Remember ‘The Queen Of Mean’: Billionaire Leona Helmsley Sentenced To Prison December 12, 1989

OK people time for a pop quiz. Who is reputed to have been so evil she made the Wicked Witch of the West hop on her broomstick and hightail it out of Oz? What woman, also known as the Queen of Mean, was so selfish she told her housekeeper “only the little people pay taxes?” Give up? Its convicted criminal and dead billionaire, Leona Helmsley, who payed for her arrogance when she was sentenced to prison for income tax evasion on December 12, 1989.

Leona Helmsley had it all. She was already a multi millionaire in her own right when she married Harry Helmsley. He was a billionaire in late middle age and he divorced his wife of 33 years for Leona. Harry owned some of New York’s finest hotels and the Empire State Building.

Harry Helmsley was already showing signs of becoming feeble when they wed and in just a few short years, Leona directly controlled twenty-three hotels in the chain . Among the hotels owned by the Helmsleys were the New York Helmsley Hotel, the Helmsley Palace Hotel, and hotels in Florida and other states. They also owned Tudor City apartments, Helmsley- Spear Management and Brown, Harris and Stevens, one of the world’s largest real estate brokers.

Most people who are worth a great deal of money are generally content and some are charitable kind human beings, but not Leona. We are talking about a woman who was so bitter that after her own son died of a heart attack, she served his widow with an eviction notice only days after the funeral, than sued her son’s estate. Leona wiped out her daughter in law financially. The son’s widow can only say, “To this day I don’t know why they did it.”

When Queen Leona wasn’t turning her own family out in the street, she turned on her employees. For years, Mrs. H ran rampage through her husband’s hotels firing people for the slightest mistake and publicilly humiliating them with tirades of insults and obscenities.

Famous Harvard University Professor Alan Dershowitz, was having breakfast with Her Highness, Lady Leona one morning in one of the Helmsley Hotels when a waiter brought him a cup of tea with some water spilled in the saucer. According to Dershowitz, Leona grabbed the cup from him and smashed it on the floor, then demanded that the waiter get down on his hands and knees and beg for his job.

In another memorable incident, Dear Leona decided to stiff Eugene Brennan, who built a barbecue pit for her home. When she received the agreed upon invoice for $13,000, she claimed the work was inferior and refused to pay the bill. Jeremiah McCarthy, the chief engineer of Helmsley-Spear, who was a friend of the man and hired him for the job, told her her that Brennan had six children to support. Helmsley replied, “Why didn’t he keep his pants on? Then he wouldn’t need the money.”

Nastiness and arrogance finally caught up with Leona. In 1983, the happily horrible Helmsleys purchased Dunnellen Hall, a 21-room mansion in Greenwich, Connecticut, to use on weekends. Leona was constantly billing renovation expenses to the company illegally. When Jeremiah McCarthy, the engineer whose friend was stiffed for his work, refused to comply with her demands that he violate tax laws, Leona told him, “You’re not my fuc*ing partner! You’ll sign what I tell you to sign.”


This time around Leona decided that she would refuse to pay a cool eight million dollars in construction expenses and the contractors took her to court. They were so angry at the treatment received at the hands of the self absorbed Mrs. Helmsley that the contractors also sent copies of the invoices to the New York Post. The newspaper wrote an article that caught the attention of then United States Attorney Rudy Giuliani, who indicted the Helmsleys and two of their associates on income tax charges and extortion.

Harry was ruled mentally and physically unfit to stand trial and Leona faced her day in court alone. She was found guilty of one count of conspiracy to defraud the United States, three counts of tax evasion, three counts of filing false personal tax returns, sixteen counts of assisting in the filing of false corporate and partnership tax returns and ten counts of mail fraud. After a change of lawyers and much legal wrangling, on December 12, 1989, Queen Leona was sentenced to a four-year prison sentence, 750 hours of community service, and a $7.1 million tax fraud fine.

The great and powerful Mrs. Helmsley only served 18 months in prison. Harry died in 1997 and left everything to Leona. Now Leona was alone with her $5 billion dollars and classy friends like Imelda Marcos and the Noriega’s. She decamped herself to a penthouse apartment atop the Park Lane Hotel, where she spent her final years.

At the end of her life, her husband long dead, her friends dead or in prison, Leona lived alone in luxury with a dog named Trouble. She only ventured out rarely. She did mange to lose a lawsuit filed by an employee she fired for be gay. He collected 11 million dollars and Leona crept back to her nest to die.. Leona Helmsley, the True Queen of Mean, died in 2007 at age 87. She left $12 million to her dog, Trouble.