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Investments - Debt and Short-term Investments (Details) - USD ($)
3 Months Ended 9 Months Ended
Sep. 30, 2021
Sep. 30, 2020
Sep. 30, 2021
Sep. 30, 2020
Dec. 31, 2020
Investment Holdings [Line Items]          
Other investments $ 52,480,000   $ 52,480,000   $ 54,232,000
Investment in federal home loan bank stock us-gaap:AssetPledgedAsCollateralMember   us-gaap:AssetPledgedAsCollateralMember   us-gaap:AssetPledgedAsCollateralMember
Cash and Short-term Investments          
Investment amount $ 158,721,000   $ 158,721,000   $ 128,382,000
Cash 89,618,000   89,618,000   62,217,000
Other Investments in Unconsolidated Investees          
Cash and Short-term Investments          
Investment amount 5,700,000   5,700,000    
Unfunded commitments 15,000,000.0   15,000,000.0    
Maui Jim Inc.          
Cash and Short-term Investments          
Investment amount 110,600,000   110,600,000    
Prime Holdings Insurance Services, Inc. (Prime)          
Cash and Short-term Investments          
Investment amount 42,400,000   42,400,000    
FHLBC          
Investment Holdings [Line Items]          
Investments pledged as collateral 9,100,000   9,100,000    
Federal home loan bank borrowings fair value disclosure 0   0    
Investment In Low Income Housing Tax Credit Partnership Net Of Amortization          
Investment Holdings [Line Items]          
Other investments 17,400,000   17,400,000   20,300,000
Total tax benefit on investments in housing tax credit partnership 900,000 $ 900,000 2,700,000 $ 2,600,000  
Qualified affordable housing project investments, commitment 2,100,000   2,100,000    
Investment in Private Funds          
Investment Holdings [Line Items]          
Other investments 31,400,000   31,400,000   $ 32,100,000
Fair value investments entities that calculate net asset value per share unfunded commitments $ 9,600,000   $ 9,600,000