In the 1970s and '80s, FBI agent John Connolly used gangster Whitey Bulger as an informant and credited him with helping bring down the Mafia in Boston. However, Connolly also broke the law himself to protect Bulger. Connolly's actions were uncovered in the 1990s, and he was eventually convicted of racketeering and second-degree murder. The corrupt relationship between Connolly and Bulger is depicted in the 2015 film Black Mass.
John J. Connolly Jr. was born in Boston, Massachusetts, on August 1, 1940. For the first 12 years of his life, Connolly and his family resided in the Old Harbor housing project in South Boston, a neighborhood of mainly Irish families like their own.
While living in Old Harbor, Connolly befriended William "Billy" Bulger, who would become a successful politician. He also met James "Whitey" Bulger, Billy's older brother. Whitey, who was already known for his run-ins with the law, once saved a young Connolly from getting beaten up by other neighborhood kids.
Connolly got his undergraduate degree from Boston College. He then took classes at Suffolk Law School, though he didn't obtain a law degree, and found work as a high school teacher.
Connolly joined the FBI in 1968, and completed stints at offices in Baltimore, San Francisco and New York City before his 1972 arrest of Frank Salemme, a well-known Mafia figure, helped him get a transfer back to his hometown.
At the time, the Bureau had decreed that putting an end to the Mafia, or La Cosa Nostra, was a top priority. Drawing in part on their shared South Boston roots, in 1975 Connolly convinced Whitey, then a member of the Winter Hill Gang, to sign up as an informant against the Bureau's most wanted targets.
Connolly ended up as not only Whitey's handler, but also served as a contact for Whitey's close associate Stephen Flemmi (who'd been feeding tips to the FBI since the 1960s). Both Whitey and Flemmi were designated as top-echelon informants; Connolly would credit them with providing assistance that led to the arrests of figures like Gennaro Angiulo and members of the Patriarca family.
As the agent whose informants had proved so useful, Connolly received multiple commendations before retiring in 1990. He then headed to a well-paid corporate job.
During his years with the FBI, it appeared that Connolly was a dedicated and successful agent. However, he was so determined to keep Whitey and Flemmi on the streets, where they had access to information, that if another investigation came close to his informants, Connolly did his best to shield them.
Even as Whitey climbed to the top of Boston's criminal food chain — an ascent that should have made him a target, not an informant — Connolly remained committed to watching out for him. However, other law enforcement agencies didn't feel the same way. In 1994, the U.S. Attorney's Office put together racketeering charges against Whitey and others.
Thanks to a warning from the retired Connolly, Whitey was able to leave town, but Flemmi was arrested. As his case moved through the courts, it came to light that Whitey and Flemmi had been informants, and Flemmi declared that the FBI had promised him immunity for any crime short of murder.
At subsequent hearings in 1998, details about Connolly's dealings with Flemmi and Whitey were unveiled. A parade of witnesses — including Connolly's former supervisor, who'd been granted immunity for his own illegal actions — testified that Connolly had protected Whitey from investigations, engaged in bribery and regularly passed information to the gangster. When Connolly was called to testify, he invoked his right against self-incrimination.
Arrest and Convictions
At the end of 1999, Connolly was arrested. Convicted of racketeering, lying to an FBI agent and obstruction of justice in 2002, he was given a 10-year sentence.
In 2005, Connolly was indicted for the 1982 killing of John Callahan, the president of World Jai-Alai. These murder charges stemmed from the fact that Connolly had told Whitey that Callahan could testify about Whitey's involvement in yet another killing, prompting the gangster to engage a hit man to eliminate Callahan.
Connolly was convicted of second-degree murder in 2008 and received a sentence of 40 years. He appealed the conviction, which was overturned in 2014 (a panel of judges ruled that even though Connolly had been wearing his service weapon when he talked to Whitey, that did not qualify his crime for firearm involvement, and therefore the statute of limitations for second-degree murder had passed).
However, after the full appellate court heard the case, the judges ruled 6-4 in favor of upholding Connolly's conviction. For now, Connolly remains in prison in Florida, though he plans to appeal to the state's Supreme Court.
Many other agents and government officials have been accused of smoothing the path for Whitey and his associates, but only Connolly has been convicted. The FBI has altered its informant protocols, and some relatives of victims killed while Whitey was under FBI protection have received government compensation, but there has never been a full public accounting of exactly what went wrong during Connolly's time at the FBI.
Connolly married his first wife, Marianne Lockary, in 1970. The two separated in 1978 and got divorced four years later. Connolly's second wife was Elizabeth L. Moore, who had worked for the FBI as a stenographer. The couple wed in 1988 and had three children together.
Connolly's relationship with Whitey was a source of inspiration for Martin Scorsese's The Departed (2006). The book Black Mass (2000), which detailed Connolly and Whitey's interactions, resulted in a 2015 film of the same name. It stars Johnny Depp as Whitey Bulger and Joel Edgerton as Connolly.
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