Julie Hambleton
Julie Hambleton
March 31, 2024 ·  4 min read

Rich widow passed away, and her family and her friends received almost nothing!

If you have never heard of Leona Helmsley, she was a hotel heiress who left most of her money to her dog and almost nothing to her family. She was known for being a mean woman, and her dog got the bulk of her estate. After she passed, she left a trust fund of $12 million to her beloved pet Maltese. Her relatives got very little from her estate, if nothing at all. She had led a crooked life and her former owner would inherit the bulk of it. 

Leona Helmsley: The Queen Of Mean

Leona Helmsley became a household name in 1980s, but not exactly for good reasons. Rather, she seemed to symbolize arrogance and greed. A hotel heiress deeply involved in her husband, Harry Helmsley’s, hotel business, even her employees were terrified of her. A family woman she was not – money was seemingly the only thing that mattered to her. That, and her white Maltese Trouble. (1)

After one son Jay’s death, the only child who came to be by her side when an intruder nearly killed her via stabbing, Leona evicted her son’s widow and children from their home. She took all the furniture and everything else inside it, too, claiming that they were property of the Helmsley Estate and that it was all to repay a $100,000 loan. (2)

Perhaps Her Dog Was The Only Thing She Ever Truly Loved?

When she died in 2007, cut two of her grandchildren completely out of the trust fund she had created. Helmsley’s pampered maltese, Trouble, instead inherited the majority of her trust fund – $12 million to be exact. From there, she divided her money as follows:

  • Some millions to her brother Alvin, who she named to take care of Trouble
  • Some millions to two of her four grandchildren from her late son Jay, so long as they visit their father’s grave once a year
  • $3 million for upkeep on the mausoleum where she was buried (and also where Trouble was to be eventually buried)
  • $100,000 to her chauffeur
  • Money from sales of Helmsley residences and belongings (worth billions) to be given to the Leona M. and Harry B. Helmsley Charitable Trust.

Although a judge reduced the amount left to Trouble, it was still enough to create one last scandal for the ‘Queen’. As for her children and other grandchildren, they were left with nothing. Apparently her two grandchildren know the reasons as to why their grandmother didn’t leave them a single cent.

Her Brother Named Trustee

Leona’s brother Alvin was appointed trustee of her estate and full-time guardian of her white Maltese dog, Trouble. She had named five executors as well, who were given the task of administering her estate. In her will, Helmsley stipulated that Trouble would receive an inheritance of 12 million dollars in trust upon her death. Her brother Alvin was also given the task of finding a suitable place for Trouble to live and be taken care of after her death. He chose a 12,000-square foot family mausoleum for her pampered Maltese, Trouble. Her brother Alvin Rosenthal and her grandchildren from her late son Jay were also named in the will.

How She Earned Her Nick-Name

Leona Mindy Roberts Helmsley was an operator, real estate investor and successful broker who had a fortune worth billions of dollars. She owned many real estate firms that included residential real estate, co-ops, condos and apartments. She was also a successful hotel operator in New York City. Her husband Harry Helmsley left her his business when he died in 1997.

This woman, however, was not a nice woman. Married twice before she married Harry, she was as cut-throat as they come. She became a well-known face when she began appearing in Helmsley hotels advertisements. Though lovely to look at, perhaps, she was the opposite to work for. Helmsley employees were all terrified of her. So much so, in fact, that they actually created a kind of warning system to alert employees when she was leaving her penthouse and on the way to one of the couple’s many hotels. 

Leona Helmsley was known to fire people cold-heartedly whenever she pleased. She also famously went to prison in the late 90s because of tax evasion and fraud. Her former housekeeper famously quoted in her trial that the hotelier had once said to her “Only the little people pay taxes”. Her sentencing meant she had to pay over $8 million dollars in fines and owed taxes, as well as she spent the next two years in jail. The judge gave her 750 hours of community service to complete upon exit from prison. When they caught her having her employees doing some of those hours, though, he ordered her 150 more hours. Some people, as they say, just never change.


  1. Helmsley leaves $12M to dog, nothing to 2 grandkids.” CBC. The Associated Press. August 29, 2007.
  2. Leona Helmsley, Hotel Queen, Dies at 87.” NY Times