1989
Even more than Gordon Gekko, Leona Helmsley symbolized the “greed is good” ethos of the eighties. Her trial in 1989 for tax evasion was a delicious coda to the decade, offering up the pleasure of watching the Queen of Mean, outrageous, nasty, and entitled, be forced to swap her 10,000-square-foot Park Lane penthouse for a prison cell.
The daughter of a Brooklyn hat manufacturer, tough-talking Leona Mindy Rosenthal worked her way up from receptionist to top real-estate broker—jettisoning two husbands en route—when she caught the eye of the married older billionaire Harry Helmsley.
After marrying the unassuming Harry in 1972, she became a household name, starring in glitzy cleavage-baring ads for Helmsley hotels as the perfectionist “queen,” guaranteeing the good life for guests and willing to terrorize the staff. It wasn’t an act. Leona humiliated and fired employees at whim.
She also had an obsession with avoiding taxes. Caught up in a sting involving Van Cleef & Arpels, she received immunity for testifying that jewelry-store employees allowed her to walk out with thousands of dollars of baubles and shipped empty boxes to her out-of-town residences to save on sales tax. After she and Harry stiffed the contractors renovating their 28-room Greenwich home, disgruntled employees alerted the Post about the Helmsleys’ curious habit of charging pricey renovations (a marble dance floor, a $130,000 stereo system) to corporate accounts. Enter crusading prosecutor Rudy Giuliani.
Charged with 235 counts of tax evasion, Harry, a frail 80-year-old, was found unfit to stand trial, so Leona was left to face her employees’ revenge. The high point: housekeeper Elizabeth Baum’s recounting that Leona told her “We don’t pay taxes, only the little people pay taxes.”
Fined $7.1 million, Leona served eighteen months in prison and was freed in 1994 (her husband died in 1997). She was later sued by two employees who claimed she fired them because they were gay. She lived until 2007, leaving one last spiteful surprise in her will: disinheriting two grandchildren and leaving $12 million to her Maltese, Trouble, a biter who attacked staff. A judge slashed the bequest to $2 million. Trouble, who received death threats (requiring a $100,000 yearly security retinue), died in 2010.