Leona Helmsley – 1989

By | November 12, 2016

“Only the little people pay taxes”


Real estate queen Leona Helmsley leaving court


In the 1980s the world learned of hotel magnate Leona Helmsley, who was dubbed the Queen of Mean by the press because of her ruthlessness. Helmsley was born Lena Mindy Rosenthal on 4 July 1920 at Marbletown, Ulster County, New York, the daughter of a hatter.

She worked hard to ensure that she was never poor like her father, often staying up until 3am to finish a deal when she began her career as an estate agent. By the time of her third marriage to landlord Harry Helmsley in 1972 she was the top estate agent in New York and reputedly worth $1 million. She took over the running of Harry Helmsley’s property empire, which included 27 hotels and a number of skyscrapers, including the Empire State Building. On her birthday each year her husband would decorate the iconic building in red, white and blue lights. Leona Helmsley introduced a clever marketing strategy of being a perfectionist: if she was one, then a stay at one of her hotels could be expected to be perfect also.

It was a remarkably successful plan and businessmen and the rich began to stay regularly at Helmsley hotels. If Leona Helmsley was a perfectionist, she expected her staff to be the same. Busboys, chambermaids, receptionists and even bodyguards were all terrified of her and tried their best to avoid her when she stalked the corridors looking for examples of sloppiness. The staff looked forward to the hour between 6.30am and 7.30am because they knew that was the only time she would not be on the prowl — that was the time she used the swimming pool in her penthouse at the Park Lane Hotel.

The swimming pool attendants had to keep a platter of fresh seafood at each end of the pool and as she completed a lap they had to drop a shrimp into her open mouth as she called out, “Feed the fishy.” And then it all went wrong. Helmsley was investigated by the Internal Revenue Service who discovered that she had spent $8 million on her Connecticut home and claimed it against tax. On 14 April 1988 the Helmsleys were indicted on 188 charges. They managed to have the trial delayed until 26 June of the following year. On 12 July a former housekeeper at Dunellen Hall reported Leona Helmsley as saying in 1983 (although she denied having said it), “We don’t pay taxes. Only the little people pay taxes.” On 30 August 1989 Leona Helmsley was found guilty of one count of conspiracy, three counts of tax evasion, three counts of filing false tax returns, ten counts of mail fraud and 16 counts of filing incorrect business tax returns. She was acquitted on a charge of extortion that would have led to life in prison. On 14 November she was sentenced to 16 years in prison (later reduced to four years after all but eight charges were dropped), 750 hours’ community service and fined $7.75 million. She cried when the verdict was passed.


New York City and Greenwich, Connecticut, USA


Wednesday 30 August 1989


Leona Helmsley went to a low security prison in Danbury, Connecticut where she continued to behave as the Queen of Mean. She hired inmates to make her bed and one as a secretary. Rather than fulfil her community service in the cold climate of New York, Helmsley carried her out her punishment in the warm air of Phoenix, Arizona, having persuaded the judge that her 84-year-old husband would suffer in the Big Apple cold. She served 19 months with a further two under house arrest. Leona Helmsley died of congestive heart failure on Monday 20 August 2007. She was 87.

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