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Leona Helmsley (born Lena Rosenthol [July 4]], 1920 in Ulster County, New YorkLeona Helmsley is a New York City hotel operator and real estate investor.

As a young woman, she displayed intelligence but dropped out of high school. She claims to have later attended Hunter College, but that institution says that it has no record of her ever having attended. Before her involvement with Harry Helmsley she was previously married to two other men, once to attorney Leo E. Panzier, and on two different occasions to garment industry figure Joseph Lubin.

She was a real estate agent when she met and began her involvement with the then-married multi-millionaire real estate investor Harry Helmsley. Supposedly under her influence, he began a program of conversion of apartment buildings to condominiums, confounding some of the tenants. He eventually despaired of the legal complications that this entailed and began to concentrate on the hotel industry, building the Helmsley Palace on Madison Avenue near Saint Patrick's Cathedral. Leona, by now married to Helmsley, became known as the "queen" of this palace, supposedly acquiring the nickname "The Queen of Mean" from its employees. However, the hotel was well-located and apparently well-managed in some regards; some reviewers found it to be well worth its rather extravagant pricing.

In the 1980s she became infamous primarily for two things – as a tyrannical "boss from hell" whose petulance seemed ill-suited to the "hospitality" industry, and for being prosecuted, and eventually convicted and sentenced to prison for, income tax evasion. Harry was initially charged as well; however, he was found to be both physically and mentally unfit to stand trial, having begun to appear at least somewhat enfeebled shortly after the beginning of his relationship with her years before. At her trial, one of the key witnesses against her was a former hotel maid who recounted having heard her say, "Only the little people pay taxes." Most legal observers tended to feel that her personality tended to alienate the jurors so strongly that it trumped some rather compelling points made by her defense team, such as the fact that the item mentioned above was an example of usually-inadmissible hearsay. She was convicted but eventually managed to have her sentences, originally decades long, largely set aside except for 18 months which she actually served. She became something of a popular culture symbol of 1980s wretched excess for a time, but is now largely forgotten outside of the New York City area, other than that her last name was adopted as part of the gimmick of star wrestler Hunter Hearst Helmsley ("Triple H"). Harry left her his entire fortune, estimated to be worth well in excess of $1 billion, upon his death. However, her legal difficulties were not over. In 2002, she was sued by Charles Bell, a former employee, who sued her alleging that he was discharged solely for being homosexual. A jury agreed and ordered Mrs. Helmsley to pay Bell $11,700,000 in damages; a judge subsequently reduced this amount to $554,000.

has recounted that a feud between her and fellow billionaire real estate tycoon Donald Trump is well-known within the real estate community.

The story of her adult life was dramatized in the 1990 TV-movie , which starred Suzanne Pleshette as Leona and Lloyd Bridges as Harry. Ms. Pleshette was nominated for an Emmy Award and a Golden Globe Award for this portrayal.

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