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Boston’s Winter Hill Gang

Boston’s Winter Hill Gang
By
John William Tuohy

TheWinter Hill Gang took its name from the Winter Hill neighborhood of Somerville, Massachusetts north of Boston. Its members have included notorious Boston gangsters Howie Winter ("Howie"), James McLean ("Buddy"), James J. Bulger ("Whitey"), and hitman Stephen Flemmi ("The Rifleman"). 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 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. Twenty-one members and associates, including Winter, were indicted by federal prosecutors in 1979. Winter Hill no longer exists in its original state.

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

The two gangs had co-existed in relative peace for a number of years until an incident on Labor Day weekend 1961. While at a party, Georgie McLaughlin made an advance on the girlfriend of Winter Hill Gang member Alex Rocco.

 He was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside of the local hospital. Bernie McLaughlin went to see James 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, Massachusetts in October 1961. This was the start of Boston's Irish Gang War.

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. A year later, in 1966, the last two associates of the McLaughlin Gang, brothers Connie and Steve Hughes, were killed.

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 east coast as well. In the book Black Mass, by Dick Lehr and Gerard O'Neill, the authors claimed that the Winter Hill Gang were far more feared and powerful than their rivals in the New England Mafia, run by the Angiulo Brothers. The Angiulo Family of the North End was responsible for most of the Italian mafia operations in Boston and points north. They answered to the Patriarca crime family of Rhode Island.

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 Steven 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 Gennaro Anguilo 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. 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 John Shea, Eddie Mac, "Polecat" Moore or John Cherry. Howie Carr comments, "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.

Leaders of the Winter Hill Gang

1960s-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 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.

1995-2000 - Kevin Weeks - Boss, was Bulger's lieutenant, he was arrested on November 15, 
1999 and becoming 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.

2000–2009 - George "Georgie Boy" Hogan –Alleged Boss of the Winter Hill Mob, (Headquarters in South Boston)

Members of the Winter Hill Gang

Salvatore Sperlinga ("Sal") - Howie Winter's lieutenant and bookkeeper, killed in 1980.
Johnny Martorano - Top hitman for James Bulger & Flemmi, indicted and arrested 1995, became an informant in 1999, sentenced to 14 years in 2004, with time served released 2007. He is half Italian-American and half Irish-American.

Edward “Teddy” Deegan - Bank robber and associate of Stevie Flemmi.

Patrick Nee - Associate of Bulger's with close ties to the Provisional Irish Republican Army, arrested in 1990 by the FBI, but was released after April 2000. Now works in South Boston.

Anthony D'Agostino ("Tony Blue") - Buddy McLean's bodyguard, with McLean at Peppermint Lounge in Somerville when he was killed 1965.

Thomas Ballou, Jr. ("Tommy") - Buddy McLean's driver and bodyguard. He was killed in 1970.

Joseph McDonald ("Joe Mac") - An original member of the gang. McDonald was a hitman, World War II veteran and street fighter. FBI's Top Ten Most Wanted List until he was arrested by the FBI before he could turn himself in. The FBI received information on his whereabouts from Whitey Bulger. He died in 1997 after being released from prison.

Alexander Federico Petricone Jr. ("Bobo") - It was Petricone's girlfriend on Labor Day weekend of 1961 that McLaughlin hit winter Hill and the Charlestown gangs. The following year Petricone moved to California and changed his name to Alex Rocco, acting in the film The Godfather as well as nearly 200 other movie and television roles from 1965 to present.

Russell Nicholson - was an original member of the gang as well as a police officer. He reportedly was the driver during the 1961 gangland slaying of Bernie McLaughlin and subsequently fired by the police force shortly thereafter. He was later kidnapped and killed in retaliation by the Charlestown Gang (McLaughlin Bro's) in 1964.

James Simms ("Jimmy") - Released from prison in 1986, his Whereabouts are unknown.

Mike Iavello - (narcotics, alleged) left Boston area for Florida.

John Shea AKA Red – Alleged known associate and narcotics dealer for the gang.

Vincent Teresa - became an FBI informant against the Patriarca crime family after he was arrested in 1967. He wrote the book My Life in the Mafia, although he was never inducted into La Cosa Nostra.

John "Mick" Murray - Irish-American gangster and professional Bank Robber from the Boston neighborhood of Charlestown. Reputed to have ties with organized crime in Montreal, and the Irish Republican Army. Murray was also implicated along with South Boston gangster Pat Nee with planning a series of gun shipments to the Irish Republican Army. Plead guilty and was sentenced to nine years in federal prison on July 1,2002 to embezzlement, extortion, racketeering and theft for shaking down a Southie bookmaker, stealing computer equipment from UPS trucks and attempting to defraud the union pension and welfare fund.

Ballou Tommy, Jr. A former longshoreman and member of the Winter Hill Gang , and former bodyguard and driver to Buddy McLean. Ballou was  murdered in Charlestown, Mass. 1970.

Louis Litif - was recruited by Bulger for extra muscle in the 1970s and a suspect in the 1978 Black friars Massacre.

Anthony Veranis - local boxer who was murdered by John Martorano in 1966.

George W. Holden - professional welterweight boxer and small time criminal.

Timothy A. Connolly 3rd - was a soldier for Bulger until becoming an informant in 1989, owned the Corner Cafe

James M. Murphy - was on Boston Police Department's "Most Wanted List".

Dennis Horkenbach ("Blumpkin") – Alleged known associate.

Ronnie Fronduto - former associate.

Jimmy Flynn –Alleged, was a soldier who later became an actor.

Tommy McKinnon – Alleged known associate.


Edward "Eddie Mac" MacKenzie, Jr- Alleged enforcer and narcotics dealer for the gang, co-author and subject of the book: "Street Soldier: My Life as an Enforcer for Whitey Bulger and the Irish Mob."

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