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The Winter Hill Gang is a loose confederation of
organized crime Organized crime (or organised crime) is a category of transnational, national, or local groupings of highly centralized enterprises run by criminals to engage in illegal activity, most commonly for profit. While organized crime is generally th ...
figures in the Boston, Massachusetts, area. The gang members and leadership are predominantly
Irish-American , image = Irish ancestry in the USA 2018; Where Irish eyes are Smiling.png , image_caption = Irish Americans, % of population by state , caption = Notable Irish Americans , population = 36,115,472 (10.9%) alone ...
and
Italian-American Italian Americans ( it, italoamericani or ''italo-americani'', ) are Americans who have full or partial Italian ancestry. The largest concentrations of Italian Americans are in the urban Northeast and industrial Midwestern metropolitan areas, w ...
descent. The organization itself derives its name from the Winter Hill neighborhood of
Somerville, Massachusetts Somerville ( ) is a city located directly to the northwest of Boston, and north of Cambridge, Massachusetts, Cambridge, in Middlesex County, Massachusetts, United States. As of the 2020 United States Census, the city had a total population of 81, ...
, north of Boston. Amongst its members several have been notorious Boston gangsters, such as
Buddy McLean James Joseph McLean (January 26, 1930 – October 31, 1965) was an American mobster boss, who was the original boss of the Somerville, Massachusetts-based Winter Hill Gang during the 1960s. McLean was well known throughout the Greater Boston ar ...
,
Whitey Bulger James Joseph "Whitey" Bulger Jr. (; September 3, 1929 – October 30, 2018) was an American organized crime boss who led the Winter Hill Gang in the Winter Hill neighborhood of Somerville, Massachusetts, a city directly northwest of Bos ...
,
Howie Winter Howard Thomas Winter (March 17, 1929 – November 12, 2020) was an American mobster. He was a leader of the Winter Hill Gang. Early life Winter was born in Boston, Massachusetts on March 17, 1929. He was of German and Irish descent. Winter die ...
, Joseph McDonald,
Johnny Martorano John James Vincent Martorano (born December 13, 1940; also known as "Vincent Joseph Rancourt", "Richard Aucoin", "Nick", "The Cook", "The Executioner", "The Basin Street Butcher") is an American former gangster and former hitman for the Winter Hi ...
,
Patrick Nee Patrick Joseph Nee (born December 22, 1944) is an Irish-American former mobster and Irish republican sympathizer. A former member of the Mullen Gang and the Winter Hill Gang, he is a Vietnam War veteran, and author of ''A Criminal and an Iri ...
and
Stephen Flemmi Stephen Joseph Flemmi (born June 9, 1934) is an American gangster and convicted murderer and was a close associate of Winter Hill Gang boss Whitey Bulger. Beginning in 1975, Flemmi was a top echelon informant for the Federal Bureau of Investig ...
. 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 The ''Boston Herald'' is an American daily newspaper whose primary market is Boston, Massachusetts, and its surrounding area. It was founded in 1846 and is one of the oldest daily newspapers in the United States. It has been awarded eight Pulit ...
'', 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 most well-known for fixing horse races in the
northeastern United States The Northeastern United States, also referred to as the Northeast, the East Coast, or the American Northeast, is a geographic region of the United States. It is located on the Atlantic coast of North America, with Canada to its north, the Southe ...
and shipping weapons to the
IRA Ira or IRA may refer to: *Ira (name), a Hebrew, Sanskrit, Russian or Finnish language personal name *Ira (surname), a rare Estonian and some other language family name *Iran, UNDP code IRA Law *Indian Reorganization Act of 1934, US, on status of ...
. 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 the Boston neighborhood of Charlestown, led by
Bernie McLaughlin Bernard McLaughlin (1921 – October 31, 1961) was an American gangster from Charlestown, Massachusetts, and leader of " The McLaughlin Brothers" gang. Early life Before Bernie formed his own crew he was a loan shark and enforcer for the Angi ...
, 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 Alexander Petricone, Jr. (who fled the Boston area during the war and became an actor under the name
Alex Rocco Alex Rocco (born Alessandro Federico Petricone Jr.; February 29, 1936 – July 18, 2015) was an American actor. Known for his distinctive, gravelly voice, he was often cast as villains, including Moe Greene in ''The Godfather'' (1972) and his Pr ...
). Teresa, Vincent. ''My Life in the Mafia''. McLaughlin was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside 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 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. 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 West Roxbury is a neighborhood in Boston, Massachusetts bordered by Roslindale and Jamaica Plain to the northeast, the town of Brookline to the north, the cities and towns of Newton and Needham to the northwest and the town of Dedham to the ...
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 Francis Patrick Salemme (August 18, 1933 – December 13, 2022), sometimes spelled Salemmi, also known as "Cadillac Frank" and "Julian Daniel Selig", was an American mobster from Boston, Massachusetts who became a hitman and eventually the boss ...
. 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 The Irish Mob (also known as the Irish mafia or Irish organized crime) is a collective of organized crime syndicates composed of ethnic Irish members which operate primarily in Ireland, the United States, Canada and Australia, and have been in ...
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 The Patriarca crime family (, ), also known as the New England Mafia, the Boston Mafia, the Providence Mafia, or The Office is an Italian-American American Mafia, Mafia crime family, family in New England. It has two distinct factions, one based ...
run by the Angiulo Brothers.


Historical leadership


Leaders

* 1955–1965:
James "Buddy" McLean James Joseph McLean (January 26, 1930 – October 31, 1965) was an American mobster boss, who was the original boss of the Somerville, Massachusetts-based Winter Hill Gang during the 1960s. McLean was well known throughout the Greater Boston ar ...
: Boss, killed 1965. * 1965–1978: Howard "Howie" Winter: Boss, jailed in 1978, released in 2002, died in 2020 * 1978–1995:
James "Whitey" Bulger James Joseph "Whitey" Bulger Jr. (; September 3, 1929 – October 30, 2018) was an American organized crime boss who led the Winter Hill Gang in the Winter Hill neighborhood of Somerville, Massachusetts, a city directly northwest of Bos ...
: 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 Santa Monica (; Spanish language, Spanish: ''Santa Mónica'') is a city in Los Angeles County, California, Los Angeles County, situated along Santa Monica Bay on California's South Coast (California), South Coast. Santa Monica's 2020 United Sta ...
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 30, 2018. * 1995–2000:
Kevin Weeks Kevin Weeks (born March 21, 1956) is an American former mobster and longtime friend and mob lieutenant to Whitey Bulger, the infamous boss of the Winter Hill Gang, a crime family based in the Winter Hill neighborhood in Somerville, Massachuset ...
: 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 Stephen Joseph Flemmi (born June 9, 1934) is an American gangster and convicted murderer and was a close associate of Winter Hill Gang boss Whitey Bulger. Beginning in 1975, Flemmi was a top echelon informant for the Federal Bureau of Investig ...
: Whitey Bugler's partner who was arrested in 1994, currently serving a life sentence *
Johnny Martorano John James Vincent Martorano (born December 13, 1940; also known as "Vincent Joseph Rancourt", "Richard Aucoin", "Nick", "The Cook", "The Executioner", "The Basin Street Butcher") is an American former gangster and former hitman for the Winter Hi ...
: Notorious contract killer and charter member of the gang, involved in 20 mob related killings, served 12 years in prison for murder *
Patrick Nee Patrick Joseph Nee (born December 22, 1944) is an Irish-American former mobster and Irish republican sympathizer. A former member of the Mullen Gang and the Winter Hill Gang, he is a Vietnam War veteran, and author of ''A Criminal and an Iri ...
: 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


Criminal activities

During the 1970s, the gang's most prominent members were
Howie Winter Howard Thomas Winter (March 17, 1929 – November 12, 2020) was an American mobster. He was a leader of the Winter Hill Gang. Early life Winter was born in Boston, Massachusetts on March 17, 1929. He was of German and Irish descent. Winter die ...
,
John Martorano John James Vincent Martorano (born December 13, 1940; also known as "Vincent Joseph Rancourt", "Richard Aucoin", "Nick", "The Cook", "The Executioner", "The Basin Street Butcher") is an American former gangster and former hitman for the Winter Hi ...
,
James J. Bulger James Joseph "Whitey" Bulger Jr. (; September 3, 1929 – October 30, 2018) was an American organized crime boss who led the Winter Hill Gang in the Winter Hill neighborhood of Somerville, Massachusetts, a city directly northwest of Bost ...
,
Stephen Flemmi Stephen Joseph Flemmi (born June 9, 1934) is an American gangster and convicted murderer and was a close associate of Winter Hill Gang boss Whitey Bulger. Beginning in 1975, Flemmi was a top echelon informant for the Federal Bureau of Investig ...
, 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 Underboss ( it, sottocapo) is a position within the leadership structure of certain organized crime groups, particularly in Sicilian, Greek, and Italian-American Mafia crime families. The underboss is second in command to the boss. The underbo ...
Gennaro Angiulo Gennaro Joseph "Jerry" Angiulo Sr. (; March 20, 1919 – August 29, 2009) was an American mobster who rose to the position of underboss in the Patriarca crime family of New England under Raymond L. S. Patriarca. Angiulo was convicted of racketeeri ...
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 Weeks (born March 21, 1956) is an American former mobster and longtime friend and mob lieutenant to Whitey Bulger, the infamous boss of the Winter Hill Gang, a crime family based in the Winter Hill neighborhood in Somerville, Massachuset ...
, Kevin O'Neil, and
Patrick Nee Patrick Joseph Nee (born December 22, 1944) is an Irish-American former mobster and Irish republican sympathizer. A former member of the Mullen Gang and the Winter Hill Gang, he is a Vietnam War veteran, and author of ''A Criminal and an Iri ...
. By 1991, even as James J. Bulger's criminal career was winding down, he remained the undisputed mob boss. His criminal associate
Kevin Weeks Kevin Weeks (born March 21, 1956) is an American former mobster and longtime friend and mob lieutenant to Whitey Bulger, the infamous boss of the Winter Hill Gang, a crime family based in the Winter Hill neighborhood in Somerville, Massachuset ...
was not considered a threat, and neither were Jim Mulvey, even though he suspected Bulger of being an FBI informant, Billy Shea,
John Shea John Victor Shea III ( ; born April 14, 1949) is an American actor, film producer and stage director. His career began on Broadway theatre, Broadway where he starred in ''Yentl (play), Yentl,'' subsequently winning his first major award, the 1975 ...
,
Tim Connolly Timothy L. Connolly (born May 7, 1981) is an American former professional ice hockey player who played eleven seasons in the National Hockey League (NHL) for the New York Islanders, Buffalo Sabres, and Toronto Maple Leafs. Playing career As a yo ...
, Pat Linskey, Eddie MacKenzie, Paul "Polecat" Moore or John Cherry. Boston journalist
Howie Carr Howard Louis Carr Jr. (born January 17, 1952) is an American conservative radio talk-show host, political author, news reporter and award-winning writer. He hosts ''The Howie Carr Show'' originating from his studios in Wellesley, MA and broadca ...
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. The Winter Hill Gang played a role in the Irish Republican Army's paramilitary actions in the late 20th century. In his novel, ''A Criminal and an Irishman'', Patrick Nee detailed the gang's involvement with the IRA. He said that Bulger "loved being associated with the IRA and the cause of Irish Freedom". He went on to say that Bulger's association with the IRA gave him a sense of legitimacy. Nee played an active role in raising funds and smuggling weapons to the IRA. In September of 1984, the Valhalla, a fishing boat, left Boston harbor loaded with weapons. The vessel was seized by two loyalist ships upon arriving in Ireland having been sold out by an Irish informant. The Winter Hill Gang also had a plot spoiled by a local fisherman John McIntyre who they had partnered with but who went to the police after hearing word of a gun-running mission. The authorities attempted to use McIntyre as an informant against Whitey Bulger. However, Whitey Bulger received information from FBI agent John Connolly that the fisherman had gone to the police. Connolly provided McIntyre's whereabouts and Whitey Bulger along with his right-hand man Stephen Flemmi tortured and killed him.


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 An informant (also called an informer or, as a slang term, a “snitch”) is a person who provides privileged information about a person or organization to an agency. The term is usually used within the law-enforcement world, where informan ...
. 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.


See also

* '' Black Mass'' * ''
Brotherhood Brotherhood or The Brotherhood may refer to: Family, relationships, and organizations * Fraternity (philosophy) or brotherhood, an ethical relationship between people, which is based on love and solidarity * Fraternity or brotherhood, a mal ...
'' *
Whitey Bulger James Joseph "Whitey" Bulger Jr. (; September 3, 1929 – October 30, 2018) was an American organized crime boss who led the Winter Hill Gang in the Winter Hill neighborhood of Somerville, Massachusetts, a city directly northwest of Bos ...
*
Charlestown Mob The Charlestown Mob was an Irish mob group in Charlestown, Boston, Charlestown, which figured prominently in the history of Boston, Massachusetts, Boston for much of the 20th century. The gang was headed by the McLaughlin brothers (Bernard " ...
* John Connolly * ''
The Departed ''The Departed'' is a 2006 American epic crime thriller film directed by Martin Scorsese and written by William Monahan. It is both a remake of the 2002 Hong Kong film ''Infernal Affairs'' and also loosely based on the real-life Boston Winter ...
'' *
Irish Mob The Irish Mob (also known as the Irish mafia or Irish organized crime) is a collective of organized crime syndicates composed of ethnic Irish members which operate primarily in Ireland, the United States, Canada and Australia, and have been in ...
*
Mullen Gang The Mullen Gang was an Irish-American gang operating in Boston. Gang members Paulie McGonagle (died November 1974) was a Boston mobster and onetime leader of the Mullen Gang, a South Boston street gang involved in burglary, auto theft, and a ...


References


External links


Reporting on "Whitey" Bulger and the Winter Hill Gang
'
The Boston Globe ''The Boston Globe'' is an American daily newspaper founded and based in Boston, Massachusetts. The newspaper has won a total of 27 Pulitzer Prizes, and has a total circulation of close to 300,000 print and digital subscribers. ''The Boston Glob ...
'' *
The Search for 'Whitey' Bulger
(story series). ''
The Boston Globe ''The Boston Globe'' is an American daily newspaper founded and based in Boston, Massachusetts. The newspaper has won a total of 27 Pulitzer Prizes, and has a total circulation of close to 300,000 print and digital subscribers. ''The Boston Glob ...
'' * {{Organized crime groups in America Irish-American organized crime groups Gangs in Massachusetts