Nicknamed "the Queen of Mean," Leona Helmsley (born 1920) managed several swank New York City hotels with her billionaire husband Harry Hemsley. She was thoroughly disliked for her harsh treatment of employees, which was legend. Lawyer Alan Dershowitz said he once had breakfast with Leona at one of the Hemsley hotels and the waiter brought him a cup of tea with a tiny bit of water spilled on the saucer. Alan says Leona grabbed the cup from him and smashed it on the floor, then demanded that the waiter get down on his hands and knees and beg for his job.
Leona got her comeuppance when in 1989 she was convicted on federal charges of tax evasion in a celebrated trial. Harry had been indicted along with Leona, but it was determined that he was far too ill physically to stand trial and too weak mentally to be capable of assisting his attorneys in his own defense. That left Leona to stand alone but her conduct during the ensuing trial did little to endear her to anyone, and when she was quoted as saying "only the little people pay taxes," she became the New Yorker everyone loved to hate. But despite her wealth she wasn't above the law, and was sentenced to four years of jail, 750 hours of community service, and fines of $7.1 million.
Harry B. Hemsley (1909 - 1997) was a real estate mogul who built a company that became one of the largest property holders in the United States. Part of his portfolio at one time included the Empire State Building (above), The Helmsley Palace, The Park Lane Hotel, The Hemsley Middletown Hotel, The New York Hemsley Hotel (aka The New York Harley), The Hemsley Windsor Hotel, The St. Moritz (now Ritz Carlton), The Carlton House hotels, the Harley Hotel chain and The Helmsley Building in NYC.
, Mrs Hemsley served 18 months in federal prison. Her later years were apparently spent in isolation, especially after Harry died in 1997, leaving his wife his entire fortune estimated to be worth well in excess of $5 billion. She was virtually friendless and according to a Chicago Sun-Times article in 2001, was estranged from her family, and living alone in a lavish apartment with her dog.
She was forced to give up control of her hotel empire since New York does not allow convicted felons to have alcohol licenses. Leona Hemsley lived her final year alone, at her luxurious penthouse atop the Park Lane Hotel, with magnificent views across Central Park.