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Condensed Consolidated Statements of Cash Flows (Unaudited) - USD ($)
$ in Thousands
6 Months Ended
Nov. 30, 2019
Nov. 30, 2018
Cash flows from operating activities:    
Net income (loss) $ (82,479) $ 167,704
Adjustments to reconcile net income to net cash provided by operating activities:    
Amortization of deferred loan fees (4,704) (5,201)
Amortization of debt issuance costs and deferred charges 4,677 5,596
Amortization of discount on long-term debt 5,304 5,416
Amortization of issuance costs for bank revolving lines of credit 3,034 2,813
Depreciation and amortization 4,755 4,346
Benefit for loan losses (1,015) (1,897)
Loss on early extinguishment of debt 614 7,100
Gain on sale of land (7,713) 0
Unrealized (gains) losses on equity securities (1,506) 2,345
Derivative forward value (gains) losses 187,082 (95,160)
Changes in operating assets and liabilities:    
Accrued interest receivable 2,655 (6,547)
Accrued interest payable (10,122) (2,645)
Deferred income 1,013 796
Other (4,041) (16,466)
Net cash provided by operating activities 97,554 68,200
Cash flows from investing activities:    
Advances on loans, net (521,215) (115,459)
Investment in fixed assets (6,217) (7,403)
Proceeds from sale of land 21,268 0
Net proceeds from time deposits 0 100,000
Proceeds from redemption of equity securities 25,000 0
Purchases of held-to-maturity debt securities (51,386) (52,845)
Proceeds from maturities of held-to-maturity debt securities 43,250 15,354
Net cash used in investing activities (489,300) (60,353)
Cash flows from financing activities:    
Proceeds from short-term borrowings, net 1,129,496 341,562
Proceeds from short-term borrowings with original maturity greater than 90 days 1,266,609 629,350
Repayments of short term-debt with original maturity greater than 90 days (1,214,807) (666,216)
Payments for issuance costs for revolving bank lines of credit (976) (2,342)
Proceeds from issuance of long-term debt, net of discount and issuance costs 160,595 1,362,714
Payments for retirement of long-term debt (946,828) (1,611,437)
Payments made for early extinguishment of debt (614) (7,100)
Payments for issuance costs for subordinated deferrable debt (84) 0
Proceeds from issuance of members’ subordinated certificates 1,427 964
Payments for retirement of members’ subordinated certificates (3,504) (4,279)
Payments for retirement of patronage capital (61,102) (46,953)
Additions (repayments) for membership fees, net 1 (2)
Net cash provided by (used in) financing activities 330,213 (3,739)
Net increase (decrease) in cash, cash equivalents and restricted cash (61,533) 4,108
Beginning cash, cash equivalents and restricted cash 186,204 238,824
Ending cash, cash equivalents and restricted cash 124,671 242,932
Supplemental disclosure of cash flow information:    
Cash paid for interest 415,069 405,249
Cash paid for income taxes $ 18 $ 30