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Stephen “The Rifleman” Flemmi cut a deal with the government decades ago that spared him the death penalty for his role in 10 murders in Massachusetts, Florida, and Oklahoma. The longtime FBI informant described the slayings in gruesome detail while testifying against his partner in crime, James “Whitey” Bulger, and a corrupt FBI agent.

Now, Flemmi, 87, one of New England’s most infamous organized crime figures, is seeking compassionate release after serving 26 years of a life sentence in prison, according to court documents filed in Oklahoma.

In a January letter to an Oklahoma state judge, Flemmi, who in 2004 pleaded guilty to the 1981 killing of Tulsa businessman Roger Wheeler, wrote that he had been advised by prison medical staff that his age and underlying health conditions “make it highly likely that if I contract COVID-19 that I will suffer an extremely poor outcome.”

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Flemmi, who is serving multiple state and federal sentences at an undisclosed federal prison, wrote that he had “cooperated with the Federal Government in a series of cases against extremely violent individuals with a long and storied history of retribution against cooperators and as a result I am being housed in a confidential location with the [US Bureau of Prisons].”

He urged the judge to appoint a lawyer to represent him “with regard to this life-threatening issue.” There has been no ruling on Flemmi’s request, according to the docket, and the Tulsa district attorney has yet to weigh in on the matter.

Flemmi’s son William St. Croix confirmed his father has also sought release from the US Bureau of Prisons.

Flemmi faces many legal hurdles in his bid for freedom, which has not drawn public notice because his motion in Oklahoma is filed in a closed murder case in Tulsa County district court brought against him 20 years ago. Even if the Bureau of Prisons were to grant Flemmi compassionate release, he would not go free unless Oklahoma and Florida officials also approve his release from life sentences imposed in those states, according to authorities.

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Flemmi was sentenced to life in prison by a Miami judge in 2004 for the 1982 slaying of Boston businessman John B. Callahan in Florida. Under state law at the time of the slaying, he must serve a minimum of 25 years in prison before he is eligible for parole.

“If Flemmi was granted release from his federal sentence, he would still need to complete his Florida sentence should Florida not also grant him release,” said Angela Meredith, a spokeswoman for the Florida Commission on Offender Review.

In February, the commission granted conditional medical release to former FBI agent John J. Connolly Jr., who was serving a 40-year sentence for helping Flemmi and Bulger orchestrate Callahan’s murder to prevent him from implicating them in the slaying of Wheeler and two other men. Neither prosecutors nor Callahan’s family opposed Connolly’s release after doctors said he is suffering from cancer and diabetes and likely to die within a year.

Miami-Dade prosecutor Michael Von Zamft said Florida officials have not received any requests related to Flemmi’s release and would have to review his claims and medical condition before making any recommendations.

“All I know is he pled guilty and he got a sentence that he agreed to,” said Von Zamft, who prosecuted Flemmi. “It seemed right to me then and it seems right to me now.”

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Relatives of Flemmi’s victims said they were unaware he is seeking compassionate release and were furious at the prospect he could walk free.

“I think the government should be notifying all the families as to what’s going on,” said Steve Davis, whose 26-year-old sister, Debra Davis, was killed by Flemmi, and allegedly Bulger, in 1981. “If he was to die right now, maybe I’d be at ease with it. To know he’s still breathing and out there ... I think he should die right now, die in prison.”

St. Croix said his father is healthy and trying to “exploit a loophole” by raising concerns about the coronavirus to get released.

“I’ve never received a letter from him asking for forgiveness,” said St. Croix, who cooperated with authorities after his father confessed to him in 2000 that he and Bulger killed his 26-year-old sister, Deborah Hussey, in 1985. “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 testified that he lured Hussey to a South Boston home and watched Bulger strangle her. Hussey was a toddler when Flemmi moved in with her mother; he raised her with St. Croix and two other children he had with her mother. She was killed shortly after she told her mother that Flemmi began molesting her as a teenager, according to court testimony.

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St. Croix said he’s estranged from his father, but a relative who has been in contact with Flemmi told him that his father has received the COVID-19 vaccination, is in “good shape,” and spends his time in prison painting and making toy soldiers. One of his paintings is a replica of Rembrandt’s “Storm on the Sea of Galilee,” one of the masterpieces stolen from the Isabella Stewart Gardner Museum in Boston in 1990, and another is of legendary NFL quarterback Tom Brady.

Stephen Flemmi's recreation of Rembrandt's "Storm on the Sea of Galilee," one of the pieces stolen from the Isabella Stewart Gardner Museum in 1990.
Stephen Flemmi's recreation of Rembrandt's "Storm on the Sea of Galilee," one of the pieces stolen from the Isabella Stewart Gardner Museum in 1990.William St. Croix

In his letter to the Oklahoma judge, Flemmi said he has not received any disciplinary reports during his incarceration and included a prison evaluation that determined he was at low risk of reoffending if released. He also included military records that show he served as a paratrooper with the Army during the Korean War and received an honorable discharge and is entitled to $1,334 in monthly benefits because of a service-related disability.

“I don’t know how someone can redeem themselves after doing all the vile things he’s done,” St. Croix said. “Even if he was redeemed, I would still always live with the fear that if he’s out that he might harm my children.”

The Bureau of Prisons did not respond to repeated inquiries about Flemmi’s request, a process that is handled internally by the agency and shrouded in secrecy. Federal inmates seeking compassionate release make their requests to the warden at the prison where they are housed. If a warden approves, it’s forwarded to the Bureau of Prisons’ central office for a final decision. If a warden rejects a request, the prisoner may petition a federal judge for a sentence reduction.

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A spokeswoman for the US attorney’s office in Massachusetts, which prosecuted Flemmi and then used him as a cooperating witness, declined to say whether prosecutors support or oppose his release.

Flemmi, who became an FBI informant in the 1960s, was indicted in 1995 with Bulger and others in a sweeping federal racketeering case. Bulger fled and remained a fugitive for more than 16 years, while Flemmi has been incarcerated since then.

In 2004, he pleaded guilty in federal court in Boston to 10 murders in the 1970s and 1980s and an array of other crimes, including the extortion of drug dealers, bookmakers, and legitimate business people. He admitted that he participated in about 50 killings dating to Boston’s gang wars of the 1960s. He admitted pulling the teeth of victims, before burying them in unmarked graves, to hinder identification in an era before DNA testing evolved.

As part of his plea agreement, prosecutors in Florida and Oklahoma agreed to recommend that he serve his state life sentences in federal prison, running concurrently with his federal life sentence.

Flemmi’s testimony exposed FBI corruption, resulting in Connolly’s murder indictment in Florida. He described his involvement in gruesome murders in court, including in the trials of Connolly, Bulger, and former New England Mafia boss Francis “Cadillac Frank” Salemme.

In Oklahoma in 2004, Flemmi pleaded guilty to the slaying of Wheeler, the chairman of Telex Corp. and owner of World Jai Alai, who was gunned down outside a Tulsa country club in 1981. Flemmi said Wheeler was killed because he suspected Bulger’s gang of skimming from his company. Flemmi implicated retired FBI agent, H. Paul Rico, who was charged with plotting with the gangsters to kill Wheeler but died before trial.

Wheeler’s son, David, said he was outraged by Connolly’s medical release earlier this year because “he betrayed everything the FBI is supposed to stand for.” But he was unaware that Flemmi was seeking compassionate release until he was contacted by the Globe and said he wants to know more about the circumstances before deciding whether to support or oppose it. He said his family didn’t learn the truth about his father’s slaying until Flemmi and another cooperating witness exposed FBI corruption.

“What serves the interest of the public is to know just how bad the corruption was,” Wheeler said. “At this point, we still have no idea how bad it was.”


Shelley Murphy can be reached at shelley.murphy@globe.com. Follow her on Twitter @shelleymurph.