The Winter Hill Gang was a federation of Irish-American organized crime figures in the Boston, Massachusetts, area. The organization itself derives its name from the Winter Hill neighborhood of Somerville, Massachusetts, north of Boston. The Winter Hill Gang was given its name in the 1970s by journalists at the Boston Herald. The gang formed in Somerville under the leadership of Howard "Howie" Winter and James "Buddy" McLean. It was generally considered an Irish mob organization, with most gang members and the leadership consisting predominantly of Irish-Americans, although some notable members, such as Stephen Flemmi and Johnny Martorano, were of Italian-American descent.
After vanquishing the McLaughlin Gang of Charlestown, then absorbing the remnants of the Mullen and Killeen gangs of South Boston following a series of Irish gang wars, the Winter Hill Gang was most influential from 1965, under the rule of McLean and Winter, to the 1979 takeover led by James "Whitey" Bulger. Twenty-one members and associates were indicted by federal prosecutors in 1979. Subsequently, Bulger and Flemmi seized control of the gang, relocating its headquarters to South Boston.Whitey Bulger and the Lancaster Street Garage The West End Museum Several other infamous Boston gangsters, such as Joseph "Joe Mac" McDonald, Patrick "Pat" Nee, Vincent "Jimmy the Bear" Flemmi, and Kevin Weeks, were among its members.
The Winter Hill Gang was the second most powerful criminal organization in New England, behind only the Patriarca crime family of Providence, Rhode Island.The Irish Mob in Boston Boston University The gang was involved with most typical organized crime-related activities, including drug trafficking, gambling, and loan sharking, as well as fixing horse races throughout the northeastern United States, and shipping weapons to the Provisional Irish Republican Army (IRA).
History The Irish Gang Wars
The Winter Hill Gang was founded in 1961 by James "Buddy" McLean and Howard "Howie" Winter, who were partners in a trucking company, when they became involved in illegal gambling, numbers running, bookmaking and loansharking in the Winter Hill neighborhood of Somerville, Massachusetts, a northwestern suburb of Boston. The Winter Hill Gang co-existed in relative peace with the McLaughlin Gang from the Boston neighborhood of Charlestown, led by Bernie, Georgie and Edward "Punchy" McLaughlin, until an incident at Salisbury Beach on Labor Day weekend 1961. While at a party, Georgie McLaughlin made an advance on the girlfriend of Winter Hill Gang member Alexander "Bobo" Petricone, Jr.Teresa, Vincent. My Life in the Mafia. McLaughlin was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside the local hospital. 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.
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. 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 name Alex Rocco.
Although the McLaughlin brothers had a larger and more well-established gang, the Winter Hill Gang proved more dynamic and resourceful, recruiting killers such as Stephen "the Rifleman" Flemmi, Francis "Cadillac Frank" Salemme, and Joseph "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.
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 the Beth 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 in Weston. Winter blew McLaughlin's hand off with a rifle shot, but McLaughlin was able to flee and escaped after a car chase along Route 128. The Winter Hill Gang finally succeeded in killing McLaughlin when they shot him while he waited for a bus in the West Roxbury section of Boston on October 20, 1965. The one-handed McLaughlin was carrying a pistol in a satchel but was unable to draw the gun quickly enough to save himself.
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. Winter then assumed control of the Winter Hill Gang. A year later, in 1966, the last two associates of the McLaughlin Gang, brothers Connie and Steve Hughes were killed, allegedly by Salemme. Connie Hughes was ambushed on the Northeast Expressway after leaving an afterhours club on May 25, 1966, and Stevie Hughes was killed along with an associate in a drive-by shooting on Route 114 in Middleton on September 23, 1966.Confessions of a Loan Shark City Journal (Autumn 2021) 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. By the time the war finally ended, more than 60 men had been murdered throughout Boston and the surrounding area. Irish gang killings had become so prevalent in Boston that the obituaries sections in newspapers were jokingly referred to as "the Irish sports pages".
The second Irish Gang War in Boston began in the mid-1960s and was contested between the Mullen Gang and the Killeen Gang. Unlike the Winter Hill and McLaughlin gangs, which were city-wide organizations, the Mullens and Killeens were confined to South Boston and their feud essentially amounted to a local turf war. 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.Investigators: Bulger Killed Former Rival Gang Member Following Altercation WCVB-TV (August 9, 2011) The younger Mullens, whose ranks included many Vietnam War veterans, began encroaching on the territory of the Killeens, who had been the dominant gang in South Boston for two decades.Meet Whitey Bulger, the Notorious Crime Boss Who Went into Hiding Danielle Kugler, The Archive ( October 1, 2021)
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. Afterwards, a murder attempt was made on Mullen leader Patrick "Pat" Nee, whose gang retaliated by killing Killeen enforcer Billy O'Sullivan on March 28, 1971. The gang war nominally ended when Killeen leader Donald Killeen was gunned down outside his home in Framingham on May 13, 1972.Officers recall 1972 mob hit at Framingham home Ian B. Murphy, The MetroWest Daily News (June 24, 2011) Killeen's death left James "Whitey" Bulger in charge of the gang. 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's South End. The Mullens and Killeens agreed to cease hostilities and consolidate under the leadership of Winter.
The Indian War Following the elimination of the McLaughlin gang and the consolidation of the Mullen and Killeen gangs, the Winter Hill Gang controlled Boston's Irish mob rackets. During the 1970s, the gang's most prominent members were Winter, Flemmi, Bulger, John "the Executioner" Martorano, Joseph "Joe Mac" McDonald, and James "Jimmy" Sims. The gangsters used the office of Marshall Motors, a large body shop on Marshall Street in Somerville, as their social club and headquarters.Somerville’s current polyamorous people are much, much nicer than the Winter Hill Gang Kevin Cullen, The Boston Globe (March 28, 2023)
In January 1973, the Winter Hill Gang entered into a partnership with the Patriarca crime family of Providence, Rhode Island to control gambling rackets in Boston. Shortly afterwards, Gennaro "Jerry" Angiulo, the Patriarca family underboss and head of the family's Boston faction, enlisted the Winter Hill Gang for assistance in a war against a small gang based in Somerville led by Alfred "Indian Al" Notarangeli.Testimony: Rival Gang Leader Killed After Altercation With Patriarca Crime Family WCVB-TV (August 9, 2011) The Notarangeli gang had begun extorting bookmakers who were under the protection of the Patriarca family,James ‘Whitey’ Bulger linked to 11 murders CNN (August 12, 2013) and while on furlough from prison in 1972, Notarangeli murdered one of Angiulo's bookies, Paulie Folino.Joe Notarangeli, 1937-1973 Howie Carr, Boston Herald (May 22, 2011) The Winter Hill Gang subsequently began exterminating members of Notarangeli's gang.John Martorano: Rival Gang Member Killed In Notrangeli Gang Extermination WCVB-TV (August 9, 2011) Explaining how the Winter Hill Gang differed from the Patriarca family in their methods of killing, Flemmi described the gang as "hunters" who tracked down their targets, while the Mafia would wait, possibly for years, for their intended victim to show up on Hanover Street to kill them.Carr: If you”re a gangster, it helps to be two-faced Howie Carr, Boston Herald (November 17, 2018)
On March 8, 1973, Michael Milano, a bartender, was machine gunned to death in the Brighton neighborhood of Boston after Martorano mistook him for Notarangeli.Trail of corpses and grief Boston Herald (June 2, 2013) Milano's friend, Louis Lapiana, and Lapiana's girlfriend, Dianne Sussman, were also wounded in the shooting.Survivor recalls night of terror in 'Whitey' Bulger trial Scott Malone, Reuters (June 20, 2013) 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's North End.Alleged Bulger victim tells of ambush The Boston Globe (June 22, 2013) Notarangeli survived unharmed. Two of his associates, Frank Capizzi and Hugh "Sonny" Shields, were injured.Alleged Bulger victim describes 1973 attack: ‘A firing squad hit us’ Shelley Murphy, Milton J. Valencia and Martin Finucane, Boston.com (June 21, 2013) Notarangeli's driver, Albert "Bud" Plummer, died from his wounds, on March 23, 1973.Bulger Accused Of Orchestrating Ambush That Killed Andover Man WCVB-TV (August 9, 2011)
On March 24, 1973, William "Billy" O'Brien was killed when Martorano strafed his car with machine gun fire on Morrissey Boulevard in an attempt to murder another Notarangeli gang member, Ralph DeMasi, who survived being shot eight times. Another of Notarangeli's associates, James Leary, was shot dead while in hiding in Fort Lauderdale, Florida, on April 3, 1973.Man Shot To Death In Restaurant The Recorder (April 19, 1973) On April 18, 1973, Joseph "Indian Joe" Notorangeli, the brother of Al Notorangeli, was shot and killed by Martorano in a restaurant in Medford Square.