The life of Leona Helmsley presents an object lesson in the truism that money does not buy happiness. Born in 1920, she overcame a hardscrabble youth in Brooklyn to become a successful condominium broker in Manhattan, eventually alighting, in the nineteen-sixties, at a firm owned by Harry B. Helmsley, one of the city’s biggest real-estate developers. The two married in 1972, and Leona became the public face of their empire, the self-styled “queen” of the Helmsley chain of hotels. In a series of ads that ran in the Times Magazine and elsewhere, Helmsley’s visage became a symbol of the celebration of wealth in the nineteen-eighties. She wouldn’t settle for skimpy towels, the ads proclaimed—“Why should you?”
In private, as it turned out, the grinning monarch wasn’t just demanding but despotic. Throughout her life, Leona left a trail of ruin—embittered relatives, fired employees, and, fatefully, unpaid taxes. Knowing that the Helmsleys had used company funds to renovate their sprawling mansion, Dunnellen Hall, in Greenwich, Connecticut, disgruntled associates leaked the records to the Post. Among the charges billed to the company were a million-dollar dance floor installed above a swimming pool; a forty-five-thousand-dollar silver clock; and a two-hundred-and-ten-thousand-dollar mahogany card table. In 1988, the U.S. Attorney’s office charged the couple with income-tax evasion, among other crimes. (Harry Helmsley avoided trial because of ill health; he died in 1997, at the age of eighty-seven.) At the trial, a housekeeper famously testified that Leona had told her, “We don’t pay taxes. Only the little people pay taxes,” and the public warmed itself on a tabloid bonfire built under the Queen of Mean. Leona was convicted of multiple counts and served eighteen months in federal prison. In time, following her release, she became largely a recluse, and she died at Dunnellen Hall on August 20, 2007.
After her husband died, Leona Helmsley got a dog named Trouble, a Maltese bitch. In her will, which she signed two years before her death, Helmsley put aside twelve million dollars in a trust to care for Trouble. Further, she directed that, when Trouble died, the dog was to be “buried next to my remains in the Helmsley Mausoleum,” at Sleepy Hollow Cemetery, in Westchester County. Helmsley made only a handful of relatively small individual bequests in the will, and left the bulk of her remaining estate to the Leona M. and Harry B. Helmsley Charitable Trust. Based on the figures in court files, that trust may turn out to be worth nearly eight billion dollars, which would make it one of the top ten or so foundations in the United States. (Leona’s estate was so large because Harry left his fortune to her.) According to a “mission statement,” which Helmsley signed on March 1, 2004, the trust was to make expenditures for “purposes related to the provision of care for dogs.” The size of the bequests, to Trouble and to dogs generally, has generated widespread astonishment.
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