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Mob Boss Whitey Bulger's FBI Agent, John Connolly, Is Being Released Early From Prison

A former FBI agent, who was found guilty of leaking information to notorious Boston gangster James "Whitey" Bulger that led to the killing of a major sports figure, is being released from prison early on medical grounds.

James "Whitey" Bulger

James "Whitey" Bulger

Photo Credit: US Marshals Services

On Wednesday, Feb. 17, the Florida Commission on Offender Review voted to release John Connolly, who has cancer, so that he may die at home.

Massachusetts U.S. Attorney Andrew E. Lelling said that while Connolly is being shown compassion that was not afforded to his victims, he agrees with the decision to release Connolly.

“It is not unusual for an inmate who is terminally ill and deemed no longer a threat to society to be released to home confinement,” Lelling said in a statement. “While the damage caused by John Connolly’s corrupt relationship with James Bulger and others can never be forgiven, and Connolly has been shown compassion and consideration that his victims were not, we agree … [that] Connolly should be permitted to die at home with his friends and family.”

Connolly was Bulger’s FBI handler while Bulger, a major Boston mob boss in the Winter Hill Gang,  was working as a federal informant. As a result of this information, Connolly was convicted in 2008 in connection to the killing of Wolrd Jai Alai President John Callahan in 1982.

Connolly had tipped Bulger off that Callahan was about to implicate him and his gang in another killing, according to Boston 25 News. In 2002, Connolly was also convicted of racketeering and obstruction of justice in connection with his work with Bulger.

If this all sounds a bit familiar, that's because it was Connolly and Bulger’s relationship that inspired the 2006 film, “The Departed.”

After hiding out for many years, Bulger was arrested, along with his girlfriend, in California in 2011. Bulger died in 2018 when he was killed in a federal West Virginian prison.

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