Born 1920

Nicknamed “the Queen of Mean,” Leona Helmsley managed several swank New York hotels with her billionaire husband Harry Helmsley (who at one point owned the Empire State Building). She was thoroughly disliked for her harsh treatment of employees even before she was indicted for tax evasion in 1988. 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 Judge John M. Walker sentenced her to four years of jail, 750 hours of community service, and fines of $7.1 million.