For 20 years, FBI agent John Connolly covertly worked with gangster Whitey Bulger, offering him protection from prosecution in exchange for information about rival mobs in the city.
Thomas Landers/The Boston Globe via Getty ImagesFBI agent John Connolly in 1987.
Beginning in the 1970s, Boston FBI agent John Connolly formed an unexpected relationship that would help him bring down numerous high-level criminals over the next 15 years. He teamed up with none other than Whitey Bulger, the leader of the city’s Winter Hill Gang, to receive inside information on Bulger’s rivals in the Mafia.
In exchange, Connolly reportedly protected Bulger for nearly two decades by tipping him off to any investigations against him. This allowed Bulger to successfully build his criminal empire, rising to the top of Boston’s Irish Mob.
Their illicit partnership lasted until at least 1990, when Connolly retired from the FBI. However, it wasn’t revealed until 1998. Then, Connolly faced federal charges of racketeering, obstruction of justice, and even murder for his association with Bulger — and his indirect role in the death of a Boston businessman.
This is the story of John Connolly, the disgraced FBI agent who partnered with one of Boston’s most notorious criminals in an attempt to bolster his own career.
How John Connolly Became Involved With Mob Boss Whitey Bulger
John Joseph Connolly Jr. was born in Boston on August 1, 1940. His father worked for Gillette, and his mother was a housewife. The family was poor, and Connolly grew up in the Old Harbor Housing Project. Just a few doors down lived the Bulger family.
Facebook/Dirty Old BostonThe Old Harbor Housing Project in 1940.
According to Boston.com, Connolly was good friends with Billy Bulger, the younger brother of future Mob boss James “Whitey” Bulger. While Connolly and the elder Bulger didn’t cross paths often due to their age difference (Bulger was 11 years Connolly’s senior), they did know of each other.
The Boston Globe reported that Whitey Bulger once chased away eight-year-old Connolly’s bullies during a fight over a ball. At the time, 19-year-old Bulger was already notorious for leading the Mercer Street Gang.
Connolly’s family moved away from the housing project when he was 12 years old, and he likely didn’t see Bulger again until the 1970s. Until then, they led vastly different lives.
Wikimedia CommonsOne of Whitey Bulger’s earliest mugshots in 1947.
Bulger continued to rise through the ranks in Boston’s criminal underworld, and he soon moved up from the Mercer Street Gang to the much larger — and deadlier — Winter Hill Gang. Meanwhile, Connolly attended Boston College, took law school classes, and secured a job as an FBI agent at the Boston field office in 1973. Two years later, he would cross paths with his old neighbor Whitey Bulger once again.
The Unexpected Partnership Between An FBI Agent And A Crime Boss
In 1975, John Connolly reportedly persuaded Whitey Bulger to become an informant. The deal was simple: Bulger would give Connolly information on rival gang members, and Connolly would protect Bulger from prosecution for his own illegal activities. For more than a decade, the plan worked perfectly.
With tips he received from Bulger, according to the Miami New Times, Connolly was able to take down major figures like Gennaro Angiulo, the head of Boston’s Italian Mafia.
He also helped dismantle the Patriarca crime family. As former FBI agent Joseph D. Pistone wrote in his book The Ceremony: “The reign of the Patriarca Family is virtually ended. A substantial amount of the credit for the demise of that mob Family must be given to one man, Special Agent John Connolly.”
Wikimedia CommonsWhitey Bulger and his crime partner Stephen Flemmi in the 1980s.
Bulger benefitted from the deal as much as Connolly did. Getting his enemies off the streets meant less competition when it came to things like trafficking illicit substances. Bulger and his partner in crime, Stephen Flemmi, were able to build up a drug empire that made the Winter Hill Gang one of the most powerful factions of the Boston Mob. With the protection of Connolly, Bulger quite literally got away with murder.
In 1990, John Connolly retired after 22 years as an FBI agent. Bulger was dropped as an informant, and by 1995, the FBI had charged him with racketeering and extortion. The symbiotic relationship between the criminal and law enforcement had come to a bitter end — and Bulger wasn’t the only one who ultimately faced justice.
John Connolly’s Arrest, Trial, And Imprisonment
By 1998, details about John Connolly’s secret partnership with Whitey Bulger had started to emerge. He was indicted on his first federal charges the following year, and in 2002, he was convicted of racketeering, obstruction of justice, and lying to an FBI agent.
These charges stemmed from Connolly tipping off Bulger and Flemmi before they were charged in 1995, telling them to flee. He then lied to an FBI agent about his involvement. He was convicted in 2002 and sentenced to 10 years in prison.
Twitter/@picturebostonJohn Connolly leaving a federal courthouse in Boston in 2002.
Connolly’s most serious charges, however, came from another incident. In 2008, he was convicted of second-degree murder. According to the Boston Herald, Connolly had once leaked information to Bulger that led the mobster to have a man killed.
That man was John Callahan, the former president of World Jai Alai. Bulger had previously had another World Jai Alai executive killed, and Callahan had information that could implicate him in the murder. Connolly reportedly leaked this tip to Bulger, causing Bulger to order a hit on Callahan to protect himself.
John Connolly was sentenced to an additional 40 years in prison for the crime. He remained behind bars until 2021 when he was granted medical release due to his failing health. Meanwhile, Whitey Bulger died in prison in 2018 while serving a life sentence.
Twitter/Boston InformerJohn Connolly at his murder arraignment hearing in 2005.
Thus, the reign of one of American history’s most unexpected criminal duos — one of the Boston Mob’s leading members and the “dapper” FBI agent who did more to take down the city’s Mafia than few others in the force — came to a close.
In the end, though, Connolly never was the “good cop” he portrayed himself to be. As U.S. Attorney Michael Sullivan once told The New York Times, “John Connolly became a Winter Hill Gang operative masquerading as an FBI agent.”
After reading about disgraced FBI agent John Connolly and his secret partnership with Mob boss Whitey Bulger, learn about Freddy Geas, the inmate who murdered Bulger in prison. Then, go inside the true story of John Douglas, the FBI agent who profiled history’s most notorious serial killers.
