Roch Society
By Lola Johnson & Erin Latham Shea
July 19th, 2025
Leona Helmsley’s decision to leave her dog, Trouble, $12 million drew legal challenges, media scrutiny, and lasting debate about her legacy.
It truly sounds like something out of a movie: a New York hotel tycoon leaves her beloved dog, Trouble, $12 million, cutting out two of her grandkids from the will. But for Leona Helmsley – dubbed the “Queen of Mean” in the tabloids – it was just another page in an already zany life story.
The Helmsleys built a sprawling $5 billion real estate empire that included the Empire State Building and a chain of luxury hotels.
After the death of her husband, Harry Helmsley, in 1997, the center of Leona’s world became a tiny white Maltese named Trouble.
More than just a dog, Trouble was Leona’s closest companion, treated not like a pet but as a child (Leona’s only son, Jay, passed unexpectedly in 1982 due to heart failure). The ‘Queen’ insisted that Trouble be called “Princess” by the entire staff and public, and, by all accounts, Trouble was treated with every ounce of the Helmsley fortune’s extravagance.
When Leona Helmsley died in 2007 at age 87, it became clear just how deeply she loved and prioritized Trouble.
In her will, Helmsley left a staggering $12 million in a trust to ensure that her dog would receive the same level of care and luxury after her passing.
Leona’s $12 million dog trust set off a media storm as well as a family feud. While two of Leona’s grandchildren were each given $5 million, the other two were left out entirely. The disinherited grandchildren contested the will in court, claiming their exclusion was unjust. Ultimately, a judge reduced Trouble’s trust from $12 million to $2 million, reallocating the remainder back to the estate. Even so, this left Trouble as one of the richest pets in the world.
Lola Johnson & Erin Latham Shea, Roch Society
