A Key Figure in the ‘Whitey’ Bulger Case Has Been Released from Prison

The notorious mobster’s FBI handler, who’s suffering from cancer, was let out on a conditional medical release

John Connolly, the FBI agent and convicted murderer who tipped notorious Boston mobster James “Whitey” Bulger to a pending federal indictment, has been released from Florida prison on a conditional medical release. Connolly’s tip helped facilitate the 16 years bulger spent on the lam, until he was tracked to an apartment in Santa Monica and arrested in 2011.

Connolly was serving a 40-year sentence for second-degree murder in connection with his relationship to the former Boston mob boss and FBI informant. The duo was part of a murderous reign of terror that inspired two Hollywood movies, Martin Scorsese’s The Departed and Black Mass starring Johnny Depp.

The South Boston native, who grew up in the same public housing development as Bulger and his brother, former Massachusetts Senate President William Bulger, was convicted in 2008 in connection with the killing of gambling executive John Callahan in Fort Lauderdale. Connolly tipped Bulger and another gangster on the FBI payroll, Stephen “the Rifleman” Flemmi, that Callahan was about to implicate the gang in another killing. Days later, Callahan was shot dead by a Bulger hitman.

Bulger went on the lam in 1994 and for 16 years was behind only Osama Bin Laden on the FBI’s Ten Most Wanted Fugitives list. He was finally captured on June 22, 2011 in Santa Monica, where he was hiding in plain sight in a rent-stabilized apartment at 1012 3rd Street with his longtime lover, Catherine Greig.

Over the years “Charlie and Carol Gasko,” the aliases the couple developed after coercing a homeless man at Palisades Park to hand over his social security number, lived the Westside life, strolling the Third Street Promenade, dining at Michael’s near their $837 a month apartment, and taking in a Red Sox or Celtics game at Sonny MacLean’s, the Santa Monica Irish pub.

Bulger is not the only one from that dark period of Boston history to end up in L.A. Right around the time of Bulger’s flight, Connolly’s boss, FBI supervisor John Morris—nicknamed “Vino” because Bulger and Flemmi loved to gift him expensive cases of wine—was promoted and sent to the FBI field office where, astonishingly, he took over a public corruption and government fraud unit. Morris said he worked in L.A. from 1994 until 1995 and retired after he got a call from a “Mr. White” with a warning after the Boston Globe revealed the FBI’s relationship with the fugitive mob boss.

The voice on the other end of the line was Bulger’s, and he knew it well. Bulger had dined at his home several times, along with Flemmi, and he knew Bulger meant business, which led him to have a career-ending heart attack.

Morris testified at the ganger’s 2013 trial. “He wanted me to use my Machiavellian mind to contact my sources at the Globe to get them to retract the story about him being an informant, and that if I didn’t, I had taken money from him, and if he went to jail, I was, ‘coming with him,’” Morris testified. The stress of the call, he testified, and the guilt that came with climbing into bed with men like Bulger and Flemmi, forced him to quit.

“I could remember the director coming in and giving speeches on integrity, and I just—I couldn’t take it anymore. I had to get out,” Morris told the court.

In 2013, Bulger, who insisted at his trial that he never worked for the FBI, was convicted of 31 counts including racketeering, money laundering, and weapons charges, and was found by the jury to have been involved in 11 murders. He was sentenced to two life sentences plus five years.

In October 2018, Bulger was five years into that sentence when, within hours of an inexplicable transfer to a West Virginia federal penitentiary, his wheelchair was wheeled into a general population area and he was brutally beaten to death and mutilated. No one has been charged with his killing.

On Wednesday, the Florida Commission on Offender Review voted 2-1 to approve Connolly’s medical release following a short hearing where the disgraced FBI agent’s lawyers argued the 80-year-old has cancer and should be allowed to die at home. Connolly’s friend, a former Massachusetts state official, told the board he would drive Connolly from the Florida prison to his Boston home and assume all his medical costs.

It is unclear if Connolly will be living anywhere near Whitey’s paramour, Catherine Greig, who was released from prison last January and is back in South Boston. She has never talked about the $800,000 in cash or the 30 weapons that were found secreted in the walls of the Gasko apartment in Santa Monica.

That hideout has since been torn down and replaced with new condos.

RELATED: Hiding in Plain Sight: Whitey Bulger’s Secret SoCal Hangouts

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