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Significant Transactions (Details)
 3 Months Ended 5 Months Ended 12 Months Ended
Jun. 28, 2019
USD ($)
Apr. 04, 2019
USD ($)
Apr. 01, 2019
USD ($)
Feb. 26, 2019
USD ($)
Dec. 03, 2018
USD ($)
May 11, 2018
USD ($)
Mar. 31, 2020
USD ($)
earnout_period
Dec. 31, 2019
USD ($)
Mar. 31, 2019
USD ($)
Sep. 30, 2018
USD ($)
Dec. 31, 2019
USD ($)
May 31, 2019
USD ($)
Apr. 03, 2019
USD ($)
May 18, 2018
USD ($)
Feb. 05, 2018
USD ($)
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Ownership interest (as a percent)             50.00% 50.00%     50.00%        
Commitment to Fund                             $ 125,000,000.0
Payments to Acquire Businesses and Interest in Affiliates             $ 0   $ 9,600,000            
Payments to acquire business, net   $ 81,400,000                          
Goodwill             392,400,000 $ 394,700,000     $ 394,700,000        
NSM Holding Co LLC                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Change in fair value of contingent consideration earnout liabilities             (600,000)   1,300,000 $ 2,600,000          
Payment for contingent consideration liability             6,400,000                
Contingent consideration earnout liabilities             13,400,000 20,600,000     20,600,000        
White Mountains                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Other Investments             805,600,000 $ 856,300,000     856,300,000        
MediaAlpha                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Ownership interest (as a percent)       48.30%                      
Fully diluted ownership interest (as a percent)       42.00%                      
Proceeds from dividends received       $ 89,300,000                      
Net gain from sale of discontinued operations, net of tax                 67,500,000            
Assets, fair value       $ 114,700,000         114,700,000            
Unrealized investment gain             30,000,000.0   114,700,000   $ 180,000,000.0        
Total realized and unrealized gain on sale of minority stake             $ 182,200,000                
Elementum Holdings, L.P.                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Ownership interest (as a percent)             30.00% 30.00%     30.00% 30.00%      
Other Investments                       $ 55,100,000      
Insurance-Linked Securities Funds                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Commitment to Fund                       $ 50,000,000.0      
Elementum Funds                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Equity method investment, aggregate cost             $ 46,200,000                
NSM Insurance HoldCo, LLC                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Ownership interest (as a percent)           95.00% 96.40%                
Payments to Acquire Businesses and Interest in Affiliates           $ 274,200,000                  
Number of earnout periods | earnout_period             2                
Fully diluted ownership interest (as a percent)           83.60% 88.40%                
Fresh Insurance Services Group Limited                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Ownership interest (as a percent)                           100.00%  
Equity method investment, aggregate cost                           $ 49,600,000  
Purchase price adjustment                 700,000            
Proceeds from borrowings         $ 51,000,000.0                    
Fresh Insurance Services Group Limited | NSM Holding Co LLC                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Purchase price adjustment                 5,900,000            
KBK Insurance Group, Inc. & KBK Premium Services, Inc.                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Payments to Acquire Businesses and Interest in Affiliates         60,000,000.0                    
Goodwill and intangible assets acquired         59,400,000       32,600,000            
Stock Issued During Period, Value, Acquisitions         29,000,000.0                    
Proceeds from borrowings         $ 30,100,000                    
Intangible assets acquired                 32,700,000            
AIG Collector Car Business                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Payments to Acquire Businesses and Interest in Affiliates $ 82,500,000                            
Intangible assets acquired 82,500,000                            
AIG Collector Car Business | NSM Holding Co LLC                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Proceeds from borrowings 22,500,000                            
AIG Collector Car Business | White Mountains                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Stock Issued During Period, Value, Acquisitions $ 59,100,000                            
Kudu investments                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Ownership interest (as a percent)   99.10%           49.50%     49.50%   49.50%   49.50%
Assets acquired   $ 155,500,000                          
Liabilities acquired   800,000                          
Noncontrolling interest acquired   $ 1,500,000                          
Fully diluted ownership interest (as a percent)   85.40%           42.70%     42.70%   42.70%   42.70%
Unfunded capital commitment   $ 250,000,000.0         $ 122,500,000 $ 129,000,000.0     $ 129,000,000.0   $ 250,000,000.0    
Goodwill   7,600,000                          
Business Combination, Recognized Identifiable Assets Acquired and Liabilities Assumed, Finite-Lived Intangibles   $ 2,200,000                          
Increase (Decrease) in Capital Commitment               100,000,000.0              
Funded Capital Commitment               350,000,000.0     350,000,000.0        
NSM Bank Facility | NSM Holding Co LLC                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Long-term line of credit           $ 100,000,000.0                  
NSM Bank Facility | Term Loan | NSM Holding Co LLC                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Long-term line of credit           $ 224,000,000.0 220,700,000 221,300,000     221,300,000        
Proceeds from borrowings                 $ 6,500,000            
Kudu Debt [Member] | Delayed Draw Term Loans [Member] | Kudu                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Total commitment under revolving credit facility               125,000,000.0     125,000,000.0        
Line of Credit Facility, Remaining Borrowing Capacity             $ 56,000,000.0 $ 68,000,000.0     $ 68,000,000.0        
Embrace Pet Insurance                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Goodwill and intangible assets acquired     $ 67,600,000                        
Intangible assets acquired     15,400,000                        
Goodwill     52,200,000                        
Embrace Pet Insurance | NSM Holding Co LLC                              
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                              
Stock Issued During Period, Value, Acquisitions     58,200,000                        
Proceeds from borrowings     $ 20,400,000                        
Percentage of voting interests acquired     100.00%                        
Payments to acquire businesses, gross     $ 71,500,000