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Former FBI agent convicted of helping James ‘Whitey’ Bulger orchestrate 1982 slaying granted medical release

In this Oct. 15, 2008 file photo, former FBI agent John Connolly listened to the testimony during his trial in Miami, Fla. The Florida Commission on Offender Review granted him medical release Wednesday and he will be released from prison after serving nearly 19 years.Alan Diaz/Associated Press

John J. Connolly Jr., a former FBI agent convicted of helping James “Whitey” Bulger orchestrate the 1982 slaying of a gambling executive in Florida, was granted medical release Wednesday and will be released from prison in Florida after serving nearly 19 years.

The Florida Commission on Offender Review voted, 2-1, to release Connolly after doctors said he is terminally ill and is likely to die within a year. Connolly, 80, has cancer and diabetes and has been receiving treatment at a state prison hospital in Lake Butler, Fla.

In 2008, Connolly was convicted of second-degree murder in the 1982 death of Boston businessman John B. Callahan and sentenced to 40 years in prison. At the time, he was already serving a 10-year sentence for a 2002 racketeering conviction.


In a statement read by a victims’ advocate during a telephone hearing Wednesday, Callahan’s son, Patrick, said he did not oppose Connolly’s release because of his prognosis.

“Let his family have this one year with him before he dies,” the statement read. Callahan’s widow, Mary, said in a statement that she did not oppose Connolly’s release as long as he was closely monitored.

Commission chairman Melinda N. Coonrod said Connolly was a law enforcement official convicted of a serious crime. But given his age and medical condition, she said “I do not feel he poses a risk.”

Connolly’s brother, James, a retired Drug Enforcement Administration Agent, said Connolly “has a very strong and stable family situation” in the Boston area if he returns for medical care. He said his brother has undergone several surgeries to remove melanoma, was revived from a diabetic coma, and suffers from a variety of other debilitating ailments.

“He’s 80 years old and no threat to anybody,” he said.

Connolly and Bulger grew up in the same South Boston housing project, and in the 1970s Connolly recruited Bulger as an FBI informant. But the arrangement soured and Connolly, who retired from the FBI in 1990, was ultimately convicted of racketeering and obstruction of justice for tipping off Bulger and his right-hand man, Stephen “The Rifleman” Flemmi, in late 1994 that they were about to be indicted. Bulger fled Boston and became one of America’s Most Wanted fugitives until his capture in 2011.


During Connolly’s 2008 trial, Flemmi, who is serving a life sentence for 10 murders, testified that Connolly was like a member of Bulger’s gang, routinely leaking information to them and pocketing $235,000 in payoffs from them between 1981 and 1990. In return, he said, they fed him information about the FBI’s top priority at the time, the Mafia.

Flemmi said Connolly had warned him and Bulger that the FBI was looking to question Callahan about a 1981 murder in Oklahoma and two other killings in Boston.

That tip led Bulger and Flemmi to plan Callahan’s murder, prosecutors said. An associate, John Martorano, testified that he lured Callahan to Florida, shot him, and left his body in a car at Miami International Airport. Though Connolly was far from the murder scene — he was on Cape Cod — an appeals court ruled in 2015 that his murder conviction was proper because he was a “principal in the first degree.”

Under a controversial deal, Martorano served only 12 years for killing 20 people in exchange for his cooperation with prosecutors. On Wednesday, Connolly’s attorney, James E. McDonald, told the commission it was important to consider that his client “was nowhere near the scene of the crime” and that the man who killed Callahan was free.


“I think the time has come to show some compassion and do the right thing and let John finish out his life out in the sunshine,” Gerald Franciosa, a retired supervisory Drug Enforcement Administration agent who worked with Connolly on organized crime cases, told the commission. “The killer is actually walking around in Hollywood, Fla. Let John go home and finish out his life.”

Bulger was caught in California after 16 years on the run and later sentenced to life for killing 11 people during the 1970s and ’80s. He was beaten to death in a federal prison in West Virginia in 2018, just hours after he was transferred there. Flemmi remains in federal prison.

Last April, Connolly’s lawyers argued that his medical conditions — among them diabetes, an umbilical hernia requiring surgery, skin cancer, and osteoarthritis in his left hip — put him at great risk for the coronavirus and sought his release. A judge denied the request.

Prosecutors had opposed Connolly’s release. But on Wednesday, Michael Von Zamft, senior trial counsel at the Miami-Dade state attorney’s office, said the office would not oppose his release if the commission confirmed that prison medical staff had determined he was terminally ill.

Commissioner Richard D. Davison voted against Connolly’s release, saying “it is my belief that Mr. Connolly still poses a risk to society, despite his current medical prognosis,” he said.


Connolly must remain at a residence or hospice approved by prison authorities and may only leave for medical care.

On Wednesday, Connolly’s longtime friend, Francis Joyce, the former executive director of the Massachusetts Convention Center, told the commissioners he would pick Connolly up from prison and let him stay at his condo in South Florida. He said he would take him to treatment and pay for his medical care while he’s in Florida.

Massachusetts US Attorney Andrew Lelling said it wasn’t unusual for a terminally ill inmate who was no longer considered 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,” he said.

Shelley Murphy can be reached at shelley.murphy@globe.com. Follow her on Twitter @shelleymurph.