Whitey Bulger trial: Stephen “The Rifleman” Flemmi apologizes for misspeaking, not for murdering.

Stephen “The Rifleman” Flemmi apologizes for misspeaking, not for murdering.

Mob boss, James J. Bulger (right) and lieutenant Stephen Flemmi (left).
This FBI surveillance photograph of the former Winter Hill Gang hierachy in the 1980s shows mob boss Whitey Bulger (right) and lieutenant Stephen Flemmi (left).

Photo courtesy FBI

In the weeks since I last reported from the Whitey Bulger trial, much has transpired. One witness yelled “Fuck you” across the courtroom at Whitey. (To be fair, Whitey yelled “Fuck you” first.) A second witness called Whitey a “[inaudible] motherfucker.” (Again, it appeared that Whitey initiated the beef.) And far more disturbingly: An alleged Whitey victim—a man who’d hoped to testify during the trial—was found dead by the side of a road under suspicious circumstances.

Stephen Rakes was a Southie guy who owned a liquor store. He owned it, at least, until Whitey allegedly extorted it away from him with threats of violence. I never spoke to Rakes. But I’d see him here at the courthouse, clocking in each morning like it was his job, observing from the victims’ section. On Tuesday of last week, prosecutors told Rakes they wouldn’t be calling him to testify against Whitey—a profound disappointment for a man who’d waited 30 years to tell his tale while staring his nemesis in the eye.

When Rakes was found dead the next day, still wearing the same clothes, and with police reporting “no signs of trauma,” my first thought was that he’d killed himself amid his grief over being denied this long-awaited moment of closure. It was hard to imagine anyone had motive to kill him. 1) He wasn’t going to be a witness, after all. 2) Even if he were, his testimony about a single extortion incident would barely have registered alongside eyewitness accounts of Whitey strangling and machine-gunning other victims. Yet as the investigation continues, and it comes out that Rakes was found without his wallet seven miles away from his abandoned car, I’m forced to wonder whether he ran afoul of one of the many monsters associated with these proceedings.

One of those monsters, Stephen “The Rifleman” Flemmi, remains on the witness stand on Monday. And we begin the morning with another hurtling f-bomb. Flemmi suggests that Steve Davis, the brother of one of Whitey’s murder victims, might have been a drug user back in the day. Davis is in the courtroom, seeking justice for his slain sister Debra. When he hears his name besmirched, Davis leaps to his feet in the observers’ section and yells, “You’re a fucking liar!” as marshals restrain him.

As a result of this outburst, surprisingly, Flemmi admits he’s misspoken—he’d meant to finger a different Davis brother. “I apologize fuh that remahk,” he says to Davis. Very tactful. Though Flemmi seems to be expressing more remorse for verbally insulting Davis than for assisting in the murder of the man’s blood relative.

Wearing a pea-green windbreaker, breathing heavily into the courtroom microphone, Flemmi—in jail for life due to a plea agreement that spared him the death penalty—recounts key moments of greed, idiocy, and brutality stemming from his decades-long partnership with Whitey. It’s the same gory incidents jurors have heard about before, but we’ve now entered a Rashomon phase in which we receive new perspectives on all these grisly tooth extractions, lime-covered corpses, and basement burials.

Flemmi was the dental specialist of Whitey’s gang. Once a victim was dead and stripped naked, Flemmi would pry out teeth so as to leave no identifying characteristics. He took the job seriously: In one instance, he not only yanked a dead woman’s teeth, he stole the records out of her dentist’s office. Which seems redundant. But who am I to question his methods? The day I start uprooting teeth from dead people’s mouths is the day I’ll start giving advice about it.

Stephen Flemmi mugshot
Stephen Flemmi’s mugshot

Photo courtesy FBI

Time and again, Flemmi asserts that everything was Whitey’s idea. It’s always “he did most of the talking” or “he insisted.” When Whitey shot Boston jewel thief Bucky Barrett in the back of the head, Flemmi says, he had no idea it was about to happen. In fact, he was in the line of fire. “The bullet could have gone through him and hit me,” Flemmi whines. He yelled at Whitey over it. But Whitey just responded “with some asinine statement.”

Flemmi echoes a description we’ve heard before: When done killing, Whitey liked to lie down, take a nap, and let other people deal with the disposal. “Maybe he was mentally or physically exhausted,” Flemmi theorizes. “He got a high from it, and then he was exhausted. That’s my interpretation.”

Once, Flemmi claims, Whitey tried to strangle a man with a thick rope. It wasn’t working, so Whitey unwrapped the man’s neck and simply asked him, “You want one in the head?” The man did. Whitey obliged. But Flemmi reached down and “could feel his neck pulses still pulsating.” So Whitey shot again.

This period, in the early ’80s, was perhaps the darkest chapter in the Bulger saga. The murders become more inane, more fruitless. Women are targeted. Whitey does the deeds up close, sometimes with bare hands. Flemmi—no humanitarian, I assure you—sometimes wonders why it has to happen at all. “He was never gonna talk,” Flemmi notes of one man Whitey decided to silence. The subsequent burial, under a house, also befuddled Flemmi. “I thought it wasn’t a good idea at all. You could have driven a car 2 feet from the side door, you could have done it at night, nobody could see. You could have taken the body and buried it anywhere. But Jim Bulger wanted to bury it in the cellar.”

After listening to Flemmi’s calm testimony, and his constant self-exculpation (he speaks as though he possessed zero agency in these gruesome matters), I am eager to watch defense attorney Hank Brennan sink his teeth into a cross examination and gnaw to the bone. Brennan begins by asking Flemmi to describe his role in the life of “little Debbie Hussey,” the daughter of Flemmi’s longtime girlfriend Marion Hussey.

Flemmi was Debbie Hussey’s de facto stepfather. He read her stories as she bounced on his knee. Or at least he’d testified, in a previous trial, that this heartwarming scene occurred. He now seems inclined to walk the description back.

“You never let her sit on your knee and read her stories?” Brennan asks.

“Of course not!” Flemmi insists, indignantly. “I never did that to my own children.”

“Is it hard for you to accept the fact that you strangled somebody who sat on your knee as a little girl?” asks Brennan.

“Mr. Brennan, I didn’t strangle her,” says Flemmi slowly, trying hard to contain himself. He cannot abide this accusation. He merely lured Hussey to her doom and idly watched as Whitey strangled her. (Which didn’t take long. “She was a very fragile woman.”)

Brennan begins to delve further into Flemmi’s relationship with this young woman he’d been a father to since her infancy. He asks if Flemmi sexually abused Hussey. “When you say abusing her sexually would you clarify that?” asks Flemmi. “Intercourse or oral sex?”

Shortly after this charming bit of nuance, Brennan’s line of questioning is interrupted as court ends for the day. We’ll have to resume this Tuesday. It’s a cliffhanger of sorts, but one we already know has a horrific ending. Debbie Hussey was murdered three decades ago, at the age of 26, and entombed in a Southie basement.