The Queen of Mean Tax Evasion Story

Posted on May 15, 2022










The Queen of Mean was a famous American businesswoman whose name was Leona Helmsley. She was called the Queen of Mean by the press due to her reputation for tyrannical behavior and her glitzy personality.

But there’s more to her than that, as she is also famous for her spectacular tax evasion saga. Let’s take a look at how it all happened.

Who is Leona Helmsley?

Leona Helmsley was a billionaire, but not any type of billionaire because, at her heyday, she was as big as Kim Kardashian or Donald Trump (minus his presidency.)

Her Queen of Mean persona was fully developed during her trial for tax evasion when at one point she said: ‘‘We don’t pay taxes. Only the little people pay taxes.’’

You can imagine that that didn’t bring her much love among the people, nor the jury.

By the way, she was as terrible as her husband – tycoon Harry Helmsley – and the ‘we’ in her statement signified her and him.

The Queen of Mean Ways

Leona was already abundant, but she became a billionaire when she married Harry Helmsley who led a real estate empire. They married right after he divorced his first wife of over 30 years.

The marriage saved her riches and started bringing her even more money. She quickly became known for her stingy behavior, at least when it comes to taxes as she led a genuinely extravagant lifestyle. But when it comes to taxes, she was known to make sure she saves even a couple of dollars – which is undoubtedly ridiculous if you’re a billionaire.

The Queen’s Ruin

Her downfall commenced when she bought an $11 million mansion. She quickly started lavish renovations, but she was frustrated at their slow pace.

If she knew what her behavior would bring her, she might have taken a different course.

After her many harassments, it didn’t take long for the contractors to file a lawsuit against the Helmsley’s in which they claimed that the couple charged the work they did as a business expense. The two billionaires tried to lower their tax bills but the case brought the attention of the IRS, and when you try to put some personal expenses as business expenses to cut on taxes, the IRS will not look kindly on you.

The husband avoided the trial in the end as he was judged mentally and physically unfit for a trial, but the wife wasn’t. The court ended up indicting her on several tax-related charges. Three of her allegations were for tax evasion. She was, to her luck, acquitted for extortion; a conviction could have landed her life in prison.

She ended up in prison for a time but eventually was released. She still had her husband’s entire fortune, but she couldn’t utilize any of it as a former convict. She spent the remainder of her years in her penthouse in isolation as her husband died in 1997. She died in 2007.

Leona started spending her money on charities after she got out of prison, which means that the Queen of Mean might have changed after everything she has endured.

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