Stephen “The Rifleman” Flemmi said he packed his bags after a corrupt FBI agent warned him and his partner, James “Whitey” Bulger, to flee just before their 1995 racketeering indictment.
But Flemmi hung around Boston too long and was arrested, while Bulger disappeared for more than 16 years until his capture two years ago in Santa Monica, Calif.
On Thursday, the aging gangsters who allegedly ran a criminal enterprise that rivaled the Mafia while being protected by the FBI because they were informants, will come face to face for the first time in decades when Flemmi takes the stand at Bulger’s racketeering trial in US District Court in Boston.
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“He is arguably the most critical witness in the case,” said Boston defense attorney Martin G. Weinberg. “He is the single witness who can either adopt or contradict Bulger’s claims that he was not guilty of certain murders and that he was not an informant.”
Bulger, 83, is charged in a sweeping federal racketeering indictment with participating in 19 murders in the 1970s and 1980s, extortion, money laundering, and stockpiling guns.
In letters to a friend from jail last year that were shared with the Globe, Bulger said the two things he most wants to refute are that he was an informant and that he killed two women, who are among his 19 alleged victims. Flemmi is a key government witness on those points.
Flemmi, 79, is serving a life sentence for 10 murders and has implicated Bulger in all of them, claiming he watched as Bulger strangled Debra Davis and Deborah Hussey on separate occasions in the 1980s. He is also expected to offer jurors a firsthand account of the corrupt and cozy relationship he and Bulger shared with FBI agents and of leaked information he says prompted them to kill other informants.
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“Flemmi was a major, major player, a very much feared guy,” said Boston attorney Anthony Cardinale, who was instrumental in exposing the corrupt relationship between Bulger and Flemmi and the FBI. “[Jurors] are going to be disgusted by him, but they are going to believe him. He’ll be a good witness because every meeting they had with the FBI he was there. They didn’t do it singularly. They did it together.”
Cardinale said Flemmi also may have more credibility with jurors because, unlike other former Bulger associates, who participated in murders and are free today because of deals they cut with prosecutors, Flemmi will spend the rest of his life behind bars.
“The bottom line here is a guy who is going to say: ‘I’m not lying. . . . I will die in jail, this is the truth of what happened here,’ ’’ Cardinale said.
In 1997, Flemmi urged a judge to dismiss the racketeering case against him, claiming the FBI had given him and Bulger permission to commit crimes, with the caveat they not kill anyone, because they were informants against the bureau’s number one target, the Mafia.
US District Judge Mark L. Wolf refused to dismiss the case, but held yearlong hearings exposing the relationship between Bulger, Flemmi, and the FBI. The revelations and concerns that Flemmi would implicate them in new crimes prompted Flemmi’s former associates to cut plea deals. They implicated Bulger and Flemmi in unsolved slayings that led to a sweeping new indictment in 2000, the one Bulger is facing at trial.
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Flemmi pleaded guilty in 2003 to 10 murders and admitted his role in 10 others, in a deal that spared him the death penalty for slayings in Oklahoma and Florida. Since then, he has testified in criminal and civil trials.
Flemmi was recruited as an FBI informant in 1964, then closed in 1969 when he was a fugitive facing charges that he planted a car bomb that wounded a Boston lawyer. When the charges were dismissed in 1974 because a witness recanted, Flemmi returned to Boston and teamed up with Bulger and other members of the Winter Hill Gang.
In prior testimony, Flemmi said he and Bulger were kindred spirits, physical fitness buffs who liked to work out, rarely drank alcohol, and were well read.
Flemmi said Bulger was already an FBI informant in 1975 when he sent Flemmi to meet his handler, agent John J. Connolly Jr., marking the beginning of 15-year relationship in which all three regularly met to exchange information. Flemmi claimed that Connolly became like another member of the gang and pocketed between $235,000 and $250,000 in payoffs from him and Bulger.
Bulger’s lawyers told jurors during opening statements last month that Connolly fabricated Bulger’s hefty informant file to cover up the fact that he was routinely meeting Bulger to leak information to him and collect cash.
Flemmi also claims Bulger was the driving force behind the 1981 murder of Davis, 26, who was Flemmi’s girlfriend, and the 1985 murder of Hussey, also 26, who was the daughter of Flemmi’s other longtime girlfriend, Marion Hussey. Flemmi admitted that he began molesting Deborah Hussey when she was a teenager.
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Testifying in a 2009 wrongful death suit brought against the government by the women’s mothers, Flemmi claimed he lured the women to homes in South Boston, then watched as Bulger strangled them.
Attorney Weinberg said Flemmi has a lot of baggage, but it will be a challenge for Bulger’s lawyers to attack Flemmi’s credibility while delving into crimes that allegedly involved Bulger.
“The challenge for the cross-examiner is always to insulate your own client from the baggage,” Weinberg said.
Murphy can be reached at shmurphy@globe.com. Follow her on Twitter @shelleymurph.