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Fair Value Measurements - Level 3 Inputs Reconciliation (Details) - USD ($)
$ in Millions
3 Months Ended
Mar. 31, 2020
Mar. 31, 2019
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]    
Balance at Beginning of Period $ 1,044.2 $ 897.4
Total Gains (Losses):    
Included in Condensed Consolidated Statement of Operations (3.0) (2.8)
Included in Other Comprehensive Income (Loss) (34.8) 11.9
Purchases 81.4 105.2
Settlements 0.0 (11.6)
Sales (44.8) (65.9)
Transfers into Level 3 0.0 16.5
Transfers out of Level 3 (557.7) 0.0
Balance at End of Period 485.3 950.7
Bonds and Notes    
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]    
Balance at Beginning of Period 409.1 382.6
Total Gains (Losses):    
Included in Condensed Consolidated Statement of Operations (2.7) (2.5)
Included in Other Comprehensive Income (Loss) (24.8) 5.4
Purchases 27.2 101.3
Settlements 0.0 (11.5)
Sales (18.2) (65.9)
Transfers into Level 3 0.0 2.5
Transfers out of Level 3 0.0 0.0
Balance at End of Period 390.6 411.9
States and Political Subdivisions    
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]    
Balance at Beginning of Period 0.0  
Total Gains (Losses):    
Included in Condensed Consolidated Statement of Operations 0.0  
Included in Other Comprehensive Income (Loss) 0.1  
Purchases 0.6  
Settlements 0.0  
Sales 0.0  
Transfers into Level 3 0.0  
Transfers out of Level 3 0.0  
Balance at End of Period 0.7  
Redeemable Preferred Stocks    
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]    
Balance at Beginning of Period 6.7  
Total Gains (Losses):    
Included in Condensed Consolidated Statement of Operations 0.0  
Included in Other Comprehensive Income (Loss) 0.0  
Purchases 0.0  
Settlements 0.0  
Sales 0.0  
Transfers into Level 3 0.0  
Transfers out of Level 3 0.0  
Collateralized Loan Obligations    
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]    
Balance at Beginning of Period 618.2 504.9
Total Gains (Losses):    
Included in Condensed Consolidated Statement of Operations (0.3) (0.3)
Included in Other Comprehensive Income (Loss) (9.5) 6.0
Purchases 53.6 3.9
Settlements 0.0 0.0
Sales (26.4) 0.0
Transfers into Level 3 0.0 14.0
Transfers out of Level 3 (557.7) 0.0
Balance at End of Period 77.9 528.5
Other Mortgage- and Asset-backed    
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation, Calculation [Roll Forward]    
Balance at Beginning of Period 10.2 9.9
Total Gains (Losses):    
Included in Condensed Consolidated Statement of Operations 0.0 0.0
Included in Other Comprehensive Income (Loss) (0.6) 0.5
Purchases 0.0 0.0
Settlements 0.0 (0.1)
Sales (0.2) 0.0
Transfers into Level 3 0.0 0.0
Transfers out of Level 3 0.0 0.0
Balance at End of Period $ 9.4 $ 10.3