About Kevin Weeks
Born 1956. Kevin Weeks is an American autobiographer.
Kevin Weeks (born March 21, 1956) is an American former mobster and longtime friend and mob lieutenant to Whitey Bulger, the infamous boss of the Winter Hill Gang in South Boston, a crime family formerly based in the Winter Hill neighborhood of 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, as well as forcing Bulger's right-hand man, Stephen Flemmi, to plead guilty as well. Since his release from prison, he has written the true-crime memoir, Brutal: My Life in Whitey Bulger's Irish Mob. This was followed by Where's Whitey?, a novel using Bulger as a character, co-written with Phyllis Karas. 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.
Early life 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.
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 graduated from Harvard University and would seek out careers in politics: John Jr. became an advance man for Massachusetts Governor Michael Dukakis, and William became a selectman in Acton, Massachusetts.
Kevin's brother, William, has described their childhood: "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 ... and As weren't acceptable."
Criminal career 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 "The Rifleman" 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. 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 in a blue Datsun, Weeks signaled Bulger by stating, "The balloon is in the air", over a handheld radio. Bulger drove up in a souped-up 1975 Chevrolet Malibu with a masked man armed with a silenced Mac 10 submachine gun; Bulger himself carried a .30 caliber carbine rifle. Bulger and the other shooter, allegedly Pat Nee, opened fire and sprayed Halloran and Donahue's car with bullets. Donahue was shot in the head and killed instantly. After Halloran stumbled out of the car, Bulger continued to shoot him as his writhing body was "bouncing off the ground", according to Weeks. Weeks said: "Everything I did, every business I had, Jim Bulger and Steve Flemmi were my partners always."
In order to avoid electronic eavesdropping, Weeks, Bulger and Flemmi discussed business during long walks in public places including Castle Island, a circular path in South Boston known as the Sugar Bowl, and Columbia Park, which was adjacent to the liquor store which served as one of Bulger's offices.
After drawing the ire of Bulger, the Boston Herald reporter Howie Carr was allegedly targeted for assassination by the Winter Hill Gang. Weeks claims to have been involved in a murder plot against Carr, positioning himself with a sniper rifle in a cemetery adjacent to Carr's home. According to Weeks, he "passed" on killing Carr when the reporter emerged from his house with his young daughter accompanying him.
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. To get to Jimmy, Stevie, and me, someone would have had to go through those four layers of insulation. The next afternoon, he was presented with a 29-count indictment under the Racketeer Influenced and Corrupt Organizations Act (RICO), which alleged extortion, money laundering and drug trafficking. The charges carried a potential sentence of life imprisonment. At first refusing to cooperate, Weeks was transferred to a Federal penitentiary in Rhode Island.
Government witness 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 confessed to being an accessory to five murders. Weeks also testified against two of Bulger's friends in law enforcement; FBI Special Agent John Connolly and Lieutenant Richard J. Schneiderhan of the Massachusetts State Police. Weeks' cooperation was critical in the conviction of Connolly. On March 22, 2004, Weeks was sentenced to six years in federal prison, including time served.
He was a star witness at Connolly's 2008 trial on state charges of murdering former World Jai Alai president Roger Wheeler, 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 and the two former colleagues came to blows.
In 2012, Weeks was interviewed by Kurt Sutter on the Discovery Channel's Outlaw Empires.
Weeks' third book, Hunted Down: The FBI's Pursuit and Capture of Whitey Bulger, was released on July 22, 2015.
Books Weeks, Kevin; Karas, Phyllis, Brutal: The Untold Story of My Life Inside Whitey Bulger's Irish Mob, William Morrow Paperbacks; Reprint edition (March 13, 2007). Weeks, Kevin; Karas, Phyllis, Where's Whitey?, Tonto Books, October 15, 2010. Weeks, Kevin; Karas, Phyllis, Hunted Down: The FBI's Pursuit and Capture of Whitey Bulger, Fracas Press, July 22, 2015.
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Important facts
People in Kevin Weeks's life
Named in this biography and alive at the same time
Contemporaries
People whose lives overlapped Kevin Weeks's
Frequently asked questions
Who is Kevin Weeks?
American mobster
When was Kevin Weeks born?
Kevin Weeks was born on 21 March 1956 in South Boston.
What is Kevin Weeks's occupation?
Kevin Weeks is an autobiographer.
What nationality is Kevin Weeks?
Kevin Weeks is American.
Sources & further reading
Cite this page
APA: Biography.guide. (2026). Kevin Weeks. https://biography.guide/kevin-weeks/
MLA: "Kevin Weeks." Biography.guide, https://biography.guide/kevin-weeks/.
Chicago: "Kevin Weeks." Biography.guide. https://biography.guide/kevin-weeks/.
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