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Fair Value Measurement (Tables)
 3 Months Ended
Aug. 31, 2023
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 August 31, 2023 and May 31, 2023. 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
 August 31, 2023Fair Value Measurement Level
(Dollars in thousands)Carrying ValueFair ValueLevel 1Level 2Level 3
Assets:    
Cash and cash equivalents$199,552 $199,552 $199,552 $— $— 
Restricted cash9,290 9,290 9,290 — — 
Equity securities, at fair value36,780 36,780 36,780 — — 
Debt securities trading, at fair value425,331 425,331 — 425,331 — 
Deferred compensation investments7,162 7,162 7,162 — — 
Loans to members, net33,041,720 29,309,889 — — 29,309,889 
Accrued interest receivable177,351 177,351 — 177,351 — 
Derivative assets615,866 615,866 — 615,866 — 
Total financial assets$34,513,052 $30,781,221 $252,784 $1,218,548 $29,309,889 
Liabilities:  
Short-term borrowings$5,124,335 $5,125,706 $— $4,625,706 $500,000 
Long-term debt23,874,274 22,148,726 — 13,395,526 8,753,200 
Accrued interest payable274,554 274,554 — 274,554 — 
Guarantee liability13,552 13,088 — — 13,088 
Derivative liabilities108,239 108,239 — 108,239 — 
Subordinated deferrable debt1,184,197 1,172,990 241,771 931,219 — 
Members’ subordinated certificates1,222,026 1,222,026 — — 1,222,026 
Total financial liabilities$31,801,177 $30,065,329 $241,771 $19,335,244 $10,488,314 

 May 31, 2023Fair Value Measurement Level
(Dollars in thousands)Carrying ValueFair ValueLevel 1Level 2Level 3
Assets:    
Cash and cash equivalents$198,936 $198,936 $198,936 $— $— 
Restricted cash8,301 8,301 8,301 — — 
Equity securities, at fair value35,494 35,494 35,494 — — 
Debt securities trading, at fair value474,875 474,875 — 474,875 — 
Deferred compensation investments6,660 6,660 6,660 — — 
Loans to members, net32,478,992 29,308,647 — — 29,308,647 
Accrued interest receivable172,723 172,723 — 172,723 — 
Derivative assets460,762 460,762 — 460,762 — 
Total financial assets$33,836,743 $30,666,398 $249,391 $1,108,360 $29,308,647 
Liabilities:  
Short-term borrowings$4,546,275 $4,547,333 $— $4,547,333 $— 
Long-term debt23,946,548 22,665,551 — 13,527,393 9,138,158 
Accrued interest payable212,340 212,340 — 212,340 — 
Guarantee liability12,973 12,475 — — 12,475 
Derivative liabilities115,074 115,074 — 115,074 — 
Subordinated deferrable debt1,283,436 1,261,141 240,831 1,020,310 — 
Members’ subordinated certificates1,223,126 1,223,126 — — 1,223,126 
Total financial liabilities$31,339,772 $30,037,040 $240,831 $19,422,450 $10,373,759 
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 August 31, 2023 and May 31, 2023, 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 months ended August 31, 2023 and 2022.

Table 12.2: Assets and Liabilities Measured at Fair Value on a Recurring Basis

 August 31, 2023May 31, 2023
(Dollars in thousands)Level 1Level 2TotalLevel 1Level 2Total
Assets:
Equity securities, at fair value$36,780 $— $36,780 $35,494 $— $35,494 
Debt securities trading, at fair value— 425,331 425,331 — 474,875 474,875 
Deferred compensation investments7,162 — 7,162 6,660 — 6,660 
Derivative assets— 615,866 615,866 — 460,762 460,762 
Liabilities:
Derivative liabilities$— $108,239 $108,239 $— $115,074 $115,074