Kevin “Two Weeks” Weeks

two weeksKevin “Two Weeks” Weeks

Nicknamed: “Two Weeks” Weeks, “Kevin Squeeks;

Address: 8 Pilsduski Way, Old Colony Housing Project, South Boston;

Quincy Shore Drive, Quincy, Massachusetts

Born; March 21, 1956, South Boston, Massachusetts

Association: Winter Hill Gang

No one was more closer to Boston mob kingpin James “Whitey” Bulger than Kevin “Two Weeks” Weeks, who always referred to Bulger as “Jimmy.”However in the end, even he would rat out the legendary crime boss, implicating Bulger in at least 10 murders and taking down FBI agent: Connolly who was Bulger’s friend, accomplice, and part of the Winter Hill Gang.

Southie- Outlaw Empires

Former Whitey Bulger Henchman Kevin Weeks on Greater Boston


Kevin “Two Weeks” Weeks was on the High School Swim Team, learned how to box, from his father and hung out on Southie’s street corners in the 1950s through the 1960s.Born to Margaret and John Weeks on march 21, 1956, during the Chinese Astrology year of the Monkey.Kevin Weeks was the fifth of six children raised by working-class parents at 8 Pilsduski Way in South Boston’s old Colony Housing project, the same cluster of red brick tenements where FBI agent John Connolly lived as a child.Weeks’s father, who trained prizefighters as a living, taught his three sons how to box and also encouraged them to do their best in School.Two of the boys would later graduate from Harvard University.


The other, Kevin would only make it through secondary school amid the turmoil of forced busing and desegregation.In 1976, Weeks took a job as a bouncer at Triple O’s bar on Broadway in South Boston.It was the scene of numerous violent acts which included among other things serial acts of murder and mayhem. It was a decision that would change his life for both good and evil.Located just a short walk from a subway station, the neighborhood bar was a popular hangout for members of the Winter Hill Gang, including gang leader James “Whitey” Bulger and his partner Stephen “The Rifleman” Flemmi.Within two years, Weeks began working part time as Bulger’s enforcer and driver.Weeks started his own loan sharking business, paying a portion of the proceeds to Bulger in a form of a tribute.

Working Full time:

By 1982, Weeks had quit his bouncer job to become a full-time mobster.Weeks became very familiar in the art of murder. On May 11, 1982, Weeks was staking out Anthony’s Pier 4 restaurant in the South Boston waterfront under Bulger’s orders, awaiting the appearance of former associate turned snitch Edward Brian Halloran, who was having dinner with his pal Michael Donahue, the son of a Boston Police Detective from South Boston.
Bulger was armed with information he received from FBI agents: Connolly et al., which warned Bulger that Halloran was giving the FBI information about Bulger concerning numerous murders and was refused the witness protection program due to FBI agent Connolly’s discredited his intelligence.As the two men drove out of the parking lot. Weeks radioed Bulger using the code “The balloon is in the air,” a reference to Halloran’s nickname “Balloonhead.”Within seconds, Bulger, wearing a brown afro wig and  mustache and carrying a 30. Caliber carbine, drove his souped up blue Chevrolet to the parking lot, along with a masked man armed with a Mac 10 machine gun equipped with a military silencer, fired a fuselage of bullets killed Donohue instantly and left their real target Halloran, the father of two, clinging to life long enough to identify one of his assailants as James Flynn, a Winter Hill associate.Flynn, who was tried and acquitted for the murders, remained a suspect for seventeen years until 1999, when Weeks, cooperating with investigators, identified the killer as Bulger Inc.The second murderer, who was wearing a mask at the time, has never been identified.

By the early 1980s, Weeks, described as “a surrogate son” to Bulger (although he would later cast their relationship as businessmen), was working as an enforcer for the Winter Hill Gang crew, collecting loans and bets from local businessmen and receiving tribute from loan sharks and bookmakers.Soon, Bulger and Flemmi  expanded their business into drug trafficking, with Weeks once again as the enforcer.

41N5p66aYOL._SY344_PJlook-inside-v2,TopRight,1,0_SH20_BO1,204,203,200_According to Weeks’s memoir, Brutal: The Untold Story of My Life Inside Whitey Bulger’s Irish Mob, Bulger began calling drug dealers from throughout the Boston area for meetings, at which he would tell them that he had been offered a contract on their life.He would then demand a large payoff not to kill them. it worked and Bulger and Flemmi was paid a substantial amount of money in the Millions for the ploy.Jimmy, Stevie and Weeks weren’t in the import business and weren’t bringing in the marijuana or the cocaine. We were in Bulger, Flemmi and Weeks were in the shakedown business,” Weeks would later write.”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 distributers such as Joe Murray whom paid hundreds of thousands to Bulger and Flemmi to operate in the New England area, all while unbeknownst to every one Bulger and Flemmi were protected FBI TOP ECHELON informants we later would discover as the PUBLIC RECORDS so supports.

In 1995, after Bulger was indicted and had disappeared thanks to a tipped he received from FBI agent: Connolly through his contacts in the FBI such as FBI agents: Buckley, Quinn, Callen, Newton, Ring, Morris etc, whom was then monitoring the federal grand jury to time when the indictments would be handed down, as a result New England Mob Boss Francis”Cadillac Frank” Salemme, James “Whitey” Bulger, and Stephen “The Rifleman” Flemmi was tipped off to the indictments by FBI agent: Connolly so that they could flee.Flemmi was late leaving as he was told he had a few days before the indictments were handed down, however the DEA and State Police though that they should arrest him early and hold him on a complaint, which would give them time before the actual indictment came down, Flemmi was arrested in the area of Faneuil Hall in Boston’s Quincy Market Section of Government Center.



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Enlighten Yourself… “Where the willingness is great, the difficulties cannot be great. ” ~Niccolò Machiavelli, The Prince

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