The Gang’s All Here

By Dick Lehr | Boston Magazine |

For the cast of characters who’ve starred in Boston’s longest-running drama, this month’s trial of crooked G-man John Connolly Jr. could be the final curtain call.


In the 1980s, when they were sitting atop the (under)world, corrupt FBI agents John Connolly Jr. and John Morris knew how to host a first-class dinner. They’d invite local crime bosses James “Whitey” Bulger and Stevie “the Rifleman” Flemmi, and enjoy good food, fine wine, gifts—and the intoxicating feeling that Boston was their oyster.

But this month, in Room 7-3 of the Miami–Dade County Courthouse, three of those four men will gather for what may be their Last Supper. The invitation came in the form of a 2005 indictment charging Connolly with first-degree murder and conspiracy to murder. He’s accused of setting in motion a hit back in 1982 by telling Bulger and Flemmi that an accountant in their grips might be cooperating with the feds. That accountant, John Callahan, originally from Boston, had been helping the Bulger gang skim millions from his sports-betting company in south Florida. After Connolly’s alleged tip-off, Callahan’s rotting corpse, riddled with bullets, was discovered in the trunk of a Cadillac at Miami International Airport.

Connolly, who’s already serving a 10-year federal prison sentence for protecting the Bulger gang from law enforcement, has denied wrongdoing during pretrial court sessions, at which the now-67-year-old prisoner appeared in handcuffs and a baggy red jumpsuit. (Long gone are the finely fitted suits that were his trademark.) He and his attorneys accuse prosecutors of building a shoddy case on the word of killers, liars, and thieves—in short, the guys Connolly used to pal around with. Still, as the agent at the center of the largest informant scandal in FBI history, Connolly doesn’t get much sympathy from his old colleagues at the bureau. Bob Fitzpatrick, a former Boston FBI supervisor who has testified in other trials related to Connolly’s misdeeds, says he “no longer presumes any innocence.”


The new charges could earn the crooked G-man a life sentence, which would be a fate worse than that of the actual triggerman. Johnny Martorano, who admitted to Callahan’s murder (and agreed to help the prosecution), served 12 years. These days he’s a free man, and is expected to testify at the trial.

He won’t be alone, either. Because the only witnesses to the alleged plot were criminal associates, the trial will host a reunion of thugs—a fitting setting, since they’ve all spent years ratting on one another.

Hostilities could run high: In addition to Martorano, Bulger sidekick Kevin Weeks will likely testify—as will Flemmi (who was put away for life thanks to testimony supplied by Weeks and Martorano). Even Morris, Connolly’s one-time boss who’s been so helpful to the feds that he’s never served prison time, will be on hand—emerging from exile to provide a bit of credibility (relatively speaking) to the witness roster. Of course, Connolly eliminated at least one potential participant: Bulger’s been on the run since 1995, when the agent encouraged him to bolt to elude federal indictment.

The unholy alliance between the FBI and the local mob has been dragging the cast of crooks into various courtrooms for years, but expect this trial to be the last occasion for a get-together. That is, unless Bulger is captured—and what a reunion that would make.