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Reserves for Losses and Loss Adjustment Expenses - Incurred Losses and Loss Adjustment Expenses, Net of Reinsurance (Details) - USD ($)
$ in Millions
Dec. 31, 2023
Dec. 31, 2022
Dec. 31, 2021
Dec. 31, 2020
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Dec. 31, 2016
Dec. 31, 2015
Specialty                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance $ 1,399.4                
Total of IBNR plus expected development on reported losses 462.6                
Specialty | 2015                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 0.0 $ 0.0 $ 0.0 $ 0.0 $ 0.0 $ 0.0 $ 0.2 $ 1.1 $ 2.2
Total of IBNR plus expected development on reported losses 0.0                
Specialty | 2016                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 1.9 1.9 2.4 2.2 3.4 3.5 4.2 10.1  
Total of IBNR plus expected development on reported losses 0.2                
Specialty | 2017                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 2.0 1.8 2.0 2.0 2.4 5.6 9.1    
Total of IBNR plus expected development on reported losses 0.0                
Specialty | 2018                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 13.4 13.0 11.5 11.2 13.6 10.1      
Total of IBNR plus expected development on reported losses 0.1                
Specialty | 2019                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 50.0 41.1 29.9 24.1 28.7        
Total of IBNR plus expected development on reported losses 8.1                
Specialty | 2020                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 47.7 46.9 49.0 72.5          
Total of IBNR plus expected development on reported losses 2.1                
Specialty | 2021                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 214.6 196.9 219.4            
Total of IBNR plus expected development on reported losses 6.2                
Specialty | 2022                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 527.0 514.7              
Total of IBNR plus expected development on reported losses 165.9                
Specialty | 2023                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 542.8                
Total of IBNR plus expected development on reported losses 280.0                
Bespoke                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 430.7                
Total of IBNR plus expected development on reported losses 154.8                
Bespoke | 2015                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 0.0 0.0 0.0 0.0 0.1 0.0 0.2 0.4 0.4
Total of IBNR plus expected development on reported losses 0.0                
Bespoke | 2016                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 2.2 2.2 2.4 3.9 4.8 6.2 6.1 9.1  
Total of IBNR plus expected development on reported losses 0.2                
Bespoke | 2017                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 7.5 7.9 9.4 10.9 11.3 10.8 17.8    
Total of IBNR plus expected development on reported losses 0.6                
Bespoke | 2018                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 16.1 17.9 18.4 20.0 23.4 34.5      
Total of IBNR plus expected development on reported losses (7.3)                
Bespoke | 2019                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 24.1 21.2 28.9 26.6 38.9        
Total of IBNR plus expected development on reported losses 3.3                
Bespoke | 2020                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 74.1 79.0 71.8 86.1          
Total of IBNR plus expected development on reported losses (69.4)                
Bespoke | 2021                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 47.3 57.8 83.9            
Total of IBNR plus expected development on reported losses 18.1                
Bespoke | 2022                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 132.7 152.7              
Total of IBNR plus expected development on reported losses 103.0                
Bespoke | 2023                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 126.7                
Total of IBNR plus expected development on reported losses 106.3                
Reinsurance                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 1,074.6                
Total of IBNR plus expected development on reported losses 186.8                
Reinsurance | 2015                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 2.9 2.8 2.8 2.8 2.8 2.8 6.4 7.2 $ 8.9
Total of IBNR plus expected development on reported losses 0.0                
Reinsurance | 2016                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 32.4 40.4 40.7 44.7 48.2 53.5 60.6 $ 73.5  
Total of IBNR plus expected development on reported losses 10.0                
Reinsurance | 2017                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 50.8 55.2 59.5 55.5 51.6 58.7 $ 86.5    
Total of IBNR plus expected development on reported losses 9.8                
Reinsurance | 2018                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 73.4 89.1 86.0 87.3 95.5 $ 84.7      
Total of IBNR plus expected development on reported losses 1.8                
Reinsurance | 2019                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 43.7 51.8 60.2 58.9 $ 50.9        
Total of IBNR plus expected development on reported losses 3.0                
Reinsurance | 2020                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 240.7 244.2 226.4 $ 193.1          
Total of IBNR plus expected development on reported losses 26.5                
Reinsurance | 2021                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 389.5 391.8 $ 364.7            
Total of IBNR plus expected development on reported losses 36.3                
Reinsurance | 2022                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 149.0 $ 175.6              
Total of IBNR plus expected development on reported losses 41.2                
Reinsurance | 2023                  
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]                  
Incurred losses and loss adjustment expenses – net of reinsurance 92.2                
Total of IBNR plus expected development on reported losses $ 58.2