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Property and Casualty Insurance Reserves - Short-duration Insurance Contracts, Claims Development (Details)
$ in Millions
Dec. 31, 2021
USD ($)
claim
Dec. 31, 2020
USD ($)
Dec. 31, 2019
USD ($)
Dec. 31, 2018
USD ($)
Dec. 31, 2017
USD ($)
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Loss and Allocated LAE Reserves, Net of Reinsurance $ 2,491.9        
Specialty Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 7,281.3        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net 5,581.5        
Outstanding Loss and Allocated LAE Reserves on Accident Years before 2015, Net of Reinsurance 22.5        
Loss and Allocated LAE Reserves, Net of Reinsurance 1,722.3        
Specialty Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 3,317.3        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net 3,255.3        
Outstanding Loss and Allocated LAE Reserves on Accident Years before 2015, Net of Reinsurance 1.6        
Loss and Allocated LAE Reserves, Net of Reinsurance 63.6        
Commercial Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 729.5        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net 443.2        
Outstanding Loss and Allocated LAE Reserves on Accident Years before 2015, Net of Reinsurance 14.1        
Loss and Allocated LAE Reserves, Net of Reinsurance 300.4        
Commercial Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 158.5        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net 149.0        
Outstanding Loss and Allocated LAE Reserves on Accident Years before 2015, Net of Reinsurance 0.4        
Loss and Allocated LAE Reserves, Net of Reinsurance 9.9        
Preferred Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 853.9        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net 601.9        
Outstanding Loss and Allocated LAE Reserves on Accident Years before 2015, Net of Reinsurance 10.2        
Loss and Allocated LAE Reserves, Net of Reinsurance 262.2        
Preferred Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 558.0        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net 552.6        
Outstanding Loss and Allocated LAE Reserves on Accident Years before 2015, Net of Reinsurance 0.0        
Loss and Allocated LAE Reserves, Net of Reinsurance 5.4        
Homeowners Insurance          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 892.0        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net 813.9        
Outstanding Loss and Allocated LAE Reserves on Accident Years before 2015, Net of Reinsurance 3.3        
Loss and Allocated LAE Reserves, Net of Reinsurance 81.4        
2015 | Specialty Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 1,197.4 $ 1,181.6 $ 1,185.6 $ 1,175.6 $ 1,170.2
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 15.1        
Cumulative Number of Reported Claims | claim 458,261        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 1,169.3 1,141.9 1,092.9 945.5 498.3
2015 | Specialty Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 522.4 522.5 522.0 522.5 533.1
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ (0.1)        
Cumulative Number of Reported Claims | claim 296,392        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 522.5 522.7 523.0 525.6 493.2
2015 | Commercial Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 114.4 114.3 118.3 120.0 120.5
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 2.3        
Cumulative Number of Reported Claims | claim 19,967        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 107.2 101.7 90.7 72.3 36.3
2015 | Commercial Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 23.4 23.4 23.5 23.5 24.2
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 0.0        
Cumulative Number of Reported Claims | claim 9,792        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 23.4 23.4 23.4 23.5 22.2
2015 | Preferred Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 160.0 158.2 155.8 157.8 164.4
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 0.6        
Cumulative Number of Reported Claims | claim 33,734        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 150.6 143.2 134.1 108.9 59.2
2015 | Preferred Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 105.2 105.1 105.2 105.8 109.2
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 0.0        
Cumulative Number of Reported Claims | claim 62,685        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 105.2 105.1 105.2 106.1 104.4
2015 | Homeowners Insurance          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 243.9 243.8 245.2 259.5 261.2
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 1.3        
Cumulative Number of Reported Claims | claim 19,619        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 241.7 239.5 235.7 242.5 $ 165.8
2016 | Specialty Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 1,314.5 1,307.8 1,310.5 1,324.0  
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 24.0        
Cumulative Number of Reported Claims | claim 508,623        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 1,265.5 1,211.8 1,050.8 541.3  
2016 | Specialty Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 547.8 548.0 548.6 558.9  
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ (0.6)        
Cumulative Number of Reported Claims | claim 309,577        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 548.3 549.0 553.1 509.4  
2016 | Commercial Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 110.9 113.0 116.5 123.2  
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 4.7        
Cumulative Number of Reported Claims | claim 20,195        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 98.1 88.1 68.8 36.8  
2016 | Commercial Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 23.6 23.6 23.5 23.6  
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 0.1        
Cumulative Number of Reported Claims | claim 9,569        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 23.6 23.6 23.6 21.7  
2016 | Preferred Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 163.4 161.7 156.3 157.6  
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 1.7        
Cumulative Number of Reported Claims | claim 31,922        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 147.4 132.7 107.6 55.5  
2016 | Preferred Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 110.4 110.4 111.0 113.9  
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 0.1        
Cumulative Number of Reported Claims | claim 61,921        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 110.3 110.4 111.4 107.2  
2016 | Homeowners Insurance          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 185.3 183.6 183.0 185.9  
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 4.1        
Cumulative Number of Reported Claims | claim 16,212        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 183.1 180.0 180.2 $ 127.4  
2017 | Specialty Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 1,506.1 1,494.7 1,461.5    
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 54.8        
Cumulative Number of Reported Claims | claim 546,521        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 1,382.0 1,200.7 567.3    
2017 | Specialty Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 629.6 630.3 624.3    
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ (10.5)        
Cumulative Number of Reported Claims | claim 324,321        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 630.6 634.8 570.8    
2017 | Commercial Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 126.6 126.1 128.4    
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 11.5        
Cumulative Number of Reported Claims | claim 19,572        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 99.5 75.7 32.4    
2017 | Commercial Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 26.9 27.1 26.0    
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ (0.5)        
Cumulative Number of Reported Claims | claim 9,305        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 26.8 26.9 23.0    
2017 | Preferred Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 200.0 195.5 172.2    
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 4.9        
Cumulative Number of Reported Claims | claim 34,633        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 160.8 127.9 62.7    
2017 | Preferred Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 125.9 125.8 126.4    
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 0.3        
Cumulative Number of Reported Claims | claim 67,181        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 125.6 126.5 120.7    
2017 | Homeowners Insurance          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 163.1 161.8 162.9    
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 2.5        
Cumulative Number of Reported Claims | claim 14,670        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 157.7 150.4 $ 111.1    
2018 | Specialty Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 1,406.4 1,401.2      
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 111.6        
Cumulative Number of Reported Claims | claim 474,346        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 1,107.6 555.2      
2018 | Specialty Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 659.5 650.5      
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ (6.4)        
Cumulative Number of Reported Claims | claim 296,167        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 663.8 585.5      
2018 | Commercial Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 152.0 140.5      
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 25.5        
Cumulative Number of Reported Claims | claim 19,354        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 87.6 37.0      
2018 | Commercial Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 32.2 31.9      
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 0.0        
Cumulative Number of Reported Claims | claim 11,011        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 31.9 26.2      
2018 | Preferred Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 153.6 148.9      
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 16.1        
Cumulative Number of Reported Claims | claim 24,438        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 92.8 44.4      
2018 | Preferred Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 98.0 96.1      
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ (0.5)        
Cumulative Number of Reported Claims | claim 47,603        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 98.4 90.9      
2018 | Homeowners Insurance          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 149.8 157.0      
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 4.3        
Cumulative Number of Reported Claims | claim 13,887        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 130.8 $ 94.6      
2019 | Specialty Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 1,856.9        
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 607.1        
Cumulative Number of Reported Claims | claim 544,207        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 657.1        
2019 | Specialty Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 958.0        
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 2.1        
Cumulative Number of Reported Claims | claim 348,244        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 890.1        
2019 | Commercial Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 225.6        
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 99.1        
Cumulative Number of Reported Claims | claim 24,690        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 50.8        
2019 | Commercial Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 52.4        
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 0.4        
Cumulative Number of Reported Claims | claim 16,494        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 43.3        
2019 | Preferred Personal Automobile Insurance—Liability          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 176.9        
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 54.1        
Cumulative Number of Reported Claims | claim 25,149        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 50.3        
2019 | Preferred Personal Automobile Insurance—Physical Damage          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 118.5        
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ (0.7)        
Cumulative Number of Reported Claims | claim 50,533        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 113.1        
2019 | Homeowners Insurance          
Claims Development [Line Items]          
Incurred Losses and Allocated LAE, Net of Reinsurance For the Years Ended December 31, 149.9        
Total of IBNR Liabilities Plus Expected Development on Reported Claims $ 19.1        
Cumulative Number of Reported Claims | claim 12,422        
Short-duration Insurance Contracts, Liability for Unpaid Claims and Allocated Claim Adjustment Expense, Net [Abstract]          
Cumulative Paid Losses and Allocated LAE, Net $ 100.6