You know, I keep seeing people talking about Trump expensing his hair care with the idea that it's a phony deduction, but here's the thing that I think we should be looking at: what other obviously personal-use goods and services were expensed?

I ask *not* on a tax angle.
As I've said many times, both before and since the NYT story dropped, Trump's MO is to live off the streams of other people's money that pass through his hands. Salaries he pays himself as manager or consultant on a project. His casinos lost money but he got paid to run them.
Here's the thing about Donald Trump constantly eating at his own restaurants. It not only appeals to his paranoia and his love of consistency, but part of the story is that he does it out of a sense of perfectionism. He's constantly testing them.
So for instance, has he been counting all of his meals as business expenses? The IRS has rules for when you can deduct a meal but apart from that has he been passing off eating in his own restaurants as part of the expense of running one?
I honestly would not be surprised to learn that he doesn't ever pay a bill for eating in his restaurants, has the cost of the meal counted as an expense for the restaurant biz, and also "expenses" the meal on his end (despite not having paid for it).
Basically... and this would honestly probably be small potatoes in terms of high finance dollars and cents... but if I were an investigative reporter going over his taxes I would be looking for evidence that his "billionaire" lifestyle is the equivalent of showering at work.
How many of his properties include posh living quarters for him? How many of the properties that he stays in have catering and personal services? These things are not weird or bad or illegal in and of themselves (but how does he pay for them, and how does he write them off)...
...but, for instance, the entire time his fabled casinos were famously losing money, he still held court there and lived like a goshdang king, didn't he?

Which is not necessarily a crime, though it may have included crimes.
It's small, small potatoes compared to being in hock to foreign oligarchs and mobsters, but a pattern of dubiously expensing personal services and goods supports the view of Donald Trump as a con artist playing a tycoon.
That $70,000 that Donald Trump deducted for hair care while he was on the Apprentice?

Who would be surprised to learn that NBC was paying for some of his hair care?
I mean, this would be classic Trump: get the network to pick up the tab for his grooming and wardrobe, then inflate the price, and claim it as a personal expense. He gets the perks and the write-off, and whatever money he can pocket along the way.
And the thing is it would take a forensic accountant cross-referencing among the literally hundreds of paper companies and shell corporations he has created, to say nothing of outside entities like TV networks and his own licensees, to catch how much double-dipping he's doing.
But it would be against Trump's nature to *not* double dip. "That makes me smart." People who don't do it are "suckers".
I mean, I say double dip, but I guarantee -- I GUARANTEE -- that he's been charging the same expenses to multiple of his companies, that he's been attributing the same losses to multiple entities, so he can count them multiple times.
Donald Trump doesn't make money. He takes money. And he doesn't particularly care if he holds onto it, so long as he gets some use out of it.
Money is an illusion, a shared dream, a way of keeping score. And just like "norms" or lines on a floor or a sign on a bowl of free candy that says "limit one per customer", he understands that other people care about it in a way that he actually doesn't.
Donald Trump was still rich when his personal net worth was negative, when his liabilities were something like negative nine hundred and eighty million dollars and his assets were so tenuous and ephemeral and obfuscated no one could say what he actually owned.
He'd like to be a billionaire but he understands in a way that few people do how little it actually matters if a person has a billion dollars if they can get a billion dollars of value out of life.
To Donald Trump, money (other peopl's money) is fuel that he burns in order to propel himself forward and keep himself warm and illuminate himself.

His casinos weren't a failure to him, they kept his lifestyle going for years and propelled him to the next big thing after them.
Other people who view money as an illusion probably laundered a lot of it through his casinos; people trying to run businesses in partnership with him were soaked and then left holding the bag.

(And his dad spent a lot of his siblings' inheritance propping the illusion up.)
As per usual, Sarah Kendzior is lightyears ahead on this. https://twitter.com/sarahkendzior/status/1310338745984581633
If the invoices show he bought $200,000 worth of grand pianos, he'll definitely report that he spent $200,000 on grand pianos. https://twitter.com/Philosopher_Dad/status/1310573683279360000
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