This Day in Jewish History, 1989

New York's 'Queen of Mean' Is Convicted

Hotelier Leona Helmsley earned herself a name for tyrannizing her employees, but she was also an active philanthropist, and made her dog very rich.

Leona Helmsley
Leona Helmsley and Trouble, January 31, 2003 AP

On this day in 1989, real estate magnate Leona Mindy Roberts Helmsley, was convicted of Federal income tax evasion and other charges. An icon of the 1980s “greed is good” philosophy, the so-called “Queen of Mean”  also had a heart: Helmsley bequeathed much of her fortune to charity. She also left millions to her to her dog Trouble, making him the richest Maltese in the world.

Helmsley was born Leona Mindy Rosenthal on July 4, 1920 in Marbletown, New York. Her father was a milliner and her mother a housewife, both immigrants from Poland. She had one brother, Alvin. Rosenthal changed her surname to Roberts after high school.

Helmsley’s first marriage, to lawyer Leo E. Panzirer, ended in 1952 after 11 years. They had one son, Jay, who would die of a heart attack at age 42. In 1953 she wed Joe Lubin, a marriage that lasted seven years.

Helmsley worked as a model, among other things, before getting her foot on the property career ladder in the 1960s, rising from secretary to property broker. In 1968, already a millionaire in her own right, she met her future third husband, the multi-millionaire property magnate Harry Helmsley, and joined one of his firms as senior executive in 1970. Harry, also a self-made man, divorced his wife of 33 years to marry Helmsley in 1972.

The pair ran a property empire which grew to an estimated $5 billion and included the Empire State Building and the Park Lane Hotel. In 1980, Harry made his beloved wife president of the chain. Their glamorous lifestyle was complete with a 100-seat private jet and a slew of luxurious homes.

Why not to stiff contractors

Starring in a series of ads for the hotels made Helmsley a household name, according to the New York Times. In the ads, Helmsley appeared as a “queen,” demanding nothing but the best for her guests.

Staff, however, felt that if there was a queen in town, it wasn't a guest. Employees were reportedly so terrified of her that they organized a warning system to alert when she was heading to a hotel. Contractors and vendors accused her of holding back payments.

It was a combination of these factors which landed her in jail.

In 1983, the Helmsleys bought a $11 million Connecticut mansion called Dunnellen Hall. After they disputed the $8 million remodeling bill, the contractors sued in 1985. It emerged during those proceedings that the Helmsleys had a habit of writing off personal purchases - such as this luxury home makeover - as business expenses, and the plaintiffs sent invoices to the New York Post to prove it.

The New York Post’s scoop led to a criminal probe and the pair was indicted along with two associates in 1988. Harry, who was unwell, was declared unfit to stand trial. The proceedings against Helmsley  began in 1989.

In court, disgruntled employees came out of the woodwork. The infamous testimony of former housekeeper Elizabeth Baum sealed the Queen’s reputation:  “You must pay a lot of taxes…. We don't pay taxes. Only the little people pay taxes,” Baum quoted Helmsley as telling her – though Helmsley would later deny she ever said any such thing.

A vintage ad featuring Leona Helmsley
Jamie, Flickr

In 1989, the 69-year-old was found guilty of 33 felony counts and convicted of evading $1.2 million in Federal income taxes. She was acquitted of the most serious charge against her, however - extortion. In 1992, she began a four-year sentence on April 15, the deadline for filing tax returns. Helmsley served only 19 months in prison and two under house arrest in her Park Lane Hotel penthouse.

Harry died in 1997, and the Queen lived the rest of her life mostly alone. When she died of congestive heart failure, aged 87, it was at Dunnellen Hall. That year, Forbes ranked her the world’s 369th richest person with an estimated net worth of $2.5 billion.

In her later years, she showed a kinder side, donating millions to help the families of firefighters after 9/11, and for medical research. And though she left nothing to two out of four of her grandchildren, she did leave $12 million to her Maltese terrier Trouble, who died in 2011. Though in 2008, a judge gave the disinherited grandkids some of Trouble’s fortune. And she left about $4 billion to a charitable trust in her and her beloved Harry’s names.