rr-02-69.pdf

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Part I

Section 162.CTrade or Business Expenses

26 CFR 1.162-11: Rentals.
(Also ' 163; 1.163-1.)

Rev. Rul. 2002-69

ISSUE
May a taxpayer deduct currently, under ''162 and 163 of the Internal
Revenue Code, rent and interest paid or incurred in connection with a Alease-
in/lease-out@ (ALILO@) transaction?
FACTS
X is a U.S. corporation. FM is a foreign municipality that has historically
owned and used certain property. As of 1997, it is estimated that the property
has a remaining useful life of 50 years and a fair market value of $100 million.
BK1 and BK2 are banks. None of these four parties is related to any of the
others.
On January 1, 1997, X and FM entered into a LILO transaction under
which FM leased the property to X under a "Headlease," and X immediately
leased the property back to FM under a "Sublease." The term of the Headlease
is 40 years. The primary term of the Sublease is 20 years. Moreover, as
described below, the Sublease also may be renewed for a term of 10 years (Aput
renewal term@) at the option of X. X=s right to possess the property under the

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Headlease for the first 20 years is substantially the same as FM=s right to
possession under the Sublease for the primary term. The Headlease
requires X to make two rental payments to FM during its 40-year term: (1) an $89
million prepayment at the beginning of year 1; and (2) a postpayment at the end
of year 40 that has a discounted present value of $8 million. For federal income
tax purposes, X and FM allocate the prepayment ratably to the first 6 years of the
Headlease and the future value of the postpayment ratably to the remaining 34
years of the Headlease.
The Sublease requires FM to make fixed, annual rental payments over
both the primary term and, if exercised, the put renewal term. The fixed, annual
payments during the put renewal term are equal to 90 percent of the amounts
that (as of January 1, 1997) are projected to be the fair market value rental
amounts for that term.
To partially fund the $89 million Headlease prepayment, X borrows $54
million from BK1 and $6 million from BK2. Both loans are nonrecourse, have
fixed interest rates, and provide for annual debt service payments that fully
amortize the loans over the 20-year primary term of the Sublease. The amount
and timing of the debt service payments mirror the amount and timing of the
Sublease payments due during the primary term of the Sublease. The remaining
$29 million of the Headlease prepayment is provided by X.
Upon receiving the $89 million Headlease prepayment, FM deposits $54
million into a deposit account with an affiliate of BK1 and $6 million into a deposit
account with an affiliate of BK2. The deposits with the affiliates of BK1 and BK2
earn interest at the same rates as the loans from BK1 and BK2. FM directs the

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affiliate of BK1 to pay BK1 annual amounts equal to 90 percent of FM's annual
rent obligation under the Sublease (that is, amounts sufficient to satisfy X's debt
service obligation to BK1). The parties treat these amounts as having been paid
from the affiliate to FM, then from FM to X as rental payments, and finally from X
to BK1 as debt service payments. In addition, FM pledges the deposit account
to X as security for FM's obligations under the Sublease, while X, in turn, pledges
its interest in FM's pledge to BK1 as security for X's obligations under the loan
from BK1. Similarly, FM directs the affiliate of BK2 to pay BK2 annual amounts
equal to 10 percent of FM's annual rent obligation under the Sublease (that is,
amounts sufficient to satisfy X's debt service obligation to BK2). The parties
treat these amounts as having been paid from the affiliate to FM, then from FM
to X as rental payments, and finally from X to BK2 as debt service payments.
Although FM
=s deposit with the BK2 affiliate is not pledged, the parties
understand that FM will use the account to pay the remaining 10 percent of FM's
annual rent obligation under the Sublease.
As a result of the foregoing arrangement, X=s obligation to make the
property available under the 20-year primary term of the Sublease is completely
offset by X=s right to use the property under the Headlease. X=s obligation to
make debt service payments on the loans from BK1 and BK2 is completely offset
by X=s right to receive Sublease rentals from FM. Moreover, X=s exposure to the
risk that FM will not make the rent payments is further limited by the
arrangements with the affiliates of BK1 and BK2. In the case of the loan from
BK1, X=s economic risk is eliminated through the defeasance arrangement. In
the case of the $6 million loan from BK2, X=s economic risk, although not

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eliminated, is substantially reduced through the deposit arrangement. As a
result, neither bank requires an independent source of funds to make the loans,
or bears significant risk of nonpayment. In short, during the primary Sublease
term, the transaction is characterized by reciprocal and circular obligations that
offset one another.
At the end of the Sublease primary term, FM has a fixed-payment option
to purchase from X the Headlease residual (the right to use the property beyond
the Sublease primary term subject to the obligation to make the rent
postpayment) for a fixed exercise price equal to 105 percent of the amount that
(as of January 1, 1997) is projected to be the future fair market value of the
Headlease residual. If FM exercises the option, the transaction is terminated at
that point, and X receives the exercise price of the option and is not required to
make any portion of the postpayment due under the Headlease. If FM does not
exercise the option, X may elect to (1) use the property itself for the remaining
term of the Headlease, (2) lease the property to another person for the remaining
term of the Headlease, or (3) compel FM to lease the property for the 10-year
put renewal term of the Sublease. If FM does not exercise the fixed-payment
option and X exercises its put renewal option, X will receive rents that are equal
to 90 percent of the amounts that are (as of January 1, 1997) projected to be the
fair market rents for that term. If the actual fair market rents in 20 years turn out
to be less than the amount specified in the put renewal option and FM does not
exercise the fixed-payment option, X will be able to compel FM to lease the
property for rents that are greater than the then fair market rental value. Thus,

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as a practical matter, the fixed-payment option and put renewal option operate to
Acollar@ the value of the Headlease residual during the primary term.
In addition, X has nominal exposure to FM=s credit under the fixed-
payment option and, if exercised, the put renewal term. At the inception of the
transaction, X requires FM to invest $15 million of the Headlease prepayment in
highly-rated debt securities that will mature in an amount sufficient to fund the
fixed amount due under the fixed-payment option, and to pledge these debt
securities to X. This arrangement ensures that FM is able to make the payment
under the fixed-payment option. Having economically defeased both its rental
obligations under the Sublease and its fixed-payment under the fixed-payment
option, FM keeps the remaining portion of the Headlease prepayment as its
return on the transaction. If FM does not exercise the fixed-payment option and
X exercises the put renewal option, X can require FM to purchase a letter of
credit guaranteeing the put renewal rents. If FM does not obtain the letter of
credit, FM must exercise the fixed-payment option.
For tax purposes, X claims deductions for interest on the loans and for the
allocated rents on the Headlease. X includes in gross income the rents received
on the Sublease. If the fixed-payment option is exercised, X also includes the
option price and recaptures rent deductions taken during the primary Sublease
term that are attributable to the postpayment it is no longer required to make.
LAW AND ANALYSIS
X and FM=s allocations of the prepayment and the postpayment for federal
income tax purposes meet the uneven rent test contained in proposed ' 467
regulations (' 1.467-3(c)(2)(i)), and under those regulations the Headlease would

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not be treated as a disqualified leaseback or long-term agreement subject to
constant rental accrual. Because this LILO transaction was entered into after
June 3, 1996, and on or before May 18, 1999, the provisions of the proposed
regulations are available. See ' 1.467-9(c). For later years, however, final ' 467
regulations effective May 18, 1999, treat the prepayment of rent as resulting in a
deemed loan from X to FM and require the imputation of interest income to X. '
1.467-4. Moreover, X=s rent deduction would be subject to proportional rent
rules that reflect the time value of money concept. See ' 1.467-2(c).
The substance of a transaction, not its form, governs its tax treatment.
Gregory v. Helvering, 293 U.S. 465 (1935). In Frank Lyon Co. v. United States,
435 U.S. 561, 573 (1978), the United States Supreme Court stated, AIn applying
the doctrine of substance over form, the Court has looked to the objective
economic realities of a transaction rather than to the particular form the parties
employed.@ The Court evaluated the substance of the transaction in Frank Lyon
to determine that it was indeed a sale/leaseback, as it was structured, rather
than a financing. The Court subsequently relied on its approach in Frank Lyon to
recharacterize a sale and repurchase of federal securities as a loan, finding that
the economic realities of the transaction did not support the form chosen by the
taxpayer. Nebraska Dep
=t of Revenue v. Loewenstein, 513 U.S. 123 (1994).
Where parties have in form entered into two separate transactions that
result in offsetting obligations, the courts often have collapsed the offsetting
obligations and recharacterized the two transactions as a single transaction. In
Rogers v. United States, 281 F.3d 1108 (10
th
Cir. 2002), the part-owner
(Fogelman) of a professional baseball team that was organized as an S

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corporation borrowed money from the S corporation. The nonrecourse loan was
secured by Fogelman=s ownership interest in the corporation and his existing
option to purchase the rest of the shares from the taxpayer (Kauffman), the other
owner of the team. Fogelman also granted the corporation an option to
purchase both his shares and his existing option to buy Kauffman=s shares. The
option price was an amount equal to the outstanding loan balance. The
corporation exercised its option immediately but deferred closing until the due
date of Fogelman=s loan, five months later. On that date, Fogelman transferred
his shares in the corporation to the corporation in lieu of its foreclosure on the
loan. The corporation claimed that the shares had no value at that time and
deducted the loan amount as a bad debt, which was passed through to
Kauffman.
The court in Rogers applied the substance over form doctrine to collapse
the loan and the option transaction into a redemption of Fogelman=s stock in
exchange for cash. Fogelman had no incentive to repay the loan because any
reduction in the loan balance would reduce the option price. The immediate
exercise of the option precluded any attempt by Fogelman to repay the loan and
keep the stock. On the basis of those facts, among others, the court held that
the substance of the transaction was a sale of Fogelman=s stock to the
corporation.
In Bussing v. Commissioner, 88 T.C. 449, reconsideration denied, 89 T.C.
1050 (1987), a Swiss subsidiary of a computer leasing company (AG) purchased
computer equipment in a sale/leaseback transaction involving a five-year lease.
Subsequently, AG purportedly sold the equipment to a domestic corporation

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(Sutton), which in turn purportedly sold interests in the equipment to the taxpayer
(Bussing) and four other individual investors. Bussing acquired his interest in the
computer equipment subject to the underlying lease by paying cash, short-term
promissory notes, and a long-term promissory note to Sutton. Bussing then
leased his interest in the equipment back to AG for nine years. The rents due
Bussing from AG equaled Bussing=s annual payments on the long-term
promissory note to Sutton for the first three years and were supposed to
generate nominal annual cash flow thereafter.
The court first disregarded Sutton=s participation in the transactions on
substance over form grounds. It then held that Bussing=s long-term
indebtedness also must be disregarded because it was completely offset by
AG=s rent payments in a Apurported sale-leaseback pursuant to which the
respective lease and debt obligations flow between only two parties.@ Id. at 458.
The court stated,
The respective obligations between AG and Bussing cancel each
other out. Any possible claim by AG with respect to the note is fully
offset by AG=s rental obligation to Bussing. . . . Bussing, effectively,
will never be required to make any payments on his debt obligation,
a feature of the transaction that we believe the parties intended to
achieve.

Id. After collapsing the offsetting loan and lease, the court concluded that
Bussing had acquired an interest in a joint venture with AG and the other
investors to the extent of his cash payment only.
Courts have similarly disregarded the parties= obligations in purported
installment sales where the taxpayer received an installment note that was offset
by some other arrangement between the two parties, indicating that the maker of

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the note would not be called upon to pay the installment obligation. See Rickey
v. Commissioner, 502 F.2d 748 (9
th
Cir. 1974), aff=g 54 T.C. 680 (1970).
Although taxpayers are entitled to arrange the terms of a sale in order to qualify
for the installment method, Athe arrangements must have substance and must
reflect the true situation rather than being merely the formal documentation of
the terms of the sale.@ Id. at 752-53, quoting 54 T.C. 680 at 694. See also
United States v. Ingalls, 399 F.2d 143 (5
th
Cir. 1968); Blue Flame Gas Co. v.
Commissioner, 54 T.C. 584 (1970); Greenfield v. Commissioner, T.C. Memo.
1982-617; Big "D" Development Corp. v. Commissioner, T.C. Memo. 1971-148,
aff=d per curiam, 453 F. 2d 1365 (5
th
Cir.1972).
Similarly, the Headlease and Sublease impose offsetting obligations that
must be disregarded, regardless of whether other components of the LILO
transaction are respected. During the first 20 years of its term, the Headlease
confers to X a right to use the property that is immediately reversed by the
Sublease grant to FM of substantially the same right to use property. In the LILO
transaction, the Sublease interest retained by FM is of the same nature as the
Headlease interest conveyed to X. Because the transfer and retransfer of the
right to possess the property for the first 20 years are disregarded as offsetting
obligations, the transaction that remains is, at best, a transfer of funds from X to
FM in exchange for FM=s obligation to repay those funds and provide X the right
to begin to lease the property in 20 years.
An analogous situation occurs when the conveyance of property is
accompanied by the retention of some interest in the same property. If the
interest retained is of substantially the same nature as the interest conveyed,

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only a future interest is conveyed. In McCully Ashlock v. Commissioner, 18 T.C.
405 (1952), acq., 1952-2 C.B. 1, taxpayer had acquired property through a deed
dated June 6, 1945. The seller, however, had retained the right to possession
and rentals through August 15, 1947. The court found that taxpayer had
acquired only a future interest in the property because Athe trustees [sellers] not
only retained the rents legally but they also retained control and benefits of
ownership.@ Id. at 411. Consequently, rentals from the property were income to
the seller.
Similarly, in Kruesel v. United States, 63-2 U.S. Tax Cas. (CCH) & 9714
(D. Minn. 1963), the court concluded that taxpayer had transferred only a future,
remainder interest in property and reserved a life estate. The government had
unsuccessfully argued that taxpayer had sold its entire interest in the property
and the taxpayer=s amount realized on the sale included the value of a right to
occupancy provided to the taxpayer by the buyer.
In contrast, in Alstores Realty Corp. v. Commissioner, 46 T.C. 363 (1966),
acq., 1967-2 C.B.1, the court held that a sale of property accompanied by the
reservation of a right of occupancy did not result in the transfer of only a future
interest because the seller=s right of occupancy was in the nature of a leasehold
interest, because the purchaser acquired the benefits and burdens of ownership
of the property.
Alstores can be distinguished from McCully Ashlock and Kruesel. McCully
Ashlock and Kruesel conclude that where a retained interest is of the same
nature as the interest conveyed, only a future interest has been transferred. In
Alstores, the interests were not of the same nature.

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Similarly, the LILO transaction is distinguishable from the transaction
involved in Comdisco, Inc. v. Commissioner, 756 F.2d 569 (7
th
Cir. 1985). In that
case, equipment was subject to end user leases, and the lessor of that
equipment assigned an interest to taxpayer in a transaction designed to give the
taxpayer investment tax credits. The taxpayer=s entitlement to the credits
depended on whether it had the status of lessee/sublessor. In concluding that it
did, the court noted a number of factors that supported taxpayer=s claim that it
had acquired a leasehold interest. The taxpayer was obligated to the lessor in
the event of a default by the sublessee. The taxpayer relet certain equipment
after one sublease had expired. In connection with another sublease, the
taxpayer was responsible for rent to its assignor in excess of amounts paid by
the sublessee directly to the assignor. The court also emphasized the regulatory
restrictions on direct leases between the assignor and the end users. Id. at 576-
77. Unlike Comdisco, in the LILO transaction the headlessor and the sublessee
are the same party. Further, in the LILO transaction the headlessee/sublessor is
not materially exposed to the risk that the sublessee will fail to make rent
payments.
Section 162(a)(3) permits a deduction for rentals and other payments
required to be made as a condition to the continued use or possession, for
purposes of the trade or business, of property. Because X does not acquire a
current leasehold interest in the property, it is not entitled to current deductions
for rent. The $29 million Aequity@ portion of the Headlease prepayment is,
effectively, a payment for at most X=s right under the Headlease to lease the
property 20 years hence for a term of 20 years. (Economically, $29 million is an

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overpayment for the value of any right that X obtains to lease the property in the
future. X was willing to overpay in this manner, however, in order to induce FM
to participate in the transaction.). In accordance with ' 467, the $29 million
Aequity@ portion of the Headlease prepayment is deductible over the 20-year
residual term of the Headlease (the 10-year put renewal term and the 10-year
Ashirttail@ period). Alternatively, in the event FM exercises its fixed-price option at
the end of the primary term of the Sublease, X will have gain or loss equal to the
difference between the option price and X=s cost of acquiring a right to the
Headlease residual term. Section 1001.
The remainder of the Headlease prepayment, $60 million, must be
disregarded, because the "loans" that purportedly finance this portion of the
Headlease prepayment are without substance. In Bridges v. Commissioner, 39
T.C. 1064, aff
=d 325 F.2d 180 (4
th
Cir. 1963), taxpayer "borrowed" funds from
banks and used the funds to purchase Treasury notes, which the banks held as
collateral and ultimately sold to satisfy taxpayer=s debts. The court=s rationale for
disallowing taxpayer=s deductions of prepaid interest is equally applicable here:
[P]etitioner at no time had the uncontrolled use of any additional money,
of the bonds, or of the interest on the bonds. He assumed no risk of a rise
or fall in the market price of the bonds and could not take advantage of
such. His payment to the bank was not for the use or forbearance of
money; it was for the purchase of a rigged sales price for the bonds and
for a tax deduction. Petitioner incurred no genuine indebtedness, within
the meaning of the statute, and as a payment of interest, this transaction
was also a sham.
Id. at 1078-79. Neither X nor FM obtain use of the "borrowed" funds. The
"loans" purportedly are made to finance X=s acquisition of the Headlease
interest. But that leasehold interest is substantially offset by an interdependent
Sublease with the Headlessor. What remains can only be enjoyed after 20 years

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and after the loans have been "repaid" using "rents" from a Sublease that itself
lacks substance. Under the circumstances, the loans are disregarded.
Although this ruling refers to a foreign municipality and its property, the
analysis and holding apply as well to LILO transactions that involve or include
domestic tax-exempt or tax-indifferent entities.
HOLDING
A taxpayer may not deduct currently, under '' 162 and 163, rent or
interest paid or incurred in connection with a LILO transaction that properly is
characterized as conferring only a future interest in property.
Where appropriate, the Service will continue to disallow the tax benefits
claimed in connection with LILO transactions upon other grounds, including that
the substance over form doctrine requires their recharacterization as financing
arrangements and that they are to be disregarded for lack of economic
substance.
EFFECT ON OTHER DOCUMENTS
Rev. Rul. 99-14, 1999-1 C.B. 835, is modified and superseded.
DRAFTING INFORMATION
The principal author of this revenue ruling is John Aramburu of the Office
of Associate Chief Counsel (Income Tax & Accounting). For further information
regarding this revenue ruling contact Mr. Aramburu at (202) 622-4960 (not a toll-
free call).