On October 30, 2018, notorious Boston gangster Whitey Bulger was killed at Hazelton Penitentiary in Bruceton Mills, West Virginia—having just transferred from a facility in Oklahoma City one day prior. He was 89 years old, and the FBI has opened an investigation regarding his death.
James “Whitey” Bulger, so nicknamed for his blond hair, spent decades running the streets of Boston as the city’s premier mobster. After committing various felonies in his teens, and a brief stint in the U.S. Air Force, he served nine years in the Atlanta Penitentiary and Alcatraz. Even for a man like Bulger, it was an unsettling experience: He later claimed he'd been an unwilling participant in MK-Ultra experiments.
Following Bulger’s release in 1965, he became embroiled in the mob war between the Kileens and the Mullens—an entanglement that would ultimately set him on top of Boston’s seedy underworld. By 1979, he was the head of the Winter Hill Gang, having usurped the two notorious gangsters who preceded him.
Few of Bulger’s kind enjoy such illustrious careers, but there was a reason he managed to evade prison for over four decades. Secretly, he was protected by a FBI agent named John Connolly.
Whitey’s insider knowledge of the Patriarcas—a crime family of interest at the time—was judged too valuable to keep him locked in a cell. Thus, the FBI recruited him as an informant, turning a blind eye to Bulger’s nefarious dealings. Their partnership ended in the mid-1990s when a joint task force, operating independently of the FBI, launched an official manhunt. Only then was Bulger considered one of America’s most wanted fugitives—though he would not be arrested until 2011.
The FBI’s leniency came at a serious, violent price. During his legendary crime spree, Whitey murdered nineteen people, including 26-year-old Debra Davis. The longtime girlfriend of Bulger’s right hand man, Stephen Flemmi, Debra learned that both men were FBI informants. The discovery came when Flemmi, enraged by Debra’s insistence that he skip a late-night meet-up with Bulger, admitted to his collaboration with John Connolly.
Bulger was infuriated by Flemmi’s confession. If Debra reported them to law enforcement, she would not only jeopardize their precarious relationship with the FBI, but their entire lives. Aware that John Connolly was too great an asset to lose, Flemmi conceded to Bulger’s demands that they eliminate Debra altogether. They hatched a plan: Bulger would take Debra to the mall, then lure her to a designated location, whereupon Bulger would kill her. In about the decision to take Debra shopping prior to her murder, Flemmi simply said, “You’re are so negative about it. Why don’t you hear the positive side of it?” In Flemmi’s mind, it was an act of generosity: He had given Debra one last happy experience.
Unfortunately, the criminals' plan succeeded on a September night in 1981. Just hours after Bulger strangled Debra to death, Flemmi dug her grave along the banks of the Neponsit River. Nineteen years later, her remains were finally found...
Keep reading for an excerpt from Whitey's Payback, and then download the book.
Of all the murders James “Whitey” Bulger is alleged to have committed in his twenty-year run as the Mob boss of Boston, the killing of Debra Davis stands alone. Whitey is alleged to have strangled the woman with his bare hands.
Davis, age twenty-six, was the girlfriend of Bulger’s gangster partner, Steve Flemmi. Bulger and Flemmi were concerned that Davis, a blond-haired beauty, had learned that they were both informants for the FBI. One night in September 1981, Flemmi, forty-six at the time, brought Davis to a house on Third Street in South Boston, or “Southie,” a tight-knit neighborhood that served as the base of Bulger and Flemmi’s criminal operations. Flemmi and Davis had been arguing. After nearly nine years together, Davis wanted out of the relationship. Flemmi wanted her out also, but not in the way Davis planned. Waiting in the house on Third Street was Whitey Bulger, fifty-two years old. Bulger suddenly emerged from the shadows and wrapped his hands around Davis’s throat. She struggled to break free. Squeezing tightly, never letting go of her neck, Bulger dragged Davis down to the basement, where he finished the job. Afterward, using a pair of pliers, Flemmi pulled the teeth from Davis’s head so that the body could not be identified by dental records. They later trussed and wrapped up the body and dumped it in a shallow grave near the Neponset River in Quincy, Massachusetts.
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Steve Davis never got the chance to say good-bye to his sister. She had disappeared seemingly without a trace. Two or three times Flemmi came to Steve’s mother’s house in tears, professing not to know where Debra was or why she had disappeared, but then they didn’t hear from him anymore.
Looking back now, thirty years later, Steve, at age fifty-three, has some regrets. He had his own run-ins with the law, and, from neighborhood scuttlebutt and street knowledge, knew all about Bulger and Flemmi. “I tried to warn her,” he remembers. “I said, ‘Your boyfriend is not a nice guy. He’s dangerous. People fear him.’ She would say, ‘Yeah. But what’s he gonna do to me?’ ”
The Davis family suspected Bulger and Flemmi of having killed Debra, but they didn’t know for sure. Debra’s mother had conversations with FBI agents who claimed they were investigating the disappearance, but they seemed more interested in what she knew about Flemmi than the whereabouts of Debra. Steve wanted to talk to the FBI, to go with his mother, who was meeting with agents at strange locations and odd hours, but she said, “No.” Says Steve, “When an agent told her, ‘You have nine other kids to worry about now,’ she took that as a threat and stopped meeting with them.”
It took nearly twenty years for the Davis family to learn that Debra had been the victim of a homicide, and that Bulger and Flemmi were the culprits. The details of the killing, and Bulger and Flemmi’s role as Top Echelon informants for the FBI, was revealed by Flemmi in the late-1990s, when he was arrested and later found his calling as the biggest snitch in the history of the Boston underworld. In court, Flemmi described the murder, the removal of teeth, and how they wrapped up the body of Debra Davis and buried it near the river. While Flemmi sang his treacherous song from the witness stand, Bulger was on the run, where he remained for sixteen years, living, as we’ve now learned, for most of that time near the beach in Santa Monica, California. When he was spectacularly apprehended last June, Bulger had $822,198 cash hidden in the wall of his condo and an arsenal of thirty guns, including semi-automatics, a machine gun, and a sawed-off shotgun.
Steve Davis remembers the day he received word they had captured Whitey. A cousin called: “They got him!” Davis watched the early reports of Bulger being transferred from Santa Monica, where he had been cohabitating with his female companion, Catherine Greig, while on the lam. He heard of the multitude of charges that Bulger would now be facing. Davis thought then and still thinks: It’s not a done deal. With the power Bulger has had in politics and with the FBI, he could find a way to manipulate the situation to his advantage. Now Davis is less fixated on what will happen to Bulger in court than he is on what he’d do to Bulger if he got his hands on him.
“I’m an eye for eye kind of guy,” says Davis. “I’d do to him what he did to my sister…They talk about closure. Fuck closure. Give me fifteen minutes with Bulger and I’ll give him closure. I’ll shoot him in the fuckin’ head.”
In Boston these days, revenge is a dish best served cold. Since last June, when news of the capture of Bulger and Greig first settled over the city like a bad weather pattern, the city has been stewing in its own juices. Family members of Bulger’s many victims (he is charged with nineteen murders) have been vocal in their demands that the full weight of the criminal justice system be brought to bear on Whitey. Federal prosecutors have begun strategizing: In July, all of the racketeering counts in the indictment against Bulger were dropped, so that the U.S. attorney’s prosecution team can zero in on the multiple murder charges. The thinking is, this way, the road to justice will be accelerated and less encumbered by Bulger’s staggering multitude of criminal acts stretching back to the mid-1960s and across the country with outstanding murder indictments in Florida and Oklahoma.
Justice in court is one thing and outside the courtroom something else entirely. Forty years ago, when Jim Bulger first rose to power in the city’s organized crime structure, he did so as the result of a gangland revenge war that lasted almost a decade. From the mid-1960s to the mid-1970s, mobsters and innocent bystanders were shot, knifed, strangled, and mangled. Sixty-six murders were attributed to this internecine gang war, a tit-for-tat series of killings that were more about underworld retribution than anything else.
When it was all over, in 1975, Bulger emerged as a key powerbroker. It was also around this time that he secretly began to work as an informant for the FBI, under the supervision of Special Agent John Connolly. Bulger fed Connolly information about the local Mafia, with whom Bulger did business. In return, Connolly tipped off Whitey about local law enforcement investigations in which he was a target, which gave Bulger a tremendous edge throughout his long criminal career.
And then there was the brother, State Senator William “Billy” Bulger, who for close to twenty years was the most powerful politician in state government. Billy sometimes ran interference for Whitey by inquiring about law enforcement investigations involving his brother and making implied threats.
Over the decades, untold people, both criminals and average citizens, were drawn into and/or burned by what the Boston Globe christened “the Bulger Mystique.” Many are now looking for justice. But to those who know Whitey best, their concern is how Bulger might try to use his current predicament to exact revenge on his enemies.
“Since at least the early 1990s, he’s had a strategy for when he got pinched,” says Kevin Weeks, who stood alongside Bulger as his right-hand man when the gangster was at the height of his power. “It’s his nature to be manipulative. Machiavellian. He’ll be looking to hurt people who hurt him. To even scores. He will want to rewrite history.”
At one point in his life, Weeks looked up to Bulger as if he were a big brother, or an uncle. At the age of nineteen, he was handpicked by Whitey to serve as his “muscle.” When Bulger wanted someone physically threatened or assaulted, Weeks was his man. Brawny and physically capable, Weeks broke bones, once beating a man who owed Bulger money so brutally that he shattered the bones in his own hand. Weeks was also frequently called upon to help Bulger and Flemmi dispose of the bodies of their many murder victims.
In 1999, after Bulger went on the run and Flemmi began to spill his guts to the Feds, Weeks cut his own deal with the government. He literally told investigators where the bodies were buried, including the body of Debra Davis, who Weeks had helped bury. Weeks testified in court and served five years in prison. He was paroled in 2004 and lives once again in Southie.
Of his time with Bulger, Weeks says, “I ain’t gonna lie to you, I had some exciting times with the guy. We had fun out on the street. But then we all found out he was a rat for the FBI. I felt betrayed. And for a while I was angry. But I’ve had time to think about things. Mostly, I blame myself.”
What Weeks remembers best about Bulger is this: “He was a hard guy, tough as nails. A stone-cold killer. I know he’s eighty-two now, but still, he’s in great shape, mentally strong. I hear they’ve got him in protective custody to protect him from other inmates. But don’t put it past him: He might try to kill somebody himself. Put a shank in his hand, and he’d know what to do with it.”
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Featured photo of Debra Davis courtesy of the FBI