“Barbara Walters Presents”: “Queen of Mean” Leona Helmsley

Leona Helmsley's mug shot [U.S. Marshals Service]

Who was the woman Donald Trump once called “a disgrace to humanity?”

Leona Helmsley, New York real estate tycoon, was often called “Queen of the Palace” after the advertisements that showcased her high standards for her Palace Hotel that she owned with husband Harry Helmsley. But she was also known as the “Queen of Mean” for her treatment of anyone she deemed beneath her … which was basically everyone.

Did her wealth allow her to cut corners and evade serious consequences? Or was her wealth the target on her back that caused her to be indicted for tax fraud in the first place?

The Rise of Leona Helmsley

Leona Mindy Rosenthal was a millionaire in her own right when she met billionaire Harry Helmsley, a fellow real estate mogul whose holdings included the Empire State Building. Despite the fact that he had been married for 33 years, Leona said that was it was love at first sight. Helmsley divorced his first wife in 1971 and the next year, he and Leona married.

(AP Photo/Suzanne Vlamis)

Leona Helmsley, president of the Helmsley Hotel chain, and her husband, real estate mogul Harry B. Helmsley, are seen at the Helmsley Palace Hotel in New York, on May 17, 1984. [AP Photo/Suzanne Vlamis]

In 1980, Leona was appointed president of Helmsley hotels, including 30 hotels around the country and four luxury hotels in New York, including the Helmsley Palace. It wasn’t long after that she began to be featured in full-page advertisements in which she was portrayed as the queen presiding over her own hotels.

The Tax Evasion

The Helmsleys bought a Connecticut mansion for $11 million that they considered a “fixer upper,” since it lacked the marble dance floor and stereo system they desired. The Helmsleys would hire contractors, not pay them, and charge expenses to their corporate accounts. Finally, an anonymous tipster contacted Ransdell Pierson with the New York Post with documentation of false invoices and other evidence of crooked bookkeeping.

Rudolph Giuliani, then a U.S. Attorney known for prosecuting high-profile defendants under fraud and tax charges, took interest in the New York Post story. When interviewed recently by Barbara Walters about the investigation that led to an indictment of the Helmsleys, he marveled at how easy it was to get people to testify against her in particular. “The hatred was enormous,” he said. “I mean, she must have treated people horribly.”

The Decline of Leona Helmsley

For her part, Leona Helmsley blamed Giuliani’s zealotry and the media attention for her conviction. “I can’t believe that we are — that this is not America,” she said in a 1992 interview with Barbara Walters. “There is no crime. Where is the crime except that I’m Leona Helmsley?”

Due to his failing health, Harry Helmsley had been deemed unfit to stand trial, and so it was only Leona who was eventually convicted of 33 counts of tax evasion and sentenced to four years in prison. One of her biggest defenses during the trial had been her willingness to pay the money back, alleging that the $4 million owed was a drop in the bucket compared to the $600 million she and her husband had paid in taxes.

But the allegations against Leona’s personality would prove as damning as those against her finances. A housekeeper testified that her boss would say, “Only the little people pay taxes.”

Leona Helmsley [AP Photo/ Louis Lanzano, File]

Leona Helmsley [AP Photo/ Louis Lanzano, File]

Once in prison, Leona reportedly hired fellow inmates to make her bed and sort her laundry, and tried to mimic the experience of staying at one of her famous hotels as best she could. She served 18 months in a limited-security federal prison, and then two more months under house arrest at one of her hotels.

In 1997, Harry Helmsley died, with Leona following a decade later. Her death made big headlines as she left more money to her pet Maltese, Trouble, than to her grandchildren. For the last years of the dog’s life, part of that money went toward security to protect the dog against death threats. The majority of the Helmsley fortune was left to charitable trusts and foundations, although Leona did earmark $3 million for the care of the mausoleum where she and her husband were buried.

Even after death, Leona Helmsley would be known for the high standards that had once dubbed her “Queen of the Palace.”

Watch new episodes of Barbara Walters Presents Tuesday at 8/7c on Investigation Discovery and with ID Go.

Read More:

The Washington Post

The New York Times

The Telegraph

New York magazine

Forbes

Biography.com

Main photo: Leona Helmsley’s mug shot [U.S. Marshals Service]