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Analysis | What Trump said about Leona Helmsley's tax evasion - The Washington Post

“They subpoenaed 3.5 million documents,” Eric Trump said. “They’ve gone through every single tax record that my father has had since 2005, and this is what they have: They have a company car, they have employment perks. Give me a break. They have been on a witch hunt.”

He added: “This is what they’re going after. This isn’t a criminal matter.”

The first thing to note is that these are the first charges. There might not be any others — and some analysts indeed said they were underwhelmed by the charges, to the point where they suggest the former president himself is likely safe — but we don’t yet know that. The second is that this isn’t just about providing “perks”; it’s about whether those perks were given in ways that deliberately avoided taxation. And prosecutors claim very solid evidence of that, judging by the indictment.

Something else many noted Thursday, though, was that defenses like Eric Trump’s struck quite a different tone from the one his father did three decades ago, when a high-profile rival was accused of — you guessed it — tax evasion.

[Trump’s] reluctance to discuss the allegations in depth stood in contrast to his gloating after a real estate rival, Leona Helmsley, was charged with tax crimes in 1989, prompting Mr. Trump to call her a “disgrace to humanity.”

Former Republican congresswoman Barbara Comstock (Va.), a Trump critic, added: “Trump called Leona Helmsley ‘a disgrace to humanity’ for her tax dodging….”

Trump added in that 1989 letter: “What has happened to the legendary Helmsley reputation is indeed sad — but I am not surprised. … When God created Leona, the world received no favors.”

Trump is certainly no stranger to setting a standard for someone else and then bulldozing past it himself. But how much do his comments about Helmsley actually apply to his own situation and that of his business?

That’s less clear than some suggest. While Trump certainly criticized his rival in light of her tax charges, his argument seemed to have less to do with her allegedly defrauding the government, and more to do, perhaps unsurprisingly, with her having wronged Trump personally.

The letter to Leona (more juicy excerpts in a moment) stems from (surprise) a financial dispute. To wit, casino magnate and multibillionaire developer Trump recently purchased a chunk of Atlantic City real estate from Penthouse International Ltd. for $56 million, and plans to convert an unfinished casino into a non-casino hotel. Included in the property is a small parcel owned by the Helmsleys that had been leased to Penthouse for 100 years. Trump charges that Leona Helmsley has refused to transfer the lease to him, in what should be a routine transaction, out of sheer animosity. “I’m taking her to court,” Trump said in a telephone interview today from Atlantic City. “In the real estate business you don’t do that … The woman is a total disgrace to the industry and humanity. This is a bad woman.”

When Helmsley’s tax fraud trial began, Trump again piled on, saying, “I can feel sorry for my worst enemy, but I cannot feel sorry for Leona Helmsley. She deserves whatever she gets.”

One could certainly argue that bears some relevance to the younger Trump’s complaint about alleged political targeting. The elder Trump seemed to revel in whatever punishment befell Helmsley in her tax fraud case because he didn’t like her. Now the Trump family is complaining that others are targeting them because of ill will.

As for how analogous the two cases themselves are, that’s again up for debate. But they aren’t too far apart in certain respects.

Helmsley was convicted on 33 of 41 counts, while Weisselberg and the Trump Organization face 15. But the charges were similar. For Helmsley, it was:

  • 1 count of conspiracy to defraud the United States
  • 3 counts of tax evasion
  • 3 counts of filing false personal tax returns
  • 16 counts assisting in filing false reports
  • 10 counts of mail fraud

The charges in Weisselberg’s case:

  • 1 count of conspiracy
  • 1 count of a scheme to defraud
  • 1 count of grand larceny
  • 4 counts of criminal tax fraud
  • 4 counts of filing false reports
  • 4 counts of falsifying business records

In the years since Helmsley’s trial, Trump, of course, has made no secret of his preference for conveniently getting around tax laws. During a 2016 presidential debate, he responded to Hillary Clinton’s attacks on his alleged avoidance of paying taxes by saying that, if he did so, that “makes me smart.” (We have since learned that Trump did indeed avoid paying much of any taxes for many years.) Real estate developers are known for their gaming of the tax system, so it’s hardly a surprise that Trump would avoid directly deriding specific tax-avoidance tactics.

But perhaps the most relevant Trump comment about Helmsley came in 2007, after she died.

Trump went on TV to lament what she had done to her husband Harry Helmsley, whom Trump counted as a friend, because of her tax fraud.

“And, you know, in all fairness to her, she really made him happy,” Trump said, “except for the last two years of his life, where he was going through all of this hell because of things that she caused with her tax evasion and various other — which was so foolish, because he was such a rich man.”

Indeed, even if the charges against the Trump Organization aren’t as big as some might have expected, the schemes outlined certainly lead to similar questions about why the Trump Organization would engage in them. And according to prosecutors, they all began around the time Trump lamented how “foolish” it was for Helmsley to jeopardize her family for such pittances.

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