The SafeEstates Blog

The Queen of Mean and Trouble

Born in 1920, Leona Rosenthal dropped out of a Brooklyn high school to seek her fortune. She became a millionaire selling real estate in Manhattan. In 1972 she married real estate entrepreneur Harry Helmsley. Together they built a real estate empire that included the Empire State Building. Their hotels included the Helmsley Palace, New York Helmsley Hotel, Park Lane Hotel, and 20 other hotels in Florida and other states.

In 1988, Rudy Giuliani (then U. S. Attorney for the Southern District of New York) indicted them on tax related charges and extortion. Because Harry was ruled unfit to stand trial, Leona faced the charges alone. The trial highlighted Leona’s abusive behavior toward family, employees, vendors and executives, earning her the title “Queen of Mean.” She was convicted of tax evasion, filing false tax returns, and mail fraud but was acquitted of extortion. Leona was sentenced to 16 years in prison. On appeal, she was represented by attorney Alan Dershowitz and her sentence was reduced. She was released from prison after serving 19 months.

Harry died in 1997, leaving Leona his entire fortune. Leona was forced to give up most of the hotels because New York state law does not allow convicted felons to hold liquor licenses. She spent her final years living in the penthouse of the Park Lane Hotel. After her death in 2007, Leona was buried beside Harry in a mausoleum in Sleepy Hollow Cemetery.

In her 2005 will, Leona left most of her $4 billion estate to the Leona M. and Harry B. Helmsley Charitable Trust. She also left a $12 million trust for her Maltese dog, Trouble, and a $3 million trust for care of the Helmsley mausoleum.

Leona had no living children. She was survived by a brother and four grandchildren. In her will, bequests were included (outright or in trust) for her brother (Alvin, $15 million) and two grandchildren (David, $10 million and Walter, $10 million). The other two grandchildren (Craig and Meegan) received nothing “for reasons that are known to them.” However, the surrogate court, in a settlement of challenges to the will, concluded Trouble’s trust amount exceeded the trust purpose and reduced it to $2 million. The court ordered $10 million taken from Trouble’s trust to be distributed $6 million to Craig and Meegan and $4 million to the charitable trust.

Trouble died in 2010, with the remaining pet trust funds added to the charitable trust. Leona wanted Trouble to be interred in the mausoleum with her but state law prohibits burial of animals in human cemeteries. Trouble was cremated.
I expect it was not always easy for Sandor Frankel to be Leona’s estate planning attorney and trusted legal advisor. However, in 2019 the surrogate court, because of the complexity of the estate, awarded $100 million in executor fees to Leona’s four executors, including Mr. Frankel. He is also a trustee of the charitable trust. It has grown to over $6 billion and focuses on medical research and health institutions.
What is the point of this story? If something about Leona resonated with you, give us a call so we can listen to your concerns and advise you with solid solutions.
~ Randy Hooper