Updated:
Original:
Year
1989
Month Day
December 12

The Queen of Mean is sentenced to the slammer

Leona Helmsley, nicknamed the “Queen of Mean” by the press, receives a four-year prison sentence, 750 hours of community service, and a $7.1 million tax fraud fine in New York. For many, Helmsley became the object of loathing and disgust when she quipped that “only the little people pay taxes.”

Leona’s husband, Harry, was one of the world’s wealthiest real estate moguls, with an estimated $5 billion to $10 billion in property holdings. The couple lived in a dazzling penthouse overlooking Central Park and also maintained an impressive mansion in Greenwich, Connecticut. Leona, who operated the Helmsley Palace on Madison Avenue, was severely disliked by her employees.

Though they lavishly furnished their homes and hotel, the Helmsleys were curiously diligent about evading the required payments and taxes for their purchases. Much of their personal furniture was written off as a business expense, and there were claims that the Helmsleys extorted free furnishings from their suppliers. Contractors were hardly ever paid on time-if at all-and many filed lawsuits to recover even just a portion of what they were owed. 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.

Given her offensive personality, many were quite pleased by Leona’s legal troubles. Even celebrity lawyer Alan Dershowitz could not win her immunity from the law. Following her conviction, Federal Judge John Walker publicly reprimanded her, saying, “Your conduct was the product of naked greed [and] the arrogant belief that you were above the law.” Leona Helmsley was sent to jail in 1992 and was released in 1994. In 2002, Helmsley, whose husband Harry died in 1997, again found herself in court after being sued by Charles Bell, a former employee who accused Leona of firing him soley because he was homosexual. A jury ordered Helmsley to pay him more than $11 million in damages.

Helmsley died in August 2007 at age 87. She famously left $12 million to her dog, Trouble.

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