Worthlessness, Debt-Equity, and Related Problems William Natbony
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Hastings Law Journal Volume 32 | Issue 6 Article 1 1-1981 Worthlessness, Debt-Equity, and Related Problems William Natbony Follow this and additional works at: https://repository.uchastings.edu/hastings_law_journal Part of the Law Commons Recommended Citation William Natbony, Worthlessness, Debt-Equity, and Related Problems, 32 Hastings L.J. 1404 (1981). Available at: https://repository.uchastings.edu/hastings_law_journal/vol32/iss6/1 This Article is brought to you for free and open access by the Law Journals at UC Hastings Scholarship Repository. It has been accepted for inclusion in Hastings Law Journal by an authorized editor of UC Hastings Scholarship Repository. THE HASTINGS LAW JOURNAL [Vol. 32 Worthlessness, Debt-Equity, and Related Problems Table of Contents I. Statutory Overview: Worthless Securities and Bad Debts .............. 1409 A. Allowance ........................................... 1409 B. Characterization ................ ....................... 1414 C. Securities and Debts: Differences and Similarities ................ 1420 II. Ascertaining W orthlessness ........................................... 1422 A. Burdens of Proof ..................................... ........ 1426 1. Preliminary Burdens ..................................... 1428 2. Insolvency ...................................... ........ 1431 B. Identifiable Event ............................................. 1435 1. Bankruptcy and Receivership .............................. 1437 2. Reorganization and Foreclosure ............................ 1438 3. Revocation of Corporate Charter .......................... 1440 4. Continuation versus Cessation of Business, Liquidation, and Sale of Assets ............................................ 1441 5. Absence of a Market for Stock ............................ 1444 6. "Identifiable Events" ..................................... 1445 C. Irrevocable Insolvency-The Exceptional Case ................... 1446 1. Going Concern Value ..................................... 1448 D. Subsequent Events .......................................... 1449 E. Inconsistent Actions ........................................... 1449 III. Judicial and Regulatory Distinctions Between Debt and Equity .......... 1452 A. Distinctions Between Debt and Equity ......................... 1454 B. Section 385 ........................................... ....... 1455 C. Scope of the Section 385 Regulations ............................ 1459 D. The Judicial Approach ......................................... 1462 1. Factors of Hindsight-Form ............................... 1463 2. Factors of Hindsight-Intent ............................. 1466 3. Factors of Hindsight-Economic Factors ................... 1470 4. Factors of Foresight-Midstream Transformations ........... 1472 5. Factors of Foresight-Failure to Enforce on Default ......... 1475 6. Factors of Foresight-Advances Continuing After Insolvency.. 1477 7. Factors of Foresight-Accrual of Interest After Insolvency .... 1480 8. Effect of Equity Characterization ......................... 1483 E. Section 385 Regulations-Post December 31, 1981 Interests ....... 1486 1. Fair M arket Value ........................................ 1490 2. Reasonable Rate of Interest .............................. 1492 3. Non-Shareholder Instruments .............................. 1494 a. Hybrid Instruments ................................ 1495 4. Shareholder Obligations .................................. 1499 a. Bifurcation Rules ................................... 1499 b. "Safe Harbor" ..... ................................ 1503 6. Definitions ...................................... ........ 1504 a. Proportionality .................................... 1506 July 1981] DEDICATION 1405 7. Proportional Equity Factors ............................... 1512 a. Hybrid Instruments ................................. 1512 b. Instruments not Issued for Money .................... 1513 c. Excessive Debt ..................................... 1515 d. Change In Terms ................................... 1516 e. Payment History .................................... 1516 f. Instruments Payable on Demand ..................... 1517 8. Shareholder Obligations Not Evidenced by an Instrument .... 1518 9. Preferred Stock .......................................... 1521 F. Comments, Criticisms, and Comparisons ......................... 1523 1. Guaranteed Loans ........................................ 1525 2. Advances Continuing After Insolvency ...................... 1526 3. Accrual of Interest After Insolvency ........................ 1527 4. Reform .................................................. 1527 IV. Related Issues ....................................................... 1528 A. An Introduction to Consolidated Return Requirements Relating to W orthlessness ................................................. 1528 B. Administrative Requirements ................................... 1530 V. Conclusion .......................................................... 1532 Worthlessness, Debt-Equity, and Related Problems By WILLMm NATBONY*t It is a maxim of business that an investment is never made with the expectation of loss; few investments are made with even a suspicion that less than the original outlay will be returned. This perhaps explains the frequency of tax litigation on the issue of loss allowance: with little belief in downside risk, many investors are unprepared to document the context of a loss, having eschewed the legal counseling necessary to plan properly for all contingencies. Financial disaster thus often leaves investors unable to establish a current loss deduction. Recognizing that capital formation and economic growth re- quire speculation, Congress enacted tax provisions to mitigate in- vestor loss.1 The provisions relevant to this discussion concern two investment loss categories: securities2 and debts.3 Preferential treatment is accorded losses of either kind sustained in a business context, especially in the area of intercorporate investment, in which the stakes often are highest.' * J.D., 1975, New York University School of Law; L.L.M., 1976, New York University School of Law. t This paper was prepared while the author was on the faculty of St. Louis University School of Law. The author extends his grateful appreciation to his friend and colleague, Sandy Sarasohn, for his continuous support and guidance, and to Kim Sindel for her valua- ble assistance in the preparation of this Article. Copyright 0 1981, William Natbony. All rights reserved. 1. See Wall Street Journal, June 15, 1979, at 40, col 1 (discussing the 1978 Revenue Act's effect on venture capital). 2. I.R.C. § 165. All references and citations to sections in this Article are to sections of the Internal Revenue Code of 1954, as amended to the date of publication, unless otherwise indicated. All references and citations to regulations are to Treasury Regulations under the Internal Revenue Code of 1954, as amended to the date of publication, unless otherwise indicated. 3. Id. § 166. 4. See Dm. OF COMERCE, U.S. BuREAu OF THE CENsus, STATISTIcAL ABSTRACT OF THE UNrrED STATES § 18 (1979). [1407] THE HASTINGS LAW JOURNAL [Vol. 32 Generally, a loss deduction is allowed when "sustained." 5 Most often a loss is sustained when the loss property is sold or is other- wise disposed of.6 When there is no sale or other disposition of stock or indebtedness, however, planning and ascertaining the tim- ing of a loss deduction is more complex, with the stakes higher and the tax benefits more significant. Deductibility hinges on whether the stock or debt in issue is "worthless," a factual determination turning on administrative and judicial reaction to corroborative facts and to the degree of insolvency. An awareness of the judicial yardsticks for determining worthlessness is essential to defining the issues and to planning for the deduction. Even an allowable deduction for worthlessness may not be beneficial, however, if characterized unfavorably.7 An allowable loss is either capital or ordinary.8 Ordinary losses are fully deducti- ble by both individuals and corporations.9 Corporate capital losses, on the other hand, are deductible only against capital gains. 10 As corporate taxpayers rarely engage in capital gain transactions,"" 12 corporate capital losses are often useless. Loss deductions are also affected by events occurring after the apparent date of worthlessness. A seemingly allowable loss, deduct- ible against ordinary income, may be dissipated by subsequent conduct that is either inconsistent with worthlessness or counter- productive to peripheral tax benefits. Awareness of and attention to postworthlessness conduct is thus fundamental to planning the loss deduction. Moreover, the tax distinctions between debt and equity play an important role in that they may affect both the timing and the allowability of a worthlessness deduction. A debt obligation recharacterized as an equity interest may lose priority and become worthless at a date earlier than that expected by the taxpayer, thus possibly allowing the statute of limitations on deductibility to run. On the other hand, junior debt that is treated as debt for tax pur- 5. I.R.C. § 165(a). See notes 15-18, 32-43 & accompanying text infra. 6. See Treas. Reg. § 1.165-1(d). 7. See notes 69-76 & accompanying text infra. 8. See I.R.C. §§ 65, 1222(2), (4). 9. See id. §§ 65, 1222. See also id. § 1231. 10. Id. § 1211(a). Individuals' capital losses may be deducted only to the extent al- lowed by I.R.C. § 1211(b). 11. But see id. § 1231.