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Significant Transactions (Dispositions) (Details) - USD ($)
3 Months Ended 9 Months Ended 12 Months Ended
Feb. 26, 2019
Sep. 28, 2017
Jul. 21, 2016
Apr. 18, 2016
Dec. 31, 2019
Sep. 30, 2019
Jun. 30, 2019
Mar. 31, 2019
Dec. 31, 2018
Sep. 30, 2018
Jun. 30, 2018
Mar. 31, 2018
Sep. 30, 2018
Sep. 28, 2017
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Significant Transactions                                  
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold                             $ 0 $ 0 $ 1,131,000,000.0
Gain (loss) on sale of other discontinued operations, net of tax                             800,000 (17,200,000) 557,000,000.0
Other comprehensive (loss) income, net of tax                             (1,400,000) (4,800,000) 300,000
Net income from discontinued operations, net of tax         $ (800,000) $ 900,000 $ 0 $ 700,000 $ 0 $ (17,300,000) $ 0 $ 100,000     0 0 20,500,000
Tranzact                                  
Significant Transactions                                  
Proceeds from dividends received     $ 221,300,000                            
MediaAlpha                                  
Significant Transactions                                  
Proceeds from dividends received $ 89,300,000                                
Realized gain from transaction               67,500,000             67,500,000    
Ownership interest (as a percent) 48.30%                                
Fully diluted ownership interest (as a percent) 42.00%                                
Assets, fair value               114,700,000                  
Unrealized investment gain               $ 114,700,000             180,000,000.0    
Total realized and unrealized gain on sale of minority stake                             182,200,000    
OneBeacon                                  
Significant Transactions                                  
Sale of Stock, Price Per Share   $ 18.10                       $ 18.10      
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold   $ 1,300,000,000                              
Gain (loss) on sale of other discontinued operations, net of tax   554,600,000                              
Other comprehensive (loss) income, net of tax   $ 2,900,000                              
Net income from discontinued operations, net of tax                           $ 20,500,000      
Tranzact                                  
Significant Transactions                                  
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold     $ 221,300,000                            
Gain (loss) on sale of other discontinued operations, net of tax                               3,200,000 3,200,000
Sirius Group                                  
Significant Transactions                                  
Sales of unconsolidated affiliates and consolidated subsidiaries, net of cash sold       $ 2,600,000,000                          
Gain (loss) on sale of other discontinued operations, net of tax                               (17,300,000)  
Disposal group, consideration       $ 2,600,000,000                          
Discontinued Operations | OneBeacon                                  
Significant Transactions                                  
Gain (loss) on sale of other discontinued operations, net of tax                                 554,500,000
Net income from discontinued operations, net of tax                                 20,500,000
Discontinued Operations | Tranzact                                  
Significant Transactions                                  
Gain (loss) on sale of other discontinued operations, net of tax                                 3,200,000
Net income from discontinued operations, net of tax                                 0
Discontinued Operations | Sirius Group                                  
Significant Transactions                                  
Gain (loss) on sale of other discontinued operations, net of tax                             800,000 $ (17,200,000) (700,000)
Net income from discontinued operations, net of tax                                 $ 0
Swedish Tax Authority | Sirius Group | Sirius Group                                  
Significant Transactions                                  
Net income from discontinued operations, net of tax                         $ (17,300,000)   $ 800,000    
MediaAlpha                                  
Significant Transactions                                  
Ownership interest (as a percent)         48.30%                   48.30%