Winter Hill Gang

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The Winter Hill Gang is a loose confederation of organized crime figures in the Boston, Massachusetts, area. The gang members and leadership are predominantly Irish-American, and it is often referred to as an Irish Mob organization, though many prominent and influential Winter Hill Gang members have also been of Italian descent.^[1] The organization derives its name from the Winter Hill neighborhood of Somerville, Massachusetts, north of Boston. Among its members have been the notorious Boston gangsters Buddy McLean, Whitey Bulger, Howie Winter, Joseph McDonald, Johnny Martorano, Patrick Nee 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 given its name in the 1970s by journalists at the Boston Herald, but the name was hardly ever openly used as a reference to them. Winter Hill Gang members are alleged to have been involved with most typical organized-crime-related activities, but they are perhaps most known for fixing horse races in the northeastern United States and shipping weapons to the IRA.^[2] Twenty-one members and associates, including Winter, were indicted by federal prosecutors in 1979.^[3]

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.^[4]

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).^[5] McLaughlin was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside the local hospital.^[4] 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.^[4]

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. By the time the war finally ended, more than 60 men had been murdered throughout Boston and the surrounding area.

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 New York City, 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.

Historical leadership[]

Leaders[]

• 1955–1965: James "Buddy" McLean: Boss, killed 1965.^[6]
• 1965–1978: Howard "Howie" Winter: Boss, jailed in 1978, released in 2002, died in 2020
• 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^[7]

Notable Associates[]

• Stephen Flemmi: Whitey Bugler's partner who was arrested in 1994, currently serving a life sentence
• 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 and noted gunrunner; released from prison in 2000 and wrote the book A Criminal and an Irishman in 2006
• : An associate of Bulger who ran the drug trade in South Boston during the 1980s

Criminal activities[]

FBI surveillance photograph of the former Winter Hill Gang hierarchy in the 1980s. Mob boss James "Whitey" Bulger (right) and lieutenant Stephen Flemmi.

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) Notarangeli'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.^[4]

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, 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, Billy Shea, John Shea, Tim Connolly, Pat Linskey, 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.^[4]

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.^[8]

See also[]

• Black Mass
• Brotherhood
• Whitey Bulger
• Charlestown Mob
• John Connolly (FBI)
• The Departed
• Irish Mob
• Mullen Gang

References[]

External links[]

• 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 – Department of Justice press release