Connolly was an FBI handler of James "Whitey" Bulger, head of Boston's Winter Hill mob, and Stephen "the Rifleman" Flemmi, Bulger's enforcer. For years, Bulger, Flemmi, and the Winter Hill gang enjoyed protected status as federal "informants," while they conducted their violent criminal activities.
Connolly was the inspiration for the character played by Matt Damon in the 2006 Oscar-winning Martin Scorsese film, The Departed. The film also featured Jack Nicholson, playing the Bulger character, and Leonardo diCaprio as an undercover Boston police officer.
Connolly, according to court testimony, took over $235,000 in bribes from the mob and repeatedly provided tips to Bulger's gang, warning them of impending police raids and investigations that were getting close to them. He also informed them of possible "rats" in their midst who needed to be eliminated. According to prosecutors, at least three informants were killed because of Connolly's tip-offs. One of those murdered was former World Jai-Alai president John Callahan, whom Bulger and Flemmi were afraid might implicate them in other slayings.
Flemmi, who was arrested in 1995 and is serving multiple life sentences, testified against Connolly for the prosecution. Whitey Bulger escaped the same 1995 dragnet and remains a fugitive. Connolly, who will be sentenced on December 4, is expected to receive life in prison.