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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.

Key Information

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.[1]

Early life

[edit]

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."[2]: xx–xi 

Criminal career

[edit]

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.[3]

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.[3] Meanwhile, Weeks turned to running a loansharking business on the side.

In 1982, 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.[3]

The Halloran murder

[edit]

On the night of May 11, 1982, Bulger was told of the whereabouts of a former associate turned federal informant, Brian Halloran, known on the streets as "Balloonhead" owing to the size of his cranium.[4] 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.[5] 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.[4]

Afterwards, Weeks calmly drove from the scene, even circling back to collect a hubcap. He then disposed of the guns used in the killings by throwing them into Marine Bay on the instructions of Bulger.[4] Weeks described the murders of Halloran and Donahue as the event which cemented his association with Bulger, saying: "I was involved in a double homicide, so I knew there was no getting out".[5]

Mob lieutenant

[edit]
FBI surveillance photo of Weeks (right) with Whitey Bulger (left)

Weeks became a protégé to Bulger, who groomed him as his successor and treated him like a son. During the 1980s, Weeks operated several convenience stores and liquor marts in South Boston that served as fronts for the Winter Hill Gang. He collected payments from loan sharks and bookmakers, insulating Bulger from the transactions, and also helped extort local criminals and businessmen who were behind on their debts to the gang.[6] Weeks said: "Everything I did, every business I had, Jim Bulger and Steve Flemmi were my partners always."[4]

In 1983, Weeks and O'Neil acquired Stippo's Liquor Mart in South Boston from owners Stephen and Julie Rakes by using threats of violence. The store was renamed South Boston Liquor Mart and became a frequent hangout of Bulger and Flemmi. In 1998, Stephen "Stippo" Rakes was convicted of perjury and obstruction of justice for telling grand juries that the sale of the liquor store was voluntary.[7]

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.[4][5]

Weeks was an accomplice in the murders of Deborah Hussey, Arthur “Bucky" Barrett, and John McIntyre.[8][9][10]

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.[11][12]

Narcotics

[edit]

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.[2]: 152 

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.[2]: 16 

Weeks also insists that Bulger strictly forbade PCP and selling to children,[2]: 179  and that those dealers who refused to play by his rules were violently driven out of the neighborhood.

In 1990, 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.[2]: 167 

Mob boss

[edit]

Bulger became a fugitive after he was indicted on racketeering charges in January 1995, and Weeks subsequently acted as "operational chief" of the Winter Hill Gang, taking orders from Bulger via frequent telephone calls.[7] Weeks funded Bulger by funnelling thousands of dollars into his bank account.[6] Weeks also 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."[2]: 247  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.[2]: 248 

Arrest

[edit]

On November 17, 1999, Weeks, O'Neil, and other Winter Hill associates were arrested in South Boston by agents of the DEA, the Massachusetts State Police and the Internal Revenue Service (IRS).[13] 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.[7] A 79-page affidavit by state police Lieutenant Thomas Duffy provided a broad outline of the activities of the Winter Hill Gang and listed various criminal acts committed by Weeks.[14] The charges carried a potential sentence of life imprisonment.[15] At first refusing to cooperate, Weeks was transferred to a Federal penitentiary in Rhode Island.

Government witness

[edit]

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".[16] 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."[2]: 261 

He was also unnerved when two lawyers told him 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.

Weeks negotiated a plea deal with federal prosecutors in 1999.[17] He confessed to being an accessory to five murders.[9] In 2000, Weeks led authorities to six different bodies buried by the Winter Hill Gang, including the triple grave of Hussey, McIntyre and Barrett, as well as a cache of weapons in Flemmi's home in South Boston. He implicated Bulger in the murder of Brian Halloran (nicknamed "Balloonhead" by Bulger), helped solve the 1981 contract killing of businessman Roger Wheeler, and agreed to testify against Flemmi and Bulger. He also revealed that Whitey's younger brothers, Senate President Billy Bulger and juvenile magistrate clerk Jackie Bulger, had talked with Whitey while he was on the lam. According to Weeks, Jackie had even helped Whitey get a fake ID which Weeks delivered to Whitey during a rendezvous in Chicago.

Jackie was sentenced to six months in federal prison for lying to a grand jury about his actions, while Billy was forced to resign as president of the University of Massachusetts.[18] 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.[17]

Family

[edit]

Kevin Weeks married his longtime girlfriend, Pamela Cavaleri (born 1957), on April 26, 1980 at the Gate of Heaven Roman Catholic Church in their native South Boston. They have two sons.

Current status

[edit]

Weeks was released from Federal prison in early 2005. He collaborated with journalist Phyllis Karas (of People magazine) to write Brutal: The Untold Story of My Life Inside Whitey Bulger's Irish Mob, Weeks's account of his life with Bulger and Flemmi, which was published in March 2006. The profits from the book were partially used to compensate victims as part of a civil suit against Weeks.[4] At the time of he book's release, Weeks was interviewed by correspondent Ed Bradley on 60 Minutes.[11]

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."[19]

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.[20][21]

In 2012, Weeks was interviewed by Kurt Sutter on the Discovery Channel's Outlaw Empires.[22]

Weeks' third book, Hunted Down: The FBI's Pursuit and Capture of Whitey Bulger, was released on July 22, 2015.[3]

[edit]

Actor Jesse Plemons portrayed Weeks in the 2015 film Black Mass.[23]

Books

[edit]
  • 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). ISBN 978-0061148064
  • Weeks, Kevin; Karas, Phyllis, Where's Whitey?, Tonto Books, October 15, 2010. ISBN 978-1907183164
  • Weeks, Kevin; Karas, Phyllis, Hunted Down: The FBI's Pursuit and Capture of Whitey Bulger, Fracas Press, July 22, 2015. ISBN 9780986216404

References

[edit]
[edit]
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Kevin Weeks

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Kevin Weeks (born March 21, 1956) is an American former associate who functioned as the primary enforcer and trusted lieutenant to James "Whitey" Bulger, the head of Boston's Irish-dominated . Recruited by Bulger in the early 1980s after working as a , Weeks managed collections for illegal bookmaking, oversaw rackets targeting liquor stores and construction firms, and participated directly in several gang-sanctioned killings, including the 1982 murders of Edward Bertolli and Arthur "Bucky" Barrett. After Bulger fled federal charges in December 1994, Weeks briefly attempted to maintain gang operations before his own arrest in January 1995 on racketeering and firearms offenses; he later faced additional murder indictments and, in 1999, entered a plea agreement that reduced his potential life sentence to 11 years in exchange for cooperating with prosecutors. As a government witness, Weeks provided critical testimony in Bulger's 2013 racketeering and murder trial, detailing the gang's operational structure and Bulger's personal involvement in at least 11 homicides, while also guiding authorities to the burial sites of six victims in South Boston. His disclosures contributed substantially to Bulger's conviction on 31 of 32 counts, including 11 murders, though Weeks' credibility was challenged by defense claims of his own violent history and motive to fabricate details for leniency. Released after serving five years, Weeks co-authored the 2006 memoir Brutal: The Untold Story of My Life Inside Whitey Bulger's Irish Mob, offering an insider account of the gang's dominance in Boston's underworld through intimidation and FBI-protected informant status.

Early Life

Upbringing in South Boston

Kevin Weeks was born on March 21, 1956, in , , a neighborhood renowned for its tight-knit Irish-American working-class communities. He grew up in the , one of the city's oldest developments built in the 1940s to accommodate low-income families amid post-World War II urban pressures. As the fifth of six children—preceded by older brother Billy and followed by his youngest sister Karen—Weeks experienced a household shaped by economic constraints typical of South Boston's blue-collar enclaves, where formal often took a backseat to practical survival skills. The Old Colony projects, located in the heart of Southie, embodied the area's blend of communal solidarity and hardship, with residents navigating poverty through informal networks and codes of loyalty that prioritized neighborhood ties over external institutions. This environment, marked by high concentrations of white working-class families in the and , instilled in youth like Weeks a reliance on physical strength and street savvy as defenses against daily adversities. and football emerged as key outlets for young men in such settings, channeling aggression into structured competition while reinforcing values of resilience and toughness. Weeks participated in these activities during his formative years, developing a reputation as a capable that honed his physicality in a where informal economies and peer enforcements often supplanted . The cultural fabric of , with its emphasis on family self-sufficiency amid limited opportunities, laid the groundwork for Weeks' early worldview, orienting him toward pragmatic, hands-on approaches rather than reliance on broader societal structures.

Association with the Winter Hill Gang

Initial Involvement

In the early 1970s, Kevin Weeks, a South Boston native with a background in Golden Gloves boxing, began associating with local organized crime figures through the Donald Killeen gang, a predominantly Irish outfit controlling much of the neighborhood's illicit activities including loan-sharking and gambling. Following Killeen's murder by members of the Italian-dominated Patriarca crime family in November 1972 amid escalating ethnic mob rivalries, Weeks aligned with James "Whitey" Bulger, who had been a key enforcer in the Killeen organization and subsequently consolidated power in South Boston by absorbing remnants of the defeated faction. By 1975, Weeks secured employment as a at Triple O's Lounge, a bar in that served as a hub for Bulger and associates to conduct collections and meetings. In this low-level capacity, he handled rowdy patrons and provided muscle for routine operations, leveraging his physical prowess to maintain order in an environment rife with debts and territorial disputes. This period coincided with broader instability in Boston's underworld, including inter-Irish conflicts between remnants of the and emerging alliances, as well as pressures from Italian syndicates seeking to encroach on Irish territories. The imprisonment of , the nominal leader of the Somerville-based , in 1979 on federal horse-race fixing charges created a that Bulger exploited to expand influence southward into Southie, drawing in reliable locals like Weeks through informal neighborhood networks rather than formal . Weeks' competence in barroom enforcement and demonstrated toughness in quelling disturbances earned initial notice from Bulger, marking his organic shift from street-level hustling to structured gang duties without immediate escalation to higher-risk endeavors.

Relationship with Whitey Bulger

Kevin Weeks, a South Boston native, first caught James "Whitey" Bulger's attention in the late 1970s while working as a at Triple O's, a bar frequented by Bulger and his associates in their shared neighborhood. Bulger, also from , recruited Weeks initially for enforcement duties, leveraging their common roots and Weeks' reputation as a tenacious . Over time, their professional interdependence grew, with Weeks evolving from a subordinate enforcer to a key operative involved in high-stakes activities, including murders starting in May 1982. Bulger groomed Weeks as a reliable successor, treating him with a level of trust akin to family, describing their bond as mentor-protégé and like an older brother. Their daily interactions were routine and intensive, with Weeks accompanying Bulger nearly every day for over two decades, handling tasks ranging from collections to violence as directed. Bulger's leadership emphasized ruthless pragmatism and discipline, avoiding alcohol, drugs, and gambling while dedicating efforts to criminal enterprises, often viewing killings as a release for stress. As Bulger's closest confidant, Weeks was privy to personal matters, including rare visits to Bulger's mother, underscoring the depth of trust. Bulger exhibited pronounced toward informants, routinely eliminating perceived "rats" to safeguard operations, a stance Weeks later highlighted in . Bulger's status as an FBI since the mid-1970s empirically facilitated operational leeway by providing advance warnings on and rival activities, though it coexisted with his informant suspicions toward others.

Criminal Operations

Racketeering and Extortion

Kevin Weeks served as a key enforcer for the Winter Hill Gang's operations, primarily through systematic targeting local businesses and illegal operations in during the 1980s and early 1990s. As Bulger's protégé, Weeks collected weekly tribute payments from bookmakers, imposing cuts of their profits under threat of physical harm to ensure compliance and maintain territorial control. These shakedowns extended to bars and liquor establishments, where the gang demanded protection money to operate without interference, leveraging their dominance in the neighborhood to deter resistance. Weeks employed tactics, including direct confrontations and assaults, to enforce payments; he testified that he would "sometimes beat somebody up" during collections from bookmakers who fell behind. In one instance, Weeks participated in the of a shortly after its 1984 opening, alongside Bulger and , securing approximately $67,000 from the owners in exchange for allowing the business to proceed. and ventures also faced pressure, as evidenced by disputes where Weeks and Bulger intervened in development projects, such as demanding adjustments to placements under implicit threats of disruption. These non-lethal enforcements, rooted in the gang's economic imperative to extract revenue without drawing excessive attention, underscored the causal role of credible violence threats in sustaining compliance across targeted sectors. The operations generated substantial illicit income, with individual extortions scaling into hundreds of thousands of dollars, as in the 1982 demand of $400,000 from businessman Michael Solimando, whom Weeks helped locate and pressure at a South Boston bar. By controlling access to lucrative rackets like gambling and leveraging neighborhood loyalty, the gang avoided overt federal scrutiny in the short term, though Weeks later detailed these activities in his 2006 memoir Brutal: My Life Inside Whitey's Irish Mob, confirming the reliance on fear over formal contracts.

Narcotics Distribution

In the early 1980s, Kevin Weeks, alongside James "Whitey" Bulger and Stephen Flemmi, expanded the Winter Hill Gang's operations into narcotics trafficking, focusing on cocaine and marijuana distribution in South Boston. The gang sourced cocaine through networks including Florida suppliers and intermediaries like Joe Towers, who facilitated weekly imports of 7 to 10 kilograms priced at $28,000 to $32,000 per kilo, while marijuana shipments involved large-scale smuggling, such as 30 tons via vessels like the Ramsland with a street value exceeding $30 million. Weeks managed street-level enforcement, collecting extortion payments from dealers—such as $12,000 from a cocaine distributor in 1988—and delivering product, including two kilograms of cocaine to local dealer Hobart Willis on Bulger's behalf. Bulger adopted a hypocritical policy toward narcotics, publicly condemning distribution in as a "dirty drug" associated with and health risks like AIDS, while prohibiting personal use among members and enforcing this through violence, such as expelling addicted associates or targeting non-compliant dealers. Despite this, the profited substantially from taxing importers and distributors, with Bulger reportedly earning around $10,000 weekly overseeing the trade in the mid-1980s and overall drug-related extortions contributing to his estimated $30–50 million in career gains. Weeks' role included shakedowns yielding tens of thousands from figures like Billy Shea, a key operator, though Bulger avoided direct trafficking to maintain deniability. Turf encroachments led to tensions with the Italian-American , particularly over drug markets in , as the challenged established boundaries without formal permission, exacerbating paranoia amid mutual suspicions of informants. Operations carried high risks, including federal surveillance like Operation Beans in 1985 and a major bust in August 1990 that arrested 51 dealers, prompting internal distrust and eliminations of perceived threats like John McIntyre, murdered on November 30, 1984, after cooperating on probes. These arrests eroded profits and intensified Bulger's vigilance, as independent dealers' independence undermined the gang's control.

Enforcer Duties and Murders

Kevin Weeks functioned as a primary enforcer for James "Whitey" Bulger within the Winter Hill Gang, executing violent intimidation and eliminations to safeguard criminal enterprises from rivals and informants. His duties escalated from physical confrontations and debt collections to direct participation in homicides, driven by the need to neutralize threats in a landscape marked by frequent betrayals to authorities. A pivotal instance occurred on May 11, 1982, when Weeks aided Bulger in the shooting deaths of Edward "Brian" Halloran and bystander Michael Donahue outside a restaurant. Halloran, suspected of providing FBI information on Bulger's role in the 1981 murder of Tulsa businessman Roger Wheeler, was tracked and ambushed; Bulger fired repeatedly into Halloran's body even after he collapsed, with Weeks positioned nearby to assist in the hit and subsequent evasion. The killings served to preempt testimony that could expose gang ties to out-of-state . Weeks later confessed to accessory roles in five murders during his 1999 plea agreement, encompassing participation in executions, body preparations—such as extracting teeth to hinder identification—and disposal of evidence, including firearms submerged in Dorchester Bay. These included the 1982 Halloran-Donahue slayings and others like the 1983 strangulation and shooting of safecracker Arthur "Bucky" Barrett, whom Bulger killed at a safehouse after interrogating him on stolen loot and informant risks; Weeks witnessed the act and helped conceal the remains. Similarly, he observed Bulger's 1984 murder of associate James "Joey" McIntyre via repeated gunshots to the head, motivated by fears of cooperation with investigators. Such enforcements relied on firearms for close-range shootings and post-kill protocols emphasizing rapid cleanup to evade detection, reflecting a strategy of decisive retaliation against snitching to preserve operational secrecy amid pervasive pressures. Weeks' framed these as essential defenses in a "snitch-heavy" , where unaddressed leaks imperiled the entire hierarchy.

Leadership and Downfall

Temporary Mob Leadership

Following Whitey Bulger's flight from on December 23, 1994, after receiving advance warning of his impending , Kevin Weeks stepped into the role of operational chief for the . As Bulger's longtime lieutenant and designated successor, Weeks directed the organization's surviving schemes targeting bookmakers and drug dealers, alongside ongoing narcotics distribution in . Initially, he maintained contact with the fugitive Bulger, receiving operational instructions via telephone to sustain core activities while evading intensifying federal scrutiny. Weeks' leadership occurred amid unprecedented pressure, as Bulger's disappearance prompted the FBI to dismantle the gang's informant protections and launch aggressive operations. Without Bulger's leverage as a protected source, the Winter Hill remnants faced rapid indictments of associates like in early 1995, shrinking their operational scope and forcing reliance on a diminished network of enforcers. Efforts to enforce collections through violence persisted, but these decisions exposed the group to further overextension, with territorial influence contracting as rival outfits encroached on vacated rackets. Internal fractures emerged as eroded under the strain, with members confronting heightened risks of or amid the power vacuum. Weeks navigated emerging betrayals within the ranks, where the absence of Bulger's authoritative oversight amplified and fragmented cohesion, contributing to the gang's progressive decline by mid-decade. This period underscored the Winter Hill Gang's dependence on Bulger's singular control, as Weeks' interim command yielded diminishing returns against mounting external and internal pressures.

Arrest and Surrender

Following James "Whitey" Bulger's flight from authorities in December 1994, the FBI intensified its pursuit of remnants, employing wiretaps, surveillance, and leveraging cooperating witnesses such as John Martorano, who began providing information in 1996 and implicated key figures. Mounting evidence from these efforts, including recordings of and activities, positioned Kevin Weeks as a primary target. On November 17, 1999, Weeks was arrested in alongside associates Kevin O'Neil and others by a of DEA agents, , and FBI, charged under RICO statutes with , , and tied to the gang's operations. The charges carried potential , prompting initial refusal to cooperate; Weeks was transferred to a federal penitentiary in . In January 2000, amid overwhelming evidence and the calculus of rather than remorse—as detailed in Weeks' own accounts—he opted to surrender information to authorities, leading investigators to unmarked graves containing victims' remains and initiating plea negotiations. This decision facilitated swift asset seizures, including cash, properties, and vehicles linked to illicit gains, as part of the federal forfeiture process.

Cooperation with Law Enforcement

Plea Deal and Testimony

In November 1999, following his arrest, Kevin Weeks entered into a plea agreement with federal prosecutors, pleading guilty to and accessory after the fact to five murders committed by the . In exchange for his cooperation, which included providing detailed information on gang operations and leading authorities to burial sites of victims, Weeks received a sentence of 11 years but served only five years due to good time credits and the value of his testimony, with release in 2004. His disclosures facilitated the recovery of physical remains from a secret gravesite at 799 East Third Street in , including those of victims such as Deborah Hussey and John McIntyre, which provided forensic corroboration for murder investigations previously reliant on . Weeks' testimony proved instrumental in securing convictions against several associates, including FBI agent John J. Connolly Jr., whom he implicated in tipping off the gang about investigations, leading to Connolly's 2002 conviction on and other charges (later including a 2008 conviction). His cooperation also pressured , Bulger's longtime partner, to plead guilty in 2003 to and multiple , avoiding a where Weeks would have testified against him. Weeks appeared in at least five trials related to the Bulger organization, detailing , narcotics trafficking, and homicides, which dismantled remaining gang networks by corroborating informant accounts with specifics like code words used in hits and financial ledgers. During James "Whitey" Bulger's 2013 federal trial, Weeks delivered key on Bulger's direct involvement in at least five murders, including the 1982 of Brian Halloran and Michael Donahue, where he described Bulger as the shooter firing from a vehicle, and the stranglings and shootings of Arthur "Bucky" Barrett and John McIntyre in a residence. He recounted Bulger's methods, such as using in one killing and burying bodies in the home's , with the recovered remains matching his descriptions and linking Bulger to 11 of the 19 murders charged. This testimony, combining personal observation with physical evidence, bolstered the prosecution's narrative of Bulger's operational control and contributed to his conviction on November 14, 2013, on 31 of 32 counts, including and enabling the killings.

Revelations on FBI Corruption

In testimony during James "Whitey" Bulger's 2013 racketeering trial, Kevin Weeks described how FBI Special Agent John Connolly relayed advance warnings to Bulger about potential cooperators and investigations, allowing the to preemptively eliminate risks. Connolly specifically informed Bulger that Brian Halloran, a low-level criminal, had approached federal authorities with details implicating Bulger in murders tied to an extortion case, prompting Bulger to orchestrate Halloran's shooting on May 11, 1982, in which bystander Michael Donahue was also killed as the vehicle pursued Halloran. Weeks recounted a December 23, 1994, meeting with Connolly in a liquor store cooler, where the agent disclosed an imminent indictment against Bulger and , enabling Bulger's flight from four days later and evading capture for 16 years. Bulger's tenure as an FBI informant, officially from 1975 until his termination in 1990 amid suspicions of ongoing criminality, permitted the agency to forgo prosecuting the gang's , of at least 20 businesses, narcotics trafficking, and involvement in roughly 10 murders during that span, as Bulger's tips on the rival Patriarca family's operations aligned with the FBI's focus on dismantling Italian-American syndicates. Weeks maintained that Bulger concealed this informant relationship from associates like himself, a disclosure that surfaced publicly around 1997 and which Weeks characterized as a personal betrayal, since the gang had relied on presumed law enforcement sources for protection rather than direct federal collaboration, sustaining their dominance over Boston's for over 15 years.

Post-Release Life

Imprisonment and Parole

Kevin Weeks was arrested in November 1999 and held in federal custody pending his cooperation with authorities. On March 22, 2004, he was sentenced to a total of six years' imprisonment for and related offenses, with credit for since his arrest, resulting in approximately two additional years to complete the term. He served his sentence in federal medium-security facilities, during which no significant disciplinary incidents were publicly reported, reflecting a relatively low-profile incarceration consistent with his status as a cooperating witness. Weeks was released from in 2005 after serving the full six-year term. His supervised release included standard federal conditions such as restrictions on associating with known criminals and requirements for regular reporting to officers. During a 2006 book signing event promoting his Brutal, Weeks publicly acknowledged having contemplated resuming upon release but ultimately abstained, citing a deliberate choice to maintain a lawful lifestyle amid ongoing temptations from his past. Post-release adaptation to civilian life proved challenging for Weeks, as his status exposed him to potential retaliation from former associates and other figures, necessitating heightened personal security measures and a low public profile outside controlled appearances. Despite these threats, he complied with terms without reported violations, transitioning to non-criminal pursuits while emphasizing rehabilitation in interviews, though his statements often retained a tone of unrepentant reflection on prior mob involvement rather than full .

Public Appearances and Reflections

In a March 2006 interview on with correspondent , Weeks reflected on his tenure as James "Whitey" Bulger's enforcer, describing Bulger's approach to violence as a form of "stress relief" and portraying mob killings as devoid of glamour or justification, emphasizing the cold pragmatism of survival in . Weeks reiterated this unvarnished perspective on violence during his October 17, 2022, testimony in the civil trial of Frederick Weichel, who sued for wrongful imprisonment in a 1980 Braintree conviction; Weeks provided an based on his firsthand knowledge of Bulger's operations, noting Bulger's disdain for Weichel but affirming the absence of involvement in the crime, without romanticizing the era's criminality. Following Bulger's fatal beating by inmates at USP Hazelton on October 30, 2018, Weeks offered no public expressions of for his former associate, consistent with his prior characterizations of Bulger as ruthlessly decisive in , while his with authorities stemmed from pragmatic self-interest amid the gang's collapse rather than ethical awakening. As of 2025, Weeks has maintained a low public profile post-release, with sporadic media engagements—such as a May 2025 discussion on the Irish Mob's downfall and Bulger's flight—focused on factual dissection of dynamics and organizational failures, alongside no reported arrests or significant legal entanglements.

Personal Life

Family Dynamics

Kevin Weeks married Pamela Cavaleri on April 26, 1980. The couple had two sons, Kevin Barry Weeks and Brian Weeks. Weeks' deep involvement in the Winter Hill Gang's operations, including and , required extensive secrecy that strained familial bonds, as he concealed criminal proceeds and activities to shield his wife and children from direct repercussions and rival threats. No members faced prosecution in connection with his criminal enterprises. After his 2005 release from , Weeks prioritized reconnection, emphasizing in a 2014 interview that his life had simplified with his sons actively involved and a supportive partner. He later married Anna Weeks, who has publicly reflected on the broader effects of South Boston's mob era on local through co-authored works.

Current Activities and Residence

Following his in July 2006 after serving approximately five years of an 11-year sentence, Kevin Weeks returned to , where he has resided in the area. He has maintained a low public profile, with no documented involvement in criminal enterprises or arrests since release, emphasizing disengagement from his former associations. As of , at age 69, Weeks engages in occasional media interviews reflecting on his past, such as a appearance in April 2024 discussing the era. These activities align with his post-incarceration focus on writing and selective commentary, while avoiding the spotlight to ensure personal security amid lingering risks from prior mob ties. No public reports indicate health impairments or new controversies affecting his routine.

Publications and Media

Authored Books

Brutal: The Untold Story of My Life Inside 's Irish Mob, co-authored with Phyllis Karas and published by on March 13, 2007, chronicles Weeks' recruitment into the in the 1970s, his roles in rackets generating over $1 million annually, sharking at rates exceeding 10% weekly , and participation in at least five murders ordered by James " between 1981 and 1994. The 336-page exposes Bulger's paranoia-driven , including the 1982 strangulation of a and the 1994 of rival gang members John McIntyre and Tommy King, while attributing the gang's endurance to Bulger's status with the FBI, which shielded operations from federal interference until 1994. Weeks portrays the enterprise as a profit-maximizing network reliant on fear enforcement rather than ideological loyalty, critiquing Bulger's self-aggrandizing persona as detached from the routine brutality of collections and body disposals in remote quarries. In Where's Whitey?, co-authored with Karas and self-published by FAL Enterprises on November 4, 2011, Weeks delivers a 279-page fictional thriller modeled on Bulger's 16-year evasion post-1994 flight, featuring a protagonist mirroring Bulger's nomadic existence across 20 aliases and locations from to . Drawing from Weeks' firsthand observations of Bulger's adaptability—such as using cash-only transactions and consultations—the narrative depicts causal pressures like betrayals and inter-gang vendettas forcing constant relocation, culminating in a hypothetical capture scenario. Unlike pure speculation, the book incorporates verifiable details like Bulger's affinity for fitness regimens and aversion to digital trails, positioning it as a semi-autobiographical lens on logistics over romanticized myths. Both volumes function as empirical records of mid-20th-century racketeering, prioritizing operational mechanics—like armored truck heists yielding $1.5 million in 1990—over heroic narratives, though Weeks' admissions of in his 2000 plea deal invite scrutiny of selective recollections favoring self-preservation. Independent reviews affirm their utility for dissecting informant-enabled persistence, contrasting with academic sources prone to downplaying agency in favor of systemic excuses. No additional solo-authored works by Weeks appear in publisher catalogs as of 2025. In the 2015 biographical crime film Black Mass, directed by Scott Cooper, Kevin Weeks is portrayed by Jesse Plemons as a key enforcer in James "Whitey" Bulger's Winter Hill Gang, emphasizing his role in violent operations and his eventual decision to cooperate with authorities after Bulger's 1994 disappearance. The depiction traces Weeks' transformation from loyal associate—handling hits like the 1982 murder of Brian Halloran alongside Bulger and Stephen Flemmi—to informant, culminating in his 1996 testimony that implicated Bulger in 19 killings. Weeks publicly dismissed the film's accuracy, describing it as "pure " and a "fantasy" that invented storylines and interactions among gang members, despite acknowledging the real murders committed. He specifically critiqued Plemons' portrayal for failing to resemble him physically and for misrepresenting his close relationships with Bulger and Flemmi, whom he trusted deeply until his in 1995. While illustrates FBI agent John Connolly's corrupt alliance with Bulger—allowing the gang to operate with impunity in exchange for intelligence on rivals—the narrative has been faulted for understating systemic bureau complicity, such as overlooked tips on Bulger's activities and broader institutional failures exposed in Weeks' later accounts. This artistic compression prioritizes interpersonal drama over the full evidentiary record of FBI oversight lapses documented in congressional hearings post-1995. Weeks appears in Bulger-focused true-crime biographies and series, such as adaptations drawing from Dick Lehr and Gerard O'Neill's : The Irish Mob, the FBI, and a Devil's Deal (2000), where he embodies the reluctant betrayer —framed as breaking the mob's loyalty code through his plea agreement, though often with less emphasis on the gang's internal fractures that precipitated his flip. These portrayals contrast factual trial records, which detail Weeks' specific admissions to participating in nine murders, against dramatized motives portraying him as more conflicted than the evidence suggests.

Controversies and Legacy

Disputes Over Testimony Credibility

During James "Whitey" Bulger's 2013 federal , defense attorney J.W. Carney Jr. aggressively cross-examined Weeks, portraying him as inherently untrustworthy due to his criminal history and plea agreement, which reduced his potential life sentence for and to commit to 11 years, of which he served five before in 2004. Carney highlighted Weeks' admissions of lifelong deception, prompting Weeks to retort, "I've been lying my whole life. I'm a criminal," underscoring the defense's argument that his against Bulger—implicating him in at least 11 —was motivated by rather than truth. Similar credibility attacks occurred in Weeks' earlier against former FBI agent John Connolly in 2008, where defense counsel questioned inconsistencies in Weeks' accounts of events tied to protections. Specific disputes arose over Weeks' recounting of murder motives and details, such as the 1982 killings of Brian Halloran and Michael Donahue, where Weeks testified Bulger fired the fatal shots after Halloran sought , but defense probing revealed potential variances with other cooperators like , who described overlapping but not identical sequences of events and rationales, including gang turf disputes versus threats. Critics, including Bulger's legal team, alleged Weeks tailored narratives to align with prosecutorial needs for his deal, pointing to his initial non-cooperation post-arrest in 1999 before flipping. These challenges were countered by tangible corroboration: in 2000, Weeks guided investigators to burial sites yielding remains of victims like Deborah Hussey and , aligning with his descriptions and bolstering prosecutorial cases independent of his word alone. Juries credited his testimony alongside physical evidence and other witnesses, leading to Bulger's conviction on 31 of 32 counts, including participation in 11 murders, with no successful appeals overturning verdicts on credibility grounds. Nonetheless, public and media discourse has sustained skepticism, with some attributing lingering doubts to the informant system's incentives for , though empirical trial outcomes affirm the testimony's role in securing upheld convictions.

Broader Implications of Informant Programs

The FBI's designation of James "Whitey" Bulger as a Top Echelon from to 1990 prioritized intelligence against the Italian-American , enabling Bulger and associates like Kevin Weeks to evade scrutiny for violent acts, including at least 19 murders attributed to Bulger during this period. This protection stemmed from handlers like John Connolly providing tips on investigations, allowing the to eliminate rivals and witnesses without federal intervention, as unsolved homicides piled up amid the agency's focus on targets. Empirical data from Bulger's 2013 indictment and trial revealed how informant privileges deferred accountability, fostering a causal chain where street-level enforcement yielded to strategic gains against larger syndicates, ultimately permitting unchecked lethality. Weeks' post-arrest cooperation in the 2000s, including testimony that corroborated Bulger's status and agent leaks, precipitated Connolly's federal conviction for shielding figures, highlighting systemic in informant oversight. This exposure prompted internal FBI reforms, such as stricter guidelines on informant authorization and monitoring enacted after , yet it underscored ethical pitfalls: top-level criminals as assets risked inverting priorities, where protections insulated ongoing predation rather than curbing it. Critics, drawing from ional probes, argue such programs erode institutional trust by incentivizing corruption and , as agents prioritized informant utility over public safety, leading to prolonged impunity for high-volume offenders. Proponents of informant strategies contend they yielded net justice by dismantling networks in —contributing to over 100 convictions in the and —outweighing isolated abuses, per FBI assessments of disruptions. However, the Bulger case illustrates drawbacks outweighing benefits when applied to apex predators: causal realism reveals that shielding violent kingpins for tactical edges amplified harm, as evidenced by decades-delayed prosecutions and public disillusionment with federal integrity, without commensurate safeguards against handler capture. This tension questions the programs' long-term efficacy, favoring first-principles accountability over deferred, -dependent outcomes.

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