Helmsley died of heart failure at her summer home in Greenwich, Conn., said her publicist, Howard Rubenstein.
Already experienced in real estate before her marriage, Helmsley helped her husband Harry run a $5 billion empire that included managing the Empire State Building. She became a household name in 1989 when she was tried for tax evasion. The sensational trial included testimony from disgruntled employees who said she terrorized both the menial and the executive help at her homes and hotels.
That image of Helmsley as the “queen of mean” was sealed when a former housekeeper testified that she heard Helmsley say: “We don’t pay taxes. Only the little people pay taxes.”She denied having said it, but the words followed her for the rest of her life.
Helmsley clearly enjoyed the luxury of the couple's private fortune, flying the globe in their 100-seat jet with a bedroom suite. The couple’s residences included a nine-room penthouse with a swimming pool overlooking Central Park atop their own Park Lane Hotel; an $8 million estate in Connecticut; a condo in Palm Beach; and a mountaintop hideaway near Phoenix.
Their money supported charities, including NewYork-Presbyterian Hospital and its affiliated Weill Cornell Medical College, which received tens of millions of dollars, including a $25 million gift in 2006 to improve its treatment of digestive diseases.
Yet Helmsley nickel-and-dimed merchants on her personal purchases, stiffed contractors who worked on her Connecticut home and terrorized both menial and executive help at her homes and hotels, detractors say.
When her husband died in 1997 at age 87, Helmsley said in a statement: “My fairy tale is over. I lived a magical life with Harry.”
Earlier this year, Forbes magazine ranked her as the 369th richest person in the world, with an estimated net worth of $2.5 billion.
She was 51, with the good looks of a former model and already a successful seller of residential real estate in a hot New York market, when she married Harry Helmsley in 1972.
He was 63 and one of the richest men in America.
In 1980 he made her president of Helmsley Hotels, a subsidiary that at the time operated more than two dozen hotels in 10 states, including the Park Lane, St. Moritz and Palace in New York and the Harley Hotels. Harley was a contraction of Harry and Leona.
For the better part of a decade, a glamorous Leona Helmsley smiled out of magazine ads dressed in luxurious gowns and tiara, advertising that the Palace was the only hotel in the world “where the Queen stands guard.”
The press portrayed them as an adoring couple, with Leona calling Harry “gorgeous one” and “pussycat.” Friends and acquaintances described her as generous, charming, playful and having a good sense of humor.
She threw parties on his birthdays at which guests wore buttons that said “I’m Just Wild About Harry” and he wore a button that said “I’m Harry.” The couple would dance until dawn.
On July 4, 1976, Harry Helmsley lit the Empire State Building in red, white and blue — a tribute not to the Bicentennial, but to his wife’s birthday. It cost $100,000 — “less than a necklace,” he said.
But the Helmsleys’ charmed life ended in 1988 when they were hit with tax-evasion charges.
Harry’s health and memory were so poor that he was judged incompetent to stand trial. His wife, after an eight-week trial, was convicted of evading $1.2 million in federal taxes by billing Helmsley businesses for personal expenses ranging from her underwear to $3 million worth of renovations to the Dunellen Hall estate in Connecticut.
Sentenced to four years in prison, she tried to avoid jail by pleading that Harry might die without her at his side. Her doctor said that prison might kill her because of high blood pressure and other problems. (At a March 1992 hearing, the judge rejected that argument and even ordered her to surrender on April 15 — tax day.)
Helmsley served a total of 21 months and was released in January 1994. She had 150 hours added to her 750 hours of community service because employees had done some of the chores for her.
Several top executives at Helmsley companies said their firings coincided with her release. She maintained she couldn’t have fired them because she had given up her management post — as a convicted felon she was barred from running enterprises with liquor licenses, such as hotels. The State Liquor Authority said it had no evidence that she was still in charge.
In 1996, two longtime partners of Harry Helmsley’s accused his wife of scheming to loot the main corporation, Helmsley-Spear Inc. They said she was stripping away company assets to avoid paying $11.4 million owed them and to make the company worthless, because Harry Helmsley had given them an option to buy Helmsley-Spear at a bargain price upon his death.
After he died a few months later, the dispute with the partners was eventually settled and control of Helmsley-Spear was turned over to them. The settlement freed Leona Helmsley to sell off other assets.
The Helmsleys’ charitable gifts may have run to the tens of millions, but people who dealt with them spoke bitterly of being stiffed.
One of them, a painting contractor, said Leona Helmsley wouldn’t pay an $88,000 bill for work on Dunellen Hall because she was entitled to a “commission” for the $800,000 worth of other jobs he got in Helmsley buildings.
After making a sales clerk rewrite a bill for earrings to save $4 in sales tax, she reportedly said: “That’s how the rich get richer.” Her lawyers suggested that the government came after her to make an example of someone with high visibility.
Helmsley was born Leona Mindy Rosenthal on July 4, 1920, the daughter of a Manhattan hat maker. She left college after two years to become a model.
She married a lawyer, Leo Panzirer, whom she divorced in 1959. Their only child, Jay Panzirer, later ran a Florida-based building supplies company that did extensive business with Helmsley properties. She later was briefly married to a garment industry executive, Joe Lubin.
Before her son’s death of a heart attack in 1982, she told interviewers she would not talk about him “because terrible things can happen to people these days.”
She evidently was referring to being knifed by robbers at her Palm Beach home in 1973. She was stabbed in the chest and suffered a collapsed lung, and Harry was wounded in the arm.
After her son died, she sued the estate for money and property she said her son had borrowed, and an eviction notice was served on her son’s widow, Mimi.
Mimi Panzirer said afterward that the legal costs wiped her out and “to this day I don’t know why they did it.”
Helmsley is survived by her brother and his wife, four grandchildren and 12 great-grandchildren. Funeral arrangements have not yet been announced.
