Ad Investment 2000 Fund LLC, Community Media, Inc., A Partner Other Than the Tax Matters Partner v. Commissioner

AD INVESTMENT 2000 FUND LLC, COMMUNITY MEDIA, INC.,

A PARTNER OTHER THAN THE TAX MATTERS PARTNER,

PETITIONER v. COMMISSIONER OF INTERNAL

REVENUE, RESPONDENT

AD GLOBAL 2000 FUND LLC, WARSAW TELEVISION CABLE

CORP., A PARTNER OTHER THAN THE TAX MATTERS

PARTNER, PETITIONER v. COMMISSIONER OF

INTERNAL REVENUE, RESPONDENT

Docket Nos. 9177–08, 9178–08. Filed April 16, 2014.

In anticipation of Ps’ affirmative defenses to accuracy-

related penalties (e.g., reasonable cause and good faith), R

248

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(248) AD INV. 2000 FUND LLC v. COMMISSIONER 249

moves (1) to compel production of letters expressing attorneys’

opinions as to whether it was more likely than not that antici-

pated tax benefits from transactions in question would be

upheld and (2) to sanction Ps for noncompliance with any

order directing production. Ps object on grounds that the let-

ters are privileged attorney-client communications. R argues

that Ps impliedly waived any privilege by putting into issue

the LLCs’ beliefs and state of mind. Ps deny that the LLCs

relied on the letters. Held: By putting the LLCs’ legal knowl-

edge and understanding into contention in order to establish

good-faith and state-of-mind defenses, Ps forfeit the LLCs’

privilege protecting attorney-client communications relevant

to the content and the formation of their legal knowledge,

understanding, and beliefs; an order directing production will

be issued. Held, further, if Ps fail to comply with the order

directing production, the Court will consider the sanction of

preventing Ps, in support of affirmative defenses, from intro-

ducing evidence of the LLCs’ reasonable beliefs and state of

mind.

Elliot Silverman, Howard Kleinhendler, and Orrin Eliot

Tilevitz, for petitioners.

Veronica L. Trevino, Kathryn F. Patterson, Jarrod R. Jen-

kins, and Elaine Harris, for respondent.

OPINION

HALPERN, Judge: In each of these consolidated cases,

respondent has moved (motions) for us to compel petitioner

to produce documents and to sanction petitioner if it fails to

comply with any resulting order to produce the documents.

Petitioners object (objection). We will grant the motions

insofar as they ask us to compel production of documents,

and we will set them for hearing insofar as they ask us to

sanction petitioners for failure to comply with our order.

Except as otherwise stated, all section references are to the

Internal Revenue Code of 1986, as amended and in effect for

2000.

Background

These consolidated cases are partnership-level actions

involving what respondent describes as a Son-of-BOSS tax

shelter. 1 On that basis, respondent has adjusted partnership

1A ‘‘Son-of-BOSS’’ tax shelter is a variant of the Bond and Options Sales

Continued

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250 142 UNITED STATES TAX COURT REPORTS (248)

items of the two partnerships 2 and determined that section

6662 accuracy-related penalties should apply to any resulting

underpayments of tax. In connection with his penalty deter-

minations, respondent alleges that his adjustments of part-

nership items are attributable to a tax shelter. He also

alleges that the underpayments of tax resulting from his

adjustments of partnership items are attributable to (1) a

substantial understatement of income tax, (2) a gross valu-

ation misstatement, or (3) negligence or disregard of rules

and regulations. The partnerships’ tax years in question are

both calendar year 2000. Petitioners have assigned error to

respondent’s adjustments and to his penalty determinations.

Respondent seeks to compel the production of six opinion

letters (opinions) from the law firm of Brown & Wood LLP.

Respondent represents, and petitioners do not contradict,

that the opinions express Brown & Wood’s opinion as to

whether, on the basis of representations made to it, it was

more likely than not that the anticipated tax benefits from

the transactions in question would be upheld for Federal

income tax purposes. Petitioners argue that they need not

produce the opinions since each is a privileged communica-

tion between attorney and client that need not be disclosed.

Respondent appears to accept that the opinions constitute

attorney-client communications but argues that, under the

common law doctrine of implied waiver, the attorney-client

privilege is waived when the client places otherwise privi-

leged matters in controversy. Respondent argues that peti-

tioners placed the opinions into controversy by relying on

affirmative defenses to the penalties that turn on the part-

nerships’ beliefs or state of mind.

It is true that, in defense to respondent’s determinations of

an accuracy-related penalty based on a substantial under-

statement of income tax, see sec. 6662(b)(2), petitioners aver:

Strategy (BOSS) tax shelter. ‘‘The purpose of all Son-of-BOSS tax shelters

is to create ‘artificial tax losses designed to offset income from other trans-

actions.’ ’’ 6611, Ltd. v. Commissioner, T.C. Memo. 2013–49, at *11 (quoting

Napoliello v. Commissioner, 655 F.3d 1060, 1062 (9th Cir. 2011), aff ’g T.C.

Memo. 2009–104).

2 Apparently, the two LLCs, AD Investment 2000 Fund LLC (ADI) and

AD Global 2000 Fund LLC (ADG), have elected to be taxed as partner-

ships. See sec. 301.7701–3(a), Proced. & Admin. Regs. Consistent with the

parties’ usage, we will refer to the entities as partnerships.

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(248) AD INV. 2000 FUND LLC v. COMMISSIONER 251

‘‘There is or was substantial authority for the Partnership’s

and its partners’ tax treatment of any items resulting in an

underpayment of tax, and the Partnership and its partners

reasonably believed that their tax treatment of such items

was more likely than not the proper [tax] treatment’’. See

sec. 6662(d)(2)(C). 3 In defense to respondent’s determination

of accuracy-related penalties generally, petitioners aver: ‘‘Any

underpayment of tax was due to reasonable cause and with

respect to which the Partnership and its partners acted in

good faith.’’ See sec. 6664(c)(1). Petitioners deny, however,

that their averments bring professional advice (i.e., the opin-

ions) into question.

With respect to petitioners’ first defense, to respondent’s

determination of an accuracy-related penalty based on a

substantial understatement of income tax, the key point

appears to be whether each partnership (acting through its

principals or its agents) reasonably believed (belief require-

ment) that its tax treatment of partnership items was more

likely than not the proper tax treatment. The belief require-

ment is found in section 6662(d)(2)(C)(i)(II) and elaborated

upon in section 1.6662–4(g)(4), Income Tax Regs. Section

1.6662–4(g)(1)(i)(B), Income Tax Regs., provides that the

belief requirement is satisfied if ‘‘[t]he taxpayer reasonably

believed at the time the return was filed that the tax treat-

ment of that item was more likely than not the proper treat-

ment.’’ The regulations provide that a taxpayer may satisfy

the belief requirement by either of two methods. They pro-

vide that the requirement is satisfied if either

(A) [first method] The taxpayer analyzes the pertinent facts and

authorities in the manner described in paragraph (d)(3)(ii) of this sec-

tion, and in reliance upon that analysis, reasonably concludes in good

faith that there is a greater than 50-percent likelihood that the tax

treatment of the item will be upheld if challenged by the Internal Rev-

enue Service; or

(B) [second method] The taxpayer reasonably relies in good faith on

the opinion of a professional tax advisor, if the opinion is based on the

tax advisor’s analysis of the pertinent facts and authorities in the

manner described in paragraph (d)(3)(ii) of this section and unambig-

uously states that the tax advisor concludes that there is a greater than

3 As

acknowledged by the parties during a conference call with the Court

to clarify the point, we are concerned here only with partnership-level de-

fenses to the penalty. Cf. sec. 301.6221–1(c) and (d), Proced. & Admin.

Regs. But see sec. 1.6662–4(g)(5), Income Tax Regs.

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252 142 UNITED STATES TAX COURT REPORTS (248)

50-percent likelihood that the tax treatment of the item will be upheld

if challenged by the Internal Revenue Service.

[Sec. 1.6662–4(g)(4)(i), Income Tax Regs.]

Respondent concedes that petitioners’ averments raise only

the first method (self-determination), and not the second

method (reliance on professional advice), to show that the

partnerships satisfy the belief requirement. Nevertheless,

respondent argues, petitioners have placed the opinions into

controversy by relying on a reasonable cause, good-faith

defense and by putting the partnerships’ beliefs into issue.

Respondent states: ‘‘Under the first method, * * * those tax

opinions remain relevant to the subjective inquiries into

reasonableness and good faith.’’ He adds: ‘‘Putting reasonable

belief in issue places the Partnership[’s], and specifically

James Haber’s, state of mind at issue.’’ He explains: ‘‘Mr.

Haber [‘de facto manager of the partnership vehicle[s]’]

received the subject tax opinions before taking the ques-

tioned positions and presumably before making his alleged

self-determination of authorities.’’ The opinions are relevant,

respondent argues, because, if they contradict Mr. Haber’s

claimed self-determination, they may show that his self-

determination was not reasonable, and, if consistent with his

self-determination, they may show that he made no self-

determination. Respondent also argues:

The subject tax opinions are also relevant to the good faith element of

the penalty defense[s]. * * * The facts contained in the subject tax opin-

ions necessarily reflect communications made by Mr. Haber on behalf of

ADG [or ADI] and the ADG [or ADI] Partners for the purpose of

securing tax advice. Evidence that Mr. Haber solicited advice on the

basis of facts that were incomplete or altogether false, compared to the

facts about the * * * [option partnership strategy] adduced at trial,

would indicate that he knew that the tax benefits claimed were not

proper. This would show bad faith.

Petitioners respond: ‘‘[T]he petitions do not assert any

advice-of-counsel defense, nor do they mention (or even

allude to) any advice from their attorneys. The Petitions do

allege that * * * [the partnerships] and their partners

reasonably believed the positions on the Partnerships’ tax

returns to be correct, but such a defense need not rely on

professional advice.’’ They argue: ‘‘A generalized ‘good faith’

defense, not specifically relying on the advice of counsel is

not a waiver of the attorney-client privilege. [Pritchard v.

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(248) AD INV. 2000 FUND LLC v. COMMISSIONER 253

Cnty. of Erie] In re County of Erie, 546 F.3d 222, 229 (2d Cir.

2008); In re Grand Jury, 219 F.3d [175] at 183 [(2d. Cir.

2000)]; United States v. White, 887 F.2d 267, 270–71 (D.C.

Cir. 1989)’’. In response to respondent’s arguments that the

opinions are relevant to factual questions presented by the

partnerships’ belief, reasonable cause, and good-faith

defenses, petitioners respond: ‘‘[T]he mere fact that attorney-

client communications would be ‘relevant’ is not a sufficient

basis to waive the privilege. Rhone-Poulenc Rorer Inc. v.

Home Indemnity Co., 32 F.3d 851, 863–64 (3d Cir. 1994).’’

Respondent relies principally on Johnston v. Commis-

sioner, 119 T.C. 27, 37 (2002), in which the taxpayer

‘‘asserted reliance on qualified experts as an affirmative

defense to respondent’s fraud penalty allegations.’’ Inter-

preting that reference to qualified experts to include legal

counsel, id. at 37–38, we undertook the approach of deter-

mining whether there was an implied waiver as outlined in

Hearn v. Rhay, 68 F.R.D. 574, 581 (E.D. Wash. 1975). We

considered whether (1) assertion of the privilege was a result

of some affirmative act, such as filing suit, by the asserting

party; (2) through this affirmative act, the asserting party

put the protected information at issue by making it relevant

to the case; and (3) application of the privilege would have

denied the opposing party access to information vital to his

defense. Johnston v. Commissioner, 119 T.C. at 36. We held

that all three elements of the Hearn test for implied waiver

had been satisfied. Id. at 40. Respondent argues that he has

established that the three elements of the Hearn test are

satisfied in these cases. He adds that the Hearn test has

been endorsed by the Court of Appeals for the D.C. Circuit.

See Sanderlin v. United States, 794 F.2d 727 (D.C. Cir.

1986).

Petitioners respond that, although adopted by this Court in

Johnston, the Hearn approach has been explicitly rejected by

the U.S. Court of Appeals for the Second Circuit in Pritchard

v. Cnty. of Erie (In re Cnty. of Erie), 546 F.3d 222, 229 (2d

Cir. 2008). Petitioners contend that, in Pritchard, the Court

of Appeals held that to impliedly waive the attorney-client

privilege, ‘‘a party must rely on privileged advice from his

counsel to make his claim or defense.’’ Id. The Court of

Appeals for the Second Circuit is the presumptive venue for

appeal of these cases. See sec. 7482(b)(1)(B). For that reason,

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254 142 UNITED STATES TAX COURT REPORTS (248)

petitioners add that, under the rule of Golsen v. Commis-

sioner, 54 T.C. 742 (1970), aff ’d, 445 F.2d 985 (10th Cir.

1971), Pritchard governs in these cases.

Discussion

I. Golsen Doctrine

Section 7453 provides in pertinent part that Tax Court

proceedings are conducted in accordance with the rules of

evidence applicable to trials without a jury in the U.S. Dis-

trict Court for the District of Columbia. The Federal Rules

of Evidence apply to proceedings before the U.S. District

Court for the District of Columbia. See Fed. R. Evid. 1101.

The Federal Rules of Evidence incorporate the common law

rules of privilege. See Fed. R. Evid. 501, 1101(c). Under the

rule of Golsen v. Commissioner, 54 T.C. at 757, this Court

will ‘‘follow a Court of Appeals decision which is squarely in

point where appeal from our decision lies to that Court of

Appeals’’. Because the facts in front of us are materially

distinguishable from those of Pritchard, we need not consider

whether under the Golsen rule we should follow the Court of

Appeals for the Second Circuit’s opinion in that case.

II. Claim of Privilege

A. Introduction

‘‘As construed under Federal common law, the attorney-

client privilege exists ‘to encourage full and frank commu-

nication between attorneys and their clients and thereby pro-

mote broader public interests in the observance of law and

administration of justice.’ ’’ Johnston v. Commissioner, 119

T.C. at 34 (quoting Upjohn v. United States, 449 U.S. 383,

389 (1981)). Nevertheless:

It is well established doctrine that in certain circumstances a party’s

assertion of factual claims can, out of considerations of fairness to the

party’s adversary, result in the involuntary forfeiture of privileges for

matters pertinent to the claims asserted. * * *

In some circumstances, courts have ruled that it would be unfair for a

party asserting contentions to an adjudicating authority to then rely on

its privileges to deprive its adversary of access to material that might

disprove or undermine the party’s contentions. * * *

[In re Grand Jury Proceedings John Doe Co. v. United States, 350 F.3d

299, 302 (2d Cir. 2003).]

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(248) AD INV. 2000 FUND LLC v. COMMISSIONER 255

See also, e.g., Chevron Corp. v. Pennzoil Co., 974 F.2d 1156,

1162 (9th Cir. 1992) (‘‘Where a party raises a claim which in

fairness requires disclosure of the protected communication,

the privilege may be implicitly waived.’’). ‘‘Whether fairness

requires disclosure has been decided by the courts on a case-

by-case basis, and depends primarily on the specific context

in which the privilege is asserted.’’ United States v. Doe (In

re Grand Jury Proceedings), 219 F.3d 175, 183 (2d Cir. 2000).

When a person puts into issue his subjective intent in

deciding how to comply with the law, he may forfeit the

privilege afforded attorney-client communications. See, e.g.,

United States v. Exxon Corp., 94 F.R.D. 246, 248 (D.D.C.

1981) (‘‘Most courts considering the matter have concluded

that a party waives the protection of the attorney-client

privilege when he voluntarily injects into the suit the ques-

tion of his state of mind.’’). Professor Rice, in his treatise,

Attorney-Client Privilege in the United States, makes a

similar point: ‘‘The most common situation in which courts

have found waiver is where the client claims that he acted

on the ‘good faith’ belief that his conduct was reasonable and

legal.’’ Paul R. Rice, 2 Attorney-Client Privilege in the United

States, sec. 9:53, at 434 (2013–2014 ed. 2013). United States

v. Bilzerian, 926 F.2d 1285 (2d Cir. 1991), involved an appeal

from convictions for financial crimes. The trial court had

ruled that, if the defendant testified regarding his good-faith

efforts to comply with the securities laws, he would open the

door to cross-examination with respect to the basis for his

belief regarding the lawfulness of his actions and that such

cross-examination would allow inquiry into communications

that he had with his attorney (‘‘discussions ordinarily pro-

tected by the attorney-client privilege’’). Id. at 1291. The

defendant did not testify. On appeal, he contended that his

testimony would not have disclosed the content or even the

existence of any privileged communications or asserted a reli-

ance on counsel. Id. For that reason, he argued, the attorney-

client privilege would not be waived by his testimony and,

therefore, the trial court committed reversible error in

denying his motion in limine seeking to protect the privilege.

Id. at 1292. The Court of Appeals disagreed that his testi-

mony would not waive the privilege, holding that, even if his

testimony did not advert to protected communications, he

would implicitly waive the privilege if he asserted a claim

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256 142 UNITED STATES TAX COURT REPORTS (248)

‘‘that in fairness requires examination of protected commu-

nications.’’ Id. The Court of Appeals then found:

This waiver principle is applicable here for Bilzerian’s testimony that he

thought his actions were legal would have put his knowledge of the law

and the basis for his understanding of what the law required in issue.

His conversations with counsel regarding the legality of his schemes

would have been directly relevant in determining the extent of his

knowledge and, as a result, his intent. [Id.]

The court concluded: ‘‘The trial court’s ruling left defendant

free to testify without getting into his state of mind, but cor-

rectly held that if he asserted his good faith, the jury would

be entitled to know the basis of his understanding that his

actions were legal.’’ Id. at 1294. In Cox v. Adm’r U.S. Steel

& Carnegie, 17 F.3d 1386, 1419 (11th Cir. 1994), relying on

Bilzerian, the Court of Appeals for the Eleventh Circuit

stated: ‘‘USX could have denied criminal intent without

affirmatively asserting that it believed that its change in

pension fund policy was legal. Having gone beyond mere

denial, affirmatively to assert good faith, USX injected the

issue of its knowledge of the law into the case and thereby

waived the attorney-client privilege.’’ More recently, in

Pritchard, 546 F.3d at 228–229, although finding no implied

waiver of the attorney-client privilege and noting that the

petitioners therein did not claim a good-faith or state-of-mind

defense, the Court of Appeals for the Second Circuit general-

ized: ‘‘[T]he assertion of a good-faith defense involves an

inquiry into state of mind, which typically calls forth the

possibility of implied waiver of the attorney-client privilege.’’

In Anderson v. Nixon, 444 F. Supp. 1195, 1200 (D.D.C. 1978),

Judge Gesell put the rule thus: ‘‘[A] client waives his

attorney privilege when he brings suit or raises an affirma-

tive defense that makes his intent and knowledge of the law

relevant.’’

B. Belief Requirement

To satisfy the belief requirement by the first method (i.e.,

under section 1.6662–4(g)(4)(i)(A), Income Tax Regs.) peti-

tioners must show that the partnerships ‘‘analyze[d] the

pertinent facts and [legal] authorities * * * and in reliance

upon that analysis, reasonably * * * conclude[d] in good

faith that there * * * [was] a greater than 50-percent likeli-

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(248) AD INV. 2000 FUND LLC v. COMMISSIONER 257

hood that the tax treatment of the item * * * [would] be

upheld if challenged by the Internal Revenue Service’’. Peti-

tioners’ averments that the partnerships satisfied the belief

requirement by the first method put into dispute the partner-

ships’ knowledge of the pertinent legal authorities. Peti-

tioners’ averments also put into contention the partnerships’

understanding of those legal authorities and their application

of the legal authorities (i.e., the law) to the facts. Finally, the

averments put into contention the basis for the partnerships’

belief that, if challenged, their tax positions would more

likely than not succeed in the courts. Petitioners have thus

placed the partnerships’ legal knowledge, understanding, and

beliefs into contention, and those are topics upon which the

opinions may bear. If petitioners are to rely on the legal

knowledge and understanding of someone acting for the part-

nerships to establish that the partnerships reasonably and in

good faith believed that their claimed tax treatment of the

items in question was more likely than not the proper treat-

ment, it is only fair that respondent be allowed to inquire

into the bases of that person’s knowledge, understanding,

and beliefs including the opinions (if considered). See, e.g.,

Cox, 17 F.3d 1386; Bilzerian, 926 F.2d 1285; Anderson, 444

F. Supp. 1195.

Apparently, each partnership received the opinions well

before its 2000 tax returns were due. Petitioners do not claim

that those acting for the partnerships ignored the opinions.

They claim only that the regulations provide an alternative

pursuant to which the partnerships may satisfy the belief

requirement by self-determination (without relying on profes-

sional advice). That is true. See sec. 1.6662–4(g)(4)(i), Income

Tax Regs. It is, however, beside the point. The point is that,

by placing the partnerships’ legal knowledge and under-

standing into issue in an attempt to establish the partner-

ships’ reasonable legal beliefs in good faith arrived at (a

good-faith and state-of-mind defense), petitioners forfeit the

partnerships’ privilege protecting attorney-client communica-

tions relevant to the content and the formation of their legal

knowledge, understanding, and beliefs. E.g., Cox, 17 F.3d

1386; Bilzerian, 926 F.2d 1285. Pritchard, 546 F.3d 222, is

not to the contrary. The Court of Appeals there stated: ‘‘Peti-

tioners do not claim a good faith or state of mind defense.

They maintain only that their actions were lawful or that

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258 142 UNITED STATES TAX COURT REPORTS (248)

any rights violated were not clearly established. In view of

the litigation circumstances, any legal advice rendered by the

County Attorney’s office is irrelevant to any defense so far

raised by Petitioners.’’ Id. at 229.

C. Reasonable Cause Exception

Section 6664(c)(1) provides that the accuracy-related pen-

alty shall not be imposed with respect to any portion of an

underpayment if the taxpayer shows there was reasonable

cause for, and that he acted in good faith with respect to,

that portion. Section 1.6664–4(b)(1), Income Tax Regs., pro-

vides:

The determination of whether a taxpayer acted with reasonable cause

and in good faith is made on a case-by-case basis, taking into account

all pertinent facts and circumstances. * * * Generally, the most impor-

tant factor is the extent of the taxpayer’s effort to assess the taxpayer’s

proper tax liability. Circumstances that may indicate reasonable cause

and good faith include an honest misunderstanding of * * * law that is

reasonable in light of all of the facts and circumstances, including the

experience, knowledge, and education of the taxpayer. * * *

As stated, petitioners aver: ‘‘Any underpayment of tax was

due to reasonable cause and with respect to which the Part-

nership and its partners acted in good faith.’’ Petitioners do

not in the objection contest respondent’s claim in the motions

that the opinions ‘‘are * * * relevant to the good faith ele-

ment of the penalty defense.’’ For the reasons set forth with

respect to the belief requirement, petitioners have with

respect to the section 6664(c)(1) reasonable cause exception

forfeited the privilege that would otherwise apply to the opin-

ions.

D. Conclusion

Petitioners’ averments in support of their affirmative

defenses to respondent’s determination of accuracy-related

penalties put into contention the state of mind of those who

acted for the partnerships and the partnerships’ good-faith

efforts to comply with the tax law. If petitioners persist in

those defenses, it would be unfair to deprive respondent of

knowledge of the contents of the opinions and the oppor-

tunity to put those opinions into evidence. If petitioners per-

sist, they sacrifice the privilege to withhold the contents of

the opinions.

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(248) AD INV. 2000 FUND LLC v. COMMISSIONER 259

III. Conclusion

As stated, we will grant the motions insofar as they ask us

to compel production of documents. We will set the motions

for hearing insofar as they ask us to sanction petitioners for

failure to comply with our order granting the motions, with

an eye, if there is noncompliance, toward prohibiting peti-

tioners from introducing evidence that the partnerships met

the belief requirement by self-determination or that someone

acting for the partnerships had a good-faith and honest mis-

understanding of law.

An appropriate order will be issued.

f

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