Kevin Weeks

Kevin Weeks (born March 21, 1956) is a former Irish American mobster and a longtime friend and confidant to James J. Bulger, the infamous boss of the Winter Hill Gang, a crime family based out of the Winter Hill neighborhood in Somerville, Massachusetts.

After his arrest and imprisonment in 1999, he became a cooperating witness. His testimony is viewed as responsible for the convictions of FBI agent John Connolly and mobster Stephen Flemmi. Since his release from prison, he has written the bestselling true crime memoir, Brutal: My Life in Whitey Bulger's Irish Mob and Where's Whitey?, which was also written with Phyllis Karas, a fictional novel using Bulger as a character. Promotion for the book started on the day the FBI stepped up its efforts to catch Bulger with an advertisement; Bulger was caught two days later.


Kevin Weeks was born in South Boston, Massachusetts to a working-class family of mixed Irish and Welsh descent. He was the fifth child in a family of six and grew up in the Old Colony Housing Project at 8 Pilsudski Way, apartment 554.

His father, John Weeks Sr., originally hailed from Brooklyn, New York. He changed tires for a living and later obtained a position with the Boston Housing Authority. John Sr. was a WWII veteran and had served in the infantry; he also had fought as a professional middleweight boxer. When he was twenty-six, he married Margaret, who was from Boston. A full-time homemaker, she suffered from severe arthritis and went about the family's tenement on crutches. Kevin had two brothers, William and John Jr., and three sisters: Maureen, Patricia and Karen. John Sr. trained his sons in boxing and earned extra money by coaching prizefighters. Kevin first started attending school at Michael J. Perkins, but then changed to John Andrew School in Andrew Square for grades 5 and 6; he finally completed elementary school at Patrick F. Gavin School. He graduated from South Boston High in 1974, ending his formal education. His two brothers would later go on to graduate from Harvard University. His brothers sought out a career in politics; John (Jack) Jr. became an advance man for Massachusetts Governor Michael Dukakis, and William became a selectman in Acton, Massachusetts. Kevin Weeks is also related by marriage to former South Boston liquor store owner and alleged extortion victim Stephen (Stippo) R. Rakes and Boston Police Department Detective Edward (Eddie) Walsh.

Kevin's brother, William, has described the atmosphere of their childhood as follows.

"Smart was good, but having the ability to beat someone senseless! Now that was real power. Education was often talked about in the apartment, but always with the implied threat that if your marks weren't acceptable, be ready to give up your soul to God because your ass belonged to our father... [A]nd As weren't acceptable."

Throughout high school, Kevin Weeks was involved in extra-curricular activities. When he wasn't boxing, he was on a team traveling to swim meets all over New England. His memoirs vividly describe how the busing controversy transformed the previously comparatively peaceful South Boston high schools into hot beds of gang warfare.

Criminal career

In 1976, after he gave up on college, Weeks became a bouncer at a popular neighborhood bar, "Triple O's". This was a frequent hangout of the Winter Hill Gang, an Irish-American crime family which was then headed by James J. "Whitey" Bulger. It was here that Weeks first met Bulger, as well as Bulger's Italian-American partner Stephen Flemmi. Beginning in 1978, Weeks began working for Bulger part-time as muscle and a personal driver. Impressed by Weeks' knack for making money and genuinely liking him, Bulger decided to bring him in closer than any other associate. Meanwhile, Weeks turned to running a loansharking business on the side.

In 1982, just four years after beginning to work as part of the Winter Hill Gang, Weeks left his legitimate job and became a full-time mobster in the gang.

The Halloran murder

On the night of May 11, 1982, Bulger was told the whereabouts of a former associate turned Federal informant, Brian Halloran, known on the streets as "Balloonhead". After arriving at the scene, Weeks staked out Anthony's Pier 4 Restaurant, where Halloran and construction worker Michael Donahue were dining together. As Donahue and Halloran drove out of the parking lot Weeks signaled Bulger by stating, "The balloon is in the air", over a hand held radio. Bulger drove up with a masked man armed with a silenced Mac 10; Bulger himself carried a .30 caliber carbine. Bulger and the other shooter opened fire and sprayed Halloran and Donahue's car with bullets. Donahue was shot in the head and killed instantly. Halloran lived long enough to identify his attacker as James Flynn, a Winter Hill associate, who was later tried and acquitted. Flynn remained the prime suspect until 1999, when Weeks agreed to cooperate with investigators. Narcotics

Bulger, Weeks, and Flemmi became heavily involved in narcotics trafficking in the early 1980s. Bulger began to summon drug dealers from in and around Boston to his headquarters. Flanked by Kevin Weeks and Flemmi, he would inform each dealer that he had been offered a substantial sum to assassinate them. He would then demand a large cash payment not to do so.

Eventually, however, the massive profits of drugs proved irresistible. According to Kevin Weeks,

"Jimmy, Stevie and I weren't in the import business and weren't bringing in the marijuana or the cocaine. We were in the shakedown business. We didn't bring drugs in; we took money off the people who did. We never dealt with the street dealers, but rather with a dozen large-scale drug distributors all over the State who were bringing in the coke and marijuana and paying hundreds of thousands to Jimmy. The dealers on the street corner sold eight-balls, ...grams, and half grams to customers for their personal use. They were supplied by the mid level drug dealer who was selling them multiple ounces. In other words, the big importers gave it to the major distributors, who sold it to the middlemen, who then sold it to the street dealers. In order to get to Jimmy, Stevie, and me, someone would have had to go through those four layers of insulation."

In South Boston, most of the neighborhood's drug trade was managed by a handpicked crew of prize fighters led by John "Red" Shea. Edward MacKenzie Jr., a former member of Shea's crew, has stated that this was done because Shea viewed athletes as less likely to abuse the drugs they were selling.

According to Weeks, Bulger enforced strict rules over the dealers who were paying him protection.

"The only people we ever put out of business were heroin dealers. Jimmy didn't allow heroin in South Boston. It was a dirty drug that users stuck in their arms, making problems with needles, and later on, AIDS. While people can do cocaine socially and still function, once they do heroin, they're zombies."

Weeks also insists that Bulger strictly forbade PCP and selling to children and that those dealers who refused to play by his rules were violently driven out of the neighborhood. In 1990, "Red" Shea and his associates were arrested as part of a joint investigation involving the Drug Enforcement Administration (DEA), the Boston Police Department and the Massachusetts State Police. All refused to testify against Bulger, Flemmi, and Weeks. According to Weeks,

"Of course, Jimmy lost money once the drug dealers were removed from the streets in the summer raid, but he always had other business going on. Knowing I had to build something on the side, I had concentrated on my shylocking and gambling businesses. The drug business had been good while it lasted. But our major involvement in it was over."

Mob boss

Weeks also remained in frequent touch with Bulger, with whom he had several clandestine meetings in New York City and Chicago.

In 1997, shortly after the Boston Globe disclosed that Bulger and Flemmi had been informants, Weeks met with retired agent John Connolly (later sentenced to 40 years in prison), who showed him a photocopy of Bulger's FBI informant file. In order to explain Bulger and Flemmi's status as informants, Connolly said, "The Mafia was going against Jimmy and Stevie, so Jimmy and Stevie went against them."

According to Weeks,

"As I read over the files at the Top of the Hub that night, Connolly kept telling me that 90 percent of the information in the files came from Stevie. Certainly Jimmy hadn't been around the Mafia the way Stevie had. But, Connolly told me, he had to put Jimmy's name on the files to keep his file active. As long as Jimmy was an active informant, Connolly said, he could justify meeting with Jimmy and giving him valuable information. Even after he retired, Connolly still had friends in the FBI, and he and Jimmy kept meeting to let each other know what was going on. I listened to all that, but now I understood that even though he was retired, Connolly was still getting information, as well as money, from Jimmy. As I continued to read, I could see that a lot of the reports were not just against the Italians. There were more and more names of Polish and Irish guys, of people we had done business with, of friends of mine. Whenever I came across the name of someone I knew, I would read exactly what it said about that person. I would see, over and over again, that some of these people had been arrested for crimes that were mentioned in these reports. It didn't take long for me to realize that it had been bullshit when Connolly told me that the files hadn't been disseminated, that they had been for his own personal use. He had been an employee of the FBI. He hadn't worked for himself. If there was some investigation going on and his supervisor said, 'Let me take a look at that,' what was Connolly going to do? He had to give it up. And he obviously had. I thought about what Jimmy had always said, 'You can lie to your wife and to your girlfriends, but not to your friends. Not to anyone we're in business with.' Maybe Jimmy and Stevie hadn't lied to me. But they sure hadn't been telling me everything."


On November 17, 1999, Weeks, Kevin O'Neill, and other Winter Hill associates were arrested in South Boston by agents of the Drug Enforcement Administration and the Massachusetts State Police. The next afternoon, he was presented with a 29-count indictment under the Racketeer Influenced and Corrupt Organizations Act (RICO). At first refusing to cooperate, Weeks was transferred to a Federal penitentiary in Rhode Island.

The informant

Imprisoned in Rhode Island, it took about two weeks for Weeks to decide to co-operate with authorities, leading some in South Boston to dub him "Kevin Squeaks" or "Two Weeks". He has stated that he was approached by one of his fellow prisoners, a Made man in the Patriarca crime family, who asked him, "Kid what are you doing? Are you going to take it up the ass for these guys? Remember you can't rat on a rat. Those guys have been giving up everyone for thirty years." In addition, Weeks was also deeply impressed by the cooperation of John Martorano, a legendary enforcer for the Winter Hill Gang.

He led authorities to six different bodies buried by the Winter Hill Gang, including the triple grave of Hussey, McIntyre and Barrett. He implicated Bulger in the murder of Brian Halloran (nicknamed "Balloonhead" by Bulger) as well as agreeing to testify against Stephen Flemmi and Whitey Bulger. Weeks also testified against two of Bulger's friends in law enforcement; Special Agent Connolly and Lieutenant Richard J. Schneiderhan of the Massachusetts State Police. Weeks was then sentenced to five years in federal prison.


Kevin Weeks married his longtime girlfriend, Pamela Cavaleri, on April 26, 1980 at the Gate of Heaven Roman Catholic Church in their native South Boston. They have two sons, Kevin Barry Weeks, to whom Whitey Bulger stood as godfather, and Brian Weeks, to whom Kevin O'Connor, another former enforcer, stood as godfather. The couple later separated.

Current status

Weeks was released from Federal prison in early 2005. After a major bidding war over his memoirs, he chose to collaborate with journalist Phyllis Karas (of People magazine). Weeks' account of his life with Bulger and Flemmi was published in March 2006.

At a book signing in April 2006, Kevin Weeks told the crowd at a Boston Barnes & Noble that he once intended to return to being a gangster once he was released from prison. "Now I can't," he quipped, "Everybody knows my face."

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