When FBI agents placed documents promising freedom in front of him, the 64-year-old gangster looked them in the eye and refused. Not because he didn’t know about the betrayal of his successor—he knew very well. He simply believed that snitching was worse than another ten years in prison. Who was the man who twice chose prison walls over compromising his own conscience?
A Fourteen-Year-Old in a Marine Uniform
Howard Thomas Winter was born in Boston on March 17, 1929, in the West Roxbury neighborhood. His parents represented two immigrant traditions—German and Irish—but he grew up in Somerville, a working-class suburb where the line between hard work and crime was often blurred.
In 1943, just fourteen years old, he enlisted in the United States Marine Corps. Did he forge documents, or did recruiters turn a blind eye? We don’t know. What is certain is that the Massachusetts teenager landed on the battlefields of World War II while his peers were still sitting in school desks.
This early exposure to violence and military discipline shaped the man who would later lead one of New England’s most ruthless criminal organizations. The Marines teach loyalty to the Corps and to one’s brothers-in-arms. Winter took this lesson to heart, applying it in a very different context.
A New Mafia Boss
In postwar Boston, Winter became associated with James McLean, known as Buddy, the founder of the gang that would later bear Winter’s own name. He served as McLean’s closest associate and enforcer of the boss’s will.
The 1960s brought bloody wars between Irish gangs in the city. McLean was killed in 1965, and his legacy was taken over jointly by Winter and Joe McDonald.
For the next decade, the Winter Hill Gang controlled a significant portion of the criminal market in Somerville and the surrounding area. Gambling, extortion, loan sharking—these were the standard repertoire of organized crime at the time.
The gang also cooperated with the Italian mafia, which in the hierarchical world of American organized crime required both strength and diplomatic skill. Winter was adept at combining both.
The King’s Fall
The empire collapsed in 1979, when federal agents concluded an investigation into horse race-fixing. Winter, along with other gang members, was tried and sentenced to ten years in prison. He was replaced by James Bulger, known as Whitey—a man who would prove to be the craftiest of Boston’s gangsters.
Winter was released at the end of the 1980s and moved to St. Louis, far from his former turf. However, he maintained contact with old acquaintances, including James Mulvey, a friend of powerful Providence mafia boss Raymond Patriarca. It was Mulvey who delivered the information that changed everything—Whitey Bulger had been secretly cooperating with the FBI for years.
A Decade for Silence
In 1993, Winter was caught trafficking cocaine. Federal agents saw an opportunity and made him an offer—testify against Bulger in exchange for a lighter sentence.
For a man in his sixties, the prospect of another long prison term must have seemed grim. But Winter didn’t hesitate for a second. He told the agents that he knew all about Bulger’s role as an informant, but he himself would never be a rat. He chose prison.
He spent another nine years behind bars, finally being released in July 2002. After returning to Massachusetts, he worked humbly as a property manager in the small town of Millbury. In 2012, at the age of eighty-three, he was once again prosecuted for extortion, but was released on probation. He died in 2020, having lived over ninety years.
Autor
Margot Cleverly
Margot's journey into women's history began with a box of forgotten letters in a Cambridge archive – suffragettes whose voices had been silenced for over a century. Since then, she's been on a mission to uncover the stories history overlooked.
What she writes about: Queens who ruled from the shadows. Scientists whose male colleagues took credit. Revolutionaries who risked everything. But also ordinary women – those who survived wars, raised families through upheaval, and shaped their communities in ways no one bothered to record.
Margot turns historical figures into real people. She writes with warmth and detail, making centuries-old stories feel surprisingly relevant. Rigorous research meets accessible storytelling – no dusty academic jargon, just compelling narratives backed by solid facts.
When she's not writing, you'll find her in regional archives, collecting oral histories, or visiting sites connected to the women she writes about.