
34 THE ST. LOUIS BAR JOURNAL
Summer 2023
Introduction
Together with two of his
brothers, Craig and Kurt, the late
Scott Hoensheid1 was a third-
generation owner and operator
of Commercial Steel Treating
Corporation (“CSTC”), a very
successful metals nishing
company in Michigan. In 2014,
Kurt informed his brothers that
he wanted to retire. Craig and
Scott did not want the company
to assume debt in order to buy
him out. (Apparently, this had
happened twice in the past with
two other brothers.)
Accordingly, they engaged an
investment banking rm to nd
a third-party purchaser. Fairly
quickly, their advisor at that
rm solicited several letters
of intent from various private
equity investors. By April 2015,
the brothers had identied a
likely purchaser, and negotiations
began in earnest. Each of the
three brothers stood to clear $30
million on the transaction, much
of it taxable as long-term
capital gain.
Scott decided he would like
to mitigate his tax burden by
contributing a portion of his
stock to a donor-advised fund
at Fidelity Charitable. The
Internal Revenue Code is very
friendly to such an arrangement.
To the extent unrealized gain
would have been long-term,2
a charitable contribution of
appreciated property is deductible
at fair market value, offsetting
ordinary income,3 while at the
same time, properly structured, it
is not an income recognition event.
Scott's attorney warned him,
however, that it would be
important to complete the gift
"before any purchase agreement
is executed," otherwise the
Internal Revenue Service might
recharacterize the transaction
as an "assignment of income,"
and while he could still claim an
income tax charitable deduction
for the value of the stock
contributed, he would not avoid
recognizing the capital gain.
As we shall see, this advice fell
a little short, but in any event it
appears Scott did not quite
follow it.
As Scott informed his attorney,
he wanted to be "99 percent sure"
the deal would close before he
let go of the stock, because if the
deal fell through, he did not want
to be holding less stock than
either of his brothers. In addition,
because he wanted the value
of the gifted stock, as nearly as
possible, to equal $3 million,
Scott was uncertain until the
last moment exactly how many
shares he wanted to contribute.
Five days before the July 15
closing, Scott delivered a stock
certicate to his attorney, for
eventual redelivery to Fidelity.
The certicate was undated, and
there was a slight discrepancy
between the number of shares
reected on the certicate and
the number of shares Fidelity
ultimately acknowledged
receiving. It was not until two
days before closing that Fidelity
nally had a certicate in hand
and was able to sign off on an
agreement to sell its shares to the
third-party purchaser.
Certainly, this was literally
"before the purchase agreement
was executed," but on
examination of Scott's tax return,
the IRS nonetheless insisted that
the contribution to Fidelity was
an anticipatory assignment of
income, and that Scott should be
taxed on the gain. The Tax
Court agreed.4
Taking a Step Back
In fairness to Scott's attorney,
and despite the fact that this is a
nonprecedential, memorandum
opinion, which should mean that
it simply recites existing law, there
has been some uncertainty in the
caselaw when exactly it is "too late"
to make such a transfer to charity
by Richard M. Wise, CPA, JD
THE ST. LOUIS BAR JOURNAL/ SPRING 2020 47
No Compromise
The Background
By Richard M. Wise, CPA, JD
Back in the late 1990s, a financial
advisor in Atlanta named Mark Klop-
fenstein recommended to a number of
his clients that they invest in a “struc-
tured securities transaction” that was
intended to create artificial tax losses
they might claim in order to offset
recognized taxable gains from other
investments. He invested in several of
these on his own account.
Without getting too deep into the
technical details, which are beyond
the scope of this column’s subject
matter, it would suffice to say that
in each of these transactions the tax-
payer would transfer encumbered
property to a partnership as a capi-
tal contribution -- in some cases,
proceeds of a short sale of Treasury
instruments, subject to the obliga-
tion to repurchase, in other cases,
“paired” put and call options in for-
eign currencies.
The taxpayer would claim a tax ba-
sis in his partnership interest that did
not account for the offsetting liability. Not
much later, when he disposed of his
interest at a price that did take account of
the liability, he would claim a loss.
These strategies were devised by
lawyers for Deutsche Bank, which
marketed them for a number of years.
The lawyers provided opinion letters
to the investors arguing that because
the Internal Revenue Code (“the
Code”) did not expressly address
these scenarios, the taxpayer would
“more likely than not” prevail on
examination.
1
If Mr. Klopfenstein’s
reliance on these opinion letters were
“reasonable”, he would have been
protected from incurring penalties on
any resulting tax underpayments.
2
According to Mr. Klopfenstein’s
understanding, the purpose of these
opinion letters was to protect the tax-
payer from incurring underreport-
ing penalties in the event the Internal
Revenue Service (“IRS”) disallowed
the loss deductions upon examina-
tion or otherwise. The cost of an
opinion letter was, in his words, a
“risk premium.” He later also said he
believed the claimed losses did have
“economic substance.”
Unsheltered
At some point, the IRS became
aware of these transactions, and in a
series of published notices3 starting
in 1999 identified these as “listed”
transactions they would challenge
on the ground that there was no
“economic substance” to the pur-
ported losses.
In 2003, the IRS audited Mr. Klop-
fenstein’s federal tax returns for 1999
and 2000, and assessed very large de-
ficiencies. He filed a timely petition
in United States Tax Court to contest
these assessments, but eventually set-
tled, paying about $1.4 million in taxes
and penalties, plus some amount in in-
terest. He then sued Deutsche Bank on
a theory that they had misrepresented
these transactions as in fact having
“economic substance,” but that action
was dismissed as untimely.
4
Unfortunately, Mr. Klopfenstein’s
problems were just beginning.
Inasmuch as he had continued to
act as a “material advisor,” promot-
ing these transactions to several of
his clients even after IRS had listed them
as tax shelters, and had failed to file the
required disclosure statements,
5
in 2014
the IRS sent Mr. Klopfenstein a Form
5701--Notice of Proposed Adjust-
ment, proposing to assess penalties
totaling some $1.6 million.
The formal assessment was made
in 2016, at which time Mr. Klopfen-
stein offered to settle for $10,000.00,
which was not even “pennies on the
dollar.” The Examination Division
promptly rejected that offer, and Mr.
Klopfenstein filed a protest, taking
the issue up with the Appeals Office.
After some back and forth, the par-
ties agreed to settle for $169,855.00,
slightly over 10.0% of the amount the
IRS had assessed.
And here, almost five hundred words
in, is where our story actually begins.
1. Two of these lawyers were later convicted of tax fraud. Each was sentenced to several
years in federal prison and fined several hundred million dollars, and, of course, each
was disbarred.
2. Code section 6694(a)(2)(C).
3. Notice 99-59, IRB 1999-52, p. 761 (12/27/99), Notice 2000-44, IRB 2000-36, p. 255
(09/05/00), Notice 2003-81, IRB 2003-51, p. 1223 (12/22/03).
4. Klopfenstein v. Deutsche Bank AG, No. 14-CV-00278 (N.D.Ga. 05/13/14), aff’d, No. 14-
12611 (11th Cir. 11/20/14) (unreported).
5. Form 8918 -- Material Advisor Disclosure Statement. The form does not require the
advisor to identify participants, but the advisor is required to maintain lists of partici-
pants, which IRS may demand.
’Tis Better to Give than to Receive
(So Long as You Have a Qualified Appraisal)