Business executive. Born Leona Mindy Rosenthal, on July 4, 1920, in New York City. After working as a model for a number of years, she took a job as a receptionist at the New York real estate firm of Pease & Elliman. Helmsley quickly rose through the ranks and eventually established her own thriving real estate firm. In 1970, she began working for real estate mogul Harry Helmsley, whom she married in 1972.

In 1980, Leona Helmsley was named president of Helmsley Hotels, Inc. Although her real estate empire prospered, she was repeatedly chastised by the press. Often portrayed as a ruthless and despotic businesswoman, Helmsley became known as the “The Queen of Mean.”

In 1983, real estate tycoons and hoteliers Harry and Leona Helmsley bought the weekend retreat of their dreams. The newly acquired 21 room estate, known as Dunnellen Hall, was situated on 26 sprawling acres in  Greenwich , Connecticut . The cost of the enormous house and surrounding property was a staggering $11 million.

Although the property was beautiful by most standards, the Helmsleys decided that they wanted to make changes and a lot of them. Several years of remodeling and redecoration went into the house, totaling some $8 million dollars. It was an outrageous sum of money they were reluctant to pay, despite the fact that they were worth well over a billion dollars. They were even more hesitant to shell out the taxes due on the extra expenditures. Instead of paying up, the Helmsleys chose to take an illegal route. Greed would eventually get the better of them.

During and following the work on the house, a group of contractors, including decorators, gardeners, painters and landscapers, attempted to collect on the money owed to them for their hard labor and materials. To their dismay, they learned that the Helmsleys were unwilling to pay the bills. Leona claimed that much of the completed work was inadequate and they were being grossly overcharged. Angered and frustrated, many of the contractors were forced to file suit against the Helmsleys. Leona and Harry eventually settled some of the outstanding debts but by then it was too late. 

Harry and Leona had grossly underestimated the contractors. Those who had worked on the renovation and remodeling of the house knew that much of the work they had performed for the Helmsleys was being billed to some of Harry's other properties. Although it was not an uncommon practice to falsify business expenses in order to evade taxes, it was highly illegal. Exasperated with the manner in which they were treated, the contractors decided to wage their own campaign against the Helmsleys. They wanted the world to know that the work they were doing on the mansion was being written off as a business expense and they had the invoices to prove it.

Palace Coup

According to Michael Moss' book Palace Coup: The Inside Story of Harry and Leona Helmsley, the contractors mailed a stack of invoices to the New York Post, resulting in the release of an article in 1985 revealing to the world how the Helmsleys did business. It wasn't long before the government caught wind of the Helmsleys' illegal business practices, instigating an investigation that would eventually land Harry and Leona in serious legal trouble with the IRS and ruin their reputations for years to come.

It took three years, but eventually the Helmsleys were indicted. They faced 188 counts of tax fraud for illegally charging more than $4 million of personal expenses to Helmsley Enterprises subsidiaries and conspiracy to defraud the government of over $1 million in personal income taxes. To make matters worse, Leona, in particular, faced federal charges of extortion and mail fraud. However, the Helmsleys were not the only ones to be indicted.

Two ex-staff members, Frank Turco and Joseph Licarci, who had been previously employed by Helmsley Enterprises were also charged as accomplices to Harry and Leona's scheme to defraud the government. Allegedly, the two men were believed to have falsified documents and conducted fraudulent practices, among other crimes, in an effort to assist the Helmsleys in hiding their growing expenses. They, too, were to stand trial for their alleged crimes. Moreover, there was a good chance that all four would spend a considerable amount of time behind bars and be forced to pay back taxes to the government.

Few people sympathized for the Helmsleys' predicament. In fact, many welcomed the news that the Helmsleys could face jail time, especially Leona, who had a made lot of enemies. She had become notorious for her gross mistreatment of employees at many of the Helmsley hotel chains across the  United States . Yet, she was even more widely known throughout the country for her obsession with perfection.

Leona was brought into the public spotlight when she appeared in a series of highly successful ad campaigns devised to boost occupancy sales for their luxurious Madison Avenue hotel known as the  Helmsley Palace . Her image as a demanding "queen" expecting the best in terms of luxury accommodations appeared in magazines, newspapers and billboards in almost every major city and airport across the United States . Leona's image was almost as popular as many household brands.

Leona in ad for the Helmsley Palace

In actuality, Leona considered herself to be a queen of sorts, at least of the Helmsley hotels. She had absolute rule over the operation of her and her husband's hotel properties and she was a stickler for perfection. Any transgressions by employees would be met with scathing contempt, ridicule and banishment from her realm.

Her volatile temper and intolerance to disobedience became legendary. There were hundreds of accounts from ex-employees concerning incidents where Leona would threaten and verbally abuse them before being terminated for the slightest infraction. She was also known to extort money and services from employees and business suppliers, under threat of losing their positions or her as a client. Employees were even known to tremble out of fear in her presence because of her unpredictable behavior. Leona's notorious moods and unpleasant character earned her the nickname, the "Queen of Mean." Her reputation and unethical business conduct would eventually prove to be her undoing.