Trump Took $70,000 in Tax Deductions for Hair Care. Experts Say That’s Illegal.

That appears to be roughly $1,000 an episode, on the high end but hardly unheard-of for Hollywood stars.

The Trump Corporation also paid Ms. Sinclair at least $2,500 in 2007. It’s not clear whether that had anything to do with “The Apprentice.” The grand total for 2004 to 2007: $72,243.

The tax records don’t indicate exactly what services Ms. Sinclair performed. But in the credits on numerous episodes of “The Apprentice,” Ms. Sinclair is listed as having styled Mr. Trump’s hair. She is also credited on some episodes with doing Mr. Trump’s makeup and on others with both. Ms. Sinclair’s résumé states that she has also worked for celebrities like Tina Fey, Paris Hilton and Steve Martin. Ms. Sinclair didn’t respond to a request for comment.

The federal tax code says “personal expenses” cannot be deducted.

“There’s no way he could have legitimately deducted hair expenses, whether reimbursed or not,” said Mr. Moore, the tax lawyer. “There are many cases and audits dealing with this issue.”

Indeed, some of those cases specifically deal with television personalities.

In 2011, the U.S. Tax Court heard a case involving a news anchor at the NBC affiliate in Columbus, Ohio, who deducted her hair-care expenses on the grounds that her job required it and that she was a full-time ambassador for the station. The court flatly rejected the claim. Expenses related to “grooming” are “inherently personal expenditures,” the court held, even though “these expenses may be related to her job.”

In 1980, the court issued a similar ruling in the case of a Boston-area NBC newscaster, who also happened to be a real estate investor. The court noted that his employer required him to maintain an appearance “suitable for services as a television announcer,” but didn’t reimburse him for his $10 monthly haircuts. So he deducted the costs. The court rejected the deduction.

It is not clear why Mr. Trump, who maintained the same hairstyle on set and off, would deserve different tax treatment. (Expenses for clothing are held to a similar test. The cost of costumes and uniforms may be deductible, but if they can also be worn outside the set or workplace, like with a business suit, their cost can’t be written off.)

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