Inside Whitey Bulger’s Law Enforcement Connections

From the 1970s to the 1980s, James “Whitey” Bulger ran his criminal empire with federal protection baked into his illegal rackets. Drug trafficking, extortion, murder—it all flourished as the Boston office of the nation’s top federal law enforcement agency turned a blind eye.

Bulger, head of the Winter Hill Gang, leveraged his childhood friendship with then-FBI agent John Connolly, a fellow South Boston native who rose through the ranks selling the myth of top-tier informants as trophies, to evade legal trouble for decades. The relationship between the mobster and the federal agent not only exposed the complicity of one rogue agent, but an institutional culture that coddled corruption, according to former law enforcement officials and journalists who investigated Bulger and Connolly.

Tom Foley, the retired Massachusetts state police commander who spent decades chasing Bulger, recalls to A&E Crime + Investigation how FBI culture incentivized relationships like Connolly’s with Boston’s most feared gangster. In addition to Connolly, Bulger also compromised FBI supervisory agent John Morris, who covered for his fellow G-man. Connolly and Morris also accepted bribes from Bulger.

“The mentality at the time of the FBI on how you moved up the ranks depended on how many top-echelon informants you had,” Foley says. “Over the years, they used to get bonuses if you developed these top-echelon informants.”

A spokesman for the FBI declined to comment to A&E Crime + Investigation about the scandal that rocked the agency’s Boston field office decades ago.

Bulger represented a prime opportunity for Connolly to climb the FBI ladder, Foley says. “It was a feather in Connolly’s cap, and the bureau believed it would benefit them overall,” he explains. “It made [Connolly] look good to the agency.”

Bulger and Connolly knew each other personally. The duo grew up in the same South Boston neighborhood, and Connolly maintained a tight bond with the Bulger family well into adulthood. That familiarity gave Connolly cover to elevate Bulger as one of the bureau’s prized contacts. Connected to Bulger, Connolly was flush with what looked like key intelligence for the FBI. In reality, the deal worked almost entirely in Bulger’s favor, Foley says.

“He was giving them info when he wanted to take out the competition,” Foley continues of Bulger. “We couldn’t get the FBI to see that. By having a top-echelon informant where you can go no higher, it does nothing to achieve your goals.”

While Bulger played informant, he expanded his reach in Boston and beyond, untouchable as investigators like Foley repeatedly watched their work compromised by Connolly leaking information to Bulger. The leaks included the FBI agent tipping off Bulger about the agency's investigation into the death of Roger Wheeler, who was murdered by the Winter Hill Gang in 1981.

Foley recalls the frustration of being forced to fight against both organized crime and the bureau’s stubborn loyalty to its prized source. “From our perspective, Bulger was a target,” Foley says. “But the FBI was in denial.”

For Foley and his team, the fight became a battle not just against Bulger’s intimidation and violence, but against sabotage within the justice system. “The big job for us was to circumvent the FBI and go after Bulger,” Foley says. “Every time we shared info, we got compromised.”

In the late 1990s, after the scandal finally broke into the open, Connolly became the public face of the Boston FBI’s corruption. In 2002, Connolly was convicted for federal racketeering and sentenced to 10 years in prison. Six years later, a Miami jury convicted Connolly for second-degree murder for his role in the Winter Hill Gang slaying of John Callahan, whose body was found in the trunk of Callahan’s Cadillac at Miami International Airport in 1982.

Connolly’s 40-year prison sentence was nullified when a Floria appeals court overturned his murder conviction in 2014. His supervisor, Morris, received immunity for testifying against Connolly. Morris also testified for the prosecution in Bulger’s 2013 trial on federal racketeering and money laundering charges.

Other FBI supervisors in Boston and Washington, D.C., were also aware that Bulger was being protected by Connolly and Morris, Foley says: “Connolly took the hit. He deserved it, but he wasn’t the only one.”

The scandal proved a bitter lesson about the selective application of justice. “You lose faith in the system when you see the FBI not being held accountable like everyone else,” Foley says. “How can you keep Bulger as a top-echelon informant when he is killing people? If it was one of us, we would get indicted.”

Richard Lehr, a former Boston Globe reporter who co-authored Black Mass: Whitey Bulger, the FBI, and a Devil's Deal, agrees that Connolly’s corruption fit neatly into an FBI culture with little incentive for reform.

“At that moment in the ‘70s, I don’t think Connolly necessarily saw it as a huge risk,” Lehr tells A&E Crime + Investigation. “There was already a culture of corruption in the Boston FBI. They had corrupt ties to informants and were breaking laws on how they protected their informants.”

Lehr says the “personal history” between Connolly and Bulger “minimized the risk” to their arrangement. “There was a huge amount of trust that their deal would benefit both of them in a big way.”

Even after the Boston Globe broke stories of Bulger’s FBI protection, real accountability lagged. “After the initial spotlight team coverage that revealed this relationship, not a lot happened for years,” Lehr recalls. “It took a new generation of prosecutors who were not part of that culture to really blow open the scope and the durability of this culture of corruption.”