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Fair Value of Financial Instruments (Details) (USD $)
In Millions, unless otherwise specified
Dec. 31, 2013
Dec. 31, 2012
Fair Value, Balance Sheet Grouping, Financial Statement Captions    
Senior notes $ 676.4 $ 751.2
2012 OBH Senior Notes
   
Fair Value, Balance Sheet Grouping, Financial Statement Captions    
Senior notes 274.7 274.7
Fair value | 2012 OBH Senior Notes
   
Fair Value, Balance Sheet Grouping, Financial Statement Captions    
Senior notes 269.8 282.4
Fair value | SIG Senior Notes
   
Fair Value, Balance Sheet Grouping, Financial Statement Captions    
Senior notes 438.1 441.9
Fair value | SIG Preference Shares
   
Fair Value, Balance Sheet Grouping, Financial Statement Captions    
Senior notes 260.0 257.5
Carrying Value | 2012 OBH Senior Notes
   
Fair Value, Balance Sheet Grouping, Financial Statement Captions    
Senior notes 274.7 274.7
Carrying Value | SIG Senior Notes
   
Fair Value, Balance Sheet Grouping, Financial Statement Captions    
Senior notes 399.6 399.4
Carrying Value | SIG Preference Shares
   
Fair Value, Balance Sheet Grouping, Financial Statement Captions    
Senior notes $ 250.0 $ 250.0