Dwight E. Lee and Leslie E. Lee v. Commissioner of Internal Revenue

155 F.3d 584, 82 A.F.T.R.2d (RIA) 6110, 1998 U.S. App. LEXIS 21624, 1998 WL 640281
CourtCourt of Appeals for the Second Circuit
DecidedAugust 25, 1998
Docket97-4308
StatusPublished
Cited by25 cases

This text of 155 F.3d 584 (Dwight E. Lee and Leslie E. Lee v. Commissioner of Internal Revenue) is published on Counsel Stack Legal Research, covering Court of Appeals for the Second Circuit primary law. Counsel Stack provides free access to over 12 million legal documents including statutes, case law, regulations, and constitutions.

Bluebook
Dwight E. Lee and Leslie E. Lee v. Commissioner of Internal Revenue, 155 F.3d 584, 82 A.F.T.R.2d (RIA) 6110, 1998 U.S. App. LEXIS 21624, 1998 WL 640281 (2d Cir. 1998).

Opinion

CALABRESI, Circuit Judge:

Petitioners claim that their payment of certain interest expenses entitles them to income tax deductions. The United States Tax Court (Howard A. Dawson, Jr., J.) disallowed the deductions and sustained the Commissioner’s claim of a deficiency in petitioners’ tax payments. We affirm the decision of the Tax Court as to the issues that were before it. We remand the case to the Tax Court for the limited purpose of altering the amount of the petitioners’ deficiency, as agreed to by the Commissioner.

BACKGROUND

The deductions at issue in this case arise out of an illegitimate tax shelter that has been the subject of previous tax litigation. See Seykota v. Commissioner, T.C. Memo. 1991-234, 61 T.C.M. (CCH) 2706, 1991 WL 86320, supplemented by T.C. Memo. 1991-541, 62 T.C.M. (CCH) 1116, 1991 WL 218596 (1991). The parties agree that the transactions giving rise to the current litigation are factually the same as those in Seykota. In brief, the substance of those transactions is as follows:

An “investor” seeking to participate in the tax shelter would borrow a sum of money and use it to buy gold. He would simultaneously enter into a futures contract to sell the gold at a specified later time for a slightly higher price. The price difference was to reflect the costs to the investor of acquiring and holding the gold, including the costs of storage, insurance, and, most importantly, interest on the initial loan. Thus, in real terms, the contract tried to guarantee that the investor would recoup exactly what he paid for the gold, neither more nor less. In the year that the investor borrowed the money, he would deduct the cost of interest and the other “carrying charges.” Those deductions were used to offset ordinary income from other sources. Later, when he sold the gold, the investor would report his profit as a capital gain. Between the deferral of income afforded by the deductions for interest and the lower rates of taxation applicable to capital gains, the investor could thus convert tax liabilities at rates of up to 70% payable in a given year to tax liabilities at rates as low as 28% payable in some later year.

The shelter was operated by an entity called Futures Trading, Inc. (“FTI”). Petitioner Dwight Lee was a partner in a group called Peng Partners, which participated in FTI’s shelter. The issue before us is whether that participation entitles petitioners to *586 the investment interest expense deductions they claimed.

DISCUSSION

Petitioners’ interest expenses derive from economically empty transactions for which interest expense deductions are not allowed. See Knetsch v. United States, 364 U.S. 361, 81 S.Ct. 132, 5 L.Ed.2d 128 (1960) (disallowing interest deductions where borrower/ “investor” had no prospect of realizing anything of substance other than tax benefits). Interest payments are not deductible if they arise from transactions “that can not with reason be said to have purpose, substance, or utility apart from their anticipated tax consequences.” Goldstein v. Commissioner, 364 F.2d 734, 740 (2d Cir.1966). Such transactions are said to lack “economic substance.” Jacobson v. Commissioner, 915 F.2d 832, 837 (2d Cir.1990).

“In determining whether an activity is engaged in for profit, greater weight is given to objective facts than to the taxpayer’s mere statement of intent.” 26 C.F.R. § l.lSS-^a). 1 See also Jacobson, 915 F.2d at 838 (applying objective test as specified in § 1.183-2(a)). Looking at the objective facts of FTI’s shelter, the Tax Court determined that petitioners before us entered into these transactions solely for the purpose of claiming the tax deductions engendered. The Tax Court therefore found that the transactions lacked economic substance.

Whether a transaction lacks economic substance is a question of fact. Accordingly, we review the Tax Court’s finding on that question for clear error. Jacobson, 915 F.2d at 837. And we find no such error. Petitioners had arranged, by futures contract, to sell their gold at a price which precluded any significant profit or loss on the underlying investment. Under the principles of Jacobson, Goldstein, and Knetsch, the Tax Court was correct to hold that the transactions were economically empty.

Petitioners argue, however, that a recent development in the law of this circuit justifies the deductions they took. They rely on our statement, toward the end of the opinion in Jacobson, that “Even if the motive for a transaction is to avoid taxes, interest incurred therein may still be deductible if it relates to economically substantive indebtedness.” Jacobson, 915 F.2d at 840. Understood in its traditional way, that statement simply reiterates the undoubted proposition that interest on loans incurred to support an economically substantive investment is not disqualified as a deduction merely because the borrower is also motivated by favorable tax consequences. Petitioners, however, emphasize the word indebtedness and would have us read the statement to mean that interest arising even from economically empty transactions can still be deducted so long as the debt itself has economic substance. They argue that a deduction is permitted unless the debt is a sham or is a nonrecourse obligation from which the taxpayer can walk away with impunity. They contend, in other words, that whenever there is an actual financial liability, the debt instrument itself has sufficient economic reality to support the deductibility of interest expenses. As it is not disputed that petitioners were liable to repay the amount of their loan, such a reading would indeed make their interest expenses deductible.

The strongest support for petitioner’s view comes from the Fourth Circuit’s opinion in Rice’s Toyota World, Inc., v. Commissioner, 752 F.2d 89 (4th Cir.1985). Rice’s Toyota involved a tax-motivated sale and leaseback of more than a million dollars in computer equipment. The Fourth Circuit found that the transaction had no economic substance— apart from expected tax benefits — and disallowed most of the claimed deductions. Id. at 91-92. It also found, however, that one recourse note involved in the transaction was.a genuine debt with economic substance and held the interest on that particular note to be deductible. Id. at 96.

Rice’s Toyota was cited by Jacobson for the well-established proposition that the presence of a tax-related motive for a transaction does not prevent interest expenses arising from that transaction from being deductible, so long as the debt is “economically substantive.” Jacobson, 915 F.2d at 840.

Free access — add to your briefcase to read the full text and ask questions with AI

Related

United States v. Parse
789 F.3d 83 (Second Circuit, 2015)
Shasta Strategic Investment Fund LLC v. United States
76 F. Supp. 3d 895 (N.D. California, 2014)
Bank of N.Y. Mellon Corp. v. Comm'r
2013 T.C. Memo. 225 (U.S. Tax Court, 2013)
United States v. Coplan
703 F.3d 46 (Second Circuit, 2012)
United States v. Daugerdas
759 F. Supp. 2d 461 (S.D. New York, 2010)
Altria Group, Inc. v. United States
694 F. Supp. 2d 259 (S.D. New York, 2010)
Santa Monica Pictures, L.L.C. v. Comm'r
2005 T.C. Memo. 104 (U.S. Tax Court, 2005)
Tifd Iii-E Inc. v. United States
342 F. Supp. 2d 94 (D. Connecticut, 2004)
Long Term Capital Holdings v. United States
330 F. Supp. 2d 122 (D. Connecticut, 2004)
Nicole Rose Corp. v. Commissioner
52 F. App'x 545 (Second Circuit, 2002)
Syms Corp. v. Commissioner of Revenue
765 N.E.2d 758 (Massachusetts Supreme Judicial Court, 2002)
Larry L. Sather v. CIR
251 F.3d 1168 (Eighth Circuit, 2001)
Winn-Dixie Stores v. Comm'r
113 T.C. No. 21 (U.S. Tax Court, 1999)
Winn-Dixie Stores, Inc. and Subsidiaries v. Commissioner
113 T.C. No. 21 (U.S. Tax Court, 1999)
UPS v. Comm'r
1999 T.C. Memo. 268 (U.S. Tax Court, 1999)
Leema Enters., Inc. v. Commissioner
1999 T.C. Memo. 18 (U.S. Tax Court, 1999)

Cite This Page — Counsel Stack

Bluebook (online)
155 F.3d 584, 82 A.F.T.R.2d (RIA) 6110, 1998 U.S. App. LEXIS 21624, 1998 WL 640281, Counsel Stack Legal Research, https://law.counselstack.com/opinion/dwight-e-lee-and-leslie-e-lee-v-commissioner-of-internal-revenue-ca2-1998.