Top Lieutenant: Kevin Weeks writes about 25 years with Whitey Bulger

Adam Sennott
Spare Change News

For 25 years, he was James “Whitey” Bulger’s right-hand man and one of his closest friends.
“[He] was a guy that taught me a lot, there was a friendship there. I really believed in him,” said Kevin Weeks, Bulger’s former top lieutenant . “And now I look here and I say, jeez, did I even know him?”

Weeks was one of the few people within James “Whitey” Bulger’s inner circle. As Bulger’s top Lieutenant, Weeks delivered beatings, helped with shakedowns and even assisted in murders. However, in 1997 Weeks learned that Bulger had kept a big secret from him; he had been an informant for the FBI. Bulger’s betrayal would become a motivating factor in Weeks’ decision to cooperate with authorities and plead guilty to being an accessory to five murders. Weeks has since written two books about Bulger, Brutal: The Untold Story of My Life Inside Whitey Bulger’s Irish Mob, of which 50 percent of Weeks’ proceeds went to family members of the five murder victims, and most recently, Where’s Whitey.

“I was very surprised that he got caught, especially that he got caught in the states here,” Weeks said. “I thought he was over in Europe. I pictured him somewhere in the South of France, the Italian Riviera, the French Riviera, somewhere like that where it was nice and warm and by the ocean.”

According to Weeks, Bulger was intelligent and charismatic, but also all business.

“He was an intelligent guy, charismatic, pretty much he was easy going as far as my dealings with him and stuff,” Weeks said. “He was a real likable guy, but he was very serious too, and all business.

“It sounds funny, he had two different sides to him, you know. The one thing you can’t take away is that the man was brilliant. He beat everybody at their own game. Whether you were a criminal or you were law enforcement, he beat them.”

Weeks says he first met Bulger in while he was a bouncer at Triple O’s, a bar in South Boston which Bulger would frequent. According to Weeks, their conversations started off casually and he didn’t imagine he would someday be helping Bulger run a criminal enterprise.

“No, I don’t think anyone thought it was going to get to that point,” Weeks said. “At the time I didn’t think he had any interest in me at all other than to say hi to me because I worked at the bar.”

Weeks added, “If I had known how everything was going to turn out I wouldn’t have gotten involved, period.”

However, Weeks did get involved and slowly became closer and closer to Bulger. Weeks says he started out bookmaking and helping Bulger confront people.

“When I first started out, I started out not working directly with him, I started out bookmaking, and you know, occasionally I would have a fight or something,” Weeks said. “Sometimes he would ask me to take a ride and basically it was to confront somebody; I gave out a few beatings and stuff and little by little I became closer with him.

“It’s like going to school. You start at the first grade and you end up with your doctorate. It’s just little by little by little, you learn more and more and the crimes become more serious.”
Eventually, the crimes became much more serious as Weeks went on to assist in five murders allegedly committed by Bulger. Weeks would later lead investigators to the victims’ bodies and eventually plead guilty to being an accessory in all five murders.

“At the time [Bulger] would say one thing, or why he was looking for a person or what was going on and he gave reasons why we were going to grab this person, why we were going to talk to them or what was going to happen and stuff,” said Weeks. “But it always ended up that we killed a person.”

Of the five murders he was an accessory to, Weeks says the killing of Deborah Hussey was different than the others.
“It was a female, it was a girl. And after I found out the reason why, I blamed Stevie [Flemmi] for it,” Weeks said. “You never involve women in crime, and you never tell them your business or bring your business home with you. From my understanding, the two women that were killed by him were Stevie’s girlfriend and his stepdaughter. Basically, he had involved them in the business whether he told them what was going on or whatever about connections, or whatever. And that’s why they were killed.”

Weeks says that he hasn’t been in contact with the any of the victims’ family members and that he believes it would be hypocritical of him to ask for their forgiveness.

“I don’t think they’d want to hear from me,” said Weeks. “I wouldn’t even apologize to them because the way I look at it is, I could not forgive somebody for doing that to me or a family member of mine, so I wouldn’t ask them for forgiveness. I’d be a hypocrite, and I wouldn’t expect it.”

Weeks pointed out that while Bulger was a violent man, Flemmi was volatile.

“They both had a penchant for violence; the only difference was that [with] Jim Bulger, nothing had to be decided for 24 hours. He would always think things over, whereas Stevie was more volatile,” said Weeks.

According to Weeks, on many occasions Bulger would elect to walk away from potential scores after taking the time to assess the risks and rewards the job could bring.

“There was plenty of scores we walked away from. You know, drug dealers, people we knew had a lot of money, people we could shake down, people that had a lot of cash in their house,” said Weeks. “And then there were some where people came to us and there would be a score where we could make X amount of dollars, and we always had a formula. Okay, X amount of dollars equals X amount of years, is this worth it if we get caught to do ten years? And if the money wasn’t right, we’d pass on it.

“There’s no sense in committing the crime if you can’t spend the money.”

In 1994, things started catching up with Bulger and he went on the run. Weeks says he stayed in contact with Bulger for several years, providing him with false IDs and information about his case.

“I helped him for the first two years, right up until November of ‘96,” said Weeks. “I was in phone contact with him, basically keeping him up to date on the case, what was going on. Several of the key witnesses involved in the case had died; the case was kind of collapsing. You know, I provided, basically I gave him false IDs and stuff like that.”

Weeks would also find out there was something else besides a penchant for violence that Bulger and Flemmi shared, they had both been informants for the FBI.

“I didn’t believe it at first, and then I went up and saw Stevie, I visited Stevie in Plymouth and he told me,” said Weeks. “Then it was, it was a lot of different feelings, which I really don’t want to relive, but it was a shock, it was betrayal, it was just a lot of anger, a lot of thinking, you know, what did I miss? And a lot of people, a lot of people that were around us said the same thing; no one really believed it at first.”

In 1999 Weeks was arrested and faced charges of his own. However, after learning Bulger and Flemmi had been FBI informants, Weeks decided to cooperate with investigators and according to news accounts, went on to lead police to six bodies and later pled guilty to being an accessory to five murders.

Weeks would serve a little more than five years most of which was spent at Allenwood Federal Prison. Although Weeks cooperated with authorities and gave them information on Bulger, he says that it didn’t change his relationship his friends from South Boston.

“My friends when I went away are my friends when I got out,” said Weeks. “You gotta understand when I made my plea deal, the only people that my plea deal was involved with, basically, was Whitey and Stevie and the law enforcement. But basically, I didn’t hurt anyone on the street. So, people that were on the street that were my friends when I went away, when I came home they were all happy to see me.”

Weeks also stated that he still visits South Boston regularly, though he notes that it is not the same “Southie” that he once knew.

“It’s changed a lot,” said Weeks. “It’s integrated now, and a lot of people that grew up [there] that could trace their families back two or three generations [were] basically forced to move out, they can’t live there anymore because the prices have skyrocketed and you have a lot of young professional people that are moving in there, and it’s a clash of culture right now over there.”

With Bulger finally behind bars, Weeks says the only deal he might be there for him is for a life sentence. However, Weeks does hope he tries to help Catherine Greig, Bulger’s longtime girlfriend.

“I think the only deal he could make is for a life sentence, and that would just plead out, really,” said Weeks. “If he could help anyone I would hope he would help Catherine [Greig], you know. But I don’t know what his thought process is right now.

“She’s a good decent person, you know. Anyone that meets Catherine, their life has been enriched, just meeting her; she’s just such a sweet person.”

As for Weeks, he now works in construction. And while he says he has had opportunities to get back into life as a criminal once he was released from prison, he fought the urge and he is better because of it.

“When I first got out I had opportunities. For a long time I couldn’t find a job, and it gets frustrating, and I thought about things I could do, I knew how to do, and stuff. But I fought the urge and I am glad I did. My life is a lot less complicated,” said Weeks. “I have my boys in my life, I have a good woman in my life and I don’t worry about anything anymore.”

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