Winter Hill Gang

The Winter Hill Gang is a structured confederation of Boston, Massachusetts–area organized crime figures, who are predominantly of Irish and Italian descent. It derives its name from the Winter Hill neighborhood of Somerville, Massachusetts, north of Boston. Its members have included notorious Boston gangsters Buddy McLean, Whitey Bulger, Howie Winter, Joe McDonald, Johnny Martorano, and Stephen Flemmi. They were most influential from 1965 under the rule of McLean and Winter until the takeover led by Bulger in 1979.

The Winter Hill Gang
Founded byJames "Buddy" McLean
Founding locationSomerville, Massachusetts
Years active1955–1999
TerritoryNew England, Somerville, Massachusetts, South Boston and Miami
EthnicityIrish American and Italian American
Membership (est.)40–50
Criminal activitiesRacketeering, loan sharking, Skimming, murder, contract killing, race fixing, bribery, bookmaking, truck hijacking, robbery, illegal gambling, drug trafficking, money laundering, extortion, prostitution, weapons trafficking, and police corruption
AlliesMullen Gang
Provisional IRA
Patriarca crime family (under Raymond Patriarca)
RivalsCharlestown Mob
Patriarca crime family (specifically the Angiulos)

The Winter Hill Gang was given its name in the 1970s by journalists at the Boston Herald, although the name was hardly ever openly used as a reference to them. While Winter Hill Gang members are alleged to have been involved with most typical organized-crime-related activities, they are perhaps most known for fixing horse races in the northeastern United States and shipping weapons to the IRA.[1] Twenty-one members and associates, including Winter, were indicted by federal prosecutors in 1979.[2]

Irish Gang War

The Boston Irish Gang War started in 1961 and lasted until 1967. It was fought between the McLaughlin Gang of the Boston neighborhood of Charlestown, led by Bernie McLaughlin, and the Winter Hill Gang of Somerville, led by James "Buddy" McLean.[3]

The two gangs had co-existed in relative peace for a number of years 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 Petricone, Jr. (who fled the Boston area during the war and became an actor under the name Alex Rocco).[4] McLaughlin was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside the local hospital.[3] Bernie McLaughlin went to see "Buddy" 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 McLaughlin coming out of the "Morning Glory" bar in Charlestown in October 1961. This was the start of Boston's Irish Gang War.[3]

In 1965, McLean was shot and killed by one of the last survivors of the McLaughlin Gang, Steve Hughes. Howie Winter then assumed control of the Winter Hill Gang. One of the surviving McLaughlin brothers, nicknamed "Punchy", was shot while waiting for a bus in the West Roxbury section of Boston. A year later, in 1966, the last two associates of the McLaughlin Gang, brothers Connie and Steve Hughes were killed, allegedly by hitman Frank Salemme.

After the Irish Gang war, the Winter Hill Gang was reputed to be not only the top Irish Mob syndicate in the New England area, but along the entire east coast as well. In the book Black Mass by Dick Lehr and Gerard O'Neill, the authors make the unsubstantiated claim that the Winter Hill Gang were far more feared and powerful than their rivals, the Boston branch of the Patriarca crime family run by the Angiulo Brothers.

Criminal activities

During the 1970s, the gang's most prominent members were Howie Winter, John Martorano, James J. Bulger, Stephen Flemmi, Joseph McDonald and James Sims. 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 Joseph (Indian Joe) Notranagelli's crew. In what should have been a fabulously profitable illicit gambling enterprise, the gang lost it. As the years went by, James Bulger and Stephen 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, Howie Winter and John Martorano were going broke. Eventually they had to go to Patriarca family underboss Gennaro 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.

It was the decision to involve outsiders with their business that led to their downfall. By 1979, Howie Winter and the rest of the Somerville crew were all sent to prison for fixing horse races, leaving Whitey Bulger and Stephen Flemmi as the new leaders of the Winter Hill Gang. During the 1980s, Bulger's associates consisted of Kevin Weeks, Kevin O'Neil, Jim Mulvey and Patrick Nee. By 1991, even as James J. Bulger's criminal career was winding down, he remained the undisputed mob boss. His criminal associate Kevin Weeks was not considered a threat, and neither were Jim Mulvey, even though he suspected Bulger of being an FBI informant, John Shea, Tim Connolly, Eddie MacKenzie, Paul "Polecat" Moore or John Cherry. Boston journalist Howie 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 organised crime rackets, Bulger generated well over $25 million in racketeering proceeds alone throughout his criminal career, according to paperwork filed in federal court.

FBI informants

In 1998, during a trial for racketeering and fixing horse races, Steve Flemmi and Whitey Bulger were revealed under disclosure to be FBI informants. 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 Agent H. 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.[5]

Historical leadership


  • 1955–1965: James "Buddy" McLean: Boss, killed 1965.
  • 1965–1978: Howard "Howie" Winter: Boss, jailed in 1978, released in 2002.
  • 1978–1995: James "Whitey" Bulger: Boss, one of the most infamous Irish Mob bosses. Fled Boston in 1994 due to a pending federal indictment. He was on the FBI's Ten Most Wanted list until his arrest in Santa Monica, California on June 22, 2011. He had a $2 million bounty on his head. Killed in his cell at age 89 at USP Hazleton on October 30th 2018.
  • 1995–2000: Kevin Weeks: Boss, 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 entitled Brutal: The Untold Story of My Life Inside Whitey Bulger's Irish Mob

Notable associates

  • Stephen Flemmi: Whitey Bulger's partner who was also an FBI informant; he was arrested in 1994 and is currently serving life in prison
  • Johnny Martorano: was a high-ranking member and notorious contract killer, served twelve years in prison
  • Patrick Nee: former associate of Whitey Bulger and gunrunner, served ten years in prison for armed robbery
  • John "Red" Shea: former associate of the Winter Hill Gang and narcotics trafficker, served twelve years in prison for drug trafficking charges
  • Kevin O'Neil: former associate of the Winter Hill Gang who owned Triple O's Lounge, served one year in prison

Ties to the FBI

John Connolly was an FBI agent who served as a handler for Bulger and Flemmi while they were informants. He leaked information about investigations targeting Bulger and Flemmi, which in several cases led to informants being murdered. He was convicted of racketeering in 2002 and sentenced to 10 years in prison. He was convicted of state charges of second-degree murder in Florida for the death of John Callahan in 2008 and sentenced to 40 years in prison.

See also


  1. Finley, Bill. "The reverend's deal with the devil; Eddie Donnally crossed Boston mobsters and lived to tell about it". Retrieved October 4, 2013.
  2. Murphy, Shelley (July 22, 1998). "Howie Winter ever saw Bulger coming". The Boston Globe. Retrieved June 26, 2018.
  3. Howie Carr, The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century
  4. Teresa, Vincent. My Life in the Mafia.
  5. Howie Carr, Hitman: The Untold Story of Johnny Martorano: Whitey Bulger's Enforcer and the Most Feared Gangster in the Underworld
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