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Winter Hill Gang

The Winter Hill Gang was a loose confederation of organized crime figures in the Boston, Massachusetts, area. It was generally considered an Irish Mob organization, with most gang members and the leadership consisting predominantly of Irish-Americans, though some notable members, such as Johnny Martorano, are of Italian-American descent.[1]

Founded by

1955–2000

New England, Somerville, Massachusetts, South Boston and Miami

Predominantly Irish American with some Italian American members

100+ (1980s)

Racketeering, loan sharking, assault, murder, bribery, fraud, theft, robbery, illegal gambling, drug trafficking, money laundering, corruption, extortion, prostitution, weapons trafficking

The organization itself derives its name from the Winter Hill neighborhood of Somerville, Massachusetts, north of Boston.[2] Amongst its members several have been notorious Boston gangsters, such as Buddy McLean, Whitey Bulger, Howie Winter, Joseph McDonald, 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 is 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 best known for fixing horse races in the northeastern United States and shipping weapons to the IRA.[3] Twenty-one members and associates, including Winter, were indicted by federal prosecutors in 1979.[4]

Irish Gang War[edit]

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.[5]


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


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 was far more feared and powerful than their rivals, the Boston branch of the Patriarca crime family run by the Angiulo Brothers.

1955–1965: : Boss, killed 1965.[7]

James "Buddy" McLean

1965–1978: : Boss, jailed in 1978, released in 2002, died in 2020

Howard "Howie" Winter

1978–1995: : 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 the night after he was transferred USP Hazleton on October 30, 2018.

James "Whitey" Bulger

1995–2000: : 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[8]

Kevin Weeks

FBI informants[edit]

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.[11]

Black Mass

Brotherhood

Whitey Bulger

Charlestown Mob

John Connolly

The Departed

Irish Mob

Mullen Gang

Reporting on "Whitey" Bulger and the Winter Hill Gang

The Boston Globe

(Press release). Drug Enforcement Administration. Archived from the original on February 25, 2007 – via Illinois Police and Sheriff's News (IPSN).

"Winter Hill Gang Leader Flemmi Pleads Guilty"