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Intangible Assets and Goodwill - Narrative (Details) - USD ($)
$ in Thousands
 3 Months Ended 6 Months Ended 12 Months Ended
Dec. 18, 2017
Jan. 01, 2017
Oct. 31, 2016
Sep. 22, 2016
Jan. 19, 2016
Apr. 05, 2005
Jun. 30, 2018
Jun. 30, 2017
Jun. 30, 2018
Jun. 30, 2017
Dec. 31, 2017
Mar. 31, 2018
Mar. 31, 2017
Dec. 31, 2016
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Contingent consideration         $ 14,100                  
Consideration Transferred, Other         22,800                  
Ceding commission         2,000                  
Consideration transferred         69,100                  
Software acquired         12,000                  
Residual assets         300                  
Total assets acquired, net         $ 47,000                  
Goodwill             $ 0 $ 0 $ 0 $ 1,800        
Impairment charge                     $ 3,400      
AgriLogic                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Percentage of interests acquired         100.00%                  
Aggregate consideration for sale and purchase agreement         $ 53,000                  
Goodwill         22,100                  
Intangible assets, expected tax deductible amount         34,000                  
Goodwill, expected tax deductible amount         $ 21,000                  
Eligible tax deduction period         15 years                  
Blue Waters                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Percentage of interests acquired     100.00%                      
Consideration transferred     $ 8,000                      
Residual assets     300                      
Total assets acquired, net     5,750                      
Goodwill     2,100                      
Agency Relationships                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset         $ 25,000   2,000 25,100 2,000 25,100 2,300 $ 2,200 $ 25,800 $ 26,200
Intangible Assets, Additions             0 0 $ 0 0        
Asset amortization period                 15 years          
Trademark                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset         4,000   2,700 6,300 $ 2,700 6,300 2,900 2,800 6,400 6,600
Intangible Assets, Additions             0 0 $ 0 0        
Asset amortization period                 10 years          
Trademark | Blue Waters                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset     1,500                      
Asset amortization period                 5 years          
Insurance Licenses                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset             16,700 16,700 $ 16,700 16,700 16,700 16,700 16,700 16,700
Intangible Assets, Additions             0 0 0 0        
Insurance Licenses | Blue Waters                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of trading licenses     50                      
Contractual Rights                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset             1,200 1,500 1,200 1,500 1,400 1,300 1,600 1,700
Intangible Assets, Additions             0 0 0 0        
Consulting Relationships                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset         1,000   0 800 0 800 0 0 900 900
Intangible Assets, Additions             0 0 $ 0 0        
Asset amortization period                 10 years          
Customer Lists | Blue Waters                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset     3,100                      
Asset amortization period                 5 years          
Non-compete Agreements                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset             500 3,000 $ 500 3,000 700 $ 600 $ 3,100 $ 3,300
Intangible Assets, Additions         2,900   0 $ 0 $ 0 $ 0        
Asset amortization period                   5 years        
Non-compete Agreements | Blue Waters                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset     $ 1,000                      
Asset amortization period                 5 years          
Value of Business Acquired | AgriLogic                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Intangible Assets, Additions         $ 1,800                  
Crop Re                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Equity method investment, ownership percentage 23.20%                          
Digital Re                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Goodwill   $ 1,800                        
Equity method investment, ownership percentage   49.00%                        
LSML | Insurance Licenses                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset       $ 1,900                    
LSML | Contractual Rights                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Asset amortization period       5 years                    
Aspen U.K.                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Aggregate consideration for sale and purchase agreement           $ 1,600                
Aspen U.K. | Trademark                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset             1,600   $ 1,600   1,600      
Aspen U.K. | Insurance Licenses                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Acquired licenses             2,100   2,100          
AAIC, Aspen Specialty, AIUK | Insurance Licenses                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Value of the asset             16,600   16,600   $ 16,600      
AAIC | Insurance Licenses                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Acquired licenses             10,000   10,000          
Aspen Specialty | Insurance Licenses                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Acquired licenses             $ 4,500   $ 4,500          
Disposed of by Sale | AgriLogic                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Sale of goodwill $ (20,600)                          
Disposed of by Sale | AgriLogic | Trademark                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Intangible assets (disposed) (3,100)                          
Disposed of by Sale | AgriLogic | Customer Lists                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Intangible assets (disposed) (21,800)                          
Disposed of by Sale | AgriLogic | Non-compete Agreements                            
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                            
Intangible assets (disposed) $ (900)