The Winter Hill Gang is a structured confederation of Boston, Massachusetts-area organized crime figures, predominantly Irish-American. It derives its name from the Winter Hill neighborhood of Somerville, Massachusetts north of Boston. Its members have included notorious Boston gangsters Howie Winter, James "Buddy" McLean, James J. "Whitey" Bulger, and hitmen John Martorano and Stephen "The Rifleman" 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 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.

Irish Gang War

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 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 Alex "Bobo" Petricone, Jr. (who fled the Boston area during the war and became an actor under the name Alex Rocco). McLaughlin was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside of the local hospital. 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 McLaughlin's 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. 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 allegedly killed by hitman Frank Salemne. 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, the Boston branch of the Patriarca crime family run by the Angiulo Brothers.

Productivity and overall success

The gang's most prominent members included Howie Winter and his bookkeeper Salvatore Sperlinga, brothers John Martorano, James J. Bulger and Stephen Flemmi. The gang's closest associates included George Kaufman, James Sims and Joseph MacDonald. 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 Notranageli'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 Patriarca family underboss 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. 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.

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 SA H. Paul Rico and then later by SA John "Zip" Connolly. They not only ratted out other gangs, but they did so to their own brothers of the Winter Hill Gang. When they had nothing to report to the FBI, they would make up information to ensure that they were seen to be of high value to them.

Historical leadership

1960s-1965 - James "Buddy" McLean - Boss, killed 1965.

1965-1978 - 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 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.

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

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