Once upon in New York there was a politically ambitious federal prosecutor who sent a real estate and hotel magnate to jail for tax fraud.

The charges that Rudy Giuliani,  the U.S. Attorney for the Southern District of New York, filed in 1988 against “Queen of Mean” Leona Helmsley were quite similar to the state charges brought by Manhattan District Attorney Cyrus Vance Jr. against the Trump Organization and its CFO Allen Weisselberg.

And what did Donald Trump do at the time? He threw Leona Helmsley an anvil as Helmsley was going under on the tax charges. Trump didn’t see any problem back then  with the tax fraud charges because they were brought against a business rival and a woman whom he had been feuding with for years.

Here’s a Tweet from former Republican Rep. Barbara Comstock, a Trump critic:


Leona and her husband Harry Helmsley were charged with income-tax evasion and fraud for using millions of dollars in company funds to renovate their Connecticut mansion.

Here’s Rachel Maddow’s take on the Leona Helmsley case:

A judge decided that Harry Helmsley, then 80,  was unable to stand trial because of poor health and a declining memory. Leona Helmsley was convicted in 1989 of evading $1.2 million in taxes and ended up serving 18 months in prison. Her unsuccessful appeal was handled by Alan Dershowitz.

During the trial, a housekeeper at the Helmsleys’ estate claimed she overheard Leona saying, “We don’t pay taxes. Only the little people pay taxes.”

That echoes the sentiment Donald Trump expressed in a 2016 debate with Democratic nominee Hillary Clinton. When Clinton suggested that maybe Trump doesn’t pay any income tax, Trump interjected “That makes me smart.”

 Weisselberg was accused of avoiding taxes on $1.7  million worth of indirect employee compensation from the Trump Organization that included rent for his apartment, private school payments for his family and luxury car leases.

After the indictments were announced, Trump told ABC News that the criminal charges were a “disgrace” and “shameful.”

The Trump Organization put out this statement: “Allen Weisselberg is a loving and devoted husband, father and grandfather who has worked at the Trump Organization for 48 years. … The District Attorney is bringing a criminal prosecution involving employee benefits that neither the IRS nor any other District Attorney would ever think of bringing. This is not justice; this is politics.”

And Eric Trump went on Fox News to say:  “They subpoenaed 3.5 million documents. 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 that it “isn’t a criminal matter” and said New York State “is worse than a banana republic” for trying to take down a political opponent.

So let’s flashback to 1989 when the “Queen of Mean” was about to go on trial for the tax evasion charges.

Trump had been feuding with Leona Helmsley for years. Trump was the upstart developer from Queens who was trying to break into the Manhattan real estate market. He was jealous of  the Helmsley Organization whose real estate empire included the Empire State Building.

And Leona was prominently featured in an ad campaign as the demanding “Queen of the Palace” who wouldn’t tolerate the slightest mistake.

In 1989, Trump and Helmsley were locked in a dispute over an Atlantic City property that Trump had purchased and planned to turn into a non-casino hotel. The property included a small parcel owned by the Helmsleys who refused to transfer the lease to Trump.

Trump sent a venomous misogynistic letter to Leona, as reported in The Washington Post at the time. He wrote:

“Without the veil of Harry Helmsley, you would be a non-entity. You would not be able to randomly fire and abuse people in order to make yourself happy. …

“What has happened to the legendary Helmsley reputation is indeed sad — but I am not surprised because I know you so well. When God created Leona, the world received no favors.”

“Over the last number of years,” Trump wrote, “I have watched as you have virtually destroyed my friend and a once-great and respected man, Harry Helmsley. Almost no one knows Leona Helmsley better than Donald Trump, but when the press (and others) would ask about you, I would always try to speak of your few (in my opinion) normal or positive traits … I am holding back no longer.”

To add insult to injury, Trump also penned a letter to Harry Helmsley, who was in poor health.

Trump wrote: 

“Dear Harry. You are a great man who has been badly tarnished by, in my opinion, the actions of Leona. I am enclosing a letter that I sent to Leona … Regardless of what happens, I will always respect you and be your friend.”

Both letters somehow made their way to the New York Post, which published them.

And when Helmsley’s tax fraud trial began, Trump gloated: “I can feel sorry for my worst enemy, but I cannot feel sorry for Leona Helmsley. She deserves whatever she gets.”

And the same goes for Donald Trump. He deserves whatever he gets.

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This is a Creative Commons article. The original version of this article appeared here.


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