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Stephen 'The Rifleman' Flemmi
Stephen "The Rifleman" Flemmi

Stephen 'The Rifleman' Flemmi

A Roxbury native, Stephen J. Flemmi got his nickname during the Korean War, when he was an uncanny marksman in the Army. In the 1960s, Flemmi developed close ties to both the Irish and Italian mobs, befriending Mafia boss Francis "Cadillac Frank" Salemme and earning a reputation as a cold-blooded operative. He later joined up with Somerville's Winter Hill gang, where he forged a close partnership with "Whitey" Bulger. Flemmi served as Bulger's front man, collecting money from bookies and inspiring fear in those who didn't pay their debts on time. He began informing for the FBI in the 1960s, a decade before his sidekick, Bulger.

Flemmi was arrested in 1995 on charges of racketeering and extortion, but fought the charges on grounds that the FBI had granted him and Bulger permission to commit certain crimes short of murder while they worked as informants. The ensuing court hearings dredged up some of the Boston FBI’s darkest secrets, including revelations of agents accepting payoffs and leaking information to help protect Flemmi and Bulger from prosecution. A judge ultimately ruled that the gangsters had received no promise of immunity, and Flemmi was sentenced in August 2001 to 10 years in prison for extortion and money laundering as part of a plea agreement with prosecutors. However, the revelation that he was an informant prompted his old cohorts to turn on him, the discovery of secret mob graves and new charges of murder against him.

Under a deal that spared him the death penalty, Flemmi pleaded guilty in 2004 to 10 murders -- including one in Florida and one in Oklahoma -- in exchange for a life sentence and began cooperating with the government. He alleged that he and Bulger had paid their former handler, John J. Connolly Jr., $200,000 while they were working as informants, gave cash and gifts to other agents and police officers, and offered details of corruption and murder. His cooperation led to Connolly's indictment in Florida on murder charges.

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