August 16, 2021 – Famed Boston underworld figure Stevie (The Rifleman) Flemmi will see the parole board this week down in Florida, hoping for relief from a life sentence for taking part in multiple gangland murders. The 87-year old Flemmi was partners with notorious Boston Irish mob boss James (Whitey) Bulger from the 1970s until the mid-1990s and has been in prison going on three decades. He is seeking a compassionate release from the board on Wednesday.
Flemmi has cooperated with the federal government in building murder cases against disgraced FBI agent John Connolly and New England mafia don Francis (Cadillac Frank) Salemme. Flemmi was a star witness at both Connolly’s 2008 trial and Salemme’s 2018 trial.
Together, Flemmi and Bulger took control of Boston’s Winter Hill Gang, a mostly Irish crime family operating out of South Boston and Sommerville in the mid-1970s. Flemmi got the nickname “Rifleman” because he was a sniper for the U.S. Marines in the Korean War. Because of his Italian heritage, Flemmi was a go-between for the Irish and Italian mob factions in New England.
Bulger is one of the most infamous American crime lords in recent memory. His longtime cooperation with the government and confidential informant status throughout his reign of terror in South Boston was revealed by The Boston Globe and sent shockwaves through the underworld and FBI. Flemmi was also a CI, informing on his mob rivals along with his gangland buddy Bulger, who was beaten to death behind behind bars by fellow inmates in a West Virginia federal penitentiary in 2018.
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