The death of New York’s penny-pinching ‘Queen of Mean’

Profile of Eighties Manhattan property tycoon Leona Helmsley who famously declared during her 1989 trial for tax evasion that 'only the little people pay taxes' - and later found that the little people can bite back.

"No two billionaires loathe each other on a personal level more than The Donald and The Queen of Mean," noted Forbes of Manhattan's two most famous Eighties property tycoons, Donald Trump and Leona Helmsley. Their feuding became legendary, but it was Helmsley who gained most notoriety as the original "bully broad" so formidable that, during her 1989 trial for tax evasion, even her attorney described her as a "tough bitch". Her house-keeper's testimony sealed her reputation as the capitalist from hell. Helmsley, she told the court, believed "only the little people pay taxes".

Queen Leona came to the public eye after her 1972 marriage to Harry B. Helmsley, the "King Kong of Big Apple Real Estate", who'd risen from being a rent-collector in Hell's Kitchen during the Depression to control real estate worth $5bn, including the Empire State Building and a string of New York's finest hotels. Helmsley had been a "low-profile, behind-the-scenes kind of guy" until he ditched his wife of 38 years to marry Leona, then an ambitious estate agent, says The New York Times. "She was the one who understood that they were living in a time when wealth needed to be married to a sense of celebrity and self." Leona's real power came in 1980, when, after a series of strokes, Helmsley put her in charge of the hotel chain. "He said the best thing about it was that the board of directors meetings were over when we got out of bed," said Helmsley, who appeared in endless advertisements in a tiara and ball gown, announcing that at the Palace Hotel "the Queen stands guard". Hotel gift shops sold decks of cards with Queen Leona's picture on them and she became famous for her penchant for luxury towels. "I won't settle for skimpy towels why should you?" she asked punters.

Yet that was just the tip of her extravagance, says The Daily Telegraph. A liveried servant bearing a silver platter would be required to attend Leona's morning swims, hand-feeding her shrimps at the end of each lap, and she became famous for the lavish birthday parties she threw for her elderly husband. Yet Leona had always been a talented business­woman, says The Independent. Born Leona Mindy Rosenthal in 1920, she worked as a teenage model and then as a secretary for an estate agent before becoming a broker herself. In 1968, by now twice married and a mother of one, she was named "Man of the Week" by Real Estate Weekly. By the time she met Helmsley, she was already a millionaire.

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Ultimately, it was Leona's "unusual combination of 1980s excess and a Depression-era pathological cheapness" that sealed her fate, says The New York Times. "Her Majesty charged her underwear from Macy's along with $500,000 in jade knick-knacks and a marble floor for the pool room to the company." She also developed tax-avoidance strategies that would have seemed penny-pinching "if employed by your elderly aunt on Social Security". Her high-handed manner didn't help: she crossed virtually everyone she ever did business with. They talked to the newspapers, then the prosecutors, and the Helmsleys were charged with 235 counts of tax evasion. Harry was deemed too feeble to be tried, but Leona was convicted and spent 19 months of a 16-year sentence in jail. Subsequent attempts to rebuild her reputation never quenched the notoriety that endured until her death, aged 87, last week, as the billionaire Queen of Mean.

The little people' bite back

Given the rancour during the trial, "you'd have thought Leona had bankrupted the steel mill, thrown the whole town out of work and run off with the church poor box", says The New York Times. She felt she was the victim of a sexual double standard: "Men don't want women getting to the top. Period," she told Playboy. "There was more than a whiff of the Salem witch trials about the whole affair," agrees The Daily Telegraph. Donald Trump however felt moved to write to Harry Helmsley to tell him that his wife was "a disgrace to the human race". But was Leona really so bad?

Trump, who clashed repeatedly with the Helmsleys over the running and ownership of the Empire State Building, certainly had an axe to grind. And it could be argued, says the LA Times, that even Helmsley's legendary mistreatment of staff was down to a drive to improve customer service. "I know if a bulb is out in Room 14 before the manager does," she said. "I read every card guests fill out, especially the negative ones, and I answer them personally". But that doesn't explain her frequent vindictiveness: witnesses testified that she fired servants in fits of temper and, on hearing that an unpaid contractor needed his money because he had six children to feed, she is said to have responded: "why doesn't he keep his pants on?" In later life, she turned to philanthropy in a bid to restore her image, but ultimately proved her own worst enemy. In 2003, it was reported that two senior hotel managers were planning to sue her for wrongful dismissal: one for being gay, the other for rejecting her advances. "If there is a moral to her story, it is perhaps this", says The Guardian: "be nice to the little people, as it hurts when they bite back."