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‘Whitey’ Bulger’s handler, John Connolly, given 2039 parole date in slaying

Ex-FBI agent John Connolly would be 98 in 2039, the year when a Florida panel has said he is eligible for parole.
Ex-FBI agent John Connolly would be 98 in 2039, the year when a Florida panel has said he is eligible for parole.File 2008/Associated Press

Former FBI agent John J. Connolly Jr.’s bid for early release was rejected Monday by a Florida commission that ruled he won’t be eligible for parole until 2039 for his role in a 1982 slaying orchestrated by James “Whitey” Bulger.

Connolly, whose 77th birthday is Tuesday, was not present during the brief hearing in Tallahassee that marked his first bid for parole since he was convicted of second-degree murder in 2008 for the shooting death of Boston businessman John Callahan.


Although Connolly was sentenced to 40 years in prison, he was eligible for early release because the slaying was in 1982, before tougher sentencing laws were adopted in Florida.

The Florida Commission on Offender Review set a presumptive parole release date of June 26, 2039, for Connolly, according to a commission spokeswoman. He would be 98. However, he will have another opportunity to argue for parole in December 2023.

“I’m pleased with the decision,” Callahan’s son, Patrick, 49, of Winchester, said during a telephone interview. “It’s essentially a life sentence.”

However, Callahan added that he has sympathy for Connolly’s three sons because he knows what it’s like not to have your father around.

A number of Connolly’s longtime friends wrote letters and e-mails urging the commission to release him.

“Of course, we believe he was wrongly convicted on the basis of lies of career criminals, mobsters and killers,” wrote William M. Connolly, a retired attorney from Chestnut Hill. “John has been punished far too much!”

The once-decorated FBI agent, who grew up in the same South Boston housing development as Bulger and recruited him as an informant, was not in Florida when Callahan was killed. But a Miami jury found Connolly leaked information to longtime informants Bulger and Stephen Flemmi that prompted the gangsters to order the death of 45-year-old Callahan, an accountant and former gambling company executive with ties to Bulger’s gang.


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

“I can’t stand the fact he is walking around,” Patrick Callahan said of Martorano, adding that the only consolation is that the others involved remain behind bars.

“Everyone else has to stay locked up or there would be no justice.”

Bulger, who was captured in 2011 after more than 16 years on the run, is serving a life sentence for participating in 11 murders. Flemmi is serving a life sentence for 10 murders.

Connolly continues to maintain his innocence. In January, the director of the Miami Law Innocence Clinic filed a motion to overturn Connolly’s conviction.

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