# Ackerman v. Comm'r

> United States Tax Court · April 15, 2009 · 97 T.C.M. 1392

URL: https://www.frixlaw.com/law-library/cases/4337541

## Case

- **Full name:** PETER ACKERMAN AND JOANNE LEEDOM-ACKERMAN v. COMMISSIONER OF INTERNAL REVENUE
- **Court:** United States Tax Court
- **Decided:** April 15, 2009
- **Citations:** 97 T.C.M. 1392; 2009 T.C. Memo. 80; 2009 Tax Ct. Memo LEXIS 81
- **Precedential status:** Unpublished
- **Opinion:** Opinion
- **Judges:** Chiechi
- **Cited by:** 2 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/4337541

## How later opinions describe it (automated extraction)

- finding no trade or business as "promoter" where taxpayer did not receive fees or commissions for providing advisory services

## Opinion text

T.C. Memo. 2009-80

UNITED STATES TAX COURT

PETER ACKERMAN AND JOANNE LEEDOM-ACKERMAN, Petitioners v.
COMMISSIONER OF INTERNAL REVENUE, Respondent

Docket Nos. 13947-06, 26400-06. Filed April 15, 2009.

George W. Connelly, Jr., Linda S. Paine, and Pamela E.

Powers, for petitioners.

Christopher A. Fisher and Richard S. Bloom, for respondent.

Table of Contents

FINDINGS OF FACT . . . . . . . . . . . . . . . . . . . . . . 4

Background . . . . . . . . . . . . . . . . . . . . . . . . . 5
Peter Ackerman . . . . . . . . . . . . . . . . . . . . . 5
Perry Lerner . . . . . . . . . . . . . . . . . . . . . . 7
Don Ackerman . . . . . . . . . . . . . . . . . . . . . . 8
Jason Ackerman . . . . . . . . . . . . . . . . . . . . . 8
Jeffrey Deutschman . . . . . . . . . . . . . . . . . . . 9
- 2 -

Somerville S Trust and Certain
Other Entities That It Owned . . . . . . . . . . 9
Deena Patriarca . . . . . . . . . . . . . . . . . . . 11
Rockport Advisors . . . . . . . . . . . . . . . . . . 11
Crown Capital . . . . . . . . . . . . . . . . . . . . 13
Petitioners’ Tax Returns . . . . . . . . . . . . . . . 15
Notices of Deficiency . . . . . . . . . . . . . . . . 16

Claimed Business Expense Deductions . . . . . . . . . . . . 16

Claimed Deduction for the
Protection of Business Reputation . . . . . . . . . . . 32
Funds Advanced to ECC . . . . . . . . . . . . . . . . 33
Book and Tax Treatment of the $7,850,000 of
Advanced Funds by Somerville and by Santa Monica . 37

Claimed Losses With Respect to ISI . . . . . . . . . . . . 40

Claimed Theft Loss Deduction . . . . . . . . . . . . . . . 42

Accuracy-Related Penalty Under Section 6662(a) . . . . . . 49

OPINION . . . . . . . . . . . . . . . . . . . . . . . . . . 54

Burden of Proof . . . . . . . . . . . . . . . . . . . . . . . 54

Evaluation of Evidence on Which Petitioners Rely . . . . . 56
Testimonial Evidence . . . . . . . . . . . . . . . . . 56
Mr. Ackerman’s Testimony . . . . . . . . . . . . 57
Mr. Lerner’s Testimony . . . . . . . . . . . . . 57
Don Ackerman’s Testimony . . . . . . . . . . . . 57
Jason Ackerman’s Testimony . . . . . . . . . . . 58
Mr. Deutschman’s Testimony . . . . . . . . . . . 58
Ms. Patriarca’s Testimony . . . . . . . . . . . . 58
Mr. Braddock’s Testimony . . . . . . . . . . . . 59
Mr. Levinton’s Testimony . . . . . . . . . . . . 59
Documentary Evidence . . . . . . . . . . . . . . . . . 59

Claimed Business Expense Deductions . . . . . . . . . . . . 60
Petitioners’ Cost Company or Agency Argument . . . . . 61
Petitioners’ Compensation Argument . . . . . . . . . . 71

Claimed Deduction for the
Protection of Business Reputation . . . . . . . . . . . 88

Claimed Losses With Respect to ISI . . . . . . . . . . . . 96

Claimed Theft Loss Deduction . . . . . . . . . . . . . . . 104
- 3 -

Accuracy-Related Penalty Under Section 6662(a) . . . . . . 108

APPENDIX A . . . . . . . . . . . . . . . . . . . . . . . . 117

APPENDIX B . . . . . . . . . . . . . . . . . . . . . . . . 119

MEMORANDUM FINDINGS OF FACT AND OPINION

CHIECHI, Judge: Respondent determined the following defi-

ciencies in, an addition under section 6651(a)(1)1 to, and

accuracy-related penalties under section 6662(a) on petitioners’

Federal income tax (tax):

Addition to Tax Accuracy-Related Penalty
Year Deficiency Under Sec. 6651(a)(1) Under Sec. 6662(a)

1997 $1,022,612 -- --
1998 163,350 -- --
2000 657,877 -- --
2002 771,330 $20,959.40 $154,266.00
2004 206,239 -- 41,247.80

The issues remaining for decision are:2

(1) Are petitioners entitled for each of their taxable years

1997, 1998, 2000, 2002, and 2004 to deduct certain claimed

business expenses under section 162(a)? We hold that they are

not.

1
All section references are to the Internal Revenue Code in
effect for the years at issue. All Rule references are to the
Tax Court Rules of Practice and Procedure.
2
Issues (2), (3), and (4) set forth below are affirmative
issues that petitioners raised in the pleadings and that do not
relate to any determinations in the notices of deficiency.
- 4 -

(2) Are petitioners entitled for their taxable year 1997 to

deduct under section 162(a) certain funds that they claim peti-

tioner Peter Ackerman advanced to a certain corporation in order

to protect his business reputation? We hold that they are not.

(3) Is a certain loss with respect to a company in which

petitioner Peter Ackerman indirectly owned an interest a passive

activity loss within the meaning of section 469(a) for each of

petitioners’ taxable years 1998 and 2000? We hold that it is.

(4) Are petitioners entitled for their taxable year 2002 to

deduct a claimed theft loss under section 165(a)? We hold that

they are not.

(5) Are petitioners liable for each of their taxable years

2002 and 2004 for the accuracy-related penalty under section

6662(a)? We hold that they are.

FINDINGS OF FACT3

Some of the facts have been stipulated and are so found

except as stated below.

Petitioners resided in Washington, D.C., at the time they

filed the petition in each of these cases.

3
We found the record in these cases to have been not well
developed, inconclusive, and/or not reliable in many respects,
including certain material respects. Although the gaps in the
record are substantial in many instances, and therefore our
findings of fact are incomplete and/or disconnected in those
instances, we have not undertaken to note every instance in which
the record does not contain reliable evidence that would have
enabled us to find all the facts relevant to our deciding the
issues presented.
- 5 -

Background

Peter Ackerman

Petitioner Peter Ackerman (Mr. Ackerman) received a bache-

lor’s degree from Colgate University and a master’s degree in law

and diplomacy and a Ph.D. degree from the Fletcher School of Law

and Diplomacy of Tufts University (Fletcher School).

From the mid-1970s until January 1990, Drexel Burnham

Lambert (Drexel) employed Mr. Ackerman in various positions.4

The first position that Mr. Ackerman held at Drexel was assistant

to the president. From 1978 to 1989, Mr. Ackerman was in charge

of Drexel’s so-called special projects group. As head of that

group, Mr. Ackerman worked on, inter alia, the restructuring and

the financing of various businesses. Drexel received various

types of fees, equity interests, and investment opportunities in

connection with its special projects work.

In early 1990, Mr. Ackerman moved to London, England (Lon-

don), where he became a visiting scholar at the International

Institute for Strategic Studies, a premier think tank that

concentrated on issues relating to international security.

While living in London, Mr. Ackerman registered with English

authorities as a person undertaking a business and formed, owned

4
While at Drexel, Mr. Ackerman worked on, inter alia, the
restructuring of Penn Central Railroad and Resorts International
and the formation and the financing of a company for the purpose
of taking over a certain other company that operated supermar-
kets.
- 6 -

with petitioner Joanne Leedom-Ackerman (Ms. Ackerman), and served

as the director of a company known as Rockport Capital Limited.

The principal activity of that company was providing certain

consulting services.

From 1990 to 1992, Ms. Ackerman owned a company known as

Rockport Consultants, Inc. (Rockport Consultants), that was

incorporated as a Delaware corporation on September 5, 1990, and

that filed an election to be taxed as an S corporation on or

about January 1, 1991. Rockport Consultants was engaged in the

business of providing certain consulting services. While resid-

ing in London, Mr. Ackerman served as the director of Rockport

Consultants and acted on behalf of that company in providing

certain consulting services. The consulting services that

Rockport Consultants provided included certain consulting ser-

vices provided to Saatchi & Saatchi Company Plc. (Saatchi &

Saatchi) with respect to, inter alia, its financing and its

capital structure. In exchange for those services, Rockport

Consultants received from Saatchi & Saatchi fees of more than $5

million.

On or about January 3, 1992, Rockport Consultants changed

its name to Rockport Financial, Inc. (Rockport Financial).
- 7 -

During each of Rockport Financial’s taxable years 1992, 1993, and

1994, Ms. Ackerman was its sole stockholder.5

At the end of 1995, Mr. Ackerman left London and returned to

the United States. Thereafter, as discussed in more detail

below, Mr. Ackerman became interested in and explored various

investment opportunities.

During each of the years 1997, 1998, 2000, 2002, and 2004,

the years at issue, Mr. Ackerman devoted 40 to 50 percent of his

time to social and charitable causes. For example, Mr. Ackerman

served on the respective boards of CARE and Freedom House and as

chairman of the Fletcher School.

Perry Lerner

While Mr. Ackerman was living in London, he met Perry Lerner

(Mr. Lerner). Mr. Lerner received a bachelor’s degree from

Claremont McKenna College and a law degree from Harvard Univer-

sity. From approximately 1980 to 1996, Mr. Lerner practiced law

as a tax attorney with the law firm of O’Melveny & Myers, LLP

(O’Melveny & Myers). In that capacity, Mr. Lerner represented

Mr. Ackerman with respect to various legal matters. Around 1996,

Mr. Lerner resigned from O’Melveny & Myers in order to provide

certain legal services for Mr. Ackerman on a full-time basis.

5
As discussed below, on or about Apr. 15, 1996, Rockport
Financial changed its name to Rockport Capital, Inc. (Rockport
Capital).
- 8 -

In February 1996, Mr. Lerner formed Rockport Advisors, Inc.

(Rockport Advisors). In January 1997, he formed Crown Capital

Group, Inc. (Crown Capital). As discussed in more detail below,

Mr. Lerner used Rockport Advisors and Crown Capital in order to

provide certain services with respect to certain investment

opportunities that Mr. Ackerman wanted to explore and/or pursue.

Don Ackerman

Don Ackerman is the older brother of Mr. Ackerman. From

around 1965 to around the end of 1997, Don Ackerman managed the

business operations of Economy Color Card, Inc. (ECC), a supplier

of wallpaper sample books and sample cards for paint, rugs, and

wood pieces.

Jason Ackerman

Jason Ackerman is the son of Don Ackerman and the nephew of

Mr. Ackerman. Jason Ackerman received an undergraduate degree in

economics and business management from Boston University.

Beginning around 1990, Jason Ackerman worked as an investment

banker (1) for about a year at Drexel and (2) for about seven

years at Donaldson Lufkin Jenrette. While serving as an invest-

ment banker, Jason Ackerman worked on several business deals that

involved the formation of companies for the purpose of taking

over certain other companies that operated supermarkets.
- 9 -

Jeffrey Deutschman

Jeffrey Deutschman (Mr. Deutschman) received a bachelor’s

degree in history and economics from Columbia University and a

master’s degree in business administration from the Graduate

School of Management of the University of California, Los An-

geles. From 1981 through 1997, Mr. Deutschman worked for or was

a partner in various private equity firms.

Mr. Deutschman first met Mr. Ackerman in 1981 while Mr.

Ackerman was working for Drexel. At that time, Mr. Deutschman

had been working for a private equity firm for which Drexel had

been interested in financing an acquisition.

Somerville S Trust and Certain
Other Entities That It Owned

During each of the years at issue, Mr. Ackerman was treated

as the owner of Somerville S Trust, a so-called grantor trust

under section 671. For all relevant taxable years of petition-

ers, all of the income, deductions, and credits of Somerville S

Trust were includible in the computation of their taxable income

and credits. During each of the years at issue, Mr. Lerner was

the trustee of Somerville S Trust and was fully empowered to

transfer or invest its assets.

On or about April 15, 1996, Rockport Financial changed its

name to Rockport Capital. During each of the years at issue,
- 10 -

Somerville S Trust was the sole stockholder of Rockport Capital.6

Pursuant to a limited liability company agreement dated

December 10, 1996, Rockport Capital and Mr. Lerner formed Santa

Monica Pictures, LLC (Santa Monica). Since its formation, Santa

Monica has been subject to the unified partnership provisions of

sections 6221 through 6234. On December 11, 1996, Somerville S

Trust became a member of, and received a 99.882-percent profits

interest in, Santa Monica. During 1997 and thereafter, the

members of Santa Monica were Somerville S Trust, Rockport Capi-

tal, and Mr. Lerner.

Pursuant to a limited liability company agreement dated

December 15, 1997, Somerville S Trust formed Somerville, LLC

(Somerville). From its formation until December 29, 1997,

Somerville S Trust was the sole member of Somerville. On Decem-

ber 29, 1997, Somerville S Trust contributed its interest in

Somerville to Santa Monica, and Santa Monica became, and has

remained, the sole member of Somerville.7

6
The record does not disclose when or how Somerville S Trust
acquired its interest in Rockport Capital.
7
Somerville was a “disregarded” entity under secs. 301.7701-
2(a) and 301.7701-3(a) and (b)(1)(ii), Proced. & Admin. Regs.,
and was not required to file a tax return for any of the years at
issue. Nonetheless, as discussed in more detail below, it
prepared Form 1065, U.S. Return of Partnership Income (Form
1065), for each of those years.
- 11 -

Deena Patriarca

From 1984 until February 1990, Drexel employed Deena

Patriarca (Ms. Patriarca) as an assistant to Mr. Ackerman.

Shortly thereafter, Rockport Capital or one of its predecessors

employed her.8 During each of the years at issue, Ms. Patriarca

handled (1) the bookkeeping, accounting, payroll, and similar

functions for Rockport Capital and (2) the bookkeeping for

Somerville S Trust.

Rockport Advisors

As discussed above, in February 1996, Mr. Lerner formed

Rockport Advisors, which was located in Washington, D.C.9 During

8
For several months after Ms. Patriarca left Drexel, she
provided certain unidentified services for Mr. Ackerman in his
personal capacity.
9
The record is very sparse as to the activities of Rockport
Advisors during each of the years at issue. The record, however,
does establish that (1) as of Aug. 25, 1995, Somerville S Trust
was a member of, and had agreed to make capital contributions
totaling $100 million to, Cumberland Investment Partners, LLC
(Cumberland Investment), (2) the purpose of Cumberland Investment
was to invest in securities and other similar investments, and
(3) on Mar. 1, 1996, Rockport Advisors agreed to provide certain
unidentified administrative services to Cumberland Investment.

The record also establishes that on Mar. 1, 1996, Rockport
Advisors and two individuals entered into an employment agreement
(Rockport Advisors employment agreement) under which Rockport
Advisors was to, and did, employ those two individuals (two
Rockport Advisors employees). That agreement provided that
Somerville S Trust was to “bear the costs of the services per-
formed by * * * [the two Rockport Advisors employees] on behalf
of Rockport Advisors.” The Rockport Advisors employment agree-
ment further provided the following mechanism by which Somerville
S Trust was to recoup those costs:

(continued...)
- 12 -

each of the years at issue, Mr. Lerner was the sole owner of

Rockport Advisors. At all relevant times, Rockport Advisors

maintained books and records, had employees, and generated

income.

Rockport Advisors filed Form 1120, U.S. Corporation Income

Tax Return (Form 1120), for each of its taxable years 1997, 1998,

and 2000.10 In each of those returns, Rockport Advisors showed

its business activity as “ADVISORY SERVICES” and its product or

service as “CONSULTING”.

In Form 1120 for its taxable year 1997, Rockport Advisors

reported total income of $1,600,196, total deductions of

$1,909,634, and a loss of $309,438. In Form 1120 for its taxable

year 1998, Rockport Advisors reported total income of $951,395,

total deductions of $1,144,857, and a loss of $193,462. In Form

9
(...continued)
To allow Somerville [S Trust] to recoup these costs,
* * * [the two Rockport Advisors employees were to]
cause to be paid to Somerville [S Trust] 25% of any
performance-based fees * * * [they] receive in the
future while * * * employed by Rockport Advisors from
clients other than Cumberland [Investment], until
Somerville [S Trust] has received an amount equal to
the unrecovered balance in its “Recoupment Account.”
* * *

The record further establishes that in 2000 and 2001 the two
Rockport Advisors employees caused $60,000 and $100,031.73,
respectively, to be paid to Rockport Advisors in order for
Somerville S Trust to recoup the costs that it had incurred with
respect to the services performed by them.
10
The record does not disclose whether Rockport Advisors
filed Form 1120 for any of the other taxable years at issue.
- 13 -

1120 for its taxable year 2000, Rockport Advisors reported total

income of $1,296,676, total deductions of $1,239,039, and taxable

income of $57,637.

Crown Capital

As discussed above, in January 1997, Mr. Lerner formed Crown

Capital, which was located in New York City. On or about January

1, 1998, Crown Capital filed an election to be taxed as an S

corporation. At all relevant times, Mr. Lerner owned 49 percent

and petitioners’ nephew Jason Ackerman owned 51 percent of Crown

Capital. Crown Capital never issued any of its stock to Mr.

Ackerman.

At all relevant times, Crown Capital maintained books and

records, had employees, and generated income.11 As discussed

below, during at least certain of the years at issue, Crown

Capital provided certain services, including “consultation,

advice and direct management assistance * * * with respect to

operations, strategic planning, [and] financing”, to certain

companies in which Mr. Ackerman indirectly invested. In exchange

for those services, those companies agreed to pay certain manage-

ment fees to Crown Capital.

11
From 1997 until early 2002, Sheila Innes, an employee of
Crown Capital, maintained Crown Capital’s books and records.
Around early 2002, Crown Capital began winding down its business
operations and shipped its books and records to Ms. Patriarca.
- 14 -

Mr. Ackerman, whose reputation in finance far exceeded the

respective reputations of the employees of Crown Capital, was

involved in the hiring of Crown Capital’s employees in that he

told Crown Capital whom to hire or consented to its hiring of

certain employees. By the end of 1997, Crown Capital had about

15 employees, including Mr. Lerner, Jason Ackerman, and Don

Ackerman.12 In 1998, Mr. Deutschman joined Crown Capital and

served as its managing director. It was Mr. Deutschman’s under-

standing that Crown Capital was established to provide certain

services regarding the various companies in which Mr. Ackerman

invested or intended to invest.

Mr. Lerner, Jason Ackerman, and Mr. Deutschman were the key

employees of Crown Capital. Mr. Ackerman negotiated the respec-

tive salaries that Crown Capital was to pay to those key employ-

ees.

Crown Capital filed Form 1120 for its taxable year 1997 and

Form 1120S, U.S. Income Tax Return for an S Corporation (Form

1120S), for each of its taxable years 1998 and 2000.13 In each

12
The record does not disclose when Don Ackerman began
working for Crown Capital. We presume that shortly after Don
Ackerman stopped managing the operations of ECC, which was
sometime around the end of 1997, he began working for Crown
Capital.
13
The record does not disclose whether Crown Capital filed
Form 1120S for any of the other taxable years at issue.
- 15 -

of those returns, Crown Capital showed its business activity as

“CONSULTING” and its product or service as “INVESTMENT ADVICE”.

In Form 1120 for its taxable year 1997, Crown Capital

reported total income of $1,754,632, total deductions of

$1,735,293, and taxable income of $19,339. In Form 1120S for its

taxable year 1998, Crown Capital reported total income of

$5,649,920, total deductions of $5,549,062, and “Ordinary income

* * * from trade or business activities” of $100,858. In Form

1120S for its taxable year 2000, Crown Capital reported total

income of $6,509,302, total deductions of $6,194,276, and “Ordi-

nary income * * * from trade or business activities” of $315,026.

Petitioners’ Tax Returns

Petitioners jointly filed Form 1040, U.S. Individual Income

Tax Return (joint return), for each of their taxable years 1997,

1998, 2000, 2002, and 2004.

Petitioners included Schedule C, Profit or Loss From Busi-

ness (Schedule C), as part of the 1997 joint return (1997 Sched-

ule C), the 1998 joint return (1998 Schedule C), the 2000 joint

return (2000 Schedule C), the 2002 joint return (2002 Schedule

C), and the 2004 joint return (2004 Schedule C). In each of

those schedules, petitioners showed the “Principal business or

profession, including product or service” as “INVESTMENTS AND

BANKING” and the “Business name” as “PETER ACKERMAN”.
- 16 -

Petitioners also included Schedule E, Supplemental Income

and Loss (Schedule E), as part of the 1997 joint return, the 1998

joint return, the 2000 joint return, the 2002 joint return, and

the 2004 joint return. In each of those schedules, petitioners

reported, inter alia, Somerville S Trust’s allocable share of any

income or loss, including any dividend income, from each of the

limited liability companies in which that trust directly or

indirectly invested.14

Notices of Deficiency

On April 26, 2006, respondent issued to petitioners a notice

of deficiency with respect to their taxable years 1997, 1998, and

2000 (notice for 1997, 1998, and 2000). On November 17, 2006,

respondent issued to petitioners a notice of deficiency with

respect to their taxable years 2002 and 2004 (notice for 2002 and

2004).

Claimed Business Expense Deductions

During the years at issue, various individuals and companies

sought Mr. Ackerman’s advice with respect to certain projects

that those individuals and companies were considering. Mr.

14
For convenience, instead of referring to what was reported
by petitioners as Somerville S Trust’s allocable share of any
income or loss, including any dividend income, from each of the
limited liability companies in which that trust directly or
indirectly invested, we shall generally refer only to the tax
reporting by those limited liability companies which are involved
in certain of the issues presented and in which Somerville S
Trust was a direct or indirect investor.
- 17 -

Ackerman and Crown Capital’s key employees (namely, Mr. Lerner,

Jason Ackerman, and Mr. Deutschman) examined each of those pro-

jects in order to determine whether it was a project that Mr.

Ackerman wanted to pursue. Mr. Ackerman and Crown Capital’s key

employees (namely, Mr. Lerner, Jason Ackerman, and Mr.

Deutschman) examined a total of about six to ten potential pro-

jects for every project that Mr. Ackerman decided to pursue. It

was Mr. Ackerman who determined which employees of Crown Capital

were to work on the projects that he wanted to pursue.

During the years at issue, Mr. Ackerman pursued at least

five major projects (major projects).15 As discussed in more

detail below, each of those projects pertained to a company in

which Mr. Ackerman indirectly made a substantial investment.16 As

part of its business, Crown Capital (1) provided certain due

15
Except for a project that pertained to a company that
purchased cellular phone spectrum licenses and that was facing
financial difficulty, the record does not disclose the number or
the nature of any projects, other than the five major projects,
that Mr. Ackerman may have explored and/or pursued during the
years at issue.
16
Mr. Ackerman did not directly own an interest in any of
the companies to which the major projects pertained. Instead, as
discussed in more detail below, Mr. Ackerman invested in each of
those companies through one or more entities in which he directly
or indirectly owned a substantial interest, such as Somerville S
Trust, Somerville, and Santa Monica. Although Mr. Ackerman did
not directly own an interest in any of the companies to which the
major projects pertained, in discussing those projects, we shall
sometimes for convenience not describe Mr. Ackerman’s investments
and ownership interests in those companies as indirect invest-
ments and indirect ownership interests.
- 18 -

diligence services in connection with the major projects and

(2) monitored the progress of Mr. Ackerman’s respective invest-

ments in the companies to which those projects pertained.

Mr. Ackerman maintained no books and records with respect to

the projects that he pursued during the years at issue. Nor did

he have any employees or lease agreements with respect to those

projects.

One major project that Mr. Ackerman pursued involved the

financing of a resort theater business. On a date not disclosed

by the record, Mr. Lerner introduced Mr. Ackerman to an individ-

ual (resort theater developer) who had been in the process of

acquiring a small chain of movie theaters located in certain

resort areas and who had been having difficulty financing those

acquisitions.

On February 18, 1999, Santa Monica, virtually all of which

Mr. Ackerman owned indirectly, invested $14 million in Resort

Theaters of America, Inc. (Resort Theaters), in exchange for a

100-percent ownership interest in Resort Theaters. On the same

date, Crown Capital entered into a management services agreement

with Resort Theaters (Resort Theaters management service agree-

ment). Pursuant to that agreement, in exchange for certain fees

to be paid by Resort Theaters to Crown Capital, Crown Capital was

to provide to Resort Theaters certain management services, in-

cluding “consultation, advice and direct management assistance to
- 19 -

* * * [Resort Theaters] with respect to operations, strategic

planning, financing and other aspects of the business of [Resort

Theaters]”.

On certain dates not disclosed by the record, Crown Capital

and Mr. Ackerman assisted the resort theater developer in obtain-

ing certain financing for Resort Theaters.17

The business operations of Resort Theaters were ultimately

unsuccessful, and it did not pay to Crown Capital any of the fees

required by the Resort Theaters management service agreement.

Santa Monica reported in Form 1065 for its taxable year 2000

a long-term capital loss of $14 million with respect to its

investment in Resort Theaters.18

Another major project that Mr. Ackerman pursued involved the

formation of an investment management company. Mr. Ackerman

learned of that project through Jay Regan (Mr. Regan), whom Mr.

Ackerman had known for many years.

On a date not disclosed by the record in or shortly before

1999, Mr. Regan introduced Mr. Ackerman to Marek Fludzinski (Mr.

17
The record does not disclose whether Mr. Ackerman assisted
Resort Theaters in obtaining financing before or after Santa
Monica invested in that company.
18
In Form 1065 for its taxable year 2000, Santa Monica
reported with respect to its investment in Resort Theaters that
(1) it had acquired its interest in Resort Theaters on Feb. 18,
1999; (2) its basis in that interest was $14 million; and (3) it
had sold that interest on Dec. 31, 2000. In that form, Santa
Monica made no entry in the column headed “Sales price” with
respect to the interest in Resort Theaters that it reported it
had sold.
- 20 -

Fludzinski). Mr. Fludzinski had been managing a fund for a large

investment partnership and wanted to leave that partnership in

order to start his own investment management business. From 1999

to 2000, Mr. Ackerman assisted Mr. Fludzinski in an undisclosed

manner in forming Thales Fund Management, LLC (Thales Fund Man-

agement), which was to be the manager of an investment company

called Thales Fund, LP (Thales Fund). Mr. Ackerman asked Mr.

Lerner to provide assistance with respect to certain of the legal

matters pertaining to the formation of Thales Fund Management.

On a date not disclosed by the record, Mr. Ackerman and Mr. Regan

made investments of $30 million and $20 million, respectively,

with respect to the project involving the creation of Thales Fund

Management.19

Another major project that Mr. Ackerman pursued involved

starting a towel manufacturing business in Mexico for Davidson

Cotton Holding Corp. (Davidson Cotton). Mr. Ackerman

19
The record does not establish what ultimately happened to
the investment of $30 million that Mr. Ackerman made with respect
to the project involving the creation of Thales Fund Management.
Nor does the record establish the specific entity or entities in
which or through which Mr. Ackerman made that investment.
However, Somerville reported in Form 1065 distributive shares of
taxable income generated by the operations of (1) Thales Fund
Management and Thales Capital, LLC (Thales Capital), for each of
Somerville’s taxable years 1999 through 2004 and (2) Thales Fund,
for each of Somerville’s taxable years 1999, 2000, 2002, and
2004. We presume from Somerville’s Form 1065 for each of its
taxable years 1999 through 2004 that Mr. Ackerman made his
investment of $30 million through Somerville.
- 21 -

learned of that project through his brother Don Ackerman shortly

after Don Ackerman began working for Crown Capital.

On December 3, 1999, Mr. Ackerman invested in Davidson

Cotton.20 On the same date, Crown Capital entered into a manage-

ment services agreement with Davidson Cotton (Davidson Cotton

management services agreement). Pursuant to that agreement, in

exchange for certain fees to be paid by Davidson Cotton to Crown

Capital, Crown Capital was to provide to Davidson Cotton certain

“executive management services, including consultation, advice

and direct management assistance * * * with respect to opera-

tions, strategic planning, financing and other aspects of the

business of” Davidson Cotton.

On certain dates not disclosed by the record, the key em-

ployees of Crown Capital (namely, Mr. Lerner, Jason Ackerman, and

Mr. Deutschman) and Mr. Ackerman assisted Davidson Cotton in

starting a towel manufacturing business in Mexico. The business

operations of Davidson Cotton were ultimately unsuccessful, and

the company was liquidated. Davidson Cotton was able to pay to

Crown Capital only a portion of the fees required by the Davidson

Cotton management services agreement.21

20
Our detailed findings of fact with respect to Mr.
Ackerman’s investment in Davidson Cotton are set forth in the
attached appendix A, which is incorporated herein.
21
The record does not disclose what ultimately happened to
Mr. Ackerman’s investment in Davidson Cotton.
- 22 -

Another major project that Mr. Ackerman pursued involved

assisting a company known as Equity Marketing, Inc. (Equity

Marketing),22 in making certain unidentified acquisitions. In

early 2000, Equity Marketing, through one of Mr. Ackerman’s

former colleagues at Drexel, approached Mr. Ackerman and asked

him to make an investment in the company and to provide advice

with respect to the acquisitions that Equity Marketing was seek-

ing to make. Mr. Ackerman asked Jason Ackerman, Mr. Deutschman,

and Mr. Lerner to perform certain due diligence services in order

to determine whether Equity Marketing was a company in which Mr.

Ackerman should invest.

Sometime before March 22, 2000, Mr. Ackerman decided to

invest in Equity Marketing through Somerville, and on that date

Mr. Ackerman made that investment (discussed in more detail

below). From 2000 to 2008, Mr. Ackerman provided certain advice

to Equity Marketing regarding the acquisitions that it was seek-

ing to make.

On March 22, 2000, Somerville formed Crown Acquisition

Partners, LLC (Crown Acquisition Partners). On March 29, 2000,

Crown Acquisition Partners entered into a securities purchase

agreement (Equity Marketing securities purchase agreement) with

Equity Marketing. That agreement provided that on March 29,

2000, Equity Marketing was to sell to Crown Acquisition for

22
Equity Marketing was a marketing/advertising agency lo-
cated in Los Angeles, Cal.
- 23 -

$11,900,000 (1) certain shares of series A preferred stock in

Equity Marketing, (2) certain warrants to purchase certain shares

of series B preferred stock in Equity Marketing, and (3) certain

warrants to purchase certain shares of series C preferred stock

in Equity Marketing. The Equity Marketing securities purchase

agreement also provided that “as soon as practicable” Equity

Marketing was to sell to Crown Acquisition Partners for

$13,100,000 (1) certain additional shares of series A preferred

stock in Equity Marketing, (2) certain warrants to purchase

certain additional shares of series B preferred stock in Equity

Marketing, and (3) certain warrants to purchase certain addi-

tional shares of series C preferred stock in Equity Marketing.

As part of its agreement to sell to Crown Acquisition Part-

ners certain shares of stock in Equity Marketing and certain

warrants to purchase certain other shares of stock in Equity

Marketing, Equity Marketing agreed to pay to Crown Acquisition

Partners, or any of its affiliates, including Crown Capital, a

total commitment fee of $1,250,000 in 20 quarterly installments

of $62,500. As required by the Equity Marketing securities

purchase agreement, from June 30, 2000, to March 31, 2005, Equity

Marketing paid to Crown Capital that $1,250,000 commitment fee in

20 quarterly installments of $62,500.

On April 28, 2000, Crown Acquisition Partners changed its

name to Crown Emak Partners, LLC (Crown Emak Partners). On a
- 24 -

date not disclosed by the record, Somerville contributed its

interest in Crown Emak Partners to Crown Emak Investments, LLC

(Crown Emak Investments).23 As of June 13, 2000, the members of

Crown Emak Investments were Somerville, Crown Emak Holdings, LLC

(Crown Emak Holdings), and J. Rothschild Nominees (Guernsey)

Limited.24

Crown Emak Investments issued to Somerville Schedule K-1,

Partner’s Share of Income, Credits, Deductions, etc. (Schedule K-

1), for each of Somerville’s taxable years 2000 through 2006.

Each of those schedules showed dividend income paid by Equity

23
As of June 13, 2000, the members of Crown Emak Partners
were Crown Emak Investments, Allen Ba (Mr. Ba), Chris Calise (Mr.
Calise), and Ken Squire (Mr. Squire). Mr. Ba, Mr. Calise, and
Mr. Squire were employed by Crown Capital when they became
members of Crown Emak Partners. Crown Emak Investments, which
was the managing member of Crown Emak Partners, owned a 99.31-
percent interest in Crown Emak Partners, which it had received in
exchange for its contribution to Crown Emak Partners of
$24,828,541.
24
Somerville owned a 79.96-percent interest in Crown Emak
Investments, which it had received in exchange for its contribu-
tion to Crown Emak Investments of $8,090,000 and its interest in
Crown Emak Partners valued at $11,900,000. Crown Emak Holdings
owned a .04-percent interest in Crown Emak Investments, which it
had received in exchange for its contribution to Crown Emak
Investments of $10,000. J. Rothschild Nominees (Guernsey)
Limited owned the remaining 20-percent interest in Crown Emak
Investments, which it had received in exchange for its contribu-
tion to Crown Emak Investments of $5 million.

As of July 17, 2003, the members of Crown Emak Holdings were
Somerville, Jason Ackerman, Mr. Deutschman, Mr. Lerner, Mr.
Squire, Michael Leraris (Mr. Leraris), Suneel Kaji (Mr. Kaji),
and J. Rothschild Nominees (Guernsey) Limited. Jason Ackerman,
Mr. Deutschman, Mr. Lerner, Mr. Squire, Mr. Leraris, and Mr. Kaji
were employees of Crown Capital when they became members of Crown
Emak Holdings.
- 25 -

Marketing to Crown Emak Partners with respect to the preferred

stock that Crown Emak Partners had acquired pursuant to the

Equity Marketing securities purchase agreement. That dividend

income was the only income reported in the Schedule K-1 that

Crown Emak Investments issued to Somerville for each of

Somerville’s taxable years 2001 through 2004.25

Crown Emak Holdings issued to Somerville Schedule K-1 for

each of Somerville’s taxable years 2000 through 2006. Each of

those schedules showed dividend income paid by Equity Marketing

to Crown Emak Partners with respect to the preferred stock that

Crown Emak Partners had acquired pursuant to the Equity Marketing

securities purchase agreement.26

Another major project that Mr. Ackerman pursued involved

starting an Internet grocery business. The initial concept of

25
The respective Schedules K-1 that Crown Emak Investments
issued to Somerville for Somerville’s taxable years 2001 through
2004 are part of the record. The respective Schedules K-1 that
Crown Emak Investments issued to Somerville for Somerville’s
taxable years 2000, 2005, and 2006 are not part of the record.
Thus, we do not know whether there was any income reported in any
of those schedules other than the dividend income paid by Equity
Marketing to Crown Emak Partners with respect to the preferred
stock that Crown Emak Partners had acquired pursuant to the
Equity Marketing securities purchase agreement.
26
The respective Schedules K-1 that Crown Emak Holdings
issued to Somerville for Somerville’s taxable years 2000 through
2006 are not part of the record. Thus, we do not know whether
there was any income reported in any of those schedules other
than the dividend income paid by Equity Marketing to Crown Emak
Partners with respect to the preferred stock that Crown Emak
Partners had acquired pursuant to the Equity Marketing securities
purchase agreement.
- 26 -

that business originated with Jason Ackerman. Beginning around

1999, Mr. Ackerman, Crown Capital under the leadership of Jason

Ackerman, and Joe Fedele, a supermarket executive hired by Mr.

Ackerman and Crown Capital, spent approximately two years in

creating a business plan for an Internet grocery business.

Around 2000, Mr. Ackerman, Crown Capital, and/or Joe Fedele

formed Fresh Direct Holdings, Inc. (Fresh Direct), to operate

that business.

From the formation of Fresh Direct until early 2006, Mr.

Ackerman served as chairman of the board of directors of Fresh

Direct. In early 2006, Mr. Ackerman resigned as chairman of that

board but continued to serve as a member thereof.27

On a date not disclosed by the record, Mr. Ackerman invested

in Fresh Direct by purchasing 83 percent of the shares of stock

in that corporation for a penny a share. Thereafter, Mr.

Ackerman contributed at least certain of those shares to Crown

Fresh Direct, LLC (Crown Fresh Direct), that had been formed by

Somerville on March 1, 2000.28

27
In 2006, Rick Braddock (Mr. Braddock) became the chairman
of the board of directors of Fresh Direct. On a date not dis-
closed by the record before the date on which Mr. Braddock became
the chairman of that board, he had invested in, and entered into
an agreement to provide certain consulting services to, Fresh
Direct.
28
Our detailed findings of fact with respect to the owner-
ship of Crown Fresh Direct and certain other related entities are
set forth in the attached appendix B, which is incorporated
herein.
- 27 -

On a date not disclosed by the record before September 2002,

C. Gregory Earls (Mr. Earls), a well-known businessman in Wash-

ington, D.C., whom Mr. Ackerman had known since 1995 or 1996,29

informed Mr. Ackerman that he had certain clients that would be

interested in investing in Fresh Direct. Thereafter, Mr. Earls

and Mr. Ackerman each attempted to raise funds for that corpora-

tion. Mr. Ackerman successfully raised a substantial amount of

funds for Fresh Direct. Mr. Earls advised Mr. Ackerman to place

those funds in an escrow account in the name of Mr. Earls, which

Mr. Ackerman did. (We shall refer to the funds that Mr. Ackerman

raised for Fresh Direct and placed into that escrow account as

the Fresh Direct investor funds in escrow.)

On April 12, 2000, Crown Capital and Fresh Direct entered

into a management services agreement (Fresh Direct management

services agreement), and on April 29, 2003, they entered into an

amended and restated management services agreement (Fresh Direct

amended management services agreement). Pursuant to those agree-

ments, Crown Capital was to provide to Fresh Direct

advisory and consulting services in relation to the
affairs of * * * [Fresh Direct] in connection with
strategic financial planning, and other services, in-
cluding, without limitation, advisory and consulting
services relating to the selection, supervision and
retention of independent auditors, the selection, re-
tention and supervision of outside legal counsel, and
the selection, retention and supervision of investment
bankers or other financial advisors or consultants.

29
Mr. Ackerman met Mr. Earls when Mr. Ackerman’s son was in
the same class at Harvard University as Mr. Earls’s daughter.
- 28 -

In exchange for the services that Crown Capital provided to Fresh

Direct, Fresh Direct paid to Crown Capital the fees required by

the Fresh Direct management services agreement and the Fresh

Direct amended management services agreement.

During each of the years at issue, Mr. Ackerman, through

Somerville S Trust, made payments to Crown Capital of the funds

that Crown Capital requested in order to assist it in carrying on

its business activities.30 The total amount of payments that Mr.

Ackerman made to Crown Capital during each of those years was:

Year Total Payment
1
1997 $1,954,632
1998 7,300,000
2
2000 6,687,520
3
2002 2,254,747
2004 1,000,000
1
Of the $1,954,632 that Mr. Ackerman paid to Crown Capital
during 1997, $200,000 pertained to a failed attempt to establish
an insurance company.
2
Of the $6,687,520 that Mr. Ackerman paid to Crown Capital
during 2000, $1,827,418 pertained to certain unidentified aban-
doned projects.
3
Of the $2,254,747 that Mr. Ackerman paid to Crown Capital
during 2002, $663,520 pertained to certain unidentified abandoned
projects.

The practice that Crown Capital followed in requesting funds

from Mr. Ackerman was to send an invoice for the funds requested

to Ms. Patriarca, who, as discussed above, handled the bookkeep-

30
The record does not establish how Crown Capital treated
for book and tax purposes the payments that Mr. Ackerman made to
it during each of the years at issue.
- 29 -

ing for Somerville S Trust.31 After obtaining Mr. Ackerman’s

approval, Ms. Patriarca had the funds requested sent to Crown

Capital.

During each of petitioners’ taxable years 1997, 1998, 2000,

and 2002, Mr. Ackerman made payments to Rockport Advisors of

certain funds that it requested.32 The total amount of payments

that Mr. Ackerman paid to Rockport Advisors during each of those

years was:33

Year Total Payment
1997 $587,500
1998 950,000
2000 1,235,876
2002 500,000

During each of the years at issue, Mr. Ackerman did not

provide advisory services with respect to the major projects in

31
The invoices that Crown Capital sent to Ms. Patriarca are
not part of the record.
32
The record not establish how Rockport Advisors treated for
book and tax purposes the payments that Mr. Ackerman made to it
during each of petitioners’ taxable years 1997, 1998, and 2002.
However, we note that the amount of “Gross receipts or sales”
that Rockport Advisors reported in its Form 1120 for its taxable
year 1998 is equal to the total amount of the payments that Mr.
Ackerman made to Rockport Advisors during that year. As for
petitioners’ taxable year 2000, Rockport Advisors booked the
total amount of the payments that Mr. Ackerman made to it during
that year as “ADVISORY FEE INCOME”, and Rockport Advisors re-
ported that amount as “Gross receipts or sales” in its Form 1120
for that year.
33
The record does not disclose any other information regard-
ing Mr. Ackerman’s payments to Rockport Advisors during 1997,
1998, 2000, and 2002. Nor does the record disclose whether Mr.
Ackerman made any payments to Rockport Advisors during petition-
ers’ taxable year 2004.
- 30 -

exchange for a fee or a commission or with the purpose of selling

his interests in the respective companies involved in those

projects in the ordinary course of any business of his. Nor did

Mr. Ackerman provide advisory services with respect to the major

projects during any of those years in exchange for any other

compensation other than the normal investor’s return.

As discussed above, in petitioners’ Schedule C for each of

the years at issue, petitioners showed the “Principal business or

profession, including product or service” as “INVESTMENTS AND

BANKING” and the “Business name” as “PETER ACKERMAN”. Mr.

Ackerman maintained no books and records with respect to the

activity reflected in each of those schedules.

In the 1997 Schedule C, petitioners reported no income in

part I and claimed $2,752,132 as “Other expenses” in part II

consisting of payments of (1) $1,954,632 to Crown Capital,

(2) $587,500 to Rockport Advisors, and (3) $210,000 to Nevada

Media Partners. In that schedule, petitioners claimed a net loss

of $2,752,132. In determining the taxable income reported in the

1997 joint return, petitioners deducted that net loss.

In the 1998 Schedule C, petitioners reported no income in

part I and claimed $8,250,000 as “Other expenses” in part II

consisting of payments of (1) $7,300,000 to Crown Capital and

(2) $950,000 to Rockport Advisors. In that schedule, petitioners

claimed a net loss of $8,250,000. In determining the taxable
- 31 -

income reported in the 1998 joint return, petitioners deducted

that net loss.

In the 2000 Schedule C, petitioners reported no income in

part I and claimed $7,973,649 as “Other expenses” in part II

consisting of (1) $50,253 of expenses for a book that Mr.

Ackerman had coauthored on nonviolent resistance34 (Mr. Ackerman’s

book on nonviolent resistance) and (2) payments of

(a) $6,687,520 to Crown Capital and (b) $1,235,876 to Rockport

Advisors. In that schedule, petitioners claimed a net loss of

$7,973,649. In determining the taxable income reported in the

2000 joint return, petitioners deducted that net loss.

In the 2002 Schedule C, petitioners reported no income in

part I and claimed $2,754,747 as “Other expenses” in part II

consisting of payments of (1) $2,254,747 to Crown Capital and

(2) $500,000 to Rockport Advisors. In that schedule, petitioners

reported a net loss of $2,754,747. In determining the taxable

income reported in the 2002 joint return, petitioners deducted

that net loss.

In the 2004 Schedule C, petitioners reported no income in

part I and claimed $1 million as “Other expenses” in part II

consisting of a payment of that amount to Crown Capital. In that

schedule, petitioners reported a net loss of $1 million. In

34
The $50,253 of expenses pertaining to Mr. Ackerman’s book
on nonviolent resistance consisted of expenses for certain
research and publicity and an unidentified “book purchase”.
- 32 -

determining the taxable income reported in the 2004 joint return,

petitioners deducted that net loss.

In the notice for 1997, 1998, and 2000 and the notice for

2002 and 2004 (collectively, the notices), respondent determined

that (1) the “Other expenses” that petitioners claimed in Sched-

ule C “are not attributable to an active trade or business under

IRC Section 162”, (2) those expenses are deductible as “expenses

related to the production or collection of income under IRC

Section 212 subject to the 2 percent floor for miscellaneous

deductions”, and (3) therefore petitioners should have reported

those expenses in Schedule A--Itemized Deductions (Schedule A)

instead of Schedule C.35

Claimed Deduction for the
Protection of Business Reputation

In 1918, the maternal grandfather of Don Ackerman and of Mr.

Ackerman started a business that was the predecessor of ECC. In

1964, the father of Don Ackerman and of Mr. Ackerman incorporated

ECC, a supplier of wallpaper sample books and sample cards for

paint, rugs, and wood pieces. Around 1965, when the grandfather,

the father, and the uncle of Don Ackerman and of Mr. Ackerman

35
With respect to the payment of $210,000 to Nevada Media
Partners that petitioners deducted in the 1997 Schedule C, the
parties agree that that payment constituted a capital expendi-
ture. They further agree that that $210,000 should not have been
deducted in the 1997 Schedule C but should have been included as
part of Somerville S Trust’s basis in its interest in Santa
Monica.
- 33 -

developed certain health problems, Don Ackerman took over the

management of ECC.

Funds Advanced to ECC

During the early 1990s, ECC operated a successful business.

It generated annual revenue of approximately $25 million and had

approximately 1,500 employees. By 1997, at a time when Don

Ackerman and Jason Ackerman owned ECC,36 that company faced dire

financial circumstances that were due in large part to a reduced

need for wallpaper sample books.

On a date in 1997 not disclosed by the record before May 7,

Don Ackerman approached his brother Mr. Ackerman and informed him

that ECC was unable to meet its payroll obligations, that ECC

and/or Don Ackerman had accrued a substantial amount of bank

debt, and that ECC and Don Ackerman might have to commence a

bankruptcy proceeding.

Mr. Ackerman, who was not a stockholder, guarantor, em-

ployee, or officer of ECC, decided to advance certain funds to

ECC. On the dates indicated, Mr. Ackerman, through Somerville S

Trust, advanced to ECC the following amounts totaling $7,850,000

($7,850,000 of advanced funds):37

36
The record does not disclose when Don Ackerman and Jason
Ackerman acquired their respective stock interests in ECC.
37
Although Mr. Ackerman advanced a total of $7,850,000 to
ECC through Somerville S Trust, in discussing Mr. Ackerman’s
advancing those funds, we shall sometimes for convenience not
(continued...)
- 34 -

Date Amount
5/7/1997 $1,000,000
6/3/1997 1,000,000
7/2/1997 1,000,000
7/30/1997 2,400,000
8/29/1997 500,000
9/26/1997 500,000
10/28/1997 600,000
11/6/1997 100,000
11/21/1997 750,000

ECC never repaid the funds that Mr. Ackerman advanced to it.

Around the time in 1997 Mr. Ackerman had decided to advance,

and was advancing, $7,850,000 to ECC, a decision had been made to

form International Service Investors, LLC (ISI), International

Service Group, LLC (ISG), and International Service Group Hold-

ings, LLC (ISGH),38 in order to continue the operations of ECC in

modified form.39 Around the same time, Mr. Ackerman also decided

37
(...continued)
indicate that Mr. Ackerman advanced those funds through
Somerville S Trust.
38
ISI, ISG, and ISGH were formed on the following dates:

Entity Date of Formation
ISI 8/27/1997
ISG 8/29/1997
ISGH 11/1/1997

39
The parties generally refer to ISI, ISG, and ISGH as the
“International Group”. In describing the activities of the
International Group in their stipulation of facts, the parties do
not make clear whether each of the three companies making up the
International Group engaged in those activities. It appears from
the record that ISG was the only company engaged in manufacturing
(continued...)
- 35 -

to make, and was making, through Somerville an investment of

$18,050,000 in the International Group by investing that amount

in ISI.40 Those funds enabled ISI and the other companies making

up the International Group to conduct their operations.

As of December 31, 1997, Somerville owned a 98-percent

interest, ECC owned a 1-percent interest, and New Cumberland

Corporation, Inc. (New Cumberland),41 owned a 1-percent interest

in ISI. In exchange for the 1-percent interest in ISI that ECC

owned as of December 31, 1997, ECC contributed all of its assets

(discussed below) totaling $15,190,903, but none of its liabili-

ties, to ISI.42 As of December 31, 1997, ISI owned a 1-percent

interest and ISGH, in which ISI owned a 75-percent interest,43

owned a 99-percent interest in ISG.

39
(...continued)
operations. When referring to one or more of the companies
making up the group that the parties refer to as the “Interna-
tional Group”, we shall sometimes for convenience use the termi-
nology that the parties use.
40
The record does not disclose the specific date in 1997 on
which Somerville invested $18,050,000 in ISI.
41
At all relevant times, Don Ackerman owned New Cumberland.
42
As of Dec. 31, 1997, ISI was the sole stockholder of ECC.
The record does not disclose how, or the specific date on which,
ISI acquired its stock interest in ECC.
43
As of Dec. 31, 1997, Jason Ackerman and Mr. Deutschman
each owned a 7-percent interest, New Cumberland owned a 3.75-
percent interest, and Crown Capital owned a 7.25-percent interest
in ISGH.
- 36 -

Included in the assets that ECC contributed to ISI were a

substantial, but undisclosed, amount of cash, substantial amounts

of inventory, certain accounts receivable, certain intangible

assets in the form of customer relationships, certain employee

relationships, certain leasehold interests, and substantial

amounts of machinery and equipment that ECC had used in the

production of sample cards and packaging projects. The assets

that ECC contributed to ISI assisted the International Group in

continuing the operations of ECC in modified form.

After the International Group was formed and received from

Mr. Ackerman, through Somerville, over $18 million and from ECC

over $15 million of assets, the International Group made certain

fundamental changes to ECC’s business model and continued ECC’s

business in modified form. For example, the International Group

engaged in the manufacture of Pokemon cards and the business of

creating packaging for various companies.

From at least 1998 through 2003, Mr. Deutschman managed the

day-to-day business operations of the International Group from

the International Group’s offices in New Jersey. At all relevant

times, the International Group carried out its operations in New

Jersey, New York City, Texas, and/or Mexico. In 1999, at least

certain of the manufacturing operations of the International

Group were moved from New Jersey to Mexico.
- 37 -

Book and Tax Treatment of the $7,850,000 of
Advanced Funds by Somerville and by Santa Monica

At the direction of Mr. Lerner, Somerville S Trust booked

the $7,850,000 of advanced funds as a loan from Somerville S

Trust to ECC. Consistent with Somerville S Trust’s treatment of

the $7,850,000 of advanced funds in its books, ECC booked those

funds as a loan from Somerville S Trust to ECC. In Schedule L,

Balance Sheets per Books (Schedule L), of Form 1120 for each of

its taxable years ended November 30, 1998 (1998 Schedule L), and

November 30, 1999, ECC included the $7,850,000 of advanced funds

as part of its “Other liabilities”.44 In Schedule M-1, Reconcili-

ation of Income (Loss) per Books With Income per Return, of Form

1120 for its taxable year ended November 30, 2000, ECC included

the $7,850,000 of advanced funds as book income from the “CANCEL-

LATION OF DEBT”.

On December 16, 1997, Somerville S Trust contributed to

Somerville a loan receivable (contributed loan receivable) with

respect to the $7,850,000 of advanced funds. Somerville S

Trust’s basis in its interest in Somerville included the value of

that loan receivable, and the contributed loan receivable was

among the assets held by Somerville when Somerville S Trust

contributed its interest in Somerville to Santa Monica on Decem-

ber 29, 1997.

44
In the 1998 Schedule L, ECC incorrectly identified the
amount of the ECC funds as $7,750,000, instead of $7,850,000.
- 38 -

In Schedule L of Form 1065 that it prepared, but did not

file,45 for each of its taxable years 1997, 1998, and 1999,

Somerville included the contributed loan receivable as part of

its “Other current assets”. In Form 1065 that it prepared, but

did not file, for its taxable year 2000, Somerville claimed an

“Ordinary * * * (loss) from trade or business activities” of

$9,171,171 (Somerville’s claimed 2000 ordinary loss). In calcu-

lating that loss, Somerville deducted a bad debt of $7,850,000

with respect to the contributed loan receivable.

On July 2, 2001, Santa Monica, which owned all of

Somerville, filed Form 1065 for its taxable year 2000. In that

form, Santa Monica claimed an “Ordinary * * * (loss) from trade

or business activities” of $10,344,426 (Santa Monica’s claimed

2000 ordinary loss). That ordinary loss that Santa Monica claim-

ed included Somerville’s claimed 2000 ordinary loss.46 Santa

Monica’s claimed 2000 ordinary loss was allocated as follows:

99.88 percent to Somerville S Trust, .059 percent to Rockport

45
See supra note 7.
46
The parties stipulated that Santa Monica’s claimed 2000
ordinary loss included “an ordinary loss in the amount of
$91,171,171 from Somerville LLC.” That stipulation is clearly
contrary to the facts that we have found are established by the
record, and we shall disregard it. See Cal-Maine Foods, Inc. v.
Commissioner, 93 T.C. 181, 195 (1989). The record establishes,
and we have found, that Santa Monica’s claimed 2000 ordinary loss
included Somerville’s claimed 2000 ordinary loss of only
$9,171,171.
- 39 -

Capital, and .059 percent to Perry Lerner.47 In Schedule E of

their 2000 joint return, petitioners reported Somerville S

Trust’s and Rockport Capital’s respective allocable shares of

Santa Monica’s claimed 2000 ordinary loss.48

On or about August 8, 2005, petitioners and respondent

executed Form 872, Consent to Extend the Time to Assess Tax (Form

872), in which they consented to extend to December 31, 2006, the

time within which to assess petitioners’ tax for their taxable

year 2000. That Form 872 did not provide that it applied to any

tax of petitioners attributable to the partnership items of Santa

Monica.

Santa Monica did not execute Form 872-P, Consent to Extend

the Time to Assess Tax Attributable to Partnership Items, with

respect to its taxable year 2000.

In the second amended petition at docket No. 13947-06,

petitioners alleged as an affirmative issue that the $7,850,000

of advanced funds is deductible under section 162(a) for peti-

tioners’ taxable year 1997.

47
Before 2000, Santa Monica, Somerville, and petitioners did
not claim any deductions with respect to the $7,850,000 of
advanced funds.
48
The record does not disclose whether Mr. Lerner reported
in his tax return for his taxable year 2000 his allocable share
of Santa Monica’s claimed 2000 ordinary loss.
- 40 -

Claimed Losses With Respect to ISI

From around early 1998 through 2003, Mr. Deutschman, who

lived in New York City, had a leadership role in each of the

companies (i.e., ISI, ISG, and ISGH) that made up the Interna-

tional Group.49 During each of those years, Mr. Deutschman spent

more than 500 hours managing the day-to-day business operations

of the International Group. Mr. Deutschman performed his manage-

ment activities with respect to the business operations of the

International Group from the International Group’s offices in New

Jersey. No person spent more time managing the business opera-

tions of the International Group than Mr. Deutschman.

During at least 1998 and 2000, Don Ackerman and Jason

Ackerman also provided certain unidentified management services

to the International Group.

Mr. Ackerman, who during the years at issue lived in Wash-

ington, D.C., was not an employee or officer of any of the compa-

nies that made up the International Group, did not receive any

wages from any of those companies, and did not maintain a log

documenting the amount of time that he devoted to any of those

companies.

During 1998 through 2000, Mr. Ackerman communicated on

various occasions with Mr. Deutschman regarding various matters,

49
For example, from 1998 through 2003, Mr. Deutschman served
as president of ISI.
- 41 -

including the business operations and finances of the Interna-

tional Group and various other investments of Mr. Ackerman. Mr.

Deutschman sent Mr. Ackerman at least one memorandum dated July

9, 1999, regarding the business operations of the International

Group that served as a basis for discussions between the two of

them.

During 1998 through 2000, Mr. Ackerman spent at least one or

two days in certain weeks in New York City. During that period,

he also visited New Jersey where his mother and his brother Don

Ackerman lived. While in New York City, Mr. Ackerman spent time

on various matters, including matters relating to certain of the

major projects in which Crown Capital was involved and certain

charitable activities relating to CARE. While in New Jersey, Mr.

Ackerman, inter alia, occasionally visited Mr. Deutschman where

Mr. Deutschman managed the operations of the International Group.

ISI issued to Somerville Schedule K-1 with respect to each

of Somerville’s taxable years 1998 (1998 ISI Schedule K-1 issued

to Somerville) and 2000 (2000 ISI Schedule K-1 issued to

Somerville). In the 1998 ISI Schedule K-1 issued to Somerville,

ISI showed an “Ordinary * * * (loss) from trade or business

activities” of $6,983,996 (1998 ISI loss). In the 2000 ISI

Schedule K-1 issued to Somerville, ISI showed an “Ordinary * * *

(loss) from trade or business activities” of $1,771,427 (2000 ISI

loss).
- 42 -

In the 1998 joint return and the 2000 joint return, peti-

tioners treated Mr. Ackerman’s allocable portions of the respec-

tive 1998 ISI loss and 2000 ISI loss as passive activity losses.

In the second amended petition at docket No. 13947-06, petition-

ers alleged as an affirmative issue that the “losses deducted by

Petitioners as passive losses [with respect to ISI] should be

allowed as active because Mr. Ackerman materially participated in

this business activity throughout the years of the deductions.”

Claimed Theft Loss Deduction

Around 1996 or 1997, Mr. Earls approached Mr. Ackerman with

a proposal to invest in U.S. Technologies, Inc. (U.S. Technolo-

gies), a publicly traded Delaware corporation that used prison

labor to manufacture a variety of products. Mr. Ackerman be-

lieved that such an investment would be profitable.

On June 22, 1998, USV Partners, LLC (USV), was formed for

the purpose of acquiring and holding shares of preferred and

common stock of U.S. Technologies. At all relevant times, Mr.

Earls was the sole director, officer, and employee of USV and

controlled all of its funds.

Pursuant to various subscription agreements, from July 10,

1998, through August 27, 2001, Mr. Ackerman, through Somerville S

Trust, invested funds totaling $4,467,610 in USV. Pursuant to

those agreements, those invested funds were to be used by USV to

purchase shares of common and/or preferred stock in U.S. Technol-
- 43 -

ogies.50 On March 4, 2002, USV distributed to Somerville S Trust

18,759,879 shares of common stock in U.S. Technologies.

Around September 2002, Mr. Ackerman asked Mr. Earls to

return to him the Fresh Direct investor funds in escrow (dis-

cussed above). Mr. Earls was unable to do so because he had

removed from escrow at least certain of those funds. Mr.

Ackerman gave Mr. Earls a deadline by which he had to return to

him the full amount of the Fresh Direct investor funds in escrow.

Mr. Earls borrowed a certain amount of money and returned to Mr.

Ackerman the full amount of those funds by the deadline that Mr.

Ackerman set.

When Mr. Ackerman learned that Mr. Earls had removed from

escrow certain of the Fresh Direct investor funds in escrow, Mr.

Ackerman began to question whether Mr. Earls had properly handled

the funds that Mr. Ackerman, through Somerville S Trust, had

invested in USV. On a date not disclosed by the record before

December 9, 2002, Mr. Ackerman learned that Mr. Earls had used

for his own personal benefit certain of the funds that Mr.

Ackerman, through Somerville S Trust, and other members of USV

had invested in USV. Shortly thereafter, Mr. Ackerman informed a

50
On a date not disclosed by the record, Mr. Lerner also
invested certain funds in USV. Like the funds that Mr. Ackerman,
through Somerville S Trust, invested in USV, the funds that Mr.
Lerner invested in USV were to be used by USV to purchase shares
of common and/or preferred stock in U.S. Technologies.
- 44 -

district attorney in New York51 of Mr. Earls’s conduct with re-

spect to those funds.

On December 9, 2002, in an effort to recover damages of

approximately $5,953,000, Somerville S Trust and certain other

persons who owned interests in USV filed a complaint (December 9,

2002 complaint) in the United States District Court for the

District of Maryland (U.S. District Court for Maryland) against

David Ferreira (Mr. Ferreira) and Ferreira & Isbell, LLC

(Ferreira & Isbell). (We shall refer to that civil action as the

Ferreira litigation.) In the December 9, 2002 complaint, the

plaintiffs in the Ferreira litigation alleged, inter alia, that

the defendants identified in that complaint had “negligently and

recklessly failed to exercise due care in performing their review

of USV’s general ledgers and trial balances, in making any ad-

justments thereto, and in performing other accounting services

for USV.”

On December 18, 2002, criminal complaints were filed against

Mr. Earls in the United States District Court for the Southern

District of New York. Thereafter, on March 24, 2003, Mr. Earls,

who was accused of stealing $13 million of $20 million that had

been invested in USV, was indicted in that court on one count of

51
The record does not disclose which district attorney’s
office in New York Mr. Ackerman informed of Mr. Earls’s conduct
with respect to the funds that Mr. Ackerman, through Somerville S
Trust, and other members of USV had invested in USV.
- 45 -

securities fraud, 19 counts of wire fraud, and two counts of mail

fraud.

On June 17, 2003, Mr. Ackerman executed a formal engagement

letter for representation by the law firm of Jenner & Block, LLC

(Jenner & Block), in connection with the Ferreira litigation and

certain other litigation against Mr. Earls in the Superior Court

of the District of Columbia.

On August 19, 2003, Somerville S Trust entered into three

respective securities and purchase agreements with (1) Mr.

Lerner, (2) WS Investments, LP (WS Investments), and (3) certain

family trusts that were established for the benefit of certain

members of Mr. Ackerman’s family (Ackerman family trusts).52

Pursuant to the securities and purchase agreement entered into by

Somerville S Trust and Mr. Lerner, that trust was to acquire from

Mr. Lerner for a total purchase price of $150,000 (1) any member-

ship interests in USV and shares of stock in U.S. Technologies

that Mr. Lerner owned and (2) any claims that Mr. Lerner had

against Mr. Earls or any of Mr. Earls’s affiliates with respect

to any fraudulent conduct of Mr. Earls concerning those member-

ship interests and shares of stock. Pursuant to the securities

and purchase agreement entered into by Somerville S Trust and WS

52
On a date not disclosed by the record before Mr.
Ackerman’s discovery of Mr. Earls’s conduct with respect to the
funds invested in USV, Somerville S Trust had transferred as
gifts small portions of its USV membership interest to the
Ackerman family trusts.
- 46 -

Investments, that trust was to acquire from WS Investments for a

total purchase price of $200,000 (1) any membership interests in

USV and shares of stock in U.S. Technologies that WS Investments

owned and (2) any claims that WS Investments had against Mr.

Earls or any of Mr. Earls’s affiliates with respect to any fraud-

ulent conduct of Mr. Earls concerning those membership interests

and shares of stock. Pursuant to the securities and purchase

agreement entered into by Somerville S Trust and the Ackerman

family trusts, Somerville S Trust was to acquire from those

family trusts for a total purchase price of $50,000 (1) any

membership interests in USV and shares of stock in U.S. Technolo-

gies that the Ackerman family trusts owned and (2) any claims

that the Ackerman family trusts had against Mr. Earls or any of

Mr. Earls’s affiliates with respect to any fraudulent conduct of

Mr. Earls concerning those membership interests and shares of

stock.

On August 21, 2003, in an effort to recover damages of at

least $5,952,860, Somerville S Trust, which was represented by

Jenner & Block, filed a complaint (August 21, 2003 complaint) in

the United States District Court for the District of Columbia

(U.S. District Court for the District of Columbia) against, inter

alia, Mr. Earls, USV Partners, and U.S. Technologies. The claims

set forth in the August 21, 2003 complaint included the claims

that were assigned to Somerville S Trust by Mr. Lerner, WS In-
- 47 -

vestments, and the Ackerman family trusts pursuant to the respec-

tive securities and purchase agreements described above.

Somerville S Trust alleged in that complaint, inter alia, that

Mr. Earls had “devised and implemented a fraudulent investment

scheme by which he embezzled and misappropriated funds from

investors for his own personal benefit.”

On November 26, 2003, the parties involved in the Ferreira

litigation filed a stipulation of dismissal in the U.S. District

Court for Maryland.

By letter dated March 19, 2004, Jenner & Block sent Mr.

Ackerman a check in the amount of $1,882.73, which had been

recovered from a personal bank account of Mr. Earls. In that

letter, Jenner & Block advised Mr. Ackerman that “We have re-

cently served additional subpoenas and attachment orders on

various banks where Earls had or has accounts”.

On April 23, 2004, Mr. Earls was convicted on all 22 counts

on which he had been indicted on March 24, 2003, and was sen-

tenced to prison for ten years.

By letter dated January 11, 2005, Jenner & Block sent Mr.

Ackerman a check in the amount of $772.86, which had been recov-

ered from another personal bank account of Mr. Earls. In that

letter, Jenner & Block advised Mr. Ackerman of the difficulties

and prohibitive costs of recovering any more funds from that

account.
- 48 -

On a date not disclosed by the record, Somerville S Trust

received a memorandum dated February 14, 2005, that had been sent

to the common shareholders of U.S. Technologies by an individual

named Adam Joseph (Mr. Joseph).53 Mr. Joseph concluded in that

memorandum: “Given the outstanding liabilities of the company

and the illiquid state of the remaining investment portfolio, I

am not optimistic that * * * [U.S. Technologies] shareholders

will realize value.”

On May 26, 2005, Somerville S Trust filed a motion to dis-

miss the August 21, 2003 complaint against Mr. Earls, USV Part-

ners, and U.S. Technologies.54 On June 6, 2005, the U.S. District

Court for the District of Columbia granted that motion.

From around 2002 through 2005, petitioners paid more than

$2.2 million in legal and investigative fees pursuing recovery of

any losses sustained as a result of any fraudulent conduct of Mr.

Earls with respect to the funds invested in USV.

In the 2002 joint return, petitioners claimed a long-term

capital loss of $4,467,610 with respect to the funds that Mr.

Ackerman, through Somerville S Trust, invested in USV. In the

53
The record does not disclose any other information regard-
ing Mr. Joseph.
54
As discussed above, Somerville S Trust alleged in the
August 21, 2003 complaint, inter alia, that Mr. Earls had “de-
vised and implemented a fraudulent investment scheme by which he
embezzled and misappropriated funds from investors for his own
personal benefit.”
- 49 -

2004 joint return, petitioners again claimed a long-term capital

loss in the same amount with respect to that investment.

In the notice for 2002 and 2004, respondent did not make any

determinations regarding the long-term capital loss of $4,467,610

that petitioners claimed in both the 2002 joint return and the

2004 joint return with respect to the funds that Mr. Ackerman,

through Somerville S Trust, invested in USV. In the amended

petition at docket No. 26400-06, petitioners acknowledged that

they are not entitled to deduct that long-term capital loss for

both of their taxable years 2002 and 2004. In that amended

petition, petitioners further alleged as an affirmative issue

that the long-term capital loss that they claimed in both the

2002 joint return and the 2004 joint return with respect to the

funds that Mr. Ackerman, through Somerville S Trust, invested in

USV is “deductible as a theft loss” for their taxable year 2002.

Accuracy-Related Penalty Under Section 6662(a)

Joseph Miller (Mr. Miller) prepared petitioners’ joint

return for each of the years at issue. Ms. Patriarca was respon-

sible for sending to Mr. Miller certain records and schedules

that were pertinent to the preparation of each of those returns.

Grant Thornton, LLP (Grant Thornton), prepared the respec-

tive tax returns of Somerville, Santa Monica, and Crown Capital

for each of the years at issue.
- 50 -

In February 2001, respondent began an examination of peti-

tioners’ taxable years 1997, 1998, and 2000 (examination of 1997,

1998, and 2000). The only issue involved in that examination was

whether the “Other expenses” that petitioners claimed in Schedule

C for each of their taxable years 1997, 1998, and 2000 should

have been claimed in Schedule A instead of Schedule C.

Howard Levinton (Mr. Levinton), an accountant who has been

employed by Grant Thornton since 1987, represented petitioners

with respect to the examination of their taxable years 1997,

1998, and 2000. Mr. Levinton presented to respondent’s revenue

agent (revenue agent) who was assigned to that examination cer-

tain information that that agent requested.

During the examination of 1997, 1998, and 2000, Mr. Levinton

also presented to the revenue agent an amended joint return for

petitioners’ taxable year 1999 (1999 amended joint return). In

that amended return, petitioners claimed a refund of $1,857,106.

Petitioners included Schedule C as part of the 1999 amended joint

return (1999 Schedule C). In that schedule, petitioners showed

the “Principal business or profession, including product or

service” as “INVESTMENTS AND BANKING” and the “Business name” as

“PETER ACKERMAN”. In the 1999 Schedule C, petitioners made no

entries in the section entitled “Income” and claimed “Other

expenses” of $9,694,269 consisting of “INVESTMENT ADVISORY FEES”

of that amount. Petitioners explained in the 1999 amended joint
- 51 -

return that “TAXPAYERS INCORRECTLY DEDUCTED INVESTMENT ADVISORY

FEES AS AN ITEMIZED DEDUCTION RATHER THAN DEDUCTING THEM AS A

TRADE OR BUSINESS EXPENSE ON SCHEDULE C.”55

Around September 2002, respondent issued to petitioners a

30-day letter with respect to their taxable years 1997, 1998, and

2000 (respondent’s 30-day letter). In October 2002, Mr.

Levinton, on petitioners’ behalf, appealed to respondent’s Ap-

peals Office (Appeals Office) the adjustments proposed in that

letter (petitioners’ appeal). Mr. Levinton continued to repre-

sent petitioners throughout that appeal process.

Around early 2005, over a year after petitioners filed the

2002 joint return on November 21, 2003, Mr. Levinton informed Mr.

Lerner of respondent’s position with respect to petitioners’

claimed Schedule C expenses for 1997, 1998, and 2000. Sometime

thereafter in 2005, Mr. Levinton asked Mr. Lerner to accompany

Mr. Levinton to a conference with the Appeals Office (Appeals

Office conference) regarding the adjustments proposed in respon-

dent’s 30-day letter with respect to those years.56

55
In view of respondent’s position on the claimed Schedule C
deductions that are at issue in these cases, we presume that
respondent did not approve the refund that petitioners claimed in
the 1999 amended joint return.
56
The Appeals Office conference that Mr. Levinton asked Mr.
Lerner to attend was rescheduled from a date in 2005 not dis-
closed by the record to a date in December 2005 not disclosed by
the record.
- 52 -

Mr. Ackerman had discussions with Mr. Levinton and Mr.

Lerner regarding the propriety of petitioners’ claimed Schedule C

deductions. Mr. Ackerman had those discussions (1) with Mr.

Levinton on a date not disclosed by the record after respondent

began the examination of 1997, 1998, and 2000 but before peti-

tioners filed the 2002 joint return and (2) with Mr. Lerner57 on a

date in 2005 not disclosed by the record after Mr. Levinton

informed him about respondent’s position with respect to peti-

tioners’ claimed Schedule C deductions for 1997, 1998, and 2000

and over a year after petitioners filed the 2002 joint return.

When Mr. Ackerman discussed the propriety of petitioners’

claimed Schedule C deductions with Mr. Levinton and Mr. Lerner,

he informed them that the expenses for which petitioners claimed

those deductions were “for my business” and “Basically to create

business, to create revenue”. Based upon what Mr. Ackerman told

them, Mr. Levinton and Mr. Lerner advised Mr. Ackerman that they

believed that petitioners’ claimed Schedule C deductions were

proper.

In December 2005, the Appeals Office held the Appeals Office

conference with Mr. Levinton and Mr. Lerner regarding the adjust-

57
It is not clear from the record whether Mr. Levinton was
present at the discussions that Mr. Ackerman had with Mr. Lerner
regarding the propriety of petitioners’ claimed Schedule C
deductions.
- 53 -

ments proposed in respondent’s 30-day letter with respect to

petitioners’ taxable years 1997, 1998, and 2000.

At a time not disclosed by the record before November 17,

2006, respondent began an examination of petitioners’ taxable

years 2002 and 2004. Neither Mr. Levinton nor Mr. Lerner was

involved in that examination.

As discussed above, in the notice for 1997, 1998, and 2000

and the notice for 2002 and 2004, respondent determined (1) that

petitioners’ claimed Schedule C expenses “are not attributable to

an active trade or business under IRC Section 162”, (2) that

those expenses are deductible under section 212 subject to the 2-

percent floor imposed by section 67(a), and (3) that therefore

petitioners should have reported those expenses in Schedule A

instead of Schedule C. In the notice for 2002 and 2004, respon-

dent also determined that petitioners are liable for each of

their taxable years 2002 and 2004 for the accuracy-related pen-

alty under section 6662(a).58 The respective accuracy-related

penalties under section 6662(a) that respondent determined for

petitioners’ taxable years 2002 and 2004 are imposed on respec-

tive underpayments for those years that are attributable solely

to respondent’s disallowance of petitioners’ respective Schedule

58
In the notice for 1997, 1998, and 2000, respondent did not
determine that petitioners are liable for the accuracy-related
penalty under sec. 6662(a).
- 54 -

C deductions claimed in the 2002 joint return and the 2004 joint

return.

OPINION

Burden of Proof

Petitioners do not dispute that they bear the burden of

proof with respect to (1) the affirmative issues that they raised

in the pleadings and that remain at issue and (2) the determina-

tions in the notice for 2002 and 2004 to impose the accuracy-

related penalty. Nor do petitioners dispute that they bear the

burden of proof with respect to the determinations in the notices

to disallow their claimed Schedule C deductions. See Rule

142(a); Welch v. Helvering, 290 U.S. 111, 115 (1933). Petition-

ers argue, however, that the burden of proof with respect to the

determinations to disallow those claimed deductions shifts to

respondent under section 7491(a).

In order for the burden of proof to shift to the Commis-

sioner of Internal Revenue under section 7491(a), the taxpayer

must (1) provide credible evidence with respect to any factual

issue relevant to determining the tax liability of the taxpayer

and (2) comply with the applicable requirements of section

7491(a)(2). Although section 7491(a) does not define the term

“credible evidence”, the legislative history of the statute does.

The legislative history of section 7491(a) states in pertinent

part:
- 55 -

Credible evidence is the quality of evidence which,
after critical analysis, the court would find suffi-
cient upon which to base a decision on the issue if no
contrary evidence were submitted (without regard to the
judicial presumption of IRS correctness). * * * The
introduction of evidence will not meet this standard if
the court is not convinced that it is worthy of belief.
* * *

H. Conf. Rept. 105-599, at 240-241 (1998), 1998-3 C.B. 747, 994-

995.

In support of their argument that the burden of proof shifts

to respondent under section 7491(a) with respect to the determi-

nations in the notices to disallow their claimed Schedule C

deductions, petitioners assert:

The extensive testimony of Mr. Ackerman and others
about his Schedule C activity certainly constitutes
“credible evidence” with respect to all pertinent fac-
tual issues. No expense was challenged for lack of
substantiation or failure to maintain records. * * *
Accordingly, the burden of proof on this issue should
shift to respondent. * * *

Respondent counters that

Petitioners rely heavily on the testimony of petitioner
and related individuals, much of which was overly
broad, vague, misleading, and uncorroborated by any
documentary evidence. This testimony does not consti-
tute credible evidence under section 7491(a)(1). * * *
Furthermore, section 7491(a)(2) specifies certain re-
quirements that must be met before section 7491(a)(1)
can apply. Specifically, the taxpayer must have main-
tained all records required by the Internal Revenue
Code. I.R.C. § 7491(a)(2)(B). * * * Petitioner did not
maintain any books or records with respect to his
Schedule C activity. * * *

As discussed below, there are material factual issues rele-

vant to determining whether petitioners are entitled under sec-
- 56 -

tion 162(a) to their claimed Schedule C deductions as to which

they have not introduced credible evidence within the meaning of

section 7491(a)(1).59

On the record before us, we find that the burden of proof

does not shift to respondent under section 7491(a) with respect

to any factual issues that pertain to the Schedule C deductions

that petitioners are claiming for each of the years at issue.

Evaluation of Evidence on Which Petitioners Rely

Petitioners rely on certain testimonial evidence and certain

documentary evidence in order to satisfy their burden of proof

with respect to each of the issues presented.

Testimonial Evidence

The testimonial evidence on which petitioners rely is the

respective testimonies of Mr. Ackerman, Mr. Lerner, Jason

Ackerman, Don Ackerman, Mr. Deutschman, Mr. Levinton, Mr.

Braddock, and Ms. Patriarca.

59
Assuming arguendo that petitioners had introduced credible
evidence within the meaning of sec. 7491(a)(1) with respect to
the factual issues relevant to determining whether petitioners
are entitled under sec. 162(a) to their claimed Schedule C
deductions, the burden of proof with respect to that issue
nonetheless would not shift to respondent under sec. 7491(a)(1).
That is because we have found that Mr. Ackerman maintained no
books and records with respect to the activity reflected in
petitioners’ Schedule C for each of the years at issue. See sec.
7491(a)(2)(B).
- 57 -

Mr. Ackerman’s Testimony

We found the testimony of Mr. Ackerman to be in certain

material respects general, conclusory, vague, ambiguous, confus-

ing, questionable, self-serving, and/or evasive. We shall not

rely on Mr. Ackerman’s testimony to establish petitioners’ re-

spective positions on the various issues to which that testimony

pertained.

Mr. Lerner’s Testimony

We found the testimony of Mr. Lerner to be in certain mate-

rial respects vague, ambiguous, questionable, and/or serving the

interests of his longtime associate Mr. Ackerman, who retained

Mr. Lerner to provide certain legal services for him and who

played a significant role in enabling Mr. Lerner to be employed

by Crown Capital. We shall not rely on Mr. Lerner’s testimony to

establish petitioners’ respective positions on the various issues

to which that testimony pertained.

Don Ackerman’s Testimony

We found the testimony of Don Ackerman to be in certain

material respects general, conclusory, vague, ambiguous, ques-

tionable, and/or serving the interests of his brother Mr.

Ackerman, who played a significant role in enabling Don Ackerman

to be employed by Crown Capital after the business of ECC that

Don Ackerman was managing began facing dire financial circum-
- 58 -

stances.60 We shall not rely on Don Ackerman’s testimony to

establish petitioners’ respective positions on the various issues

to which that testimony pertained.

Jason Ackerman’s Testimony

We found the testimony of Jason Ackerman to be in certain

material respects vague, ambiguous, questionable, and/or serving

the interests of his uncle and longtime associate Mr. Ackerman,

who played a significant role in enabling Jason Ackerman to be

employed by Crown Capital. We shall not rely on Jason Ackerman’s

testimony to establish petitioners’ respective positions on the

various issues to which that testimony pertained.

Mr. Deutschman’s Testimony

We found the testimony of Mr. Deutschman to be in certain

material respects vague, ambiguous, questionable, and/or serving

the interests of his longtime associate Mr. Ackerman, who played

a significant role in enabling Mr. Deutschman to be employed by

Crown Capital. We shall not rely on that testimony to establish

petitioners’ respective positions on the various issues to which

that testimony pertained.

Ms. Patriarca’s Testimony

We generally found the testimony of Ms. Patriarca to be

credible. However, that testimony, together with other reliable

60
See supra note 12.
- 59 -

evidence in the record, did not enable us to sustain petitioners’

position on any of the issues to which that testimony pertained.

Mr. Braddock’s Testimony

We generally found the testimony of Mr. Braddock to be

credible. However, that testimony, together with other reliable

evidence in the record, did not enable us to sustain petitioners’

position on the issue to which that testimony pertained.

Mr. Levinton’s Testimony

We found the testimony of Mr. Levinton to be questionable in

certain material respects. We shall not rely on Mr. Levinton’s

testimony to establish petitioners’ respective positions on the

various issues to which that testimony pertained.

Documentary Evidence

The documentary evidence on which petitioners rely includes,

inter alia, the notices, the respective tax returns of petition-

ers and certain entities that petitioners directly or indirectly

owned, certain written agreements,61 certain travel itineraries of

Mr. Ackerman, and certain newspaper articles regarding Mr. Earls.

Although the documentary evidence on which petitioners rely is

voluminous, that documentary evidence, together with the reliable

61
The written agreements on which petitioners rely include,
inter alia, the Equity Marketing securities purchase agreement
and certain management service agreements entered into between
Crown Capital and each of certain corporations in which Mr.
Ackerman invested.
- 60 -

testimonial evidence in the record, did not enable us to sustain

petitioners’ position on any of the issues presented.

Claimed Business Expense Deductions

It is petitioners’ position that the claimed Schedule C

expenses that remain at issue are deductible under section

162(a).62 In support of that position, petitioners argue that Mr.

Ackerman incurred those expenses in carrying on the business of

advising companies about their finances and management.63

It is respondent’s position that the claimed Schedule C

expenses that remain at issue are deductible under section 212(1)

and that therefore those expenses are subject to the 2-percent

floor imposed by section 67(a). In support of that position,

respondent argues that Mr. Ackerman incurred the claimed Schedule

62
Virtually all of the expenses that petitioners claimed in
Schedule C for each of their taxable years 1997, 1998, 2000,
2002, and 2004 and that remain at issue, see supra note 35,
consist of payments that Mr. Ackerman made during each of those
years to Rockport Advisors and/or Crown Capital. The only
expenses that remain at issue and that do not consist of payments
to Rockport Advisors and/or Crown Capital are $50,253 of expenses
for Mr. Ackerman’s book on nonviolent resistance that petitioners
claimed in the 2000 Schedule C. See supra note 34. The parties
agree, and we have found, that petitioners paid $50,253 of
expenses for that book. However, petitioners make no argument as
to why they are entitled for their taxable year 2000 to deduct
those expenses under sec. 162(a). We conclude that petitioners
have abandoned that argument.
63
For convenience, we shall sometimes refer to Mr.
Ackerman’s claimed business of advising companies about their
finances and management as the alleged business of providing
advisory services.
- 61 -

C expenses that remain at issue as an investor and not in carry-

ing on a trade or business within the meaning of section 162(a).

Section 162(a) generally allows a deduction for ordinary and

necessary expenses paid or incurred during the taxable year in

carrying on any trade or business. Section 212(1) allows an

individual a deduction for ordinary and necessary expenses paid

or incurred during the taxable year for the production or collec-

tion of income.

In support of their claim that during each of the years at

issue Mr. Ackerman was engaged in the business of advising compa-

nies about their finances and management, petitioners presented

evidence with respect to the major projects64 and advance what we

understand to be two arguments.65 We address each of those argu-

ments below.

Petitioners’ Cost Company or Agency Argument

As we understand it, petitioners are arguing that during

each of the years at issue Rockport Advisors and/or Crown Capital

were cost companies and/or agents of Mr. Ackerman. Consequently,

64
See supra note 15. The record does not disclose what
portion of petitioners’ claimed Schedule C deductions for each of
the years at issue that remains at issue pertained to the major
projects.
65
We found petitioners’ arguments on brief in support of
their position that during each of the years at issue Mr.
Ackerman was engaged in the business of providing advisory
services and that therefore the claimed Schedule C expenses are
deductible under sec. 162(a) to be confusing. We state our
understanding of those arguments.
- 62 -

according to petitioners, they are entitled for each of the years

at issue to deduct under section 162(a) the respective payments

that Mr. Ackerman made during each of those years to Rockport

Advisors and/or Crown Capital. It is not clear from petitioners’

briefs whether petitioners are arguing (1) that during each of

the years at issue Rockport Advisors and/or Crown Capital were

cost companies of Mr. Ackerman and that therefore those companies

were his agents or (2) that during each of those years Rockport

Advisors and/or Crown Capital were Mr. Ackerman’s agents regard-

less of whether they were cost companies of Mr. Ackerman. On the

record before us, we reject both arguments.

We turn first to whether, as petitioners appear to be argu-

ing, Rockport Advisors and/or Crown Capital were cost companies

of Mr. Ackerman and that therefore those companies were his

agents during each of the years at issue. In support of that

argument, petitioners rely on Revenue Ruling 56-542, 1956-2 C.B.

327 (Revenue Ruling 56-542). In that ruling, the Internal Reve-

nue Service (Service) concluded that the stockholders of a cap-

tive mining company (mining company) that had been established as

a cost company were entitled to certain depletion deductions

under section 611 of the Internal Revenue Code of 1954.

In Revenue Ruling 77-1, 1977-1 C.B. 161 (Revenue Ruling 77-

1), the Service revoked Revenue Ruling 56-542. As a result,

petitioners’ reliance on Revenue Ruling 56-542 is misplaced. In
- 63 -

Revenue Ruling 77-1, the Service concluded that “all corporations

operating as cost companies” within the meaning of Revenue Ruling

56-542 “will be treated as separate taxpayers and will be re-

quired to compute their own income, deductions, credits and tax

liabilities.” Rev. Rul. 77-1, 1977-1 C.B. at 161.

Even if the Service had not revoked Revenue Ruling 56-542 in

Revenue Ruling 77-1, we nonetheless would, and do, conclude that

petitioners’ reliance on Revenue Ruling 56-542 is misplaced.

That is because the facts that we have found on the record before

us are materially distinguishable from the facts involved in

Revenue Ruling 56-542. Revenue Ruling 56-542 described the facts

involved therein as follows:

Certain manufacturing corporations, which require for
their normal operations several grades and several
kinds of ore, unite and join with other manufacturers
in an arrangement for the acquisition, by fee or lease,
of mining property and for the exploration, development
and operation of such property. The manufacturers
organize a corporation to own and operate the property,
subscribe to the corporation’s capital stock, and ad-
vance all funds needed both for capital and operative
purposes. The mining company, referred to as a ‘cost
company,’ executes a contract with its stockholding
manufacturing corporations. The contract provides
essentially that the participants, each in proportion
to its stock ownership, shall advance all funds, both
capital and operative, necessary for the mining company
to operate and shall share in the same proportion in
the ore produced. Under an agreement signed with its
stockholding manufacturing corporations, the mining
company will not sell any ore and will have no net
income. Its operations, as well as the disposition of
the products mined, will at all times be under the
control of the participants.
- 64 -

Thus, the basic issue for consideration is whether
the economic interest in the ore thus being produced,
with the resultant right to claim depletion, is in the
captive mining company or its stockholding corpora-
tions.

Rev. Rul. 56-542, 1956-2 C.B. at 327.

In concluding in Revenue Ruling 56-542 that the stockholders

of the mining company involved therein were entitled to certain

depletion deductions under section 611 of the Internal Revenue

Code of 1954, the Service indicated that the mining company must

“file a corporate return showing no income and no deductions on

its face, but containing schedules showing the gross income and

deductions allocable” to its stockholders.

Although during each of the years at issue Mr. Ackerman made

certain payments to Rockport Advisors and/or Crown Capital, Mr.

Ackerman was not a stockholder of those entities. Moreover,

Rockport Advisors and Crown Capital did not file tax returns as

cost companies described in Revenue Ruling 56-542 in which they

claimed no income and no deductions. Instead, (1) Rockport

Advisors filed Form 1120 for each of its taxable years 1997,

1998, and 200066 in which it reported income and deductions that

were attributable to its business activities, and (2) Crown

Capital filed Form 1120 for its taxable year 1997 and Form 1120S

66
See supra note 10.
- 65 -

for each of its taxable years 1998 and 200067 in which it reported

income and deductions that were attributable to its business

activities.68

On the record before us, we find that petitioners have

failed to carry their burden of establishing that during each of

the years at issue Rockport Advisors and/or Crown Capital were

cost companies of Mr. Ackerman.

We turn now to whether, as petitioners appear to be arguing,

Rockport Advisors and/or Crown Capital were Mr. Ackerman’s agents

during each of the years at issue regardless of whether they were

cost companies of Mr. Ackerman. Petitioners state: “A taxpayer

may deduct payments for business expenses made by * * * his agent

on his behalf.”69 In support of that statement, petitioners cite,

67
See supra note 13.
68
Petitioners also rely on Kenco Rests., Inc. v. Commis-
sioner, T.C. Memo. 1998-342, affd. 206 F.3d 588 (6th Cir. 2000),
for the proposition that the “concept of centralizing costs for
several projects in one entity still exists.” Petitioners’
reliance on that case is misplaced. Unlike the instant case,
Kenco Rests., Inc. involved the reallocation under sec. 482 of
deductions claimed by commonly controlled corporations, one of
which had been established as a “cost company” that provided
management and administrative support services to the remaining
commonly controlled corporations there involved. Moreover, the
“cost company” involved in Kenco Rests., Inc. is materially
distinguishable from the cost company described in Rev. Rul. 56-
542, 1956-2 C.B. 327.
69
However, in these cases petitioners did not claim as
Schedule C deductions the respective expenses that Rockport
Advisors and/or Crown Capital incurred during each of the years
at issue. Instead, petitioners claimed as Schedule C deductions
(continued...)
- 66 -

inter alia, Commissioner v. Bollinger, 485 U.S. 340 (1988), in

which the Supreme Court of the United States (Supreme Court)

discussed and applied the four indicia and two requirements of

corporate agency (discussed below).70 Although petitioners cite

Bollinger, they do not analyze and apply those indicia and re-

quirements to Rockport Advisors and to Crown Capital.71

Before turning to Commissioner v. Bollinger, supra, we shall

consider Natl. Carbide Corp. v. Commissioner, 336 U.S. 422

(1949), the seminal case of the Supreme Court addressing how to

determine the existence of a corporate agency. In addressing

69
(...continued)
in the joint return for each of the years at issue certain
payments that Mr. Ackerman made during each of those years to
Rockport Advisors and/or Crown Capital, and Rockport Advisors
and/or Crown Capital claimed as deductions in their respective
tax returns the respective expenses that they incurred during
each of those years.
70
In support of their statement that “A taxpayer may deduct
payments for business expenses made by * * * his agent on his
behalf”, petitioners also cite, inter alia, N.Y. Guandong Fin.,
Inc. v. Commissioner, T.C. Memo. 2008-62. In that case, we
discussed and applied the four indicia and two requirements of
corporate agency that the Supreme Court discussed and applied in
Commissioner v. Bollinger, 485 U.S. 340, 346-347 (1988). We
concluded in N.Y. Guandong Fin., Inc., that the facts therein did
not establish the existence of a corporate agency.
71
In advancing what appears to be petitioners’ argument that
Rockport Advisors and/or Crown Capital were cost companies of Mr.
Ackerman and that therefore those companies were his agents
during each of the years at issue, petitioners claim that “Crown
[Capital] operated for the account of Mr. Ackerman”. If the
record had established that “Crown [Capital] operated for the
account of Mr. Ackerman”, which we find it does not, as discussed
below, that alleged fact would have been an indicium of agency.
- 67 -

that issue, the Supreme Court set forth the following four indi-

cia and two requirements that are to be considered in making such

a determination:

Whether the corporation operates in the name and for
the account of the principal, binds the principal by
its actions, transmits money received to the principal,
and whether receipt of income is attributable to the
services of employees of the principal and to assets
belonging to the principal are some of the relevant
considerations in determining whether a true agency
exists. If the corporation is a true agent, its rela-
tions with its principal must not be dependent upon the
fact that it is owned by the principal, if such is the
case. Its business purpose must be the carrying on of
the normal duties of an agent. * * * [Fn. refs. omit-
ted.]

Id. at 437. (The above-quoted indicia and requirements of corpo-

rate agency are commonly referred to, and we shall refer to them,

as the six National Carbide factors.) In Natl. Carbide Corp.,

the Supreme Court applied the six National Carbide factors and

concluded that the facts therein did not establish the existence

of a corporate agency.

In Commissioner v. Bollinger, supra, the Supreme Court again

addressed how to determine whether a corporate agency exists. In

addressing that issue, the Supreme Court restated the six Na-

tional Carbide factors, id. at 346-347, and observed that those

factors are designed to ensure “the genuineness of the agency

relationship”, id. at 349. According to the Supreme Court,

the genuineness of the agency relationship is ad-
equately assured * * * when the fact that the corpora-
tion is acting as agent for its shareholders with re-
spect to a particular asset is set forth in a written
- 68 -

agreement at the time the asset is acquired, the corpo-
ration functions as agent and not principal with re-
spect to the asset for all purposes, and the corpora-
tion is held out as the agent and not principal in all
dealings with third parties relating to the asset.
* * *

Id. at 349-350. In Bollinger, the Supreme Court concluded that

the facts therein established “the genuineness of the agency

relationship”. Id.

In order to determine whether Rockport Advisors and/or Crown

Capital were Mr. Ackerman’s agents during each of the years at

issue, we shall apply and analyze the six National Carbide fac-

tors. We turn first to Rockport Advisors. As discussed above,

the record is very sparse as to the activities of Rockport Advi-

sors during each of the years at issue,72 including 1997, 1998,

2000, and 2002, the only years in which Mr. Ackerman made certain

payments to that company that petitioners claimed as expenses in

their respective Schedules C for those years.73 We note initially

that the requirement included as one of the six National Carbide

factors that the corporation’s “relations with its principal must

not be dependent upon the fact that it is owned by the princi-

pal”, Natl. Carbide Corp. v. Commissioner, supra at 437, is

irrelevant to our resolving whether Rockport Advisors was Mr.

Ackerman’s agent during each of petitioners’ taxable years 1997,

72
See supra note 9.
73
See supra note 33.
- 69 -

1998, 2000, and 2002. That is because the parties do not dispute

that during each of those years Mr. Ackerman did not have an

ownership interest in Rockport Advisors. See Shenker v. Commis-

sioner, 804 F.2d 109, 113 (8th Cir. 1986), affg. T.C. Memo. 1985-

301.

With respect to the remaining five National Carbide factors,

on the record before us, we find that petitioners have failed to

carry their burden of establishing that during each of their

taxable years 1997, 1998, 2000, and 2002 (1) Rockport Advisors

acted in the name, and for the account, of Mr. Ackerman; (2)

Rockport Advisors bound Mr. Ackerman by its actions; (3) Rockport

Advisors transmitted money received to Mr. Ackerman; (4) the

receipt of income by Rockport Advisors was attributable to the

services of the employees of Mr. Ackerman and the assets belong-

ing to Mr. Ackerman; or (5) the business purpose of Rockport

Advisors was the carrying on of the normal duties of an agent.

On the record before us, we find that petitioners have

failed to carry their burden of establishing that during each of

petitioners’ taxable years 1997, 1998, 2000, and 2002 Rockport

Advisors was Mr. Ackerman’s agent.

We turn now to Crown Capital. We note initially that, as

was true with respect to Rockport Advisors, the requirement

included as one of the six National Carbide factors that the

corporation’s “relations with its principal must not be dependent
- 70 -

upon the fact that it is owned by the principal”, Natl. Carbide

Corp. v. Commissioner, 336 U.S. at 437, is irrelevant to our

resolving whether Crown Capital was Mr. Ackerman’s agent during

each of the years at issue. That is because the parties do not

dispute that during each of those years Mr. Ackerman did not have

an ownership interest in Crown Capital. See Shenker v. Commis-

sioner, supra at 113.

With respect to the remaining five National Carbide factors,

on the record before us, we find that petitioners have failed to

carry their burden of establishing that during each of the years

at issue (1) Crown Capital acted in the name, and for the ac-

count, of Mr. Ackerman;74 (2) Crown Capital bound Mr. Ackerman by

its actions; (3) Crown Capital transmitted money received to Mr.

Ackerman; (4) the receipt of income by Crown Capital was attrib-

utable to the services of the employees of Mr. Ackerman and the

assets belonging to Mr. Ackerman;75 or (5) the business purpose of

Crown Capital was the carrying on of the normal duties of an

agent.76

74
See supra note 71.
75
Although Mr. Ackerman paid Crown Capital the funds that it
requested in order to assist it in carrying on its business
activities, after he did, those funds became the funds of Crown
Capital and no longer belonged to Mr. Ackerman.
76
Moreover, on the record before us, we find that petition-
ers did not establish the following facts that would have been
helpful in ensuring “the genuineness of the [claimed] agency
(continued...)
- 71 -

On the record before us, we find that petitioners have

failed to carry their burden of establishing that during each of

the years at issue Crown Capital was Mr. Ackerman’s agent.

Petitioners’ Compensation Argument

As we understand it, petitioners are arguing that during

each of the years at issue Mr. Ackerman received compensation

other than the normal investor’s return for the advisory services

that he provided during each of those years with respect to the

major projects. Consequently, according to petitioners, under

applicable caselaw, during each of the years at issue Mr.

Ackerman was engaged in a trade or business of providing advisory

services within the meaning of section 162(a). The principal

case on which petitioners rely to support that argument is Giblin

v. Commissioner, 227 F.2d 692 (5th Cir. 1955), revg. T.C. Memo.

76
(...continued)
relationship”, Commissioner v. Bollinger, 485 U.S. at 349,
between Crown Capital and Mr. Ackerman: (1) There was a written
agreement that set forth that Crown Capital was an agent of Mr.
Ackerman during any of the years at issue; (2) Crown Capital
functioned for any purpose as an agent with respect to the major
projects that he pursued during those years; and (3) Crown
Capital was held out as an agent of Mr. Ackerman in all dealings
with third parties relating to those projects during those years.
To the contrary, we have found that during the years at issue
Crown Capital, in its own name, entered into various management
service agreements with the respective companies involved in
certain of the projects that Mr. Ackerman pursued. Pursuant to
those agreements, in exchange for certain fees to be paid by
those respective companies to Crown Capital, Crown Capital was to
provide certain services to them.
- 72 -

1954-186.77 According to petitioners, “Mr. Ackerman’s business

was not dissimilar [to that of the taxpayer in Giblin], as he

helped people create and structure transactions.” What petition-

ers fail to understand or choose to ignore is that the fact that

Mr. Ackerman may have “helped people create and structure trans-

actions” in providing advisory services during the years at issue

with respect to the major projects is not determinative of

whether for each of those years he was engaged in a trade or

business of providing those services within the meaning of sec-

tion 162(a).

In Giblin v. Commissioner, supra, the United States Court of

Appeals for the Fifth Circuit (Court of Appeals for the Fifth

Circuit) addressed whether the taxpayer “was regularly engaged in

the business of seeking out business opportunities, promoting,

organizing and financing them, contributing to them substantially

50% of his time and energy and then disposing of them either at a

profit or loss”. The Court of Appeals for the Fifth Circuit held

that the taxpayer was engaged in that business. In so holding,

that Court relied on, inter alia, Foss v. Commissioner, 75 F.2d

77
Petitioners also rely on certain other cases to establish
that during each of the years at issue Mr. Ackerman was engaged
in a trade or business of providing advisory services within the
meaning of sec. 162(a). We have carefully considered each of
those other cases. We find all of them to be materially distin-
guishable from the instant cases and petitioners’ reliance on
them to be misplaced.
- 73 -

326 (1st Cir. 1935), and Sage v. Commissioner, 15 T.C. 299

(1950). Giblin v. Commissioner, supra at 696.

In Whipple v. Commissioner, 373 U.S. 193, 203 n.10 (1963),

which the Supreme Court decided after Giblin, the Supreme Court

expressly disapproved of any statements and holdings in Foss and

Sage that were contrary to its statements and holdings in

Whipple. In Whipple, the Supreme Court addressed whether a

taxpayer who had furnished regular services to several corpora-

tions in which he was an investor was engaged in an independent

trade or business. The Supreme Court held that “Absent substan-

tial additional evidence, furnishing management and other ser-

vices to corporations for a reward not different from that flow-

ing to an investor in those corporations is not a trade or busi-

ness”. Id. at 203 (fn. ref. omitted). In so holding, the Su-

preme Court stated:

Devoting one’s time and energies to the affairs of
a corporation is not of itself, and without more, a
trade or business of the person so engaged. Though
such activities may produce income, profit or gain in
the form of dividends or enhancement in the value of an
investment, this return is distinctive to the process
of investing and is generated by the successful opera-
tion of the corporation’s business as distinguished
from the trade or business of the taxpayer himself.
When the only return is that of an investor, the tax-
payer has not satisfied his burden of demonstrating
that he is engaged in a trade or business since invest-
ing is not a trade or business and the return to the
taxpayer, though substantially the product of his ser-
vices, legally arises not from his own trade or busi-
ness but from that of the corporation. Even if the
taxpayer demonstrates an independent trade or business
of his own, care must be taken to distinguish bad debt
- 74 -

losses arising from his own business and those actually
arising from activities peculiar to an investor con-
cerned with, and participating in, the conduct of the
corporate business.

If full-time service to one corporation does not
alone amount to a trade or business, which it does not,
it is difficult to understand how the same service to
many corporations would suffice. To be sure, the pres-
ence of more than one corporation might lend support to
a finding that the taxpayer was engaged in a regular
course of promoting corporations for a fee or commis-
sion, * * * or for a profit on their sale, see Giblin
v. Commissioner, 227 F.2d 692 * * *, but in such cases
there is compensation other than the normal investor’s
return, income received directly for his own services
rather than indirectly through the corporate enterprise
* * *

Id. at 202-203.

Although, as quoted above, the Supreme Court in Whipple

cited Giblin v. Commissioner, 227 F.2d 692 (5th Cir. 1955), it

cited Giblin only for the narrow proposition that “the presence

of more than one corporation might lend support to a finding that

the taxpayer was engaged in a regular course of promoting corpo-

rations * * * for a profit on their sale”. Whipple v. Commis-

sioner, supra at 202-203. In citing Giblin for that narrow

proposition, the Supreme Court emphasized that in order to con-

clude that a taxpayer is engaged in a trade or business “there

* * * [must be] compensation other than the normal investor’s

return, income received directly for * * * [the taxpayer’s] own

services rather than indirectly through the corporate enter-

prise”. Id. We must read Giblin in a manner that is consistent
- 75 -

with Whipple. We did so in Deely v. Commissioner, 73 T.C. 1081

(1980), a case that petitioners do not cite.

In Deely, we addressed whether a taxpayer who had organized

and financed 26 companies was engaged in the trade or business of

promoting, organizing, financing, and/or dealing in corporations.

We held in Deely that the taxpayer was not engaged in that trade

or business. Id. at 1096. In so holding, we stated:

In order to establish a business separate from
that of his corporations, * * * [the taxpayer] must
show that the compensation he seeks from his activities
is other than the normal investor’s return and that
income received is directly for his services rather
than indirectly through the successful operation of the
corporate enterprise. Whipple v. Commissioner, supra
at 203.

* * * [The taxpayer] contends that he was in the
separate business of promoting, organizing, financing,
and/or dealing in corporations. It seems clear from
Whipple that to qualify such activities as a separate
business they must be conducted for a fee or commission
or with the immediate purpose of selling the corpora-
tions at a profit in the ordinary course of that busi-
ness. * * * There is no evidence in this case that
* * * [the taxpayer] received any fees or commissions
for organizing, financing, or promotional activities;
instead, he usually invested or took an equity interest
in the entities that he organized, promoted, or fi-
nanced. * * *

Id. at 1093.

In reaching our holding in Deely v. Commissioner, supra at

1093, we considered Giblin v. Commissioner, supra. We concluded

in Deely that in order to come within the holding in Giblin a

taxpayer must show that the taxpayer organized the entities in

which the taxpayer invested “with a view to a quick and profit-
- 76 -

able sale after each business had become established, rather than

with a view to long-range investment gains.”78 Id.

In contrast to the taxpayer in Giblin v. Commissioner,

supra, petitioners do not claim, and presented no evidence, let

alone credible evidence, see sec. 7491(a), establishing, that

during each of the years at issue Mr. Ackerman provided advisory

services pertaining to the finances and management of the respec-

tive companies involved in the major projects with the purpose of

selling his respective interests in those companies at a profit

in the ordinary course of his alleged business of providing those

services.79 We find Giblin to be materially distinguishable from

the instant cases and petitioners’ reliance on that case to be

misplaced.

On the record before us, we find that petitioners have

failed to carry their burden of establishing that during each of

the years at issue Mr. Ackerman provided advisory services with

respect to the major projects with the purpose of selling his

78
We observed in Deely v. Commissioner, 73 T.C. 1081, 1093
n.11 (1980), that “it would appear that Giblin v. Commissioner,
227 F.2d 692 (5th Cir. 1955), has been sapped of some of its
vitality by the opinions of the Fifth Circuit in Bodzy v. Commis-
sioner, 321 F.2d 331 (5th Cir. 1963); and United States v. Byck,
325 F.2d 551 (5th Cir. 1963).”
79
Indeed, on the record before us, we find that petitioners
have failed to establish that Mr. Ackerman sold any of his
respective interests in the companies involved in the major
projects in the ordinary course of his alleged business of
providing advisory services.
- 77 -

interests in the respective companies involved in those projects

at a profit in the ordinary course of his alleged business of

providing those services.80 See Whipple v. Commissioner, 373 U.S.

at 202-203; Deely v. Commissioner, supra at 1093; cf. Giblin v.

Commissioner, supra.

We shall address now whether during each of the years at

issue Mr. Ackerman provided advisory services with respect to

each of the major projects in exchange for a fee or a commission

or any other compensation other than the normal investor’s re-

turn. See Whipple v. Commissioner, supra at 202-203; Deely v.

Commissioner, supra at 1093.

With respect to the major project pertaining to Equity

Marketing (Equity Marketing project), petitioners claim that Mr.

Ackerman received a fee in exchange for the advisory services

that he provided with respect to that project.81 To support that

claim, petitioners rely on the testimony of Mr. Ackerman on which

we are unwilling to rely to establish petitioners’ position with

respect to their claimed Schedule C deductions. In this regard,

80
See supra note 79.
81
Petitioners reported no income, let alone income from the
Equity Marketing project, in Schedule C for each of the years at
issue. Moreover, petitioners do not claim, and the record does
not establish, that they reported in any other part of their
joint returns for any of the years at issue the fee that peti-
tioners claim Mr. Ackerman received in exchange for the advisory
services that he provided with respect to the Equity Marketing
project.
- 78 -

Mr. Ackerman testified that he received a fee in exchange for the

advisory services that he provided with respect to the Equity

Marketing project. Our understanding is that the fee to which

Mr. Ackerman referred in his testimony is the commitment fee that

Equity Marketing agreed to pay to Crown Acquisition Partners, or

any of its affiliates, as part of Equity Marketing’s agreement to

sell to Crown Acquisition Partners certain shares of its stock

and certain warrants to purchase certain other shares of its

stock. There is no reliable evidence in the record establishing

that Equity Marketing was required to, and did, pay the commit-

ment fee required in the Equity Marketing securities purchase

agreement in exchange for any advisory services that Mr. Ackerman

provided to Equity Marketing. We have found that that commitment

fee was required to be paid to Crown Acquisition Partners or one

of its affiliates as part of Equity Marketing’s agreement to sell

to Crown Acquisition Partners certain shares of its stock and

certain warrants to purchase certain other shares of its stock

and that it was paid to Crown Capital, one of Crown Acquisition

Partners’ affiliates. That commitment fee was not required to

be, and was not, paid to Mr. Ackerman.82

82
The record does not establish, and petitioners do not even
claim, that they reported in any of their joint returns for the
years at issue the commitment fee required in the Equity Market-
ing securities purchase agreement. See supra note 81.
- 79 -

Petitioners claim not only that Mr. Ackerman received a fee

in exchange for the advisory services that he provided with

respect to the Equity Marketing project, but also that he re-

ceived dividends in exchange for those services. The parties do

not dispute that petitioners received, and reported in their

joint return for each of their taxable years 2000 through 2006,

certain dividend income from Equity Marketing that had flowed

through, inter alia, Somerville. Howeve

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Source: Frix Law Library, https://www.frixlaw.com/law-library/cases/4337541. Public record. Not legal advice.
