When I was beginning my career as a tax professional in New York, Leona Helmsley, otherwise known as “the queen of mean,” (who does that remind you of?) was on trial for tax evasion. The government was out to make an example of her. More typically an audit would conclude in a financial settlement, or judgment, and you have to pay maybe a lot of money. But, like Al Capone, they wanted to put her away.
She and her Husband, Harry Helmsley, who was dead by this time, owned the Empire State Building.
The firm I worked for was part of the defense team. Technically, I don’t think that was public, but they were working for the lawyers. I had friends on the engagement. But she still lost.
All I remember is that she deducted everything as a business expense, personal furniture, stuff like that. Just like, it appears, Donald Trump.
The New York Times’ in depth analysis of his tax returns impressed me in the way that reporting of tax issues usually doesn’t. And one revelation regards a property in Westchester County that he lists as an investment on his tax return, which allows him to deduct such business expenses as would be limited or not deductible if it were considered a personal residence.
But, in 2014 Eric Trump told Forbes that he and his brother spent many summers at that property, and at one point took up residence. “It was home base for us for a long, long time,” he said.
And the Trump Organization website describes it as “a retreat for the Trump family.” So, are they treating a personal residence as a business? Like Leona?
Even his businesses seem like hobbies, so maybe he gets confused. Is he even trying to make money? I’m sure he could if he wanted to.
Other things about Leona Helmsley that remind me of Donald Trump:
She stiffed contractors. From her Wikipedia page, “After allegations of non-payment were made by contractors hired to improve Helmsley’s Connecticut home……”
And she famously said, “We don’t pay taxes; only the little people pay taxes,” just as Trump bragged that not paying taxes, “makes me smart.”
The good news is that he has a lot of debt coming due, and not a lot of cash or stock on hand that he can still sell to pay it.
I would like him to go the way of Leona Helmsley (jail). But I’ll settle for destitution.
Andy Glasser 
My first thought, when I heard of Trump’s non payment of taxes over the past many years, was, “Isn’t that how they finally put Al Capone behind bars?” Not being American, I was not cognizant of the Helmsley case (even though the name Leona Helmsley is known to me). I would like to see justice done, but I have little hope that it will happen. Good luck.
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