TheWinter Hill Gang was a loose confederation of Americanorganized crime figures in theBoston, Massachusetts area. It was generally considered anIrish mob organization, with most gang members and the leadership consisting predominantly ofIrish-Americans, although some notable members, such asStephen Flemmi andJohnny Martorano, were ofItalian-American descent.^[4] The organization itself derives its name from theWinter Hill neighborhood ofSomerville, Massachusetts, north of Boston.^[5] The Winter Hill Gang was given its name in the 1970s by journalists at theBoston Herald.

The Winter Hill Gang was involved with most typical organized crime-related activities, including drug trafficking, gambling, and loan sharking,^[5] as well as fixing horse races throughout thenortheastern United States,^[6] and shipping weapons to theProvisional Irish Republican Army (IRA).^[7] Twenty-one members and associates, including Winter, were indicted by federal prosecutors in 1979.^[8]

The Winter Hill Gang was the second most powerful criminal organization inNew England, behind only thePatriarca crime family ofProvidence, Rhode Island.^[9] Amongst its members several have been notorious Boston gangsters, such asJames "Buddy" McLean,James "Whitey" Bulger,Howie Winter,Joseph "Joe Mac" McDonald,Patrick Nee,Kevin Weeks and Stephen Flemmi. They were most influential from 1965, under the rule of McLean and Winter, to the 1979 takeover led by Bulger.

The Winter Hill Gang was founded in 1961 byJames "Buddy" McLean andHowie Winter, who were partners in a trucking company, when they became involved inillegal gambling,numbers running,bookmaking andloansharking in theWinter Hill neighborhood ofSomerville, Massachusetts, a northwestern suburb ofBoston.^[10] The Winter Hill Gang co-existed in relative peace with theMcLaughlin Gang from the Boston neighborhood ofCharlestown, led byBernie, Georgie andEdward "Punchy" McLaughlin, until an incident atSalisbury Beach onLabor Day weekend 1961. While at a party, Georgie McLaughlin made an advance on the girlfriend of Winter Hill Gang member Alexander "Bobo" Petricone, Jr.^[11] McLaughlin was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside the local hospital.^[12] Bernie McLaughlin went to see McLean and demanded that he hand over the members of the gang who beat his brother. McLean refused. The McLaughlins took this refusal as an insult and attempted to wire a bomb to McLean's wife's car.^[12]

In retaliation, McLean shot and killed Bernie McLaughlin coming out of the "Morning Glory" bar in Charlestown on October 31, 1961. This was the start of Boston's first Irish Gang War.^[12] McLean and Petricone, his alleged getaway driver, were arrested and charged with McLaughlin's murder but, as none of the numerous witnesses to the killing were willing to testify, they were released. Petricone fled the Boston area during the war and became an actor under the nameAlex Rocco.^[10]

Although the McLaughlin brothers had a larger and more well-established gang, the Winter Hill Gang proved more dynamic and resourceful, recruiting killers such asStephen "the Rifleman" Flemmi,Francis "Cadillac Frank" Salemme, andJoseph "the Animal" Barboza. Their rivals, meanwhile, suffered another significant setback when Georgie McLaughlin was sent to prison for life after shooting and killing a bank teller during an argument at a christening in an incident unrelated to the gang war.^[10]

The Winter Hill Gang made their first attempt on the life of the remaining brother, "Punchy" McLaughlin, after being tipped off that he was in the Hotel Beaconsfield, shotgunning him at point-blank range when he entered a car and blowing his jaw off. He survived after being rushed to theBeth Israel Hospital. In the second attempt, McLaughlin was ambushed by Winter, who was armed with a scoped.308 Winchester rifle, along with McLean, Flemmi and Salemme, who each carried a machine gun, as he arrived at a girlfriend's house inWeston. Winter blew McLaughlin's hand off with a rifle shot, but McLaughlin was able to flee and escaped after a car chase alongRoute 128.^[10] The Winter Hill Gang finally succeeded in killing McLaughlin when they shot him while he waited for a bus in theWest Roxbury section of Boston on October 20, 1965.^[12] The one-handed McLaughlin was carrying a pistol in a satchel but was unable to draw the gun quickly enough to save himself.^[10]

Eleven days later, on October 31, 1965, McLean was shot and killed by one of the last survivors of the McLaughlin Gang, Steve Hughes, as he exited the 318 Club in Winter Hill.^[12] Winter then assumed control of the Winter Hill Gang.^[9] A year later, in 1966, the last two associates of the McLaughlin Gang, brothers Connie and Steve Hughes were killed, allegedly by Salemme.^[12] Connie Hughes was ambushed on theNortheast Expressway after leaving anafterhours club on May 25, 1966, and Stevie Hughes was killed along with an associate in a drive-by shooting onRoute 114 inMiddleton on September 23, 1966.^[13] The murders of the Hughes brothers marked the conclusion of the first Irish Gang War, with the Winter Hill Gang victorious despite the death of McLean.^[10] By the time the war finally ended, more than 60 men had been murdered throughout Boston and the surrounding area.^[12] Irish gang killings had become so prevalent in Boston that the obituaries sections in newspapers were jokingly referred to as "the Irish sports pages".^[10]

The second Irish Gang War in Boston began in the mid-1960s and was contested between theMullen Gang and theKilleen Gang. Unlike the Winter Hill and McLaughlin gangs, which were city-wide organizations, the Mullens and Killeens were confined toSouth Boston and their feud essentially amounted to a local turf war.^[14] The Mullens were a loose-knit street gang with around 60 members, while their rivals were a smaller but more organized group led by the Killeen brothers, Donnie, Kenny and Eddie.^[15] The younger Mullens, whose ranks included manyVietnam War veterans,^[10] began encroaching on the territory of the Killeens, who had been the dominant gang in South Boston for two decades.^[16]

The Mullen–Killeen feud escalated significantly after an incident in 1969 in which Kenny Killeen bit off the nose of Mullen Gang member Mickey Dwyer in a bar fight at the Transit Café.^[14] Afterwards, a murder attempt was made on Mullen leaderPatrick "Pat" Nee, whose gang retaliated by killing Killeen enforcerBilly O'Sullivan on March 28, 1971.^[10] The gang war nominally ended when Killeen leaderDonald Killeen was gunned down outside his home inFramingham on May 13, 1972.^[17] Killeen's death leftJames "Whitey" Bulger in charge of the gang.^[9] Outnumbered, the Killeens agreed to negotiate with the Mullens, and a meeting between the gangs, which was mediated by Winter, was held at Chandler's bar in Boston'sSouth End. The Mullens and Killeens agreed to cease hostilities and consolidate under the leadership of Winter.^[15]

During the 1970s, the Winter Hill Gang's most prominent members were Winter, Flemmi, Bulger,John "the Executioner" Martorano,Joseph "Joe Mac" McDonald, and James "Jimmy" Sims.^[12] The gangsters used the office of Marshall Motors, a large body shop on Marshall Street in Somerville, as their social club and headquarters.^[18] Having emerged from the gang wars as the preeminent Irish-American crime group in Boston, the Winter Hill Gang controlled the city'sIrish mob rackets under the strict supervision of thePatriarca crime family ofProvidence, Rhode Island.^[9] The Winter Hill Gang entered into an alliance with the family when Patriarca underbossGennaro "Gerry" Angiulo enlisted the gang for assistance in a war against the Somerville-based Notarangeli gang, headed by Alfred "Indian Al" Notarangeli.^[19][20]

Notarangeli's gang had began extorting bookmakers who were under the protection of the Patriarca family,^[21] and while on furlough from prison in 1972, Notarangeli murdered one of Angiulo's bookies, Paulie Folino.^[20][22] The Winter Hill Gang began exterminating members of the Notarangeli gang.^[23] Explaining how the Winter Hill Gang differed from the Patriarca family in their methods of killing, Flemmi described the Winter Hill Gang as "hunters" who tracked down their targets, while theMafia would wait, possibly for years, for their intended victim to show up onHanover Street to kill them.^[24]

On March 8, 1973, Michael Milano, a bartender, was machine gunned to death in theBrighton neighborhood of Boston after Martorano mistook him for Notarangeli.^[19] Milano's friend, Louis Lapiana, and Lapiana's girlfriend, Dianne Sussman, were also wounded in the shooting.^[25] The Winter Hill Gang made another attempt to kill Notarangeli on March 19, 1973, when the car in which he was traveling was fired upon by Martorano and Winter in Boston'sNorth End.^[26] Notarangeli survived unharmed.^[19] Two of his associates, Frank Capizzi and Hugh "Sonny" Shields, were injured.^[27] Notarangeli's driver, Albert "Bud" Plummer, died from his wounds, on March 23, 1973.^[28]

On March 24, 1973, William "Billy" O'Brien was killed when Martorano strafed his car with machine gun fire onMorrissey Boulevard in an attempt to murder another Notarangeli gang member, Ralph DeMasi,^[19][23] who survived being shot eight times.^[25] Another of Notarangeli's associates, James Leary, was shot dead while in hiding inFort Lauderdale, Florida, on April 3, 1973.^[29] On April 18, 1973, Joseph "Indian Joe" Notorangeli, the brother of Al Notorangeli, was shot and killed by Martorano in a restaurant inMedford Square.^[22][26]

After fleeing to theWest Coast, Notarangeli returned to Boston in late 1973 in an attempt to make peace with Angiulo. Notarangeli paid $50,000 to Angiulio, who shared the money with the Winter Hill Gang.^[20] On February 22, 1974, Notarangeli was shot in the head by Martorano and left in the trunk of his car.^[30][31]

Following the merger of the Mullen and Killeen gangs into the Winter Hill Gang, several former Mullen members resented the amalgamation and continued to seek revenge against their former Killeen rivals. Winter sanctioned the murders of any members who were deemed subversive.^[32]Paul "Paulie" McGonagle, who sought retaliation against former Killeen Gang member Bulger for the killing of his brother and who rivaled Bulger for control of rackets in South Boston, was murdered on November 20, 1974.^[30][33] His body was buried at Tenean Beach inDorchester.^[34]

The Winter Hill Gang was quite proficient at murdering rival mobsters in order to take over their rackets. But once they gained control, they had no idea how to run them. They learned the lesson of their gang's disastrous foray into gambling after wiping out Notarangeli's crew. In what should have been a fabulously profitable illicit gambling enterprise, the gang lost it. As the years went by, Bulger and Flemmi lost interest in running any kind of gambling operation. They would eventually only provide protection for bookmakers, drug dealers and truck hijackers. By 1975, Winter and Martorano were going broke. Eventually they had to go to Angiulo to borrow money. To make the weekly payments, they began going into businesses with people they didn't know and couldn't trust. These activities included rigging horse races and drug trafficking.^[12]

In 1975, the Winter Hill Gang was allegedly on the verge of a mob war with the Patriarca family in a dispute over the placement ofvending machines around theGreater Boston area.^[8] The Organized Crime Program of the Boston division of theFederal Bureau of Investigation (FBI) focused on the Patriarca family as their main priority, considering the Winter Hill Gang a lesser threat,^[35] and recruited Bulger and Flemmi into the FBI's Top Echelon Informant program.^[36] Bulger and Flemmi began providing information on the Mafia in exchange for protection from the FBI.^[37]

The Winter Hill Gang became involved in a horse race-fixing scheme when Winter and Martorano partnered withAnthony "Fat Tony" Ciulla, a hustler from theNorth End of Boston, and his associate, Billy Barnoski, beginning in 1974. The gangsters would successfully place large wagers with bookmakers throughout the country on unfancied race horses after swaying betting odds in their favor by bribing and threatening jockeys and doping horses.^[1] The Winter Hill Gang made millions of dollars by fixing races along theEast Coast, and became the second most influential crime group inNew England, behind only the Patriarca family.^[9] The gang partnered with mobsters from theGenovese,Bruno andTocco–Zerilli crime families in infiltrating race courses in Massachusetts, New York, Pennsylvania, Maryland, and Michigan.^[3]

It was the Winter Hill Gang's decision to involve outsiders with their business that led to their downfall.^[12] After being arrested, Ciulla began cooperating with federal authorities and informing on the gang.^[1] In February 1979, 21 members and associates, including Winter, were indicted by federal prosecutors after being implicated by former business partners in connection with a million-dollar horse race-fixing scheme.^[8][37] Bulger's and Flemmi's status as confidential FBI informants kept them from being indicted.^[8][38] When Winter and the rest of the Somerville crew were all sent to prison, Bulger and Flemmi were able to assume control as the new leaders of the Winter Hill Gang.^[12][37]

In 1979 and 1980, Bulger used Lancaster Foreign Motors, a parking garage in Boston'sWest End owned by Winter Hill Gang associate George Kaufman, as the gang's headquarters, where he openly met with and accepted payments from associates.^[39] After putting the garage under surveillance for six months, theMassachusetts State Police were granted a warrant to plant covert listening devices on the premises in the summer of 1980.^[40] Bulger's allies in the FBI alerted him to the police surveillance,^[41] and he and Flemmi subsequently began operating from South Boston.^[39] In November 1980, Bulger and Flemmi helped the FBI plant a bug in the headquarters of Jerry Angiulo in theNorth End.^[37] Angiulo and a number of his associates were indicted in 1983 and later convicted, allowing the Winter Hill Gang to take over the rackets that had been controlled by the Patriarca family.^[42]

During the 1980s, Bulger's associates consisted ofKevin Weeks,Kevin O'Neil, andPatrick Nee. By 1991, even as James J. Bulger's criminal career was winding down, he remained the undisputed mob boss. His criminal associateKevin Weeks was not considered a threat, and neither were Jim Mulvey, even though he suspected Bulger of being an FBI informant, Billy Shea,John Shea,Tim Connolly, Pat Linskey, Eddie MacKenzie, Paul "Polecat" Moore or John Cherry. Boston journalistHowie Carr commented, "They hadn't really been gangsters so much as they'd been ex-boxers and bar-room brawlers who had become cocaine dealers." One problem that arose with the gang was that they enjoyed partaking in their own vices. Like their customers, they spent afternoons in the fall drinking beer and watching professional football on television, often doubling up wagers on late West Coast games as they desperately tried to break even and chased their losses. Despite the above unsubstantiated claims of the gang's apparent inability to successfully run organized crime rackets, Bulger generated well over $25 million in racketeering proceeds alone throughout his criminal career, according to paperwork filed in federal court.^[12]

The Winter Hill Gang played a role in the Irish Republican Army'sparamilitary actions in the late 20th century. In his novel,A Criminal and an Irishman, Patrick Nee detailed the gang's involvement with the IRA. He said that Bulger "loved being associated with the IRA and the cause of Irish Freedom".^[43] He went on to say that Bulger's association with the IRA gave him a sense of legitimacy. Nee played an active role in raising funds and smuggling weapons to the IRA. In September of 1984, theValhalla, a fishing boat, left Boston harbor loaded with weapons.^[43] The vessel was seized by twoIrish Naval Service ships upon arriving in Ireland having been sold out by an Irish informant. The Winter Hill Gang also had a plot spoiled by a local fisherman John McIntyre who they had partnered with but who went to the police after hearing word of a gun-running mission.^[44] The authorities attempted to use McIntyre as an informant against Whitey Bulger. However, Whitey Bulger received information from FBI agent John Connolly that the fisherman had gone to the police. Connolly provided McIntyre's whereabouts and Whitey Bulger along with his right-hand man Stephen Flemmi tortured and killed him.^[44]

In 1998, during a trial for racketeering and fixing horse races, Steve Flemmi and Whitey Bulger were revealed under disclosure to be FBIinformants. Steve Flemmi and Whitey Bulger were implicated in many unlawful activities, including murder, but were never brought to justice due to their FBI handlers diverting their guilt onto others in the gang or various other gangs of the time. They were first handled by Special AgentH. Paul Rico and then later by SA John "Zip" Connolly. In addition to providing details on other gangs, Flemmi and Bulger relayed information on fellow members of the Winter Hill Gang to the FBI. When they had nothing to report, they would make up information to ensure that they were seen to be of high value to the agency.^[45]

• 1961–1965 –James "Buddy" McLean – Murdered on October 31, 1965.^[46]
• 1965–1978 –Howard "Howie" Winter – Jailed in 1978, released in 2002, died in 2020
• 1978–1995 –James "Whitey" Bulger – One of the most infamous Irish Mob bosses. Fled Boston in 1994 due to a pending federal indictment. He was on the FBI'sTen Most Wanted list until his arrest inSanta Monica, California, on June 22, 2011. He had a $2 million bounty on his head. Killed in his cell at age 89 the night after he was transferredUSP Hazleton on October 30, 2018.
• 1995–2000 –Kevin Weeks – Was Bulger's lieutenant, he was arrested on November 17, 1999 and became a cooperating witness in January 2000; released from federal prison on February 4, 2005, he wrote a book in 2006 entitledBrutal: The Untold Story of My Life Inside Whitey Bulger's Irish Mob^[47]

• William "Billy" Barnoski – Barnoski was a Winter Hill Gangenforcer.^[48] He was convicted in 1984 on federal charges related to illegal sports betting.^[49] Upon his release from prison, Barnoski was given permission by the gang to take over the operations ofLowell bookmaker John "Jackie" McDermott.^[48] In May 1987, Barnoski, McDermott and 15 others were indicted on federal gambling-racketeering charges stemming from an illegal gambling operation.^[50] After learning that McDermott had began cooperating against him, Barnoski killed John McDermott and wounded his son, Peter McDermott, at their home on May 10, 1988. He was convicted of murder and attempted murder, and sentenced to life in prison on June 27, 1989.^[48] Barnoski developed a brain tumor in prison.^[51] He died from MRSA and sepsis at aLeominster hospital aged 74 on September 9, 2013.^[48]
• Phil Costa – Costa was an underling andgofer of Stephen Flemmi who acted as abagman and tended bar atafterhours clubs. One at least one occasion during the 1980s, he deliveredquicklime to Flemmi and James Bulger as they buried a murder victim in aSouth Boston home. Costa died in 1999.^[52]
• Stephen Flemmi – Whitey Bulger's partner who was arrested in 1994, currently serving a life sentence.
• Vincent "Jimmy the Bear" Flemmi – The older brother of Stephen Flemmi, Vincent Flemmi was a hitman andFBI informant. He was a fugitive for three years after escaping prison in 1975. Flemmi died of a drug overdose inNorfolk State Prison on October 16, 1979.^[53]
• George Kaufman – Kaufman owned a series of garages, including those on Marshall Street inSomerville and Lancaster Street in Boston'sWest End, which were used as Winter Hill Gang headquarters. He was indicted along with other gang members in January 1995. Mortally ill, Kaufman died in April 1995.^[54]
• Johnny Martorano – Notorious contract killer and charter member of the gang, involved in 20 mob related killings, served 12 years in prison for murder.
• Patrick Nee – An associate of Bulger and Weeks andgunrunner; released from prison in 2000 and wrote the bookA Criminal and an Irishman in 2006.
• Charles G. "Charlie" Raso – Raso was a bookmaker originally partnered with Joe Notorangeli, who was killed by the Winter Hill Gang in 1973. He then began working with James Bulger, Steve Flemmi and John Martorano.^[55] He also laundered money for Martorano.^[56]
• James L. "Jimmy" Sims – Sims was a founding member of the Winter Hill Gang. He was involved in the gang's horse race-fixing scheme and went on the run in 1977 to avoid state charges. Sims was imprisoned after being captured inKey West, Florida in 1982. He disappeared following his release fromWalpole State Prison in 1987.^[57]

This list isincomplete; you can help byadding missing items.(February 2025)

• Black Mass
• Brotherhood
• The Departed

• Lehr, Dick; O'Neil, Gerard (2000).Black Mass: Whitey Bulger, the FBI, and a Devil's Deal. New York City: PublicAffairs.ISBN 9781782116240.
• Weeks, Kevin; Karas, Phyllis (2006).Brutal: The Untold Story of My Life Inside Whitey Bulger's Irish Mob. New York City: HarperCollins.ISBN 9780061122699.

• Reporting on "Whitey" Bulger and the Winter Hill Gang – The Boston Globe
  • The Search for 'Whitey' Bulger (story series).The Boston Globe
• "Winter Hill Gang Leader Flemmi Pleads Guilty" (Press release).Drug Enforcement Administration. Archived fromthe original on February 25, 2007 – via Illinois Police and Sheriff's News (IPSN).

• Winter Hill Gang
• 1961 establishments in Massachusetts
• 2000 disestablishments in Massachusetts
• Federal Bureau of Investigation controversies
• Gangs in Boston
• Gangs in Florida
• Irish-American culture in Boston
• Irish-American organized crime groups
• Organizations established in 1961
• Organizations disestablished in 2000
• Somerville, Massachusetts
• South Boston

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