Trump’s tax moves raise questions about potential legal exposure

WASHINGTON — Deductions for haircuts, consulting fee write-offs, a family estate that is treated as a business property and an aggressive refund claim could open President Donald Trump to legal risks once he’s out of office.

An analysis published by The New York Times based on more than two decades of Trump’s tax returns the news organization obtained show that Trump took aggressive tax positions and that the IRS is challenging a $72.9 million refund claimed a decade ago in an audit that has yet to be resolved.

If the Internal Revenue Service ultimately prevails, Trump could be liable for millions of dollars in penalties. He potentially could be subject to criminal prosecution if the IRS mounted a case that he knowingly violated the law, though that would be very difficult to do, according to tax professionals.

“Any taxpayer that would have these issues before the IRS should be rightfully concerned,” said Joseph Opich, a tax partner at law firm Paul Hastings. “The law places strict liability on the taxpayer. You are responsible for what goes on your re

turn. There is no defense for ‘my accountant did it.’”

The revelations about Trump’s tax returns and finances unfolded just two days before the first debate between the president and Democratic nominee Joe Biden and 36 days before the election. Trump trails Biden in every recent national poll.

Trump has called the New York Times reporting “fake news” but hasn’t offered a rebuttal on the substance. In a tweet Monday he said he was “entitled, like everyone else, to depreciation & tax credits.”

Tim Murtaugh, a spokesman for Trump’s reelection campaign, said in an interview on Fox News on Monday that “the president has paid tens of millions of dollars in taxes” and the Times story is “not accurate.”

He didn’t say which parts of the story are wrong, and he didn’t specify whether Trump has paid tens of millions of dollars in income taxes. Trump’s conglomeration of businesses, the Trump Organization, has likely paid tens of millions of dollars in payroll taxes over the years.

Several things in The Times’ reporting would be “ripe for review” by the Internal

Revenue Service, Robert McKenzie, a partner at law firm Saul Ewing Arnstein & Lehr LLP, said. Paying consulting fees to employees to generate business deductions, as Trump allegedly did with his daughter Ivanka Trump, is likely to run afoul of tax rules, he said.

Plus, he said the IRS is closely watching so-called conservation easement deals, like the one Trump did with his Seven Springs estate in Westchester County, New York. That generated a $21.1 million charitable tax deduction for Trump. The location also created other tax savings because Trump reportedly treated it an investment property for tax purposes while public statements on the Trump Organization website say it was used as a family retreat.

Trump may be able to turn to some case law to defend his $70,000 worth of write-offs for hair styling for his signature look, McKenzie said. A 1994 case, Hess v. Commissioner, found that an exotic dancer could write-off the cost of exceptionally large breast implants, typically a non-deductible personal cost, because they were helpful for her job but too big to be comfortable in everyday life.

“Trump, because he’s an entertainer, may survive that,” he said.

Civil penalties generally start around 20% for negligence, but can be as high as 75% of any underpayment, plus interest if civil fraud is involved.