This would have
been a great question for my Federal Income Tax exam, if only (1) I had heard
it in time, and (2) it weren’t too politically sensitive to be a proper exam
question. (E.g., one doesn't want students' answers to be influenced by their own political views, or their perceptions as to mine.)
Anyway, here’s a lightly edited & expanded version of my response:
That's an interesting question. The key tax issue is, what
would have been Trump’s legitimate business reason for deducting the payments to Cohen? Clearly there would be tension between Trump’s
(1) saying it was just personal, hence not a campaign finance violation, and
yet also (2) treating it as deductible (if he did).
But here's an odd aspect of it. Suppose we posit that Trump
is a long-time criminal who sought the presidency for multiple reasons, but in
part as a money-making scheme that would give him opportunities to defraud the
U.S. government and the American people by – just to give a partial list –
violating the emoluments clause, putting foreign policy up for
sale, having the U.S. government pay fees to his businesses, serving the interests of foreign governments that were giving him a lot of money, and so forth. To
the extent that he was seeking to maximize the profits from his preexisting business
by becoming president, illegal payoffs to Michael Cohen to help him win the
election might be viewed as an expense of this business.
Among the relevant tax law doctrines here is the one holding that one can't
deduct as business expenses the costs of seeking to enter a new line of business. So, just as law
students can't deduct law school tuition (but an established lawyer may be able
to deduct expenses of paying for continuing legal education), Trump in 2015-2016
couldn't properly deduct the costs, such as paying off Cohen, of seeking the
presidency, if we consider his seeking public office to involve entry into a new business.
But
insofar as he was merely seeking to advance his preexisting criminal career by running for president, the case for the business deduction is strengthened.
In short, I think a strong argument against viewing
deduction of the amounts paid by Trump to Cohen for silencing Stormy Daniels as
improper (whether or not as meeting the mens rea requirement for tax fraud) relates to the view that Trump incurred these
costs as part of an ongoing course of criminal activity, of which his political
career is merely a continuing part. Kind of like Michael Corleone moving the family business to Las Vegas.
So far as the mens rea required for tax fraud is concerned, Trump may
also have reasonably believed that this line of argument made the payments to Cohen a proper
deduction, since surely we know that he was lying when he said publicly that
it was merely a personal and private matter.
A further issue pertains to Internal Revenue Code section 162(c)(2),
which denies deductions for “an illegal
bribe, illegal kickback, or other illegal payment under any law of the United States, or under any law
of a State (but only if such State law is generally enforced), which subjects
the payor to a criminal penalty or the loss of license or privilege to engage
in a trade or business.”
The payoffs to
Daniels via Cohen do not appear to have been an illegal bribe or kickback under
relevant U.S. law - except, of course, for the campaign finance angle, which led to Cohen’s
guilty plea. Does this make it a nondeductible
illegal payment (to Daniels via Cohen) by Trump? Does it matter if we accept the apparent DOJ
position that a president can’t be indicted while in office? Does it further matter that the statute of
limitations will apparently run while he is still in office if he serves for at least five years?
I suppose we could also ask whether the expense could be deducted or instead was required to be capitalized, as an input to creating goodwill. (Or was it merely about preserving existing goodwill? Cf. the pompous, confused, Delphic, and ultimately verging on useless analysis that Justice Cardozo offered in Welch v. Helvering.)
Sounds like a great topic for further legal research by someone (although I don't think it will be me).
UPDATE: A reader points out that, under the so-called INDOPCO regulations (sometimes called the anti-INDOPCO regs, as they involved substantial retreat from the scope of capitalization that was suggested by the eponymous Supreme Court case), Welch v. Helvering-type outlays generally can be expensed, even if there is creation of future value that in principle might seem to support requiring capitalization.
UPDATE: A reader points out that, under the so-called INDOPCO regulations (sometimes called the anti-INDOPCO regs, as they involved substantial retreat from the scope of capitalization that was suggested by the eponymous Supreme Court case), Welch v. Helvering-type outlays generally can be expensed, even if there is creation of future value that in principle might seem to support requiring capitalization.