In the early 1970s, Boston FBI agent John Connolly formed an unexpected relationship that would help him capture many high-profile criminals over the next 15 years. By collaborating with Whitey Bulger, the leader of the Winter Hill Gang in the city, he gained inside information about Bulger's rivals in the Mafia.

In return, it was reported that Connolly protected Bulger for nearly two decades; providing him with information about any investigations opened against him. This allowed Bulger to successfully build his crime empire and rise to the top of Boston's Irish Mafia.

Thomas Landers/The Boston Globe via Getty ImagesFBI agent John Connolly, 1987.

This illegal partnership continued until Connolly retired from the FBI in 1990. However, this situation came to light in 1998. Subsequently, Connolly faced federal charges for loan sharking, obstruction of justice, and even a murder related to his role in the death of a Boston businessman.

This is the story of John Connolly, who partnered with one of Boston's most notorious criminals to advance his career.

John Connolly's Relationship with Mafia Boss Whitey Bulger

John Joseph Connolly Jr. was born on August 1, 1940, in Boston. His father worked at Gillette, and his mother was a housewife. The family was poor, and Connolly grew up in the Old Harbor Housing Project. The Bulger family lived just a few doors down.

Facebook/Dirty Old BostonOld Harbor Housing Project in 1940.

According to Boston.com, Connolly was good friends with Billy Bulger, the younger brother of future Mafia boss James “Whitey” Bulger. Connolly and the older Bulger did not often meet due to their age difference (Bulger was 11 years older than Connolly), but they were aware of each other.

The Boston Globe reported that Whitey Bulger once chased eight-year-old Connolly away during a fight over a ball. At that time, 19-year-old Bulger had already gained notoriety for running the Mercer Street Gang.

Connolly's family moved from the housing project when he was 12, and he likely did not see Bulger again until the 1970s. By that time, they were living very different lives.

Wikimedia CommonsOne of the oldest photos of Whitey Bulger from 1947.

Bulger continued to rise in Boston's criminal underworld and soon promoted from the Mercer Street Gang to the much larger — and more deadly — Winter Hill Gang. Meanwhile, Connolly continued at Boston College, took law school classes, and began working as an FBI agent in the Boston field office in 1973. Two years later, he would once again encounter his former neighbor Whitey Bulger.

The Unexpected Partnership Between an FBI Agent and a Crime Boss

In 1975, John Connolly reportedly convinced Whitey Bulger to become an informant. The deal was simple: Bulger would provide Connolly with information about rival gang members, and Connolly would protect Bulger from prosecution for his own illegal activities. For over a decade, the plan worked flawlessly.

Thanks to the tips he received from Bulger, Connolly was able to capture key figures like Gennaro Angiulo, the head of Boston's Italian Mafia, according to Miami New Times.

He also helped bring down the Patriarca crime family. Former FBI agent Joseph D. Pistone wrote in his book The Ceremony: "The reign of the Patriarca Family was almost over. A significant amount of credit for the downfall of that crime family should go to Special Agent John Connolly."

Wikimedia CommonsWhitey Bulger and his partner Stephen Flemmi in the 1980s.

Bulger benefited from the deal as much as Connolly did.

Removing his enemies from the streets meant less competition for things like the trafficking of illegal substances. Bulger and his partner Stephen Flemmi were able to establish a drug empire that made the Winter Hill Gang one of the most powerful factions in Boston's criminal underworld. With Connolly's protection, Bulger literally got away with murder.

In 1990, John Connolly retired after serving 22 years as an FBI agent. Bulger was removed from his role as an informant, and by 1995, the FBI charged him with loan sharking and extortion. The symbiotic relationship between the criminal and law enforcement came to a bitter end — and Bulger was not the only one who ultimately faced justice.

John Connolly's Arrest, Trial, and Prison Sentence

By 1998, details about John Connolly's secret partnership with Whitey Bulger began to emerge. The following year, he was indicted on his first federal charges, and in 2002, he was convicted of loan sharking, obstruction of justice, and lying to an FBI agent.

These charges related to Connolly providing Bulger and Flemmi with information before charges were brought against them in 1995 and warning them to flee. He later lied to an FBI agent about his involvement. In 2002, he was convicted and received a 10-year prison sentence.

Twitter/@picturebostonJohn Connolly leaving a federal courthouse in 2002.

However, Connolly's most serious charges stemmed 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 to the mafia leader killing a man.

The 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 link him to the murder. Connolly was reported to have leaked this tip to Bulger, which led Bulger to issue a murder order to eliminate Callahan.

John Connolly was sentenced to an additional 40 years in prison for this crime. He served until 2021 and received medical parole due to health issues. Meanwhile, Whitey Bulger was killed in prison in 2018 while serving a life sentence.

Twitter/Boston InformerJohn Connolly at a murder trial in 2005.

In conclusion, the reign of one of the most unexpected crime syndicates in American history — the leading members of the Boston Mafia and the "stylish" FBI agent who did more to take down the city's Mafia — came to an end.

Ultimately, although Connolly presented himself as a good cop, he was anything but that. As U.S. Attorney Michael Sullivan once told the New York Times, "John Connolly became a Winter Hill Gang operator disguised as an FBI agent."