Opinion

BCP Trading and Investments, LLC v. Cmsnr. IRS

  • 991 F.3d 1253
Court
Court of Appeals for the D.C. Circuit
Filed
Mar 23, 2021
Status
Published
Cited by
3 cases
Authority
More cited than 52.1%

affirming the Tax Court’s decision the BCP Trading & Investments, LLC partnership was 9 a sham

How later courts described this case

  • affirming the Tax Court’s decision the BCP Trading & Investments, LLC partnership was 9 a sham

Written by the judges who cited it.

The opinion

United States Court of Appeals

FOR THE DISTRICT OF COLUMBIA CIRCUIT

Argued November 18, 2020 Decided March 23, 2021

No. 19-1068

BCP TRADING AND INVESTMENTS, LLC, ET AL.,

APPELLANTS

v.

COMMISSIONER OF INTERNAL REVENUE,

APPELLEE

VIRGINIA SIMPSON,

APPELLANT

Consolidated with 19-1072, 19-1098, 19-1099, 19-1122,

19-1123

Appeals from the United States Tax Court

Jeremy C. Marwell argued the cause for appellants

Kalkhoven-Pettit Partnerships. George M. Clarke III argued

the cause for appellants Esrey-LeMay Partnerships. With them

on the briefs were Mireille R. Oldak, Vivek A. Patel, Robert E.

McKenzie, Kathleen M. Lach, Matthew X. Etchemendy,

Michael L. Charlson, and David C. Cole.

Virginia Simpson, pro se, filed the brief for appellant

Virginia Simpson.

2

Jennifer M. Rubin, Attorney, U.S. Department of Justice,

argued the cause for appellee. With her on the brief was Joan

I. Oppenheimer, Attorney.

Before: SRINIVASAN, Chief Judge, HENDERSON and

WALKER, Circuit Judges.

Opinion for the Court filed by Circuit Judge HENDERSON.

KAREN LECRAFT HENDERSON, Circuit Judge: In January

2008, the Commissioner of the Internal Revenue Service

(Commissioner) issued tax adjustments to the partnership of

BCP Trading & Investments, LLC (BCP) for tax years 2000

and 2001. Members of BCP—themselves limited

partnerships—challenged the adjustments, arguing they were

untimely and that the Commissioner mistakenly determined

that the investment partnership was a sham. The United States

Tax Court found the adjustments timely because the three-year

statute of limitations for the adjustments was extended by the

partnership and its members and those extensions, contrary to

BCP’s members’ challenges, were consistent with fiduciary

and contract principles. The Tax Court upheld the

Commissioner’s adjustments, declaring the partnership a sham

for tax purposes. Virginia Simpson, a non-participating party,

moved to intervene after the Tax Court issued its memorandum

opinion and findings of fact but before it issued its final

decisions. The Tax Court denied her intervention in a separate

order.

Before us is a consolidated appeal of the Tax Court’s

opinion and final decisions regarding the Commissioner’s

adjustments issued to BCP as well as its order denying

intervention. The Tax Court applied correct legal precedent and

committed no clear error in its findings upholding the

3

Commissioner’s tax adjustments. Nor did the Tax Court abuse

its discretion in denying Simpson’s intervention. Accordingly,

we affirm.

I. BACKGROUND1

As with many cases arising from the Tax Court, “[t]he

hardest aspect of this case is simply getting a handle on the

facts.” ASA Investerings P’ship v. Comm’r, 201 F.3d 505, 506

(D.C. Cir. 2000). Because a chronological retelling of the story

may confuse more than enlighten, we start with the actors

involved and then address the intricacies of the transaction at

issue.

A. The Actors

The hub around which all of the actors revolve is BCP.

BCP was a partnership and during its brief life had 39

members. At BCP’s helm was its managing member, a limited

liability company, Bolton Capital Planning, LLC (Bolton

Capital). Charles Bolton owned and operated Bolton Capital

and Belle Six worked for Bolton Capital. Six, Bolton’s partner

in crime,2 was a former employee of the global accounting firm

Ernst & Young (E&Y). BCP’s other 38 members (“client

members”) were limited liability companies and limited

partnerships and all were clients of E&Y. Two groups of client

members—all limited partnerships—are relevant to this

appeal: (1) KP1, KP2 and PCMG XII and (2) WTETP and

PCMG VI.

1

We address the relevant facts and law of Simpson’s failed

intervention in Part III, infra at 31. All facts come from the

stipulations and other evidence before the Tax Court.

2

Six and Bolton both pleaded guilty to tax crimes in connection

with their tax shelter activities.

4

Kevin Kalkhoven and Dan Pettit were limited partners in

the KP1, KP2 and PCMG XII limited partnerships. They were

both executives at JDS Uniphase Corporation and they hired

E&Y in the 1990s to manage their tax matters. Their

relationship with E&Y grew from tax matters to include much

of their personal financial affairs. Jim Cox of E&Y managed

both Kalkhoven’s and Pettit’s business matters.

William Esrey was a limited partner in WTETP and

Ronald LeMay was a limited partner in PCMG VI. Esrey and

LeMay were executives at Sprint Corporation; Sprint required

them to use E&Y to prepare their tax returns and E&Y prepared

their tax returns beginning in the 1980s. Over the years both

Esrey’s and LeMay’s relationship with E&Y evolved from tax

preparation to estate, financial and tax planning—Mike Carr of

E&Y served as Esrey’s and LeMay’s point of contact.

B. The Actors’ Business Relationships

In 1999 Six left E&Y to join The Private Capital

Management Group (TPCMG) to help TPCMG market an

E&Y-promoted financial transaction called a Contingent

Deferred Swap (CDS). CDS transactions defer taxes on

ordinary income by one year and transform the ordinary

income into capital gains, which are taxed at a lower rate than

ordinary income. Through their respective limited

partnerships, Kalkhoven, Pettit, Esrey and LeMay (Taxpayers)

engaged in CDS transactions with TPCMG in 1999. In late

1999 or early 2000, TPCMG transferred the CDS business to

Bolton. Six joined Bolton to continue to market the CDS

transactions and act as liaison between Bolton and E&Y.

To offset the capital gains taxes generated from the CDS

transactions, E&Y created a new transaction—the transaction

at issue in this case—known as the CDS Add-On or CDS Plus

(Add-On). E&Y’s Carr and Bolton Capital’s Six described the

5

Add-On to Esrey and LeMay and both Esrey and LeMay

decided to participate. E&Y and Bolton Capital’s Six also

presented the Add-On to Kalkhoven and Pettit and both

decided to participate. In May 2000, on E&Y’s advice, Bolton

Capital formed BCP to execute the Add-On. Between 2000 and

2001 BCP client members—including the Taxpayers’ limited

partnerships—engaged in the E&Y-designed Add-On.

Under the United States Tax Code, partnerships do not pay

federal income tax. I.R.C. § 701.3 Instead, partnerships file an

annual information return reporting each partner’s share of

income, gain, loss, deductions and credits. Id. §§ 702, 6031.

The partners report their individual shares of income, gain,

loss, deduction or credit on their individual federal income tax

returns and taxes are assessed against the partners individually.

Id. §§ 701, 702, 704. If the IRS disagrees with a partnership’s

reporting, it issues a Final Partnership Administrative

Adjustment (FPAA) before imposing tax assessments against

the individual partners. Id. §§ 6223(a)(2), (d)(2), 6225(a). The

IRS must assess tax attributable to partnership items 4 within

three years of the date the partnership return is filed or the last

date for filing the return, whichever is later. Id. § 6229(a). If

the three-year period has not yet expired, the IRS may seek to

extend it, using either of two “statute extensions.” Id.

3

Unless otherwise noted, references to the Internal Revenue

Code are those in effect at the time relevant to these cases.

4

A “partnership item” is “any item required to be taken into

account for the partnership’s taxable year under any provision of [the

Internal Revenue Code’s Income Tax subtitle] to the extent

regulations prescribed by the Secretary provide that, for purposes of

this subtitle, such item is more appropriately determined at the

partnership level than at the partner level.” I.R.C. § 6231(a)(3). “[A]

determination that a partnership lacks economic substance is an

adjustment to a partnership item.” United States v. Woods, 571 U.S.

31, 39 (2013).

6

§ 6229(b). The IRS may obtain an extension from the partner

whose individual tax return may be affected. Id.

§ 6229(b)(1)(A). Alternatively, the IRS may ask the tax matters

partner (TMP) of the partnership to consent to an extension to

allow the IRS to assess any taxes attributable to partnership

items of all partners. Id. § 6229(b)(1)(B).

The IRS obtained a timely partnership extension for tax

year 2000 from Bolton, BCP’s TMP, on January 6, 2004

(Partnership Extension). Bolton subsequently executed eight

more partnership extensions—the last on April 2, 2007—

extending the liability period for tax years 2000 and 2001

through June 30, 2008. The IRS also obtained timely individual

extensions from Kalkhoven, Pettit, Esrey and LeMay

(Individual Extensions). As relevant here, Pettit and Kalkhoven

signed Individual Extensions for tax year 2000 on November

17 and November 20, 2003, respectively, and both again did so

on September 27, 2004. Esrey and LeMay signed Individual

Extensions for tax year 2000 on December 4, 2003 and January

26, 2004, respectively. The Taxpayers continued to sign

individual extensions, extending their tax liability for tax years

2000 and 2001 through at least December 31, 2008.

While the IRS sought the Partnership and Individual

Extensions, E&Y was actively advising BCP and the

Taxpayers and representing the Taxpayers before the IRS.

E&Y’s Cox advised Kalkhoven and Pettit to consent to the

Individual Extensions and did not discuss any extension

downside with them. Similarly, E&Y’s Carr advised Esrey and

LeMay to authorize individual extensions. E&Y also advised

BCP to sign the Partnership Extension. Six wrote to the

Taxpayers, informing them that Bolton Capital planned to sign

the Partnership Extension “[b]ased on Ernst & Young’s . . .

recommendation . . . unless we hear otherwise from you.” Joint

Appendix (J.A.) 725.

7

Around the same time E&Y was the subject of several civil

and criminal investigations. As a brief overview, by 2002 E&Y

knew the IRS was auditing CDS transactions. In March 2002,

E&Y became the subject of an IRS “civil promoter” audit to

determine if E&Y had failed to disclose tax shelters.5 That

audit was settled in July 2003. In May 2004, a grand jury

investigation began to examine E&Y’s tax shelters.

On January 31, 2008, the IRS issued FPAAs against BCP

for tax years 2000 and 2001. In the FPAAs, the IRS determined

BCP was a “sham” and should be disregarded for tax purposes.

The Taxpayers, through their partnerships, challenged the

FPAAs in Tax Court. First, the Taxpayers argued the FPAAs

for tax year 2000 were untimely because the Individual

Extensions and Partnership Extension upon which any

subsequent tax year 2000 extensions rested were voidable

under agency and contract law. The Taxpayers also argued that

BCP was a bona fide partnership because it had a valid business

purpose. In August 2013 Tax Court Judge Diane Kroupa

presided over the trial but Judge Kroupa retired after trial and

the case was reassigned to Tax Court Judge Mark Holmes. In

August 2017 the Tax Court issued its findings of fact and

memorandum opinion, concluding the extensions were valid

and that BCP “was created to carry out a tax-avoidance

scheme” and should therefore be “disregard[ed]” for tax

purposes. BCP Trading & Invs., LLC v. Comm’r, 114 T.C.M.

(CCH) 151, 2017 WL 3394123, at *21 (2017). On February 6,

2019, the Tax Court issued its order denying intervention. J.A.

5

I.R.C. §§ 6111 and 6112 require a tax shelter organizer to

register a qualifying tax shelter with the IRS and provide certain

information regarding it. I.R.C. §§ 6707 and 6708 impose penalties

on anyone who fails to register or provide the applicable information

on a qualifying tax shelter.

8

2482. And on February 7, 2019, it issued two decisions

implementing its August 2017 opinion. J.A. 2488–89.

C. The Challenged Add-On6

The Add-On consisted of several intermediate steps. To

begin, BCP client members purchased 132 option pairs

between July 19 and August 11, 2000. Both options in the pair

were digital options. A digital option is a type of option

contract that pays the option holder a fixed payout if the

underlying asset’s price equals or exceeds a predetermined

price (strike price) by a predetermined expiration date.7 If the

underlying asset’s price does not reach the strike price by the

expiration date, the option expires worthless. Here, the

underlying asset in each digital option pair was a foreign

currency.

As a “European-style” option, the underlying asset’s price

is evaluated to determine whether an option pays out or expires

worthless only on the predetermined expiration date and time.

The asset’s price at expiration is the spot price or spot rate.

Accordingly, on the option’s expiration date and time, the spot

price is compared to the strike price. If the spot price meets or

exceeds the strike price, the option pays out but if the spot price

does not meet or exceed the strike price, the option expires

worthless. All options began “out of the money”—at the time

each option was purchased, the currency price did not already

6

Our description of the Add-On follows the Commissioner’s

brief, see Appellee’s Br. at 4–26, and the Tax Court’s opinion, see

BCP, 2017 WL 3394123, at *3–*6.

7

Here, we describe the 124 option pairs that required positive

price movement relative to the strike price, not the eight option pairs

that required negative price movement.

9

exceed the strike price but upward price movement was

necessary for them to pay out and not expire worthless.

Each option pair included an option which the client

member bought from Refco Capital Markets (Refco) (referred

to as the “long” option) and an option which the client member

sold to Refco (referred to as the “short” option). The long and

short options in each pair had a one “percentage in point” (pip)

difference in strike price. A pip is the smallest pricing

increment in foreign exchange markets and for many

currencies it is 1/100th of a cent. With a spread only one pip

wide, typically the spot prices fall short of both strike prices

(and both options in the pair expire worthless) or exceed both

strike prices (and both options in the pair pay out). As

envisioned, if the spot price exceeded both strike prices, Refco

owed the predetermined payout on the long option to the client

member and the client member owed the predetermined payout

on the short option to Refco. But the payout to the client

member on the long option always exceeded the payout to

Refco on the short option; Refco then paid the client member

the difference between the two. Accordingly, if both options

expired “in the money” with the spot price above the strike

price, only the client member (not Refco) received the net

payout.

How the Add-On functioned may be best understood by

one transaction. PCMG XII bought and sold into an option pair

with Refco on July 31, 2000. Both the long and short options

in the pair expired on November 30, 2000. The option pair’s

underlying asset was the reference exchange rate of Canadian

Dollars (CAD) per United States Dollar (USD). The long

option’s strike price was an exchange rate of 1.5075 and the

short option’s strike price was an exchange rate of 1.5076. If

the spot price (i.e., the reference exchange rate on November

30, 2000) equaled or exceeded the long option’s strike price of

10

1.5075, Refco paid PCMG XII $170 million. On the other

hand, if the spot rate equaled or exceeded the short option’s

strike price of 1.5076, PCMG XII paid Refco $169.5 million.

If the spot rate was above both strike prices, PCMG XII

received a net payment of $500,000. If the spot price was below

both strike prices, both options expired worthless.

If the spot rate landed within the one pip spread—the

“sweet spot”—client members received a “lottery payoff”

because Refco had to pay out on the long option but the client

members did not have to pay out on the short option. In our

example, if the spot rate had landed at 1.5075 or between

1.5075 and 1.5076, Refco would have paid PCMG XII $170

million but PCMG XII would not have paid Refco $169.5

million. The likelihood of the spot rate falling within the one

pip spread was miniscule. Not only was the spread just one pip

wide but the option pairs were custom. A custom option is not

listed or traded on any exchange. Accordingly, there are

multiple different expiration-day spot prices for the same

currency depending on which bank or broker Refco dealt with.

Refco had the discretion to choose between those spot prices

for settling the option pairs, so long as it acted “in good faith

and in a commercially reasonable manner.” J.A. 90. Refco had

both an incentive not to let an option pair hit the sweet spot and

the discretion to keep it from doing so.8

8

Refco’s incentive to enter the option pair contracts came from

the option premiums. The client members paid a purchase premium

to Refco on each long option and Refco paid a sale premium to the

client members on each short option. The purchase premium

exceeded the sale premium and the client members paid Refco the

net difference between the premiums (total premium). In our

example, PCMG XII’s purchase premium to Refco was $51,000,000.

Refco’s sale premium to PCMG XII was $50,750,787. Accordingly,

11

Between July 31 and August 11, 2000, the client members

contributed the option pairs to BCP—transferring the assets

from the client member’s ownership to BCP’s. In return, each

client member was credited with a BCP capital account equal

to the amount of the total premium paid on its contributed

options. Subsequently, every option pair either expired

worthless or was sold before its expiration date for less than the

total premium paid. Accordingly, BCP’s portfolio appeared to

lose significant value.

E&Y advised the client members to terminate their interest

in BCP in the year they chose to claim losses. All client

members, including the Taxpayers’ respective partnerships,

withdrew from BCP between 2000 and 2001. Upon leaving

BCP, client members, including the Taxpayers, were paid in

Japanese yen in an amount equal to their remaining capital

account less expenses and fees. A client member triggered its

losses by liquidating its position in BCP and selling the yen.

Client members claimed an outside basis9 in their yen of

an amount equal to the assets they contributed to BCP—their

long option premiums—but did not reduce the basis by

contingent liabilities BCP assumed—their short options.

Because the short option liabilities were not fixed at the time

of transfer—they were out of the money and there was not an

obligation to pay on them unless, at expiration, they were in the

money—the partnership treated them as uncertain and ignored

them in computing the partners’ outside bases. Accordingly,

PCMG XII paid Refco the total premium: $249,213. Whether the

options expired worthless or paid out, Refco kept the total premium.

9

“Outside basis” is “[a] partner’s tax basis in a partnership

interest.” Woods, 571 U.S. at 35–36. Outside basis “functions as a

proxy for the value of the assets . . . contributed” to a partnership.

Petaluma FX Partners, LLC v. Comm’r, 792 F.3d 72, 75 (D.C. Cir.

2015).

12

when the Taxpayers sold their yen, it appeared they had

sustained massive losses. For example, after liquidating its

interest in BCP, PCMG XII received $478,748 worth of yen.

PCMG XII claimed a basis of $709,108,965—PCMG XII’s

long option premiums—in the yen. That is, PCMG XII claimed

the value of the assets it contributed to BCP was $709,108,965,

notwithstanding PCMG XII had paid a total premium of only

$3,354,857 for the option pairs it contributed to BCP. When

PCMG XII sold its yen—representing all that remained of the

assets PCMG XII had contributed to BCP—it appeared that the

value of the assets PCMG XII had contributed to BCP

decreased from over $700 million to $478,748. The Taxpayers

then used the losses generated from the Add-On to

substantially offset their income and reduce their taxes.10

After the 2001 distributions, BCP had no assets or

liabilities, its only remaining member was its managing

member, Bolton Capital, and BCP dissolved in June 2002. The

Commissioner contends the Add-On is a type of tax shelter

known as a Son-of-BOSS shelter, described by the Tax Court

as a series of steps whereby the taxpayers

transfer . . . assets encumbered by significant

liabilities to a partnership, with the goal of

increasing basis in that partnership. The

10

For example, for the tax year 2000, Kalkhoven reported

salary income of $492,523,171 and capital gains of $35,399,233 but

claimed combined losses of $533,578,758 from the three

partnerships, reducing his federal tax liability to $2,746,074. In other

instances, the Taxpayers even received tax refunds in the millions of

dollars. For tax year 2000, the Esreys reported salary income of

$83,724,716 and capital gains of $123,058,888 but, using a total loss

of $462,205,971 from the partnerships, reduced their tax liability to

$14,446 attributable to self-employment taxes, which resulted in a

$5,261,538 refund.

13

liabilities are usually obligations to buy

securities, and typically are not completely

fixed at the time of transfer. This may let the

partnership treat the liabilities as uncertain,

which may let the partnership ignore them in

computing basis. If so, the result is that the

partners will have a basis in the partnership so

great as to provide for large—but not out-of-

pocket—losses on their individual tax returns.

BCP, 2017 WL 3394123, at *1 n.2. As explained infra, the Tax

Court agreed with the Commissioner’s contention.

II. ANALYSIS

Tax Court decisions are reviewed “in the same manner and

to the same extent as decisions of the district courts in civil

actions tried without a jury.” I.R.C. § 7482(a)(1). Accordingly,

questions of law are reviewed de novo and factual findings for

clear error. Andantech LLC v. Comm’r, 331 F.3d 972, 976

(D.C. Cir. 2003). Mixed questions of law and fact are treated

as questions of fact and reviewed for clear error. Id. Under clear

error review, we assess the Tax Court’s findings under “all the

evidence of record,” Daniels v. Hadley Mem’l Hosp., 566 F.2d

749, 757 (D.C. Cir. 1977), and “may overturn the Tax

Court’s . . . findings only if we come to a ‘definite and firm

conviction that a mistake has been committed,’” Endeavor

Partners Fund, LLC v. Comm’r, 943 F.3d 464, 467 (D.C. Cir.

2019) (quoting United States v. U.S. Gypsum Co., 333 U.S.

364, 395 (1948)). Clear error occurs if a finding is based on a

“serious mistake as to the effect of evidence or is clearly

contrary to the weight of the evidence.” Daniels, 566 F.2d at

757 (footnotes omitted).

The Taxpayers first argue the Tax Court clearly erred in its

ruling that the extensions were valid because the Tax Court

14

misunderstood the facts and failed to apply them under the

correct legal standards. Next, the Taxpayers challenge the Tax

Court’s sham determination because it allegedly applied an

incorrect legal standard and clearly erred in its fact-finding.

Granted, the Tax Court opinion is at times unclear or its

reasoning is cursory. But such flaws do not per se establish

clear error. See ASA Investerings P’ship v. Comm’r, 201 F.3d

505, 511, 515 (D.C. Cir. 2000) (no clear error by Tax Court

although some “reasoning seem[ed] misdirected” and at times

its “focus . . . was a little puzzling”). Viewing the record as a

whole, we cannot come to a “definite and firm conviction that

a mistake has been committed,” U.S. Gypsum Co., 333 U.S. at

395, nor do we conclude that the Tax Court applied an incorrect

legal standard.11

A. The Statute Extensions

In Tax Court, the Taxpayers argued that the January 2004

Partnership Extension and the 2003/2004 Individual

Extensions were voidable under fiduciary and contract law;

further, the limitations period governing adjustments for the

2000 tax year expired before the adjustments issued because

extensions for that year were obtained outside the three-year

11

We recognize that “the presumption of correctness that

attaches to factual findings is stronger in some cases than in others.”

Bose Corp. v. Consumers Union of U.S., Inc., 466 U.S. 485, 500

(1984). Even though the presumption may have “lesser force” here

because Judge Holmes was not the trial judge and his “findings

[were] based on documentary evidence,” not live testimony, our

determination remains unaffected. Id. Judge Holmes

“demonstrate[d] that he complied with [Federal Rule of Civil

Procedure] 63’s basic requirement: that a successor judge become

familiar with relevant portions of the record.” Mergentime Corp. v.

Washington Metro. Area Transit Auth., 166 F.3d 1257, 1265 (D.C.

Cir. 1999).

15

limitations period. An FPAA is timely if either an individual

extension or the Partnership Extension is valid. The Taxpayers’

arguments that the extensions are void start from the same

general proposition: when the IRS sought the Partnership

Extension and Individual Extensions, E&Y had a conflict of

interest due to the civil and criminal investigations it was

facing, E&Y breached its duty to the Taxpayers because E&Y

never disclosed that conflict and the IRS ignored and facilitated

E&Y’s breach—ultimately benefitting from the breach by

securing the extensions. The Tax Court found that the

Taxpayers’ arguments failed irrespective of any E&Y conflict

or breach of duty to the Taxpayers. We agree with the Tax

Court, as we now explain.

1. The Partnership Extension and Bolton’s Fiduciary Role

Principles of agency and fiduciary law apply to extensions.

See Transpac Drilling Venture 1982-12 v. Comm’r, 147 F.3d

221, 225 (2d Cir. 1998). And under fiduciary law, “the

transactions of those who knowingly participate with [a]

fiduciary in . . . a breach are ‘as forbidden’ as transactions ‘on

behalf of the trustee himself.’” Dirks v. SEC, 463 U.S. 646, 659

(1983) (quoting Mosser v. Darrow, 341 U.S. 267, 272 (1951));

see also United States v. Dunn, 268 U.S. 121, 132 (1925) (“he

who fraudulently traffics with a recreant fiduciary shall take

nothing by his fraud”). Here, if the IRS knowingly trafficked

with a breaching fiduciary to obtain the extensions, it cannot

benefit from them.

In concluding that the Partnership Extension is valid under

fiduciary principles, the Tax Court focused on Bolton as the

relevant fiduciary because he, not E&Y, signed the Partnership

Extension as the Taxpayers’ fiduciary. BCP, 2017 WL

3394123, at *14. We find no fault in that focus. See In re

Martinez, 564 F.3d 719, 735 (5th Cir. 2009) (“the IRS’s ability

16

to deal with a [TMP] and rely on his actions on behalf of the

partnership is critical for the effective operation of the current

tax system”). The transaction at issue was between Bolton—

acting on behalf of the Taxpayers as their fiduciary—and the

IRS.

The Tax Court distinguished the facts sub judice from

those in a leading Second Circuit case. BCP, 2017 WL

3394123, at *14 (citing Transpac, 147 F.3d at 221). The issue

in Transpac was “whether, as a result of being placed under

criminal investigation by the IRS (and hence becoming subject

to pressure by the IRS), the [TMPs] labored under a conflict of

interest and thereby were disqualified from binding the

partnerships.” 147 F.3d at 222. The IRS sought and obtained

partnership extensions from the TMPs—who were at that time

under criminal investigation—after the limited partners refused

to sign individual extensions. Id. at 224. The TMPs cooperated

with the criminal investigation and were granted immunity or

offered suspended sentences by the prosecution. Id. at 223.

Because the IRS knew the TMPs had a “powerful incentive to

ingratiate themselves to the government,” they operated under

disabling conflicts and the IRS could not rely on their consent

to bind the limited partners. Id. at 227.

As the Tax Court recognized, this case is readily

distinguishable from Transpac. Bolton, as the TMP, was not

under criminal investigation at the time he signed the

Partnership Extension. Apparently, Bolton did not begin to

worry about potential criminal liability until two years after he

signed the January 2004 Partnership Extension. Accordingly,

the IRS had no reason to believe it was dealing with a breaching

fiduciary when it obtained Bolton’s consent to the Partnership

Extension. And unlike in Transpac, the Taxpayers did not

rebuff the IRS’s request for individual extensions—in fact, all

of the Taxpayers signed Individual Extensions. The Taxpayers

17

contend their agreement is tainted because they could not have

made an informed decision as to any extension without

knowing of E&Y’s conflict. But the Taxpayers’ acquiescence

does inform whether the IRS had reason to know Bolton was a

breaching fiduciary when it obtained the Partnership Extension

from him.12

2. The Partnership and Individual Extensions and Contract

Law

Although a statute extension is not a contract, “[c]ontract

principles are significant” in evaluating it because I.R.C.

12

The Taxpayers also argue the transaction between Bolton as

their fiduciary and the IRS is invalid because the IRS dealt with E&Y

in order to secure the Partnership Extension. But this argument

would require E&Y’s authority to secure the Partnership Extension

either through the Taxpayers or Bolton—and for the IRS to know

that. Evidence suggests that Six solicited input from the Taxpayers

on the Partnership Extension, J.A. 153–54, but there is no evidence

the IRS knew that. And the Taxpayers’ focus on Bolton himself fails

as well. Indeed, the Tax Court found the Taxpayers’ argument that

E&Y “embedded” Six in BCP unconvincing because Six left E&Y

for “messy personal reasons.” BCP, 2017 WL 3394123, at *14.

Although the Tax Court’s finding is brief, we do not believe it clearly

erred in finding E&Y did not have the influence to secure the

Partnership Extension through Bolton or that the IRS knew of E&Y’s

influence, if any. The communications between the IRS and E&Y

regarding Bolton’s consent to the Partnership Extension are

equivocal regarding E&Y’s influence over Bolton such that the IRS

knew E&Y was the real party securing the extension. Compare J.A.

815–16 (E&Y told the IRS it “request[ed]” Bolton to sign the

Partnership Extension), with J.A. 560 (IRS agent noted E&Y partner

said he “had the [TMP] designation signed and the statute

extensions”). In our view, E&Y’s bare “request” of Bolton does not

establish that the IRS knew that E&Y in fact had influence over

Bolton.

18

§ 6501(c)(4) “requires that the parties reach a written

agreement as to the extension” and an agreement “means a

manifestation of mutual assent.” Piarulle v. Comm’r, 80 T.C.

(CCH) 1035, 1042 (1983). Accordingly, the Tax Court applies

“general contract principles in interpreting, applying and

deciding the enforceability of waiver documents.” Chai v.

Comm’r, 102 T.C.M. (CCH) 520, 2011 WL 5600287, at *2

(2011).

The Taxpayers argue that the challenged extensions are

invalid under the contract principles of misrepresentation and

undue influence. Generally, misrepresentation is “an assertion

that is not in accord with the facts” or a material non-disclosure.

Restatement (Second) of Contracts §§ 159, 161. And undue

influence is the “unfair persuasion of a party . . . who by virtue

of the relation between [the party and the persuader] is justified

in assuming that [the persuader] will not act in a manner

inconsistent with his welfare.” Id. § 177(1). The extent of

unfair persuasion “depends on a variety of circumstances,”

including the “unavailability of independent advice.” Id.

cmt. b. A contract is voidable if a party’s manifestation of

assent is induced by a non-party’s misrepresentation or undue

influence unless the counterparty “in good faith and without

reason to know” of the non-party’s misrepresentation or undue

influence “gives value or relies materially on the transaction.”

Id. §§ 164, 177(3).

Six informed the Taxpayers that Bolton planned to sign the

Partnership Extension based on E&Y’s advice and that it would

be signed unless Bolton Capital heard from them. And E&Y

advised each Taxpayer to sign his Individual Extension.

Accordingly, if the Taxpayers’ assent to any extension was due

to E&Y’s misrepresentation or undue influence, the extension

could be voidable. Importantly, however, for the Taxpayers to

19

void the extensions under either contract theory, they must

have justifiably relied on E&Y. Id. §§ 164(2), 177(1).

i. Esrey and LeMay

In its Partnership Extension analysis, the Tax Court stated

that the “problem” with the Taxpayers’ contract argument was

that E&Y was not their “only adviser and they all had ample

reason to question E&Y long before 2004” when the

Partnership Extension was signed. BCP, 2017 WL 3394123, at

*15. In other words, the Taxpayers were less likely to be

unduly influenced because they had other advisors. And, in any

case, they could not justifiably rely on E&Y because, by the

time the Partnership Extension was signed, they should have

questioned E&Y’s good faith—whether or not they knew of

E&Y’s specific conflicts.

To support its ruling that the January 2004 Partnership

Extension was valid as to Esrey and LeMay, the Tax Court

relied on several facts. In 2000, Esrey and LeMay hired the

King & Spalding law firm to evaluate the Add-On. The law

firm ultimately “questioned whether [the Add-On] could get

through an audit.” Id. In 2002, LeMay informed E&Y that he

and Esrey had hired King & Spalding for its independent views

and instructed E&Y to consult with the firm on “all strategic

matters.” J.A. 538–39. In 2003, LeMay learned from a

newspaper reporter that the IRS was investigating E&Y as a

tax shelter promoter. The Tax Court found it “more likely than

not,” given their relationship, that LeMay informed Esrey

about the reporter’s information. BCP, 2017 WL 3394123, at

*15. And in May 2004, Esrey and LeMay hired outside counsel

to represent them in dealing with the IRS.

The Tax Court concluded that Esrey’s and LeMay’s

contract argument as to their Individual Extensions “doesn’t

work for the same reason it didn’t work for the partnership-

20

level extension.” Id. Accordingly, the Tax Court relied on the

same facts to support its holding that Esrey’s and LeMay’s

Individual Extensions—signed in December 2003 and January

2004, respectively—were valid agreements under contract law.

The Tax Court added that both Esrey and LeMay knew that

E&Y was being investigated because E&Y told them and both

Esrey and LeMay were “sophisticated businessmen.” Id.

We agree with the Tax Court. As early as 2000, King &

Spalding put Esrey and LeMay on notice that something could

be amiss with E&Y’s tax strategies. The Tax Court found that

King & Spalding had “questioned” whether the Add-On would

survive an audit. Id. Esrey testified that King & Spalding told

them both “the IRS had the better part of the argument”

regarding E&Y’s tax strategies’ legitimacy. J.A. 1607–08.

Even before hiring King & Spalding, LeMay was “beginning

to get a little insecure about [his] lack of knowledge” regarding

E&Y’s tax strategies after he read a news article discussing IRS

challenges to Son-of-BOSS tax shelters; he and Esrey then

decided to consult King & Spalding for advice. J.A. 858–59.

Knowledge of the civil promoter audit was another reason

Esrey and LeMay should have questioned E&Y’s actions. In

2003 LeMay was contacted by a national newspaper and asked

whether the promoter audit affected him. LeMay contacted

E&Y and E&Y told him the settlement was unrelated to him.

LeMay also read the press release regarding E&Y’s settlement

of the promoter audit. The Tax Court’s inference that LeMay

likely told Esrey about the call is reasonable, considering Esrey

admitted he and LeMay “talk[ed] . . . frequently and share[d]

each other’s thoughts or opinions” regarding press reports on

E&Y’s tax shelters. J.A. 855–56.

That Esrey and LeMay were sophisticated businessmen is

also relevant in evaluating whether either was justified in

21

relying on E&Y. See Restatement (Second) Contracts § 177

ill. 1 (“experience[] in business” relevant to whether one is

“justified in assuming” individual he “rel[ied] [on] in business

matters” will not act in manner inconsistent with his welfare).

Sophisticated businessmen who hire a global accounting firm

to prepare their tax returns should not rely unquestioningly on

that firm once they have direct knowledge of IRS scrutiny of

the firm’s tax strategies.13

ii. Kalkhoven and Pettit

As with Esrey and LeMay, the Tax Court concluded that

Kalkhoven and Pettit could not rely on misrepresentation or

undue influence to nullify the Partnership Extension because

E&Y was not their “only adviser and they all had ample reason

to question E&Y long before 2004.” BCP, 2017 WL 3394123,

at *15. In May 2002 E&Y advised Kalkhoven and Pettit that

E&Y was delivering requested documents to the IRS related to

“certain transactions in which [they] were involved” and

invited them to contact E&Y’s outside counsel with any

questions. Id. Eventually, in September 2004, Kalkhoven and

Pettit hired the Fulbright & Jaworski and Vinson & Elkins law

13

We do believe, however, that the Tax Court’s reliance on

Esrey’s and LeMay’s hiring of outside counsel in May 2004 is

misplaced. Counsel hired in May 2004 has no bearing on whether

Esrey and LeMay justifiably relied on, or were unduly influenced by,

E&Y when the relevant extensions had been signed. And we, like the

Taxpayers, are unsure what the Tax Court meant when it noted that

E&Y told Esrey and LeMay that prosecutors were investigating it

because there does not appear to be record evidence to support that

notation—at least no record evidence to support that disclosure

having been made before the relevant extensions were signed.

Regardless, the evidence the Tax Court utilized to support its

timeliness holding predates Esrey’s and LeMay’s execution of their

Individual Extensions and their approval of the Partnership

Extension.

22

firms to represent them in dealing with the IRS. And while

these firms represented Kalkhoven and Pettit, Bolton continued

to sign Partnership Extensions through April 2007.

Regarding Kalkhoven’s and Pettit’s Individual

Extensions—signed in September 200414—the Tax Court

similarly pointed to the fact that the two executives were then

represented by Fulbright & Jaworski and Vinson & Elkins. And

when they signed the extensions, both knew of E&Y’s conflicts

because E&Y had already sent the Add-On clients to Fulbright

& Jaworski because of those conflicts. E&Y also told

Kalkhoven and Pettit in August 2002 that it was subject to a

promoter audit regarding CDS and to contact its law firm of

McKee Nelson with any questions.

The Tax Court’s findings here were not error. Granted, the

fact that Kalkhoven and Pettit were represented by Fulbright &

Jaworski and Vinson & Elkins by September 2004 says nothing

about their reliance on, or the undue influence wielded by,

E&Y with respect to the January 2004 Partnership Extension.

But that Fulbright & Jaworski represented them does inform

whether they justifiably relied on E&Y in executing their

September 2004 Individual Extensions. Kalkhoven and Pettit

signed letters of engagement with Fulbright & Jaworski on the

same day they signed their individual extensions. But E&Y had

recommended that their clients transition to Fulbright &

Jaworski in August 2004 due to the conflict of interest

stemming from the May 2004 grand jury investigation. The

Tax Court inferred that Kalkhoven and Pettit had received the

letter because they hired the firm E&Y suggested in the letter.

Before hiring Fulbright & Jaworski, Pettit had signed an

14

Because the three-year limitations period had not expired

when Kalkhoven and Pettit signed their second Individual Extension

for tax year 2000 in September 2004, the Tax Court used the

September 2004 extensions as the operative ones.

23

engagement letter with Vinson & Elkins in March 2004, well

before his September 2004 Individual Extension.

Moreover, E&Y’s May 2002 letter also supports the Tax

Court’s determination that Kalkhoven and Pettit should have

questioned E&Y’s good faith. The letter informed them that the

IRS had served E&Y with an administrative summons

“demand[ing] the production of broad categories of documents

and other information with regard to certain transactions in

which [Kalkhoven and Pettit] were involved” and that E&Y

intended to comply. J.A. 544–45. Another letter—in August

2002—noted that the IRS was again examining E&Y

transactions via an administrative summons. Importantly, it

noted that the request related to the CDS transactions. Granted,

CDS was different from the Add-On but they were related

transactions in that Add-On was designed to eliminate capital

gains taxes generated from the CDS transactions.

In November 2003, before the Partnership Extension or

Kalkhoven’s and Pettit’s September 2004 individual

extensions were signed, Kalkhoven and Pettit received consent

and disclosure forms from E&Y. The consent form stated that

E&Y believed it could continue to represent Kalkhoven and

Pettit effectively. But it also stated the IRS had “taken the

position that E&Y acted as a tax shelter promoter of CDS and

[the Add-On] transactions” and noted several potential sources

of conflicts, including that E&Y had settled the promoter audit

and that individual E&Y personnel might be subject to

sanctions and might seek to assert defenses inconsistent with

their clients’ interests. J.A. 885–88. The disclosure letter

encouraged Kalkhoven and Pettit “to retain . . . independent

counsel to work with [E&Y].” J.A. 713; J.A. 719. And it

advised them that it was “rais[ing] . . . certain matters that

could be deemed to constitute conflicts of interest under

applicable ethical rules.” J.A. 714; J.A. 720. Nonetheless

24

Kalkhoven and Pettit signed conflict waivers in November

2003—before the January 2004 Partnership Extension and

their September 2004 Individual Extensions were executed.

In sum, the Tax Court outlined various events that

occurred before the Taxpayers’ Individual Extensions or the

Partnership Extension were signed, all of which should have

put the Taxpayers on notice that they should not rely on E&Y’s

advice any longer. Accordingly, we see no clear error in the

Tax Court’s findings.

B. The “Sham” Determination

In general, a partnership “may be disregarded where it is a

sham or unreal.” Moline Props., Inc. v. Comm’r, 319 U.S. 436,

439 (1943); see also ASA Investerings, 201 F.3d at 512. And in

a “sham” inquiry, “whether the ‘sham’ be in the entity or the

transaction[,] . . . the absence of a nontax business purpose is

fatal.” ASA Investerings, 201 F.3d at 512; see also Horn v.

Comm’r, 968 F.2d 1229, 1237 (D.C. Cir. 1992) (“extract[ing]”

from economic substance and business purpose tests that

transaction “will not be considered a sham if it is undertaken

for profit or for other legitimate nontax business purposes”).

Under the business purpose doctrine, “the Commissioner may

look beyond the form of an action to discover its substance[;]”

accordingly, although a “taxpayer may structure a transaction

so that it satisfies the formal requirements of the Internal

Revenue Code, the Commissioner may deny legal effect to a

transaction if its sole purpose is to evade taxation.” ASA

Investerings, 201 F.3d at 513 (quoting Zmuda v. Comm’r, 731

F.2d 1417, 1420–21 (9th Cir. 1984)). Further, a partnership is

not recognized as such for tax purposes unless “the parties

25

intended to join together as partners to conduct business

activity for a purpose other than tax avoidance.” Id.

The Taxpayers15 argue that the Tax Court’s determination

that BCP was a “sham” partnership was flawed because it

applied the incorrect legal standard and misunderstood the facts

as they related to the correct standard. Because the Tax Court

applied the correct legal standard and because, viewing the

record as a whole, we come to no “definite and firm conviction

that a mistake has been committed” in its findings, U.S.

Gypsum Co., 333 U.S. at 395, we affirm its sham

determination.

1. Application of Luna

The Taxpayers first argue that the Tax Court erred in using

the factors set out in Luna v. Commissioner, 42 T.C. 1067

(1964), to evaluate BCP because Luna is “analytically distinct”

from the business purpose doctrine and focuses on the incorrect

inquiry. Luna “distilled the principles” articulated in the United

States Supreme Court’s decisions in Commissioner v. Tower,

327 U.S. 280 (1946), and Commissioner v. Culbertson, 337

U.S. 733 (1949). WB Acquisition, Inc. v. Comm’r, 101 T.C.M.

(CCH) 1157, 2011 WL 477697, at *9 (2011), aff’d, 803 F.3d

1014 (9th Cir. 2015). In both Tower and Culbertson, the

Supreme Court evaluated whether an existing partnership “is

real within the meaning of the federal revenue laws.” Tower,

327 U.S. at 290; see also Culbertson, 337 U.S. at 741. Tower

established that the key analysis is intent: “whether the partners

really and truly intended to join together for the purpose of

carrying on business and sharing in the profits or loses or both.”

15

In Tax Court only Kalkhoven and Pettit argued BCP was a

legitimate partnership engaged in legitimate business. Esrey and

LeMay conceded that the Add-On transactions were “bogus,” J.A.

1619, and “outright frauds,” J.A. 1762.

26

327 U.S. at 287. Culbertson explained that the intent inquiry is

fact-intensive and describes factors to evaluate an intent to

form a partnership. 337 U.S. at 742.

In Luna, the Tax Court considered whether the parties in a

business relationship had informally entered into a partnership

under the Tax Code, allowing them to claim that a payment to

one party was intended to buy a partnership interest. See 42

T.C. at 1076–77. To determine whether the parties formed an

informal partnership for tax purposes, the Luna Court asked

“whether the parties intended to, and did in fact, join together

for the present conduct of an undertaking or enterprise.” Id. at

1077 (citing Culbertson, 337 U.S. at 733). Luna listed non-

exclusive factors to determine whether the intent necessary to

establish a partnership existed. Id. at 1077–78.16

The Taxpayers are correct that Luna’s intent inquiry is

“analytically distinct” from the business-purpose doctrine but

the two analyses are not mutually exclusive. See, e.g.,

Chemtech Royalty Assocs., LP v. United States, 766 F.3d 453,

460–61 (5th Cir. 2014) (Tower/Culberson inquiry appropriate

16

The Luna factors include: “The agreement of the parties and

their conduct in executing its terms; the contributions, if any, which

each party has made to the venture; the parties’ control over income

and capital and the right of each to make withdrawals; whether each

party was a principal and coproprietor, sharing a mutual proprietary

interest in the net profits and having an obligation to share losses, or

whether one party was the agent or employee of the other, receiving

for his services contingent compensation in the form of a percentage

of income; whether business was conducted in the joint names of the

parties; whether the parties filed Federal partnership returns or

otherwise represented to respondent or to persons with whom they

dealt that they were joint venturers; whether separate books of

account were maintained for the venture; and whether the parties

exercised mutual control over and assumed mutual responsibilities

for the enterprise.”

27

because “[t]he fact that a partnership’s underlying business

activities had economic substance does not, standing alone,

immunize the partnership from judicial scrutiny [under

Culbertson]” (internal quotations omitted)); Historic

Boardwalk Hall, LLC v. Comm’r, 694 F.3d 425, 461 (3d Cir.

2012) (same); TIFD III-E, Inc. v. United States, 459 F.3d 220,

230–32 (2d Cir. 2006) (district court erred in considering only

partnership’s “economic substance” and ignoring Culbertson’s

“all-facts-and-circumstances test”). At least inferentially, we

have recognized the Luna factors by describing the “basic

inquiry” as “whether, all facts considered, the parties intended

to join together as partners to conduct business activity for a

purpose other than tax avoidance.” ASA Investerings, 201 F.3d

at 513; see also Andantech LLC v. Comm’r, 331 F.3d 972, 978

(D.C. Cir. 2003) (citing Culbertson, 337 U.S. at 742–43).

Accordingly, the Luna factors are appropriately applied to the

intent inquiry. See TIFD III-E, 459 F.3d at 230–32 (Luna noted

as one of multiple cases “identifying factors a court might

consider” to evaluate whether partners joined partnership with

requisite intent).

The Taxpayers argue that, if Luna is applicable, BCP

satisfies its factors. But the Tax Court disagreed and did not

clearly err in this “fact-intensive inquiry.” Saba P’ship v.

Comm’r, 273 F.3d 1135, 1140 (D.C. Cir. 2001). We agree with

the Tax Court that “the agreement of the parties and their

conduct in executing its terms” and “whether business was

conducted in the joint names of the parties” weigh against

finding BCP a partnership for tax purposes. BCP, 2017 WL

3394123, at *17 (quoting Luna, 42 T.C. at 1077). BCP’s

“business” was limited to one type of transaction: the Add-On.

After accepting the options, BCP’s only activities were settling

paired options and paying distributions, plus paying minimal

advisor fees. And the fees paid to E&Y and Bolton to

28

participate in the Add-On were based on the tax loss generated

by the Add-On.

“[W]hether the parties exercised mutual control over and

assumed mutual responsibilities for the enterprise” also weighs

against finding BCP to be a bona fide partnership. Id. (quoting

Luna, 42 T.C. at 1078). Bolton Capital had an unusual amount

of control over BCP. The operating agreement gave Bolton

Capital “all powers and rights necessary, proper, convenient or

advisable to effectuate and carry out the purposes, business and

objectives of the Company.” J.A. 269. The client members

were not permitted “to take part in the management or control

of the business or affairs of the Company, including, without

limitation, voting to remove the Managing Member” or “have

any voice in the management or operation of any Company

property.” J.A. 274. Further, Bolton Capital was either the

“Managing Member, General Partner, . . . Tax Matters

Partner . . . [or had] Power of Attorney” for every client

member and Bolton signed the BCP operating agreement on

behalf of every client member. J.A. 82. The Taxpayers note that

limited partnerships controlled by one general partner are

commonplace. But Luna’s multi-factor test emphasizes that the

determination is fact intensive—the Tax Court validly found

that Bolton’s level of control was particularly unusual here.

Accordingly, the Tax Court correctly applied the Luna

factors to determine “whether the parties intended to, and did

in fact, join together for the present conduct of an undertaking

or enterprise” and correctly concluded that BCP failed the Luna

analysis. BCP, 2017 WL 3394123, at *17.

2. The Business Purpose/Economic Substance Doctrines

Generally, an entity is considered a “sham” and

disregarded for tax purposes if it is not “undertaken for profit

or for other legitimate nontax business purposes.” Horn, 968

29

F.2d at 1238 (applying economic substance and business

purpose factors). Both the business purpose and economic

substance doctrines “look beyond the form of an action to

discover its substance.” ASA Investerings, 201 F.3d at 513

(internal quotations omitted). Taxpayers are entitled to

structure their business transactions “in such a way as to

minimize tax” but the business purpose doctrine is not met if

“such structuring is deemed to have gotten out of hand, to have

been carried to such extreme lengths that the business purpose

is no more than a facade.” Id. The Taxpayers contend that

BCP’s formation was intended to achieve, and in fact did

achieve, diversification—an “indisputably legitimate business

purpose.” Appellants’ Br. at 67.

The Tax Court’s determination that diversification was

merely a “facade” is well supported by the record. BCP, 2017

WL 3394123, at *19. Granted, the record contains conflicting

evidence. Some testimony suggests diversification was a goal

of BCP—for example, Bolton stated he believed pooling of the

partners’ assets in BCP would provide diversification and E&Y

told Kalkhoven the pooling of foreign currency investments in

BCP would achieve diversification. But other testimony

suggests any non-tax motive was fabricated. Six stated that she

was not aware of any non-tax reason for contributing the option

pairs to BCP and Bolton “helped fabricate a non-tax motivation

used to falsely explain why clients participated in the CDS

Add-On shelter.” J.A. 596. The Tax Court’s rejection of

Kalkhoven’s and Pettit’s testimony on diversification as “not

credible and inconsistent with the objective facts” is also well

supported by the record. BCP, 2017 WL 3394123, *19 n.22.

Both Kalkhoven and Pettit admitted they did not know what

the Add-On was and did not even know their investments were

part of the Add-On—they simply testified that, as part of a

30

broad investment plan, they invested with Bolton Capital to

diversify.

Although a finance/economics professor gave expert

testimony that pooling of the option pairs achieved

diversification, the Tax Court must “look beyond the form of

[the] action to discover its substance.” ASA Investerings, 201

F.3d at 513 (internal quotations omitted). Accordingly, it

evaluated the substance of BCP and Add-On to determine the

business purpose’s validity. It evaluated how the option pairs

functioned and found the option pairs would never hit the sweet

spot. The Tax Court found Add-On was focused on tax savings:

it was promoted specifically to offset capital gains from CDS

and transaction fees were based on the tax loss generated.

Without the sweet spot, the maximum payout from

participating in the Add-On was less than the transaction costs

to acquire the options and participate.17 We agree with the Tax

Court’s ultimate conclusion that BCP had no valid business

purpose.

Tax minimization as a primary consideration is not

unlawful. ASA Investerings, 201 F.3d at 513. Nevertheless, the

business purpose doctrine can be violated if the structuring for

tax benefits has “gotten out of hand” and the business purpose

is “no more than a facade.” Id.; see also id. at 514 (“a

transaction will be disregarded if it did ‘not appreciably affect

[taxpayer’s] beneficial interest except to reduce his tax.’”

(brackets in original) (quoting Knetsch v. United States, 364

17

The Taxpayers’ argument that the Tax Court erred by

considering the lack of profit motive misses the point—a transaction

is valid under the business purpose doctrine if it is “undertaken for

profit or for other legitimate nontax business purposes.” Horn, 968

F.2d at 1238. The Tax Court concluded that neither existed and,

accordingly, found BCP to be a sham. We cannot fault the Tax Court

for covering its bases.

31

U.S. 361, 366 (1960)). In other words, the business purpose

doctrine is “simply [a] more precise factor[] to consider in the

application of this court’s traditional sham analysis; that is,

whether the transaction had any practical economic effects

other than the creation of income tax losses.” Horn, 968 F.2d

at 1237 (internal quotations omitted). We do not disagree with

the Tax Court’s conclusion that BCP and the Add-On had no

practical economic effect other than the creation of tax losses.

Client members invested only $16.5 million in the option pairs

and claimed $3.1 billion in tax losses. Those losses were

artificial—which the Tax Court recognized. BCP, 2017 WL

3394123, at *16. And any diversification benefit was only in

the options’ payoff distribution. But no option pair in fact paid

out—they all either expired worthless or were sold before their

exercise date. No “diversification benefit” in the payoff was

had—plainly by design.18

III. SIMPSON’S INTERVENTION

Simpson’s motion for intervention came about through a

gap in Tax Court rules. After the Tax Court released its 2017

memorandum opinion, it ordered the parties to agree on the

language of its final decisions. When the parties subsequently

conferred, a non-participating party (Simpson) was discovered.

If a tax case settles, Tax Court Rule 248 requires the

Commissioner to move for entry of decision and the court to

wait 60 days to see if a non-participating party objects to the

settlement before issuing its decision. See Tax Ct. R. 248(b)(4).

18

To the extent the Tax Court’s statements regarding the effect

of disregarding BCP could be read to determine the Taxpayers’

outside bases in BCP, the Tax Court lacked jurisdiction to do so—

which it acknowledged. BCP, 2017 WL 3394123, at *12; see

Petaluma FX Partners, LLC v. Comm’r, 792 F.3d 72, 77 (D.C. Cir.

2015). In addition, those findings were not included in the Tax

Court’s final decisions.

32

There is no analogous rule, however, if the parties litigate and

subsequently agree on the language of the decision. Here,

Simpson’s late husband was a partner in Moore Trading

Partners (MTP) and MTP was a partner in BCP; his estate “was

an indirect partner and thus a party, [who] had not participated

in the litigation.” J.A. 2448. In any event, on October 26, 2017,

the Tax Court gave 60 days’ notice of the proposed decisions

to non-participating parties. On August 6, 2018, Simpson,

individually and as the surviving spouse of Singleton “Garry”

Simpson, moved to intervene to assert an untimeliness defense.

Simpson “adopt[ed] and incorporate[d]” the Taxpayers’ legal

arguments regarding their statute of limitations defenses and

attached documents to establish that she and her husband had

not agreed to an individual extension until after the limitations

period had expired. J.A. 2454. On February 6, 2019, the Tax

Court denied Simpson’s motion to intervene.

The Tax Court has not issued rules for third-party

intervention. McHenry v. Comm’r, 677 F.3d 214, 216 (4th Cir.

2012). Under Tax Court Rule 1(b), the Tax Court is authorized

to prescribe such procedure, “giving particular weight to the

Federal Rules of Civil Procedure to the extent that they are

suitably adaptable to govern the matter at hand.” Tax Ct. R.

1(b). We agree with the Fourth Circuit that, because Tax Court

Rule 1(b) gives the Tax Court “broad discretion in deciding

whether and to what extent to follow Federal Rule of Civil

Procedure [(FRCP)] 24 governing intervention” and because

“Rule 24 itself confers broad discretion on a trial court, we give

great deference to a Tax Court’s decision to deny intervention,

reviewing only for a clear abuse of discretion.” McHenry, 667

F.3d at 216. Here, the Tax Court did not clearly abuse its

discretion in denying Simpson’s motion to intervene.

Simpson did not specify whether she was seeking

mandatory intervention under FRCP 24(a) or permissive

33

intervention under FRCP 24(b) and so the Tax Court addressed

both. First, the Tax Court noted intervention of right is not

appropriate if the existing parties adequately represent the

intervenor’s interests, see Fed. R. Civ. P. 24(a), and permissive

intervention is not appropriate if it would unduly delay the

adjudication of the existing parties’ rights, see Fed. R. Civ. P.

24(b). It observed that, if either her individual extensions or the

Partnership Extension was valid, any adjustments were timely.

The Tax Court had earlier found the Partnership Extension

valid and Simpson offered no additional argument on the

Partnership Extension—incorporating by reference the

Taxpayers’ failed argument. Accordingly, the Tax Court

determined Simpson was adequately represented on the issue

because she asserted no other basis for the Partnership

Extension’s invalidity—failing intervention of right. It also

concluded that Simpson failed permissive intervention because

such intervention would “merely duplicate” the Taxpayers’

Partnership Extension argument “which would serve only to

further delay [the litigation’s] conclusion.” J.A. 2487. We

therefore conclude that the Tax Court did not abuse its

discretion in denying Simpson’s motion to intervene.

For the foregoing reasons, the Tax Court’s memorandum

opinion issued August 7, 2017, its order issued February 6,

2019 and its two decisions issued February 7, 2019 are

affirmed.

So ordered.

This is a copy of a public record, reproduced as it was published. It is not legal advice, and it may not be the version a court would rely on. Check the official source before you cite it.

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