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Summary of Significant Accounting Policies Losses, Claims and Settlement Expenses - Consolidated - Incurred and Paid Loss Development Tables (Details)
$ in Millions
Dec. 31, 2019
USD ($)
claim
Dec. 31, 2018
USD ($)
Dec. 31, 2017
USD ($)
Dec. 31, 2016
USD ($)
Dec. 31, 2015
USD ($)
Dec. 31, 2014
USD ($)
Dec. 31, 2013
USD ($)
Dec. 31, 2012
USD ($)
Dec. 31, 2011
USD ($)
Dec. 31, 2010
USD ($)
Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) $ 6,856.8                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance 4,196.1                  
Sub-total 2,660.7                  
All outstanding liabilities before 2010, net of reinsurance 628.0                  
Liabilities for claims and allocated claim adjustment expenses, net of reinsurance 3,288.8                  
General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 1,071.5                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance 599.3                  
Sub-total 472.1                  
All outstanding liabilities before 2010, net of reinsurance 138.7                  
Liabilities for claims and allocated claim adjustment expenses, net of reinsurance 610.9                  
Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 7,123.2                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance 5,723.7                  
Sub-total 1,399.5                  
All outstanding liabilities before 2010, net of reinsurance 3.5                  
Liabilities for claims and allocated claim adjustment expenses, net of reinsurance 1,403.0                  
Accident Year 2010 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 565.7 $ 563.2 $ 563.5 $ 564.0 $ 563.1 $ 569.1 $ 545.3 $ 521.5 $ 480.0 $ 485.1
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 21.4                  
Cumulative Number of Reported Claims | claim 57,763                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 514.0 507.2 496.1 482.8 466.5 464.0 427.9 370.1 279.8 118.9
Accident Year 2010 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 67.9 67.9 68.6 68.6 69.7 70.4 64.7 66.6 67.8 68.4
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 4.2                  
Cumulative Number of Reported Claims | claim 5,386                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 61.3 59.6 56.4 55.5 52.1 44.3 31.1 20.8 10.8 3.9
Accident Year 2010 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 468.6 473.5 473.7 479.9 494.9 532.4 530.9 530.3 546.9 584.3
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 0.1                  
Cumulative Number of Reported Claims | claim 92,191                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 468.4 467.6 466.6 465.7 460.0 449.4 423.8 372.7 305.8 $ 200.0
Accident Year 2011 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 626.9 634.9 649.3 641.7 643.0 622.5 595.3 567.3 558.6  
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 42.8                  
Cumulative Number of Reported Claims | claim 53,329                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 550.0 539.7 526.4 503.4 469.8 424.0 361.4 266.7 112.6  
Accident Year 2011 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 91.1 94.4 94.6 96.0 95.8 80.0 72.9 71.5 72.5  
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 7.2                  
Cumulative Number of Reported Claims | claim 4,739                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 79.7 80.7 75.3 68.9 58.7 43.6 26.0 12.1 2.5  
Accident Year 2011 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 534.3 537.2 539.3 549.0 549.9 582.3 584.4 599.9 591.6  
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 2.2                  
Cumulative Number of Reported Claims | claim 96,789                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 528.8 526.6 525.0 523.0 511.6 483.2 436.2 352.7 $ 223.1  
Accident Year 2012 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 654.7 660.5 671.1 676.4 678.1 670.6 647.2 629.3    
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 34.0                  
Cumulative Number of Reported Claims | claim 49,910                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 531.5 518.4 496.6 469.5 426.7 361.8 265.8 113.1    
Accident Year 2012 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 105.6 108.2 109.6 107.3 100.9 89.2 91.2 95.0    
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 8.4                  
Cumulative Number of Reported Claims | claim 5,277                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 90.8 86.4 75.8 67.4 50.8 36.0 18.8 5.5    
Accident Year 2012 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 552.1 558.0 558.6 573.1 575.0 603.9 619.6 622.5    
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 3.2                  
Cumulative Number of Reported Claims | claim 98,042                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 545.3 543.9 539.1 525.9 498.6 442.9 351.4 $ 229.0    
Accident Year 2013 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 689.7 717.2 726.3 722.7 716.9 705.3 700.9      
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 80.0                  
Cumulative Number of Reported Claims | claim 49,005                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 547.0 526.8 501.9 449.8 381.2 274.3 107.6      
Accident Year 2013 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 101.4 106.0 106.7 107.8 96.5 96.7 95.7      
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 9.8                  
Cumulative Number of Reported Claims | claim 5,520                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 86.9 85.1 76.1 58.5 34.4 13.6 4.0      
Accident Year 2013 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 634.4 647.3 659.7 669.6 668.5 665.4 661.5      
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 3.1                  
Cumulative Number of Reported Claims | claim 96,992                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 627.3 623.9 611.5 578.1 511.0 398.1 $ 248.3      
Accident Year 2014 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 763.3 777.0 784.9 786.4 792.8 780.9        
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 156.0                  
Cumulative Number of Reported Claims | claim 54,127                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 524.8 499.5 466.0 397.1 293.7 116.9        
Accident Year 2014 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 117.1 117.0 111.0 109.4 110.4 107.0        
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 16.6                  
Cumulative Number of Reported Claims | claim 5,998                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 82.8 73.5 52.8 32.0 15.8 5.8        
Accident Year 2014 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 688.1 689.1 688.0 691.7 689.2 687.8        
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 11.4                  
Cumulative Number of Reported Claims | claim 103,223                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 665.1 640.8 605.4 536.9 430.5 $ 267.4        
Accident Year 2015 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 769.1 785.5 787.3 792.6 794.3          
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 220.5                  
Cumulative Number of Reported Claims | claim 55,149                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 466.7 435.1 379.3 274.9 109.0          
Accident Year 2015 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 104.8 102.3 99.2 96.3 96.0          
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 24.3                  
Cumulative Number of Reported Claims | claim 5,540                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 64.5 47.4 29.5 16.0 6.3          
Accident Year 2015 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 721.5 722.0 729.7 710.5 712.4          
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 24.4                  
Cumulative Number of Reported Claims | claim 104,776                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 670.5 626.8 541.8 438.9 $ 265.1          
Accident Year 2016 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 730.5 745.7 752.9 756.1            
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 256.3                  
Cumulative Number of Reported Claims | claim 52,316                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 383.5 334.4 253.5 102.5            
Accident Year 2016 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 100.3 98.8 96.7 92.4            
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 32.8                  
Cumulative Number of Reported Claims | claim 83,172                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 47.7 34.8 18.5 7.1            
Accident Year 2016 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 776.7 784.5 768.9 755.9            
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 25.9                  
Cumulative Number of Reported Claims | claim 110,045                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 673.7 583.6 469.6 $ 290.2            
Accident Year 2017 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 700.3 713.9 727.0              
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 229.6                  
Cumulative Number of Reported Claims | claim 51,525                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 334.8 244.6 99.6              
Accident Year 2017 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 129.6 121.4 111.2              
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 29.3                  
Cumulative Number of Reported Claims | claim 460,224                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 50.1 25.9 5.7              
Accident Year 2017 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 868.1 818.8 788.7              
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 36.9                  
Cumulative Number of Reported Claims | claim 116,144                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 656.1 511.7 $ 307.9              
Accident Year 2018 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 691.5 698.6                
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 274.9                  
Cumulative Number of Reported Claims | claim 51,695                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 240.6 94.8                
Accident Year 2018 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 119.7 120.5                
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 39.8                  
Cumulative Number of Reported Claims | claim 461,270                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 28.8 6.9                
Accident Year 2018 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 948.2 883.3                
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 20.2                  
Cumulative Number of Reported Claims | claim 126,859                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 557.7 $ 330.1                
Accident Year 2019 [Member] | Workers' Compensation [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 664.6                  
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 380.6                  
Cumulative Number of Reported Claims | claim 40,042                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 102.9                  
Accident Year 2019 [Member] | General Liability [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 133.5                  
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 86.5                  
Cumulative Number of Reported Claims | claim 356,996                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 6.4                  
Accident Year 2019 [Member] | Commercial Automobile [Member]                    
Claims Development [Line Items]                    
Incurred Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance (Undiscounted) 930.9                  
Total of Incurred-but-Not-Reported Liabilities Plus Expected Development on Reported Claims $ 74.9                  
Cumulative Number of Reported Claims | claim 117,696                  
Cumulative Paid Claims and Allocated Claim Adjustment Expenses, Net of Reinsurance $ 330.2