Dubbed the “Queen of Mean,” the tyrannical Leona Helmsley headed off to Federal prison on, ironically, the last day of tax reckoning, this week on April 15, 1992.

Mrs. Helmsley was a successful real estate broker and billionaire hotelier. Her belief that “We don’t pay taxes. Only little people pay taxes,” sealed her fate and image - when on trial for federal income tax evasion charges.

Helmsley’s shrewd personality was probably responsible for her success - and downfall. When she and her third husband Harry, purchased a Greenwich, Conn., mansion for $11 million in 1983 they balked at paying the $8 million renovation costs ... forcing contractors on the job to go to court to get paid. The legal proceedings uncovered documents that the Helmsleys had illegally invoiced the renovation costs as business expenses. Angered, the contractors sent copies of these bills to the New York Post – the resulting story prompting a federal criminal investigation and a memorable indictment by U.S. Attorney Rudy Giuliani. Helmsley’s conviction led to an 18-month prison term.

Not quite as headline grabbing as her bons mots, were her generous charitable contributions, including $5 million to help NYC firefighters post-9/11, $25 million to the New York Presbyterian Hospital and $4 billion to the Leona M. and Harry B. Helmsley Charitable Trust. Leaving a $12 million trust fund for her beloved Maltese, Trouble, however, did endear Mrs. Helmsley to many dog lovers and managed to be the lead story on the evening news.

news@doubledownmedia.com

4/14/08