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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 12 Months Ended
Mar. 31, 2021
Mar. 31, 2020
Dec. 31, 2020
Dec. 31, 2019
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill, fair value $ 643.6   $ 525.5  
Goodwill, impairment loss 30.2   0.0  
Goodwill, net carrying value 613.4   525.5  
Other intangible assets, acquisition date fair value 493.7   317.8  
Other intangible assets, accumulated amortization 63.9   54.7  
Impairment of intangible assets, including goodwill 36.4   6.2  
Other intangible assets, impairments 6.2   6.2  
Other intangible assets, net carrying value 423.6   256.9  
Goodwill and other intangible assets 1,037.0   782.4  
Intangible assets and goodwill, fair value 1,137.3   843.3  
Goodwill        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill, impairment loss 30.2 $ 0.0    
Goodwill, net carrying value 613.4 392.4 525.5 $ 394.7
Goodwill, foreign currency translation gain (loss) 1.5 (2.5)    
Other Intangible Assets        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, foreign currency translation gain (loss) 0.2 $ (0.5)    
Non-controlling interest        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill and other intangible assets 108.4   28.1  
Total        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill and other intangible assets 928.6   754.3  
Ark        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill, fair value 116.8   0.0  
Goodwill, impairment loss 0.0   0.0  
Goodwill, net carrying value 116.8   0.0  
Ark | Trade names        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, acquisition date fair value 175.7   0.0  
Other intangible assets, accumulated amortization 0.0   0.0  
Other intangible assets, impairments 0.0   0.0  
Other intangible assets, net carrying value 175.7   0.0  
Specialty Insurance Distribution (NSM)        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill, fair value 507.9   506.4  
Goodwill, impairment loss 30.2   0.0  
Goodwill, net carrying value 477.7   506.4  
Other intangible assets, acquisition date fair value 289.1   288.9  
Other intangible assets, accumulated amortization 60.9   52.3  
Other intangible assets, impairments 6.2   6.2  
Other intangible assets, net carrying value 222.0   230.4  
Specialty Insurance Distribution (NSM) | Goodwill        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill, foreign currency translation gain (loss) 1.5   13.4  
Specialty Insurance Distribution (NSM) | Other Intangible Assets        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, foreign currency translation gain (loss) $ 0.2   1.6  
Specialty Insurance Distribution (NSM) | Customer relationships        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 8 years 10 months 24 days      
Other intangible assets, acquisition date fair value $ 136.4   136.2  
Other intangible assets, accumulated amortization 41.7   36.7  
Other intangible assets, impairments 3.5   3.5  
Other intangible assets, net carrying value $ 91.2   96.0  
Specialty Insurance Distribution (NSM) | Trade names        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 16 years      
Other intangible assets, acquisition date fair value $ 65.4   65.4  
Other intangible assets, accumulated amortization 9.1   8.3  
Other intangible assets, impairments 1.0   1.0  
Other intangible assets, net carrying value 55.3   56.1  
Specialty Insurance Distribution (NSM) | Information technology platform        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, acquisition date fair value 3.1   3.1  
Other intangible assets, accumulated amortization 1.4   1.4  
Other intangible assets, impairments 1.7   1.7  
Other intangible assets, net carrying value $ 0.0   0.0  
Specialty Insurance Distribution (NSM) | Renewal rights        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 12 years      
Other intangible assets, acquisition date fair value $ 82.5   82.5  
Other intangible assets, accumulated amortization 7.6   4.9  
Other intangible assets, impairments 0.0    
Other intangible assets, net carrying value $ 74.9   77.6  
Specialty Insurance Distribution (NSM) | Other Intangible Assets        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 3 years 4 months 24 days      
Other intangible assets, acquisition date fair value $ 1.7   1.7  
Other intangible assets, accumulated amortization 1.1   1.0  
Other intangible assets, impairments 0.0    
Other intangible assets, net carrying value 0.6   0.7  
Kudu        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill, fair value 7.6   7.6  
Goodwill, impairment loss 0.0   0.0  
Goodwill, net carrying value $ 7.6   7.6  
Kudu | Trade names        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 7 years      
Other intangible assets, acquisition date fair value $ 2.2   2.2  
Other intangible assets, accumulated amortization 0.7   0.6  
Other intangible assets, impairments 0.0   0.0  
Other intangible assets, net carrying value 1.5   1.6  
Other Operations        
Acquired Finite-Lived Intangible Assets [Line Items]        
Goodwill, fair value 11.3   11.5  
Goodwill, impairment loss 0.0   0.0  
Goodwill, net carrying value 11.3   11.5  
Other intangible assets, acquisition date fair value 26.7   26.7  
Other intangible assets, accumulated amortization 2.3   1.8  
Other intangible assets, impairments 0.0   0.0  
Other intangible assets, net carrying value $ 24.4   24.9  
Other Operations | Customer relationships        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 10 years 8 months 12 days      
Other intangible assets, acquisition date fair value $ 14.2   14.2  
Other intangible assets, accumulated amortization 1.8   1.4  
Other intangible assets, impairments 0.0   0.0  
Other intangible assets, net carrying value $ 12.4   12.8  
Other Operations | Trade names        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 9 years 7 months 6 days      
Other intangible assets, acquisition date fair value $ 3.6   3.6  
Other intangible assets, accumulated amortization 0.4   0.3  
Other intangible assets, impairments 0.0   0.0  
Other intangible assets, net carrying value $ 3.2   3.3  
Other Operations | Other Intangible Assets        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, weighted average useful life (in years) 5 years 4 months 24 days      
Other intangible assets, acquisition date fair value $ 0.3   0.3  
Other intangible assets, accumulated amortization 0.1   0.1  
Other intangible assets, impairments     0.0  
Other intangible assets, net carrying value 0.2   0.2  
Other Operations | Insurance Licenses        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, acquisition date fair value 8.6   8.6  
Other intangible assets, accumulated amortization 0.0   0.0  
Other intangible assets, impairments 0.0   0.0  
Other intangible assets, net carrying value 8.6   $ 8.6  
Other Operations | Other Operations        
Acquired Finite-Lived Intangible Assets [Line Items]        
Other intangible assets, impairments $ 0.0