On this day in 1934 we saw the birth of Stephen Flemmi, who was a close associate of organized crime figure Whitey Bulger. Flemmi became a government informant in the mid 1960’s and gave up a lot of intelligence during his relationship with the FBI.

He also provided information on mobster Kevin Weeks who was a longtime friend of both Bulger and Flemmi.

On this day in 1934, Stephen Joseph Flemmi was born in Boston, Massachusetts, into a world that would eventually draw him deep into the violent underworld of organised crime. Known on the streets as "The Rifleman" — a nickname earned during his time as a paratrooper in the Korean War — Flemmi would go on to become one of the most dangerous and ultimately most treacherous figures in the history of the New England mob scene.

Flemmi rose to prominence through his association with the Winter Hill Gang, the Irish-American crime outfit that dominated Boston's criminal landscape from the 1960s onward. His most notorious partnership was with James "Whitey" Bulger, with whom he ran a ruthless criminal enterprise involved in loan sharking, extortion, drug trafficking, and murder. The two men were virtually inseparable in their criminal operations for decades, building a reputation for brutality that kept competitors and potential informants in a state of constant fear.

What made Flemmi's story particularly remarkable — and deeply controversial — was his long-running relationship with the FBI. Beginning in the mid-1960s, Flemmi became a top-level informant for the Bureau, feeding intelligence to his corrupt handler, Agent John Connolly. This arrangement provided Flemmi and Bulger with an extraordinary degree of protection, allowing them to eliminate rivals and evade prosecution while ostensibly assisting federal investigations into the New England arm of the Italian-American Patriarca crime family. The extent of this corrupt relationship between organised crime figures and their FBI handlers would later become one of the most scandalous episodes in American law enforcement history.

Flemmi's reach extended to informing on a number of associates, including Kevin Weeks, a longtime enforcer and close confidant of both Bulger and Flemmi himself. Weeks had been a trusted figure within the Winter Hill Gang, making Flemmi's willingness to provide information on him yet another example of the cold-blooded pragmatism that defined his criminal character.

When the walls finally closed in, Flemmi pleaded guilty to ten murders and cooperated extensively with federal authorities in the prosecution of former FBI agent John Connolly, cementing his place as both a feared gangster and a confirmed informant. His legacy is one of betrayal layered upon betrayal — a career criminal whose ultimate impact was felt not only on the streets of Boston, but in the corridors of American law enforcement itself.