John Connolly, former Boston FBI agent, to be released from a Florida prison

BOSTON — A former FBI agent convicted of second-degree murder for leaking information to Boston gangster James Whitey Bulger that led to the 1982 shooting death of a gambling executive can be released from prison on medical grounds, officials ruled Wednesday.

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

Connolly, who was Bulger’s FBI handler, was convicted in 2008 over the killing of World Jai Alai President John Callahan in Fort Lauderdale in 1982. Connolly tipped Bulger and another gangster, Stephen ‘The Rifleman’ Flemmi, that Callahan was about to implicate the gang in another killing, authorities said.

Connolly is currently being held at the Reception and Medical Center in Lake Butler, Fla.

Boston attorney Peter Mullane, one of Connolly’s lawyers, told Boston 25 News that Connolly’s medical situation is dire.

“He’s seriously ill and has definitely limited mobility,” Mullane said. “And the strength that he has, hopefully, dictates to the doctor and gets the proper medical treatment to stay alive as long as he can.”

Connolly also served nearly 10 years in prison after being convicted in 2002 of racketeering and obstruction of justice for protecting members of Bulger’s Winter Hill Gang from prosecution and tipping them about informants in their ranks. Connolly and Bulger’s relationship helped inspire the 2006 Martin Scorsese film, “The Departed.”

Bulger, who spent 16 years as one of America’s most wanted men before being arrested in California in 2011, was killed in federal prison in West Virginia in 2018.

John Callahan’s widow, Mary Callahan, told Boston 25 News that she agrees with Connolly’s compassionate release, as long as he is supervised.

“He’s not free. He’s never going to be free,” Callahan said. “He’s not free of his health, he’s not free of his reputation. He’s not free.”

Andrew Lelling, the U.S. Attorney for Massachusetts, echoed that sentiment.

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. 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 with the sentiments of Mary and Patrick Callahan that Connolly should be permitted to die at home with his friends and family.

—  Andrew E. Lelling, U.S. Attorney

John Connolly’s relationship with Bulger and Flemmi embarrassed the FBI and fractured relationships between federal and state agencies investigating them.

Retired Mass State Police Detective Lt. Bob Long’s surveillance of Bulger and Flemmi was compromised by that relationship. As Connolly is released, Long is thinking of the victims.

“He turned out to be a gangster with a badge, destroying families and losing their loved ones. They’re not coming home to their families today,” Long said.

John Connolly is being released on conditions. Among them, he must remain confined to wherever he is living and is only allowed to leave to visit a doctor or to attend a religious service.

For now, it’s expected Connolly will stay in Florida, but there’s no restriction against him returning to Boston.

The Associated Press contributed to this report.