May 15: Hotels’ “Queen of Mean” Checks Into Danbury Prison


Leona Helmsley was one of the most visible celebrity billionaires of late 20th century New York. The wife of hotelier Harry Helmsley, Leona became the face of an immensely successful marketing campaign that cast her as a “queen” who would tolerate only the highest and most exacting standards for the Helmsley-owned luxury-class hotel properties. The campaign boosted the Helmsley Hotel quality image and propelled Mrs. Helmsley’s image into the superstar class. That regal image turned sour, however, when Helmsley gained national notoriety for her reportedly tyrannical treatment of staff. The New York tabloids teemed with stories of Mrs. Helmsley hurling abuse at hotel workers, colleagues, and building contractors. They labeled her “the Queen of Mean” — a nickname that followed her for life.

An ad featuring “Queen” Leona Helmsley, circa 1986.
Throughout the 1980s, the Helmsleys encountered wave after wave of highly publicized investigations and federal lawsuits regarding tax evasion, tax fraud, and extortion. None produced a conviction until 1989. That year, Rudy Giuliani, then serving as a U.S. Attorney, successfully prosecuted the Helmsleys on charges of tax evasion regarding lavish, multi-million-dollar renovations to their Greenwich, Connecticut mansion. During the trial, a former Helmsley housekeeper famously testified that Leona once told her, “We don’t pay taxes. Only the little people pay taxes.”

Leona was ultimately found guilty of multiple charges of tax evasion, tax fraud, and mail fraud. Since the elderly Harry Helmsley was in failing health and ruled unfit to stand trial, only Leona was convicted and sentenced to jail time. After a failed appeal, her sentence was shortened from 16 to four years in prison, and on May 15, 1992, the 71-year-old Helmsley arrived at the low-security Federal Correctional Institution in Danbury, Connecticut, where she served 18 months before returning to her Greenwich home. There, “the Queen of Mean” died in 2007 at the age of 87.

Further Reading

Laurie Goodstein, “Leona Helmsley’s Heartbreak Hotel,” Washington Post

Enid Nemy, “Leona Helmsley, Hotel QueenNew York Times