She was known for her ruthless business sense, flamboyant personality, and the tyrannical behavior that earned her the nickname the Queen of Mean – a name, by the way, that she enthusiastically embraced. Leona Helmsley was a larger than life figure. A high school drop out who later became a hotel baroness who amassed a multi-billion dollar fortune that made her one of the wealthiest women in the world. Her rise to the top of the New York City real estate world is a wild story matched only by her spectacular fall from those lofty heights. A fall that included tax evasion charges and a stint behind bars in a Federal prison. And as if her life wasn't crazy enough, in death she shocked the world with one of the most insane wills of all time. Leona certainly wasn't boring…
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Leona Helmsley was born Lena Mindy Rosenthal in Marbletown, New York on the 4th of July, 1920 and grew up in Marbletown, Brooklyn, and Manhattan. The third of four children, with two older sisters and a younger brother, her family moved six times when Lena was still very young. She excelled academically but dropped out of high school to seek her fortune. She changed her name several times along the way, from Lee Roberts to Mindy Roberts to Leni Roberts. Eventually, she decided on Leona Mindy Roberts and legally changed her name.
When Leona was 18 years old, she married for the first time. Leo Panzirer was an attorney who was 10 years older her senior. Four years later, the couple's son Jay was born. In the late 1940s, they divorced and Leona went to work as a secretary for a garment industry executive named Joseph Lubin. It wasn't long before she became romantically involved with Lubin and eventually married him. They divorced a few years later. However, shortly after their divorce, they rekindled their romance and remarried. Their second marriage lasted five years before it too ended in divorce.
So there Leona was, 42 years old with a 20-year old son, no husband, no college degree, and no job. This was not the life of adventure and wealth she had dropped out of high school to pursue. However, what Leona did have was an unshakeable belief in herself. She knew she would have to start small and work her way up the ladder, so she set out to do just that. In other words, she went to work. First at a sewing factory and then as a secretary at the real estate firm Pease and Elliman. Two years after she started that job the firm underwent a change in ownership that would forever change her life.
Leona convinced her new bosses to see her as more than just a secretary. She believed she could outsell the firm's other brokers, and her bosses gave her the chance to prove that. She started with a small client list and before long was assigned to more upscale condos and co-ops. Within a few years, Leona became vice president of the firm, earning six figures in salary and commissions. This allowed her to buy a luxurious penthouse in Manhattan. She had finally made it by almost anyone's standards. But it wasn't good enough for Leona. She wanted a much grander life.
Enter Harry Helmsley, one of the wealthiest men in America at the time. He was a 59-year old real estate mogul and owner of some of the most reputable real estate firms in New York. In the mid 1960s, he branched out from primarily leasing and managing office space (including the Empire State Building) and into the residential market as he had become interested in cooperatives and the conversion of rental apartments into condos, since there was a great deal of money to be made in the area. Helmsley also owned a handful of hotels, one of which included Manhattan 's exclusive Carlton House.
Leona was already a successful broker in the selling and conversion of apartments to co-ops and condos and in 1969 she decided she wanted to work for one of Harry Helmsley's residential real estate firms. The problem was, she didn't know Harry. She sought him out and shortly after their meeting she was made senior vice president in control of cooperative sales for Harry's residential properties. This position gave her access to the most prestigious properties that yielded the most money. It is believed that Leona also joined the firm so that she could get the chance to meet the "king of real estate" Harry Helmsley.
Almost as soon as Leona and Harry met, rumors began to surface that they were having an affair. This presented a problem for Eve, Harry's wife of more than 30 years. Harry and Eve divorced in 1971 and Harry and Leona married in the summer of 1972. Within a decade, Leona had conge from an uneducated, single mother working in a sewing factory to the wife of one of the richest men in America. It was, finally, her dream come true and not a moment too soon.
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Leona took on her new role both as a married (again) woman and as senior vice president of Harry's chain of Helmsley Hotels. As part of her marriage, she received 10% of the stock in the subsidiaries. Â The marriage had literally saved her from losing the lavish lifestyle she previously enjoyed before meeting Harry, as she was on the verge of losing her real estate license in the months before her wedding day. Near the end of 1971, Leona had attempted to force tenants in one of the residential properties she managed to buy the condo conversion happening in their building. They claimed that Leona threatened them, telling them that others would buy their homes if they did not act quickly and buy the property themselves. If they refused, she would verbally abuse them until they gave in. A handful of tenants had enough of this abuse and sued Leona.
Leona was found guilty and ordered to pay compensation to all the tenants of the building, as well as give each of the residents three-year leases. Also, her real estate license was temporarily suspended pending further investigation into her shenanigans. But, in her new role as Harry's wife and with all the benefits that came with that, it didn't matter as much to her that she would not be able to practice real estate. So, she decided to focus all of her attention on the hotel chain.
And she was in luck as in the 1970s, Harry had a dream. He wanted to build a luxury hotel unlike any the world had ever seen. On September 15, 1980, the opulent Helmsley Palace Hotel had its grand opening celebration. It was an invitation only event with guest that included socialites, statesmen, government officials, celebrities, and selected journalists. The hotel was a huge hit. Not many people had ever seen such an extravagantly luxurious hotel. It was a spectacle. It was everything Harry had dreamed.
The Palace was 51 stories tall and had approximately 1,143 rooms. The hotel's rates were by far the highest in the city. Harry and Leona were proud of what they accomplished. Many years and a ton of effort went into the planning, construction and development of the Palace. Harry managed most of the groundwork and  Leona spent a great deal of time and energy managing the decorating and staffing of the hotel.
Harry gave Leona the job of running the hotel. As President of the Palace, Leona was determined to give the hotel's guests unprecedented service. Leona first became a part of the public eye in a series of successful ad campaigns for the Helmsley Palace in which she appeared as a demanding Queen expecting the best. These ads appeared in newspapers, on billboards, and in airports in almost every major city in the United States. This image of Queen Leona was almost as popular as major household brands. In actuality, Leona did consider herself to be a queen of sorts, at least of the Helmsley hotels. She had absolute rule and she was a stickler for perfection. Any transgressions by employees would be met with scathing contempt, ridicule, and literal banishment from her realm.
She demanded total perfection from her staff and was a stickler for detail. Employees were required to work above and beyond their call of duty. Any mistakes reflected poorly on not just the hotel, but on Leona personally. She ran an excessively tight ship. Any slip ups were reprimanded with a tirade and employees were often fired on the spot. Needless to say, those who worked beneath Leona began to dislike her and in time many began to despise and fear her. She had a legendarily short temper that often quickly moved from pleasant to fuming mad within moments. Under Leona's reign, the Palace had an extremely high employee turnover ratio. Leona's frequent explosions became the subject of much gossip amongst employees. Almost the entire staff had at some point or another witnessed or been the target of one of her tirades. Leona was at least consistently mean to a vast majority of her employees, earning her the nickname, "the Queen of Mean."
Many who knew Leona began to hate her – one enough to attempt to kill her. Leona and Harry were attacked while sleeping one night in the 1980s. Leona was stabbed in the chest, but managed to survive the attack. The perpetrator was never caught. Leona believed it was a former employee.
In 1983, with the Palace enjoying success, the Helmsleys bought the summer house of their dreams. Dunnellen Hall was a 21 room mansion on 26 acres in Greenwich, Connecticut. They paid $11 million for the property. Leona and Harry then set out to renovate their new summer home to the tune of $8 million more dollars. Despite their billionaire status, the Helmsleys decided they didn't really feel like paying the bills on the renovation or the tax bill that would come.
When a group of contractors, including decorators, gardeners, painters and landscapers, attempted to collect on the money owed to them, they learned that the Helmsleys were unwilling to pay the bills. Leona claimed that much of the work was poorly done and they were being grossly overcharged. Unfortunately for the Helmsleys, they underestimated the contractors they tried to ditch paying. The contractors filed suit against the couple. The problem was, many of the contractors knew that the Helmsleys were billing the work on the house to their hotel properties. While it was not an uncommon practice to falsify business expenses in order to save tax money, it was highly illegal.
The contractors 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. They mailed a stack of invoices to the "New York Post". This resulted  in the publication of a 1985 article revealing to the world how the Helmsleys did business. It wasn't long before the government caught on to the Helmsleys' illegal business practices and began the investigation that would eventually land Harry and Leona in serious legal trouble with the IRS.
It took three years for the IRS to build their case but eventually the Helmsleys were indicted on 188 counts of tax fraud for illegally charging more than $4 million of personal expenses to Helmsley Enterprises and conspiracy to defraud the government of over $1 million in personal income taxes. A former housekeeper testified that Leona once proclaimed "We don't pay taxes. Only the little people pay taxes" – a now infamous line. Leona also faced federal charges of extortion and mail fraud.
When the Helmsleys were indicted, many believed the Queen of Mean would finally get what she deserved. The charges against the couple could have resulted in more than one hundred years behind bars and considerable fines if they were found guilty. On August 30, 1989 Leona was convicted of 33 felony counts of trying to defraud the government and IRS, including mail fraud, tax evasion and filing false tax returns.
Leona received a sentence of sixteen years and was fined a little more than $7 million, most of which was to be paid back to the federal government. Immediately following the trial, Leona appealed her case to the New York Supreme Court and succeeded in having her prison sentence minimized. She ended up serving approximately nineteen months in a federal penitentiary plus two months house arrest.
On January 4, 1997 Harry Helmsley died at the age of 87, leaving his entire fortune to Leona. That fortune included the Helmsley hotels, the Helmsley Palace and the Empire State Building, estimated to be worth well in excess of $5 billion. She became in that moment one of the wealthiest people in the United States.
A decade later, on August 20, 2007, Leona Helmsley died of heart failure at the age of 87 and was entombed in a $1.4 million marble mausoleum. She also had one last moment of pure spite, when her will was read. Who would inherit her billions?
First off, she left $4 billion to the Leona M. and Harry B. Helmsley Charitable Trust. Very commendable. But here's where things get a little crazy. Leona had four grandchildren. She left two of them with $5 million each in cash and $5 million in trust, on the condition that they visit their father's grave once a year. They are required to provide proof every year in the form of a signed guestbook at the cemetery. The other two grandchildren got nothing. The supposed reason these two unlucky grandchildren got nothing is because they did not name any of their children (Leona's great grandchildren) after her late husband Harry.
In place of those two grandchildren, Leona left $12 million dollars to her beloved white Maltese dog, Trouble. A judge would later rule this amount to be excessive and questioned Leona's sanity at the time she will was filed. Therefore the final amount was reduced to $2 million. Leona's brother, Alvin, was appointed trustee of his sister's estate and full time guardian of Trouble. This job came with an annual salary of $60,000. Even after the trust was reduced to $2 million, the dog received a $100,000 a year security team, $8000 a year worth of grooming and $1200 a year worth of food. Leona left her chauffeur $100,000. She set aside $3 million so her mausoleum would be "washed or steam-cleaned at least once a year".
Trouble passed away in December 2010 at the age of 12. Her will clearly stated that upon Trouble's death, the dog was to be laid to rest next to Leona in the mausoleum. Unfortunately, this never happened because New York state law prohibits pets from being buried in human cemeteries. Tragic.
