Crime & Safety

Bulger's Partner In Crime Seeking Medical Release From Prison

Stephen "The Rifleman" Flemmi, who has been in prison for 26 years, is seeking compassionate release as his health deteriorates.

Stephen "The Rifleman" Flemmi​ in a 2008 file photo. Flemmi is seeking compassionate release from prison, where he is serving a life sentence for his role in multiple gangland killings.
Stephen "The Rifleman" Flemmi​ in a 2008 file photo. Flemmi is seeking compassionate release from prison, where he is serving a life sentence for his role in multiple gangland killings. (AP Photo/J. Pat Carter, File)

BOSTON — Stephen "The Rifleman" Flemmi, the confessed killer who cut a deal and testified against James "White Bulger" to avoid the death penalty, is set to go before a parole board in Florida on Aug. 18.

Flemmi, 87, has served 26 years of a life sentence at an undisclosed location. According to court documents filed in Oklahoma, Flemmi is seeking compassionate release. In a January letter to the federal judge who sentenced him in 2004 in the 1981 killing of Tulsa businessman Roger Wheeler, Flemmi said his age and underlying health conditions "make it highly likely that if I contract COVID-19 that I will suffer an extremely poor outcome."

The Boston Globe was the first to report that Flemmi was seeking compassionate release. The Boston Herald confirmed the date of the hearing with the widow of one of Flemmi's victims.

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"He’s talking about compassion?" Mary Callahan, whose husband was killed in 1982, told the Herald. "I didn’t see him having any compassion for his victims."

Flemmi, who is serving multiple state and federal sentences, has been held in a confidential location in the federal prison system since agreeing to testify against his former crime partner Bulger. Bulger was killed in Oct. 2018 after a prison transfer while he was serving a life sentence. Last year, Bulger's family filed a wrongful death lawsuit against the federal Bureau of Prisons.

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In February, the Florida Commission on Offender Review voted 2-1 to grant release former FBI agent John Connolly. Connolly, who is terminally ill, was Flemmi and Bulger's FBI handler and tipped the duo off to pending indictments in 1995. Bulger went on the run for more than 15 years, while Flemmi cut a deal with federal prosecutors

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