It was the classic tale of the outlaw and the lawman. James Whitey Bulger, the charismatic street thug who went on to lead the notorious and murderous Winter Hill gang, and John Connolly, dapper and college-educated, who went on to become a highly commended FBI agent.
They grew up in the same Boston housing project, and their lives intersected over the years, until they collided — sending one on the lam and the other facing corruption charges.
Connolly was released from a Florida prison this week after serving 20 years on charges of racketeering, obstruction of justice and murder — all associated with his cozy relationship with Bulger. Florida officials gave Connolly, now 80, compassionate release, citing his age, a terminal cancer diagnosis, diabetes and other health issues. The family of his murder victim, John Callahan, has given his release their blessing.
I interviewed Connolly in 1998, before his trial, and described Whitey Bulger's life on the run.
"Well, apparently, it's hard to find him. He's not your average criminal. He's very bright. He's very disciplined. And I would think that he has the discipline to ... lay low," Connolly told me, adding that he didn't think anyone in the FBI knew whether or not Bulger was still in the U.S.
Watch the 1998 interview:
A few years after that interview, Connolly was convicted of racketeering and obstruction of justice. Prosecutors charged that it was Connolly himself who alerted Bulger that the FBI was coming after him, after the Boston Globe first reported in 1988 that Connolly had recruited both Bulger and Stephen "The Rifleman" Flemmi as FBI informants. Connolly was later convicted of murder, having once again tipped Bulger that businessman John Callahan was about to tie the mobster to another murder. That cost Callahan his life.
While he was serving his time, Connolly and I communicated a half a dozen times by letter. He offered his condolences on the passing of my dad in 2011, and he spoke of his Catholic faith and reaching a middle ground with the church over “end of life issues.”
And of course, he spoke of his innocence, saying he had “irrefutable evidence" that he was framed by mobster Francis "Cadillac" Salemme. He said Salemme failed to mention eight other murders he committed while working a deal with prosecutors.
Connolly’s letters could be dense, filled with minute detail about his case and specifics about how prosecutors withheld evidence that would have exonerated him. As an FBI agent, Connolly had cultivated a polished style with the press; he wooed and cajoled those who covered his beat. So it was no surprise that he wrote in his letters of those who had betrayed him — and those who were doing excellent work on his behalf.
He has always maintained that he was the fall guy, taking the blame for an agency corrupt from the top down. He spent much of his time in prison preparing for hearings and collecting evidence he said was “highly exculpatory.”
Back in 1998, he told me prosecutors were out to get him, regardless.
"There's one reason why they don't want to give me immunity. They are afraid of the truth," he said.