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Income Taxes - Schedule of Significant Components of Deferred Tax Assets and Liabilities (Details) (USD $)
In Thousands, unless otherwise specified
Dec. 31, 2014
Dec. 31, 2013
Deferred tax assets:    
Employee deferred compensation plans $ 30,969us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsEmployeeCompensation $ 31,213us-gaap_DeferredTaxAssetsTaxDeferredExpenseCompensationAndBenefitsEmployeeCompensation
Deferred rent 10,024us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsDeferredRent 10,451us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsDeferredRent
Lease incentive 6,212opy_DeferredTaxAssetsOperatingLeasesAndLeaseIncentives 6,693opy_DeferredTaxAssetsOperatingLeasesAndLeaseIncentives
Broker notes 3,460opy_DeferredTaxAssetsBrokerNotes 3,915opy_DeferredTaxAssetsBrokerNotes
Auction rate securities reserve 3,229opy_DeferredTaxAssetsAuctionRateSecuritiesValuationAllowance 3,669opy_DeferredTaxAssetsAuctionRateSecuritiesValuationAllowance
Net operating loss 2,896us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsDomestic 4,587us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsDomestic
Involuntary conversion 2,033opy_DeferredTaxAssetsInvoluntaryConversion 1,866opy_DeferredTaxAssetsInvoluntaryConversion
Reserve for litigation and legal fees 5,808us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLegalSettlements 1,659us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsLegalSettlements
Allowance for doubtful accounts 984us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsAllowanceForDoubtfulAccounts 1,002us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsAllowanceForDoubtfulAccounts
State and local net operating loss/credit carryforward 357us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsStateAndLocal 1,993us-gaap_DeferredTaxAssetsOperatingLossCarryforwardsStateAndLocal
Other 2,650us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsOther 2,757us-gaap_DeferredTaxAssetsTaxDeferredExpenseReservesAndAccrualsOther
Total deferred tax assets 68,622us-gaap_DeferredTaxAssetsGross 69,805us-gaap_DeferredTaxAssetsGross
Valuation allowance 113us-gaap_DeferredTaxAssetsValuationAllowance 138us-gaap_DeferredTaxAssetsValuationAllowance
Deferred tax assets after valuation allowance 68,509us-gaap_DeferredTaxAssetsNet 69,667us-gaap_DeferredTaxAssetsNet
Deferred tax liabilities:    
Goodwill amortization (Section 197) 48,025us-gaap_DeferredTaxLiabilitiesGoodwillAndIntangibleAssetsGoodwill 43,728us-gaap_DeferredTaxLiabilitiesGoodwillAndIntangibleAssetsGoodwill
Partnership investments 10,865opy_DeferredTaxLiabilitiesInvestmentsInPartnerships 12,039opy_DeferredTaxLiabilitiesInvestmentsInPartnerships
Mortgage servicing rights 12,173us-gaap_DeferredTaxLiabilitiesMortgageServicingRights 9,889us-gaap_DeferredTaxLiabilitiesMortgageServicingRights
Company owned life insurance 6,501opy_DeferredTaxLiabilitiesInsuranceReceivables 5,173opy_DeferredTaxLiabilitiesInsuranceReceivables
Change in accounting method 2,591opy_DeferredTaxLiabilitiesChangeInMethodOfAccounting 3,895opy_DeferredTaxLiabilitiesChangeInMethodOfAccounting
Book versus tax depreciation differences 982us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment 1,437us-gaap_DeferredTaxLiabilitiesPropertyPlantAndEquipment
Other 469us-gaap_DeferredTaxLiabilitiesOther 602us-gaap_DeferredTaxLiabilitiesOther
Total deferred tax liabilities 81,606us-gaap_DeferredTaxLiabilities 76,763us-gaap_DeferredTaxLiabilities
Deferred tax liabilities, net $ (13,097)us-gaap_DeferredTaxAssetsLiabilitiesNet $ (7,096)us-gaap_DeferredTaxAssetsLiabilitiesNet