Case: 17-14439 Date Filed: 05/17/2018 Page: 1 of 7
[DO NOT PUBLISH]
IN THE UNITED STATES COURT OF APPEALS
FOR THE ELEVENTH CIRCUIT ________________________
No. 17-14439 Non-Argument Calendar ________________________
Agency No. 029495-14
RUPERT E. PHILLIPS, SANDRA K. PHILLIPS,
Petitioners - Appellants,
versus
COMMISSIONER OF INTERNAL REVENUE,
Respondent - Appellee.
________________________
Petition for Review of a Decision of the U.S. Tax Court ________________________
(May 17, 2018) Case: 17-14439 Date Filed: 05/17/2018 Page: 2 of 7
Before WILSON, NEWSOM, and FAY, Circuit Judges.
PER CURIAM:
Appellants Rupert and Sandra Phillips were shareholders in Olson &
Associates, a real estate development entity. The Phillipses, among others,
guaranteed loans made to the corporation. When Olson defaulted on its loans, the
third-party lenders sued, and the Phillipses were found jointly and severally liable,
along with the other guarantors and the corporation itself, for the debt. The
Phillipses have yet to make a payment towards these judgments. On subsequent
tax returns, however, the Phillipses took the position that the entry of these
judgments alone entitled them to an increased basis in Olson, along with the tax
deduction that accompanies such an increase. The IRS, and ultimately the Tax
Court, disagreed, and the Phillipses appealed. For the reasons following, we
AFFIRM the judgment of the Tax Court.
I
The facts of this case are not in dispute. Rupert and Sandra Phillips were
married and filed joint tax returns for the years at issue in this appeal. Sandra
Phillips was a 50-percent shareholder in Olson & Associates of NW Florida, Inc.,
an S corporation specializing in real estate development. Rupert Phillips was an
Olson employee.
2 Case: 17-14439 Date Filed: 05/17/2018 Page: 3 of 7
Olson organized special-purpose entities for each of its projects, through
which it obtained bank loans to finance land acquisition and project development.
Each loan was secured by the assets of the relevant special-purpose entity, but was
also guaranteed by Olson & Associates, its shareholders, and sometimes the
shareholders’ spouses.
Like many similar businesses, Olson was hit hard by the economic downturn
in the latter half of the 2000s. Many of its projects failed, and the loans financing
them went into default. Banks brought state court actions for repayment against
the relevant special-entities and the loans’ guarantors, including the Phillipses. In
2008 and 2009, ten of these actions resulted in judgments ordering the sale of the
property securing each loan and holding the corporate debtor and individual
guarantors jointly and severally liable for the remaining debt. As of yet, Ms.
Phillips has not made any payments toward the judgments.
Despite having not yet contributed any money toward the payment of these
judgments, the Phillipses claim that Sandra was entitled to increase her basis in her
Olson stock by virtue of her liability alone. Specifically, the Phillipses argue
Sandra is entitled to additional basis of $1,553,360 for 2008 and $30,187,246 for
2009.
The tax court summarized the tax ramifications flowing from these claimed
basis increases as follows. On their 2008 amended return the Phillipses claimed a
3 Case: 17-14439 Date Filed: 05/17/2018 Page: 4 of 7
Schedule E loss deduction of $3,890,069, an amount $1,455,421 larger than
originally claimed on their 2008 return. For 2009, the Phillipses claimed a
Schedule E loss deduction of $10,518,948 and a Net Operating Loss of
$10,349,265. Under former Section 172(b)(1)(H), the Phillipses elected a five-
year carryback period for this NOL, applying $4,625,394 against their 2004 tax
liability and the remaining $5723,871 against their 2005 liability. They filed for
each of those two carryback years a Form 1045, Application for Tentative Refund,
and received the refund they requested.
The Phillipses timely filed their 2010 return, on which they claimed a
Schedule E deduction of $937,000 for the flowthrough loss from Olson,
presumably relying on the unused portion of Mrs. Phillips’ purported stock basis
increase from 2009, generating an NOL for 2010 of $525,710, though the record
does not establish whether or to which year the Phillipses carried this NOL.
After examining the Phillipses’ returns for the years at issue, the IRS
determined that Sandra was not entitled to any basis increase. Accordingly, the
IRS adjusted downward the Phillipses’ 2008 flowthrough deduction from
$3,890,069 to $2,378,899, and their 2009 flowthrough loss deduction from
$10,518,948 to $2,006,205. This left a 2009 NOL of only $1,672,363, which was
exhausted after application against the Phillipses’ 2004 tax liability, leaving no
remaining NOL for application against their 2005 tax liability. Finally, the IRS
4 Case: 17-14439 Date Filed: 05/17/2018 Page: 5 of 7
eliminated the Phillipses’ claimed 2010 flowthrough loss deduction in its entirety,
obviously leaving no claimed NOL for that year. The IRS then sent the Phillipses
a notice of deficiency reflecting these adjustments, after which the Phillipses
petitioned the Tax Court for review. The Tax Court upheld the IRS adjustments,
determining that an increase in basis required Mrs. Phillips to make an actual
payment toward the judgments rendered against Olson. The Phillipses now appeal,
and contend that their basis in Olson increased by virtue of their liability for the
state court judgments rendered against the corporation alone, regardless of if they
have made any actual payments towards the debt. Under our binding precedent,
however, this is simply not the case.1
II
Section 1366(a) of the Internal Revenue Code permits a shareholder of an S
Corporation to deduct her pro rata share of any net operating loss sustained by the
corporation. This deduction is limited, however, to the sum of “the adjusted basis
of the shareholder’s stock in the S corporation” and “the shareholder’s adjusted
basis of any indebtedness of the S corporation to the shareholder.” I.R.C. §§
1366(d)(1). By its very terms, the indebtedness envisioned by Section 1366(d)(1)
runs directly from the corporation to the shareholder. When the payment of a
corporation’s debts are at issue, such direct indebtedness most often occurs,
1 Our review of the tax court’s decision is de novo. Sleiman v. Comm’r of Internal Revenue, 187 F.3d 1352, 1358 (11th Cir. 1999). 5 Case: 17-14439 Date Filed: 05/17/2018 Page: 6 of 7
obviously, when a shareholder “steps into a creditor’s shoes” making an actual
payment toward the corporation’s debt. See Perry v. Comm’r of Internal Revenue,
47 T.C. 159, 164 (1966). Thus, as a general rule, this Circuit requires the
shareholder make an “economic outlay”—an actual payment—toward the
corporation’s debt before she may claim an increase in her basis in the
corporation’s indebtedness. Sleiman v. Comm’r of Internal Revenue, 187 F.3d
1352, 1357 (11th Cir. 1999); see also Underwood v. Comm’r of Internal Revenue,
535 F.2d 309, 312 (5th Cir. 1976). 2 “The rule [reached] by this interpretation is no
more than a restatement of the well-settled maxim which requires that ‘[b]efore
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Case: 17-14439 Date Filed: 05/17/2018 Page: 1 of 7
[DO NOT PUBLISH]
IN THE UNITED STATES COURT OF APPEALS
FOR THE ELEVENTH CIRCUIT ________________________
No. 17-14439 Non-Argument Calendar ________________________
Agency No. 029495-14
RUPERT E. PHILLIPS, SANDRA K. PHILLIPS,
Petitioners - Appellants,
versus
COMMISSIONER OF INTERNAL REVENUE,
Respondent - Appellee.
________________________
Petition for Review of a Decision of the U.S. Tax Court ________________________
(May 17, 2018) Case: 17-14439 Date Filed: 05/17/2018 Page: 2 of 7
Before WILSON, NEWSOM, and FAY, Circuit Judges.
PER CURIAM:
Appellants Rupert and Sandra Phillips were shareholders in Olson &
Associates, a real estate development entity. The Phillipses, among others,
guaranteed loans made to the corporation. When Olson defaulted on its loans, the
third-party lenders sued, and the Phillipses were found jointly and severally liable,
along with the other guarantors and the corporation itself, for the debt. The
Phillipses have yet to make a payment towards these judgments. On subsequent
tax returns, however, the Phillipses took the position that the entry of these
judgments alone entitled them to an increased basis in Olson, along with the tax
deduction that accompanies such an increase. The IRS, and ultimately the Tax
Court, disagreed, and the Phillipses appealed. For the reasons following, we
AFFIRM the judgment of the Tax Court.
I
The facts of this case are not in dispute. Rupert and Sandra Phillips were
married and filed joint tax returns for the years at issue in this appeal. Sandra
Phillips was a 50-percent shareholder in Olson & Associates of NW Florida, Inc.,
an S corporation specializing in real estate development. Rupert Phillips was an
Olson employee.
2 Case: 17-14439 Date Filed: 05/17/2018 Page: 3 of 7
Olson organized special-purpose entities for each of its projects, through
which it obtained bank loans to finance land acquisition and project development.
Each loan was secured by the assets of the relevant special-purpose entity, but was
also guaranteed by Olson & Associates, its shareholders, and sometimes the
shareholders’ spouses.
Like many similar businesses, Olson was hit hard by the economic downturn
in the latter half of the 2000s. Many of its projects failed, and the loans financing
them went into default. Banks brought state court actions for repayment against
the relevant special-entities and the loans’ guarantors, including the Phillipses. In
2008 and 2009, ten of these actions resulted in judgments ordering the sale of the
property securing each loan and holding the corporate debtor and individual
guarantors jointly and severally liable for the remaining debt. As of yet, Ms.
Phillips has not made any payments toward the judgments.
Despite having not yet contributed any money toward the payment of these
judgments, the Phillipses claim that Sandra was entitled to increase her basis in her
Olson stock by virtue of her liability alone. Specifically, the Phillipses argue
Sandra is entitled to additional basis of $1,553,360 for 2008 and $30,187,246 for
2009.
The tax court summarized the tax ramifications flowing from these claimed
basis increases as follows. On their 2008 amended return the Phillipses claimed a
3 Case: 17-14439 Date Filed: 05/17/2018 Page: 4 of 7
Schedule E loss deduction of $3,890,069, an amount $1,455,421 larger than
originally claimed on their 2008 return. For 2009, the Phillipses claimed a
Schedule E loss deduction of $10,518,948 and a Net Operating Loss of
$10,349,265. Under former Section 172(b)(1)(H), the Phillipses elected a five-
year carryback period for this NOL, applying $4,625,394 against their 2004 tax
liability and the remaining $5723,871 against their 2005 liability. They filed for
each of those two carryback years a Form 1045, Application for Tentative Refund,
and received the refund they requested.
The Phillipses timely filed their 2010 return, on which they claimed a
Schedule E deduction of $937,000 for the flowthrough loss from Olson,
presumably relying on the unused portion of Mrs. Phillips’ purported stock basis
increase from 2009, generating an NOL for 2010 of $525,710, though the record
does not establish whether or to which year the Phillipses carried this NOL.
After examining the Phillipses’ returns for the years at issue, the IRS
determined that Sandra was not entitled to any basis increase. Accordingly, the
IRS adjusted downward the Phillipses’ 2008 flowthrough deduction from
$3,890,069 to $2,378,899, and their 2009 flowthrough loss deduction from
$10,518,948 to $2,006,205. This left a 2009 NOL of only $1,672,363, which was
exhausted after application against the Phillipses’ 2004 tax liability, leaving no
remaining NOL for application against their 2005 tax liability. Finally, the IRS
4 Case: 17-14439 Date Filed: 05/17/2018 Page: 5 of 7
eliminated the Phillipses’ claimed 2010 flowthrough loss deduction in its entirety,
obviously leaving no claimed NOL for that year. The IRS then sent the Phillipses
a notice of deficiency reflecting these adjustments, after which the Phillipses
petitioned the Tax Court for review. The Tax Court upheld the IRS adjustments,
determining that an increase in basis required Mrs. Phillips to make an actual
payment toward the judgments rendered against Olson. The Phillipses now appeal,
and contend that their basis in Olson increased by virtue of their liability for the
state court judgments rendered against the corporation alone, regardless of if they
have made any actual payments towards the debt. Under our binding precedent,
however, this is simply not the case.1
II
Section 1366(a) of the Internal Revenue Code permits a shareholder of an S
Corporation to deduct her pro rata share of any net operating loss sustained by the
corporation. This deduction is limited, however, to the sum of “the adjusted basis
of the shareholder’s stock in the S corporation” and “the shareholder’s adjusted
basis of any indebtedness of the S corporation to the shareholder.” I.R.C. §§
1366(d)(1). By its very terms, the indebtedness envisioned by Section 1366(d)(1)
runs directly from the corporation to the shareholder. When the payment of a
corporation’s debts are at issue, such direct indebtedness most often occurs,
1 Our review of the tax court’s decision is de novo. Sleiman v. Comm’r of Internal Revenue, 187 F.3d 1352, 1358 (11th Cir. 1999). 5 Case: 17-14439 Date Filed: 05/17/2018 Page: 6 of 7
obviously, when a shareholder “steps into a creditor’s shoes” making an actual
payment toward the corporation’s debt. See Perry v. Comm’r of Internal Revenue,
47 T.C. 159, 164 (1966). Thus, as a general rule, this Circuit requires the
shareholder make an “economic outlay”—an actual payment—toward the
corporation’s debt before she may claim an increase in her basis in the
corporation’s indebtedness. Sleiman v. Comm’r of Internal Revenue, 187 F.3d
1352, 1357 (11th Cir. 1999); see also Underwood v. Comm’r of Internal Revenue,
535 F.2d 309, 312 (5th Cir. 1976). 2 “The rule [reached] by this interpretation is no
more than a restatement of the well-settled maxim which requires that ‘[b]efore
any deduction is allowable there must have occurred some transaction which when
fully consummated left the taxpayer poorer in a material sense.’” Underwood, 535
F.2d at 311.
It is true that we have previously held that this requirement—that a taxpayer
guarantor make an actual payment towards a corporation’s debt before she may
recognize an increased basis—may not apply in all cases. Selfe v. United States,
778 F.2d 769, 772 (11th Cir. 1985). We have since clarified, however, that this
requirement does apply unless “the facts demonstrate that, in substance, the
shareholder has borrowed funds and subsequently advanced them to her 2 Decisions of the former Fifth Circuit handed down prior to the close of business on September 30, 1981, are binding on this Court. See Bonner v. City of Prichard, Ala., 661 F.2d 1206, 1209 (11th Cir. 1981).
6 Case: 17-14439 Date Filed: 05/17/2018 Page: 7 of 7
corporation.” Sleiman, 187 F.3d at 1357. Thus, the relevant inquiry is whether at
the loan’s origination the third-party lender views the corporation or the
shareholder as the primary obligor for the debt. In Sleiman, for example, we
determined that the lender looked to the corporation as the primary obligor for
repayment—rather than the taxpayer guarantor—in part because at the creation of
the loan the corporation stood as a viable entity with valuable assets, and held that
the shareholders’ mere guaranty of the loans did not qualify them for an increased
basis in the corporation. Id. Just so here. As the Phillipses admit, each lender
considered Olson & Associates, rather than the shareholder guarantors, as the
primary obligor on the loans at origination. The Phillipses’ liability for the
judgments rendered against Olson, therefore, does not “give[] rise to indebtedness
from the corporation to [them] until and unless [they] pay part or all of the
obligation.” Underwood, 535 F.2d at 312 (internal quotation and citation omitted).
“Prior to that crucial act, liability may exist, but not debt ….” Id. And at least for
purposes of this case, without debt there can be no increased basis.
The judgment of the Tax Court is AFFIRMED.