09-1955-ag Nathel v. Commissioner UNITED STATES COURT OF APPEALS 1 2 FOR THE SECOND CIRCUIT 3 4 5 6…

09-1955-ag
Nathel v. Commissioner
UNITED STATES COURT OF APPEALS 1
2
F OR THE SECOND C IRCUIT 3
4
____________________________________ 5
6
August Term, 2009 7
8
(Argued: February 3, 2010 Decided: June 2, 2010) 9
10
Docket No. 09-1955-ag 11
____________________________________ 12
13
IRA N ATHEL , TRACY NATHEL , SHELDON NATHEL , ANN M. NATHEL , 14
15
Petitioners-Appellants, 16
17
—v.— 18
19
COMMISSIONER OF INTERNAL REVENUE , 20
21
Respondent-Appellee. 22
23
____________________________________ 24
25
Before: K ATZMANN and R AGGI , Circuit Judges, and K OELTL , District 26
Judge.*
27
____________________________________ 28
29
The petitioners appeal a decision of the United States Tax 30
Court (Stephen J. Swift, Judge) finding that capital 31
contributions they made to two S corporations could not be 32
treated as “tax-exempt income” to the corporations for the 33
purpose of increasing, pursuant to 26 U.S.C. § 1367(b)(2)(B), 34
the petitioners’ bases in loans they made to the corporations. 35
The Tax Court also found that the petitioners could not deduct 36
* The Honorable John G. Koeltl, of the United States District Court for
the Southern District of New York, sitting by designation.

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their capital contributions as ordinary losses incurred in a 1
trade or business pursuant to 26 U.S.C. § 165(c)(1) or incurred 2
in a transaction entered into for profit pursuant to 3
§ 165(c)(2). We affirm. 4
_________________________ 5
6
HUGH JANOW , Pearl River, NY, for Petitioners- 7
Appellants. 8
9
TERESA T. MILTON , Attorney (John A. DiCicco, 10
Acting Assistant Attorney General, 11
Steven Parks, Attorney, on the brief), 12
Tax Division, United States Department 13
of Justice, Washington, DC, for 14
Respondent-Appellee. 15
16
_________________________ 17

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JOHN G. K OELTL , District Judge: 1
The petitioners, Ira and Tracy Nathel and Sheldon and Ann 2
M. Nathel, appeal a decision of the United States Tax Court 3
(Stephen J. Swift, Judge) upholding tax deficiencies assessed 4
by the Commissioner of Internal Revenue (the “Commissioner”). 5
On appeal, the petitioners argue that certain capital 6
contributions they made to two S corporations, of which they 7
were shareholders, should be treated as items of “tax-exempt 8
income” to the corporations for the purpose of restoring, 9
pursuant to 26 U.S.C. § 1367(b)(2)(B), the petitioners’ 10
previously reduced bases in loans they made to the 11
corporations. The petitioners contend that as a result of 12
their restored bases, they received no ordinary income when 13
the S corporations repaid the petitioners’ loans. 14
Alternatively, the petitioners argue that because they made 15
the capital contributions to obtain releases from personal 16
loan guarantees made to one of the corporations, the capital 17
contributions should be deductible as ordinary losses incurred 18
in a transaction entered into for profit pursuant to 26 U.S.C. 19
§ 165(c)(2). 20
We conclude that the petitioners’ capital contributions 21
do not constitute “tax-exempt income” to the S corporations 22
and, therefore, that the petitioners are not entitled to 23
increase their bases in their loans. We also conclude that 24

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because the petitioners have not met their burden of showing 1
that the primary purpose of their capital contributions was to 2
obtain releases from their loan guarantees, the petitioners 3
are not entitled to deductions from ordinary income pursuant 4
to § 165(c)(2). Therefore, we affirm the Tax Court’s 5
decision. 6
BACKGROUND 7
The following facts are based on stipulated facts that 8
the parties submitted to the Tax Court. 9
Ira and Sheldon Nathel 1 (the “Nathels”) are brothers who, 10
along with Gary Wishnatzki, organized three corporations that 11
elected to be taxed under Subchapter S of the Internal Revenue 12
Code (the “Code”), 26 U.S.C. §§ 1361–1379. “Subchapter S 13
allows shareholders of qualified corporations to elect a 14
‘pass-through’ taxation system under which income is subjected 15
to only one level of taxation.” Gitlitz v. Comm’r, 531 U.S. 16
206, 209 (2001) (citing Bufferd v. Comm’r, 506 U.S. 523, 525 17
(1993)). S corporation profits are not taxed on the corporate 18
level; instead, they are passed through as taxable income to 19
shareholders on a pro rata basis. 26 U.S.C. § 1366(a)(1)(A); 20
see also Gitlitz, 531 U.S. at 209. 21
In addition to profits, an S corporation shareholder is 22
also taxed on any gain from the shareholder’s sale of 23
1 Ira and Sheldon Nathel filed joint tax returns with their wives,
who are also petitioners in this case.

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S corporation stock, which gain is calculated as the amount 1
realized from the sale in excess of the shareholder’s basis in 2
the stock. See 26 U.S.C. § 1001(a); Craven v. United States, 3
215 F.3d 1201, 1204 (11th Cir. 2000). A shareholder’s basis 4
in stock is generally the price paid for the stock if 5
purchased from a third party or the amount of the 6
shareholder’s capital contributions if the stock is received 7
in exchange for capital contributions. 26 U.S.C. § 1012; 8
Treas. Reg. § 1.118–1 (1960). 9
Because S corporation profits are passed on to 10
shareholders to be taxed at the individual level, to avoid the 11
double taxation of a corporation’s profits, the Code permits 12
shareholders to increase their bases in a corporation’s stock 13
when the corporation receives certain “items of income 14
described” in § 1366(a)(1)(A). § 1367(a)(1)(A); Gitlitz, 531 15
U.S. at 209. Similarly, any losses or deductions that are 16
passed through from an S corporation to shareholders reduce 17
the shareholders’ bases in stock in order to prevent the 18
double deduction of those items. § 1367(a)(2)(B); Gitlitz, 19
531 U.S. at 209. If the deductions passed through by the 20
corporation to a shareholder exceed a given shareholder’s 21
remaining basis in stock in any tax year, the excess 22
deductions are applied to reduce the shareholder’s basis in 23
any indebtedness owed by the S corporation to the 24

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shareholder. 2 § 1367(b)(2)(A). If the shareholder’s basis in 1
indebtedness was so reduced, any net increase in basis in a 2
subsequent tax year, as determined pursuant to 3
§§ 1367(a)(1)(A) and 1366(a)(1)(A), is first applied to 4
restore the shareholder’s basis in indebtedness before it is 5
applied to restore the shareholder’s basis in stock. 6
§ 1367(b)(2)(B). 7
The three S corporations in this case, Wishnatzki & 8
Nathel, Inc. (“W & N New York”), G & D Farms, Inc. (“G & D 9
Farms”), and Wishnatzki & Nathel of California, Inc. (“W & N 10
California”), were organized to operate food distribution 11
businesses in New York, Florida, and California. The Nathels 12
each owned twenty-five percent of the corporations and Mr. 13
Wishnatzki owned fifty percent. 14
In June 1999, the Nathels and Mr. Wishnatzki personally 15
guaranteed $2.5 million in loans made by two banks to G & D 16
Farms. In December 2000, Ira and Sheldon Nathel each made 17
personal loans in the amount of $649,775 to G & D Farms. 18
As of December 31, 2000, the Nathels each had a zero basis in 19
their G & D Farms and W & N California stock. They each had a 20
2 An S corporation shareholder typically would not be entitled to a
deduction upon making a loan to an S corporation and would not include in
income any repayment of the principal by the corporation to the extent it
is less than or equal to the shareholder’s basis in the loan. See Nat’l
Bank of Commerce of Seattle v. Comm’r, 115 F.2d 875, 876 (9th Cir. 1940)
(finding that repayment of money lent is not income). The shareholder’s
basis in the loan would equal the amount of the original principal,
subject to any subsequent adjustments to basis. See § 1012;
§ 1366(d)(1)(B).

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basis of $112,547 in loans they made to G & D Farms and a 1
basis of $3,603 in loans made to W & N California. 2
In February 2001, G & D Farms repaid the Nathels’ 3
December 2000 personal loans in the full amount of $649,775 4
each. In August 2001, the Nathels and Mr. Wishnatzki agreed 5
to a plan to liquidate W & N California and to convey full 6
ownership of G & D Farms to Mr. Wishnatzki and full ownership 7
of W & N New York to the Nathels. Prior to its liquidation, 8
W & N California repaid outstanding loans to the Nathels in 9
the amount of $161,250 each. The Nathels then made capital 10
contributions to W & N California in the amount of $181,396 11
each. The Nathels also made capital contributions to G & D 12
Farms in the amount of $537,228 each. In the parties’ 13
stipulation before the Tax Court, they indicated that the 14
capital contributions to G & D Farms “were made by the Nathels 15
to secure the release of their respective guarantees of [G & D 16
Farms’] debts to the Banks and to obtain [Mr. Wishnatzki’s] 17
agreement to the release of the Nathels from their guarantees 18
and to the reorganization plan.” (Stipulation of Facts 19
(“Stip.”) ¶ 34.) The parties also stipulated that “[a]s a 20
condition for releasing Sheldon and Ira from their guarantees 21
of [G & D Farms’] debt, the Banks and [Mr. Wishnatzki] 22
required Sheldon and Ira to each contribute to [G & D Farms] 23
additional capital in the amount of $537,228.00.” (Stip. 24

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¶ 26.) In sum, in 2001, the Nathels received a combined 1
$1,622,050 in loan repayments from the two corporations and 2
made a combined total of $1,437,248 in capital contributions. 3
In calculating their 2001 taxes, the Nathels treated 4
their capital contributions to G & D Farms and W & N 5
California as constituting “tax-exempt income” to the 6
corporations for the purposes of § 1366(a)(1)(A). Therefore, 7
because the Nathels’ bases in their stock previously had been 8
reduced to zero and because their bases in the loans they made 9
to the corporations were also reduced, the Nathels used their 10
capital contributions to restore their bases in the loans 11
pursuant to § 1367(b)(2)(B). Without such an increase in 12
their bases, the petitioners would have been taxed on the 13
ordinary income that would have resulted from the 14
corporations’ repayment of the petitioners’ loans in amounts 15
above the petitioners’ previously reduced bases. 16
The Commissioner rejected the Nathels’ treatment of the 17
capital contributions. The Commissioner determined that the 18
Nathels’ capital contributions could not be used to offset the 19
ordinary income that resulted from the amount of the 20
corporations’ repayment of the Nathels’ loans above the 21
Nathels’ then-existing bases in the loans. Instead, the 22
Commissioner determined that the capital contributions 23
increased the petitioners’ bases in their G & D Farms and 24

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W & N California stock. Because the petitioners redeemed 1
their stock as part of the reorganization plan, the 2
Commissioner determined that they were entitled to a long-term 3
capital loss in light of their now-increased bases in the 4
stock. The net effect of the Commissioner’s calculation was 5
an increase in the tax owed by the Nathels in 2001. 6
The Commissioner mailed a notice of deficiency dated June 7
21, 2006, to Ira and Tracy Nathel, indicating that they owed 8
an additional $279,847 in income taxes for 2001. The 9
Commissioner also mailed a notice of deficiency dated June 21, 10
2006, to Sheldon and Ann M. Nathel, indicating that they owed 11
an additional $279,722. Both couples filed a timely petition 12
in the Tax Court for a redetermination of the deficiencies. 13
The Tax Court granted the parties’ joint motion to consolidate 14
the cases. In an opinion dated December 17, 2008, the Tax 15
Court rejected the petitioners’ challenges to the deficiencies 16
determined by the Commissioner. 3 Nathel v. Comm’r, 131 T.C. 17
262 (2008). 18
19
20
21
3 In addition to the arguments raised on appeal, the petitioners
argued in the Tax Court that their capital contributions were deductible
as ordinary losses incurred in a trade or business pursuant to
§ 165(c)(1). The Tax Court rejected that argument and the petitioners
have abandoned it on appeal.

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DISCUSSION 1
I 2
We accept the stipulated facts the parties submitted to 3
the Tax Court. We review the Tax Court’s legal conclusions de 4
novo. Reimels v. Comm’r, 436 F.3d 344, 346 (2d Cir. 2006). 5
II 6
The petitioners’ argument that their capital 7
contributions can be used to increase the bases of their loans 8
to the corporations begins with the Code. Section 9
1367(b)(2)(B) allows taxpayers to restore any basis in 10
indebtedness that was reduced in a prior tax year if there is 11
any “net increase” in basis in a subsequent tax year pursuant 12
to § 1367(a)(1)(A). Section 1367(a)(1)(A), in turn, provides 13
that a shareholder’s basis is increased by a corporation’s 14
receipt of “the items of income described in” § 1366(a)(1)(A). 15
Section 1366(a)(1)(A) provides that a shareholder’s pro rata 16
share of a corporation’s “items of income (including tax- 17
exempt income),” among other things, should be taken into 18
account in calculating an S corporation shareholder’s tax. 19
The petitioners make the novel argument that capital 20
contributions constitute “items of income (including tax- 21
exempt income)” for the purposes of § 1366(a)(1)(A). They 22
make this argument despite 26 U.S.C. § 118(a), which provides 23
that “[i]n the case of a corporation, gross income does not 24

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include any contribution to the capital of the taxpayer.” 1
They argue that capital contributions are income, although 2
tax-exempt income. 3
We are aware of no case that has decided whether capital 4
contributions constitute “items of income (including tax- 5
exempt income)” for the purposes of § 1366(a)(1)(A). However, 6
while the question whether “income” in § 1366(a)(1)(A) 7
includes capital contributions has not been resolved, courts 8
frequently have addressed the scope of “income” as used in 26 9
U.S.C. § 61(a) and in the Sixteenth Amendment. 4 Those cases 10
indicate that capital contributions traditionally are not 11
considered to be “income” and, therefore, should not be 12
considered “items of income” under § 1366(a)(1)(A). 13
In determining whether capital contributions constitute 14
“items of income (including tax-exempt income),” we look first 15
4 Section 61(a) of the Code states: “Except as otherwise provided in
this subtitle, gross income means all income from whatever source derived
. . . .”
The Sixteenth Amendment allows Congress to “lay and collect Taxes on
incomes, from whatever source derived, without apportionment among the
several States.” See also U.S. Const. art. I, § 2, cl. 3 (“[D]irect Taxes
shall be apportioned among the several States which may be included within
this Union, according to their respective Numbers . . . .”); U.S. Const.
art. I, § 9, cl. 4 (“No Capitation, or other direct, Tax shall be laid,
unless in Proportion to the Census or Enumeration herein before directed
to be taken.”).
It should be noted that “gross income” in § 61(a) is at least as
broad as the meaning of “incomes” in the Sixteenth Amendment. See Murphy
v. IRS, 493 F.3d 170, 176, 178-79 (D.C. Cir. 2007). The petitioners have
not suggested that the definition of “income” for purposes of
§ 1366(a)(1)(A) should be broader than the meaning of “incomes” under the
Sixteenth Amendment, and we therefore find cases interpreting both
“income” under § 61(a) and “incomes” under the Sixteenth Amendment to be
instructive.

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to the traditional distinction between income and capital. In 1
Eisner v. Macomber, 252 U.S. 189, 219 (1920), the Supreme 2
Court determined that a shareholder’s receipt of a stock 3
distribution was not income to the shareholder and, therefore, 4
Congress’s attempt to tax the stock dividend was not 5
authorized by the Sixteenth Amendment. Rejecting the argument 6
that the shareholder could be taxed on the corporation’s 7
underlying accumulated profits, 5 the Court stated that 8
“enrichment through increase in value of capital investment is 9
not income in any proper meaning of the term.” Id. at 214-15. 10
The Court drew a clear distinction between income and capital, 11
defining income as “the gain derived from capital, from labor, 12
or from both combined.” Id. at 207 (internal quotation marks 13
omitted). 14
Consistent with this definition, in Edwards v. Cuba 15
Railroad Co., 268 U.S. 628, 632-33 (1925), the Supreme Court 16
found that subsidy payments from the Cuban government to the 17
defendant railroad company were reimbursements for “capital 18
expenditures” and were not profits or gains to the 19
corporation, and, therefore, were not income for purposes of 20
the Sixteenth Amendment. An early case by this Court 21
5 The Court noted that a shareholder’s share of a corporation’s
accumulated profits could be taxed, but such taxation would be the
taxation of property because of ownership, not income, and would require
apportionment under Article I, section 2, clause 3 and Article I, section
9, clause 4 of the Constitution. Macomber, 252 U.S. at 217; see also
n. 4, supra.

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similarly distinguished income from capital. In United States 1
v. Oregon-Washington Railroad & Navigation Co., 251 F. 211, 2
213 (2d Cir. 1918), Judge Learned Hand noted that the Code’s 3
use of “income” “unquestionably imports . . . the current 4
distinction between what is commonly treated as the increase 5
or increment from the exercise of some economically productive 6
power . . . and the power itself.” 6 Judge Hand stated that 7
“income” “should not include such wealth as is honestly 8
appropriated to what would customarily be regarded as the 9
capital of the corporation taxed.” Id. 10
Macomber’s limited definition of income was expanded in 11
United States v. Kirby Lumber Co., 284 U.S. 1, 3 (1931) 12
(finding that discharge of indebtedness caused the corporation 13
taxpayer to realize an “accession to income” and was taxable 14
under the Code). Subsequently, in Commissioner v. Glenshaw 15
Glass Co., 348 U.S. 426, 431 (1955), the Supreme Court adopted 16
a broad definition of income as “instances of undeniable 17
accessions to wealth, clearly realized, and over which the 18
taxpayers have complete dominion.” In Glenshaw Glass, the 19
Supreme Court held that a punitive damages award was taxable 20
6 Oregon-Washington’s holding, that discharge of indebtedness that
was “a means of contribution to [the corporation’s] capital account” did
not constitute taxable income to the corporation, Oregon-Washington, 251
F. at 213, was later abrogated by 26 U.S.C. § 108(e)(6), which provides a
mechanism for taxing discharge of indebtedness that was acquired by a
corporation from a shareholder as a capital contribution. We address the
petitioners’ argument that § 108(e)(6) demonstrates that capital
contributions constitute “items of income” for the purposes of
§ 1366(a)(1)(A) below.

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because it was included in the definition of “gross income” 1
under the Code. Id. at 432-33. The Court found that through 2
its then-existing definition of gross income as “income 3
derived from any source whatever,” Congress intended “to exert 4
in this field ‘the full measure of its taxing power’” and thus 5
to tax “all gains except those specifically exempted” by the 6
Code. Id. at 429-30 (quoting Helvering v. Clifford, 309 U.S. 7
331, 334 (1940)); see also Collins v. Comm’r, 3 F.3d 625, 630 8
(2d Cir. 1993). The Court distinguished the narrow definition 9
of income in Macomber, but in doing so, it was careful to 10
maintain the distinction between capital and income: 11
Nor can we accept respondents’ 12
contention that a narrower reading of [the 13
predecessor of § 61(a)] is required by the 14
Court’s characterization of income in 15
[Macomber], as “the gain derived from 16
capital, from labor, or from both 17
combined.” The Court was there 18
endeavoring to determine whether the 19
distribution of a corporate stock dividend 20
constituted a realized gain to the 21
shareholder, or changed ‘only the form, 22
not the essence,’ of his capital 23
investment. It was held that the taxpayer 24
had ‘received nothing out of the company’s 25
assets for his separate use and benefit.’ 26
The distribution, therefore, was held not 27
a taxable event. In that context— 28
distinguishing gain from capital—the 29
definition served a useful purpose. But 30
it was not meant to provide a touchstone 31
to all future gross income questions. 32
33
Glenshaw Glass, 348 U.S. at 430-31 (emphasis added) (citations 34
omitted). 35

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Congress has specifically recognized that capital 1
contributions are not income. In 1954, Congress enacted 2
§ 118(a) of the Code, which provides that, “[i]n the case of a 3
corporation, gross income does not include any contribution to 4
the capital of the taxpayer.” Internal Revenue Code of 1954, 5
Pub. L. No. 83-591, ch. 736, § 118(a), 68A Stat. 3, 39. The 6
legislative history of § 118(a) indicates that the purpose of 7
that section was to codify pre-1954 court decisions holding 8
that certain payments to corporations by nonshareholders 9
should be treated as capital contributions and not as income 10
to the corporations, just as shareholder contributions were 11
not treated as income to the corporations. See H.R. Rep. No. 12
83-1337, at 17 (1954), reprinted in 1954 U.S.C.C.A.N. 4017, 13
4042 (noting that § 118(a) “in effect places in the [C]ode the 14
court decisions” on the subject of contributions from 15
“individuals having no proprietary interest in the 16
corporation”); S. Rep. No. 83-1622, at 18 (1954), reprinted in 17
1954 U.S.C.C.A.N. 4621, 4648 (same). While not explicitly 18
listed, the legislative history most likely referred to 19
several Supreme Court cases delineating the boundaries of 20
capital contributions as distinguished from taxable income. 21
Compare Brown Shoe Co. v. Comm’r, 339 U.S. 583, 591 (1950) 22
(holding that payments to entice the location of a 23
corporation’s factories in certain communities were nontaxable 24

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capital contributions), with Detroit Edison Co. v. Comm’r, 319 1
U.S. 98, 102-03 (1943) (holding that payments from an electric 2
company’s customers were not contributions to capital) and 3
Texas & Pac. Ry. Co. v. United States, 286 U.S. 285, 289-90 4
(1932) (finding that government subsidies to guarantee a 5
railroad a minimum revenue were not contributions to capital). 6
In 1960, the Internal Revenue Service (“I.R.S.”) 7
promulgated Treasury Regulation section 1.118-1, which notes 8
that § 118(a) applies to capital contributions from both 9
shareholders and nonshareholders. The Regulation provides 10
that “voluntary pro rata payments” to a corporation from its 11
shareholders for the purposes of providing “additional funds 12
for conducting [the corporation’s] business . . . do not 13
constitute income” to the corporation. Treas. Reg. § 1.118-1. 14
This Regulation is entitled to deference by this Court and is 15
fatal to the petitioners’ position. See McNamee v. Dep’t of 16
Treasury, 488 F.3d 100, 106 (2d Cir. 2007) (“Because Congress 17
has delegated to the Commissioner the power to promulgate all 18
needful rules and regulations for the enforcement of [the 19
Code], we must defer to his regulatory interpretations of the 20
Code so long as they are reasonable.” (internal quotation 21
marks and citation omitted)); United States v. Mazza-Alaluf, 22
607 F. Supp. 2d 484, 496 (S.D.N.Y. 2009) (“Chevron deference 23

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is warranted for Treasury regulations passed under the 1
authority delegated to it by Congress.”). 2
The petitioners’ argument that capital contributions 3
constitute “tax-exempt income,” despite the traditional 4
treatment of capital contributions as distinct from income, is 5
centered on the relatively recent Gitlitz case. In Gitlitz, 6
the petitioners were shareholders of an insolvent 7
S corporation that realized a discharge of indebtedness. 531 8
U.S. at 210. The S corporation excluded the discharge of 9
indebtedness amount from taxable income pursuant to 26 U.S.C. 10
§ 108(a)(1)(B) and (d)(7)(A), which excludes discharge of 11
indebtedness from gross income if the taxpayer is insolvent. 12
Id. The petitioners then increased their bases in the 13
corporation’s stock by their pro rata share of the discharge 14
of indebtedness under the theory that it was an “item of 15
income [including tax-exempt income],” to the corporation 16
pursuant to § 1366(a)(1)(A). Id. The Commissioner contended 17
that the Code’s exclusion of discharge of indebtedness from 18
the gross income of insolvent taxpayers meant that the 19
discharge of indebtedness at issue was no longer an “item of 20
income” for the purposes of § 1366(a)(1)(A) and could not be 21
used to increase the petitioners’ bases. Id. at 213. 22
The Supreme Court upheld the taxpayers’ treatment of the 23
discharge of indebtedness, holding that § 108(a)’s exclusion 24

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of certain discharge of indebtedness income from gross income 1
does not change its fundamental character as an “item of 2
income.” 7 Id. at 214. The Court noted that § 61(a)(12) 3
explicitly provides that discharge of indebtedness generally 4
is included in gross income. Id. at 213. The Court reasoned 5
that while §§ 101 through 136 exclude certain items from gross 6
income, the “mere exclusion of an amount from gross income 7
does not imply that the amount ceases to be an item of 8
income.” Id. The Court also stated that “[i]f discharge of 9
indebtedness of insolvent entities were not actually ‘income,’ 10
there would be no need to provide an exception to its 11
inclusion in gross income.” Id. at 214. 12
The petitioners argue that, based on the reasoning in 13
Gitlitz, there would be no need to exclude capital 14
contributions from gross income, as § 118(a) does, if capital 15
contributions were not already included in gross income 16
pursuant to § 61(a). The petitioners argue that, therefore, 17
capital contributions are fundamentally income and constitute 18
7 The Supreme Court acknowledged that the result of Gitlitz would be
to allow shareholders a “double windfall”: The corporation’s discharge of
indebtedness income would be excluded and not passed through as taxable
income and the shareholders would be able to increase their bases in
stock. Gitlitz, 531 U.S. at 219-20. However, the Court found that the
result was required by the “plain text” of the Code. Id. at 220. After
Gitlitz was decided, Congress added language to § 108(d)(7)(A) barring the
pass-through of excluded discharge of indebtedness income to the
shareholders of S corporations and eliminating the resulting increase in
basis: “In the case of an S corporation, subsections (a), (b), (c), and
(g) shall be applied at the corporate level, including by not taking into
account under section 1366(a) any amount excluded under subsection (a) of
this section.” Job Creation and Worker Assistance Act of 2002, Pub. L.
No. 107-147, § 402(a), 116 Stat. 21, 40.

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“items of income (including tax-exempt income)” for the 1
purposes of § 1366(a)(1)(A). This argument ignores the 2
critical difference between Gitlitz and this case: Gitlitz 3
addressed payments that explicitly were included in gross 4
income under § 61(a). See § 61(a)(12) (“[G]ross income means 5
all income . . . including (but not limited to) . . . (12) 6
[i]ncome from discharge of indebtedness . . . .”). While the 7
petitioners are correct that the list of items of income in 8
§ 61(a) is not exclusive, the petitioners cannot rely on 9
Gitlitz alone to overcome the long-standing treatment of 10
capital contributions as distinct from income. Gitlitz did 11
not create any new items of income. Gitlitz only held that 12
the nature of discharge of indebtedness as income was not 13
changed by the exclusion in § 108(a). 14
Unlike this case, the Commissioner in Gitlitz admitted 15
that the item at issue—discharge of indebtedness—generally was 16
included in gross income, but argued that the exclusion of 17
discharge of indebtedness of insolvent entities in § 108(a) 18
altered the character of that item. It was only in rejecting 19
this argument that Gitlitz noted that it would be unnecessary 20
to exclude discharge of indebtedness of insolvent entities 21
from gross income if discharge of indebtedness in general were 22
not already income. In this case, capital contributions 23
traditionally have not been included in gross income in the 24

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first instance and the fact that § 118(a) explicitly excludes 1
them does not transform them into “items of income” for the 2
purposes of § 1366(a)(1)(A). 3
The petitioners’ view of the superfluous nature of 4
§ 118(a) is belied by the legislative history of that section. 5
The legislative history of § 118(a) shows that, unlike 6
discharge of indebtedness, Congress did not consider 7
shareholder capital contributions to be generally includible 8
in gross income when it created the exclusion. See State Farm 9
Road Corp. v. Comm’r, 65 T.C. 217, 227 (1975) (noting that 10
§ 118 was “intended as an incorporation of existing decisional 11
law”). As discussed above, § 118(a)’s exclusion of “any 12
contribution to the capital of the taxpayer” (emphasis added) 13
was intended to codify certain cases finding that 14
nonshareholder, in addition to shareholder, capital 15
contributions were not income. Treasury Regulation section 16
1.118-1 underscores this understanding of § 118(a) by 17
explicitly stating that both shareholder and nonshareholder 18
capital contributions “do not constitute income” to a 19
corporation. 20
In addition to their argument based on Gitlitz and § 118, 21
the petitioners argue that § 108(e)(6) demonstrates that 22
capital contributions constitute income. Section 108(e)(6) 23
provides a mechanism for taxing the discharge of any 24

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indebtedness that was acquired by a corporation as a capital 1
contribution. Section 108(e)(6) provides that 2
for purposes of determining income of the debtor 3
from discharge of indebtedness, if a debtor 4
corporation acquires its indebtedness from a 5
shareholder as a contribution to capital— 6
(A) section 118 shall not apply, but 7
(B) such corporation shall be treated as having 8
satisfied the indebtedness with an amount of money 9
equal to the shareholder’s adjusted basis in the 10
indebtedness. 11
12
The petitioners argue that because § 108(e)(6) allows for 13
discharge of indebtedness acquired as a capital contribution 14
to be taxed as income to the corporation, capital 15
contributions must be “items of income” for the purposes of 16
§ 1366(a)(1)(A). However, discharge of indebtedness is 17
explicitly included in gross income in § 61(a)(12) and, under 18
Gitlitz, is an “item of income” for the purposes of 19
§ 1366(a)(1)(A) even when it is exempt from taxation. The 20
fact that Congress chose, when confronted with the confluence 21
of discharge of indebtedness, which is income, and capital 22
contributions, which traditionally have not been considered 23
income, to subject discharge of indebtedness acquired as a 24
capital contribution to taxation does not mean that capital 25
contributions that are not discharge of indebtedness 26

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-22-
constitute “items of income (including tax-exempt income)” for 1
the purposes of § 1366(a)(1)(A). 8
2
We are not aware of any case that has held that capital 3
contributions are “income” under § 1366(a)(1)(A) or any other 4
provision of the Code. On the contrary, the Supreme Court and 5
this Court have repeatedly emphasized the distinction between 6
capital and income. See, e.g., Macomber, 252 U.S. at 214-15; 7
Cuba R.R., 268 U.S. at 632-33; Oregon-Washington, 251 F. at 8
213. The petitioners argue that Glenshaw Glass has overruled 9
the earlier cases’ treatment of capital as distinct from 10
income because it rejected Macomber’s definition of income as 11
“‘the gain derived from capital, from labor, or from both 12
combined.’” Glenshaw Glass, 348 U.S. at 430-31 (quoting 13
Macomber, 252 U.S. at 207). However, the decision in Glenshaw 14
Glass was founded on “the intention of Congress to tax all 15
gains except those specifically exempted.” Glenshaw Glass, 16
348 U.S. at 430. In deciding that the punitive damages at 17
issue in that case were a taxable gain, even though not 18
derived from capital or labor, Glenshaw Glass did not overrule 19
the previous cases’ distinction between capital and income. 20
8 The legislative history of § 108(e)(6) indicates that it was
enacted to override the decision of the Court of Appeals for the Fifth
Circuit in Putoma Corp. v. Commissioner, 601 F.2d 734, 751 (5th Cir.
1979), which held that a shareholder’s discharge of indebtedness acquired
by the corporation as a capital contribution was not taxable income to the
corporation because it was a capital contribution. S. Rep. No. 96-1035,
at 18-19, 56 n.24 (1980), reprinted in 1980 U.S.C.C.A.N. 7017, 7033-34,
7068 n.24.

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On the contrary, Glenshaw Glass recognized that Macomber’s 1
definition of income was “useful” in that case precisely 2
because it “distinguish[ed] gain from capital.” Id. at 431. 3
Capital contributions are not gains to a corporation. Rather, 4
they “represent an additional price paid for[] the shares of 5
stock held by the individual shareholders” of a corporation, 6
and are treated as a part of the operating capital of the 7
company. Treas. Reg. § 1.118-1. 8
In arguing that Glenshaw Glass erased the traditional 9
distinction between capital contributions and income, the 10
petitioners also rely on an I.R.S. General Counsel Memorandum 11
dated December 21, 1977 (the “Memorandum”), which addressed 12
whether certain nonshareholder contributions made to a public 13
utility constituted excludable capital contributions under 14
§ 118(a) or constituted taxable income to the utility. The 15
Memorandum concluded that because the contributions were 16
motivated by the nonshareholder’s desire to obtain a more 17
reliable source of electric power, the amounts were taxable 18
income, not contributions to capital. In providing a history 19
of the taxation of nonshareholder capital contributions, the 20
Memorandum noted that “the constitutional basis” of Cuba 21
Railroad “seems to have been considerably weakened” by 22
Glenshaw Glass and its progeny. I.R.S. Gen. Couns. Mem. 23
37,354 (Dec. 21, 1977) (citing State Farm Road Corp., 65 T.C. 24

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at 227). The Memorandum explained that payments like those 1
made by the Cuban government to the railroad “can no longer be 2
characterized as falling outside the scope of gross income 3
within the meaning of Code § 61.” I.R.S. Gen. Couns. Mem. 4
37,354 (Dec. 21, 1977). Rather, according to the Memorandum, 5
those payments would be part of a “new class of tax-exempt 6
transactions, called contributions to capital, that was 7
codified in 1954 as Code § 118.” Id. 8
I.R.S. General Counsel Memoranda are informal documents 9
written by the I.R.S. Chief Counsel’s office. They provide 10
the Chief Counsel’s opinion on particular tax matters before 11
other I.R.S. officials. The Memorandum at issue in this case 12
includes a disclaimer that it is “not to be relied upon or 13
otherwise cited as precedent by taxpayers.” Id. As a result, 14
the Memorandum is not entitled to deference under Chevron 15
U.S.A. Inc. v. National Resources Defense Council, Inc., 467 16
U.S. 837 (1984), because it is an informal letter that itself 17
renounces any force-of-law effect. 9 See United States v. Mead 18
9 In Morganbesser v. United States, 984 F.2d 560, 563 (2d Cir. 1993)
(quoting Herrmann v. E.W. Wylie Corp., 766 F. Supp. 800, 802-03 (D.N.D.
1991)), this Court noted that “[General Counsel Memoranda] are helpful in
interpreting the Tax Code when ‘faced with an almost total absence of case
law.’” The Court, therefore, found it “arguably permissible” to use
General Counsel Memoranda (“GCMs”) to “instruct the court on how the
[I.R.S.] itself” defines “labor organization,” because they were “the only
real guidance as to what the [I.R.S.] considers a labor organization for
the purposes” of the Code. Id. Courts of Appeals in other circuits have
declined to rely on GCMs. See Tupper v. United States, 134 F.3d 444, 448
& n.5 (1st Cir. 1998) (“GCMs . . . are not authority in this court.”);
Stichting Pensioenfonds Voor de Gezondheid v. United States, 129 F.3d 195,

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Corp., 533 U.S. 218, 226-27 (2001) (holding that Chevron 1
deference is appropriate “when it appears that Congress 2
delegated authority to the agency generally to make rules 3
carrying the force of law, and that the agency interpretation 4
claiming deference was promulgated in the exercise of that 5
authority”); Christensen v. Harris County, 529 U.S. 576, 587- 6
88 (2000) (holding that agency interpretations contained in 7
informal opinion letters are not entitled to Chevron 8
deference). Any “respect” afforded to the Memorandum would 9
only be proportional to its “power to persuade” pursuant to 10
Skidmore v. Swift & Co., 323 U.S. 134, 140 (1944). 11
Christensen, 529 U.S. at 587. 12
In this case, we decline to rely on the Memorandum 13
because it disclaims precedential effect and is not entitled 14
to deference under Chevron. Furthermore, the persuasiveness 15
of the Memorandum is limited in light of the fact that the 16
Memorandum does not address the question whether capital 17
contributions such as those in this case constitute “tax- 18
exempt income” for the purposes of § 1366(a)(1)(A). The 19
Memorandum, like Cuba Railroad, deals only with nonshareholder 20
capital contributions, the scope of which has been clarified 21
by several Supreme Court decisions following Cuba Railroad. 22
200 (D.C. Cir. 1997) (“These ‘GCMs,’ however, have no precedential
value.”); Disabled Am. Veterans v. Comm’r, 942 F.2d 309, 315 n.5 (6th Cir.
1991) (“Such informal, unpublished opinions of attorneys within the
[I.R.S.] are of no precedential value . . . .”).

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See, e.g., Brown Shoe Co., 339 U.S. at 591-93; Detroit Edison 1
Co., 319 U.S. at 103. 2
Finally, the petitioners point to two cases from Courts 3
of Appeals in other circuits that allegedly show that capital 4
contributions constitute income. In one case, the Court of 5
Appeals for the Seventh Circuit referred to “tax-exempt 6
capital contributions.” Am. Med. Ass’n v. United States, 887 7
F.2d 760, 774 (7th Cir. 1989). In the other, the Court of 8
Appeals for the Ninth Circuit addressed whether certain 9
payments were “exempt from federal income tax as contributions 10
to capital.” Washington Athletic Club v. United States, 614 11
F.2d 670, 671 (9th Cir. 1980). The petitioners argue that 12
because the above cases referred to capital contributions as 13
being “exempt” from income, these cases demonstrate that 14
capital contributions are “tax-exempt income” for the purposes 15
of § 1366(a)(1)(A). However, these cases did not hold that 16
capital contributions constitute income. Rather, they 17
discussed, among other things, whether certain membership fees 18
paid to associations constituted capital contributions or 19
taxable income. The fact that these cases may have used 20
imprecise language to express the fact that capital 21
contributions are not subject to taxation does not mean that 22

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capital contributions are income. 10 In fact, American Medical 1
Association explicitly recognized the distinction between 2
capital contributions and income when it noted that if the 3
plaintiff in that case argued that certain funds it received 4
“should be likened to capital contributions, it would argue 5
that those monies should never be considered income.” Am. 6
Med. Ass’n, 887 F.2d at 774 n.15. 7
Therefore, for all of these reasons, we find that the 8
petitioners’ capital contributions do not constitute “items of 9
income (including tax-exempt income)” under § 1366(a)(1)(A) 10
and cannot be used to restore their bases in indebtedness 11
pursuant to § 1367(b)(2)(B). 12
III 13
As an alternative to using their capital contributions to 14
increase their loan bases and thereby reduce their taxable 15
income, the petitioners argue that they should be allowed to 16
deduct their capital contributions to G & D Farms as losses 17
incurred in a transaction entered into for profit pursuant to 18
§ 165(c)(2). The petitioners do not argue that their capital 19
contributions to W & N California should be deductible. 20
10 It is difficult to place too much emphasis on the specific
language in those decisions. In calculating taxable income, in most
circumstances, there is no difference between the case where an item is
included in gross income pursuant to § 61(a) and then excluded from gross
income by another Code section and the case where the item is not
includible under § 61(a) at all.

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Section 165(c)(2) provides that individuals are allowed a 1
deduction from taxable income for “losses incurred in any 2
transaction entered into for profit, though not connected with 3
a trade or business.” In general, a negotiated payment to 4
secure a release from conditional liability under a loan 5
guarantee is deductible as a loss incurred in a transaction 6
entered into for profit. See, e.g., Duke v. United States, 7
No. 75 Civ. 5122, 1977 WL 1082, at *2 (S.D.N.Y. Jan. 31, 8
1977); Shea v. Comm’r, 36 T.C. 577, 582 (1961), aff’d, 327 9
F.2d 1002 (5th Cir. 1964); Lloyd-Smith v. Comm’r, 40 B.T.A. 10
214, 223 (1939), aff’d on other grounds, 116 F.2d 642 (2d Cir. 11
1941). 12
“This court has repeatedly held that, in determining the 13
deductibility of a loss, the primary motive must be 14
ascertained and given effect.” Austin v. Comm’r, 298 F.2d 15
583, 584 (2d Cir. 1962); see also Helvering v. Nat’l Grocery 16
Co., 304 U.S. 282, 289 n.5 (1938) (“[T]he deductibility of 17
losses under [the predecessor of § 165(c)] may depend upon 18
whether the taxpayer’s motive in entering into the transaction 19
was primarily profit.”); Ewing v. Comm’r, 213 F.2d 438, 439 20
(2d Cir. 1954). The burden of proving the requisite motive is 21
on the petitioners. Cf. Sutton v. Comm’r, 84 T.C. 210, 221 22
(1985), aff’d, 788 F.2d 695 (11th Cir. 1986). 23

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-29-
Instead of looking to the “primary motive,” some courts 1
have attempted to ascertain whether the “sole purpose” of a 2
taxpayer’s payment was to secure a release from a loan 3
guarantee before allowing the taxpayer to take a deduction 4
pursuant to § 165(c)(2). See Duke, 1977 WL 1082, at *2; Shea, 5
36 T.C. at 582; Lloyd-Smith, 40 B.T.A. at 223. In Duke, the 6
court denied the taxpayers’ motion for summary judgment 7
because it could not determine if their payment was for the 8
“sole purpose” of securing a release from a guarantee or 9
rather was the purchase price of a capital asset. Duke, 1977 10
WL 1082, at *2. 11
In this case, the Tax Court found that the petitioners 12
“clearly had multiple purposes in making the[ir] capital 13
contributions,” and, therefore, distinguished this case from 14
those that allowed deductions upon finding that payments were 15
made for the “sole purpose” of obtaining releases from loan 16
guarantees. Nathel, 131 T.C. at 274. The Tax Court noted 17
that the parties stipulated that the Nathels made the 18
contributions in connection with the banks’ release of the 19
petitioners’ guarantees, in connection with Mr. Wishnatzki’s 20
assumption of responsibility as a guarantor, and to obtain Mr. 21
Wishnatzki’s agreement to the reorganization plan. Id. The 22
Tax Court found that, therefore, the petitioners did not make 23
the contributions for the “sole purpose of being released from 24

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their guarantees on the bank loans” and, as a result, it found 1
that the contributions were not deductible pursuant to 2
§ 165(c)(2). Id. at 274-75. 3
To the extent the Tax Court required the capital 4
contributions to be for the sole purpose of obtaining releases 5
from the loan guarantees, the Tax Court required too much. 6
The capital contributions need only have been made for the 7
primary purpose of obtaining the releases in order to be 8
deductible as losses incurred in a transaction entered into 9
for profit. However, the Tax Court’s error was harmless 10
because the petitioners did not meet their burden of showing 11
that the primary purpose of the contributions was to obtain 12
the releases from the guarantees. 13
The petitioners argue that the parties’ stipulation 14
before the Tax Court proves that the capital contributions 15
were made for the primary purpose of obtaining the releases. 16
The petitioners point to paragraph 26 of the stipulation, 17
which provides that “[a]s a condition for releasing [the 18
Nathels] from their guarantees of [G & D Farms’] debt, the 19
Banks and [Mr. Wishnatzki] required [the Nathels] to each 20
contribute to [G & D Farms] additional capital in the amount 21
of $537,228.00.” (Stip. ¶ 26.) The petitioners also rely on 22
paragraph 34 of the stipulation, which provides that the 23
Nathels’ capital contributions to G & D Farms “were made 24

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. . . to secure the release of their respective guarantees of 1
[G & D Farms’] debts to the Banks and to obtain [Mr. 2
Wishnatzki’s] agreement to the release of the Nathels from 3
their guarantees and to the reorganization plan.” (Stip. ¶ 34 4
(emphasis added).) 5
While paragraph 26 of the stipulation states that the 6
capital contributions were a condition of the petitioners’ 7
release from their loan guarantees, there is no stipulation 8
that the primary purpose of the contributions was to obtain 9
that release. Paragraph 34 of the stipulation provides that 10
the capital contributions were made for three purposes: (1) 11
to secure the petitioners’ release from the guarantees of 12
G & D Farms’ debts, (2) to obtain Mr. Wishnatzki’s agreement 13
to the release of the Nathels from the guarantees, and (3) to 14
obtain Mr. Wishnatzki’s agreement to the reorganization plan. 15
The stipulation, therefore, suggests that the capital 16
contributions were made to achieve multiple purposes, without 17
indicating which, if any, was the primary purpose. 18
The petitioners point to several cases that demonstrate 19
that payments can have multiple purposes and still be 20
deductible under § 165(c)(2). The petitioners argue that 21
these cases show that the capital contributions here are 22
deductible. The petitioners read too much into these cases. 23
In Rushing v. Comm’r, 58 T.C. 996, 1000-01, 1005 (1972), the 24

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Tax Court distinguished between two payments the taxpayers 1
attempted to deduct: legal expenses connected with the 2
petitioners’ personal guarantee of a corporation’s debt, which 3
the court found to be deductible, and other fees related to 4
the sale of the corporation’s assets, which it found to be not 5
deductible. Rushing simply demonstrates that if a court can 6
determine that the principal purpose of any one of a number of 7
payments was in connection with a transaction entered into for 8
profit, then the payment may be deducted pursuant to 9
§ 165(c)(2). In this case, it cannot be determined what 10
portion of petitioners’ capital contributions, if any, was 11
principally made to obtain the petitioners’ release from the 12
guarantees. 13
The petitioners also point to a case from another 14
circuit, Commissioner v. Condit, 333 F.2d 585, 587-88 (10th 15
Cir. 1964), in which the court found that the taxpayer 16
“attained three objectives” through making a certain payment, 17
including obtaining a release on a loan guarantee, settling a 18
debt with the payee, and transferring the responsibility for 19
winding up a business. The court found that the taxpayer’s 20
payment “was not the payment of a debt within the purview of 21
[26 U.S.C.] § 166(d) but rather a loss incurred in a 22
transaction for profit.” Id. at 588. To the extent that the 23
court in Condit found that the payment had no primary purpose, 24

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but nevertheless was deductible pursuant to § 165(c)(2), it is 1
inconsistent with prior decisions of this Court and we decline 2
to follow it. 3
In addition to relying on the parties’ stipulations 4
regarding the purposes of the capital contributions, the 5
petitioners argue that the fact that G & D Farms and W & N New 6
York “were sold for each corporation’s fair market value” to 7
Mr. Wishnatzki and the Nathels, respectively (Stip. ¶ 46), 8
illustrates that the petitioners’ capital contributions to 9
G & D Farms could not have been part of the price the Nathels 10
paid to obtain Mr. Wishnatzki’s agreement to the sale of the 11
companies. The petitioners argue that, therefore, the primary 12
purpose of the capital contributions was to obtain the 13
petitioners’ release from the loan guarantees. However, there 14
is no reason to believe that the petitioners’ capital 15
contributions were not part of the “fair market value” price 16
for which the corporations were sold as part of the 17
reorganization plan. 18
In their reply brief, the petitioners argue for the first 19
time that their capital contributions were made in connection 20
with a transaction entered into for profit because, as 21
shareholders of both G & D Farms and W & N New York at the 22
time, they signed their personal guarantees of G & D Farms’ 23
loans in order to improve the financial position of both 24

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corporations, in light of the fact that W & N New York’s 1
business allegedly was dependent on receiving produce from 2
G & D Farms. However, the Commissioner does not contest that 3
the Nathels’ personal guarantees of G & D Farms’ loans 4
constituted a transaction entered into for profit. The 5
question is whether the primary purpose of the Nathels’ 6
subsequent capital contributions was to obtain releases from 7
the loan guarantees. The fact that the Nathels expected the 8
guarantees to benefit G & D Farms and W & N New York does not 9
establish the primary purpose of the Nathels’ capital 10
contributions. 11
The petitioners did not meet their burden of showing that 12
the capital contributions were primarily motivated by a desire 13
to obtain releases from the loan guarantees. Therefore, the 14
capital contributions are not deductible as losses incurred in 15
a transaction entered into for profit pursuant to § 165(c)(2). 16
CONCLUSION 17
For all of the reasons explained above, we AFFIRM the Tax 18
Court’s decision. 19

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