Ex-FBI agent linked to Whitey Bulger to be freed from prison

A former FBI agent convicted of second-degree murder for leaking information to Boston gangster James “Whitey" Bulger that led to the shooting death of a gambling executive will be released from prison on medical grounds, officials ruled Wednesday.

The Florida Commission on Offender Review voted 2-1 in favor of releasing 80-year-old John Connolly, who has cancer and is believed to have less than a year to live.

Connolly, who was Bulger’s FBI handler, was sentenced to 40 years behind bars after being convicted in 2008 in the killing of World Jai Alai President John Callahan in Fort Lauderdale, Florida, in 1982. Connolly tipped off Bulger and another gangster, Stephen “The Rifleman” Flemmi, that Callahan was about to implicate the gang in a killing, authorities said.

In a statement read to the commission, Callahan’s son said he is not opposed to Connolly’s release, given his prognosis. Callahan’s wife, Mary, also did not object.

“Let his family have this year with him before he dies," Patrick Callahan said.

The state attorney’s office also did not oppose his release.

U.S. Attorney Andrew Lelling, Massachusetts’ top federal prosecutor, said that "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," his office agrees that Connolly “should be permitted to die at home with his friends and family.”

Connolly was also found guilty in 2002 of tipping off Bulger, Flemmi and former New England mob boss Francis “Cadillac Fran” Salemme in late 1994 that they were about to be indicted. Connolly’s tip allowed Bulger to flee and spend the next 16 years on the lam. Connolly served 10 years in prison in that case.

Connolly’s case damaged the FBI’s reputation and prompted reforms, like stricter guidelines for handling criminal informants. Connolly and Bulger’s relationship helped inspire the 2006 Martin Scorsese film, “The Departed.”

Bulger, who was one of America’s most wanted men before being arrested in California in 2011, was killed in federal prison in West Virginia in 2018. Authorities have not charged anyone with his killing, but law enforcement officials said at the time that two Massachusetts mobsters were suspects.

James McDonald, an attorney for Connolly, and Connolly’s brother were among those who spoke in favor of his release. McDonald noted that Connolly was more than 1,000 miles away in Massachusetts when Callahan was killed and that the hitman who pulled the trigger is now a free man.

James Connolly said his brother has has lots of family and friends who can support him in the Boston area.

“He’s no threat to anybody,” he said.