Jimmy “The Iceman” De Pierro passed away on June 18, 2026, at the age of 79. Raised in Queens, he had many adventures as a bike messenger in New York City, a welder, a clam digger and a professional gambler. He came to Vermont in the ’70s with friends to seek a different way of life in the Northeast Kingdom.
Jim became known around Vermont for many things: as a founding member of the Vermont Blues Society; for running for secretary of state; for his businesses in the ’80s and ’90s, Jimmy’s Rack & Roll Pool Hall and Jimmy’s Italian Ices; and more recently for his famous dog.
In the ’80s, Jim started the Italian ice business with his best friend, John. With a daily presence in Burlington, Brattleboro and Montpelier, his pushcarts were a staple across the state. He made the ices with fresh fruit and local spring water and served them at events like the Fourth of July and Bread and Puppet Theater.
In the ’90s he ran for secretary of state for the Vermont Grassroots Party, devoted to the legalization of marijuana. He received a surprising number of votes, catapulting it to major party status and kicking off a debate about whether his nickname, “Iceman,” should be allowed on a ballot.
His most recent fame came from his early life, memorialized in a popular Seven Days article. In the ’70s, as a messenger he made deliveries to movie studios, including Jim Henson’s. On a delivery of pet headshots to National Lampoon magazine, he declared his dog more charismatic than any of the professional dog models. Intrigued, the art director gave Jim’s dog, Mr. Cheeseface, a chance, and he was indeed selected for the infamous cover page “If You Don’t Buy This Magazine We’ll Shoot This Dog.”
Later in life he hit the road as a professional poker player. He played seven-card stud all across the U.S. He also had an inventive spirit and love for music and good food.
Jim was predeceased by his sister, Luise; son Luciano; and godson, Christopher. Jim is survived by his sons Jimmy and Nicolo; former wife, Kathy; and his brother, Mark. He is also remembered by his dear friends Padma, Leo, Marysue and all those who recall that on hot summer days nothing beats Jimmy’s Italian Ice.
A Celebration of Life is being planned for next summer.
This article appears in June 24 • 2026.