Kevin Weeks

Actor Jesse Plemons portrayed Weeks in the 2015 film Black Mass.

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". Weeks stated that he was approached by one of his fellow prisoners, a made man in the New England crime family, who made a surprising suggestion–he should testify against Bulger and Flemmi. As the mafioso put it, "Remember, you can't rat on a rat. Those guys have been giving up everyone for thirty years." He was also unnerved when two lawyers told him that his chances at trial were dismal. Prosecutors were outraged at Winter Hill's crime spree, and were also frustrated when IRA sleeper associate James "Gentleman Jim" Mulvey refused to flip. Weeks recalled that his attorneys told him that prosecutors wanted to take their anger out on Weeks and press for the maximum if he were convicted–which would have all but assured he would die in prison. In addition, Weeks was also deeply impressed by the cooperation of John Martorano, a legendary enforcer for the Winter Hill Gang.

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."

Weeks was released from Federal prison in early 2005. He collaborated with journalist Phyllis Karas (of People magazine). Weeks's account of his life with Bulger and Flemmi was published in March 2006. He was a star witness at Connolly's 2008 trial on state charges of murdering former World Jai Alai president John Callahan, as well as at Bulger's 2013 trial on racketeering charges two years after Bulger was finally captured. At the latter trial, Bulger lost his composure when Weeks called him a rat; the two former compatriots almost came to blows.

On November 17, 1999, Weeks, O'Neil, 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.

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,

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,

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.

On the night of May 11, 1982, Bulger was told the whereabouts of a former associate turned federal informant, Edward 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 "Gentleman Jim" Mulvey, a Winter Hill associate, who was later tried and acquitted. Mulvey remained the prime suspect, even though he had relocated to the Pacific Northwest after an apparent falling out with Bulger after he discovered Bulger was also an FBI informant, until 1999, when Weeks agreed to cooperate with investigators.

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.

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.

In 1975, Weeks became a bouncer at a popular neighborhood bar called Triple O's Lounge, owned by Kevin O'Neil. 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.

Weeks 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 Weeks (born March 21, 1956) is an Irish-American former mobster and longtime friend and mob lieutenant to Whitey Bulger, the infamous boss of the Winter Hill Gang, a crime family based in the Winter Hill neighborhood in Somerville, Massachusetts.

Kevin Weeks was born in South Boston, Massachusetts on March 21, 1956, to a working-class family of 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 (this may be incorrect as no record of him exists in BoxRec). When he was 26, 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.