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John J. Connolly Jr.
John J. Connolly Jr.
Callahan murder saga
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Callahan murder saga

John J. Connolly Jr.

John J. Connolly Jr. grew up in a South Boston housing project a few doors down from the Bulger family. He formed a fast friendship with Billy Bulger, and admired Billy's mysterious and mischievious older brother, "Whitey." By the mid-1970s, Connolly was an up-and-coming FBI agent eager to make his mark in the agency's Boston office. Bulger, meanwhile, was climbing the ranks of the city's underworld and looking to expand his power. In 1975, the old Southie acquaintances formed a partnership from which both would benefit.

Connolly persuaded Bulger to sign on as an informant, a coup that soon made Connolly a star within the FBI. The agency valued high-level snitches, and in the Boston office there were none more highly placed than "Whitey" Bulger. With the help of tips from Bulger and his partner, Stephen Flemmi, the FBI began dismantling the Irish mob's chief rivals, the Italian Mafia, paving the way for Bulger's ascendancy.

In exchange for the valuable tips Bulger provided, Connolly and his fellow agents allegedly helped the gangster elude the law by tipping him off to investigations and protecting him from prosecution. Under this cloak of protection, Flemmi and Bulger built a drug and racketeering empire while getting away with murder.

Connolly retired from the FBI in 1990 after 22 years, accepting a highly paid job with Boston Edison. With Connolly out of the picture, the FBI dropped Bulger and Flemmi as informants and began targeting them, eventually handing down federal racketeering and extortion charges against the pair in 1995.

The dark details of the FBI's secret pact with the Mob emerged in 1998, during a year-long series of federal court hearings into Flemmi's request to dismiss racketeering charges against him. The following year, Connolly was indicted on federal charges. In 2002, a jury convicted him of federal racketeering, obstruction of justice and lying to an FBI agent. Jurors found that he tipped Bulger and Flemmi to investigations, alerted them to flee just before their 1995 racketeering indictment, and lied to an FBI agent about his efforts to help Flemmi beat the charges against him. However, the jury found prosecutors failed to prove the most serious charges against Connolly: that he leaked information to Bulger and Flemmi that prompted them to kill three men. Connolly was sentenced to 10 years in prison.

In May 2005, Connolly was indicted on state murder charges in Florida, which carry a life prison term. He was accused of leaking information to Bulger and Flemmi in 1982 that prompted them to kill a Boston business consultant, John B. Callahan, who was a potential witness against them. He proclaims his innocence. Connolly is serving 40 years after being convicted in 2008 of second-degree murder. In March 2011, Connolly lost his appeal to have that conviction overturned.

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