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Goodwill and Other Intangible Assets - Schedule of Acquisition Date Fair Values, Accumulated Amortization and Net Carrying Values for Other Intangibles Assets and Goodwill, By Company (Details) - USD ($)
$ in Millions
 3 Months Ended
Mar. 31, 2024
Dec. 31, 2023
Mar. 31, 2023
Dec. 31, 2022
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill $ 439.2 $ 168.8 $ 168.8 $ 176.5
Other intangible assets, finite-lived, accumulated amortization 22.7 17.0    
Total other intangible assets 320.1 218.8    
Total other intangible assets 297.4 201.8 207.4 215.9
Total goodwill and other intangible assets 759.3 387.6    
Goodwill and other intangible assets 736.6 370.6 $ 376.2 $ 392.4
Other        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, finite-lived, accumulated amortization 22.7 17.0    
Total other intangible assets 297.4 201.8    
Operating Segments | P&C Insurance and Reinsurance (Ark/WM Outrigger)        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill and other intangible assets 292.5 292.5    
Operating Segments | P&C Insurance and Reinsurance (Ark/WM Outrigger) | Ark        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill 116.8 116.8    
Operating Segments | P&C Insurance and Reinsurance (Ark/WM Outrigger) | Ark | Underwriting Capacity        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, indefinite-lived 175.7 175.7    
Operating Segments | Asset Management (Kudu)        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill 7.6 7.6    
Goodwill and other intangible assets $ 8.2 8.3    
Operating Segments | Asset Management (Kudu) | Trade names        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 7 years      
Other intangible assets, finite-lived, acquisition date fair value $ 2.2 2.2    
Other intangible assets, finite-lived, accumulated amortization 1.6 1.5    
Other intangible assets, finite-lived, net carrying value 0.6 0.7    
Operating Segments | P&C Insurance Distribution (Bamboo)        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill 270.4 0.0    
Other intangible assets, finite-lived, acquisition date fair value 101.0 0.0    
Other intangible assets, finite-lived, accumulated amortization 4.2 0.0    
Other intangible assets, finite-lived, net carrying value 96.8 0.0    
Goodwill and other intangible assets $ 367.2 0.0    
Operating Segments | P&C Insurance Distribution (Bamboo) | Trade names        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 10 years      
Other intangible assets, finite-lived, acquisition date fair value $ 23.5 0.0    
Other intangible assets, finite-lived, accumulated amortization 0.5 0.0    
Other intangible assets, finite-lived, net carrying value $ 23.0 0.0    
Operating Segments | P&C Insurance Distribution (Bamboo) | Agency relationships        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 6 years      
Other intangible assets, finite-lived, acquisition date fair value $ 72.4 0.0    
Other intangible assets, finite-lived, accumulated amortization 2.9 0.0    
Other intangible assets, finite-lived, net carrying value $ 69.5 0.0    
Operating Segments | P&C Insurance Distribution (Bamboo) | Developed Technology        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 3 years      
Other intangible assets, finite-lived, acquisition date fair value $ 4.7 0.0    
Other intangible assets, finite-lived, accumulated amortization 0.4 0.0    
Other intangible assets, finite-lived, net carrying value $ 4.3 0.0    
Operating Segments | P&C Insurance Distribution (Bamboo) | Other        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 3 months 18 days      
Other intangible assets, finite-lived, acquisition date fair value $ 0.4 0.0    
Other intangible assets, finite-lived, accumulated amortization 0.4 0.0    
Other intangible assets, finite-lived, net carrying value 0.0 0.0    
Other Operations        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill 44.4 44.4    
Other intangible assets, finite-lived, acquisition date fair value 41.2 40.9    
Other intangible assets, finite-lived, accumulated amortization 16.9 15.5    
Other intangible assets, finite-lived, net carrying value 24.3 25.4    
Goodwill and other intangible assets $ 68.7 69.8    
Other Operations | Trade names        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 13 years 3 months 18 days      
Other intangible assets, finite-lived, acquisition date fair value $ 13.3 13.3    
Other intangible assets, finite-lived, accumulated amortization 4.5 4.1    
Other intangible assets, finite-lived, net carrying value $ 8.8 9.2    
Other Operations | Customer relationships        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 10 years 10 months 24 days      
Other intangible assets, finite-lived, acquisition date fair value $ 24.8 24.8    
Other intangible assets, finite-lived, accumulated amortization 11.1 10.3    
Other intangible assets, finite-lived, net carrying value $ 13.7 14.5    
Other Operations | Other        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 11 years 1 month 6 days      
Other intangible assets, finite-lived, acquisition date fair value $ 3.1 2.8    
Other intangible assets, finite-lived, accumulated amortization 1.3 1.1    
Other intangible assets, finite-lived, net carrying value $ 1.8 $ 1.7