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Non-controlling Interest (Details) - USD ($)
$ in Millions
Sep. 30, 2017
Dec. 31, 2016
Noncontrolling Interest [Line Items]    
Total non-controlling interests $ (131.6) $ 133.3
Total Non-Controlling Excluding Reciprocals    
Noncontrolling Interest [Line Items]    
Total non-controlling interests $ 28.6 $ 35.2
OneBeacon    
Noncontrolling Interest [Line Items]    
Noncontrolling equity percentage 0.00% 23.90%
Total non-controlling interests $ 0.0 $ 244.6
HG Global    
Noncontrolling Interest [Line Items]    
Noncontrolling equity percentage 3.10% 3.10%
Total non-controlling interests $ 16.1 $ 16.6
MediaAlpha    
Noncontrolling Interest [Line Items]    
Noncontrolling equity percentage 40.00% 40.00%
Total non-controlling interests $ 9.5 $ 11.7
Buzzmove    
Noncontrolling Interest [Line Items]    
Noncontrolling equity percentage 22.90% 29.10%
Total non-controlling interests $ 3.0 $ 2.9
WOBI    
Noncontrolling Interest [Line Items]    
Noncontrolling equity percentage 5.00% 5.00%
Total non-controlling interests $ 0.0 $ 0.1
AWG Dewar    
Noncontrolling Interest [Line Items]    
Noncontrolling equity percentage 0.00% 18.80%
Total non-controlling interests $ 0.0 $ 3.9
Build America Mutual    
Noncontrolling Interest [Line Items]    
Noncontrolling equity percentage 100.00% 100.00%
Total non-controlling interests $ (160.2) $ (150.9)
Star & Shield Insurance Exchange    
Noncontrolling Interest [Line Items]    
Noncontrolling equity percentage 0.00% 100.00%
Total non-controlling interests $ 0.0 $ 4.4
Star & Shield Insurance Exchange | Total mutual and reciprocals    
Noncontrolling Interest [Line Items]    
Total non-controlling interests $ (160.2) $ (146.5)