# Estate Burton Kanter v. CIR

> Court of Appeals for the Seventh Circuit · July 24, 2003

URL: https://www.frixlaw.com/law-library/cases/2996510

## Case

- **Court:** Court of Appeals for the Seventh Circuit
- **Decided:** July 24, 2003
- **Precedential status:** Published
- **Opinion:** Opinion
- **Judges:** Per Curiam
- **Nature of suit:** tax
- **Cited by:** 0 later opinions in the Frix Law Library

## Citator (automated)

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- Full citator and citing cases: https://www.frixlaw.com/law-library/cases/2996510

## How later opinions describe it (automated extraction)

- observing in dicta that in the criminal context a district court judge’s reversal of a magistrate judge’s credibility findings without the district judge hearing or seeing the witnesses would raise “serious questions”
- finding no presumption of cor- rectness when Commissioner’s assessed deficiency lacks any reasonable foundation in the evidence
- noting that in 1969 Congress removed the Tax Court from the realm of executive agencies and made it an Article I court

## Opinion text

In the
United States Court of Appeals
For the Seventh Circuit
____________

Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220
ESTATE OF BURTON W. KANTER, deceased,
JOSHUA S. KANTER, executor, and NAOMI KANTER,
Petitioners-Appellants,
v.

COMMISSIONER OF INTERNAL REVENUE,
Respondent-Appellee.
____________
Appeals from a Decision of the United States Tax Court
Nos. 712-86, 1350-87, 31301-87, 33557-87,
3456-88, 32103-88, 26251-90.
____________
ARGUED SEPTEMBER 4, 2002—DECIDED JULY 24, 2003
____________

Before FLAUM, Chief Judge, CUDAHY and KANNE, Circuit
Judges.
PER CURIAM. The Estate of Burton Kanter and Naomi
Kanter appeal a decision of the Tax Court. This con-
solidated appeal deals with six out of forty-one separate
issues decided by the Tax Court with respect to alleged
deficiencies of the late Burton W. Kanter, his wife, Naomi
Kanter, and related entities, as well as two additional post-
trial issues. We affirm in part and reverse in part.
2 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

INTRODUCTION
The late Burton W. Kanter,1 and various family entities
associated with him, have been audited by the Inter-
nal Revenue Service virtually, if not literally, every year
since Richard Nixon was President. Kanter was a well-
known and accomplished tax and estate lawyer. He gradu-
ated from the University of Chicago Law School. He had a
very successful law practice beginning in 1956, founding
what would eventually become the law firm of Neal, Gerber
& Eisenberg. Among Kanter’s clients was the Pritzker
family of Hyatt Corporation fame. Kanter was also an
accomplished businessman, with “extensive exposure” to a
“good many public . . . . [and] private companies.” (Tr. at
5278.)2 Kanter wrote extensively on tax-related subjects
(originating a “Shop Talk” column in the Journal of Tax-
ation), and was an expert on the subject of trusts and
estate planning. See, e.g., Burton W. Kanter & Michael J.
Legamaro, The Grantor Trust: Handmaiden to the IRS and
Servant to the Taxpayer, 75 TAXES 706 (1997); Sheldon I.
Banoff & Burton W. Kanter, LLC Announcements: Damage
Control, 80 J. TAX’N 255 (1994); Burton W. Kanter &
Sheldon I. Banoff, Tax Planning for the Elderly, 70 J. TAX’N
191 (1989); Burton W. Kanter, AARP—Asset Accumulation,
Retention and Protection: Prelude to Transmission, 69
TAXES 717 (1991); Burton W. Kanter, Cash in a “B” Reorga-
nization: Effect of Cash Purchases on “Creeping” Reorgani-

1
Burton W. Kanter died on October 31, 2001. His estate was
subsequently substituted as the principal party to this litigation.
In order to avoid semantic contortions, this opinion refers
interchangeably to the current Petitioners collectively, the Estate
of Burton W. Kanter individually and to the late Burton Kanter,
as “Kanter.”
2
“Tr.” refers to the transcript for the Tax Court trial. “App.” will
refer to the appendix to Petitioners’ brief.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 3
01-4321, 01-4322, & 02-1220

zation, 19 TAX L. REV. 441 (1964). In the 1960s and 1970s,
Kanter helped Hollywood finance movies through tax
shelter arrangements, and was involved in the produc-
tion of many major Hollywood films, including “One Flew
Over the Cuckoo’s Nest.” The IRS’s extraordinary atten-
tion to Kanter is understandable given that from 1979 to
1989 Kanter, the highly successful tax attorney, who
hobnobbed with Pritzkers and Hollywood producers and
who participated in countless extremely large and lucrative
business ventures, reported a negative adjusted gross
income each year on his federal tax return and paid no
federal income taxes. (Tr. at 5290-91.)
This consolidated appeal involves Kanter’s petitions for
review of deficiencies assessed during the years from 1978
to 1986, which is itself only a portion of the original con-
solidated case tried by the Tax Court in 1994—a trial that
generated almost 5500 pages of transcript, more than
4600 pages of briefs and thousands of exhibits consuming
hundreds of thousands of pages, and was eventually, five
years later, distilled into a 606 page opinion covering forty-
one separate issues. A thorough description of the entire
factual background to this case can be found in the Tax
Court’s opinion. Investment Research Associates, Ltd. v.
Comm’r, 78 T.C.M. (CCH) 951 (1999) [hereinafter IRA]. The
trial was conducted by Special Trial Judge Couvillion, to
whom the Tax Court had assigned the case under 26 U.S.C.
§ 7443A(b)(4). See also Tax Court Rule 180.3 Under the
Tax Court’s rules, the Special Trial Judge (STJ) then
submitted a report containing findings of fact and opinion
to the Tax Court’s Chief Judge, who then assigned the case
to Tax Court Judge Dawson. See Tax Court Rule 183(b).
Judge Dawson subsequently issued his opinion, which

3
All Rule references are to the Rules of the United States Tax
Court (Tax Court Rules) unless otherwise indicated.
4 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

stated that the Tax Court “agrees with and adopts the
opinion of the Special Trial Judge, which is set forth below.”
IRA, 78 T.C.M. (CCH) at 963. Of the forty-one issues
decided by the Tax Court, six were appealed to this court:4
1. Fraud: The Tax Court determined that Kanter (and
two colleagues) helped individuals obtain business oppor-
tunities in exchange for payments that later were fraud-
ulently diverted through a series of Kanter-controlled
entities in order to disguise the payments’ origins and lower
the tax assessed on the income (by dividing it up and
assigning parts of it to various entities claiming losses).
Kanter concedes that there was an underpayment of taxes
but disputes that the Commissioner was able to prove
by clear and convincing evidence that the underpayment
was due to fraud.
2. Bea Ritch Trusts: Kanter challenges the Tax Court’s
determination that capital gains reported in 1986 by the
Bea Ritch Trusts (BRT) were properly taxable to Kanter
under the grantor trust provisions of the Internal Reve-
nue Code (IRC).
3. Washington Painting: Kanter challenges the Tax
Court’s refusal to allow him to deduct expenses he in-
curred during an aborted sale of a painting.

4
The Tax Court trial consolidated the petitions of Kanter and
two other individuals (Lisle and Ballard) against whom the Com-
missioner assessed deficiencies. Under 26 U.S.C. § 7482(b)(1)(A),
appeals from Tax Court decisions are reviewed by the U.S. Court
of Appeals for the circuit in which the legal residence of the
petitioner lies. Of the three petitioners, only Kanter’s legal
residence lies within the Seventh Circuit. Parallel appeals for the
other petitioners are ongoing in the Fifth and Eleventh Cir-
cuits. During the pendency of this appeal the Eleventh Circuit
issued its opinion. Ballard v. Comm’r, 321 F.3d 1037 (11th Cir.
2003).
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 5
01-4321, 01-4322, & 02-1220

4. 1982 Bank Deposits: Kanter challenges the Tax
Court’s determination of a deficiency for the year 1982
based upon an analysis of his bank deposits. He argues
that the Commissioner failed to meet his burden to prove
a deficiency, that the Tax Court erred in presuming the
Commissioner’s deficiency determination to be correct,
and that in any event the evidence Kanter presented
at trial was sufficient to overcome any presumption of
correctness.
5. Equitable Leasing: Kanter challenges the Tax Court’s
determination that payments from Equitable Leasing
Company to Kanter entities were taxable commissions
and not loans.
6. Cashmere: The Tax Court disregarded a series of
transactions involving (a) the contribution of certain
partnership interests to a shelf corporation (Cashmere)
and (b) the subsequent installment sale of Cashmere’s
stock, the result of which was an immediate recognition of
capital gain to Kanter on the partnership interests. Kanter
argues that the transactions had economic substance
and should not have been disregarded as an attempt to
avoid the payment of federal income tax.
The remaining two issues in this appeal concern events
after the conclusion of the Tax Court’s trial. Beginning in
April 2000, Kanter sought repeatedly to have the orig-
inal report filed by the STJ placed in the record, or in the
alternative made available for this Court’s review in
camera. Kanter alleged that informal conversations with
two Tax Court judges had revealed that the issued opin-
ion had undergone significant alterations from the orig-
inal report filed by STJ Couvillion. The Tax Court denied
all of Kanter’s motions. Kanter appeals the Tax Court’s
refusal to produce the STJ’s original report. The final issue
concerns Kanter’s wife’s (Naomi’s) efforts to seek innocent-
6 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

spouse relief from the deficiencies levied against her hus-
band’s estate.
To make this very complex case easier to understand
we have placed a brief statement of facts relevant to each
issue immediately preceding that issue’s analysis. We be-
gin with the broadest (and least fact dependent) issue:
whether the STJ’s original report should have been made
part of the record on appeal. Then we address the six
transactional issues from the Tax Court’s decision. Finally,
we address Naomi Kanter’s post-trial motions.
The United States Courts of Appeals have exclusive
jurisdiction to review decisions of the United States Tax
Court. 26 U.S.C. § 7482(a)(1); Seggerman Farms, Inc. v.
Comm’r, 308 F.3d 803, 805 (7th Cir. 2002).

I. The STJ’s Report
Kanter’s first argument is that the STJ’s original report
must be made a part of the record on appeal so that this
court can determine whether the appropriate degree of
deference had been paid to it by the Tax Court judge, whose
opinion is before us. Kanter claims that informal conver-
sations between his attorney and other Tax Court judges
revealed that the STJ who presided over the trial of this
case submitted a report that found Kanter credible and
recommended rejection of much of the Commissioner’s
assessed deficiencies, specifically the fraud deficiency.
Kanter argues that the STJ’s report cannot be rejected
by the Tax Court unless clearly erroneous, and that,
without the STJ’s report in the record, there is no way
for this court to determine if proper deference was accorded
it. Moreover, this secret and unaccountable process of
review allegedly violates Kanter’s due process rights.
Kanter, relying on a Supreme Court case examining the
relationship between U.S. district court judges and magis-
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 7
01-4321, 01-4322, & 02-1220

trate judges, argues that this quasi-collaborative process
affords a Tax Court the opportunity to reverse an STJ’s
credibility findings without first hearing or seeing the
witnesses itself—thus offending due process. See Raddatz
v. United States, 447 U.S. 667, 681 n.7 (1980) (observing
in dicta that in the criminal context a district court
judge’s reversal of a magistrate judge’s credibility findings
without the district judge hearing or seeing the witnesses
would raise “serious questions”). Kanter argues that in
addition, our review of the Tax Court’s decision is uncon-
stitutionally impaired by the omission of the STJ’s report
from the record. Kanter’s challenge of the Tax Court’s
refusal to include the “original” STJ report presents
questions of law that we review de novo. Pittman v.
Comm’r, 100 F.3d 1308, 1312 (7th Cir. 1996).
Of course, Kanter’s arguments are immaterial if the
Tax Court’s final opinion is the STJ’s report. See Ballard,
321 F.3d at 1042-43. The Tax Court’s final opinion clearly
states that it “agrees with and adopts the opinion of the
Special Trial Judge.” IRA, 78 T.C.M. (CCH) at 963. The
Chief Judge of the Tax Court, Judge Dawson, and Spe-
cial Trial Judge Couvillion himself all signed that final
opinion, and we take their statement at face value. There-
fore, notwithstanding Kanter’s attorney’s declaration, we
accept as true the Tax Court’s statement that the under-
lying report adopted by the Tax Court was in fact Special
Trial Judge Couvillion’s. See Ballard, 321 F.3d at 1042-43.
This renders moot all of Kanter’s arguments.
But even if, as the dissent suggests, the phrase “agrees
with and adopts” masks what is in fact a quasi-collabora-
tive judicial deliberation in which an STJ’s initial findings
are malleable, neither the Tax Court’s own rules of pro-
cedure, the Federal Rules of Appellate Procedure, nor
Congress’ scheme for appeals from Tax Court decisions
would require the Commissioner to include the STJ’s
8 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

preliminary report as part of the appellate record. Further-
more, this purportedly quasi-collaborative process would
not offend our notions of fundamental fairness, nor would
due process require the inclusion of the report in the
appellate record to preserve the fairness of our review.
First, it is clear that the Tax Court’s own rules do not
require the report to be disclosed to the parties or made
part of the appellate record. To the contrary, its rules
specifically preclude the report’s disclosure. That the Tax
Court has the power to prescribe its own rules of procedure
is undisputed. See 26 U.S.C. § 7453; Stone v. Comm’r, 865
F.2d 342, 347 (D.C. Cir. 1989) (“The Tax Court is of
course free to make its own rules determining the relation
between it and its Special Trial Judges.”). Having exercised
that rulemaking authority, the Tax Court no longer re-
quires an STJ’s report to be made available to the parties
and, by extension, no longer allows those parties to file
objections to it. Compare Tax Court Rule 182(b), (c), 60 T.C.
1149 (1973) (providing for service of the STJ’s report on
each party and allowing each party to file objections to the
report’s findings), with Tax Court Rule 183, 81 T.C. 1070
(adopted 1983) (noting that “[t]he prior provisions for
service of the [STJ’s] report on each party and for the fil-
ing of exceptions to that report have been deleted”).
Neither do the Tax Court procedures prescribe any
particular level of deference due the STJ’s report. Under
the current rule, the Tax Court maintains sole authority
to decide cases assigned to an STJ. Tax Court Rule 183(c)
(“The Judge to whom or the Division to which the case
is assigned may adopt the [STJ’s report] or may modify it
or may reject it in whole or in part . . . .”); see also Freytag
v. Comm’r, 501 U.S. 868, 875 n.3 (1991) (“[A] special trial
judge has no authority to decide a case assigned under
[§ 7443(b)(4)].”). The Tax Court thus acts as the original
finder of fact. Conversely, the STJ’s inability to decide
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 9
01-4321, 01-4322, & 02-1220

cases limits the amount of deference that the Tax Court, as
the original factfinder, must pay to those preliminary
findings. Although the Rule requires that “due regard” be
given to the STJ’s opportunity to evaluate the credibility
of witnesses and that those findings be presumed correct,
see Tax Court Rule 183(c), to impose the further require-
ment that the Tax Court review an STJ’s findings for
clear error, as Kanter urges, would all but abdicate the
Tax Court’s original decisionmaking authority. Instead,
we believe Rule 183’s due-regard language merely in-
structs the Tax Court to be cognizant that the STJ had
the opportunity to evaluate the credibility of witnesses,
and allows the Tax Court to overcome the presumption of
correctness it prescribes should it find that the evidence
suggests those findings were incorrect. Consequently,
secreting the report does not offend any rule-mandated
check on the Tax Court’s power to decide cases assigned
to an STJ.
Second, Congress has by statute precluded direct appel-
late review of STJ reports. We lack jurisdiction to re-
view anything but “decisions of the Tax Court.” 26 U.S.C.
§ 7482(a)(1). We have repeatedly held that the use of the
term “decisions” in § 7482 means that the appellate
courts can review only (i) dismissals (e.g., for lack of juris-
diction) or (ii) formal determinations of deficiency (or lack
thereof). See, e.g., Krieder v. Comm’r, 762 F.2d 580, 584 (7th
Cir. 1985). In other words, a “decision” of the Tax Court
is the final formal ruling of the Tax Court; a preliminary
“report” is not a decision. See 26 U.S.C. § 7459(a) (“A re-
port upon any proceeding instituted before the Tax Court
and a decision thereon shall be made as quickly as prac-
ticable. The decision shall be made by a judge in accord-
ance with the report of the Tax Court, and such decision
so made shall, when entered, be the decision of the Tax
Court.” (emphasis added)). An STJ report, therefore, is
10 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

not reviewable, see Estate of Smith v. Comm’r, 638 F.2d 665,
670 (3d Cir. 1981), which lends credence to the Commis-
sioner’s argument that Congress intended STJ reports to
be treated as preliminary findings comprising part of the
Tax Court’s internal deliberative process.
Third, the Federal Rules of Appellate Procedure do not
require that STJ reports be made part of the statutorily
required record on appeal of a “decision” of the Tax Court.
Federal Rule of Appellate Procedure 14 excepts appeals
of Tax Court decisions from certain rules of appellate
procedure.5 Among those rules not applicable to Tax
Court review is Rule 16, which provides that the record on
review of an administrative order shall include “any
findings or report on which [the order] is based.” FED. R.
APP. P. 16(a)(2). Unlike other administrative actions, the
Federal Rules of Appellate Procedure thus do not require
that Tax Court decisions be reviewed in light of the pre-
liminary findings upon which the decision was based.
Instead, Rule 13 notes that Rule 10 governs the contents
of a Tax Court appellate record, and that rule does not
require the record to include any preliminary findings or
reports. FED. R. APP. P. 13 & 10(a)6

5
Federal Rule of Appellate Procedure 14 states that “[a]ll
provisions of these rules, except Rule 4-9, 15-20, and 22-23, apply
to review of a Tax Court decision.” FED. R. APP. P. 14.
6
Federal Rule of Appellate Procedure 13 provides in relevant
part:
(d) The Record on Appeal; Forwarding; Filing.
(1) An appeal from the Tax Court is governed by the
parts of Rules 10, 11, and 12 regarding the record on
appeal from a district court, the time and manner of
forwarding and filing, and the docketing in the court of
appeals. References in those rules and in Rule 3 to the
(continued...)
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 11
01-4321, 01-4322, & 02-1220

With these considerations in mind, we find that the
relationship between the preliminary reports of STJs and
the final, reviewable “decisions” of the Tax Court bears
striking resemblance to the relationship between reports
of “divisions” of the Tax Court and final decisions of the
Tax Court itself. A “division” is a subset of the Tax Court
(often a single judge) that is designated to hear a single
case and is empowered to make determinations with re-
spect to disputes before the Tax Court. 26 U.S.C. §§ 7444(c),
7460(a). Under § 7460, the division’s decision generally
becomes the decision of the Tax Court, but the Tax Court
retains the power to review the division’s decision and
render its own. Those preliminary recommendations of
the division which do not become part of the final decision
of the Tax Court also do not become part of the record for
any additional future review. Id. § 7460(b) (“The report
of a division shall not be a part of the record in any case in
which the chief judge directs that such report shall be
reviewed by the Tax Court.”).

6
(...continued)
district court and district clerk are to be read as refer-
ring to the Tax Court and its clerk.
FED. R. APP. P. 13(d)(1). And Federal Rule of Appellate Procedure
10 provides in relevant part:
(a) Composition of the Record on Appeal. The following items
constitute the record on appeal:
(1) the original papers and exhibits filed in the district
court;
(2) the transcript of proceedings, if any; and
(3) a certified copy of the docket entries prepared by the
district clerk.
FED. R. APP. P. 10(a).
12 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

Thus, the two circuits to have interpreted § 7460 have
ruled that a division’s preliminary report is not part of the
appellate record and not available for review by a federal
appeals court once the Tax Court has undertaken an
internal review. See Estate of Varian v. Comm’r, 396 F.2d
753, 755 n.2 (9th Cir. 1968); Heim v. Comm’r, 251 F.2d 44,
48 (8th Cir. 1958). The Ninth Circuit noted a congres-
sional intent in § 7460 to preclude a two-tier appellate
relationship between the division and the full court
and determined that such a mandate did not offend the
court’s notions of fundamental fairness. Varian, 396 F.2d
at 755 n.2.
Given the similarities between these two relationships,
we are led to the same conclusion that the Ninth Circuit
reached in Varian: there is no two-tier appellate rela-
tionship between STJs and the Tax Court. Instead, STJ
reports are treated by the Tax Court as preliminary
findings only and, in accordance with applicable rules
and statutes, are not required to be made part of the rec-
ord on appeal.
The dissent takes issue with this comparison, noting
that divisions are comprised of one or more Tax Court
judges, who are all presidentially appointed and serve a
fifteen-year, statutorily mandated term of office from
which they can be removed only for “inefficiency, neglect
of duty, or malfeasance in office but for no other cause.” 26
U.S.C. § 7443(f). STJs, however, serve at the discretion of
the Chief Judge and have no statutorily mandated term of
office. Id. § 7443A. If Tax Court Rule 183 provides for a
quasi-collaborative process, the dissent fears this dis-
tinction between the participants impairs the judicial
independence of the STJ. As a result, the dissent ques-
tions whether an STJ can participate meaningfully in
this internal deliberative process. See post at 87.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 13
01-4321, 01-4322, & 02-1220

We respectfully disagree. We are hesitant to suggest that
members of the Tax Court would either expressly coerce
or by nature of their office exert undue influence over an
STJ. Nor will we discredit an STJ’s express statement that
the final Tax Court opinion “agrees with” his own based
solely on this observed distinction.
This procedure, while admittedly unusual vis a vis typi-
cal judicial procedure, does not offend our notions of
fundamental fairness. See Varian, 396 F.2d at 755. In this
respect, we agree with the dissent’s conclusion that
due process neither requires the Tax Court to be con-
strained by a formal degree of deference to the STJ nor
requires the Tax Court to rehear witnesses whether or not
it ultimately reverses the STJ’s findings. See post at 89-94
(discussing United States v. Raddatz, 447 U.S. 667 (1980)
and Universal Camera Corp. v. NLRB, 340 U.S. 474, 492-94
(1951)). Although dictum in the Supreme Court’s decision
in Raddatz suggests that “serious questions” may arise
from a district court’s reversal of a magistrate judge’s
credibility findings without the opportunity to personally
see or hear the witnesses, see 447 U.S. at 681 n.7, that
observation was made within the context of a criminal
appeal. In a civil tax proceeding, a party’s interests are
more akin to those at stake in a typical administra-
tive adjudication, and we agree with the dissent that
the risk of erroneous deprivation in a civil proceeding is
neither “as high, nor the costs as great, as would be the
case in a criminal milieu.” See post at 93 (discussing Tax
Court Rule 183 within the procedural-due-process frame-
work established by Matthews v. Eldridge, 424 U.S. 319,
333 (1976)). Moreover, we agree that the “only fully re-
sponsive remedy” to Kanter’s complaint would prove
unworkable, as it would require the enormous burden
and prohibitive cost of rehearing witnesses, which would
ultimately prove to add little value given the continued
14 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

input that the STJ retains under Tax Court Rule 183’s
purportedly quasi-collaborative process. See post at 93-94.
But the recognition that little value would be added to
the process given the STJ’s continued involvement—
signified by his adoption of the statement that the final
Tax Court opinion reflects his own opinion—is ulti-
mately why we take issue with the dissent’s conclusion
that our review of the Tax Court’s opinion is unconstitu-
tionally impaired by this procedure. The conclusion rests
on the premise that STJs do not enjoy an equal voice in
this purportedly quasi-collaborative process. See post at
100-02. As discussed above, we reject this premise. In as
much as the final Tax Court opinion purports to agree with
and adopt the opinion of the STJ, we therefore believe that
the final opinion reflects the true legal opinions and
findings of the STJ. Any differing preliminary recommen-
dations—if they ever existed—would no longer be constitu-
tionally relevant because the STJ has abandoned them.
Should he feel otherwise, we would expect him—or the Tax
Court—to say so.
As the Eleventh Circuit recently noted, “there is noth-
ing unusual about judges conferring with one another
about cases assigned to them.” Ballard, 321 F.3d at 1043.
If Tax Court Rule 183 in fact provides the opportunity for
STJs and Tax Court judges to conference regarding the
STJ’s preliminary findings, then we have every reason to
believe that Tax Court judges would duly regard the in-
put of the STJ and that he, in turn, would participate
meaningfully in the exchange. Like the Ninth and the
Eleventh Circuits, we too are loath to interfere with an-
other court’s deliberative process. See id.
In any event, the issue is academic since the Tax Court’s
opinion in this case purports to “agree with and adopt”
Special Trial Judge Couvillion’s opinion. We will take the
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 15
01-4321, 01-4322, & 02-1220

Tax Court at its word and, thus, move on to a discussion on
the merits of Kanter’s appeal.

II. Fraud
A. Facts
The bulk of the Tax Court’s opinion involves its deter-
mination that certain income tax underpayments were
made with fraudulent intent. The facts surrounding the
fraud issue are the most complex of all and will be de-
scribed as succinctly as possible.
The Tax Court’s decision tells a story of Kanter and
two business associates—Robert Lisle and Claude Ballard.
Lisle and Ballard worked in real estate, principally as
managers in the real estate division of Prudential Insur-
ance Company, where they had significant authority and
influence over the conduct of Prudential’s business. Kanter,
Lisle, and Ballard concocted a plan whereby they would
use Lisle and Ballard’s positions along with Kanter’s legal
skills to collect and hide payments from people who
wanted to do real estate business with Prudential.7

7
As the Tax Court opinion notes, there were additional sets
of transactions that involved only Lisle and Kanter during
Lisle’s post-Prudential career at Traveler’s Insurance Company
as well as transactions involving Kanter alone. IRA, 78 T.C.M.
(CCH) at 970-71. These transactions followed the same pattern
detailed here where Kanter used his influence to secure busi-
ness opportunities for individuals in return for compensation
that was then diverted through a series of entities in order to
disguise the origin of the funds and avoid income tax liability. For
the sake of simplicity we will refer only to the transactions
involving Prudential and the Five as representative of all of the
transactions detailed by the Tax Court.
16 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

The Tax Court focused on five individuals (referred to
collectively as the Five) who paid Kanter, Lisle, and Bal-
lard for their influence.8 For the Five, Lisle and Ballard
would help secure business opportunities with Prudential,
and in return the Five made payments, including cash
and partnership interests, to Kanter.
It was at this point that the IRS became interested.
According to the Commissioner these payments were
diverted (the Commissioner and Tax Court use the more
highly charged word “laundered”) to entities created
by Kanter or someone acting at Kanter’s direction. The
dominant method was to divert payments to a Kanter-
controlled corporation called Investment Research Associ-
ates, Ltd (IRA).9
The payments to IRA were deposited in the accounts
IRA kept with another Kanter-controlled entity called the
Administration Company. The Administration Co. was
exactly what its name indicates: a company that admin-
istered the records and funds of its clients. It main-
tained books and records for its clients, and often prepared
client tax returns. Additionally, it administered client
funds, collecting receivables and paying bills. Money for
clients was kept in pooled bank accounts listed under

8
The Five were J.D. Weaver, Bruce Frey, William Schaffel,
Kenneth Schnitzer, and John Eulich. The details of the transac-
tions involving the Five are in the Tax Court opinion at 78 T.C.M.
(CCH) at 976-1019.
9
IRA was originally incorporated in 1974 in Delaware as Cedilla
Co. It was intended as a vehicle for making investments. Cedilla
changed its name to Investment Research Associates in 1979.
IRA owned as relevant subsidiaries, at various times, Carlco, TMT
and BWK, Inc. IRA conducted no business and had no em-
ployees other than bookkeepers and paid virtually no amount
in salaries.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 17
01-4321, 01-4322, & 02-1220

Administration Co.’s name. Two of these accounts were
called the Special E account and the TACI Special Account.
Client funds were pooled in order to get the higher rate
of return on aggregated funds and to avoid a multiplicity
of account maintenance charges on many, smaller client
bank accounts kept in the clients’ individual names.
Administration Co. itself (and not the bank where the
accounts were kept) tracked individual client balances
within the pooled accounts on its internal records for
each client. IRA and many of its subsidiaries were clients
of Administration Co.10 In fact, it does not appear that
Administration Co. had any significant clients not di-
rectly associated with (or controlled by) Kanter.
The payments by the Five to IRA that were deposited
in the accounts of the Administration Co. were com-
mingled with other non-Five-related funds of IRA as well
as the funds of other Administration Co. clients. This
commingling and the inadequate record keeping of Admin-
istration Co. made it difficult to track or account for the
payments from the Five.
It was IRA—and not Kanter, Lisle, or Ballard—that
reported the income from the Five’s payments on its tax
return (where it was off-set by aggregated losses). Sub-
sequently, IRA distributed the income into subsidiary
“sham” corporations, BWK, Carlco, and TMT, controlled
by Kanter, Lisle, and Ballard, respectively, in a 10/45/45
ratio, respectively, that represented the division of
the payments allegedly agreed to by Kanter, Lisle, and

10
In 1988, the Administration Co. filed for bankruptcy. Concur-
rently, a company called Principal Services was organized, and
took over many of Administration Co.’s clients, operating with
the same purposes and in the same way as had Administration
Co.
18 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

Ballard.11 These sham corporations were used, in effect, as
the personal bank accounts of Kanter, Lisle, and Ballard,
and these men could withdraw or use the funds con-
tained in them at their leisure.12 The funds withdrawn
were never repaid and were eventually written off as bad
debts. Alternatively, the controlled corporations’ funds
were used to fund the personal expenditures of Kanter,
Lisle, and Ballard, as well as their families.
Kanter, on the other hand, argues that the payments
to the corporations were merely investments by the enti-
ties, “ceded” to them by Kanter. The underlying scheme
of securing business opportunities for the Five interested
individuals in return for payments to Kanter (through
Kanter entities) is disputed in its entirety by Kanter.
The Commissioner argued, and the Tax Court agreed,
that this income was properly taxable to the individuals,
and a deficiency was assessed. The Tax Court held that
the diversion of these funds from the individuals to the
sham corporations was undertaken with the fraudulent
intent to evade the payment of taxes. According to the
Tax Court, this arrangement not only disguised income

11
Carlco, TMT, and BWK were “shelf ” corporations formed by
Kanter in 1982. In 1983, they became active, and IRA acquired
100% of the common stock of each. In 1984, each corporation
issued shares of preferred stock. Carlco issued its preferred shares
to the Christie Trust, a trust established by Kanter for the benefit
of Lisle’s family. TMT’s preferred shares were issued to the
Orient Trust, established by Kanter for the benefit of Ballard’s
family. BWK’s preferred shares were issued to the BK Children’s
Trust, established for the benefit of Kanter’s family. As part of
the scheme, Lisle controlled Carlco’s investment decisions, Bal-
lard controlled TMT’s and Kanter controlled BWK’s.
12
The actions summarized in these few sentences took place over
many years.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 19
01-4321, 01-4322, & 02-1220

earned by the individuals, but also hid their activities
from Prudential.
In the Tax Court, Kanter presented an impressive list
of witnesses associated with Kanter, Lisle, Ballard, the
Five, and the various relevant entities—all of whom
expressly denied that the Five paid “kickbacks” to Kanter
for steering business the Five’s way. But the Tax Court
found that these witnesses had testified that the Five had,
in fact, entered into payment arrangements with Kanter,
Lisle, and Ballard in exchange for their influence in
obtaining business. IRA, 78 T.C.M. (CCH) at 1065. This
testimony established that Kanter had not reported in-
come on which he was taxable and had therefore under-
paid his federal-income-tax obligations. The Tax Court
found that these underpayments were undertaken with
intent to evade taxes based on, inter alia, the following
factors: the lack of credibility of Kanter’s testimony;
Kanter’s legal education and experience indicating an
awareness of his obligation to report income accurately
and pay taxes; Kanter’s substantial underreporting of
income for many years; Kanter’s creation of a complex
laundering network of sham corporations and other enti-
ties that made it difficult to trace the flow of funds;
Kanter’s lack of cooperation with the IRS—namely, the
withholding of documents and the destruction of docu-
ments subject to summonses; Kanter’s commingling of
“kickback” monies with other monies in the Administration
Co.’s accounts; Kanter’s movement of monies through
conduits that had no legitimate business purpose show-
ing an intent to disguise sources of funds; Kanter’s re-
porting of his personal income on the tax returns of IRA
in order to create the appearance that income was earned
by IRA; and Kanter’s use of phony loans to disguise dis-
tributions to himself, later written off as bad debts. IRA, 78
T.C.M. (CCH) at 1083-85.
20 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

B. Analysis
A finding of fraud by the Tax Court is a factual finding
that we review for clear error. Toushin v. Comm’r, 223 F.3d
642, 647 (7th Cir. 2000). As with all findings of fact of
the Tax Court, we must view the evidence in the light
most favorable to the Tax Court’s findings and reverse
only if we are left with the definite and firm conviction
that a mistake has been made. Pittman, 100 F.3d at 1312-
13.
To establish fraud, the Commissioner must prove by
clear and convincing evidence that Kanter’s underpayment
of taxes was done with intent to evade taxes that he
knew or believed were owed. Toushin, 223 F.3d at 647;
Pittman, 100 F.3d at 1319. Fraud may be proven through
circumstantial evidence. Pittman, 100 F.3d at 1319. There
are a variety of commonly recognized indicia of fraud, “such
as keeping a double set of books, making false entries
or alterations, [using] false invoices or documents, [destroy-
ing] books or records, [concealing] assets or covering up
sources of income, handling . . . one’s affairs to avoid
making the records usual in transactions of the kind, and
[undertaking] any conduct, the likely effect of which
would be to mislead or to conceal.” Spies v. United States,
317 U.S. 492, 499 (1943). Additionally, fraud can be shown
by significant and repeated understatement of income,
Pittman, 100 F.3d at 1320, by a lack of cooperation with
investigating agents, Korecky v. Comm’r, 781 F.2d 1566,
1568-69 (11th Cir. 1986); Zell v. Comm’r, 763 F.2d 1139,
1146 (10th Cir. 1985), by destruction of records, Powell v.
Granquist, 252 F.2d 56, 59 (9th Cir. 1958), or by consider-
ing the legal experience and education of the taxpayer,
Plunkett v. Comm’r, 465 F.2d 299, 303 (7th Cir. 1972).
Kanter’s principal argument is based on the representa-
tion he makes above concerning the STJ’s report: Kanter
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 21
01-4321, 01-4322, & 02-1220

and his witnesses were found credible, and his story was
believed by the STJ. Therefore, there can be no finding
of intent to defraud. It was, Kanter alleges, only the
rejection of the STJ’s findings by the Tax Court judge
that led to the finding that Kanter was not credible and
that the underpayment of taxes was accomplished with
fraudulent intent. As discussed above, we refuse to credit
Kanter’s allegations in light of the Tax Court’s statement
that it “agrees with and adopts” the opinion of the STJ.
Therefore, Kanter’s principal argument is without merit.
The Tax Court found that Kanter’s testimony was not
credible and also found significant circumstantial indicia
of fraud. Kanter’s arguments now do not demonstrate
that this is clearly erroneous.
Kanter’s remaining arguments are also meritless. He
argues that it is a common estate planning technique to
cede personal investments to family trusts and corpora-
tions. But he does nothing to undermine the consid-
erable evidence cited by the Tax Court that demonstrates
that the Five paid for Kanter, Lisle, and Ballard’s help
in securing business opportunities, and that those pay-
ments went through IRA to Carlco, TMT, and BWK for
division of the proceeds in a 10/45/45 split. And inas-
much as this argument seeks to show a lack of fraudulent
intent by attacking the existence of a deficiency, this
argument was expressly waived by Kanter.
Additionally, Kanter argues that fraud was raised by
the respondent late in the process by the Commis-
sioner’s amendment to his Answer, that none of the Com-
missioner’s notices of deficiency indicated fraud and that
IRS agents’ reports had found no intent to defraud. While
the Tax Court might have found this persuasive when, as
the trier of fact, it considered the issue of fraud, this
argument is unpersuasive at this stage. Kanter does not
argue that the Commissioner’s amendment was improp-
22 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

erly allowed or otherwise defective. Nor is the Commis-
sioner’s delayed amendment particularly probative of
the sufficiency of the fraud evidence, given the diffi-
culties facing the Commissioner in unraveling the rele-
vant transactions during the time leading up to (and
during) the trial.
Finally, Kanter’s attacks on the circumstantial indicia
of fraud are little more than efforts to recharacterize the
evidence in a manner favorable to Kanter’s version of
events. But a review of the record in the light most fa-
vorable to the Tax Court’s findings makes clear that it
was not clear error to find significant indicia of fraud.
To review just a few of the relevant indicia: first and
foremost, even Kanter concedes that he significantly
underreported his income from the transactions with
the Five over many years. (Pet. Br. at 33.)
Second, the money earned by Kanter through the transac-
tions with the Five was diverted to IRA and commingled
with other monies, where the funds were reported as
income earned by IRA, before ultimately becoming avail-
able to Kanter personally—a complicated money trail
that made it difficult to trace the flow of the funds and
gave the appearance that the money had been earned by
IRA.
Third, there was evidence that Kanter and those acting
at his behest did not cooperate with investigating agents
and even destroyed records that the IRS had requested
formally through its summons power. See 26 U.S.C. § 7602.
James Lunk, an IRS Case Manager, was asked during
his testimony at trial what records Kanter and his repre-
sentatives had provided voluntarily, to which he re-
sponded, “Generally they were records that really wouldn’t
do us a lot of good in the examination in terms of really
getting at the type of information we needed to examine
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 23
01-4321, 01-4322, & 02-1220

the transactions that we were most interested in.” (Tr. at
1055-56.) IRS Agent Paul Dion testified similarly:
I have some very direct recollection[s] of the meeting,
because it was the first time I met Mr. Kanter. And at
the very beginning of the meeting, we discussed some—
had a very nice conversation relating to very general
type[s] of topics. I remember art was one of them, and
a few other generalities. And as soon as we started
discussing the required documentation, it was almost
as if a different person appeared. And that person
became, I guess, very demonstrative in terms of not
wanting to provide us with the information that we
asked for; basically saying that he was going to frame
the issue and not us.
(Tr. at 831-32.) The Commissioner had to seek the as-
sistance of the district court in order to enforce sum-
monses against Kanter seeking documents relevant to
the present case. The district court, in two separate rul-
ings, indicated that Kanter had not cooperated and that
documents had been destroyed even after the IRS sum-
monses for those documents had been issued.13 The court
stated that
[Solomon] Weisgal testified that since [receiving a
summons to compel production of documents], some of

13
Kanter’s argument that the documents were destroyed accord-
ing to a standard document retention policy is unpersuasive. The
existence of a document retention policy, which appears to have
been enforced inconsistently, cannot justify the destruction of
documents that were already subject to an IRS summons.
Further, we agree with the Tax Court and believe that it is
clear from the record that Linda Gallenberger (Kanter’s ac-
countant and Administration Co. employee) and Solomon Weisgal
(Kanter’s associate and trustee/officer for various Kanter entities)
acted at the direction of Kanter.
24 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

the BK documents, including summoned documents
relating to the Kanters, had been turned over to the
Administration Company and that some have been
discarded as part of a three-year record retention and
discard policy. . . . [Linda] Gallenberger testified that
she disposed of some documents [related to Kanter]
after receipt of the IRS summons.
United States v. Administration Co., 74 A.F.T.R.2d 94-5252,
1994 WL 240518, at *2 (N.D. Ill. May 31, 1994). The dis-
trict court went on to note that
The facts are that the Kanters first promised to pro-
duce the documents sought from [entities involved
in the present case] and then, in early February 1994,
notified government counsel that the Entities were
third-parties over whom they had no control. The
eleventh-hour change of position by the Kanters is
indicative of bad faith on the part of the Kanters.
Id. at *3. Less than a month later, the same judge held
Gallenberger in contempt for a continuing failure to com-
ply fully with IRS summonses. United States v. Admin-
istration Co., 74 A.F.T.R.2d 94-5256, 1994 WL 285064, at *2
(N.D. Ill. June 23, 1994) (“Gallenberger misconceives her
duty to use all reasonable efforts to comply with the
summonses. A half-hearted request and cursory further
search are insufficient.”) (internal quotations and cita-
tions omitted).
These and the other indicia cited by the Tax Court, when
considered in a light favorable to the Tax Court’s find-
ings, paint a clear and convincing picture of an intent by
Kanter to evade the payment of taxes he knew or be-
lieved that he owed. It was not clearly erroneous for the
Tax Court to find that Kanter’s underpayment of taxes
involved fraud.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 25
01-4321, 01-4322, & 02-1220

III. Bea Ritch Trusts
A. Facts
The Bea Ritch Trusts (BRT) are a group of twenty-five
trusts established in 1969 under one trust document. The
trust document named Beatrice Ritch, Kanter’s mother,
as the grantor of BRT, Kanter’s friend and business as-
sociate Solomon Weisgal as the trustee and the members
of Kanter’s family as the beneficiaries. According to the
trust document, Beatrice Ritch funded each of the sep-
arate BRT trusts with a $100 check. No evidence (be-
yond the trust document itself) was presented to sub-
stantiate that this actually happened. Kanter himself
was originally named as a beneficiary of twenty-four of
the twenty-five trusts and he alone was granted a power
of appointment over the beneficial interest of BRT. Kanter
allegedly renounced his interest in BRT in 1971, 1977, and
1978, thereby purportedly eliminating his power of ap-
pointment over BRT. At sometime during or before 1987,
however, sixty new beneficiaries were added to BRT.
Before 1987, Kanter borrowed money from BRT, and as
of January 1, 1987, Kanter still owed the trust $287,030.
This debt does not appear to have been secured, nor is
there any indication in the record that a reasonable inter-
est rate (if any) was charged on the loans.
In the early 1970s Kanter participated in business
ventures in Long Island, New York, involving the then
nascent cable television industry. He and other members
of his law firm helped an entity that eventually became
Cablevision Co. raise funds, secure financing and find
investors for its cable business. In return, Kanter (along
with others) was to receive interests in partnerships that
26 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

themselves owned interests in Cablevision.14 Kanter
arranged to have BRT receive the Cablevision partnership
interests to which he was entitled—in essence he con-
tributed the Cablevision partnership interests to BRT. The
Tax Court found that the contribution of Kanter’s Cable-
vision partnership interests (along with other income
and assets) to BRT was the principal source of funding
for BRT. Kanter, therefore, was the true grantor of BRT.
IRA, 78 T.C.M. (CCH) at 1098-99.
In 1987, BRT reported capital gains of $2,033,368 for the
fiscal year ending September 30, 1987, from the sale of
the Cablevision partnership interests owned by BRT.15
Because Kanter was the true grantor of BRT and because
he had a power of appointment to name beneficiaries of
BRT, the Commissioner assessed a deficiency for the
year 1987 against Kanter with respect to BRT’s income
from the Cablevision sale. At trial, the evidence made
clear that the income at issue had been earned during the
calender year 1986, and the Commissioner sought to
amend his pleadings and reallocate the BRT deficiency
from 1987 to 1986. The Tax Court allowed the amend-
ment, and denied Kanter’s request to shift the burden of

14
We speak in generalities in order to avoid further confusing
the situation by expanding the alphabet soup of partnership and
trust abbreviations, whose exact identities are not necessary to
explain the factual background of this issue. The Tax Court’s
opinion fully identifies all the relevant entities. See IRA, 78
T.C.M. (CCH) at 1093-1100. We will simply refer to the partner-
ship interests transferred to IRA for Kanter’s services to
Cablevision as the Cablevision partnership interests.
15
The partnerships in which BRT was a partner sold their
respective interests in Cablevision itself, triggering a capital
gain to the partnerships that then flowed-through to BRT. See
IRA, 78 T.C.M. (CCH) at 1093.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 27
01-4321, 01-4322, & 02-1220

proof to the Commissioner for having raised a “new matter.”
See Tax Court Rule 142(a)(1).
The Tax Court found that Kanter had failed to prove
that he did not fund BRT and, despite his three renuncia-
tions of any beneficial interest in BRT, that he had not
appointed the 60 new beneficiaries. As a result, the Tax
Court held Kanter liable for tax on BRT’s income for 1986
and 1987 under the IRC’s grantor trust provisions. 26
U.S.C. §§ 671, 674. The Tax Court also found that, in the
alternative, Kanter’s borrowing of trust funds made him
taxable on BRT’s income. See 26 U.S.C. § 675(3).

B. Analysis
1. Was the allowance of the amendment proper?
Kanter’s first argument concerns the Tax Court’s al-
lowance of an amendment of the pleadings to conform to
the proof that the alleged deficiency relating to BRT ap-
plied to 1986 rather than to 1987. Kanter argues that it
was error to allow this amendment at all, and that, once
allowed, the Tax Court further erred by not treating this
as a “new matter” under Tax Court Rule 142(a), which
would have shifted the burden of proof on the issue to
the Commissioner.
The decision to allow or deny an amendment of the
pleadings under Tax Court Rule 41 is reviewed for abuse
of discretion. See Estate of Ashman v. Comm’r, 231 F.3d
541, 542 n.2 (9th Cir. 2000); LeFever v. Comm’r, 100 F.3d
778, 786 (10th Cir. 1996); Braude v. Comm’r, 808 F.2d 1037,
1039 (4th Cir. 1986). It was not an abuse of discretion
for the Tax Court to allow the amendment of the Com-
missioner’s pleadings to reallocate the BRT deficiency
to 1986. Kanter was on notice as to the specific partner-
ship income of BRT that was the subject of the assessed
28 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

deficiency. (Tr. at 4483-86.) There was no prejudice to
Kanter in the adjustment of the date, and he had a fair
opportunity to defend with respect to the amended claim.
In fact, it was Kanter, and not the government, who elic-
ited the testimony (from Kanter’s accountant, Gallen-
berger) that revealed the timing error and prompted the
government’s request for amendment.16 The govern-
ment apparently did not realize its error until Kanter
pointed it out at trial. Further, Kanter points to no ad-
ditional evidence that he was prevented from introducing
by virtue of the late amendment. The amendment of the
pleadings to conform to the evidence was proper.

2. Should the amendment have shifted the burden
of proof?
Kanter argues next that the amendment to the plead-
ings was a new matter that shifted the burden of proof
on this issue to the Commissioner. See Tax Court Rule
142(a)(1) (“The burden of proof shall be upon the petitioner,
except . . . that, in respect of any new matter, . . . it shall
be upon the respondent.”). The distribution of burdens is
a question of law that we review de novo. This argument

16
A fair reading of the trial transcript is that Kanter’s strategy
regarding the BRT income was from the beginning to demonstrate
that the income in question had been earned in 1986, not 1987,
and to try to shift the burden of proof to the Commissioner
in precisely the manner argued here. (Tr. at 4455-4501.) With
Kanter’s clear advance knowledge of the calender mistake and
his apparent strategic decision regarding that mistake, we find
it hard to believe Kanter when he says this “was not an issue
that Kanter was prepared to defend at trial”—except inasmuch
as this statement may reflect Kanter’s belief at trial that a
shifting of the burden of proof to the Commissioner would ob-
viate any need to mount a substantive rebuttal defense.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 29
01-4321, 01-4322, & 02-1220

fails as well. The Commissioner is allowed the latitude
to amend his pleadings and even adopt entirely new
theories supporting assessed deficiencies without trigger-
ing Rule 142’s shift in burden, so long as the new theory
is not inconsistent with the original allegation, does not
require new evidence in its support, nor increases the
amount of the deficiency. See, e.g., Friedman v. Comm’r, 216
F.3d 537, 543 (6th Cir. 2000) (“A new position taken by
Commissioner is not necessarily a ‘new matter’ if it mere-
ly clarifies or develops Commissioner’s original deter-
mination without requiring the presentation of different
evidence, being inconsistent with Commissioner’s original
determination, or increasing the amount of the deficiency.”);
Abatti v. Comm’r, 644 F.2d 1385, 1390 (9th Cir. 1981)
(same); Achiro v. Comm’r, 77 T.C. 881, 890 (1981) (same).
The problem for Kanter is that the Commissioner’s
amendment did not offer a new theory for the alleged
deficiency. The theory under which the Commissioner
proceeded at all times was that specific transactions
produced taxable income that was reported by BRT but
which was properly taxable to Kanter by virtue of the
grantor trust provisions of the tax code.17 The case relied
upon by Kanter here supports our conclusion. Achiro

17
The Commissioner appears to be offering to split the baby
with respect to the burden of proof issue by conceding that he
bears the burden to prove that BRT actually had taxable income
in the form of capital gains in 1986, but claiming he has met
that burden. There can be no serious dispute that the monies
in question were reported as earned in 1986 by BRT. It was
Kanter’s own accountant, Gallenberger, who, on redirect by
Kanter, provided the testimony with respect to this fact. (Tr. at
4455-4501.) The only substantive issue in dispute is Kanter’s
status as grantor and owner of BRT under the IRC’s grantor
trust provisions, a theory unaffected by the amendment.
30 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

involved an amendment under which the Commissioner
alleged for the first time that a deduction was improper
under a section of the tax code completely different from
the section originally argued. 77 T.C. at 889-90; see also
Shea v. Comm’r, 112 T.C. 183, 190-92 (1999). The Com-
missioner’s amendment here presented a much more mod-
est change, more akin to a clarification of the orig-
inal allegation. Nor is Kanter correct when he alleges
that the amendment increased the assessed deficiency.
The stated deficiency remained constant, and involved
the same income from the same transactions, but was
re-allocated from one disputed year to another disputed
year to correct a calender error that did not prejudice
Kanter’s case.18 The Commissioner did not propose addi-
tional income nor require Kanter to defend against a
larger deficiency than had been assessed before the amend-
ment. Therefore, it is incorrect to claim that the amend-
ment resulted in “an entirely new and increased defi-
ciency in a different year.” (Pet. Br. at 46 (emphasis in orig-
inal).) The Tax Court was correct in determining that the
amendment did not shift the burden of proof to the Com-
missioner.

18
This should obviously not be read to preclude the possibility
that an amendment of the Commissioner’s pleadings to shift
an assessed deficiency from one year to another would result in
a shifting of the burden under Rule 142(a)(1). But where, as here,
the amendment results from a good faith error in the timing
of when specific income was earned from specific transactions
and does not involve any change in the underlying theory of the
deficiency, there is no shifting of the burden of proof to the
Commissioner.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 31
01-4321, 01-4322, & 02-1220

3. Kanter was the grantor of BRT
Although Kanter argues principally that the Commis-
sioner should have borne the burden of proving that Kanter
was the grantor and owner of BRT, and that the Com-
missioner could not meet that burden, Kanter maintains
that, regardless of burden, he is not taxable on BRT’s
income under the IRC’s grantor trust provisions. A finding
of grantor status is a factual finding that we review for
clear error. Scott v. Comm’r, 226 F.3d 871, 874 (7th Cir.
2000). Kanter has failed to show that the Tax Court’s
decision was clearly erroneous.
Despite the trust document’s showing that Beatrice
Ritch was the grantor of BRT, the familiar principle of
substance over form views as the true grantor the one
who principally funded the trusts. Schulz v. Comm’r, 686
F.2d 490, 496 (7th Cir. 1982); United States v. Buttorff, 761
F.2d 1056, 1060-61 (5th Cir. 1985). In Schulz, for ex-
ample, the petitioner’s wife was considered the grantor of
a family trust because both the Commissioner and this
court disregarded the conveyance of the wife’s assets,
which were subsequently used to fund the trust in ques-
tion, to the petitioner. 686 F.2d at 496. The wife, in sub-
stance, provided the funds for the trust, and the form of
the funding, by routing the funds through the petitioner,
was ignored. Similarly, although Kanter was not listed
in the trust document as a grantor, and, even if Beatrice
Ritch actually did contribute $100 towards the funding
of each BRT trust, there is evidence that Kanter contrib-
uted to BRT income and assets he earned, to substantially
fund the twenty-five trusts.
The Tax Court found that Kanter transferred to BRT
income and assets associated with his services in the
Cablevision transactions as well as others. IRA, 78 T.C.M.
(CCH) at 1098. Kanter provided no evidence (other than
32 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

the trust document itself) to show that Beatrice Ritch
actually funded the trusts nor any evidence to show from
whence the substantial assets owned by BRT originated.
Kanter’s assertion that he merely ceded investment op-
portunities in Cablevision to BRT does nothing to under-
mine the Tax Court’s findings and, further, depends on
his credibility, which the court found to be lacking. Be-
cause Kanter was the principal source of the funding of
BRT, he is deemed a grantor of BRT. See 26 C.F.R. § 1.671-
2(e)(1) (“[A] grantor includes any person to the extent
such person either creates a trust, or directly or indirectly
makes a gratuitous transfer . . . of property to a trust. . . .
If a person creates or funds a trust on behalf of another
person, both persons are treated as grantors of the trust.”).
Kanter argues that the Tax Court’s finding that he
was the grantor is directly contrary to an Illinois trial
court decision, in which the Cook County Circuit Court
determined that the Cablevision partnership interests
did not constitute property of Kanter’s law firm because
they did not result from payment of fees for legal services.
Statland v. Levenfeld, No. 84 CH 6494 (Ill. Cir. Ct., Ch. Jan.
28, 1988). Kanter argues that (a) the state court rul-
ing stands for the proposition that the Cablevision part-
nership interests were not in payment for any services
(not just legal services) but were rather investments
and (b) the state court ruling is determinative and bind-
ing on the matter. Kanter overstates the holding of the
cited case. The case involved a former law partner of
Kanter, who alleged that the Cablevision partnership
interests were the property of the partnership because
they were provided in payment for legal services. The
Illinois court disagreed and held that the Cablevision
partnership interests were not the product of legal fees
paid to Kanter’s law firm. The court did not hold, how-
ever, that the Cablevision partnership interests were not
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 33
01-4321, 01-4322, & 02-1220

in payment of fees for services furnished by individual
law firm partners in securing financing and investors
for Cablevision, which is what the Commissioner alleges
here. The trial court did, at various times, refer to the
Cablevision partnership interests as individual invest-
ments, but it also spoke of the activities of Kanter and
his partners in working to obtain financing and investors
for Cablevision. None of these dicta contradicts the posi-
tion of the Commissioner nor renders the factual findings
of the Tax Court clearly erroneous.

4. Kanter was the substantial owner of BRT
Generally, if a grantor of a trust has the power to dis-
pose of the beneficial enjoyment of that trust through a
power of appointment, then the grantor is treated as the
owner of the trust and the income of the trust must
be included in the income of the grantor. 26 U.S.C. §§ 671,
674(a); 26 C.F.R. § 1.674(a)-1. Kanter argues that he three
times renounced his beneficial interest in BRT and, by
those renunciations, lost the power of appointment that
he had under the trust document. But the Tax Court notes
that, after the third of Kanter’s renunciations, sixty new
beneficiaries were added to BRT.19 Kanter was the only
person who ever had the power under the trust document
to appoint new beneficiaries. The most logical inference
(which the Tax Court drew) is that Kanter himself ap-
pointed the new beneficiaries and that his earlier renuncia-
tions were shams. Kanter fails to rebut this. Kanter’s only
argument directly on this issue appears in his reply brief,
in which he argues that the Tax Court improperly refused
to reopen the record to admit evidence that Kanter’s

19
The new beneficiaries were all trusts—named and numbered
variations of “JSK Trust.” IRA, 78 T.C.M. (CCH) at 1094-95.
34 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

children were the grantors of the various JSK Trusts that
had been added as beneficiaries of BRT.20 (Reply Br. at 18.)
This purported evidence would not be probative of the
issue whether Kanter had exercised the power of appoint-
ment under BRT. The Tax Court’s findings that Kanter
was the grantor of BRT and that he held a power of ap-
pointment of beneficiaries of BRT were not clearly errone-
ous. Therefore, the Tax Court’s finding that Kanter is
taxable on BRT’s income in 1986 (and 1987) is also not
clearly erroneous.
As an alternative, the Tax Court also found that Kanter’s
borrowing from BRT without repayment and without
adequate security subjected Kanter to liability for BRT’s
income. See 26 U.S.C. § 675(3) (“The grantor shall be
treated as the owner of any portion of a trust in respect of
which . . . . [t]he grantor has directly or indirectly bor-
rowed the corpus or income and has not completely
repaid the loan, including any interest, before the begin-
ning of the taxable year.”). It appears undisputed that
Kanter had borrowed money from BRT in a way that
subjects him to liability under § 675(3), and that at the
beginning of 1987 he still owed BRT $287,030. This would

20
A possible logical alternative argument not made by Kanter
(because, we must assume, it is not valid) is that the appoint-
ments were made by Weisgal under some power he possessed
as trustee. The Tax Court, the Commissioner and Kanter all
spend significant time arguing whether Weisgal is or is not an
independent and adverse trustee. An affirmative determination
of that question would be necessary if Weisgal were to have
appointed the sixty new beneficiaries or if Kanter were able to
prove that he (Kanter) did not appoint them. Because we find
that the Tax Court’s determination that Kanter exercised a
power of appointment was not clearly erroneous, we need not
consider whether or not Weisgal was an independent and ad-
verse trustee of BRT.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 35
01-4321, 01-4322, & 02-1220

be sufficient for Kanter to incur liability for 1987.21 There
are, however, no findings by the Tax Court as to any
amount Kanter owed to BRT as of January 1, 1986. There-
fore, there could be no tax liability for Kanter in 1986
based on § 675(3). In the end this conclusion does not
affect ultimate tax liability because under § 674 Kanter
remains liable for both 1986 and 1987.
In conclusion, we affirm the Tax Court’s determination
that Kanter was the grantor of BRT in 1986 and 1987 and
is taxable on BRT’s income for those years.

IV. George Washington Painting
A. Facts
In 1980, Kanter was approached by Richard Feigen, a
client, who wanted help in securing funding to buy a
painting of George Washington located in England that
Feigen believed to be by John Trumbull.22 Kanter put

21
The existence of these facts, however, would raise an additional
issue, which we will not attempt to resolve today. Would we, as
Kanter claims, need to analyze the amount of the loans in relation
to the trust’s income during the years the loans were made and
from that determine what portion of the trust income from 1987
is attributable to Kanter? See Bennett v. Comm’r, 79 T.C. 470,
484-85 (1982). Or can we, as the Commissioner urges, merely
consider the significant amount of the loans as indicative of
Kanter’s total control over BRT’s income and therefore attribute
all of the income for 1987 to Kanter? See Benson v. Comm’r, 76
T.C. 1040, 1047-48 (1981).
22
John Trumbull was a painter of scenes and individuals from the
time of the founding of the United States. He is, perhaps, most
well known to the general public as the painter of the famous
“Declaration of Independence” painting that dramatized (more
(continued...)
36 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

Feigen in touch with another client, Mr. Rappaport,23 in
Switzerland, who agreed to finance the purchase of the
painting. The transaction closed. After the purchase, the
painting was discovered not to be a Trumbull, and the
seller agreed to rescind the sale. As a result of exchange
rate and interest rate changes, Rappaport, who had ad-
vanced the funds, lost money. Rappaport wanted to be
made whole, and when rebuffed, threatened to sue Feigen
and Kanter for his claimed loss. Kanter, in convincing
Feigen to reimburse Rappaport, agreed to provide $94,231
of his own funds. Kanter also paid $10,000 in legal fees
incurred throughout the course of the transaction.
On his 1980 tax return, Kanter claimed the sum of
$104,231 as a deduction on Schedule C, stating that his
main business activity was “buying and selling paintings.”
The IRS disallowed the claimed loss. The Tax Court found,
based on Kanter’s testimony, that Kanter’s main occupa-
tion was as an attorney and that he did not hold himself
out as an art expert or art dealer. This made the claimed
deduction unrecognizable under 26 U.S.C. § 162 as an
ordinary and necessary business expense. Additionally,
the Tax Court did not allow this deduction as a § 212
expense for production of income “because Kanter received
no fees and no contract existed therefor, [and so] the
expenditure did not bear a reasonable and proximate
relationship to the production of income.” IRA, 78 T.C.M.
(CCH) at 1121. “[Kanter] merely served as an intermediary

22
(...continued)
accurately, fictionalized) the scene of the signing of the Declara-
tion of Independence, and that is familiar to almost every
American schoolchild from its reprinting in countless American
History textbooks.
23
Neither the parties’ briefs nor the trial transcript reveal Mr.
Rappaport’s first name.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 37
01-4321, 01-4322, & 02-1220

to introduce Feigan to another friend, Rappaport. There
was no written contract between Feigan and Kanter for
the sharing of profits.” Id.

B. Analysis
The Commissioner’s determination that Kanter’s ex-
penses associated with the failed sale of the Washington
painting were not legitimate deductions under 26 U.S.C.
§§ 162 and 212 is a finding of fact that we review for
clear error. Reynolds v. Comm’r, 296 F.3d 607, 615 (7th
Cir. 2002); Buelow v. Comm’r, 970 F.2d 412, 415 (7th Cir.
1992).
The Tax Court found, essentially, that Kanter could
not deduct the expenses under §§ 162 and 212 because
Kanter’s business was the practice of law, not art, and
there was no evidence that Kanter had an agreement
with Feigen to receive fees or share profits from the pur-
chase and planned resale of the painting. The Tax Court
simply did not believe the “self-serving and uncorroborated”
testimony of Kanter. IRA, 78 T.C.M. (CCH) at 1121. Given
the totality of the Tax Court’s findings that Kanter sys-
tematically engaged in extensive (non-law related) busi-
ness dealings whereby he “entered into arrangements pur-
suant to which he would use his . . . contacts . . . to assist
individuals . . . in obtaining business opportunities or
in raising capital for business ventures[,]” we find it
implausible for the Tax Court to conclude that Kanter
was not engaged in such dealings when he helped Feigen
secure financing from Rappaport. IRA, 78 T.C.M. (CCH)
at 970.
Without excessively detailing the transactions relating
to the Five that we summarized in Part II, we note that
the Tax Court’s opinion went to considerable lengths to
confirm deficiencies against Kanter based on a character-
38 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

ization of Kanter’s “business” as ranging far beyond the
simple practice of law. In each of the transactions involv-
ing the Five, the foundation for the Tax Court’s determina-
tion that Kanter consistently understated his income
was its findings that time after time Kanter provided non-
legal business services in facilitating business opportuni-
ties for the Five with Prudential, and that he was paid
handsomely for that facilitation. It is difficult for us to
read the first few hundred pages of the Tax Court’s opin-
ion and not be left with the distinct impression that the
Tax Court believes Kanter was involved in this business
“activity with continuity and regularity and . . . [his]
primary purpose for engaging in the activity [was] for
income or profit.” Comm’r v. Groetzinger, 480 U.S. 23, 35
(1987). At the very least, Kanter has shown a distinct
proclivity to seek income and profit through activities
similar to the failed sale of the painting.
Determining whether an activity was engaged in for
profit requires an examination of the relevant factors
outlined in Treasury Regulation 1.183-2. See 26 C.F.R.
§ 1.183-2; Burger v. Comm’r, 809 F.2d 355, 358 (7th Cir.
1987). The nine factors for determining whether Kanter’s
involvement in the sale of the George Washington paint-
ing was carried on for profit include: (1) the manner in
which the taxpayer carries on the activity; (2) the exper-
tise of the taxpayer; (3) the time and effort expended by
the taxpayer in carrying on the activity; (4) the expecta-
tion that assets used in the activity may appreciate in
value; (5) the success of the taxpayer in carrying on other
similar or dissimilar activities; (6) the taxpayer’s history
of income or losses with respect to the activity; (7) the
amount of occasional profits, if any, which are earned; (8)
the financial status of the taxpayer; and (9) elements of
personal recreation or pleasure in carrying on the activity.
26 C.F.R. 1.183-2(b).
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 39
01-4321, 01-4322, & 02-1220

We can, based on Kanter’s testimony and considering
the Tax Court’s other findings, construct a highly prob-
able scenario under which Kanter was to find financing
for Feigen’s purchase in exchange for part of the antici-
pated profits. Under factor (1), this manner of doing busi-
ness, while not well documented, is consistent with the
method pursued in other transactions detailed by the
Tax Court. Under factor (2), Kanter’s apparent expertise
in facilitating financing transactions and putting people
together for deals in order to generate income was so
evident to the Tax Court that it found him liable for large
underpayments of income tax. Additionally, Kanter has
indicated that the art project was attractive because of
Feigen’s expertise in generating sufficient publicity and
excitement about artwork to likely increase the resale
price, thus satisfying factor (4). (Tr. at 4416-30.) Regard-
ing factor (5), Kanter’s obvious success in other facilitation-
of-business ventures was what landed him in trouble with
the Commissioner in the first place. An appealing tale
of the Washington painting scheme as a failed for-profit
venture emerges from this evidence. In fact, while there
is significant evidence that Kanter undertook similar,
though not identical, transactions as the failed painting
purchase for profit, there is no evidence that Kanter
facilitated any other deals of this kind for personal reasons
(i.e., gratuitously). And the Commissioner presents no
evidence contradicting Kanter’s version of events. In fact, by
asserting that, in all of his other disputed transactions
in which income was produced, Kanter had participated in
the manner alleged here and with the kind of profit mo-
tive he alleges here, but arguing that in this single trans-
action, where losses were generated, Kanter participated
for only personal reasons, the Commissioner appears to
want to have his cake and eat it too.
There are certain difficulties in reversing the Tax Court
here. We would have to reverse the Tax Court’s credibility
40 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

finding on the matter. In that connection, neither Feigen’s
testimony, nor Rappaport’s testimony, nor any piece of
specific evidence exists in the record to support Kanter’s
testimony. And we have found elsewhere that, while a
taxpayer’s uncontradicted testimony was sufficient to
demonstrate that the Commissioner’s determination was
erroneous, the Tax Court can disregard that testimony if
it is not credible. Lerch v. Comm’r, 877 F.2d 624, 631 (7th
Cir. 1989). The Tax Court did not here believe Kanter’s
claim of a profit motive. While finding Kanter not cred-
ible in this instance is consistent with the Tax Court’s
refusal to find him credible on other issues, it results in a
completely inconsistent and implausible factual scenario—
Kanter’s incurring more than $100,000 in expenses gratu-
itously to facilitate a business transaction where huge
potential profits lie. But without any indication why
this transaction is unique among all the other Kanter
activities, we think the Tax Court was clearly erroneous
in rejecting Kanter’s claim that he was pursuing commer-
cial objectives here as elsewhere.
In conclusion, we find that there must have been a
profit motive in Kanter’s involvement in the aborted
purchase of the George Washington painting; the Tax
Court’s finding to the contrary is clearly erroneous and
we reverse. Kanter’s deduction for the $104,231 of ex-
penses incurred in facilitating the failed sale of the George
Washington painting is allowed.

V. Bank Deposit Analysis
A. Facts
In examining Kanter’s 1982 tax return, the IRS deter-
mined that inadequately documented deposits into three
of Kanter’s bank accounts during that year greatly ex-
ceeded the income Kanter reported on his federal tax
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 41
01-4321, 01-4322, & 02-1220

return. Based on a comparison of the deposit amounts
to Kanter’s tax return for 1982, the Commissioner deter-
mined that Kanter had unreported gross income that year
in an amount of $2,084,017, and issued an assessment
of deficiency. After Kanter produced sufficient records
documenting some of the deposits in question, the Com-
missioner reduced this deficiency to $1,303,207, which
comprised the sum of four specific deposits:

DEPOSIT AMOUNT PAYOR OR SOURCE
$787,129 The Holding Co. (THC)24
$40,000 Computer Placement
Services, Inc. (CPS) 25
$190,078 Administration Co.
(Special E Account)
$286,000 Administration Co.
(Special Account)

The Tax Court found that the Commissioner had pro-
duced sufficient evidence to create a presumption of
correctness in the indicated deficiency. The bank
deposit analysis method was a reasonable method of
reconstructing income, and deposits from THC, CPS and
the Administration Co. accounts often included taxable

24
THC was a Kanter entity incorporated in 1976. Its purpose, like
that of IRA, was the making of investments. One of the relevant
subsidiaries of THC was Zion Ventures, Inc. (Zion). See infra Part
VI. The stock of THC was substantially owned by the BRT and
Everglades Trusts 1-5 (Everglades Trusts), which were Kanter
trusts whose income was attributable to Kanter via the IRC’s
grantor trust provisions, 26 U.S.C. §§ 671 et seq.
25
The record does not indicate who holds legal or beneficial
ownership of CPS.
42 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

income. Therefore it was proper, the Tax Court ruled, for
the Commissioner to determine gross income from an
analysis of total deposits to Kanter’s bank account minus
any deposits properly excluded from income and to as-
sess a deficiency for the excess of that income over the
reported income. The Tax Court found that Kanter had
not adequately documented that the four deposits in
question were loans, and they were properly included in
his gross income under the deposit analysis. Moreover,
the Court did not find the testimony of Kanter’s account-
ant, Gallenberger, credible on the issue.

B. Analysis
The Tax Court’s determination that a taxpayer has
unreported income is a finding of fact that we review for
clear error. Reynolds, 296 F.3d at 612. The Commis-
sioner’s assessment of a deficiency is presumed correct, but
can be overcome by rebuttal evidence presented by the
taxpayer. Pittman, 100 F.3d at 1313.
Kanter has three arguments with respect to the defi-
ciency determined by the bank deposit analysis: first, the
change in the amount of the deficiency for 1982 under the
bank deposit analysis constituted a “new matter” under
Tax Court Rule 142 that required the burden of proof
to shift to the Commissioner, and with that burden the
Commissioner cannot prevail. Second, the lack of evi-
dence on this issue made the deficiency a “naked assess-
ment,” and it was, therefore, improper to give the Com-
missioner’s assessment of a deficiency the usual presump-
tion of correctness. See Weimerskirch v. Comm’r, 596 F.2d
358, 360 (9th Cir. 1979) (finding no presumption of cor-
rectness when Commissioner’s assessed deficiency lacks
any reasonable foundation in the evidence). Finally, Kanter
argues that the Tax Court clearly erred in finding a defi-
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 43
01-4321, 01-4322, & 02-1220

ciency in light of the evidence presented. All of these
arguments fail.
First, there is no merit in Kanter’s contention that the
Commissioner’s reduction in the amount of deficiency
assessed in 1982 under the bank deposit analysis is a
new matter requiring a shift in the burden of proof. The
Commissioner’s concession that part of the original defi-
ciency was properly excluded from Kanter’s income is not
a new theory, is not inconsistent with the original as-
sessment of deficiency, does not require new or different
evidence from Kanter and does not increase the assessed
deficiency. See discussion supra Part III. The same theory
of bank deposit analysis was being applied before and
after the Commissioner’s concessions, and the resulting
deficiency was reduced, not increased, when Kanter pro-
duced documentation demonstrating to the Commissioner’s
satisfaction that certain deposits were not income. The
remaining, insufficiently documented deposits, therefore,
do not constitute a new matter.
Nor can Kanter escape the presumption of correctness
by relying on the “naked assessment” exception of
Weimerskirch. “The general rule is that a presumption of
correctness attaches to the Commissioner’s deficiency
determination; the taxpayer has the burden of disproving
it. A narrow exception exists where the determination is
arbitrary and erroneous or without rational foundation.”
Pfluger v. Comm’r, 840 F.2d 1379, 1382 (7th Cir. 1988)
(citations omitted). It is not disputed that “before the
Commissioner can rely on [the] presumption of correctness,
the Commissioner must offer some substantive evidence
showing that the taxpayer received income from the
charged activity.” Weimerskirch, 596 F.2d at 360. But the
threshold for properly invoking the presumption is not as
high as Kanter would have us believe, nor is the evi-
44 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

dence presented by the Commissioner as thin as that pre-
sented in Weimerskirch.
In Weimerskirch, the Commissioner assessed a deficien-
cy based on more than $24,000 of unreported income from
the taxpayer’s alleged sale of heroin. Id. at 359. The
Commissioner, however, presented no evidence from which
one could even infer that Weimerskirch was involved in
heroin sales in any way. There were, for example, no
records of bank deposits, net worth, or cash expenditures.
Id. at 361-62. The deficiency was calculated based on
an IRS agent’s purely hypothetical calculation of what
income would be realized from a given level of heroin
sales each week over a given period of time. Id. at 359.
Not only was the deficiency calculation completely di-
vorced from any evidence of actual or inferrable heroin
sales by Weimerskirch, but the entire method of calcula-
tion used was unsupported by evidence. Id. The Commis-
sioner’s attempt to attach the presumption of correctness
to the assessed deficiency in Weimerskirch was, in every
sense of the word, naked.
In contrast, the presumption of correctness in the pre-
sent case appears far more modestly appareled. The Com-
missioner’s use of bank deposits as circumstantial evi-
dence of gross income is an accepted methodology. See, e.g.,
United States v. Ludwig, 897 F.2d 875, 878 (7th Cir. 1990).
The Tax Court found evidence that Kanter was engaged
in income producing businesses. And the court found that
actual deposits were made that had the appearance of
income. IRA, 78 T.C.M. (CCH) at 1104; see also United
States v. Esser, 520 F.2d 213, 217 (7th Cir. 1975) (describing
test for implementing deposit analysis method of recon-
structing income). There is no dispute about the evidence
of deposits. Consequently, there was sufficient evidence
to support the presumption of correctness.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 45
01-4321, 01-4322, & 02-1220

Lastly, Kanter argues that the uncontradicted evidence
at trial shows that the four deposits in question were
loans and were not income. By uncontradicted, we can
only assume Kanter means uncontradicted by any evi-
dence beyond the evidence we have outlined, establishing,
prima facie, that there was a deficiency during 1982.
Because we have found that the Tax Court properly gave
the Commissioner’s assessed deficiency a presumption of
correctness, we must interpret Kanter’s argument as
claiming that the evidence presented overcame the pre-
sumption. In that respect, Kanter’s argument also fails.
In considering whether Kanter met his burden of proof,
the Tax Court found Gallenberger’s summary and Kanter’s
assertions unconvincing. “No credible evidence was intro-
duced to support Kanter’s assertion that the deposits
were loans. . . . We find the testimony of the accountant,
Gallenberger, unreliable and her analysis fatally
flawed. . . .” IRA, 78 T.C.M. (CCH) at 1104. The Tax Court
also recalled “Gallenberger’s regular practice of record
destruction” and the general lack of any documentation
other than her summary and testimony. Id. at 1104-05. The
evidence that Kanter asserts was “uncontradicted” was
considered by the Tax Court and found wanting. Exhibit
9172PK, which, according to Kanter, demonstrates that
the deposits from CPS, THC, and Administration Co.
were loans, reflects a summary analysis by Linda Gallen-
berger that the Tax Court found not credible. Nor is it
correct for Kanter to say that the Tax Court had deter-
mined previously that one of the deposits of money
from Administration Co. was money already found to be-
long to Kanter. (Pet. Br. at 58.) Kanter cites to a sentence
in the Tax Court’s opinion as to issue 21 (allowable cap-
ital gains and losses in 1987) wherein the court states, “As
indicated previously, funds from the Administration Co.
special E and PSAC special E accounts were Kanter’s
46 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

funds.” IRA, 78 T.C.M. (CCH) at 1126. This sentence, in
context, refers only to the specific funds from the accounts
cited and used in the specific transactions at issue (five
years after the deposits at issue here) in that section of
the Tax Court opinion. These specific funds were Kanter’s
own funds, and he was entitled, therefore, to the basis
he had claimed for the assets he had purchased with those
funds. But Kanter seeks to generalize this statement
about his ownership of specific money to mean that all the
money in the Special E accounts, at all times, already
belonged to Kanter. The Tax Court’s opinion does not
say this.
In conclusion, the Tax Court did not clearly err in its
findings regarding Kanter’s unreported income in 1982
as determined by bank deposit analysis. These findings
are therefore affirmed.

VI. Equitable Leasing’s Payments to THC & Zion
A. Facts
Equitable Leasing Co., Inc. (Equitable) was the wholly
owned company of Joel Mallin, a friend and former law
partner of Kanter. Mallin used Equitable (among other
companies) to promote and structure equipment leasing
transactions to make money for investors. The investors’
capital would be highly leveraged to purchase the equip-
ment to be leased, and the residual value of the equip-
ment at the end of the lease would provide the ostensible
paper profit on the investors’ capital. A principal motiva-
tion behind the investment in the leasing transactions,
however, was the opportunity for tax benefits associated
with the venture. Kanter acted as a middleman, introducing
Mallin to investors for his leasing transactions. In return,
Mallin paid commissions to Kanter entities. The Commis-
sioner issued a notice of deficiency for 1983 that included
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 47
01-4321, 01-4322, & 02-1220

a deficiency of $635,250 with respect to four payments
by Equitable to Kanter entities, Zion, and THC.26

DATE FORM OF PAYEE AMOUNT
PAYMENT
Jan. 4, Bank Zion $317,250
198327 Transfer

Jan. 24, Check THC $9500
1983

June 1, Check Zion $6500
1983

June 30, Bank THC $302,000
1983 Transfer

Total $635,250

The Commissioner alleged that these payments
were commissions paid for Kanter’s procurement of inves-
tors in Mallin’s enterprises. Kanter argued that Zion
and THC were loaned money by Equitable that was then
turned around and invested in Equitable as an accom-
modation to Equitable to enable it to close certain trans-
actions.
The Tax Court found that there was sufficient evidence
to indicate that Equitable had paid commissions to Zion

26
THC was a Kanter-controlled investment company and Zion
was a THC subsidiary. See supra note 24.
27
The Tax Court opinion and the Commissioner’s brief both
indicate that this transfer occurred on January 8, 1983. It is of no
significance to the disposition of the case, but the bank transfer
record (Ex. 9203PK) and the THC adjusting journal entry (Ex.
146, entry 32) both indicate that the transfer took place on
January 4, 1983.
48 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

and THC for Kanter’s services in providing investors to
Mallin. Two of the four payments, for $9500 and for $6500,
were labeled (on the check in payment and in THC’s
adjusting journal entries, respectively) as commissions. The
Tax Court determined that this evidence was sufficient
to support the presumption that all of these payments to
Zion and THC were income to Kanter. In response to
this presumption, the Tax Court found that Kanter had
provided no evidence other than his “uncorroborated, self-
serving testimony” concerning the “accommodation” ar-
rangement with Equitable. IRA, 78 T.C.M. (CCH) at 1103.
The court found, as previously noted, that Kanter was
not credible and that the four payments were income at-
tributable to Kanter.

B. Analysis
Whether or not monies are taxable income to a tax-
payer is a finding of fact that we review for clear error.
Reynolds, 296 F.3d at 612. The Commissioner’s assessment
of a deficiency is presumed correct, but can be overcome
by rebuttal evidence presented by the taxpayer. Pittman,
100 F.3d at 1313.
Kanter argues first that the Commissioner’s assessment
of a deficiency should not be given the benefit of the
presumption of correctness because the Commissioner
“failed to provide any evidence connecting Kanter to this
income.” (Pet. Br. at 59.) This argument fares no better here
than it did when we considered it with respect to the
Bank Deposit issue. There was evidence that Mallin and
Kanter were partners in various investments, and that
Kanter’s law firm had procured investors for Mallin’s
Equitable Leasing transactions. (Tr. at 5213-15.) There
was also evidence that Mallin had paid commissions for
these services to Kanter entities. (Id.) Additionally, at
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 49
01-4321, 01-4322, & 02-1220

least two of the payments in question were documented
as commissions. This was sufficient evidence to provide
a rational foundation for the Commissioner’s assessment.
The Commissioner’s assessment appropriately received
its presumption of correctness. See Pittman, 100 F.3d
at 1313.
Kanter also argues that he has rebutted the Commis-
sioner’s deficiency with evidence that only the $16,000
that was labeled as commissions (comprised of the $9500
and $6500 checks) should be considered commission
payments, and the remainder consisted of loans made as
an accommodation to Equitable. Even accepting Kanter’s
concession that the $9500 and $6500 checks from Equitable
Leasing to THC and Zion, respectively, were taxable com-
mission income, we do not believe he has provided suffi-
cient evidence to show that the two bank transfers of
$317,350 and $302,000 were loans.
Regarding the $317,250 transfer, there is clearly evi-
dence supporting the Tax Court’s finding that the transfer
was a commission paid to Zion, and Kanter has provided
no evidence to rebut this finding despite his control of
the entities involved and his access to the records of those
entities. First, as noted, there was circumstantial evidence
that Equitable Leasing was making payments to THC
and Zion as commissions. Additionally, THC’s adjusting
journal for 1983 has an entry “32” indicating an amount
of $317,250 that was labeled, “Due from Zion—Commission
Income to adj. for commiss. from Eq. Leasing, loaned
to Zion on 1/4/83.” (Ex. 146, THC adjusting journal at 6.)
Finally, Kanter appears to concede in the facts section of
his brief that this amount was received as commission.
In his brief on appeal, Kanter breaks down the $635,250
as including “$317,250 as commission income from Equi-
table (see Ex. 146, THC adjusting journal, p. 6, adjusting
journal entry 32, reflecting commission income of $317,250
50 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

which was paid to THC’s subsidiary Zion as a loan from
THC . . .).” (Pet. Br. at 16.) The Tax Court’s finding
that this payment was commission income was not
clearly erroneous.
What about the June 30, 1983 transfer from Equitable
to THC for $302,000? Against the general circumstantial
evidence of commission payments to THC by Equitable
and the presumption of correctness of the Commis-
sioner’s assessment of deficiency, there is an entry in
THC’s general ledger for June 30, 1983, for $302,000
labeled “Loan from Equitable Leasg.” (Ex. 148, THC general
ledger at 12.) Together with this entry there is an entry
indicating an $8000 transfer three days earlier also la-
beled “Loan from Equitable Leasg.” (Id.) This $8000
transfer is corroborated by a check from Equitable to THC
on June 24, 1983, for $8000 that has a memo line reading,
“loan.” (Ex. 9203PK, check #2391.) The corroboration of
the general ledger entry for the $8000 transfer is indi-
rectly probative of the likelihood that the roughly con-
temporaneous and similarly labeled ledger entry for the
$302,000 transfer may also be correct. These circum-
stances make it more likely that the ledger is accurate in
its indication that the $302,000 transfer was a loan and
not a commission payment.
But there is one additional piece of evidence in the rec-
ord that the Commissioner and Kanter have not men-
tioned. In the THC adjusting journal, entry 59 is a barely
legible entry for $310,000 that appears to read, “N/P—
Equitable Leasing, Commission Income, to reclassify
funds from Eq. Leasing.” (Ex. 146, entry 59.) This entry
is significant because we believe it may also represent
the $302,000 and $8000 transfers and show that those
transfers were commissions. These two transfers were
roughly contemporaneous, and Kanter himself aggregates
them and describes them as a cumulative amount in
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 51
01-4321, 01-4322, & 02-1220

his brief. (See Pet. Br. at 16 (“$310,000 as loans from
Equitable . . . reflecting a $302,000 loan and an $8,000
loan . . . .”).) The $310,000 in entry 59 would appear to be
the same as the $310,000 in the general ledger and as the
$310,000 described by Kanter, comprising the total of the
$8000 and $302,000 transfers. Entry 59 in the THC adjust-
ing journal weighs against the general ledger’s notations
for both the $302,000 and the $8000 transfer and
weighs further in favor of the Tax Court’s finding that the
$302,000 was a commission payment. In any event, this
evidence does, at the very least, make the characteriza-
tion of the $302,000 transfer unclear, and because Kanter
bears the burden of rebutting the Commissioner’s assess-
ment of deficiency and controlled the entities whose rec-
ords could have cleared this matter up definitively, we
cannot say that the Tax Court clearly erred in finding that
the $302,000 was a commission payment to THC for
Kanter’s services.
In conclusion, it was not clear error for the Tax Court
to find that the transfers from Equitable Leasing were
commissions and were taxable income.

VII. Cashmere Investment Assoc.’s transactions
A. Facts
During the 1970s, Kanter was involved in a series of
real estate developments with developer Sam Zell. The
development properties were owned by partnerships
(real estate partnerships). Kanter’s interests in the real
estate partnerships were held through a series of Kanter-
controlled trusts, including the BWK Revocable Trust,
the Everglades Trusts 1-5, and the BWK Family Trusts
(referred to collectively as the grantor trusts). Each of
these trusts was a grantor trust whose income was attrib-
utable to Kanter personally. A detailed breakdown of the
52 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

real estate partnership interests and their associated
financial attributes is provided in the Tax Court’s opinion.
IRA, 78 T.C.M. (CCH) at 1107-11. The interests in these
real estate partnerships had, as of 1982-83, zero basis.
During 1982, Zell expressed his desire to purchase
all of the real estate partnership interests held by the
grantor trusts. Kanter was interested in selling to Zell, but
was concerned that significant gains would be triggered
by an unqualified sale of the real estate partnership
interests held by his grantor trusts. The Tax Court found
that twenty one of the real estate partnership interests
held by the grantor trusts had negative capital accounts;
that is, their liabilities exceeded their bases, by an amount,
in total, of $476,889. IRA, 78 T.C.M. (CCH) at 1108.
Therefore, the unqualified transfer of those interests
would involve the assumption of liabilities in excess of
the bases, and would trigger capital gains to the
seller—Kanter, who was the owner by virtue of the IRC’s
grantor trust provisions. See 26 U.S.C. §§ 671-677.
In 1983, a series of transactions took place that ulti-
mately resulted in the transfer of the real estate partner-
ship interests from the grantor trusts to a Zell-controlled
entity. The transfer took place in three stages.

1. Transfer of real estate partnership interests to
Cashmere
Cashmere Investment Associates, Inc. (Cashmere) was
an inactive “shelf” corporation incorporated in Delaware
in 1982 and controlled by Kanter. On or about May 15,
1983, Kanter directed the grantor trusts to transfer their
real estate partnership interests to Cashmere in what
was intended as a nontaxable exchange under 26 U.S.C.
§ 351 in return for Cashmere common and preferred stock.
Concurrently with the § 351 transfer, the grantor trusts
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 53
01-4321, 01-4322, & 02-1220

also transferred to Cashmere eight promissory notes
payable to, and held by, the grantor trusts with a face
value, in total, of $498,500. The promissory notes were
all dated May 1, 1983, and were payable on August 1,
1983. These promissory notes, according to Kanter, had
a basis equal to face value and increased the total aggre-
gate basis of the transferred property so as to eliminate
the gain that would otherwise have been realized under
26 U.S.C. § 357(c) through the assumption by Cashmere
of the negative capital accounts in the transfer of the real
estate partnership interests. See 26 U.S.C. § 357(c).28

2. Sale of Cashmere stock to Waco
On July 12, 1983, in the next stage of the transfers
to Zell-controlled entities, Kanter directed the grantor
trusts to sell their common and preferred stock in Cash-
mere to Waco Capital Corp. in return for promissory
installment notes totaling approximately $1.5 million. The
grantor trusts reported the income from this sale under
the installment method of 26 U.S.C. § 453.
Waco was a Delaware corporation whose sole share-
holder was BRT. BRT’s beneficiaries were the members of

28
Section 357(c) provides in relevant part:
(c) Liabilities in excess of basis.—
(1) In general. In the case of an exchange—
(A) to which section 351 applies . . .
if the sum of the amount of the liabilities assumed exceeds
the total of the adjusted basis of the property transferred
pursuant to such exchange, then such excess shall be con-
sidered as a gain from the sale or exchange of a capital asset
or of property which is not a capital asset, as the case may be.
26 U.S.C. § 357(c).
54 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

Kanter’s family, who were also the beneficiaries of the
grantor trusts. The Tax Court found that, under 26 U.S.C.
§ 453(f), Waco and the grantor trusts were “related per-
sons.” See 26 U.S.C. § 318(a)(2), (3).
On August 31, 1983, the promissory notes held by
Cashmere were paid off by eight checks drawn on the
Administration Co.’s Special E account. As noted, the
Special E account contained the commingled funds of a
variety of entities, mostly (if not entirely) Kanter enti-
ties, and the Administration Co. accounted internally for
the specific source of a given disbursement. The Adminis-
tration Co.’s general ledger, however, did not specify the
source of the eight checks paying the notes. The checks
themselves indicate, in part, what entity is the payor of
the notes. Three of the promissory notes were ostensibly
paid with funds from BRT, an entity that was not the
maker of the notes in question, and there was no docu-
mentary evidence that BRT was advancing the funds to
the makers of the promissory notes or had, in some
way, assumed the obligations on the notes. IRA, 78 T.C.M.
(CCH) at 1110-11.
As of September 1, Waco held all of the stock in Cash-
mere, and Cashmere’s assets included the real estate
partnership interests and $498,500 in cash (from the
note payments).

3. Sale of Cashmere stock from Waco to Zell
Kanter subsequently negotiated the sale of Waco’s
Cashmere stock to Equity Financial Management Co.
(Equity), an entity controlled by Zell. On September 2,
1983, Waco sold the Cashmere stock to Equity for
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 55
01-4321, 01-4322, & 02-1220

$1,647,500 payable by check.29 Immediately after the
purchase, Zell liquidated Cashmere.
The Tax Court found that this convoluted series of
transactions taking place within a three-and-one-half
month period that ultimately resulted in the transfer of
the real estate partnership interests to Zell was arranged
principally to avoid immediate recognition of gain on the
transfer and otherwise lacked any bona fide business
purpose. IRA, 78 T.C.M. (CCH) at 1113; see 26 U.S.C.
§ 357(b)(1)(A), (B). Therefore, the assumption of liabil-
ities by Cashmere was recognized as money received by
Kanter (through his grantor trusts), and he was required
to be taxed on his gain resulting from the transfer, up to
the full amount of the liabilities. 26 U.S.C. § 357(b).
Additionally, the Tax Court found that the transfer of
the notes with the real estate partnership interests
also lacked any bona fide business purpose and were
principally intended as a means to avoid income tax. The
Tax Court found that the notes represented mere transfers
between and among Kanter-controlled entities, and did
not represent true indebtedness. Therefore, Kanter had
no basis in the notes, and the notes did not, therefore,
increase the aggregate basis in the property transferred
to Cashmere. Under § 357(c), the excess of liabilities
over basis in the transferred property was therefore
recognized as capital gain to Kanter. Because the basis
in the partnership interests was zero, under both § 357(b)
and (c), the full amount of the transferred liabilities
was taxable to Kanter.

29
As noted, Cashmere’s assets included $498,500 in cash plus
the partnership interests. Therefore, the $1,647,500 purchase
price of Cashmere included a purchase price of $1,149,000 for
the real estate partnership interests.
56 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

Additionally, the Tax Court found that the subsequent
sale to Waco using the installment method was a
“dispos[ition] of property to a related person.” 26 U.S.C.
§ 453(e)(1)(A). When Waco then subsequently transferred,
within two years, the Cashmere stock to Equity, the
installment method of reporting was no longer available.
26 U.S.C. § 453 (e)(1), (2). The entire amount realized by
Waco in the second disposition was treated as received
(at the time of the second disposition) by the seller-grantor
trusts in the first disposition. Id.

B. Analysis
Whether the transactions involving Cashmere had
economic substance for federal income tax purposes is a
factual question reviewed for clear error. N. Ind. Pub. Serv.
Co. v. Comm’r, 115 F.3d 506, 510 (7th Cir. 1997). Similarly,
whether the installment method of reporting is available
is a factual question that we review for clear error.
Applegate v. Comm’r, 980 F.2d 1125, 1128 (7th Cir. 1992).

1. The Attempted § 351 Transaction
The tax-free transfer of property to a controlled corpora-
tion solely in exchange for the transferee corporation’s
stock is permitted under 26 U.S.C. § 351. The IRC also
provides a means for preserving § 351 eligibility in cir-
cumstances where the transferee corporation assumes
liabilities of the transferor together with the property
transferred (an event that is economically equivalent to
a transfer of money (boot) from the transferee corpora-
tion to the property transferor). 26 U.S.C. § 357. There
are two limitations, however, to tax-free treatment under
§ 351. First, the taxpayer-transferor must prove by a pre-
ponderance of the evidence that the liabilities were
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 57
01-4321, 01-4322, & 02-1220

not transferred for the principal purpose of tax avoidance
and that the transfer had a bona fide business purpose.
§ 357(b). If the taxpayer fails to clear this hurdle, the
assumption of the liability is treated as money received
by the taxpayer, and the taxpayer recognizes any gain to
the full amount of the liability. 26 U.S.C. §§ 357(b)(1),
351(b)(1)(A). Second, if the amount of the liability trans-
ferred is greater than the basis of the property transferred,
then, in general, the transferor-taxpayer recognizes a
capital gain on the amount by which the liability ex-
ceeds the basis of the transferred property. 26 U.S.C.
§ 357(c)(1).

a. 26 U.S.C. § 357(b)
There can be little question that the Tax Court was
correct when it viewed the totality of the convoluted
Cashmere transactions and found that their only pur-
pose was the avoidance of federal income tax. Kanter’s
argument that § 357(b)(1) does not reach this transaction
is meritless. Within a four-month period of time an inac-
tive shelf corporation controlled by Kanter (Cashmere)
had its stock transferred three times, twice between
Kanter-controlled entities. Within that same time span,
promissory notes, virtually equal in total value to the
total negative capital account balances, were made by
entities controlled by Kanter, transferred (along with
the real estate partnership interests holding the nega-
tive balances) to entities controlled by Kanter and then
satisfied by entities controlled by Kanter. Both Cash-
mere and the promissory notes completed their entire
useful life-cycle within the span of the larger, intended
transaction—transferring the real estate partnership
interests to Zell. Yet neither the promissory notes nor
Cashmere functioned to facilitate the transfer of the real
58 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

estate partnership interests to Zell: the promissory
notes were created, transferred, and satisfied before the
consummation of the sale to Zell, and Cashmere was
liquidated as soon as its stock came into Zell’s possession
leaving Zell with only the desired asset—the real estate
partnership interests. The entire transaction was con-
structed to avoid the recognition of the gain realized on
the assumption of the real estate partnerships’ liabilities
(by, ultimately, Zell). Therefore, the assumption of those
liabilities by Cashmere in the initial stages of the proc-
ess cannot be described as other than having as its princi-
pal purpose the avoidance of federal income tax. See 26
U.S.C. § 357(b).
Kanter’s remaining argument with respect to § 357(b)
appears to be that the intent of that statutory section
was to prevent taxpayers from creating additional liabilities
(like personal loans or debts) to be packaged with assets
contributed in a § 351 exchange in order to extract the
gains contained within the contributed property without
recognition for tax purposes. This kind of intent to avoid
taxes, argues Kanter, is far removed from the present case
where the liabilities were a substantial aspect of the real
estate partnership interests to be contributed. This ar-
gument fails as well. The fact that the liabilities being
contributed were “ordinary business liabilities of the
partnerships” does nothing to save this transaction. As
noted, the entire business of contributing the partner-
ship interests and their associated liabilities to Cash-
mere was a transaction whose only function was the
avoidance of federal tax. Therefore, “taking into consider-
ation the nature of the liability and the circumstances
in the light of which the arrangement for the assumption
was made,” it is clear that the principal purpose of the
assumption of liabilities was the avoidance of tax. 26 U.S.C.
§ 357(b)(1).
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 59
01-4321, 01-4322, & 02-1220

It was not clearly erroneous for the Tax Court to have
found that the assumption of the real estate partnership
interests’ liabilities by Cashmere had as its principal
purpose the avoidance of federal income tax.

b. 26 U.S.C. § 357(c)
The Tax Court also found, alternatively, that § 357(c)
would apply to the Cashmere transactions.30 Section
§ 357(c) is triggered when the amount of the liabilities
assumed exceeds the basis of the property contributed
in the § 351 exchange. The taxpayer is taxed on the amount
by which the liabilities exceed the basis. The Tax Court
found that the contributed promissory notes did not rep-
resent genuine indebtedness and had, therefore, a basis
of zero. Without any additional basis from the promissory
notes, the basis of the contributed real estate partner-
ship interests was zero, and the amount of the liabilities
assumed (in the form of the oft-mentioned negative cap-
ital accounts) necessarily exceeded that zero basis. There-
fore, the gain realized in the § 351 transfer must be recog-
nized to the full extent of the assumed liabilities.
Kanter vigorously argues that the substance of the
promissory notes should be respected and not disre-
garded as mere form, and the notes should be given a basis
equal to their face value. For this argument Kanter
relies heavily on the Ninth Circuit’s determinations in
Peracchi v. Comm’r, 143 F.3d 487 (9th Cir. 1998), where a
taxpayer made and contributed notes to his closely held

30
Section 357(c)(2)(A) gives priority to § 357(b)(1) when both
§ 357(c) and § 357(b)(1) apply. Therefore, the finding under
§ 357(c) is only relevant as the alternative to the previous find-
ing under § 357(b)(1).
60 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

corporation. The Ninth Circuit found substance in Perac-
chi’s promises to pay himself, and increased the basis of
property contributed (in a § 351 exchange) to a figure
greater than the liabilities assumed by the closely-held
transferee corporation. Id.; see also Lessinger v. Comm’r,
872 F.2d 519 (2d Cir. 1989) (finding also that personal
note had face-value basis in hands of transferee corpora-
tion). The hypothetical risk that this note might somehow
become the property of a creditor (through bankruptcy
of the corporation) and that a creditor might then be able
to enforce the note was sufficient to make the note more
than an empty promise. Peracchi, 143 F.3d at 493. The
Ninth Circuit panel realized the potential for abuse of
this holding, however, and cabined it.
We confine our holding to a case such as this where the
note is contributed to an operating business which is
subject to a non-trivial risk of bankruptcy or receiver-
ship. [The closely held company] is not, for example,
a shell corporation or a passive investment company.
Id. at 493 n.14.
Even if we were to accept Peracchi’s underlying prem-
ise that a taxpayer’s self-made obligations to his own
closely held corporation should be respected for tax pur-
poses, in light of the language limiting Peracchi’s holding,
we would not extend that premise to the present case.
Cashmere was a passive investment company that, before
the transactions at issue, was a shelf corporation. And
after the transfer of the real estate partnership interests
to Zell, Cashmere was liquidated. Cashmere was not an
operating business, and, unlike Peracchi, where an insur-
ance corporation needed more assets to meet a minimum
premium-to-asset ratio for regulatory purposes, there
was no underlying business purpose here for these transi-
tory promissory notes. Nor did Cashmere face a “non-trivial
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 61
01-4321, 01-4322, & 02-1220

risk of bankruptcy.” Peracchi is, therefore, quite distin-
guishable from the present case. The promissory notes here
did not represent genuine indebtedness, and the Tax
Court did not clearly err in finding that the promissory
notes had no basis. Therefore, the Tax Court’s conclusion
that the liabilities assumed exceeded the basis of the
contributed property by the full amount of the liabilities
and were taxable to that extent was not clearly erroneous.

2. Disallowance of § 453 Installment Method
The next steps in the sale of the real estate partner-
ship interests to Zell involved, first, the sale of the Cash-
mere stock from Kanter’s grantor trusts to Waco and,
second, the subsequent sale within two months of the
Cashmere stock from Waco to Equity (the Zell-controlled
entity). The grantor trusts reported their gains from the
sale to Waco under the installment method allowed by
26 U.S.C. § 453.31 But § 453(e) limits the use of the install-
ment method in circumstances where there is a second
disposition of the property within two years that is ef-
fected by a person “related” to the original seller. In other
words, if A sells to B, and then B sells to C (within two
years), A cannot report the income from its sale under
the installment method if A and B are “related persons”
under 26 U.S.C. §§ 267(b) or 318(a). The Tax Court found

31
Section § 453(c) states:
For purposes of this section, the term “installment method”
means a method of payment under which the income recog-
nized for any taxable year from a disposition is that propor-
tion of the payments received in that year which the gross
profit (realized or to be realized when payment is completed)
bears to the total contract price.
26 U.S.C. § 453(c).
62 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

that the grantor trusts and Waco were “related persons,”
and that the entire amount of income attributable to
the sale of the Cashmere stock to Waco must be recognized
in 1983. We affirm this finding as well.
Section § 453(f)(1) defines a “related person” for purposes
of determining the reach of § 453(e):
(A) a person whose stock would be attributed under
section 318(a) (other than paragraph (4) thereof)
to the person first disposing of the property, or
(B) a person who bears a relationship described in
section 267(b) to the person first disposing of
the property.
26 U.S.C. § 453(f)(1). Waco’s stock is owned entirely by
BRT, whose beneficiaries were undisputedly the mem-
bers of Kanter’s family. Similarly, Kanter does not dis-
pute that these same family members were the bene-
ficiaries of the grantor trusts. Under 26 U.S.C. § 318(a)(2)
(B)(i), the stock owned by BRT is considered owned by its
beneficiaries. Therefore, the BRT beneficiaries are treated
as owning the Waco stock. Similarly, those same BRT
beneficiaries are also beneficiaries of the grantor trusts,
and their ownership of the Waco stock is imputed “up-
stream,” under § 318(a)(3)(B)(i), to the grantor trusts.
Therefore, the stock of Waco would be attributed to the
grantor trusts under § 318(a), making Waco a person
“related” to the grantor trusts under § 453(f)(1)(A). The
attribution, therefore, makes the sale of the Cashmere
stock to Waco ineligible for the installment method under
§ 453(e).32

32
We note with some trepidation that there was no effort by the
Tax Court to identify the precise actuarial interests of the
(continued...)
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 63
01-4321, 01-4322, & 02-1220

Similarly, as noted in Part III, Kanter was the substan-
tial owner of BRT under the grantor trust provisions of
26 U.S.C. §§ 671 et seq. Therefore, there is an alterna-
tive means by which the grantor trusts and Waco are
“related persons.”33 Under § 318(a)(2)(B)(ii), stock owned

32
(...continued)
beneficiaries of BRT nor how precisely those beneficiaries’
identities matched the beneficiaries of the grantor trusts. This
information would be relevant for determining the exact percent-
age of Waco stock owned by the BRT beneficiaries (who were
also grantor trust beneficiaries), which would then be imputed
to the grantor trusts. Because Kanter did not make this argu-
ment on this issue, however, we will not disturb the Tax Court’s
determination. United States v. Jones, 34 F.3d 495, 499 (7th
Cir. 1994) (finding argument not made before this court in
opening brief is waived).
33
There does not appear to be any obstacle in the statute,
legislative history, or regulations to the attribution of a grantor
trust’s stock ownership to the beneficiaries of a trust as well as
to the substantial owner of a trust under §§ 671 et seq. See The
Attribution Rules, 554-2d Tax Mgmt. Portfolio at A-11 (1996)
(“Apparently, attribution from the [grantor] trust to the beneficia-
ries and from the beneficiaries to the trust would still occur,
even if the grantor or another is deemed to be the ‘owner,’
although the statute and legislative history are ambiguous on
this point and the regulations are silent.”). Nor does any court
appear to have ruled on the issue. Our research unearthed
only one commentator who has suggested that attribution to a
grantor precludes attribution to the beneficiaries. See Shop Talk,
Is Stock Attributed to Beneficiaries of Grantor Trusts?, 65 J. TAX’N
207 (Burton W. Kanter & Sheldon I. Banoff ed., 1986) (“A common
sense interpretation of Section 318(a)(2)(B)(ii) should be that
its specific rule regarding attribution from grantor trusts should
preempt the general rule of trust attribution of Section 318(a)(2)
(B)(i).”). The financial interest in this matter of one of the edi-
(continued...)
64 Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320,
01-4321, 01-4322, & 02-1220

by a grantor trust is attributed to its grantor; BRT’s stock,
therefore, is attributed to Kanter. That is, Kanter him-
self is considered to own the Waco stock owned by BRT.
Following a similar statutory path as before, Kanter’s
status as the substantial owner of the grantor trusts
means that any stock he owns personally is attributed to
the grantor trusts under § 318(a)(3)(B)(ii). Therefore,
Kanter’s attributed ownership of the Waco stock means
that the grantor trusts also own the Waco stock. Because
the grantor trusts are attributed ownership of the Waco
stock under § 318(a), Waco and the grantor trusts are
“related persons” under § 453(f)(1)(A), and the sale of the
Cashmere stock from the grantor trusts to Waco is ineligi-
ble for reporting under the installment method by opera-
tion of § 453(e).
Whether one, the other, or both methods of analysis
are followed, the grantor trusts’ sale of Cashmere stock
to Waco was ineligible for the installment method of
reporting for federal income tax purposes. The Tax Court’s
findings on this issue were not clearly erroneous.

VIII. Naomi Kanter motions
A. Facts
On May 8, 2001, in the midst of the Tax Court’s post-
trial Rule 155 computations, attorney Karen Hawkins
entered an appearance in the Tax Court on behalf of
Kanter’s wife, Naomi Kanter (Naomi), for the purpose of
claiming that Naomi should not be jointly and severally
liable for the Tax Court’s determined deficiencies

33
(...continued)
tors of the article may diminish the persuasive value of the
proposed answer.
Nos. 01-4316, 01-4317, 01-4318, 01-4319, 01-4320, 65
01-4321, 01-4322, & 02-1220

against Kanter. Shortly thereafter, Randall Dick, attor-
ney of record for both Kanter and Naomi, moved to with-
draw his representation of Naomi. By her new counsel,
Naomi first filed a series of objections to the Commis-
sioner’s computations because they held Naomi liable for
fraud penalties. The Tax Court upheld these objections.
(Order, IRA, 6/20/01; App. at 0346.) Naomi then filed
seven motions asking the Tax Court to find that she had
not meaningfully participated in the litigation as pro-
vided in 26 U.S.C. § 6015(g)(2). In the alternative, Naomi
asked that the Tax Court reopen the record in order to
hear additional evidence that Naomi was

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Source: Frix Law Library, https://www.frixlaw.com/law-library/cases/2996510. Public record. Not legal advice.
