Why not? Only the little people pay taxes right?
~ Leona Helmsley

Leona Helmsley also known as "The Queen of Mean" was a hotelier and real estate agent in the 1990 TV movie The Queen of Mean - The Leona Helmsley Story. She married New York real estate tycoon Harry Helmsley; though a real life person and story, she is portrayed by Suzzanne Pleshette. Helmsley, manager of the Helmsley Palace Hotel, was notoriously a shrewd and cruel manager who regularly fired and corrected her employees through micro management. Leona was later convicted of tax evasion for writing off expenses for their personal home renovations as a business expense.


Born Lena Mindy Rosenthal, Leona assumed her trademark identity while working for a smaller real estate agency in New York. Among the glaring trial that would later encompasses Helmsley, the personal history of assuming the throne of a real estate empire enabled her to mistreat her employees. Leona was deemed the Queen of mean for her tough nature and attributed it to the fact that she was a woman, for if she were a man acting the way she did, she would be considered a tough boss.


Leona, back then called Lena, met her first husband Joeseph "Joe" Lubin in a club during mid day and ultimately begins their mutual love affair with one another, even though they both tell the other they are married to someone. Joe insists that Leona doesn't come to the club just to dance, and an affair is assumed to have begun. Later, while out with her actual husband, the couple  are accused of stealing salt and pepper shakers from a fine dining restaurant while on a double date. Leona looks away, seemingly guilty, but says she didn't have them. This prompts Joe to pay for them anyway to which Leona remarks that he should have denied it because the restaurant couldn't proven the theft occurred. Later Joe announces that his company needs him to relocate, which he knew Leona wouldn't approve of and their estrangement began to draw closer.

Jay Rosenthal

The one tie Leona always loved but kept at a distance was her son Jay, who she hid from her coworkers at the real estate agent she works at in New York. She remarks that none of her co-workers know how old her son is and implies that she had no intention of telling them about her personal life. She takes the opportunity to later erase Joe from her history and insist her first husband, the father of Jay, was the only time she was married. Jay would later come to work for her and get in trouble for which she scolded him. Upon Jay's death, via a third heart attack, Leona blamed his second wife who wanted to claim the company Jay oversaw in Orlando. Leona even went as far to say that the wife was Jay's killer.

Harry Helmsley

She later meets Harry Helmsley at a New York gala where she promptly introduces herself, and Harry identifies her as a woman that doesn't just follow, but could lead. Harry at the time was married to Eve Helmsley, but this doesn't stop Leona from flirting with Harry and subsequently having an affair wth him. She made it her personal mission to pursue him and gain whatever respect she could by being the wife of Helmsley. She used Harry and is shown to have even leveraged his love in ways that made him see her conniving ways, but refuse to escape them. 

Building Her Empire

Though not initially an industry titan, she was incredible at her job, according to herself she was the best salesperson in the company. Originally a regular agent, securing a Parks Avenue project elevated her status to which she earned an office with her name on the door. At this time she changed her name to Leona Roberts, an assumed moniker that would disassociate herself from her former husband and adult son. While hosting a meeting, a late employee arrives to which Leona chastises him for his lateness, though only by a few seconds. When the employee asks if she's the warden, she assures him that she is. The employee initially treats her rudely and goes toe to toe with her for her insults, to which she seems to admire.   

After working with the firm she romances Harry Helmsley into a position under his empire for which she works to get closer to him, even as her accounts are failing. She begins to show signs of a distasteful attitude towards her employees, no matter their rank. During one moment she insists to not accepting any calls and asks if her employee is either deaf or stupid for not listening to her request.

Leona pulls off a scheme in order to become a Helmsley by pretending she has a secret admirer who wants her to move to Atlanta. She creates an ultimatum that sites she will leave to Atlanta with her fake lover unless Harry leaves his wife. She later uses this position as the future Mrs. Helmsley to leverage a phony account that was used to make Harry admire her, even though her previous dealings had all been failures. She continues to grow more mean and vile towards employees and more jealous of her new possession Harry. Her good friend, and the former employee that tested her at the local firm confronts her to tell her she's mean now, not just tough. As Harry's health declined in the later years of their relationship, Leona felt that she was the shield to the Helmsley fortune and company; with Harry as her trophy for it all. 

Queen of the Palace Hotel 

Upon the renovation to the largest hotel in New York, Leona is charged as the President of the hotel chain and overseer of the construction of the hotel. During this time her ill stricken son Jay is promoted, at her command, to VP of a distributor in Orlando, Florida. Stanley, the current President of the Orlando branch, tells Leona that her son is overbooking the furnishings for hotels of the Helmsley Corporation. Jay was pocketing the difference of the surplus furnishings and Leona as a result fires Stanley and instead insists Jay would do no such thing. Leona makes a speech that outlines her determination and willingness to not defend her own son in order to withhold power:

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As you know I am a very determined person. And I determined long ago that I was going to marry a man so powerful that just by being his wife I would command absolute attention and respect. I've done that. I have done better than Sandra, I have done better than Sylvia, I have done better than most women would dream possible. If you think as my son you could do anything to destroy that, you are gravely mistaken. If you ever do anything again that puts my marriage in danger, I will hang you out to dry.
~ Leona Helmsley

Soon after Leona would become a more visible member of the Palace Hotel, and would appear on publications and press release materials. The advertising or PR agent, Molly, in charge creates the idea that Leona is not just the manager, but the queen of the Palace Hotel citing it is "The only palace in the world where the Queen stands guard." Leona thinks this is genius and wants to sell pictures of herself, similar to the royal family, as momentos for guests of the hotel. She commands a certain fear and respect at the hotel, so much so that the employees have a code said to every employee upon her arrival that goes: "Mama's on her way." This is done in preparation of her demands, though most don't require immediate attention. Every night, or at least on the opening night the Helmsley's are introduced as the King and Queen of the Palace Hotel.

Downfall and Subsequent Trial

An employee, presumably the maid who noted that Leona remarked about not paying taxes called into a news organization with information on the Helmsley's business dealings. The informant claimed that the Helmley's had an expensive pool though didn't pay a dime for it. They also found that they were writing off personal finances as business expenses to avoid taxes. This was compounded with other ridiculous demands of the Helmsley's and stories that circulated around the news media. Helmsley was put to trial and served 4 years in prison with a charge of 7.1 million dollars due to 33 counts of fraud. 


Leona was a cold and cruel leader, treating every employee like a personal servant at times. Anything out of the ordinary or not to her liking was deemed their fault and could even be a fire-able offense. She regularly fired or threatened to fire employees of hers and is alluded to having lost friends because of this. She led by fear and once given the moniker of Queen, wanted to be treated that way. She displayed behaviors similar to that of someone who was bi-polar, often going from calm conversation to angry outburst. This was seen when three servers brought her a salad whose lettuce had water droplets on it for which she threatened to fire them.

Villainous Acts

1. Seduced and had an affair with the then married Harry Helmsley

2. Fired Stanley for reporting her son was stealing from the company

3. Fired the designer of the Palace Hotel's lobby in order to take credit for her work

4. Created a charade that a mystery man wanted to marry her unless Harry left his wife and married Leona instead

5. Forced Harry to evict her deceased sons widow and leave her and the children on the streets

6. Tax evasion

7. Numerous firings of employees

  • Fired security guard for talking on the phone during his break
    • When told he had five children she responded "He should've kept his pants on, then he wouldn't have a problem."
  • Fired lobby designer
  • Fired branch president Stanley (Though Harry rehired him)
  • Fired Harry's lawyer who dealt with her fraudulent apartment account
  • Threatened to fire two separate employees who took calls for her
  • Threatened to fire new employee who was one minute late to a meeting due to a fire in his apartment



  • The wrestler Triple H chose the last name Helmsley based on the real Leona Helmsley
  • The actress who portrayed Leona was nominated for a Golden Globe and an Emmy for the role
  • Some quotes from the movie were directly from interviews and footage of Leona's own words
  • The tax quote said by the character was never on camera so technically hearsay, but media outlets like the New York Times reported it and has become her most famous quote
  • The real life Leona Helmsley was no fan of fellow New York real estate mogul Donald Trump