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...