# Long Term Capital Holdings v. United States

> District Court, D. Connecticut · August 27, 2004 · 330 F. Supp. 2d 122

URL: https://www.frixlaw.com/law-library/cases/2314334

## Case

- **Full name:** LONG TERM CAPITAL HOLDINGS, Et. Al., Petitioners v. UNITED STATES of America, Respondent
- **Court:** District Court, D. Connecticut
- **Decided:** August 27, 2004
- **Citations:** 330 F. Supp. 2d 122; 94 A.F.T.R.2d (RIA) 5666; 2004 U.S. Dist. LEXIS 17159; 2004 WL 1924931
- **Precedential status:** Published
- **Opinion:** Opinion by Arterton
- **Judges:** Arterton
- **Cited by:** 50 later opinions in the Frix Law Library

## Citator (automated)

- No negative treatment found by the automated citator. That is not the same as a confirmation that the case is good law; read the citing cases.
- Full citator and citing cases: https://www.frixlaw.com/law-library/cases/2314334

## How later opinions describe it (automated extraction)

- holding that a taxpayer “cannot avoid the requirements of economic substance simply by coupling a routine economic transaction generating substantial profits and with no inherent tax benefits to a unique transaction that otherwise has no hope of turning a profit”
- finding that the transaction lacked economic substance because, “at the time the transaction was entered into, a prudent investor would have concluded that there was no chance to earn a non-tax based profit return in excess of the costs of the transaction”
- finding that transaction lacked economic substance because, “at the time the transaction was entered into, a prudent investor would have concluded that there was no chance to earn a non-tax based profit return in excess of the costs of the transaction”
- stating that tax was opinion based on “unreasonable legal assumption” when no citation to case law of applicable jurisdiction and little analysis of economic substance and step transaction doctrines
- holding that, when underlying merits determination is that transaction lacks economic substance, taxpayer cannot cite authority, much less substantial authority, to support claimed tax treatment

## Opinion text

FINDINGS AND OPINION
ARTERTON, District Judge.
Table of Contents
I. Summary 127
II. Factual Background 128
A. Long Term Entities 128
*126
B. Babcock and Brown (“B & B”) and Onslow Trading and Commercial LLC (“OTC”) .131
C. CHIPS and TRIPS Transactions.132
1. CHIPS IVA and IVB .132
2. TRIPS I .135
3. Purported Tax Consequences of CHIPS IVA and IVB and TRIPS 1.135
D. OTC and Long Term.136
1. OTC/Long Term Transaction .136
2. Long Term/B & B/UBS Transaction.138
3. Long Term’s Tax Returns.139
4. B&B and OTC After CHIPS and TRIPS.139
5. The Origin of a Transaction for Long Term.142
6. Long Term and B&B.143
7. Long Term and Shearman & Sterling.145
8. Long Term and King & Spalding.147
a. Kuller’s Claimed Pre-Tax Expectation of Profit Analysis.149
b. Kuller’s Credibility .151
9. Long Term and OTC.153
a. Communication Among Long Term’s Principals.153
b. Unusual Nature of OTC’s Contributions.155
c. Long Term’s and OTC’s Intent Regarding the OTC Transaction.155
d. Scholes’ November 12,1996 Memorandum.157
10. The Turlington Problem.158
11. Petitioner’s Expert: Frank J. Fabozzi.160
12. Scholes’ Economic Analysis.161
13. Government’s Expert: Joseph Stiglitz.163
14. IRS Audit and Long Term’s Response .165
III. Discussion.165
A. Burden of Proof.165
1. Cooperation with Reasonable Requests.166
2. Net Worth.170
3. Conclusion on Burden of Proof.170
B. Lack of Economic Substance.171
1. Objective Economic Substance.172
2. The Scope of the Transaction for Purposes of Measuring Costs and Reasonable Expectation of Return.174
3. Reasonably Expected Return.175
4. Costs of the OTC Transaction.175
a. Legal Fees .176
b. “Consulting Arrangement” with B&B.177
c. The Turlington Payment.178
d. Scholes’ Allocation and Noe’s Bonus.180
e. Economic Structure of OTC Contributions.181
f. B & B’s Investment Through UBS.183
5. “Things Economic Happened” — Tr. [Doc. #207] at 3228:25-3229:1.185
6. Subjective Business Purpose.186
C. Step Transaction Doctrine .191
D. Penalties.196
1. Burden of Proof.196
2. Gross Valuation Misstatement.199
3. Substantial Understatement of Income Tax.200
a. Substantial Authority.201
b. Reasonable Belief.205
4. Reasonable Cause Exception.205
a. Receipt and Content of King & Spalding Advice.206
b. King & Spalding’s Written Opinion.208
c. Long Term’s Lack of Good Faith.211
IV. Conclusion.212
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Appendix — Timeline of OTC Transactional Events :.212
I. Summary
Petitioners Long-Term Capital Holdings (“Holdings”), Long-Term Capital Management L.P. (“LTCM”), Long-Term Capital Portfolio L.P. (“Portfolio”), Long-Term Capital Fund,
1
Eric Rosenfeld, and Richard Leahy filed petitions under 26 U.S.C. § 6226 (a)(2) seeking (a) readjustment of the IRS denial of $106,058,228 in capital losses for petitioners’ 1997 tax year in connection with the sale by Portfolio on December 30, 1997 of preferred stock for $1,078,400 with a claimed basis of $107,136,628, and (b) a determination that the IRS imposition of penalties pursuant to 26 U.S.C. § 6662 (a), (b)(l-3), (h) was erroneous. Jurisdiction is conferred by 28 U.S.C. § 1346 (e). The Court’s findings of fact and conclusions of law set out in this opinion are based on the bench trial held June 23, 2003 — July 30, 2003.
Petitioners’ claim that Portfolio sold stock on December 30, 1997 with a tax basis one hundred times in excess of its fair market value arises from two separate sets of transactions. The first set is comprised of nine cross border lease-stripping transactions, five of which utilized a master lease or wrap lease structure and were termed “Computer Hardware Investment Portfolio” (“CHIPS”) and four of which utilized a sale/lease back structure and were termed “Trucking Investment Portfolios” (“TRIPS”).
In the CHIPS transactions, Onslow Trading and Commercial LLC (“OTC”), an entity incorporated under the laws of the Turks and Caicos Islands, purportedly leased from General Electric Capital Computer Leasing (“GECCL”) computer equipment already subject to existing leases to end-users and then immediately subleased its rights in the equipment to U.S. based partnerships. The new sublessees then pre-paid 92.5% of the rent due under the subleases. The prepayments, totaling tens of millions of dollars, were made with loans to the U.S.-based partnerships from Barclays Finance & Leasing B.V. (“Bar-clays”) and were guaranteed by GECCL. OTC, formed under foreign laws and resident in the United Kingdom, paid no U.S. taxes upon receipt of the, rent prepayments and deposited them into a Barclays branch bank account. OTC then exchanged the master leases, the subleases and the bank accounts with the prepayment deposits for preferred stock in certain U.S. corporations; OTC received approximately $1,000,000 in preferred stock for every $100,000,000 of prepayments and lease positions it gave up. OTC’s transfer was timed to be prior to accrual of rent under the subleases such that under UK law OTC paid no taxes on the prepayments. Pursuant to 26 U.S.C. §§ 351 , 358, these exchanges were claimed to be tax free exchanges and OTC claimed an ad
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justed basis in the preferred stock tranches it received of approximately $100,000,000.
In the TRIPS transactions, Wal-Mart sold fleets of trucks to NationsBanc and First American National Bank, the banks leased the trucks to OTC, and OTC subleased the trucks back to Wal-Mart. Wal-Mart guaranteed OTC’s obligations to the banks and prepaid a percentage of the rent due under the sublease. In TRIPS I, the prepayment was 92.5% of the rent due, approximately $27 million, which OTC deposited in a bank account. Again, before the sublease rent accrued, OTC exchanged its lease positions and bank deposits for preferred stock of American corporations. The ratio of exchange again approximated $1 of preferred stock received for every $100 of lease positions and prepayment deposits given up.
OTC, in a purported transaction under 26 U.S.C. § 721 , contributed to Long Term the tranches of preferred stock it received from the TRIPS and CHIPS transactions, which had a fair market value of approximately $4 million and a claimed basis of $400 million, in exchange for a Long Term partnership interest. OTC subsequently sold its partnership interest to Long Term and withdrew from the partnership. Long Term then had Portfolio sell a portion of the contributed TRIPS and CHIPS stock to purportedly generate the claimed losses in dispute in this case and those losses were allocated to Long Term under the loss allocation rules of U.S. partnership tax law.
2
For the reasons set forth below, the Court finds that the transaction in which OTC and Long Term engaged lacked economic substance and therefore must be disregarded for tax purposes, and, in the alternative, must be recast under the step transaction doctrine as a sale of preferred stock by OTC to Long Term resulting in an adjustment in Long Term’s basis in the preferred stock to Long Term’s purchase price. With respect to penalties, the Court rejects Long Term’s contention that it satisfied the requirements of the reasonable cause defense to such penalties by obtaining legal opinions, and upholds the IRS application of 40% gross valuation misstatement and 20% substantial understatement penalties related to Long Term’s claim of basis in OTC’s contributed stock. Accordingly, the petitions are DENIED in all respects.
II. Factual Background
A. Long Term Entities
Long Term’s origins can be traced to late 1992 and January 1993, when founding principals John Meriwether, Eric Rosen-feld,
3
James McEntee, and Robert Merton
4
began discussing the prospect of creating a hedge fund
5
to execute strategies
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using leveraged investments keyed to arbitrage opportunities in large bond markets. They used 1993 and early 1994 to raise money, find principals, locate office space, and hire employees. Ultimately, Long Term had twelve founding principals, including Meriwether, Rosenfeld, Merton, and Myron Scholes.
6
In March 1994, Long Term began to manage the investments it had raised. The principals themselves invested more than $100,000,000 in Long Term when the fund began its operations in 1994, and they sought to increase their individual investments throughout Long Term’s active operation, including through loans to LTCM, investment of LTCM’s working capital into Portfolio, and reinvestment of their individual investment profits into Portfolio. During 1994 and 1995, Scholes was giving explanatory presentations about the fund to prospective investors. He also worked closely with Long Term’s counsel in structuring Long Term’s private placement memoranda, which described the legal rights of investors, the objectives of an investment in the fund, and the risks involved with an investment. By 1996, Long Term had grown to 150 employees with twelve managing partners and offices in Greenwich, Connecticut, London, and Tokyo, and was managing five to six billion dollars of equity. Long-Term had a diverse group of investors, most of which were institutional investors, including a number of investment banking firms, but some of which were high net worth individuals. Two-thirds of its investors were located overseas.
Meriwether was the managing partner from March 1994 until at least 1996. As established and advanced by him, the twelve Long Term principals operated on a consensus management model, in which all twelve participated in managerial decisions, no votes were taken, and all had to agree or Long Term did not move forward with a proposed course of action. The principals participated in risk management meetings at least weekly. Meriwether would delegate particular issues or responsibilities to committees or principals who then bore the burden of explaining substantive issues and recommending courses of action. Scholes was the principal primarily in charge of the “OTC” transaction that figures centrally in this case. Larry Noe, hired in early 1996 as Long Term’s in-house tax counsel, worked closely with Scholes on the tax issues related to the OTC transaction.
7
Long Term operated with a three-tiered structure: LTCM was the top tier and
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managed all of the affairs of Long Term generally; Portfolio, the hedge fund, was the bottom tier into which all investments flowed; and in the middle tier were various investment vehicles, including LTCP, a U.S. domestic limited partnership, which served as conduits to pool all investments in Portfolio. Multiple mid-tier investment vehicles were used in large part to avoid complexities arising from laws of different countries by pooling assets from investors from particular countries. Thus, generally, foreign investors did not invest in Portfolio via LTCP but through overseas investment vehicles only. LTCP was the only investment vehicle that was treated as a partnership under U.S. federal income tax laws.
Simpson Thacher Bartlett LLP was regular outside counsel for Portfolio during the 1994 to 1998 time frame, although LTCM utilized a number of different law firms depending on which one it considered best suited for particular problems as they arose. Prior to the OTC-related transactions at issue in this case, Long Term had not used the law firm of Shear-man & Sterling.
Long Term established general investing requirements, including minimum capital investment amounts and time periods, although the principals retained discretion to vary these terms for particular investors. The minimum investment required when Long Term began was $10 million but under certain circumstances Long Term accepted investments smaller than that amount.
See e.g. infra
note 9. Initially, Long Term required new investments to be committed for a three year period but allowed investors to remove their profits generated from the initial investment on a yearly basis. Early on, however, Long Term realized that the three year lock-in would result in a lumpy capital structure if investors elected to remove their capital at the expiration of the three year period, and it adjusted its investing requirements to permit investors to remove a third of invested capital annually. In addition, investors were required to obtain Long Term’s permission to pledge or assign their partnership interest. Taking on new investors was a fairly routine matter that did not typically require substantial outlay of expenses for legal advice or opinions.
LTCM charged fees on all equity capital invested in Portfolio: a two percent annual management fee calculated on a quarterly basis from the equity capital invested in Portfolio; and an incentive or performance fee of twenty-five percent of the gross return of Portfolio in excess of the two percent management fee.
8
In late 1995, Long Term was running out of investment strategies and “closed” Portfolio to new investors, prompted by concern that continued expansion of its equity capital base would compromise its ability to continue to earn the high returns obtained for investors in 1994 and 1995. “Closed,” however, did not mean that LTCM would not accept new investors under any circumstances. Rather, Portfolio remained open, in the discretion of the principals, to investors who provided strategic benefits or advantages to Long Term.
9
A strategic investor was one that
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Long Term believed added value over and above the normal fees earned on any investment; procurement of fees alone did not constitute “strategic value.”
10
Long Term had an unrestricted right to redeem an investor’s interests. In late 1997, following investors declining voluntary dividends in early summer, Long Term decided to return approximately $2.7 billion in capital to its investors,
11
having concluded after extensive debate within the management committee that a reduction in capital was more in keeping with achieving a certain return relative to an agreed risk level.
12
After the capital return, Portfolio had a balance sheet of $5 billion, and its investment positions were virtually unchanged although supported by less equity. No capital was returned to LTCM so that its stake in Portfolio increased from 30 to 45 percent.
Long Term’s historical gross returns (without deduction of fees) were 28% for the ten months of its operation in 1994, 58.77% for 1995, 57.46% for 1996, and at least 21.55% in 1997. During only nine months in this 1994-1997 time period was its overall return negative although there was a decline in expected returns. Long Term examined its portfolio annually to adjust its expected return figure, making conservative estimates which only considered existing positions and did not account for new profit opportunities. When first marketing the fund, Long Term told investors it thought it could make a 30% to 40% overall return. In Summer 1997, concurrent with its request that investors take a voluntary dividend, Long Term advised investors that investing opportunities had decreased and percentage expected returns to them would be mid-teens (with expected gross returns in the low 20s). Internally, Long Term “thought [it was] going to make 30 to 40 percent gross returns in ’94, ... low 20s in ’97, and maybe mid-20s in 1996.... ” Tr. [Doc. #188] at 2271: 17-20.
B. Babcock and Brown (“B & B”) and Onslow Trading and Commercial LLC (“OTC”)
B & B is a San Francisco-based investment banking firm in the business of asset-based financing, including acquisition and sale or management of assets and advising
*132
on the same. Richard Koffey, formerly a partner at the law firm of Morgan, Lewis, and Bockius, where he specialized in leveraged lease transactions, joined B & B in 1987. OTC was incorporated under the laws of the Turks and Caicos Islands on June 29, 1994, by three United Kingdom principals, Sir Geoffrey Leigh, Dominique Lubar, and Gregory Wills. Each principal capitalized OTC with a contribution of $2,500 and a personal loan commitment of $1.5 million.
C. CHIPS and TRIPS Transactions
Two types of cross-border leasing transactions, CHIPS and TRIPS, are claimed by petitioners to have produced the basis in the preferred stock which Portfolio sold in 1997 to generate claimed capital losses of over one hundred million dollars allocated to LTCM but disallowed by the IRS. Koffey was the principal designer and mastermind of both CHIPS and TRIPS, and Shearman & Sterling advised B & B on their structure, issuing legal opinions that the leases involved therein were true leases. OTC was formed specifically for the purpose of participating in the CHIPS and TRIPS leasing transactions because a U.K. entity was needed to create the purported tax benefits created by the transactions.
13
Five CHIPS transactions were completed and a sixth was unwound after it had begun. While the details of each CHIPS and TRIPS transaction differ slightly, each type shared a common structure. The Court focuses only on the transactions the parties have denominated CHIPS IVA and IVB and TRIPS I as those are the transactions that produced the lots of preferred stock sold by Portfolio in 1997 purportedly to generate the tax losses claimed by petitioners. Because the Court finds it unnecessary to address the economic substance of the CHIPS IVA and IVB and TRIPS I transactions, applicability of the step-transaction doctrine to them, or whether the purported 26 U.S.C. § 351 tax free exchange embedded in them in fact generated stock in the hands of OTC with the tax basis Long Term claims (three legal theories proposed by the Government), the Court will only set out background details on these transactions between OTC and Long Term necessary for understanding the Court’s conclusions.
14
1. CHIPS IVA and IVB
The CHIPS IVA transaction employed the following steps, all of which except the last took place on July 5,1995:
1. OTC entered into a Master Lease Agreement (“CHIPS IVA Master Lease”) with General Electric Capital Computer Leasing, Inc. (“GECCL”). The CHIPS IVA Master Lease was for a term of approximately 60 months and set out the terms for leasing computer hardware equipment (“CHIPS IVA Equipment”) to OTC, subject to existing leases to end users previously entered into by GECCL (“User Leases”). The User Leases had an average duration of 36 months, denominated the “Base Term” in the CHIPS IVA Master Lease. The period from the end of the Base Term to the end of the CHIPS IVA Master Lease was denominated the “Supplemental Term.”
2. OTC also entered into an Agreement of Sublease (“CHIPS IVA Sublease”)
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with Britamer Computer Co., L.P. (“Bri-tamer”). Britamer was a partnership of B & B and a company called Cebera.
15
The CHIPS IVA Sublease provided for the sublease of the CHIPS IVA Equipment from OTC as sublessor to Britamer as sublessee, and was for a term of approximately 46 months. During the period of overlap between the CHIPS IVA Master Lease and the CHIPS IVA Sublease, Bri-tamer was entitled to receive rents generated by the User Leases, OTC was entitled to receive rents from Britamer, and GECCL was entitled to receive rents from OTC.
3. Britamer entered into a Loan Agreement with Barclays Financial & Leasing B.V. (“Barclays B.V.”) pursuant to which Britamer borrowed $46,133,860.27, or 91.5% of the present value of the rents due to Britamer under the User Leases.
4. Britamer prepaid to OTC $46,638,053, or 92.5% of the present value of the rents due to Britamer under the User Leases (the “Britamer Prepayment”).
5. OTC used the Britamer Prepayment to purchase a U.S. Treasury Bill in the amount of $46,633,446 (“CHIPS IVA Treasury Bill”).
6. GECCL and Barclays (PLC) Guaranty entered into a guaranty agreement (the “Barclays/GECCL Guaranty”) whereby Barclays (PLC) guaranteed payment of a portion of the rent due to GECCL under the CHIPS IVA Master Lease in an amount equal to the future value of the Britamer Prepayment.
7. OTC and Barclays (PLC) entered an agreement (“CHIPS IVA Onslow Agreement”) whereby OTC agreed (a) to reimburse Barclays (PLC) for any amount paid under the Barclays/GECCL Guaranty, (b) granted a security interest in the CHIPS IVA Treasury Bill to Barclays (PLC) as collateral to secure OTC’s obligations under the CHIPS IVA Onslow Agreement, and (c) agreed to provide substitute collateral in the future in the form of U.S. Treasury obligations or a deposit account at Barclays Finance Corporation of the Cayman Islands, Ltd. (“Barfinco”).
8. GECCL and Britamer entered into a Service and Remarketing Agreement providing that GECCL would, for a fee, perform the servicing of the leases and be responsible for remarketing any CHIPS IVA Equipment at the expiration or termination of the User Leases.
9. On August 4, 1995, OTC and Quest & Associates, Inc. (“Quest”) entered into an Exchange Agreement (the “Quest Exchange Agreement”). Quest was an existing subsidiary of the Interpublic Group of Companies, Inc. (“Interpublic”). Under the Quest Exchange Agreement, OTC transferred its purported interests in the CHIPS IVA Master Lease, the CHIPS IVA Sublease, the CHIPS IVA Treasury Bill and the CHIPS IVA Barfinco deposit account (the “Quest Exchange Property”) to Quest in return for 505 shares of Quest preferred stock (the “Quest Preferred Stock”). Also on August 4, 1995, Inter-public contributed $2,510,000 to Quest in exchange for 510 shares of Series A preferred stock.
The CHIPS IVB transaction employed the following steps, all of which except the last took place on July 5,1995:
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1. OTC entered into a Master Lease Agreement (“CHIPS IVB Master Lease”) with GECCL. The CHIPS IVB Master Lease was for a term of approximately 60 months, and set the terms for the leasing of computer hardware equipment (“CHIPS IVB Equipment”) to OTC subject to existing User Leases with an average duration of 36 months (the “Base Term” under the CHIPS IVB Master Lease). The period beginning with the end of the Base Term until the end of the CHIPS IVB Master Lease was denominated the “Supplemental Term.”
2. OTC entered into an Agreement of Sublease (“CHIPS IVB Sublease”) with Briternational Computer Co., L.P. (“Bri-ternational”), providing for the sublease of the CHIPS IVB Equipment from OTC as sublessor to Briternational as sublessee for a term of approximately 46 months. Similar to CHIPS IVA, during the period of overlap between the CHIPS IVB Master Lease and the CHIPS IVB Sublease, Bri-ternational was entitled to receive rents generated by the User Leases, OTC was entitled to receive rents from Britamer, and GECCL was entitled to receive rents from OTC.
3. Briternational entered into a Loan Agreement with Barclays B.V. pursuant to which Briternational borrowed 91.5% of the present value of the rents due to it under the User Leases.
4. Briternational prepaid to OTC $33,824,986.53 (92.5% of the present value of the rents due to Briternational under the User Leases (the “Briternational Prepayment”)).
5. OTC used the Briternational Prepayment to purchase a U.S. Treasury Bill in the amount of $33,816,182 (“CHIPS IVB Treasury Bill”).
6. GECCL and Barclays (PLC) Guaranty entered into a guaranty agreement (the “CHIPS IVB Barclays/GECCL Guaranty”) whereby Barclays (PLC) guaranteed payment of a portion of the rent due to GECCL under the CHIPS IVB Master Lease in an amount equal to the future value of the Briternational Prepayment.
7. OTC and Barclays (PLC) entered an agreement (“CHIPS IVB Onslow Agreement”) in which OTC agreed (a) to reimburse Barclays (PLC) for any amount paid under the Barclays/Guaranty, (b) granted a security interest in the CHIPS IVB Treasury Bill to Barclays (PLC) as collateral to secure OTC’s obligations under the CHIPS IVB Onslow Agreement, and (c) agreed to provide substitute collateral in the future in the form of U.S. Treasury obligations or a deposit account at Barfin-co.
8. GECCL and Briternational entered into a Service and Remarketing Agreement providing that GECCL would, for a fee, perform the servicing of the leases and be responsible for remarketing any CHIPS IVB Equipment at the expiration or termination of the User Leases.
9. On August 2, 1995, OTC and Rorer International Corporation (“Rorer”) entered into an Exchange Agreement (the “Rorer Exchange Agreement”). Rorer was an existing subsidiary of Rhone-Pou-lenc Rorer, Inc. (“RPR”). Under the Rorer Exchange Agreement, OTC transferred its purported interests in the CHIPS IVB Master Lease, the CHIPS IVB Sublease, the CHIPS IVB OTC/Barclays Guaranty, the CHIPS IVB Treasury Bill and the CHIPS IVB Barfínco deposit account, the TRAC Lease, the TRIPS Sublease and the TRIPS Deposit (the “Rorer Exchange Property”)
16
to Rorer in return for 6,600
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shares of Series B preferred stock issued by Rorer (the “Rorer Preferred Stock”). Also on August 2, 1995, another RPR subsidiary, Rorer Pharmaceutical Products Inc. (“RPPI”), contributed $10 million to Rorer in exchange for an amount of Rorer common stock equal to approximately 33.11% of the total issued and outstanding Rorer common stock.
2.TRIPS I
The TRIPS I transaction employed the following steps:
1. On June 30, 1995, OTC entered into a TRAC Lease agreement (the “TRAC Lease”) with NationsBanc Corporation of North Carolina (“NationsBanc”), which provided for the lease of long-haul truck tractors (“TRIPS Equipment”) to OTC. The TRAC Lease was for a term of 4.5 years.
2. On June 30, 1995, OTC entered into a Sublease agreement (the “TRIPS Sublease”) with Wal-Mart Stores, Inc. (“Wal-Mart”), which provided for the sublease of the TRIPS Equipment from OTC as sub-lessor to Wal-Mart as sublessee. The TRIPS Sublease was for a term of 4.5 years.
3. On July 5, 1995, Wal-Mart prepaid to OTC $26,773,985, or 92.5% of the present value of the rents due to OTC under the TRIPS Sublease (the “Wal-Mart Prepayment”).
4. OTC deposited with Sanwa Bank Ltd. (“Sanwa”) the Wal-Mart Prepayment of $26,687,000 (“TRIPS Deposit”).
5. OTC granted a security interest in the TRIPS Deposit as collateral security to secure its obligations under the TRAC Lease.
6. As described above, on August 2, 1995, OTC and Rorer International Corporation (“Rorer”) entered into an Exchange Agreement (the “Rorer Exchange Agreement”). Rorer was an existing subsidiary of Rhone-Poulenc Rorer, Inc. (“RPR”). Under the Rorer Exchange Agreement, OTC transferred its purported interests in the CHIPS IVB Master Lease, the CHIPS IVB Sublease, the CHIPS IVB OTC/Bar-clays Guaranty, the CHIPS IVB Treasury Bill and the CHIPS IVB Barfinco deposit account, the TRAC Lease, the TRIPS Sublease and the TRIPS Deposit (the “Rorer Exchange Property”) to Rorer in return for 6,600 shares of Series B preferred stock issued by Rorer (the “Rorer Preferred Stock”). Also on August 2, 1995, another RPR subsidiary, Rorer Pharmaceutical Products Inc. (“RPPI”), contributed $10 million to Rorer in exchange for an amount of Rorer common stock equal to approximately 33.11% of the total issued and outstanding Rorer common stock.
3.Purported Tax Consequences of CHIPS IVA and IVB and TRIPS I
The CHIPS and TRIPS transactions were designed to take advantage of OTC’s status as a foreign entity not subject to U.S. taxes, the United Kingdom’s tax laws under which prepayments of rent are not taxed until rent actually accrues, and U.S. tax law regarding non-recognition incorporation transactions. In theory, the prepayments OTC received were not taxable to it under U.S. tax law because of its foreign entity status, and were not taxable under U.K. law because, as “prepayments,” rents had not yet accrued under the subleases. Based on this theory, OTC’s business plan called for OTC to transfer its purported lease interests, treasury bills, and bank deposits associated with any particular CHIPS and TRIPS transaction as soon as it could identify an appropriate American corporation (Quest in CHIPS IVA and Rorer in CHIPS IVB and TRIPS I) to take them over. It was OTC’s expectation that the transfer could be accomplished in a couple of months and
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thus would be effected prior to any accrual of rent. Each transfer was cast as a tax free incorporation under 26 U.S.C. § 351 pursuant to which the American corporation claimed no recognition of income from the prepayments it received from OTC (Quest and Rorer combined received approximately $100 million in prepayments in CHIPS IVA, CHIPS IVB, and TRIPS I), and OTC, although receiving in exchange preferred stock only valued at a small fraction of the prepayments it exchanged (approximately $1 million for CHIPS IVA, CHIPS IVB, and TRIPS I), was not required to adjust its carry over basis in stock under 26 U.S.C. § 358 from the purported tax basis it claimed to have had in the prepayments prior to the exchange. B & B required the American corporations to pay it several million dollars in fees per transaction. In this way, the income represented by prepayments of rent was never taxed but was claimed to have been stripped away from the corresponding deductions the American corporations claimed after making the rental payments required of them under the master leases with withdrawals from the bank accounts received from OTC. In sum, for every approximately $1 million in preferred stock and several million dollars in fees to Koffey and B & B with which the American corporations parted, they received in exchange guaranteed tax savings of $40 million (approximately $100 million in deductions multiplied by corporate tax rates).
B & B next endeavored to transfer the capital losses claimed to be inherent in OTC’s preferred stock (for CHIPS IVA, CHIPS IVB, and TRIPS I purportedly having a fair market value of $1 million but a carry over tax basis one hundred times that amount) to a U.S. tax paying entity.
D. OTC and Long Term
The following outline of the structure of both the transaction in which OTC and Long Term engaged as well as the transactions in which Long Term, B & B, and Union Bank of Switzerland (“UBS”) participated provides the background for the Court’s holdings that the transaction in which OTC and Long Term engaged lacked economic substance and therefore must be disregarded for tax purposes, and, in the alternative, must be recast under the step transaction doctrine as a sale of preferred stock by OTC to Long Term.
1. OTC/Long Term Transaction
On- August 1, 1996, OTC acquired a limited partnership interest in LTCP. Pursuant to a subscription agreement dated August 1, 1996, OTC contributed cash in the amount of $2,833,451 and preferred stock with a market value of $2,506,549 to LTCP in exchange for a partnership interest with an initial capital account of $5,340,000. The preferred stock contributed to LTCP by OTC on August 1, 1996 consisted of the Rorer Preferred Stock, as well as other preferred stock that OTC acquired in other CHIPS transactions.
17
On August 1, 1996, LTCM (UK), a United Kingdom limited partnership,
18
made a secured, recourse loan to OTC in the amount of $5,010,451. This loan bore in
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terest at the market rate of 7% per annum and had a maturity date of November 21, 1997. From the proceeds of this loan, OTC used $2,833,451 to fund its cash contribution to LTCP, $2,116,000 to repay existing indebtedness that encumbered the contributed stock, and $61,000 to purchase two put options from LTCM. The loan was secured by OTC’s limited partnership interest in LTCP and the two put options.
The two put options sold by LTCM to OTC on August 1, 1996 were a “liquidity put” and a “downside put.” The liquidity put provided OTC with the option to sell its partnership interest in LTCP to LTCM during the period October 27, 1997 through October 31, 1997, at a strike price equal to the net asset value of its partnership interest as determined under the LTCP partnership agreement. OTC paid LTCM $1,000 for the liquidity put.
The downside put provided, OTC with the option to sell its partnership interest in LTCP to LTCM during the period October 27, 1997 through October 31, 1997, at a strike price equal to $5,340,000 (the value of OTC’s initial capital account with LTCP). OTC paid LTCM $60,000 for the downside put.
On August 1, 1996, the preferred stock and cash contributed to LTCP by OTC was contributed by LTCP to Portfolio. As a result, LTCP received an increase in its capital account in Portfolio of $5,340,000.
On November 1, 1996, OTC acquired an additional limited partnership interest in LTCP. Pursuant to a subscription agreement dated November 1, 1996, OTC contributed cash in the amount of $3,356,467 and preferred stock with a market value of $1,643,533 to LTCP in exchange for a partnership interest with an initial capital account in LTCP of $5,000,000. The preferred stock contributed to LTCP by OTC on November 1, 1996 consisted of the Quest Preferred Stock as well as other preferred stock that OTC acquired in other CHIPS transactions.
19
On November 1, 1996, LTCM (UK) made another secured, recourse loan to OTC in the amount of $4,316,842 with market rate interest again of 7% per annum and with a maturity date of November 21, 1997. From the proceeds of this loan, OTC used $3,356,467 to fund its cash contribution to LTCP, $900,375 to repay existing indebtedness that encumbered the contributed stock, and $60,000 to purchase two put options from LTCM. This loan, too, was secured by OTC’s limited partnership interest in LTCP and the two put options.
As previously, the two put options sold by LTCM to OTC on November 1, 1996 included a liquidity put and a downside put. The liquidity put provided OTC with the- option to sell its partnership interest in LTCP to LTCM during the identical period as before, October 27, 1997 through October 31, 1997, at a strike price equal to the net asset value of the partnership interest as determined under the LTCP partnership agreement. OTC paid LTCM $1,000 for the liquidity put.
The downside put provided OTC with the option to sell its partnership interest in LTCP to LTCM during the period October 27, 1997 through October 31, 1997, at a strike price equal to $5,000,000. OTC paid LTCM $59,000 for the downside put.
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On November 1, 1996, the preferred stock and cash contributed to LTCP by OTC was contributed by LTCP to Portfolio resulting in an increase in LTCP’s capital account in Portfolio of $5,000,000.
On October 28, 1997, OTC exercised its August 1, 1996 and November 1, 1996 liquidity put options and OTC sold its limited partnership interests in LTCP to LTCM as of October 31, 1997, for $12,614,188, an amount representing the aggregate fair market value of OTC’s capital account in LTCP on October 31, 1997. Based upon the total investment in LTCP by OTC in 1996 and 1997, LTCM earned management and incentive fees of $1,061,848.
Based upon bid estimates provided by Salomon, on December 30, 1997, Portfolio sold the Rorer Preferred Stock to an affiliate of Merrill Lynch & Co., Inc. (“Merrill”) for $613,800, which represented the fair market value of that preferred stock on December 30, 1997. On December 30, 1997, Portfolio sold the Quest Preferred Stock to an affiliate of Merrill for $464,600, which represented the fair market value of that preferred stock on December 30, 1997.
2. Long Term/B & B/UBS Transaction
Effective September 1, 1996, Carillon LLC (“Carillon”), a partnership whose partners included members of B & B, purchased a call option from UBS for a premium of $2,001,650, which provided that on August 31, 2001, Carillon could acquire from UBS an interest in LTCP representing the growth in a $30,000,000 capital account on September 1, 1996, for a strike price of $44,000,000. The call option had an expiration date of August 31, 2001.
Effective September 1, 1996, UBS invested $30,000,000 in Long-Term Capital, Ltd., a Cayman Islands company (“LTCL”) and purchased a put option from LTCM for a premium of $2,349,000, which provided that on August 31, 2001, UBS could sell to LTCM an interest in LTCL representing a $30,000,000 capital account on September 1, 1996, for a strike price of $44,000,000. The put option had an expiration date of August 31, 2001.
As of January 1, 1997, Carillon purchased another call option from UBS for a premium of $1,700,000, which provided that on December 31, 2001, Carillon could acquire from UBS an interest in LTCP representing a $20,000,000 capital account on January 1, 1997 for a strike price of $28,520,000. The call option had an expiration date of December 31, 2001.
Also effective January 1, 1997, UBS invested $20,000,000 in LTCL and purchased a put option from LTCM for a premium of $1,700,000, which provided that on December 31, 2001, UBS could sell to LTCM an interest in LTCL representing a $20,000,000 capital account on January 1, 1997, for a strike price of $28,520,000. The put option had an expiration date of December 31, 2001.
Through the end of 1997, LTCM earned management and incentive fees from the UBS investments made as part of the first UBS/B & B transaction of $3,597,504 and $1,580,387 from the second UBS/B & B transaction. The total fees earned by LTCM in 1996 and 1997 from both of these investments was $5,177,891.
As the structure and how UBS viewed the transaction makes apparent, these transactions were essentially a loan to Long Term from UBS at the LIBOR
20
rate plus fifty basis points. Ronald Ten-
*139
nenbaum, head of global fund coverage at UBS during 1996 and UBS’ representative working with Scholes on the transaction, described the sale of call options to Carillon’ and UBS’ corresponding purchase of put options from Long Term: “[E]ssentially it works into a lending type of transaction .... But it looks more like a lending type transaction, or a use of balance sheet type transaction, where you are basically buying something today and selling it in 5 years time, so you need to earn interest over that period. Then the question becomes ‘okay, what rate of interest is appropriate given the risk,’ and that was deemed to have been 50 basis points over LIBOR on the first transaction and then, you know, we made a little bit more on the second transaction.” Govt. Ex. 436 at 9:14-23;
see also id.
at 49:21 (“I thought we were being paid for essentially lending money....”). Accordingly, UBS primarily focused on the strike price and exercise date of the options in negotiations with Scholes and Long Term and did not negotiate with B & B at all over the cost of the call options but left that matter to Long Term and B & B. UBS’ lending risk was the possibility that Long Term would not be able to perform if and when UBS put its options to Long Term at their respective strike prices.
21
3. Long Term’s Tax Returns
Rosenfeld was the tax matters partner for Long Term and responsible for ensuring the timely filing of accurate tax returns. He accomplished his task by delegating responsibility to Noe and outside accountants, including Price Waterhouse, expecting them to look at and raise important issues for his consideration. Long Term claimed losses of $106,058,228 resulting from the sale of Quest and Rorer preferred stock on its U.S. Return of Partnership Income (Form 1065) for its 1997 tax year. This claim was premised on Long Term’s claim that, after acquiring OTC’s partnership interest in Partners, it succeeded to OTC’s purported basis (approximately $100 million) in the Rorer and Quest preferred stock and the sale of the stock on December 31, 1997 for approximately $1,000,000 thus produced these capital losses. Long Term reported the losses as “Net Unrealized Gains” on line 6 of Schedule M-l.
See e.g.,
Pets.’ Exs. 319, 332. An internally prepared draft copy of Portfolio’s return used the description “Net Capital Gains/Losses,”
see
Govt.’s Ex. 321, which was changed after input from Coopers & Lybrand and Price Waterhouse to its final form, “Net Unrealized Gains.” Pursuant to 26 U.S.C. § 704 (c), Portfolio allocated the losses to LTCP, and LTCP allocated them to LTCM. The losses were then allocated by LTCM to LTCM’s partners and indirect partners under 26 U.S.C. § 704 (b).
4. B & B and OTC After CHIPS and TRIPS
B & B expected to market for significant fees the preferred stock OTC obtained from the CHIPS and TRIPS transactions, including CHIPS LVA, CHIPS IVB, and TRIPS I. By fee agreements dated July 5, 1995 (the date of commence
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ment of the CHIPS IVA and CHIPS IVB transactions but prior to the August 2 and 4, 1995 exchanges with Rorer and Quest), OTC and B & B agreed that B
&
B would be OTC’s exclusive agent for the sale of any non-cash consideration received in connection with the CHIPS IVA, CHIPS IVB, and TRIPS I transactions,
see
Pets.’ Exs. 159, 160, and 161, namely, the Rorer and Quest Preferred Stock. The exclusive agency was to last at least six months, and B & B was to earn a fee from the disposition of the stock, which was to be negotiated among the parties. Even after a termination of its exclusive agency, B & B retained the right to purchase the stock before OTC transferred it to another. This was a poison pill provision designed to assure that, if OTC and/or another tax product promoter attempted to cut B & B out of a deal involving the purportedly high basis stock, B & B could buy the stock and thereby destroy the claimed high basis. The exclusive agency and poison pill provisions in these fee agreements were, for all relevant purposes, identical to the ones in the fee agreements B & B and OTC had for all CHIPS transactions.
See
Tr. [Doc. # 163] at 314:24-315:7; Govt/s Ex. 120.
22
Regarding CHIPS II, Koffey estimated that the preferred stock OTC obtained from that transaction, because of its purportedly high tax basis and attendant “$100 million of deductions,” Tr. [Doc. # 163] at 327:2-3, could be transferred for a fee ranging from seven to nine million dollars as long as the structure of the transaction did not hurt those deductions, i.e., diminish the disparity between fair market value and purported tax basis,
see id.
at 324:9-327:6 ; Tr. [Doc. #164] at 456:18-23; Govt’s Ex. 172.
23
Initial marketing attempts had begun by early 1995. Koffey developed a structure
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in which OTC would exchange its high basis preferred stock for preferred stock of another corporation. Koffey inquired of Shearman & Sterling on the viability of the structure, and Shearman & Sterling responded that the proposed exchange would not satisfy the requirements of 26 U.S.C. § 351 . Simultaneously, Koffey asked Shearman & Sterling to render a legal opinion that OTC’s tax basis in the CHIPS and TRIPS preferred stock exceeded $90 million.
24
Koffey’s idea was to market the stock to a potential acquirer with a basis opinion from Shearman & Sterling and allow the acquirer to construct a transaction for transferring the high basis stock into its hands without diminishing the basis. Shearman & Sterling informed Koffey that it could render the requested basis opinion. The opinion Shearman & Sterling agreed to render was essentially the same opinion it ultimately delivered to Long Term in connection with OTC’s contributions of preferred stock to LTCP.
Part of Shearman & Sterling’s work on the opinion requested by Koffey was billed to Long Term’s account notwithstanding that it was performed on behalf of B & B prior to Long Term’s retention of Shear-man & Sterling to opine on the OTC transaction. While the recollections of Woody Flowers and John Sykes, Shearman and Sterling’s testifying tax lawyers were faded, their initial discussions with Koffey “could have” begun as early as February 1995. Tr. [Doc. # 179] at 1520:4. Shear-man & Sterling’s internal billing records reveal that Shearman & Sterling’s attorneys were billing time in early March 1996 under matters described as “[r]eview memo regarding preferred stock,” “meeting with J. Sykes regarding B & B transaction issues...,” “revise memo regarding new structure,” “[l]egal research regarding transferee liability; sections 482 and 351 and 269,” “[r]eview Koffey memo regarding stock sale by OTC (CHIPS)...,” etc.
See
Pets.’ Ex. 290.
25
In Shearman & Sterling’s records, these billing entries are assigned to Long Term’s account number even though Shearman & Sterling’s representation of Long Term did not commence until April 11,1996.
26
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As for OTC, under its business plan, it had no interest in retaining the CHIPS and TRIPS preferred stock but desired to dispose of it for cash as early as legally possible.
5. The Origin of a Transaction for Long Term
In early 1996, James Babcock of B & B approached Donald R. Turlington, a New York tax lawyer who served as regular tax counsel to
Long Term in
the mid-1990s.
27
Over dinner in New York City, Babcock discussed with Turlington the potential placement of preferred stock with high basis, and, either at the same dinner or shortly thereafter, Babcock agreed that, if Turlington assisted in the placement of the stock, B
&
B would compensate Turlington with a percentage of the profits B
&
B earned from the placement.
Shortly after his discussions with Bab-cock, Turlington was at Long Term’s offices in Greenwich, Connecticut, for a meeting unrelated to Babcock’s high basis stock proposal. After the meeting ended, Turlington approached Noe about an idea involving preferred stock he thought might be beneficial to the partners in Long Term. When Noe expressed interest, Tur-lington summarized a transaction in which an investor that owned a security with a tax basis higher than the value of the security would contribute the security to LTCP in exchange for a partnership interest and, if LTCM subsequently were to purchase the investor’s partnership interest before Portfolio sold the contributed securities, the tax law would permit “the tax deduction,” Tr. [Doc. # 174] at 1026:12, the capital loss, generated from the sale to be allocated to LTCM. The discussion was about the availability of preferred stock with high basis, the mechanism by which to get the stock into Long Term, and the technique for allocating the capital losses generated upon sale to the Long Term principals through LTCM by means of loss allocation rules of U.S. partnership tax laws. Other than a bare description of an investor having stock with a tax basis higher than its fair market value, the discussion was unconcerned with the identity or characteristics of the investor. In fact, at the time, Turlington was unaware that OTC was the nominal owner of the preferred stock, and Noe’s purpose at Long Term was to handle tax matters not matters related to potential new investors.
Although Noe had no experience in high basis stock transactions, as a sophisticated tax practitioner, he understood the potential tax benefits that Long Term’s partners could obtain from such stock, and explained Turlington’s idea to Scholes by way of querying Long Term’s interest. Scholes, who among Long Term’s principals would assume primary responsibility for the OTC transaction, informed Noe that Long Term was interested and directed him to pursue it further, specifically with the goal of determining what the high basis asset was and why it had high basis. Noe and Scholes were well aware of the tax law requirements of economic substance and business purpose and discussed the need therefore to figure out a reason independent of taxes for Long Term to engage in a transaction with the holders of the high basis preferred stock, understanding that Long Term “would have to have a way ... to expect to profit from that interaction.” Tr. [Doc. # 179] at 1611:10-13.
Noe conveyed Long Term’s interest to Turlington, and Turlington introduced Noe to B & B and Shearman & Sterling. Hav
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ing advised B
&
B on the structure of and rendered true lease opinions for the CHIPS and TRIPS transactions, Shear-man & Sterling had access to the documentation related to both, and Turlington instructed Noe that he needed to speak with both B
&
B and Shearman
&
Sterling because of their knowledge of those transactions.
28
Turlington also recommended to Noe and Long Term the law firm of King & Spalding for advice on the potential federal partnership tax consequences of any contribution of preferred stock to LTCP and possible subsequent sale of the contributor’s partnership interest to LTCM. Shortly after attending an initial meeting with Noe and Shearman
&
Sterling, Turlington’s role ended when potential conflicts of interest were recognized. Long Term’s interactions and discussion with B & B, Shearman & Sterling, and King
&
Spalding began in March or April 1996.
6. Long Term and B & B
Having been introduced to B
&
B by Turlington and having learned that B
&
B was acting as advisor to the holder of the high basis CHIPS and TRIPS preferred stock, Scholes had Noe arrange dinner with Koffey in March 1996 in San Francisco to discuss Long Term’s potential acquisition of the stock by means of a transaction following the structure outlined by Turlington, including the then unknown holder of the stock becoming a partner in LTCP. At this initial meeting, Koffey did not tell Noe and Scholes about OTC, and Noe and Scholes did not ask for the identity of the owner of the preferred stock. Rather the discussion focused on the availability of the stock, the structure of the CHIPS and TRIPS transactions as it related to generating the stock’s purported high basis, and the means by which Long Term might acquire the stock.
29
A precise chronological time line of interaction between or among Noe, Scholes, Koffey, and B & B subsequent to that dinner in San Francisco cannot be reconstructed with any precision from the testimony. What is clear is that following shortly thereafter, Noe and Scholes engaged in a series of meetings or discussions with Koffey and then continued to work closely with him on the acquisition of OTC’s CHIPS and TRIPS preferred stock until OTC made its contributions to LTCP. During this time frame, Koffey responded to Noe’s and Scholes’ inquiries regarding OTC, the terms of OTC’s preferred stock, and “knowing ... that the structure that [Long Term] had in mind provided [Long Term] with the tax benefit,” Tr. [Doc. # 161] 161:2-3, the structure of the CHIPS and TRIPS transactions and how it was claimed to generate the stock’s purported high basis. Noe and Scholes were aware of the potential for hundreds of millions of dollars of tax deductions in connection with acquisition of the stock and understood from B & B that such tax benefit stood to be obtained in exchange for roughly a few million dollars (the approximate value of OTC’s tranches of preferred stock).
30
Noe and Scholes discussed with Koffey whether B & B would be entitled to a cash fee for facilitating acquisition of OTC’s
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preferred stock and indicated that Long Term was only interested in a transaction in which no cash fees would be paid. Long Term was worried that paying a cash fee could be construed as buying tax benefits which would raise questions about the economic substance of the transaction or Long Term’s business purpose for it. According to Noe, who during this time frame had specific discussions with Long Term’s principals about the tax law doctrines of sham transaction and economic substance, Long Term’s goal was to “construct a real business transaction so that doctrines like economic substance, business purpose and sham would not be issues.” Tr. [Doc. # 169] at 703:17-20. He stated that Long Term was
not interested in a transaction where there would be cash compensation to anyone. [Long Term’s] idea was that [it] wanted a transaction, a fund investment where someone would be — ■ would find the attractiveness in investing in the funds and take the total risk and economic benefit of the fund, and if that’s what they were interested in, then that’s the transaction [Long Term] wanted to do.
Id.
at 573:7-13 . Long Term thus proposed that, instead of a cash fee, B & B settle for an investment in Long Term, and Scholes marketed the investment idea to Koffey by representing that the expected investor return into the future of such an investment would be 21%. After some time, B & B agreed to take an investment in Porfolio in connection with the OTC transaction in lieu of the outright payment of a cash fee labeled as such.
31
On the same day OTC contributed its Quest Preferred Stock to LTCP, November 1, 1996, Long Term and B & B entered into a “consulting arrangement” pursuant to which Long Term agreed to pay B
&
B $100,000 per month for one year.
32
Long Term had not before and did not after enter into any kind of comparable consulting arrangement with any other investment banking firm, and did not renew the agreement after its expiration. Koffey had proposed the agreement to Scholes, and did so only after Scholes and Noe made it clear that Long Term would not pay formal cash fees for B & B’s facilitation of the OTC transaction. There were never any specific discussions between Scholes and B & B regarding how B & B would earn its $1.2 million “consulting fee” and the agreement itself imposed no performance requirements on B & B. The written terms of the agreement explicitly provided that B & B would also be entitled to additional fees to be negotiated on a transaction-specific basis. Although the agreement had a thirty day notice provision pursuant to which Long Term could cancel it, Long Term never exercised that right and paid B & B $1.2 million over the course of the year the agreement was in place.
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While the “consulting arrangement” was in place, B & B and Long Term worked together on a tax oriented transaction termed “LIPS” that B & B brought to Long Term and that sought to take advantage of tax opportunities created by tax treaties between different countries. B & B indicated that its fee for the “LIPS” transaction was not to fall below 7.5% of the “benefit of the deal,” which, if not totally comprised of the hoped for tax benefit to Long Term, was at least a component thereof.
33
7. Long Term and Shearman & Sterling
Also at some time in March or April of 1996, Turlington arranged an initial meeting for Long Term with Sykes at Shear-man & Sterling. The meeting focused on providing Long Term with an understanding of the underlying CHIPS and TRIPS transactions, Shearman
&
Sterling’s involvement as special counsel to B & B in those transactions, and what level of opinion Shearman & Sterling could render on the tax bases of the different tranches of OTC’s CHIPS and TRIPS preferred stock. Either at the initial meeting or shortly thereafter, Noe and Long Term made it clear to Sykes that Long Term only wanted a legal opinion if it could be rendered at a “should” level.
34
After Shearman & Sterling assured Long Term that it had the relevant knowledge of and access to information about the CHIPS and TRIPS transactions and could render legal opinions on the bases of OTC’s CHIPS and TRIPS preferred stock tranches at the “should” level, Long Term retained the firm for that purpose. Sykes was selected as the Shearman & Sterling tax lawyer with primary responsibility for the representation, all legal opinions requested were to be rendered prior to the closing of the contribution transaction to which each related, and by letter dated April 26, 1996, the retention was retroactively made effective April 11, 1996. Long Term insisted on April 11 as the date of commencement of the representation because Long Term “wanted to establish a date when [Shearman
&
Sterling was] representing [Long Term] and only [Long Term].” Tr. [Doc. # 179] at 1511:19-20. Shearman
&
Sterling began its task right away, performing substantial work on the opinions between March/April of 1996 and June 12, 1996, the date Long Term first had any contact with OTC and its principals. During the course of the representation, Noe and Sykes frequently discussed and reviewed drafts of the opinions.
Ultimately, Long Term received five virtually identical formal opinions from Shearman & Sterling in connection with OTC’s contributions to LTCP. For exam-
*146
pie, with respect to the August 1, 1996 contribution of the Rorer Exchange Property, Shearman & Sterling opined that OTC had received the preferred stock in a tax free exchange pursuant to 26 U.S.C. § 351 , that the preferred stock received in the exchange transaction had an adjusted tax basis in OTC’s hands of at least $60,503,182, a basis which was equal to OTC’s adjusted tax basis in the Rorer Exchange Property, and that, as of the date of OTC’s contribution of the stock to LTCP, the basis had not changed. The opinions substantially overlapped with the true lease opinions Shearman & Sterling had earlier rendered in the CHIPS and TRIPS transactions.
The opinions contain no legal reasoning or analysis. Rather, they set out the factual underpinning for the legal conclusions, including any representations or assumptions on which Shearman & Sterling relied. Noe testified that he understood from discussion with Sykes that Shearman & Sterling’s legal analysis was in a separate file memorandum, that the memorandum contained all the legal reasoning and authority for the legal conclusions, and that the file also included the supporting documentation and grounds for the representations and assumptions relied on in the opinion. Noe did not ask to see Shearman
&
Sterling’s legal or factual analysis and did not do any analysis himself regarding the representations and assumptions relied on in the Shearman & Sterling opinions letters, but asked Shearman
&
Sterling to make sure that all the assumptions and representations were supported by underlying facts and documents. At trial, petitioners offered a single separate file memorandum dated July 22, 1996,
see
Pet.’s Ex. 226, and while Sykes testified that the analysis contained in the memorandum was only “a part of the analysis that [Shearman & Sterling] went through in preparing the opinions,” Tr. [Doc. # 177] at 1478:16-17, neither Shearman & Sterling nor petitioners produced any other memoranda contemporaneously memorializing Shearman
&
Sterling’s legal or factual analysis. Notably absent from the memorandum is any analysis of the step transaction doctrine, 26 U.S.C. § 269 , whether B
&
B and OTC were alter egos, and sham transaction theories. Sykes claimed that, although he had no memory of having analyzed the CHIPS and TRIPS transactions in light of those code sections and legal doctrines, he was sure Shearman
&
Sterling’s legal team would have done so because “it was not uncustomary for [Shearman & Sterling] to do research and not necessarily memorialize it....” Tr. [Doc. #179] at 1508:1-2.
Other than showing Scholes a copy of Shearman & Sterling’s opinions which Scholes did not read, Noe did not circulate the opinions to any other partners of Long Term but informed them that Long Term had “should” level opinions from Shearman
&
Sterling and that the tax bases of the contributed stock tranches should be the number set forth in the opinions. Scholes explained that he did not think it necessary to read the opinions because he had worked closely with Noe throughout the process and Noe had relayed to him detailed information regarding his work and discussions with Shearman & Sterling. While Scholes was aware that the opinions contained assumptions, he says he relied on Noe’s and Shearman & Sterling’s experience with respect to both tax matters as well as Shearman & Sterling’s experience with the CHIPS and TRIPS transactions in presuming that sufficient analysis would have been done to justify the assumptions. Rosenfeld and the other principals did not review the opinions and did not ask Noe any questions about them. Rosenfeld and the others thus were not aware of the contents of the opinions, including what Shearman and Sterling had considered or assumed.
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Long Term would not have gone through with the OTC transaction without “should” level opinions from Shearman & Sterling on OTC’s tax basis in its CHIPS and TRIPS preferred stock. Long Term compensated Shearman
&
Sterling $500,000 for its opinion letters, $100,000 each, and paid an additional $13,331.69 in related costs.
8. Long Term and King & Spalding
Based on Turlington’s recommendation, Long Term retained King
&
Spalding to opine on the potential partnership tax consequences of the OTC contributions to LTCP. The retention formally began on May 22, 1996, prior to which King
&
Spalding had never been retained by Long Term. William McKee and Mark Kuller, who were the tax attorneys at King & Spalding with primary responsibility for the representation, ultimately rendered their formal legal opinion to Long Term on OTC’s stock contributions to LTCP and subsequent sale of its partnership interest in LTCP to LTCM.
35
According to Noe, Long Term
wanted someone who was expert in partnership matters to really get involved at the very initial stage of what was a potential transaction, to advise us as we went through every aspect of it, as we went really in formulating what the transaction became and also to ultimately render a tax opinion if and when it became necessary.
[Long Term] wanted [King
&
Spalding] to be involved from the outset so they were familiar with all facts, all circumstances, and not only [...] familiar with it but have an input in making decisions as we went along the way.
As the transaction developed, there was a transfer of OTC’s partnership interest to LTCM. That led to LTCM succeeding to the tax attributes that OTC had when they contributed the property.
When property was sold— if an asset was sold, that loss would be allocated back to LTCM. So we wanted— at that point, if any loss was recognized or there was any tax result from the transaction, we wanted King
&
Spalding to render an opinion that that was the proper analysis of the law and that was the proper result.
Tr. [Doc. # 169] at 651:11 — 652:14.
King & Spalding rendered its written opinion to Long Term on January 27, 1999 long after OTC’s stock contributions to LTCP and subsequent sale of its partnership interest to LTCM. Long Term had hoped to receive the King
&
Spalding written opinion prior to filing its 1997 tax return, on which it claimed the capital losses at issue in this case, but King & Spalding was not prepared at that time to
*148
issue the written opinion because it was still in draft stage. On April 14, 1998, the day before Long Term’s tax returns were filed, Noe wrote the following memorandum to file:
Long-Term Capital Portfolio, L.P. (Portfolio) generated a short-term capital loss of $59,889,382 on the sale of 6,600 shares of Rorer International Corporation (Pennsylvania) Series B preferred stock and a long-term capital loss of $46,168,846 on the sale of 505 shares of Quest & Associates, Inc. preferred stock (Loss). The bases of such securities were determined based on the opinions provided by Shearman and Sterling dated August 1, 1996 and November 1, 1996, respectively. Such Loss was allocated to [LTCP] pursuant to Internal Revenue Code section 704(c) since it related to a contribution of such property to Portfolio by [LTCP], [LTCP] then allocated the Loss to Long-Term Capital Management, L.P. (LTCM) pursuant to Internal Revenue Code section 704(c) since LTCM had acquired the capital account of Onslow Trading and Commercial LLC (OTC), the original contributor of such property. In deciding how to properly allocate the loss, I had discussions with Mark Fuller of King & Spalding. Mark, on this date, has orally confirmed that King & Spalding will issue an opinion that the allocation of such Loss, as described above, should be sustained; that is, it is properly allocable to LTCM. Mark further advised that this opinion will be rendered in accordance with the requirements of Treasury Regulation sections 1.6662-4(d), 1.6662-4(g), and 1.6664^(c). |
King
&
Spalding have based their opinion on current U.S. Federal income tax law and administrative practice as in effect on the date hereof. They have considered all pertinent facts and circumstances and the current U.S. Federal income tax law and administrative practice as it relates to such facts and circumstances. Any factual statements and assumptions are based upon their review of the documents, instruments, opinions, letters and materials and factual representations by the relevant parties, which they believe to be reasonable to rely upon and reasonable to assume and they have no reason to believe that any such items are incorrect. We have provided all relevant information to King-&-Spalding in order for them to renderjheir opinion. I know of no information or facts that may be relevant to their opinion which were not provided to King & Spalding.
Based upon the advice of King & Spald-ing, [LTCP] will allocate the Loss to LTCM pursuant to Internal Revenue Code section 704(c) and LTCM will report such Loss on its tax return. Portfolio’s and [LTCP’s] tax returns will be timely filed on April 15, 1998 while LTCM’s return will be properly extended.
Pet. Ex. 346. More than nine months after Long Term filed the disputed tax return, King & Spalding opined in writing that the tax basis of the preferred stock to LTCP after OTC’s contribution and the tax basis of the preferred stock to Portfolio after LTCP’s contribution “should” be equal to OTC’s tax basis in the preferred stock before its contribution to LTCP, that, upon the sale of the Rorer B shares and the Quest shares by Portfolio, Portfolio “should” recognize a loss for federal income tax purposes equal to the excess of Portfolio’s tax basis in the stock over the selling price of the stock, and that the loss recognized by Portfolio “should” ultimately be allocated to LTCM and correspondingly the partners of LTCM to the extent of the “built in loss” (the extent of the excess of OTC’s tax basis in the stock immediately
*149
before contribution over the fair market value of the shares at the same time).
The first page of the opinion states,
[This opinion] is prepared as part of LTCM’s litigation strategy to aid LTCM and its partners in anticipation of possible future litigation regarding certain federal income tax consequences that result from the sale of certain preferred stock by Portfolio, as further discussed herein.
Pet.’s Ex. 357 at 1-2.
36
It contains no citation to any decisions of the Second Circuit Court of Appeals whose caselaw would apply to any appeal related to Long Term’s tax return. The representations and assumptions set forth with respect to Long Term’s pretax expectation of profit from the OTC transaction include:
6. Each of the transactions addressed herein was entered into for a valid and substantial business purpose, independent of federal income tax considerations, for the purpose of deriving a material pre-tax profit, and there was a reasonable expectation of deriving such a profit (taking into account all related fees and transaction costs).
12. LTCM expected to derive a material pre-tax profit from OTC’s investment in Partners (taking into account all related fees and transaction costs) and, excluding the litigation settlement payment made to Mr. Turlington, did derive such a profit.
28. The services provided by B & B under the financial advisory agreement between B & B and LTCM were commensurate in value with the fees that were paid thereunder.
30. It was LTCM’s expectation and belief that no fee, commission, or other compensation was due or owing to Mr. Turlington by LTCM, Partners, or Portfolio relating to OTC’s investment in Partners or any other transaction addressed herein. During the period preceding December 31, 1997, there was no expectation on the part of LTCM, Partners, or Portfolio that it would make any payment to Mr. Turlington other than normal hourly fees for legal services.
31. Except for the litigation settlement payment made to Mr. Turlington by LTCM, there were no fees, commissions, premiums, or other compensation paid to OTC, B & B, or any other party in connection with, or related to, OTC’s investments in Partners or any other transaction addressed herein.
Pet's Ex. 357 at 18, 20-21, 26-27.
a. Kuller’s Claimed Pre-Tax Expectation of Profit Analysis
At trial, Kuller testified that, in rendering opinions to Long Term, he performed and discussed “at length” with Noe a calculation of Long Term’s pretax expectation of profit, including an examination of Long Term’s costs for the OTC transaction and expected return. Kuller insisted he performed this calculation to become comfortable that Long Term’s representation that it expected a material pre-tax profit from OTC’s investment was a reasonable one but that it was an “easy” analysis that he could do quickly in his head. Kuller maintained that his discussions with Noe occurred over a period of time contemporaneous to Long Term’s consideration of OTC’s stock contributions and encompassed both Kuller’s normative view as to what costs and profits should be included in the analysis in addition to what costs
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and profits a revenue agent might believe should be included. The deficient nature and substance of petitioners’ evidence about any pre-filing analysis and discussions in the time period claimed compels the Court’s conclusion that if they even took place in that time frame, it was not in the embellished form offered by Kuller’s testimony detailing the analysis he claims he did and discussed with Noe, which testimony is summarized as follows:
As Long Term’s costs, Kuller included corporate and travel fees for both the OTC and UBS/B
&
B investments of
$50,000 to
$100,000,
37
and the costs of the legal opinions from Shearman & Sterling and King
&
Spalding, which Kuller estimated at $500,000 each.
38
Kuller excluded the contemporaneous $1.2 million consulting agreement with B & B based on Noe’s assurances that the value of the consulting services provided for in the agreement were commensurate with what was being paid. Kuller also excluded any share paid by Long Term towards the joint $1.8 million settlement payment with B & B to Turlington’s law firm for Turlington’s role in introducing B
&
B to Long Term and his partnership tax idea for transference of OTC’s basis to Long Term. This exclusion was based on Noe’s assurance that, although “initially there was some suggestion from Mr. Noe that he might give Mr. Turlington something if Babcock did not agree, ... Babcock ultimately did agree to pay Mr. Turlington something, and therefore, Long-Term went into the deal believing it had no financial obligation whatsoever to Mr. Turlington.” Tr. [Doc. # 186] at 2171:3-9.
As expected profits, Kuller testified he considered that Long Term’s profits from the transaction derived primarily from the management and incentive fees it could earn from OTC’s and the UBS/B & B investments. Kuller calculated profits from fees based on what he characterized as a conservative expected investor return of 21%, which he selected based on information from Noe that Scholes and others used this figure in marketing Portfolio to investors, and on what he characterized as a historical rate of investor return for Portfolio in 1995 and 1996 of approximately 42%.
39
Based on these assumed rates of return, base investments by OTC of $10,000,000 and UBS/B & B of $50,000,000, and taking into account “that there was a put that was going to take place 15 months after [OTC’s] August investment....,” Tr.
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[Doc. # 186] at 2176:5-7, Kuller calculated annual fee returns to Long Term of either $6,750,000 (based on 21% investor return) or $12,000,000 (based on 42% investor return). Based on the large calculated returns under these assumptions, Kuller claims he discussed with Noe his belief that he did not need to extrapolate to account for the additional years of expected return from the UBS/B
&
B investment as the calculated returns would significantly outweigh transaction costs, even including the premiums for the legal opinions, the $1,200,000 B & B consulting fee, and other costs.
Although Kuller claimed he told Noe he believed the proper calculation would consider profits from both the OTC and UBS/B & B investments, he also advised Noe that the IRS might disagree and thus discussed with Noe the pre-tax profit calculation if only OTC’s $10,000,000 investment were considered. Using the assumed investor returns of 21% and 42% and a cut off date for the investment of late October 1997, Kuller calculated profits to Long Term from OTC’s investments as ranging from $1,125,000 to $2,000,000. He believed it reasonable to average the two figures to approximately $1,500,000/$1,600, 000, which return he considered showed a “reasonable expectation of profit” for Long Term.
40
b. Kuller’s Credibility
Kuller has an obvious stake in Long Term prevailing in this case. He represented petitioners during the IRS audit and has assisted in this litigation.
See supra
note 35. He also co-authored King & Spalding’s written opinion to Long Term which is under scrutiny in this case. His advocacy role was confirmed by the character of his testimony which had the distinct quality of advocacy, not an effort to just accurately report recollection, notwithstanding his protestations that he was “up here just to tell the truth as to what happened.” Tr. [Doc. # 186] at 2190:12-13. His belligerence in responding to the Government’s cross examination stood in marked contrast to his manner on direct examination by his law partner.
An important aspect of Kuller’s testimony on how costs and profits were treated in the King & Spalding written opinion was unsupported and lacked credibility. Echoing Long Term’s trial position, Kuller testified that contemporaneously with the OTC transaction he had viewed the OTC and UBS/B
&
B investments as a unit and therefore believed the costs and profits of both should be combined in evaluating Long Term’s pre-tax profit potential from the OTC transaction. In regard to this testimony, Kuller was asked on cross-examination about the following “representation/assumption” contained in the King & Spalding written opinion:
12. LTCM expected to derive a material pre-tax profit from
OTC’s investment in [LTCP]
(taking into account all related fees and transaction costs) and, excluding the litigation settlement payment made to Mr. Turlington, did derive such a profit.
See
Pets.’ Ex. 357 at 20-21 (emphasis added). Kuller insisted that he viewed the phrase “OTC’s investment in [LTCP],”
id.,
to mean the combined $60,000,000 of both the OTC and B & B investments,
see
Tr. [Doc. # 186] at 2194:14-2195:6. However, the King
&
Spalding written opinion, which he co-authored, read in the context of the econom
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ics of the OTC transaction discredits this interpretation. The fact section of the written opinion never states that the two investments were viewed as combined, and describes the OTC transaction and the UBS/B & B investment under separate headings. The word “investment” in representation/assumption number 12 is not capitalized or otherwise specially defined, and the representation/assumption makes no reference to the UBS/B & B investment. The logical reading of representation/assumption number 6, recited in full
supra
Part H.D.8., is that it covers “each of the transactions addressed herein” as it states,
see
Pets.’ Ex. 357 at 18, and the specifically identified transaction in representation/assumption number 12 refers by its terms only to the “OTC[] investment in [LTCP],”
id.
at 20.
41
Most telling is the text of representation/assumption number 12 itself which explicitly states that Long Term expected to and in fact did derive a material pre-tax profit from “OTC’s investment in [LTCP] (taking into account all related fees and transaction costs)” only if the litigation settlement payment to Turlington, which the King & Spalding written opinion identified as $1,250,000,
see
Pets.’ Ex. 357 at 10, was excluded as a transaction cost,
see id.
at 20-21. Thus, it is evident that Kuller and co-author McKee recognized as late as January 27, 1999 that $1,250,000 represented a figure which exceeded the amount of any fees Long Term could earn from “OTC’s investment in [LTCP]” minus transaction costs. Therefore, in stark contradiction to Kuller’s trial testimony, the phrase “OTC’s investment in [LTCP]” could only have been intended to mean OTC’s $10,000,000 of contributions because the actual fees earned (which would have been known by November 1997) from just fifteen months of the “combined” investment of OTC and B & B/UBS (without any inclusion of the four extra fee earning years of the B & B/UBS transaction) totaled approximately $6.2 million, a number far in excess of the costs of the OTC transaction even if the premiums for the legal opinions (approximately $1 million), the cost of the consulting fee arrangement ($1.2 million),
and the $1,250,000 litigation payment to Tur-lington,
and other costs were counted as transaction costs. Thus, because representation/assumption number 12 clearly envisions that the $1,250,000 Turlington litigation payment would have precluded contemporary expectation of and actual material pre-tax profit on “OTC’s investment in [LTCP],” Kuller’s trial testimony that he definitely authored the assumption to also include the B & B/UBS transaction seriously undermines his credibility, both specifically and generally.
Also of no small significance is the absence of any contemporaneous memoriali-zation of this material pre-tax profit analysis Kuller claims to have discussed with Noe.
42
No trace of it appears in Noe’s email of April 14, 1998. The alleged analysis is only implicitly alluded to in the final King & Spalding’ written opinion to the extent the conclusory “representation”/”assumption” that Long Term expected to earn a material pre-tax profit from the OTC transaction required some independent reflection by the opinion’s authors.
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Finally, when Noe was asked on direct examination during questioning related to King & Spalding’s involvement in the OTC transaction whether, as part of Long Term’s due diligence, the potential pretax profit from the OTC contribution was evaluated, he answered in vague terms only that Long Term took into account the fact that it was going to earn fees from the contribution,
see
Tr. [Doc. # 169] at 653:4-654:11, and said nothing about any quantification of those fees against expenses.
Based on the foregoing, the Court concludes that petitioners’ have failed to prove that Kuller’s purported pre-tax profit analysis was ever made and discussed with Noe contemporaneously with the OTC transaction or prior to Long Term’s tax return filing.
9. Long Term and OTC
a. Communication Among Long Term’s Principals
Before approving the OTC transaction, Long Term’s twelve principals discussed it both formally in management meetings and informally amongst themselves. At trial, four principals — Merton, Meriwether, Scholes, and Rosenfeld — testified as to their recollections of those discussions and their related personal concerns. Rosen-feld’s testimony provided the greatest detail.
Merton was chiefly concerned with accurate determination of the fair market value of the high basis preferred stock to be contributed to LTCP, the need for tax expertise to assure that the tax treatment of the stock was as Long Term thought because Merton did not understand how the stock had high basis, and Long Term’s fees to be earned from the contribution as with any other investment. As of the time of the OTC transaction in 1996, Merton did not know that “OTC” stood for Onslow Trading and Commercial LLC but believed it to be merely an acronym for a transaction involving the contribution of preferred stock with high basis to Portfolio in exchange for a partnership interest. Merton discussed with other principals in both formal and informal settings obtaining the tax benefits of the preferred stock for themselves and that the IRS might challenge their claimed tax benefits. Merton never read the opinions of Shearman & Sterling and King
&
Spalding, and did not know what assumptions, if any, were made in those opinions.
Meriwether recalled surprisingly little about almost any aspect of the OTC transaction and any formal or informal discussions about it by the Long Term principals. He had no recollection of dealing with lawyers on the subject, of a loan to OTC, of selling put options to OTC, or of anything about OTC (including what business it carried on, who its principals were, or even what “OTC” stood for). Prior to trial, he was not even aware who B
&
B was or of the UBS/B & B investment. Meriwether did have a recollection of discussing with Scholes a contribution of preferred stock to Long Term with a tax aspect to it, and of one risk management meeting in which the transaction was discussed, regarding which he recalled only that Scholes gave a presentation about the transaction that involved an investment in Portfolio. Meriwether repeatedly emphasized in his testimony that, because of the vigorous debate and consensus management style that characterized Long Term, he is confident that thorough discussion occurred about all aspects of the OTC transaction among the Long Term principals, and that he must therefore have been comfortable with the decision to move forward on it.
Scholes generally claimed that he was involved in a series of discussions with the management committee, the tax committee, and Long Term’s other principals in which he kept them informed about and
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sought advice regarding the OTC transaction. Scholes informed his co-principals that Shearman & Sterling had rendered strong opinions as to the basis of the preferred stock to be contributed, and specifically that the “should” level legal opinions from Shearman & Sterling and King & Spalding provided tax penalty protection.
Rosenfeld recalled two management committee meetings at which the OTC transaction was discussed. The first was a lengthy meeting of several hours, in which Scholes, with the help of a PowerPoint presentation and a written handout,
43
walked the principals through the details of the OTC transaction. The transaction was referred to as the “OTC transaction,” but there is no evidence that the investor was identified beyond being “a UK investor” and “a client of [B & B]”, Tr. [Doc. # 188] at 2298:2,7, or that any specific information about the potential investor (including details about formation, capitalization, and net worth) or its shareholders was provided to or requested by the management committee. Scholes explained the potential for tax benefits from the transaction, specifically the potential for Long Term’s principals to obtain substantial tax benefits from the loss built into the investor’s high basis preferred stock by the investor’s exercise of a put option. The written handout also contained an explanation of these tax benefits. There is no evidence that any other subject matter was included in the handout, and the handout and PowerPoint presentation were the only written materials provided to the LTCM principals. It is not clear whether Scholes discussed the legal opinions of Shearman
&
Sterling and King
&
Spalding at this meeting and there is no credible evidence that Scholes discussed the investment of B & B through UBS.
44
Although the meeting ended without Long Term reaching a decision on the OTC transaction, Rosenfeld was comfortable with it after having heard Scholes’ analysis. The second management committee meeting at which the Long Term principals approved the OTC transaction was short and included discussion of the legal opinions.
During the time frame of the OTC transaction in 1996, Rosenfeld understood that the IRS could challenge the OTC transaction and could impose penalties but believed that penalties would not be appropriate because Long Term had “should” level opinions from Shearman & Sterling.
45
He also understood that, for a transaction to be valid for tax purposes, it had to possess economic substance and that economic substance required a reasonable expectation of profits. He claims however
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that, at the time, he was not thinking about transaction costs, including legal fees paid for the Shearman & Sterling and King & Spalding opinions. He also was not aware of any specific analysis comparing transaction costs with potential fees generated by the OTC investment, and admitted that the legal opinions were obtained in connection with the potential tax benefits and would have been unnecessary had Long Term simply accepted an investment of preferred stock in exchange for a partnership interest.
46
b. Unusual Nature of OTC’s Contributions
Beyond the initial contributions of the founding principals to Portfolio in March 1994, no outside investor other than OTC was ever permitted to contribute non-cash assets in exchange for a partnership interest (even though Long Term’s private placement memorandum acknowledged its discretion to accept non-cash contributions). As a general matter, Long Term was not in this time frame interested in purchasing preferred stock. After OTC’s stock contributions, OTC’s stock was the only U.S. preferred stock held by Portfolio. Before the OTC transaction, Long Term had never sold downside protection puts to any investor. After the transaction, Long Term sold downside put protection only to UBS in connection with the UBS/B
&
B transaction. Similarly, Meri-wether could not recall any other occasions in which Long Term loaned money to an investor to facilitate the investor’s contributions.
The atypical nature of OTC’s preferred stock contributions is underscored by Long Term’s disclosure, prior to the close of OTC’s August 1, 1996 contribution, to certain investors in what Scholes termed “most favored nation letters,” Tr. [Doc. # 182] at 1653:1, that Long Term was about to engage in the OTC transaction. The letters explaining OTC’s contribution in Portfolio were required pursuant to an agreement with the investors that Long Term would not enter into any arrangement with another investor granting more favorable investor rights without first offering the other investors the same rights. The letters, one set dated July 23 and another July 30, 1996, described the OTC transaction as “unique,” informed the recipients that the OTC transaction was considered to be in their best interest because it has the economic effect of increasing the investment of the principals of LTCM in the fund, and explained that it would be unlikely the recipients would be able to structure a similar investment. The July 23, 1996 letters disclose only the OTC transaction, while the letters dated July 30, 1996 disclose both the OTC transaction as well as the B & B/UBS transaction. The letters are all signed by Scholes.
c. Long Term’s and OTC’s Intent Regarding the OTC Transaction
On June 12, 1996, Scholes and Noe met for the first time (and only time prior to the August 1, 1996 contribution of preferred stock) two of the principals of OTC, Sir Geoffrey Leigh and Nicholas Wills.
47
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Koffey had arranged the meeting in London at the request of Scholes and Noe, and was also present. At the meeting, OTC communicated its desire to liquidate any interest it might acquire in LTCP in the near future, stating that they wanted the option to liquidate the investment in a particular period of time and not have to hold the investment for three years as Long Term’s private placement memorandum’s three year lockup provision required. The two put options ultimately purchased by OTC were the solution to this lock up problem. There was also discussion at the meeting about the possibility that the put options to be purchased by OTC be extended into 1998 in the event that Long Term did not need tax losses for the year 1997, but no extension provision was written into the final embodiment of the options.
48
At some point, presumably during this meeting, Scholes informed OTC that he expected an investment in Portfolio to yield an approximately 21% investor return. By the close of the meeting, there was a mutual intent to attempt to close the contribution of OTC’s preferred stock to LTCP by either July 1 or August 1 of 1996.
A draft letter written by Scholes to OTC dated June 18, 1996 and referring to the previous week’s meeting states, “[i]n order to accommodate OTC’s desire to potentially liquidate their investment sometime in the near future, LTCM will grant a Put Option.... ” Govt.’s Ex. 290. Kuller struck the language from the draft before the letter was sent to OTC.
Prior to OTC’s contributions, Noe’s review of OTC’s balance sheet revealed that OTC did not possess sufficient funds to repay the loan from LTCM U.K. without liquidating its interest in LTCP. Under its partnership subscription agreement, OTC was prohibited from pledging its interest to any other lender without the approval of LTCM.
In connection with OTC’s contributions, Long Term also agreed to permit the shareholders of OTC to make individual cash investments in Portfolio up to a combined total of $10,000,000 with a required combined $2,000,000 minimum. The agreement permitted the individual investments as of January 1, 1998 or January 1, 1999. OTC’s principals never exercised their rights under this agreement.
The closing documents accompanying the promissory note for Long Term (U.K.)’s loan of $6,010,451 to OTC in connection with the August 1,1996 transaction and loan of $4,316,842 to OTC in connection with OTC’s November 1,1996 transaction included the minutes from the meetings of OTC’s board of directors at which OTC approved both the August 1 and November 1 contributions to LTCP in exchange for a partnership interest and the facilitating loan from Long Term U.K. The August 1 minutes, among other items, note the date of the meeting as August 1, 1996, and provide, “[OTC] is acquiring the partnership interest with a view to selling the interest at a profit under the put option arrangements set out in 3.3 below.” Pets.’ Ex. 231 at A002403;
see also
Pets.’ Ex. 238.
49
The November 1 minutes similarly
*157
note the date of the meeting, October 30, 1996, and provide identical language regarding OTC’s intent to exercise one of its put options.
See
Pets.’ Ex. 257 at A002466.
d. Scholes’ November 12, 1996 Memorandum
In a memorandum to Long Term’s management committee dated November 12, 1996, eleven days after the second of OTC’s contributions of preferred stock to LTCP, Scholes wrote,
After OTC transfers its investment in LTC partnership to LTCM entities (which ones?), LTCP’s sale of the preferred stock that it holds (when it sells it) will generate $245 million of short-term capital losses and $140 million of long-term capital losses. Not all of the losses need be taken in the same year. We must decide in the near future (1) how to allocate these capital losses; (2) how to “trade” them so that they are held in high-valued hands; and (3) how to plan to be able to enjoy the benefits of the use of these losses for the longest period of time.
If we are careful, most likely we will never have to pay long-term capital gains on the “loan” from the Government.
Value of Losses:
The value of losses depends on how quickly we can use them up. If we establish a mechanism to “reallocate” the losses to the principals who can use them most quickly ..., we maximize their present value to all of us collectively-
With the reallocation, Bruce estimates that we can use about $75 million of capital losses next year. At this rate (and with growth in the Fund) it will take 4 years to use up the tax losses. ($75 million in year 1; $90 million in year 2; $108 million in year 3 and remainder in year 4). Assuming no recapture of losses at a future date, the undis-counted after-tax value of the losses are $170.62 million. This is the anticipated cash flow from the Government (its loan to us) over the next 4 years.
How should LTCM pay those who brought the Tax Losses to Fruition and allocate the expenses of undertaking the trade?
Govt.’s Ex. 320B (emphasis in original).
At trial, although Scholes characterized the language “[ajfter OTC transfers its investment ... to LTCM...” as “inappropriately written,” Tr. [Doc. # 182] at 1731:5-6, he admitted that the language does not anticipate any contingency and conceded that he fully expected OTC to exercise either the liquidity put or downside put.
Scholes’ testimony that his “expectation was that [the $170 million in tax savings] would be paid sometime in the future,”
id.
at 1714: 10-11,
50
and that, while he understood there was “some probability” the taxes would not have to be paid, he “didn’t have any assessment what that probability was,”
id.
at 1714:14-15, does not square with his contemporaneous statement to his partners, “[i]f we are careful, most likely
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we will never have to pay long-term capital gains on the ‘loan’ from the Government.”
51
With respect to the language, “[h]ow should LTCM pay those who brought the Tax Losses to Fruition...Scholes proffered the dubious explanation that it meant how much to compensate Long Term’s principals and Noe for their involvement in bringing about the OTC and B
&
B/UBS transactions. There were no tax losses associated with the B
&
B/UBS transaction, only the OTC transaction. Scholes and other partners ultimately received extra partnership allocations for their work on the OTC transaction, and Scholes’ allocation amounted to several million dollars. The extra allocation exemplified the standard manner in which Long Term generally allocated profits to principals based on the benefits or value they were perceived to have brought to Long Term. Similarly, Noe received $50,000 to $100,000 as an incentive bonus for his work on the OTC transaction. The bonus was paid over a period of years but derived from an arrangement in place at the time of his hiring pursuant to which Long Term had agreed to pay Noe incentive bonuses for work and involvement in structured transactions like the OTC one.
10. The Turlington Problem
Prior to OTC’s contributions, in his initial discussion with Noe or sometime shortly thereafter, Turlington raised the issue of how much Long Term might compensate him for his role in bringing the preferred stock transaction idea and B & B to Long Term. Noe, aware that Turling-ton had a complex fee agreement with B & B, responded that, after the transaction had been completed, Long Term would compensate Turlington with a fair amount in relation to “what the transaction ultimately turned out to be and how much [Turlington] was compensated by B & B.” Tr. [Doc. 174] at 1087:25-1038:1. Noe was aware that Turlington believed a fair amount to be $1.8 million and told Turling-ton that Long Term would consider that amount because of his long standing commitment to Long Term and his knowledge that the partners of Long Term wanted to treat Turlington fairly. Noe also understood that Turlington calculated the $1.8 million based on a percentage of the tax losses that Long Term would obtain from the sale of the preferred stock.
At some point not later than December 1996 (but apparently after OTC’s November 1, 1996 contribution), Turlington made a claim for fees against B & B. While unclear from the trial record, Long Term appears to have been also included in the fee dispute by no later than May 1997 as evidenced by a draft letter dated May 9, 1997 written by Jim Rickards, Long Term’s general counsel, to Turlington:
It was a pleasure seeing you in New York for dinner recently....
Since we met, I have conducted further interviews and inquiries regarding the basis on which your fee should be computed for demonstrating a valuable idea to Babcock and ourselves as to which the investment funds we manage may be the ultimate beneficiaries. It is surprising that this issue could be in dispute when the bare facts are largely agreed. It may be helpful to recite some of those facts before explaining our position on the fee issue.
... Shortly after presenting your idea to us, you introduced Babcock as a party
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which might be able to facilitate the implementation of this idea.... All of the parties ... recognized ... actual and potential conflicts .... It was at this point that all parties agreed that your prospective relationship in this transaction would be solely with Bab-cock and that we would independently obtain whatever advisers we needed, at our sole expense, in addition to dedicating internal resources in order to consummate the suggested transaction.
An obvious and explicitly agreed corollary of that decision was that Babcock would be the sole source of all fees to be paid to you for any residting transactions.
This decision was without prejudice to what those fees might be. You were free to negotiate ... any appropriate fee structure you wished with Babcock presumably on an “all in” basis with reference to benefits derived by our funds. We were not unaffected by this as, to the extent we independently agreed to pay fees to Babcock, they would obviously be looking for some net between what they might receive from us and what they paid to you for their value added; therefore, the higher the fee they paid to you, the more we might logically expect to be paying to them. However, this state of affairs is a far cry from any notion of “two fees” payable separately by us and Babcock with respect to a single course of dealing....
At our dinner, we spent some time discussing your conversations with [Noe] on the subject of fees. These discussions were entirely consistent with the understandings described above in that (á) we highly value our prior and prospective relationship with you and therefore wanted to be assured you were being compensated fairly by- Babcock, (b) we had critical information which would be needed by Babcock to compute their fee payable to you and were quite happy to share this information with you in the interests of facilitating your discussions with them and (c) to the extent that Babcock looked to our fee to pay you, we were in a position to ‘top up’ our fee to them to enable them to pay you more than would otherwise be the case. We are greatly distressed that our good faith efforts to use our good offices to facilitate your dealings with Babcock have been misconstrued as a separate “fee” negotiation directly with you.
... We are firm in our consistently held view that your fees for the transactions discussed herein will be paid exclusively by Babcock and that such fees will compensate you for the benefit derived by ■ our funds. For our part, we have fully and fairly compensated Babcock for these investor benefits and respectfully urge you to continue your discussions with Babcock as your source of compensation.
Govt.’s Ex. 331. While the letter is unsigned and marked “draft JGR letterhead,” the letter was delivered to B
&
B from Long Term, presumably as a part of their joint negotiation with Turlington over the amount of his fee.
It is ndt clear from Turlington’s testimony whether his “claim for fees” was formal or informal but at a minimum the threat of litigation can be inferred from the fact that shortly after the claim was raised and into 1997, Turlington’s lawyers were involved in negotiating with Long Term and B & B over what Turlington’s fee would be. Long Term and B & B ultimately jointly contributed to a settlement payment of $1.8 million to Turlington’s law firm for his role in introducing B & B to Long Term and his partnership tax idea regarding the preferred stock. B & B contributed $550,000 and Long-Term contributed $1.25 million to the settlement. B & B only made its share of the payment because Long Term asked it to, which B & B
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viewed as a cost of its ongoing relationship with Long Term.
During the period of the fee dispute, B & B and Long Term discussed with Tur-lington the possibility of his law firm obtaining a piece of the call option B & B had acquired from UBS, indicating, oddly, to Turlington that they did not want to provide Turlington information on the call option possibility in writing. Furthermore, in negotiating the fee with Turlington, B & B informed Turlington that it knew other individuals or entities with high basis preferred stock and that it would undertake to explain Turlington’s idea to them for the purpose of earning additional fees for B
&
B and additional compensation for Turling-ton. At trial, Turlington plausibly conjectured that such offer was an attempt by B & B to negotiate down the fee owed in connection with the Long Term deal.
11. Petitioner’s Expert: Frank J. Fa-bozzi
Petitioners offered Dr. Frank J. Faboz-zi, an expert in economics, finance, structured finance, and leveraged transactions with an extensive academic and publishing background, to opine on OTC’s risk return profile in the CHIPS and TRIPS transactions, OTC’s risk return profile with respect to its contributions to LTCP and subsequent sale of its partnership interest to LTCM, and Long Term’s potential benefit from both the OTC contributions and B & B’s investment via UBS. The Court is here unconcerned with Fabozzi’s first opinion.
With respect to OTC’s contributions, Fa-bozzi opined that OTC risked losing the equity it had in its preferred stock, OTC stood to benefit from appreciation in value of its partnership interest, and Long Term’s potential quantitative benefit could be found in the fees it could earn on OTC’s contributions. Fabozzi calculated OTC’s equity in the contributed preferred stock at $1,012 million, which was the approximate difference between the amount of the loans from Long Term UK secured by OTC’s partnership interest ($9,327,293) and the amount of OTC’s total investment ($10,340,000). Fabozzi specified that, notwithstanding a hypothetical exercise by OTC of
its
downside put, OTC risked losing the majority of the equity in its investment because the $10,340,000 received from Long Term upon exercise would be used to pay off the approximately $9.3 million loan from Long Term U.K. plus seven percent interest, leaving approximately $284,000 for OTC.
52
Subtracting the cost of the downside put options, $121,000, Fabozzi calculated the amount of equity remaining in OTC’s investment at $163,000 in the event OTC had to exercise its downside put. In addition, Fabozzi opined that OTC was at risk of losing all its equity as a result of “counter party risk,” the chance that Long Term would be unable to perform on the exercise of the downside put.
Fabozzi testified that the quantitative allure for Long Term of OTC’s contributions and B
&
B’s investment via UBS would have been the potential to earn management and incentive fees on the investments. Fabozzi had no opinion on whether the OTC transaction and the UBS/B
&
B transaction should be considered one package, but had performed calculations both ways. Regarding the OTC transaction, Fabozzi opined that Long Term would receive a two percent management fee from the $10,340,000 plus an incentive fee calculated as twenty-five percent of the appreciation on the investment
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after subtracting the management fee.
53
Fabozzi provided mathematical computations on how the fee earnings might work in practice. For example, he calculated that, if one assumed a 21.55% rate of return and that OTC would exercise either its liquidity or downside put, Long Term stood to earn combined fees of $835,654 on OTC’s investment.
54
Similarly, at a 21.55% rate of return over the five years of B
&
B’s investment via UBS, Fabozzi calculated that Long Term stood to earn fees of $17,622,812.
55
While Fabozzi’s hypothetical rates of return were derived from historical rates of return for Portfolio, Fabozzi repeatedly emphasized throughout his testimony that he was not opining on the reasonableness of any particular rate of return or on whether it would have been reasonable to believe that historical performance would continue, acknowledging that no one can accurately predict a rate of return into the future. On cross examination, he stated that he was aware that, at the time of OTC’s contributions, Long Term was generally restricted to new investors and opined that this situation was likely due to Long Term having run out of investment strategies. If that wére the case, he continued, the addition of investor capital would only serve to dilute the rate of return with respect to any particular investment, thus driving down the expected incentive fee return to Long Term from any one investor.
Also on cross-examination, Fabozzi acknowledged that, assuming Long Term and Long Term U.K. were under common ownership, Portfolio would earn a 21% rate of return for investors, and Long Term U.K. already possessed the approximately $9.3 million it loaned to OTC at 7% per annum to facilitate OTC’s contributions, there would be an opportunity cost to Long Term for participating in the OTC transaction of 14% of that investor return because, instead of subjecting the $9.3 million loan to the risk of Portfolio by securing it with OTC’s partnership interests, Long Term could have invested the $9.3 million into its own capital account in Portfolio thereby entitling itself to all 21% of expected investor return.
12. Scholes’ Economic Analysis
Scholes claims that, while he did not perform an independent economic analysis of the TRIPS and CHIPS transactions, he did analyze the economics of the OTC transaction prior to OTC’s contributions and concluded that Long Term could make a good return and profit by virtue of the management and incentive fees that would inure to Long Term from OTC’s contributions to LTCP and B & B’s investment in Long Term via UBS. Scholes testified to the specifics of his analysis as follows: in 1996, he expected Long Term to obtain a 21% return after .fees on both OTC’s and UBS’s contributions, generating approximately 9%.of the overall contributions as management and incentive fees for Long Term, and, with modifications for projected investment growth, calculated anticipated fees of $34 million from the UBS/B & B investment alone over the course of its expected five year period. Assuming an “overwhelming probability,” Tr. [Doc.
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# 184] at 1836:24, that B & B would exercise the call options it purchased from UBS, Scholes added the $4 million Long Term received in option premiums. He also testified that he thought the fee income from OTC’s and B & B’s investments could be invested back into Portfolio to generate more fee income for Long Term’s principals and that profits would result from the consulting agreement with B & B. Scholes claims he excluded the bonus allocation he received for his work in bringing the OTC transaction to Long Term because the fees being generated from the B & B investment coupled with the partners’ extra income from both OTC’s and B & B’s investments diminished the significance of the bonus, particularly because the bonus allocation included not only cash but also an increased stake in Portfolio.
Scholes admitted that, viewing the OTC transaction on its own and apart from the B & B investment “then obviously the profits look very marginal, if any, if you allocate all of the cost to the OTC transaction.” Tr. [Doc. #184] at 1854:10-14.
56
He repeatedly claimed that his economic analysis never considered such an allocation but instead only allocated expenses against the combined expected fees generated by both the OTC and B & B investments because, in light of Portfolio having been “closed” and many investment banks having been turned away as potential investors, the other Long Term principals would not have permitted B & B to invest without OTC’s contributions of preferred stock. Scholes’ allocation rationale appears more likely a contrivance to show expected profitability and objective eeo-nomic substance than a serious economic analysis. He acknowledged that the B
&
B/UBS transaction was “a very standard investment,” Tr. [Doc. # 184] at 1853:13, that the King & Spalding and Shearman
&
Sterling legal opinions do not opine at all on the B & B investment, and that, without OTC’s stock contributions, an independent relationship with B & B was “potentially possible.” Tr. [Doc. # 182] at 1772:10. There is thus no practical reason for any of the costs for the legal opinions to be allocated to the B & B investment. Moreover, Scholes’ illogical insistence that the two transactions be combined for objective economic profit loss analysis had the secondary effect of illuminating Long Term’s business purpose for the OTC transaction. Scholes knew B & B would not have been permitted to invest in Long Term without OTC’s stock contributions and that Portfolio was open only to strategic investors (i.e. investors bringing value in excess of fees) during this time frame, and admitted that he saw no value to any continued relationship with OTC. The inescapable conclusion is that Long Term’s goal in permitting both investments was to obtain the tax benefits inherent in OTC’s preferred stock. Scholes in part explicitly acknowledged this goal when he testified that some of the Long Term principals viewed the sole value brought by OTC and B & B as anticipated tax benefits.
57
At bottom, Scholes’ claimed belief that the IRS would evaluate the economic substance of the OTC transaction in combination with the B & B investment was because Long Term declared it so: “it was LTCM’s decision to take in the investment
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from both OTC and B
&
B.” Tr. [Doc. # 184] at 1853:18-21.
13. Government’s Expert: Joseph Stiglitz
The Government offered Dr. Joseph Sti-glitz, a professor of economics and finance in the Graduate School of Business at Columbia University and a Nobel Prize winner in 2001 for his work on the economics of information,
58
to opine on whether real economic value was created in the process of the CHIPS, TRIPS, or OTC/Long Term/UBS/B
&
B transactions. The Court examines only Dr. Stiglitz’ views on whether there was any economic explanation for the OTC/Long Term/UBS/B
&
B transactions apart from the tax benefits.
Dr. Stiglitz testified about potential hidden transaction costs in connection with OTC’s contributions to LTCP. He started with the premise that a legitimate tax deduction, for example deductions associated with true leases, have an economic value that is assigned by the market and for which market actors ought to pay. In attempting therefore to determine why Long Term ostensibly did not have to pay compensation for the tax benefits obtained from OTC, Dr. Stiglitz came up with two theories: either the market considered the tax deduction so likely to be questioned and to invite penalties that it assigned á value of $0 to it or the market considered the tax deduction, although risky, to have expected value
59
notwithstanding the potential of future challenge and thus did assign a value to it. He pointed out that, to avoid undermining the economics of the OTC transaction, Long Term might not want to disclose how much it paid for it and thus would have incentive to seek out forms of hidden compensation. Dr. Sti-glitz identified a variety of opportunities for hidden compensation, including Long Term’s consulting arrangement with B & B to the extent the $1.2 million price of that arrangement to Long Term exceeded the value of consulting services rendered under it.
60
However, Dr. Stiglitz also testified that it is difficult to detect hidden fees, the existence of those fees requires inquiry into the incentives of the actors, and ultimately it is difficult to make a definitive judgment about them. Ultimately, with respect to Long Term, Dr. Stiglitz concluded, “.. .there was obviously the incentive, there was the opportunity, there were the forms, but ... because it is so difficult to make a definitive judgment about whether that, in fact, occurred, I don’t want to make a statement on it.” Tr. [Doc. # 194] at 2724:11-16.
Dr. Stiglitz opined that Long Term could not have earned a profit from the OTC transaction from the fee structure in place at the time of the contributions. Assuming reasonable rates of return, Dr. Sti-glitz concluded that the transaction costs associated with generating fees from the OTC transaction caused a negative net return. He included among the transaction costs legal fees for the opinion letters from Shearman & Sterling and the bonus
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es paid to Scholes and Noe. He further concluded that, because OTC was permitted to invest in Long Term using Long Term U.K.’s loan on which Long Term bore all downside risk by virtue of OTC’s downside put option, Long Term was economically worse off than if Long Term made the identical investment on its own behalf because, although bearing all downside risk, Long Term was limited in participating on the upside to its incentive fee of 25% of any profit on OTC’s investment. If Long Term had invested its own money directly, it would bear all downside risk hut would also have been entitled to all potential upside. Dr. Stiglitz concluded that a rational actor would not have selected the route Long Term selected because such route, absent tax benefits, forfeited potential profit without any corresponding decrease in risk.
In addition, Dr. Stiglitz believed that Long Term itself had tacitly admitted by closing Portfolio that the OTC transaction was, from a fee perspective, not a good economic deal because it meant that Long Term “had decided that the fees they got from additional contributions were not worth the additional contributions.” Tr. [Doc. #194] at 2727:12-14. Because investment opportunities are limited by a fund’s investment strategies and management capabilities such that a fund’s investments are subject to diminishing returns at the point at which additional contributions dilute the rate of return, Stiglitz explained that closing a fund represents a business judgment that fees derived from additional contributions are not worth the dilution the extra contributions cause to the fund’s rate of return. Stiglitz concluded that Long Term had thus already rejected the fee argument it offered at trial — the OTC deal was economically viable because of the fees it would produce for Long Term — “when they were looking at other cases, apart from the tax concerns.” Tr. [Doc. # 194] at 2728:6-7.
Finally, and similar to the economic problem associated with the Long Term U.K. loan, Dr. Stiglitz concluded the UBS/B & B transaction was a bad economic deal for Long Term because Long Term similarly subjected itself to the downside associated with UBS’ investment of approximately $50,000,000 in Portfolio while limiting its participation in the upside of the investment to an incentive fee once B & B exercised its call options rather than seeking all upside potential as commensurate with its risk. He explained the UBS/B & B transaction, including UBS’ put options and B & B’s call options, was basically equivalent to a loan to Long Term with respect to which all credit risk was borne by Long Term, because, if the investment sours, LTCM must pay UBS the strike price upon UBS’ exercise of its put options. Thus, as a loan, “LTCM could have taken that loan and put it in its portfolio,” Tr. [Doc. # 194] at 2729:20-21, thereby entitling itself to all upside potential experienced by the investment. Instead, even assuming historical rates of return to Portfolio and not addressing the issue of diminishing returns resulting from limited investment strategies, Long Term gave away by contract seventy-five percent of the upside potential to B & B in a transaction that Dr. Stiglitz summed up as “one of these examples where you, at least as I read it, deliberately try to complicate things so you can obscure what was going on, because there was a UBS investment but also a call and a put. And when you look at that whole package, that’s equivalent to a loan.... ” Tr. [Doc. # 194] at 2728:16-21. Thus, in Dr. Stiglitz’s view, “the fees did not provide adequate economic explanation [for the UBS/B
&
B transaction].... there was no real economic explanation for this transaction apart from the taxes.” Tr. [Doc. # 194] at 2730:9-13.
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The Court found the portion of Dr. Sti-glitz’s opinions summarized above credible and persuasive when viewed in light of the facts of the case. The Court found petitioners’ attempt to discredit him, particularly the emphasis on his alleged personal bias against Long Term, unpersuasive.
14. IRS’ Audit and Long Term’s Response
The IRS commenced an audit of Long Terms tax returns for the 1996 and 1997 tax years in 1999. Rosenfeld was in charge of working with Long Term’s lawyers and accountants in responding to information requests from the IRS during the audit and examination of Long Term with respect to the OTC transaction. Ro-senfeld testified that, during the audit and examination, Long Term provided substantiation for the tax basis in the preferred stock acquired from OTC, including documents and the legal opinions of Shearman
&
Sterling and King & Spalding, and Long Term responded as quickly and accurately as possible to all IRS’ information document requests and summons. Rosenfeld clarified that the Shearman
&
Sterling opinion was provided early on in the process and the King & Spalding opinion directly to the Department of Justice later in the process. Rosenfeld did testify that he thought the legal opinions were withheld after IRS requests because they were considered privileged documents, and that Long Term’s lawyers explained the withholding to the IRS. He also recalled that the Shearman & Sterling opinion was disclosed to the IRS after it was determined that it was not a privileged document. Rosenfeld also testified that he believed Long Term maintained all books and records related to items under audit on its 1996 and 1997 federal income tax returns.
On cross examination, while the Government pressed Rosenfeld regarding failures to respond to official requests during the IRS audit, including requests for legal opinions and lists of transaction costs associated with the OTC transaction, Rosenfeld almost uniformly answered that he was not aware of any shortcomings and the Government offered no evidence to support the embedded assertions of delinquent responses- in its questions to Rosenfeld. However, Rosenfeld did admit that Seholes’ PowerPoint presentation and accompanying written handout were never provided to the IRS because, he testified, Long Term was unable to find them.
Rosenfeld testified that, when Long Term filed its petitions for adjustment on July 9, 2001, it had a negative net worth of approximately $60,000,000. In rough outline, the claim of negative net worth derived from the following assertions: in September 1998, when a consortium of banks took over Long Term, Long Term held directly or indirectly in Portfolio $100,000,000, owed $200,000,000 in loans (predominantly from banks), and subsequently repaid $40,000,000 earned through fees. Rosenfeld, however, admitted that, in 1998, Long Term was entitled to $104,000,000 in deferred fees, which were invested in Portfolio, and that the consortium of banks required those fees to be liquidated to pay down Long Term’s debts, which, according to Rosenfeld, included some of the $200,000,000 in loans.
III. Discussion
A. Burden of Proof
. Taxpayers generally bear the burden of proof when litigating their tax liabilities. See
e.g., United States v. Janis,
428 U.S. 433, 440 , 96 S.Ct. 3021 , 49 L.Ed.2d 1046 (1976);
Caplin v. United States,
718 F.2d 544, 549 (2d Cir.1983)(“In a tax refund suit, the burden of proof is on the taxpayer to prove an overpayment of tax.”). Congressional enactment in 1998 of 26 U.S.C. § 7491 , however, statutorily altered the traditional analysis, permitting taxpayers
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to shift the burden of proof to the Government in certain circumstances. In pertinent part, § 7491(a) provides,
(a) Burden shifts where taxpayer produces credible evidence.—
(1) General rule. — If, in any court proceeding, a taxpayer introduces credible evidence with respect to any factual issue relevant to ascertaining the liability of the taxpayer for any tax imposed by subtitle A or B, the Secretary shall have the burden of proof with respect to such issue.
(2) Limitations. — Paragraph (1) shall apply with respect to an issue only if—
(A) the taxpayer has complied with the requirements under this title to substantiate any item;
(B) the taxpayer has maintained all records required under this title and has cooperated with reasonable requests by the Secret

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Source: Frix Law Library, https://www.frixlaw.com/law-library/cases/2314334. Public record. Not legal advice.