In the latest episode, Jason Trimmins recounts the remarkable story of George “Skippy” Cream, a legendary and complex figure in Gloucester, Massachusetts, whose legacy continues to resonate decades after his passing. Known for his fearlessness and dedication to his community, Skippy became a local hero in the 1970s and early 1980s, despite—or perhaps because of—his run-ins with the law.
Skippy, a Gloucester native from the tough Rivale Park housing project, was no stranger to challenges. At just 5’9″ and 165 lbs, he made up for his stature with raw determination and toughness. As a teenager, Skippy often clashed with law enforcement and even escaped from juvenile detention and the Salem jail. His talents led him to the boxing ring, where he achieved success, including a Golden Gloves victory in 1976. Some even claim he once sparred with the famed Marvelous Marvin Hagler. Later, Skippy opened a boxing gym to guide Gloucester’s youth, using his own turbulent past to steer others toward a better path.
Though he was deeply involved in Gloucester’s criminal underworld—leading a crew in robberies and burglaries—Skippy was known for his acts of kindness, particularly toward children. His partner, Cheryl, shared his family life, and together they made a profound impact on those around them. Skippy once allegedly stole toys to distribute to underprivileged children at Christmas, and he even took in a neglected child, providing care and stability.
Skippy’s life came to a tragic end in 1982 at the age of 27. In a heated police chase, he was shot and killed under circumstances that left lingering questions. While official reports claimed he was armed, a later analysis by a ballistics expert suggested he might have been shot in the back. His death sparked controversy, and his funeral, attended by figures like Marvin Hagler, drew an outpouring of grief from the community.
Following Skippy’s death, his family pursued a $6 million wrongful death lawsuit, ultimately unsuccessful, but the emotional toll on those who loved him was undeniable. Cheryl, his devoted partner, struggled to cope with the loss, and even the officer involved in the shooting reportedly faced mental health issues. The story of Skippy Cream became a Gloucester legend, embodying a time when the city grappled with organized crime, corruption, and social challenges before its eventual gentrification.
Skippy Cream’s life and tragic end represent the gritty reality of Gloucester’s past and serve as a powerful reminder of a man who, despite his flaws, remains a symbol of strength and resilience in his community.
