May 15: “Queen of Mean” Leona Helmsley Checks Into Danbury Prison


Leona Helmsley was one of the most infamous celebrity billionaires of late 20th century New York, a hotel and real estate magnate who gained national notoriety for her reportedly tyrannical treatment of her staff.   The wife of hotelier Harry Helmsley, Leona became the face of a marketing campaign that cast her as a “queen” who would only tolerate the highest and most exacting standards for Helmsley-owned hotel properties.  The New York tabloids, however, teemed with stories of Mrs. Helmsley hurling abuse at hotel staff, colleagues, and building contractors and labeled her “the Queen of Mean” — a nickname that would follow her for the rest of her 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, but it wasn’t until 1989 that one of them resulted in a conviction.  Rudy Giuluani, then serving as a U.S. Attorney, indicted the Helmsleys on charges of tax evasion regarding lavish, multi-million-dollar renovations on 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 eventually found guilty on 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 an appeal, her sentence was shortened 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, where “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