The Queen of Mean

Off to jail, Leona

Leona Helmsley, the Queen of Mean

On December 12, 1989, a New York City real estate mogul was sentenced to 4 years in prison, 750 hours of community service, and a $7.1 million tax fraud fine. The tax-evader was Leona Helmsley, dubbed the Queen of Mean for her treatment of people she considered beneath her. And that took in just about everybody.

As far as taxes were concerned, Leona Helmsley had a simple philosophy which she summed up as “Only little people pay taxes.” Leona was decidedly not a little person.

Leona’s husband, Harry, was a multibillionaire, who owned billions of dollars in property, including the Helmsley Palace on New York City’s Madison Avenue. The Helmsleys owned a luxurious penthouse overlooking Central Park in addition to a lavish estate in Greenwich, Connecticut. Leona was the manager of Helmsley Palace.

Her crime consisted of a scheme that had been used by others to avoid taxes. She made purchases for the couple’s private residences and claimed them as business expenses. She could surreptitiously charge the personal expenses to the business, and then write off the expenditure as a business expense.

Reportedly, the Helmsleys would extort free furniture from suppliers and had a habit of not paying contractors. Quite a nifty scheme. Also as History.com states Leona reportedly also purchased hundreds of thousands of dollars of jewelry in New York City but insisted that empty boxes be sent to Connecticut so that she could avoid the sales tax.

If this doesn’t sound like a familiar fairly current event, then meet Mr. Trump, who was head of the Trump Organization. His company was employing a similar scheme for which its chief financial officer, Allen Weisselberg, was indicted.

Donald Trump, who felt Leona Helmsley had wronged him in a property proposal that Leona Helmsley rejected, had lots to say. As reported in an April 20, 1989, Washington Post article by Howard Kurtz, Trump referred to Hensley as a "disgrace to humanity."

"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."

Now, doesn’t that sound like the Donald Trump we all know?

Just a tidbit about Leona Helmsley from Reuters August 29, 2007: It’s worth reading. Click on the link.

Helmsley leaves $12 million for her dog

Finally Rachel Maddow had some things to say about Leona Helmsley and the schemes that the rich employ to avoid taxes. She does not directly mention the Trump Business. However, this clip is from July 2, 2021, and the Trump Organization was charged with tax evasion in June, 2021. I think there’s a logical connection.

Thanks for reading.