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Fair Value Measurement - (Tables)
 6 Months Ended
Nov. 30, 2021
Fair Value Disclosures [Abstract]  
Schedule of Fair Value by Balance Sheet Grouping The following table presents the carrying value and estimated fair value of all of our financial instruments, including those carried at amortized cost, as of November 30, 2021 and May 31, 2021. The table also displays the classification level within the fair value hierarchy based on the degree of observability of the inputs used in the valuation technique for estimating fair value.
Table 12.1: Fair Value of Financial Instruments
 November 30, 2021Fair Value Measurement Level
(Dollars in thousands)Carrying ValueFair ValueLevel 1Level 2Level 3
Assets:    
Cash and cash equivalents$172,742 $172,742 $172,742 $— $— 
Restricted cash11,010 11,010 11,010 — — 
Equity securities, at fair value37,505 37,505 37,505 — — 
Debt securities trading, at fair value588,615 588,615 — 588,615 
Deferred compensation investments7,595 7,595 7,595 — — 
Loans to members, net28,860,735 30,768,917 — — 30,768,917 
Accrued interest receivable108,381 108,381 — 108,381 — 
Derivative assets78,610 78,610 — 78,610 — 
Total financial assets$29,865,193 $31,773,375 $228,852 $775,606 $30,768,917 
Liabilities:  
Short-term borrowings$4,746,935 $4,747,001 $— $4,747,001 $— 
Long-term debt20,804,379 22,255,483 — 12,449,548 9,805,935 
Accrued interest payable120,439 120,439 — 120,439 — 
Guarantee liability10,150 10,884 — — 10,884 
Derivative liabilities615,097 615,097 — 615,097 — 
Subordinated deferrable debt986,415 1,054,992 266,200 788,792 — 
Members’ subordinated certificates1,252,349 1,252,349 — — 1,252,349 
Total financial liabilities$28,535,764 $30,056,245 $266,200 $18,720,877 $11,069,168 
 May 31, 2021Fair Value Measurement Level
(Dollars in thousands)Carrying ValueFair ValueLevel 1Level 2Level 3
Assets:    
Cash and cash equivalents$295,063 $295,063 $295,063 $— $— 
Restricted cash8,298 8,298 8,298 — — 
Equity securities, at fair value35,102 35,102 35,102 — — 
Debt securities trading, at fair value576,175 576,175 — 576,175 — 
Deferred compensation investments7,222 7,222 7,222 — — 
Loans to members, net28,341,429 29,967,692 — — 29,967,692 
Accrued interest receivable107,856 107,856 — 107,856 — 
Derivative assets121,259 121,259 — 121,259 — 
Total financial assets$29,492,404 $31,118,667 $345,685 $805,290 $29,967,692 
Liabilities:  
Short-term borrowings$4,582,096 $4,582,329 $— $4,582,329 $— 
Long-term debt20,603,123 21,799,736 — 12,476,073 9,323,663 
Accrued interest payable123,672 123,672 — 123,672 — 
Guarantee liability10,041 10,841 — — 10,841 
Derivative liabilities584,989 584,989 — 584,989 — 
Subordinated deferrable debt986,315 1,062,748 265,200 797,548 — 
Members’ subordinated certificates1,254,660 1,254,660 — — 1,254,660 
Total financial liabilities$28,144,896 $29,418,975 $265,200 $18,564,611 $10,589,164 
Schedule of the Entity's Assets and Liabilities that are Measured at Fair Value on a Recurring Basis
The following table presents the carrying value and fair value of financial instruments reported in our consolidated financial statements at fair value on a recurring basis as of November 30, 2021 and May 31, 2021, and the classification of the valuation technique within the fair value hierarchy. We did not have any assets and liabilities measured at fair value on a recurring basis using significant unobservable inputs during the three and six months ended November 30, 2021 and 2020.

Table 12.2: Assets and Liabilities Measured at Fair Value on a Recurring Basis
 November 30, 2021May 31, 2021
(Dollars in thousands)Level 1Level 2TotalLevel 1Level 2Total
Assets:
Equity securities, at fair value$37,505 $— $37,505 $35,102 $— $35,102 
Debt securities trading, at fair value— 588,615 588,615 — 576,175 576,175 
Deferred compensation investments7,595 — 7,595 7,222 — 7,222 
Derivative assets— 78,610 78,610 — 121,259 121,259 
Liabilities:
Derivative liabilities$— $615,097 $615,097 $— $584,989 $584,989