James ‘Whitey’ Bulger’s former FBI handler is healthier two years after compassionate release from prison

Florida commission won’t send John Connolly back to prison

John J. Connolly Jr. entered US federal court in Boston for his trial in May 2002.OLIVIA GATTI/Associated Press

John J. Connolly Jr., the former FBI agent convicted of helping James “Whitey” Bulger orchestrate the 1982 slaying of a Boston businessman in Florida, may remain free on compassionate medical release although his health has improved since doctors said he was terminally ill more than two years ago.

The Florida Commission on Offender Review voted 2-1 Tuesday to reject a request by one of the commissioners for a hearing on whether Connolly, 83, should be sent back to prison to complete his 40-year sentence for second-degree murder.

In February 2021, the commission released Connolly after doctors said he was undergoing treatment for cancer and diabetes and was likely to die within a year. Connolly had spent 19 years in prison on federal and state charges.

He was ordered to remain at a residence or hospice approved by prison authorities and told he could only leave for medical care.

“The good news for Mr. Connolly is that he’s getting better,” Commissioner Richard D. Davison said during the brief hearing Tuesday, noting that Connolly’s doctor recently reported that he was well enough to take walks outside his house and around his neighborhood.

But Davison urged the commission to rescind Connolly’s parole, saying his conditional medical release was “not a get out of jail free” policy.

Michael Von Zamft, senior trial counsel at the Miami-Dade state attorney’s office, told the commission that prosecutors had only agreed to Connolly’s release because they were led to believe he was terminally ill and it should now be rescinded because “certainly he is not terminal.”

Commissioner Melinda Coonrod, the body’s chair, said Connolly’s lawyer had asked for the hearing to be postponed until November to give him time to prepare a defense.

But Coonrod and another member said there was no need to hold a hearing. Instead, the commission will monitor Connolly’s health through updates provided by his doctor every 90 days.

“I don’t think his medical condition has changed,” Coonrod said.

In a brief telephone interview after the hearing, Cambridge attorney Peter Mullane, Connolly’s longtime friend and supporter, said Connolly is “unquestionably in poor health at best and requires fairly intensive ongoing medical attention.”

He said Connolly, who is back at his home in Lynnfield, is in remission from cancer and recently underwent a 10-hour surgery that resulted in the removal of his ear. He said doctors have recommended that Connolly take walks for his health.

“He’s certainly not out jogging,” he said. “He’s not a candidate for ‘Dancing With The Stars.’”

Connolly was convicted in 2008 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 by a federal jury in Boston.

Connolly and Bulger grew up in the same South Boston housing development, and in the 1970s Connolly recruited Bulger as an FBI informant. Connolly retired from the FBI in 1990, then was convicted of racketeering and obstruction of justice charges more than a decade later 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 in Miami, Flemmi testified that Connolly warned him and Bulger that the FBI wanted to question Callahan and that the businessman would probably implicate them in the 1981 slaying of World Jai Alai owner Roger Wheeler in Oklahoma, as well as two other slayings in Boston.

Bulger associate John Martorano testified that at the urging of Bulger and Flemmi, he lured Callahan to Florida and shot him to death. In a controversial deal, Martorano served only 12 years in prison for participating in 20 murders in exchange for his cooperation with the government.

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.

During a brief interview Tuesday, Callahan’s widow, Mary, noted that she and her children did not oppose Connolly’s release two years ago.

“He was supposed to die but he’s still alive,” she said. “The way he’s living right now, it doesn’t matter if he’s in prison or not — he’s really in prison with his health.”

After the hearing, Von Zamft, who prosecuted Connolly in 2008, said prosecutors relied on doctors’ claims that Connolly was dying when he was set free and have never been provided any of his medical records.

“Apparently he has had a miraculous recovery to the point they want to let him walk around,” Von Zamft said. “If he’s well enough to be walking around then he should be back in prison.”