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Intangible Assets and Goodwill - Narrative (Details) - USD ($)
$ in Thousands
 3 Months Ended 9 Months Ended 12 Months Ended
Dec. 18, 2017
Jan. 01, 2017
Oct. 31, 2016
Sep. 22, 2016
Jan. 19, 2016
Apr. 05, 2005
Sep. 30, 2018
Sep. 30, 2017
Sep. 30, 2018
Sep. 30, 2017
Dec. 31, 2017
Sep. 18, 2018
Jun. 30, 2018
Jun. 30, 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   1,900 24,600 1,900 24,600 2,300   $ 2,000 $ 25,100 $ 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 6,000 $ 2,700 6,000 2,900   2,700 6,300 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             1,100 1,400 1,100 1,400 1,400   1,200 1,500 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   0 700 0 700 0   0 800 900
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             400 2,700 $ 400 2,700 700   $ 500 $ 3,000 $ 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)                            
Disposed of by Sale | AgriLogic Consulting, LLC | Consulting Relationships                              
Finite And Indefinite Lived Intangible Assets By Major Class [Line Items]                              
Sale of interest of consulting business                       60.00%