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?”

Photograph from Splash News

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.

In fact, the clear motivation underlying Leona Helmsley’s will—her desire to pass her wealth on to dogs—is more common than might be expected. Pet-lovers (many of whom now prefer the term “animal companion”) have engineered a quiet revolution in the law to allow, in effect, nonhumans to inherit and spend money. It is becoming routine for dogs to receive cash and real estate in the form of trusts, and there is already at least one major foundation devoted to helping dogs. A network of lawyers and animal activists has orchestrated these changes, largely without opposition, in order to whittle down the legal distinctions between human beings and animals. They are already making plans for the Helmsleys’ billions.

For a couple that became emblematic of late-twentieth-century New York, Harry and Leona Helmsley were an unlikely pair. Harry, born in 1909 and raised in the Bronx, was sixteen when he joined a small Manhattan real-estate firm as an office boy for twelve dollars a week, and soon worked his way into a partnership. In 1938, he married the former Eve Green, a widow. Tall, stooped, a workaholic before the term was invented, Helmsley started buying buildings that were, in a way, a reflection of himself—drab but profitable. Often collaborating with a rotating group of partners on different projects, he moved on to a few more glamorous acquisitions, like the Empire State Building, in 1961, but he seemed to go out of his way to avoid calling attention to himself. He and Eve had no children. “My properties are my children,” he would say.

Lena Rosenthal, in contrast, was a raucous, disputatious presence seemingly from birth. (She later changed her name to Leona Roberts.) Nearly every aspect of her biography has been challenged, particularly if she was the source for it. She claimed to have worked as a model for Chesterfield cigarettes in her early years, but evidence for that assertion is elusive. She was married three times, but generally acknowledged having had only two husbands. She married Leo Panzirer in 1940, and they divorced twelve years later. Then she married and divorced Joseph Lubin (she usually neglected to mention him at all in later years), before her marriage to Harry Helmsley, who had left his wife of thirty-three years shortly after Leona’s arrival at his firm. Leona had one child, Jay Panzirer, who died, of a heart ailment, in 1982, at the age of forty. Jay Panzirer had four children, and these grandchildren survived Leona. The will hints at the tense relationship between her and her only descendants.

Leona had contentious relationships with almost everybody (except Harry). In particular, she came to despise Jay’s widow, Mimi, his third wife, for reasons that Mimi later said she never understood. Following Jay’s death, the Helmsleys moved immediately to evict Mimi and their eldest grandchild, Craig, from their home in Florida, which was owned by a Helmsley subsidiary. During the next several years, the Helmsleys filed no fewer than six lawsuits against Mimi, asserting that they were entitled to the money in Jay’s estate, a distinctly modest sum compared with their own fortune. After five years of rancorous litigation, Leona won about two-thirds of the two hundred and thirty-one thousand dollars at issue. As a result of Leona’s legal triumph, each of her grandchildren was left with an inheritance from their father of a little more than four hundred dollars.

In her will, Leona Helmsley was more generous to two of her grandchildren, David and Walter Panzirer, who were left trusts and bequests worth ten million dollars, on the condition that they visit their father’s grave at least once a year. (Jay was buried in the family mausoleum, alongside Harry and Leona.) To make sure that they did, the will stipulated that the trustees “shall have placed in the Helmsley Mausoleum a register to be signed by each visitor.” Leona’s other two grandchildren, Craig Panzirer and Meegan Panzirer Wesolko, were excluded from any inheritance, “for reasons which are known to them.” (The reasons were not disclosed.) That omission led to the first legal skirmish regarding the Helmsley estate. Lawyers for the two disinherited grandchildren filed a notice in Manhattan Surrogate’s Court announcing that they planned to challenge the will on the ground that Leona “was not of sound mind or memory and did not have the mental capacity to make a Will” in 2005.

Leona’s executors—her surviving brother, Alvin Rosenthal; her grandsons David and Walter Panzirer; her lawyer Sandor Frankel; and John Codey, a family friend—decided to settle the dispute quickly. They agreed to amend the will so that Craig and Meegan also received bequests: four million dollars for Craig, and two million for Meegan. In return, Craig and Meegan agreed to an elaborate confidentiality provision, promising not to “directly or indirectly publish or cause to be published any diary, memoir, letter, story, photograph, interview, article, essay, account or depiction of any kind” concerning the dispute over the will. Likewise, they agreed that all of their “personal correspondence . . . records, tapes, papers and financial information of or relating to” Leona must be given to the estate’s lawyers. (Consequently, neither Craig nor Meegan, nor their attorneys, would comment on the dispute.) Still, the conflict among the human beneficiaries of the will was easy to resolve compared with the legal matters relating to dogs.

The modern history of legal rights for animals begins with a chimpanzee named Washoe. “He was the first ‘signing chimp,’ the first chimpanzee who learned sign language to communicate with people,” Victoria Bjorklund, the head of the exempt-organizations practice at the New York law firm of Simpson Thacher & Bartlett, said. “There came a time when he was going to be sent off to be used in medical testing, and there was a lot of distress about that possibility.” So Bjorklund and others set up a trust (funded with the proceeds of a book about Washoe), and appointed a guardian to protect him and several other chimps like him. The problem was that New York law said that a guardian could be appointed for a “person with a disability.” Was Washoe a “person” under New York law?

The lawyers at Simpson Thacher argued that “the mental, emotional, sociological, and biological characteristics” of Washoe and the other chimps “warrant their treatment as persons” entitled to representation. The lawyers submitted affidavits from such animal experts as Jane Goodall, who said that “chimpanzees are biochemically closer to humans than they are to any other of the great apes.” According to the brief in the case, the chimps “are capable of rational thought, communication, and other higher cognitive functions,” justifying their treatment as the legal equivalent of minors or disabled humans. In a 1997 decision, the surrogate of Nassau County agreed and appointed a guardian to administer the trust for the benefit of the chimps. “That trust was then respected by the State of Washington, where Washoe lived,” Bjorklund said. “We think it was the first trust ever established for the benefit of specific nonhuman primates.”

Jane Hoffman, a former associate at Simpson Thacher, had brought the Washoe case to the firm. “The idea was to create a right for a nonhuman animal to receive money—to push the envelope on the law, which at that point had only allowed trusts for the benefit of children or disabled adults,” she said. In 1990, Hoffman and a group of other lawyers founded a new committee at the Association of the Bar of the City of New York, on “Legal Issues Pertaining to Animals.” One of the first subjects that the committee’s members took up was the issue of inheritance. In 1996, they helped change the law to make it easier for any animal—especially a pet—to become the beneficiary of a trust. Many people wanted to make provisions for the care of their pets in their wills, but the law allowed no simple mechanism to do so. Frances Carlisle, a New York trusts-and-estates lawyer and a member of the committee, pushed the New York State Legislature to allow the creation of “pet trusts,” which permit individuals to put aside money and instructions for their pets. New York approved the changes, and now thirty-eight states allow for the creation of such trusts. “We decided we didn’t want people to have to leave the disposition of their pets to chance, or a sudden decision, after they died,” Carlisle told me. “We want to give people peace of mind about their animals.”

The legal movement, which largely focussed on pets, was, of course, symbiotically aligned with the broader animal-rights movement, which also grew in the nineteen-nineties. But the theme remained the same—to extend the rights of humans to animals. In a country where most people eat meat, many hunt, and most others give little thought to the legal rights of their pets, the complexities of such a change are considerable. Even pro-animal-rights scholars, like Peter Singer, a professor at Princeton, recognize the difficulties. As Singer said at a recent conference in New York City, “We’re talking about beings as different as chimpanzees, pigs, chickens, fish, oysters, and others, and you must recognize those differences.” For the moment, the goals of the movement are modest, and largely limited to domestic animals.

“What the law is doing is catching up with the idea that people don’t consider their pets property, in the way a car or a chair is,” Hoffman told me. “I am not pumping for my cats to be able to vote for McCain or Obama. I’m not saying they could visit me at the hospital, though that’s probably a pretty good idea. The right category for pets is closer to children, who can’t vote, and can’t own property, but you can’t inflict pain on them, either. The law is catching up with societal beliefs.”

“Leona had never had a dog before she got Trouble,” Elaine Silverstein, a co-founder of the Miami agency that created the “queen” advertisements for the Helmsley hotels, told me. “She treated her like a person, and took her everywhere. She would take that dog to bed with her every night.” After Helmsley’s release from prison, she returned for a time to her hotels’ ads, but for one campaign she insisted that Silverstein feature Trouble instead. The ad showed the tiny white dog perched on a red velvet chair, and text that said, “ ‘Trouble,’ the Helmsley’s favorite four-legged guest,” recommends that you call for reservations. “It didn’t make much sense for a dog to endorse a hotel, but that’s what Leona wanted,” Silverstein said.

Still, Helmsley’s relationship with dogs reflected some of the distemper of her dealings with humans. According to Silverstein, one of Helmsley’s friends, seeing how much she loved Trouble, gave her another Maltese, who was named Double Trouble. “But Leona never liked that dog, so she got rid of it,” Silverstein said. “That was usually Leona’s solution. It was what she did with people.”

For all Helmsley’s love of Trouble, her will certainly made life complicated for the dog. She stipulated that Trouble, when her time came, join Leona, Harry, and Jay in the family mausoleum. (Leona also established a three-million-dollar trust for the “perpetual care and maintenance” of the mausoleum, directing that it be “acid washed or steam cleaned at least once a year.”) According to Carlisle, however, a joint human-canine burial is not possible at Sleepy Hollow. “Under New York law, animals can’t be buried in human cemeteries,” she said. “Leona could possibly be buried in a pet cemetery with Trouble, but not the other way around. That was an error in the drafting of the will.” (Trouble is still alive, so it’s not clear where she will be buried.)

The twelve-million-dollar trust for Trouble also created problems. The will stated that custody of Trouble should go to Rosenthal, Leona’s brother, or to her grandson David, and the trust agreement directed them to “provide for the care, welfare and comfort of Trouble at the highest standard.” But neither man wanted the dog. After the will was made public, Trouble received death threats, which may have had something to do with their refusal. (Both men declined to comment.) So the trustees had to find the dog a home. Moreover, the bequest to Trouble was so self-evidently excessive for a single, aging dog that the trustees decided to take steps to reduce it.

As a guardian for Trouble, the trustees settled on Carl Lekic, who is the general manager of the Helmsley Sandcastle Hotel, in Sarasota, Florida. According to his affidavit in the case, Lekic had known Trouble since she was born, because Leona spent several months a year, late in life, at the hotel. “When I visited New York on business while Mrs. Helmsley was alive, I would also see Trouble and would pay attention to and play with her,” Lekic said. The trustees agreed to pay him five thousand dollars a month to take care of Trouble. Lekic estimated annual security costs for the dog of a hundred thousand dollars, grooming costs of eight thousand dollars, food costs of twelve hundred dollars, and veterinary care of up to eighteen thousand dollars.

But how many years would Trouble likely live? To answer this question, the trustees sought an affidavit from Dr. E. F. Thomas, Jr., Trouble’s veterinarian. Trouble was nine years old in early 2008 and had, according to Thomas, “several ongoing medical problems,” including hypothyroidism and compromised kidney function. In the light of her medical issues, and the patterns of Maltese generally, Thomas estimated that Trouble was likely to live only three to five more years. In all, then, Lekic and the trustees concluded, only two million dollars of the trust’s principal would suffice to cover all of Trouble’s needs. On April 30, 2008, Judge Renee Roth, the New York surrogate who is supervising the Helmsley will, approved the reduction of ten million dollars in the trust. (If there is any leftover money in Trouble’s trust following her demise, it goes to the Helmsley charitable trust.)