Imprisoned ex-FBI agent who worked with Whitey Bulger seeks release

BOSTON — The former FBI agent serving a 40-year prison sentence for alerting Boston mobster Whitey Bulger that he could be implicated in a murder is seeking to be released from prison on medical grounds.

The Florida Commission on Offender Review will hear the request Wednesday from John “Zip” Connolly, who is being held at the Reception and Medical Center in Lake Butler, Florida.

“It’s on the docket for the 17th and he’s seeking a conditional medical release,” said commission spokesperson Angela Meredith. A majority vote would lead to Connolly’s release, she said.

Connolly’s Cambridge lawyer, Peter Mullane, confirmed to the Boston Herald Friday that Connolly, who is 80, is seeking to be released.

“He has multiple melanomas and pretty bad diabetes. Two serious illnesses,” Mullane said.

Connolly, who was James “Whitey” Bulger’s FBI handler, was convicted in 2008 of second-degree murder after a mob hitman killed World Jai Alai President John Callahan in Fort Lauderdale in 1982. Trial evidence showed Connolly tipped Bulger that Callahan was about to implicate the gang in another killing.

Separately, Connolly 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.

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.

Connolly’s wife and three grown children are still living in the Boston area, Mullane said, and they hope he will be allowed to return to Massachusetts.

“This has been a punishment for the whole family, and they have suffered,” Mullane said.

Callahan’s wife, Mary, also 80, said she just celebrated what would have been her 61st wedding anniversary.

“For me, this is never over. My daughter said that to me recently,” Mary Callahan said Friday. “I remember the last time we celebrated my anniversary, John told me you get me ‘for another year.’ That’s an Irish joke. He actually gave me a string of pearls.”