Leona Helmsley

Leona Helmsley began her career in real estate, rising from brokerage work to executive positions before meeting Harry Helmsley in the late 1960s. After Harry dumped his wife of 30+ years Leona married him in 1972. Having lost a major lawsuit that caused financial devastation and the loss of her real estate license, she took an increasingly important role in managing the Helmsley hotel empire. She became president of a chain of more than 20 hotels and gained a reputation as a highly demanding manager who closely supervised operations and marketing. As a couple, Harry and Leona expanded their holdings beyond office buildings into luxury hotels. Their empire included the Helmsley Palace Hotel, the Park Lane Hotel, and numerous other hotels across the United States. Their combined holdings were estimated in the billions of dollars. The Helmsleys' careers were overshadowed by a major tax-fraud scandal in the late 1980s. Investigators alleged that personal expenses related to their luxury residences had been improperly charged to business entities (that and she also refused to pay vendors for their labor). Harry was considered too ill to stand trial, but Leona was convicted in 1989 on multiple counts including tax evasion and filing false tax returns. She served about 19 months in prison after her sentence was reduced on appeal. She died alone at her mansion, Dunnellen Hall, at the age of 87. She was laid to rest at Sleep Hollow Cemetery in Sleepy Hollow, NY.