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Significant Transactions (Details)
 3 Months Ended 9 Months Ended
May 11, 2018
USD ($)
Jan. 24, 2018
USD ($)
Oct. 05, 2017
USD ($)
shares
Sep. 28, 2017
USD ($)
Sep. 30, 2018
USD ($)
Sep. 30, 2017
USD ($)
Sep. 30, 2018
USD ($)
earnout_period
Sep. 30, 2017
USD ($)
May 18, 2018
USD ($)
Feb. 05, 2018
USD ($)
Dec. 31, 2017
USD ($)
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Purchases of consolidated subsidiaries, net of cash acquired             $ 252,100,000 $ 0      
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold             0 1,131,000,000      
Net (loss) gain from sale of discontinued operations, net of tax           $ 554,300,000 (17,200,000) $ 552,700,000      
NSM Holding Co LLC                      
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Contingent consideration         $ 2,600,000   2,600,000        
Contingent consideration earnout liabilities         $ 20,100,000   $ 20,100,000       $ 0
Healthplans.com                      
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Purchases of consolidated subsidiaries, net of cash acquired     $ 28,000,000                
MediaAlpha                      
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Ownership interest (as a percent)         62.20%   62.20%       64.40%
OneBeacon                      
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold       $ 1,300,000,000              
Net (loss) gain from sale of discontinued operations, net of tax       $ 554,600,000              
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%                    
Purchases of consolidated subsidiaries, net of cash acquired $ 274,200,000.0                    
Purchase price adjustment         $ 2,100,000            
Assets acquired 495,200,000                    
Goodwill and intangible assets acquired 383,000,000                    
Liabilities acquired 204,600,000                    
Noncontrolling interest acquired 14,400,000                    
Transaction costs         6,300,000            
Contingent consideration $ 10,200,000                    
Number of earnout periods | earnout_period             2        
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%    
Purchase price adjustment         $ 700,000            
Assets acquired                 $ 72,600,000    
Goodwill and intangible assets acquired                 54,600,000    
Liabilities acquired                 22,300,000    
Equity method investment, aggregate cost                 49,600,000    
Contingent consideration                 $ 7,500,000    
DavidShield                      
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%       0.00%
DavidShield & PassportCard                      
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Equity method investment, aggregate cost   $ 41,800,000                  
Payments to acquire business, net   $ 28,300,000                  
PassportCard                      
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%       50.00%
PassportCard | White Mountains                      
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Ownership interest (as a percent)         25.00%   25.00%        
Kudu Investment Management, LLC                      
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Ownership interest (as a percent)         49.50%   49.50%       0.00%
Equity method investment, aggregate cost         $ 12,300,000   $ 12,300,000     $ 127,500,000  
Additional funding         63,000,000   63,000,000     $ 125,000,000  
Kudu Investment Management, LLC | White Mountains                      
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Additional funding         $ 31,500,000   $ 31,500,000        
Capital Unit, Class A | MediaAlpha                      
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]                      
Capital units, purchased | shares     131,579                
Capital units, value     $ 12,500,000