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Business Combinations - Purchase Price Allocation for Current Year Acquisitions and Adjustments Made for Prior Year Acquisitions (Details) - USD ($)
$ in Thousands
 12 Months Ended
Dec. 31, 2019
Dec. 31, 2018
Dec. 31, 2017
Business Combination Separately Recognized Transactions [Line Items]      
Cash paid $ 356,260 $ 934,928 $ 41,471
Common Stock Issued 20,000 100,000  
Other payable 12,135 5,462 11,708
Recorded earn-out payable 82,872 77,377 6,921
Net assets acquired 471,267 1,117,767 60,100
Maximum potential earn- out payable 162,023 147,668 27,451
Smith Insurance Associates, Inc. (Smith)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 22,833    
Smith Insurance Associates, Inc. (Smith) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Feb. 01, 2019    
Cash paid $ 20,129    
Recorded earn-out payable 2,704    
Net assets acquired 22,833    
Maximum potential earn- out payable 4,550    
Donald P. Pipino Company, LTD (Pipino)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 26,376    
Donald P. Pipino Company, LTD (Pipino) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Feb. 01, 2019    
Cash paid $ 16,420    
Other payable 135    
Recorded earn-out payable 9,821    
Net assets acquired 26,376    
Maximum potential earn- out payable $ 12,996    
AGA Enterprises, LLC d/b/a Cossio Insurance Agency (Cossio) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Mar. 01, 2019    
Cash paid $ 13,990    
Other payable 10    
Recorded earn-out payable 696    
Net assets acquired 14,696    
Maximum potential earn- out payable 2,000    
Medval, LLC (Medval)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 30,890    
Medval, LLC (Medval) | Services      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Mar. 01, 2019    
Cash paid $ 29,106    
Other payable 100    
Recorded earn-out payable 1,684    
Net assets acquired 30,890    
Maximum potential earn- out payable 2,500    
United Development Systems, Inc. (United)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 22,643    
United Development Systems, Inc. (United) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition May 01, 2019    
Cash paid $ 18,987    
Other payable 388    
Recorded earn-out payable 3,268    
Net assets acquired 22,643    
Maximum potential earn- out payable 8,625    
Twinbrook Insurance Brokerage, Inc. (Twinbrook)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 28,216    
Twinbrook Insurance Brokerage, Inc. (Twinbrook) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Jun. 01, 2019    
Cash paid $ 26,251    
Other payable 400    
Recorded earn-out payable 1,565    
Net assets acquired 28,216    
Maximum potential earn- out payable 5,073    
Innovative Risk Solutions, Inc. (IRS)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 35,009    
Innovative Risk Solutions, Inc. (IRS) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Jul. 01, 2019    
Cash paid $ 26,435    
Other payable 2,465    
Recorded earn-out payable 6,109    
Net assets acquired 35,009    
Maximum potential earn- out payable 9,000    
WBR Insurance Agency, LLC et al (WBR)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 13,067    
WBR Insurance Agency, LLC et al (WBR) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Aug. 01, 2019    
Cash paid $ 10,667    
Other payable 203    
Recorded earn-out payable 2,197    
Net assets acquired 13,067    
Maximum potential earn- out payable 4,575    
West Ridge Insurance Agency, Inc. d/b/a Yozell Associates (Yozell)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 14,268    
West Ridge Insurance Agency, Inc. d/b/a Yozell Associates (Yozell) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Aug. 01, 2019    
Cash paid $ 13,030    
Other payable 470    
Recorded earn-out payable 768    
Net assets acquired 14,268    
Maximum potential earn- out payable 6,730    
CKP Insurance, LLC (CKP)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 151,283    
CKP Insurance, LLC (CKP) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Aug. 01, 2019    
Cash paid $ 89,190    
Common Stock Issued 20,000    
Other payable 4,000    
Recorded earn-out payable 38,093    
Net assets acquired 151,283    
Maximum potential earn- out payable $ 76,500    
Poole Professional Ltd. Insurance Agents and Brokers et al (Poole) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Oct. 01, 2019    
Cash paid $ 32,358    
Other payable 75    
Recorded earn-out payable 4,556    
Net assets acquired 36,989    
Maximum potential earn- out payable 6,850    
Other Acquisitions      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   37,556  
Other Acquisitions | Various      
Business Combination Separately Recognized Transactions [Line Items]      
Cash paid 36,665 30,293 41,471
Other payable 2,391 1,367 11,708
Recorded earn-out payable 9,026 5,896 6,921
Net assets acquired 48,082 37,556 60,100
Maximum potential earn- out payable 14,454 12,998 $ 27,451
VerHagen Glendenning & Walker LLP (VGW)      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired $ 26,915    
VerHagen Glendenning & Walker LLP (VGW) | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition Oct. 01, 2019    
Cash paid $ 23,032    
Other payable 1,498    
Recorded earn-out payable 2,385    
Net assets acquired 26,915    
Maximum potential earn- out payable $ 8,170    
Opus      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 22,984  
Opus | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Feb. 01, 2018  
Cash paid   $ 20,400  
Other payable   200  
Recorded earn-out payable   2,384  
Net assets acquired   22,984  
Maximum potential earn- out payable   3,600  
Kerxton      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 16,746  
Kerxton | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Mar. 01, 2018  
Cash paid   $ 13,176  
Other payable   1,490  
Recorded earn-out payable   2,080  
Net assets acquired   16,746  
Maximum potential earn- out payable   2,920  
ADG      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 47,575  
ADG | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   May 01, 2018  
Cash paid   $ 29,471  
Other payable   559  
Recorded earn-out payable   17,545  
Net assets acquired   47,575  
Maximum potential earn- out payable   20,000  
Servco      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 77,179  
Servco | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Jun. 01, 2018  
Cash paid   $ 76,245  
Recorded earn-out payable   934  
Net assets acquired   77,179  
Maximum potential earn- out payable   7,000  
Tower Hill      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 21,488  
Tower Hill | National Programs      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Jul. 01, 2018  
Cash paid   $ 20,300  
Recorded earn-out payable   1,188  
Net assets acquired   21,488  
Maximum potential earn- out payable   7,700  
HSR      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 22,123  
HSR | National Programs      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Jul. 01, 2018  
Cash paid   $ 20,132  
Recorded earn-out payable   1,991  
Net assets acquired   22,123  
Maximum potential earn- out payable   9,000  
PDA      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 24,843  
PDA | Services      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Jul. 01, 2018  
Cash paid   $ 15,025  
Recorded earn-out payable   9,818  
Net assets acquired   24,843  
Maximum potential earn- out payable   17,975  
F&I      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 54,471  
F&I | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Sep. 01, 2018  
Cash paid   $ 44,940  
Other payable   410  
Recorded earn-out payable   9,121  
Net assets acquired   54,471  
Maximum potential earn- out payable   19,500  
Rodman      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 35,102  
Rodman | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Nov. 01, 2018  
Cash paid   $ 31,121  
Other payable   261  
Recorded earn-out payable   3,720  
Net assets acquired   35,102  
Maximum potential earn- out payable   9,850  
Hays      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 724,600  
Hays | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Nov. 16, 2018  
Cash paid   $ 605,000  
Common Stock Issued   100,000  
Recorded earn-out payable   19,600  
Net assets acquired   724,600  
Maximum potential earn- out payable   25,000  
Dealer Associates      
Business Combination Separately Recognized Transactions [Line Items]      
Net assets acquired   $ 33,100  
Dealer Associates | Retail      
Business Combination Separately Recognized Transactions [Line Items]      
Effective date of acquisition   Dec. 01, 2018  
Cash paid   $ 28,825  
Other payable   1,175  
Recorded earn-out payable   3,100  
Net assets acquired   33,100  
Maximum potential earn- out payable   $ 12,125