Why you should care

Because the ways in which crime pays — or doesn’t — are many, varied and unexpected.

Kevin Weeks? Boston Irish Mafia Kevin Weeks? The last time we heard or thought about him, he was muscling his way onto the witness stand to testify against his former boss, Jimmy “Whitey” Bulger. For damn near 16 years, Bulger had the world aswirl over sightings and near sightings as he fled roughly 19 murder charges. But finally, in 2013, he was a defendant in a Boston courtroom, and Weeks was testifying against him. Rendering unto Caesar what belonged to Caesar. It wasn’t pretty.

The underworld has an infamous aversion to snitches. But as far as Weeks was concerned, you can’t rat on a rat. In the courtroom, in an exchange that made headlines, Bulger let Weeks know how he felt. Given his earlier life penchant for shooting and strangling his problems, the now-85-year-old Bulger’s reaction was fairly mild: “You suck.”

A quick and icy response from Weeks: “Fuck you, OK?”

For those who don’t know, Kevin Weeks is an infamous figure in the Boston Irish mafia, a right hand to Whitey Bulger — the subject of an upcoming movie, Black Mass, starring Johnny Depp as Bulger and Breaking Bad’s Jesse Plemons as Weeks — who did a great deal of dirty work. “I regret some things. It’s human,” said former boxer and lifelong martial artist Weeks as we sat in his car curbside in Jamaica Plain, far from the Southie neighborhood that he had called home and where we had started our day. He was a late-in-the-game addition to a book I wrote on interpersonal conflict called Fight: Or, Everything You Ever Wanted to Know About Ass-Kicking but Were Afraid You’d Get Your Ass Kicked for Asking. Weeks and I spent the better part of that day hitting his Boston haunts and for a better part of that day, the leitmotif that returns again and again in his conversation, and possibly his thoughts: how he zigged into the shit and not out of it.

The shit in this instance: the five years he did in prison after having pleaded out to lesser charges and cooperated with authorities in bringing indictments against the then-absent Bulger. “I regret I didn’t spend more time with my kids. And my ex-wife,” Weeks said. And then this, just in case we were waiting for a tabloid TV moment of tears: “You’ll never see me crying on TV for nothing else I did. Fuck that. I can’t change history.” (He declined a more recent request for another interview.)

This history, with body after body and bullet after bullet, proved to be too much of a draw for Hollywood hit-makers, resulting first in Scorsese’s The Departed, a thinly veiled take on Bulger’s reign, with Ray Winstone playing a suspiciously Weeks-esque sidekick to Jack Nicholson, and now again in Black Mass. And with two books to his co-written credit, the 2006 tome Brutal: The Untold Story of My Life in Whitey Bulger’s Irish Mob and 2011’s Where’s Whitey?, Weeks’ big breaks — a certain percentage of the proceeds from book sales goes to the victims’ families — are not so much financial as they are the kind of warming you get from a constant and continual media focus: TV shows, book signings and a certain celebrity that comes from not only being a bad man well-met, but also from the sheer weight of celebrities wanting to hang with him instead of the other way around.

During filming of The Departed, when Weeks wasn’t technically advising Leonardo DiCaprio on how to pistol-whip someone, he was to his character born, being pulled off of DiCaprio. “He started getting into character,” the about 5-foot-10-inch Weeks muttered. (Years of being tailed by the feds have led to his peculiar way of talking: into his chest. Lip readers, directional mics, eavesdroppers be damned.) “And he says some shit like ‘When you were an informant …’ and I lost it. I mean, the regular person, well, it takes them some time to get from zero to 60. It usually took less than that time for Jimmy [Whitey] to get to 600. But I wasn’t as bad as all that, but I was hot. Because I never was an informant. What I told never hurt nobody but me. But the agents who were there were trying to calm me down.” He chuckled. DiCaprio “apologized and said, ‘I’ll never make that mistake again, sir.’”

And as amusing as it is to imagine a chastened Arnie Grape, Weeks, it should be remembered, is a 59-year-old man. A twice-married, once-divorced ex-con. An ex-con who, despite his no-regrets clause, has given up a lot and emerged with not so much, outside of memories not to be wished on many or on anyone who is trying to live a normal life.

“I remember once pulling the pickax up out of this guy’s sternum and his whole abdominal cavity came with it,” said Weeks. Part of the deal when he pleaded out was showing where the bodies were actually buried. Or rather reburied. He and Bulger had been stowing them in the basement of a house that they sold, and therefore they had to move them. Body after body, dug up. “Now that was disgusting.” He pointed two of his thickly muscled fingers toward his nose. “Took three days to get the smell out of my nose after that.” Then quiet. (Bulger, who was convicted of racketeering and murder charges and is currently serving two life sentences plus five years, has appealed his conviction.)

A storm has already greeted Johnny Depp’s take on Bulger, a note-by-note piece of perfection for those who actually knew Bulger. A recently released trailer shows Depp as a man whose relationship with his murders had Weeks saying, “They seemed to relax him,” a portrayal that has enraged surviving members of the victims’ families. Steven Davis, whose sister Debra was strangled to death by Bulger back in 1981 after he figured she knew too much, said to The Boston Globe, “A lot of the families are very, very upset about this. It’s too much hurt still going on.”

“Unlike Bulger … Kevin has a conscience,” the Globe’s top crime columnist Kevin Cullen told me. “But in the end, he was a criminal. He just wasn’t a sociopath like Bulger.” Even more significantly, Weeks, atypically, seemed totally fine with going back to real work, even as a laborer — noteworthy when it’s remembered that he is probably just as intelligent as his two older brothers, both of whom went to Harvard.

All of which was not so lost on Weeks, who is now remarried and still living in Boston. Nursing a complicated connection to contrition, Weeks wound up the conversation as we sat amid the sweep of later afternoon Boston traffic: “That’s why you never hear me making a big deal out of only aiding and abetting those murders. If Jimmy had asked me to, I’d have done it. Now it’s not like I didn’t learn anything — I did. But I also know that regret doesn’t do any good.”

An earlier verision of this story incorrectly identified Weeks as Bulger in one reference.

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