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Boston gangster Stephen ‘The Rifleman’ Flemmi cites health concerns in bid for release from prison

Stephen "The Rifleman" Flemmi, a jailed Boston mob leader, testifies Monday, Sept. 22, 2008, in a Miami courtroom in the murder trial of former FBI agent John Connolly. J. Pat Carter / AP, File


BOSTON (AP) — A notorious New England gangster locked up for life for a slew of killings says his health is in peril behind bars and wants out.

Stephen “The Rifleman” Flemmi wrote in a letter to an Oklahoma state court judge that prison medical staff say his age and underlying health conditions make it “highly likely” that he will “suffer an extremely poor outcome” if he gets the coronavirus, The Boston Globe reported.

Flemmi is serving life sentences for convictions in federal court as well as Florida and Oklahoma state courts. Even if federal officials approve his bid for compassionate release, he would remain locked up unless Oklahoma and Florida officials also agree to release him. Miami-Dade prosecutor Michael Von Zamft said there has been no request to release Flemmi from his Florida sentence.

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Flemmi’s son, William St. Croix, told the Globe that his father is trying to use the coronavirus to get out, but is actually healthy. Flemmi admitted that he watched as his partner, James “Whitey” Bulger, strangled St. Croix’s sister, Deborah Hussey, in 1985.

“I’ve never received a letter from him asking for forgiveness,” St. Croix said. “He didn’t just kill her, he tortured her … and he wants compassion? I think people are going to have a hard time with that.”

Flemmi was a close partner of Bulger, the leader of the Winter Hill Gang, which terrorized Bostonians for decades. Flemmi testified against Bulger during his 2013 trial.

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Flemmi also took the stand in 2018 to testify against another old friend, former New England Mafia Boss Francis “Cadillac Frank” Salemme, who was convicted in the 1993 killing a nightclub owner.

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