/Accretion 0.0 0.0    
Purchases 52.5 15.2    
Sales 1.6 3.0    
Transfers in 0.0 0.0    
Transfers out 0.0 0.0    
Ending balance 148.5 74.8    
Fair value measured on a recurring basis        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 2,639.7      
Ending balance 2,556.9      
Fair value measured on a recurring basis | Level 1 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 441.7      
Ending balance 786.7      
Fair value measured on a recurring basis | Level 2 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 2,106.6      
Ending balance 1,665.6      
Fair value measured on a recurring basis | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 91.4      
Ending balance 104.6      
Fair value measured on a recurring basis | Fixed maturity investments        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 2,087.7      
Ending balance 1,566.9      
Fair value measured on a recurring basis | Fixed maturity investments | Level 1 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 101.5      
Ending balance 49.7      
Fair value measured on a recurring basis | Fixed maturity investments | Level 2 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 1,986.2      
Ending balance 1,503.1      
Fair value measured on a recurring basis | Fixed maturity investments | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 0.0      
Ending balance 14.1      
Fair value measured on a recurring basis | Other long-term investments        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 91.4      
Ending balance 90.5      
Fair value measured on a recurring basis | Other long-term investments | Level 1 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 0.0      
Ending balance 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]        
Beginning balance 0.0      
Ending balance 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]        
Beginning balance 91.4      
Ending balance 90.5      
Fair value measured on a recurring basis | Short-term investments        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 175.0      
Ending balance 71.6      
Fair value measured on a recurring basis | Short-term investments | Level 1 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 162.3      
Ending balance 55.7      
Short-term investments, at amortized cost (which approximates fair value)   307.3 175.0 $ 142.0
Fair value measured on a recurring basis | Short-term investments | Level 2 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 12.7      
Ending balance 15.9      
Fair value measured on a recurring basis | Short-term investments | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 0.0      
Ending balance 0.0      
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)   0.3 0.1 0.1
Star & Shield Insurance Exchange        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Trading securities debt reclassified to assets held-for-sale   $ 9.2 6.6 $ 9.5
Forward Contracts | Fair value measured on a recurring basis | Other long-term investments | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Derivative, fair value, net (12.5)   $ (1.2)  
Star & Shield Insurance Exchange        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Sales 5.2      
Star & Shield Insurance Exchange | Level 1 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Sales 0.0      
Star & Shield Insurance Exchange | Level 2 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Sales 5.2      
Star & Shield Insurance Exchange | Fixed maturity investments        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance 6.6      
Star & Shield Insurance Exchange | Fixed maturity investments | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Sales 0.0      
Star & Shield Insurance Exchange | Other long-term investments | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Sales 0.0      
Star & Shield Insurance Exchange | Hedge and private equity funds included in other long-term investments | Level 3 Inputs        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Sales 0.0      
Star & Shield Insurance Exchange | Short-term investments        
Schedule of Trading Securities and Other Trading Assets [Line Items]        
Beginning balance $ 0.1