Betrayal: Whitey Bulger and the FBI Agent Who Fought to Bring Him Down by Jon Land, Robert Fitzpatrick
Authors: Jon Land, Robert Fitzpatrick
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flashy suits, had his hair professionally styled, and carried himself with a swagger and cockiness not at all in keeping with limited achievements that hardly made him the epitome of the modern-day FBI agent. Ironically, he reminded some veterans in the Boston office of a more polished version of Richie Castucci, acting “big” with not a lot to back it up.
But Connolly had a plan to change that.
Intimately acquainted with the exploits of Whitey Bulger from their common roots in Southie, the thirty-five-year-old Connolly set his sights on opening him as an informant, believing he could succeed where Paul Rico and Dennis Condon had failed. Indeed, because of his Southie ties, the young agent had legitimate street credentials—something the Bureau lacked in Boston at the time.
Bulger, though, resisted Connolly’s initial overture, held in the agent’s Plymouth overlooking Wallaston Beach, and that may have proven fortuitous for the ambitious Connolly, since there had been a change in tenor and tolerance expressed by FBIHQ. In a warning about informants, U.S. attorneys at a national conference in 1974 expressed a “belief” that the FBI had become “overly protective” of informants and made “efforts so that informants are not prosecuted so that they continue to provide intelligence information.” With both Rico and Condon taking that as their cue to leave the Bureau, the Boston office escaped recrimination and business pretty much returned to normal, only with new players, led by John Connolly, in place. History was about to repeat itself, with Whitey effectively becoming a new incarnation of Joseph Barboza, the lessons of the past not being heeded whatsoever.
Connolly’s subsequent meetings with Bulger proved much more productive precisely because Bulger saw in the ambitious agent a new means to help him achieve his own nefarious ends. Among other things, he was facing a major rift with the Angiulos, the local Italian mob family, over the lucrative placement of vending machines in various area establishments. Since Connolly’s only reason for wanting his help was to bring down those very Angiulos, Bulger saw a way to enlist the agent as an unwitting accomplice in solving his current dilemma. Bulger brought along his right-hand man Stephen “the Rifleman” Flemmi, and Connolly saw his opportunity to find the same glory achieved by Rico and Condon while avoiding the excesses that led to their ultimate downfalls at the hands of Barboza.
At the outset anyway, he was not disappointed. In 1976, Stephen Flemmi and Bulger provided information that allowed Connolly to turn a co-conspirator into a cooperating witness, identifying Joe Russo as the killer of none other than Joseph Barboza, who was gunned down in San Francisco just days after his release from prison. In a typical execution-style murder, Barboza was clipped by Russo and his gang from inside a Ford Econoline van that pulled up next to Barboza’s car and pumped him full of bullets. The van was abandoned alongside Barboza, who was left lying in a pool of blood, eerily reminiscent of victims he had left behind.
Having proven himself to his handlers, Bulger wasted no time in taking over the Winter Hill Gang in the wake of gang leader Howie Winter’s incarceration. The fact that the Italian mob remained the Bureau’s number one priority gave Bulger carte blanche to run the Irish mob however he saw fit. In fact, the more powerful he could become, the more power he could exert on the Bureau’s behalf. At least that was the thinking at the time. Connolly and his supervisor, John Morris, and Bulger and Flemmi shared one thing in common: ambition. But that was enough to drive their relationship forward and sustain it so long as each was helping to promote the success of the other.
Boston watched as the Winter Hill Gang under Bulger and Flemmi consolidated its vicious hold on the city’s rackets, thanks in large part to the federal arrests and subsequent
But Connolly had a plan to change that.
Intimately acquainted with the exploits of Whitey Bulger from their common roots in Southie, the thirty-five-year-old Connolly set his sights on opening him as an informant, believing he could succeed where Paul Rico and Dennis Condon had failed. Indeed, because of his Southie ties, the young agent had legitimate street credentials—something the Bureau lacked in Boston at the time.
Bulger, though, resisted Connolly’s initial overture, held in the agent’s Plymouth overlooking Wallaston Beach, and that may have proven fortuitous for the ambitious Connolly, since there had been a change in tenor and tolerance expressed by FBIHQ. In a warning about informants, U.S. attorneys at a national conference in 1974 expressed a “belief” that the FBI had become “overly protective” of informants and made “efforts so that informants are not prosecuted so that they continue to provide intelligence information.” With both Rico and Condon taking that as their cue to leave the Bureau, the Boston office escaped recrimination and business pretty much returned to normal, only with new players, led by John Connolly, in place. History was about to repeat itself, with Whitey effectively becoming a new incarnation of Joseph Barboza, the lessons of the past not being heeded whatsoever.
Connolly’s subsequent meetings with Bulger proved much more productive precisely because Bulger saw in the ambitious agent a new means to help him achieve his own nefarious ends. Among other things, he was facing a major rift with the Angiulos, the local Italian mob family, over the lucrative placement of vending machines in various area establishments. Since Connolly’s only reason for wanting his help was to bring down those very Angiulos, Bulger saw a way to enlist the agent as an unwitting accomplice in solving his current dilemma. Bulger brought along his right-hand man Stephen “the Rifleman” Flemmi, and Connolly saw his opportunity to find the same glory achieved by Rico and Condon while avoiding the excesses that led to their ultimate downfalls at the hands of Barboza.
At the outset anyway, he was not disappointed. In 1976, Stephen Flemmi and Bulger provided information that allowed Connolly to turn a co-conspirator into a cooperating witness, identifying Joe Russo as the killer of none other than Joseph Barboza, who was gunned down in San Francisco just days after his release from prison. In a typical execution-style murder, Barboza was clipped by Russo and his gang from inside a Ford Econoline van that pulled up next to Barboza’s car and pumped him full of bullets. The van was abandoned alongside Barboza, who was left lying in a pool of blood, eerily reminiscent of victims he had left behind.
Having proven himself to his handlers, Bulger wasted no time in taking over the Winter Hill Gang in the wake of gang leader Howie Winter’s incarceration. The fact that the Italian mob remained the Bureau’s number one priority gave Bulger carte blanche to run the Irish mob however he saw fit. In fact, the more powerful he could become, the more power he could exert on the Bureau’s behalf. At least that was the thinking at the time. Connolly and his supervisor, John Morris, and Bulger and Flemmi shared one thing in common: ambition. But that was enough to drive their relationship forward and sustain it so long as each was helping to promote the success of the other.
Boston watched as the Winter Hill Gang under Bulger and Flemmi consolidated its vicious hold on the city’s rackets, thanks in large part to the federal arrests and subsequent
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