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Whitey Bulger’s ex-FBI handler seeks release from Florida prison amid coronavirus fears

Former FBI agent John J. Connolly Jr., who is serving a 40-year prison term for helping James “Whitey” Bulger orchestrate the 1982 slaying of a gambling executive in Florida, is seeking compassionate release “to protect him from contracting the novel coronavirus,” according to a court filing.

Connolly, 79, is at high risk because he suffers from “multiple severe medical conditions,” including diabetes, an umbilical hernia requiring surgery, skin cancer, and osteoarthritis in his left hip, according to a motion his attorneys filed this week urging a Miami-Dade County circuit judge to order his release.

“The tenuousness of Mr. Connolly’s health condition is exacerbated by the elevated risk of dying from coronavirus if kept in close proximity to infected persons in an institutional setting,” the attorneys wrote.


As of Wednesday, one inmate and 18 staff had tested positive for COVID-19 at the South Bay Correctional Facility in South Bay, Fla., where Connolly is an inmate, according to the Florida Department of Corrections. Four inmates in the state prison system have died from the virus, and 136 inmates and 102 staff have tested positive, according to the department’s website.

Connolly is among scores of Florida inmates who have petitioned the courts for release because of the pandemic, according to the Miami Herald, which first reported Connolly’s request.

Miami-Dade State Attorney Katherine Fernandez Rundle said her office has agreed to the release of more than 100 county jail inmates who were serving less than a year for their crimes, but will strongly oppose Connolly’s request.

“He was a corrupt FBI agent that used his badge to divulge information that led to the death” of John Callahan and other potential witnesses, Rundle said. “He’s where he’s supposed to be.”

Callahan’s widow, Mary, questioned whether Connolly was safer in the Florida prison than he would be if he returned home to Massachusetts, which has become a hotspot for coronavirus.


“I don’t think he should get out,” Callahan said.

The once-decorated FBI agent grew up in the same South Boston housing project as Bulger and recruited him as an informant in the 1970s, according to FBI documents and testimony at numerous court proceedings. Bulger and his sidekick and fellow informant, Stephen Flemmi, provided the FBI with information about their rivals in the Mafia while operating with impunity and getting away with murder for decades. Connolly received more than $200,000 in bribes from the gangsters and leaked them information, according to court testimony.

In 2008, a Miami jury convicted Connolly of second-degree murder for the 1982 slaying of Callahan, a Boston accountant and gambling company executive with ties to Bulger’s gang. Although Connolly was not in Florida when Callahan was killed, jurors found that he leaked information to Bulger and Flemmi that prompted the gangsters to order his slaying.

Flemmi testified 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.

A 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 plea deal, Martorano served only 12 years in prison for participating in 20 murders in exchange for his cooperation with the government.


Connolly was sentenced to 40 years in prison for Callahan’s slaying. At the time, he was already serving a 10-year prison term for a 2002 federal racketeering conviction. In that case, a federal jury in Boston found that Connolly helped Bulger evade capture by warning him to flee just before the gangster was indicted in a sweeping federal racketeering case in 1995.

Bulger, who was captured in 2011 after 16 years on the run, was convicted two years later by a federal jury in Boston of killing 11 people in the 1970s and 1980s while running a sprawling criminal enterprise. He was serving a life sentence when he was beaten to death in October 2018 by fellow inmates at the US Penitentiary Hazelton within hours after he was transferred to the West Virginia prison under controversial circumstances. Flemmi is serving a life sentence for 10 murders.

Connolly continues to proclaim his innocence. A Florida appeals court overturned his 2008 murder conviction, but it was later reinstated. He was denied parole three years ago. A hearing was slated for May on his latest bid to get his conviction overturned, but it has been postponed because of the pandemic.

In the defense motion filed this week, Connolly’s attorneys said the government has authorized the compassionate release of federal inmates who are vulnerable or nearing the end of their prison terms. Many state inmates in Florida have also sought their release.

The motion says Connolly’s brother, a retired Drug Enforcement Administration agent, would pick him up at the prison with personal protective equipment, including a face mask and gloves, and bring him to his home in St. Pete Beach, Fla., where he would remain isolated for at least 14 days.


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