Winter Hill Gang
Encyclopedia
The Winter Hill Gang is a structured confederation of Boston, Massachusetts-area organized crime
Organized crime
Organized crime or criminal organizations are transnational, national, or local groupings of highly centralized enterprises run by criminals for the purpose of engaging in illegal activity, most commonly for monetary profit. Some criminal organizations, such as terrorist organizations, are...

 figures, predominantly Irish-American with a small Italian-American faction. It derives its name from the Winter Hill
Winter Hill, Somerville, Massachusetts
Winter Hill is a neighborhood in Somerville, Massachusetts. The neighborhood gets its name from the 120-foot hill that occupies its landscape, the name of which dates back to the 18th century...

 neighborhood of Somerville, Massachusetts
Somerville, Massachusetts
Somerville is a city in Middlesex County, Massachusetts, United States, located just north of Boston. As of the 2010 census, the city had a total population of 75,754 and was the most densely populated municipality in New England. It is also the 17th most densely populated incorporated place in...

 north of Boston. Its members have included notorious Boston gangsters Howie Winter
Howie Winter
Howard Thomas "Howie" Winter is an American mobster. He was the second leader of the infamous Winter Hill Gang.-Early life:...

 ("Howie"), James McLean ("Buddy"), James J. Bulger ("Whitey"), and hitman Stephen Flemmi
Stephen Flemmi
Stephen Joseph "The Rifleman" Flemmi is an Italian-American mobster and close associate of Winter Hill Gang boss James J. Bulger. Beginning in 1965, Flemmi was a top echelon informant for the Federal Bureau of Investigation...

 ("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
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...

. Twenty-one members and associates, including Winter, were indicted by federal prosecutors in 1979. Winter Hill no longer exists in its original state.

Irish Gang War

The Boston Irish Gang War started in 1961 and lasted until 1967. It was fought between the McLaughlin Gang
Charlestown Mob
The Charlestown Mob was an Irish Mob group in Charlestown, which figured prominently in the history of Boston for much of the 20th century....

 of Charlestown
Charlestown, Massachusetts
Charlestown is a neighborhood of Boston, Massachusetts, United States, and is located on a peninsula north of downtown Boston. Charlestown was originally a separate town and the first capital of the Massachusetts Bay Colony; it became a city in 1847 and was annexed by Boston on January 5, 1874...

, led by Bernie McLaughlin and the Winter Hill Gang of Somerville
Somerville, Massachusetts
Somerville is a city in Middlesex County, Massachusetts, United States, located just north of Boston. As of the 2010 census, the city had a total population of 75,754 and was the most densely populated municipality in New England. It is also the 17th most densely populated incorporated place in...

, 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
Labor Day
Labor Day is a United States federal holiday observed on the first Monday in September that celebrates the economic and social contributions of workers.-History:...

 weekend 1961. While at a party, Georgie McLaughlin made an advance on the girlfriend of Winter Hill Gang member Alex Rocco
Alex Rocco
Alex Rocco is an American actor. His roles have ranged from comedy to playing gangsters in Mafia movies.-Early life:...

. 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
Charlestown, Massachusetts
Charlestown is a neighborhood of Boston, Massachusetts, United States, and is located on a peninsula north of downtown Boston. Charlestown was originally a separate town and the first capital of the Massachusetts Bay Colony; it became a city in 1847 and was annexed by Boston on January 5, 1874...

 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
Irish Mob
The Irish Mob is one of the oldest organized crime groups in the United States, in existence since the early 19th century. Originating in Irish American street gangs of the 19th century — depicted in Herbert Asbury's 1928 book The Gangs of New York — the Irish Mob has appeared in most...

 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
Gerard O'Neill
Gerard Kitchen O'Neill was an American physicist and space activist. As a faculty member of Princeton University, he invented a device called the particle storage ring for high-energy physics experiments. Later, he invented a magnetic launcher called the mass driver...

, 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
Angiulo Brothers
The Angiulo Brothers , were the leading Italian-American crime group from Boston's North End, during the 1950s and early 1960s...

. The Angiulo Family of the North End was responsible for most of the Italian mafia operations in Boston
Boston
Boston is the capital of and largest city in Massachusetts, and is one of the oldest cities in the United States. The largest city in New England, Boston is regarded as the unofficial "Capital of New England" for its economic and cultural impact on the entire New England region. The city proper had...

 and points north. They answered to the Patriarca crime family
Patriarca crime family
The Patriarca crime family, also known as the New England crime family and the Providence crime family, is an Italian-American organized crime syndicate based in New England, specifically Providence, Rhode Island and Boston, Massachusetts, and is part of the Italian-American Mafia or "La Cosa Nostra"...

 of Rhode Island
Rhode Island
The state of Rhode Island and Providence Plantations, more commonly referred to as Rhode Island , is a state in the New England region of the United States. It is the smallest U.S. state by area...

 who reported to the heads of the Five Families
Five Families
The Five Families are the five original Italian-American Mafia crime families which have dominated organized crime in America since 1931. The Five Families in New York remain as the powerhouse of the Italian Mafia in the United States.-History:...

 of New York, also known as The Commission
The Commission (mafia)
The Commission is the governing body of the American Mafia. Formed in 1931, the Commission replaced the "Boss of all Bosses" title, with a ruling committee, consisting of the New York Five Families bosses and the boss of the Chicago Outfit...

.

Productivity and overall success

The gang's most prominent members included Howie Winter
Howie Winter
Howard Thomas "Howie" Winter is an American mobster. He was the second leader of the infamous Winter Hill Gang.-Early life:...

 and his bookkeeper Salvatore Sperlinga, brothers John Martorano, Lucio E. Licciardi, 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 (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
Kevin Weeks
Kevin Weeks is a former mobster of Irish-American descent and a longtime friend and confidant to James J. Bulger, the infamous boss of the Winter Hill Gang, a crime family based out of the Winter Hill neighborhood in Somerville, Massachusetts.After his arrest and imprisonment in 1999, he became a...

 was not considered a threat, and neither were John Shea
John Shea (mobster)
John "Red" Shea was an Irish-American mobster from Boston involved in narcotics and an associate of crime kingpin Whitey Bulger and the Winter Hill Gang during the 1980s and '90s...

, Eddie Mac, "Polecat" Moore or John Cherry. Howie Carr
Howie Carr
Howard Louis "Howie" Carr, Jr. is an American journalist, author, and conservative radio talk-show host based in Boston with a listening audience rooted in New England.-Radio:...

 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.

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 diverty 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 stuff to insure that they were seen to be of high value to them.

Historical leadership

Leaders

  • 1960s-1965 - James "Buddy" McLean - Boss, killed 1965.
  • 1965-1978 - Howard "Howie" Winter
    Howie Winter
    Howard Thomas "Howie" Winter is an American mobster. He was the second leader of the infamous Winter Hill Gang.-Early life:...

     - 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
    FBI Ten Most Wanted Fugitives
    The FBI Ten Most Wanted Fugitives list arose from a conversation held in late 1949 between J. Edgar Hoover, Director of the United States Federal Bureau of Investigation, and William Kinsey Hutchinson, International News Service Editor-in-Chief, who were discussing ways to promote capture of the...

     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
    Kevin Weeks
    Kevin Weeks is a former mobster of Irish-American descent and a longtime friend and confidant to James J. Bulger, the infamous boss of the Winter Hill Gang, a crime family based out of the Winter Hill neighborhood in Somerville, Massachusetts.After his arrest and imprisonment in 1999, he became a...

     - 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 - Boss of the Winter Hill Mob, (Headquarters in South Boston)

Members

  • Salvatore Sperlinga ("Sal") - Howie Winter's lieutenant and bookkeeper, killed in 1980.
  • Johnny Martorano
    Johnny Martorano
    John James Vincent Martorano also known as "Vincent Joseph Rancourt," "Richard Aucoin", "Nick," "The Cook" and "The Executioner" and "The Basin Street Butcher" , is a former hitman for the Winter Hill Gang in Boston, Massachusetts who has admitted to 20 gang-related killings.-Early life:Johnny...

     - 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
    Patrick Nee
    Patrick Nee is an Irish-American immigrant, former member of the Mullen Gang, Vietnam vet, and the bestselling author of the memoir A Criminal and an Irishman; The Inside Story of the Boston Mob-IRA Connection.-Early life:Nee was born in Ros Muc, an Irish language speaking village in the...

     - Associate of Bulger's with close ties to the Provisional Irish Republican Army
    Provisional Irish Republican Army
    The Provisional Irish Republican Army is an Irish republican paramilitary organisation whose aim was to remove Northern Ireland from the United Kingdom and bring about a socialist republic within a united Ireland by force of arms and political persuasion...

    , 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
    FBI Ten Most Wanted Fugitives
    The FBI Ten Most Wanted Fugitives list arose from a conversation held in late 1949 between J. Edgar Hoover, Director of the United States Federal Bureau of Investigation, and William Kinsey Hutchinson, International News Service Editor-in-Chief, who were discussing ways to promote capture of the...

     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.
  • Jeffrey Dorr - known associate. Deceased 2006.
  • 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
    Alex Rocco
    Alex Rocco is an American actor. His roles have ranged from comedy to playing gangsters in Mafia movies.-Early life:...

    , acting in the film The Godfather
    The Godfather
    The Godfather is a 1972 American epic crime film directed by Francis Ford Coppola, based on the 1969 novel by Mario Puzo. With a screenplay by Puzo, Coppola and an uncredited Robert Towne, the film stars Marlon Brando, Al Pacino, James Caan, Robert Duvall, Sterling Hayden, John Marley, Richard...

    as well as nearly 200 other movie and television roles from 1965 to present.
  • Russell Nicholson - He 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)left Boston area for Florida.
  • John Shea
    John Shea (mobster)
    John "Red" Shea was an Irish-American mobster from Boston involved in narcotics and an associate of crime kingpin Whitey Bulger and the Winter Hill Gang during the 1980s and '90s...

     ("Red") - known associate and narcotics dealer for the gang.
  • Vincent Teresa
    Vincent Teresa
    Vincent "Fat Vinnie" Teresa was an American mobster in the Boston branch of the Patriarca crime family who was a lieutenant of boss Raymond Patriarca....

     - 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 Provisonal 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.

  • Jerry Perkins ("Poker Face") - became a member in 1973, he has been known to frequent slyfox with his dame. is still alive and living in south Boston.
  • Thomas J. Ballot Jr. - former bodyguard of Buddy McClean and close friend of Thomas F. Birmingham.
  • Louis Litif
    Louis Litif
    Louis R. Litif , also known as Nicholas Noonan and Louis Woodward, was a Lebanese-American bookmaker from South Boston, Massachusetts. After running afoul of neighborhood Irish mob boss James J. Bulger, Litif was murdered in 1982. His body was left in a car trunk in the South End, Boston...

     - was recruited by Bulger for extra muscle in the 1970s and a suspect in the 1978 Blackfriars Massacre
    Blackfriars Massacre
    The 1978 Blackfriars Massacre was an American Mafia massacre that occurred on June 28, 1978 in Downtown Boston in Boston, Massachusetts. The massacre claimed four criminals known to the police and a former Channel 7 Boston television investigative news anchorman and reporter, John A. Kelly. The...

    .
  • Anthony Veranis
    Anthony Veranis
    Anthony Veranis, also known as "Mickey White" and "Tony" was an associate of the Winter Hill Gang and a professional welterweight boxer.- Early life :...

     - local boxer who was murdered by John Martorano in 1966.
  • George W. Holden
    George W. Holden
    George W. Holden was a professional heavyweight boxer, born in Medford, Massachusetts.- Personal life :Holden was described by Howie Carr as a small-time hoodlum and boxer who became involved in organized crime...

     - professional welterweight boxer and small time criminal.
  • Timothy A. Connolly 3rd
    Timothy A. Connolly 3rd
    Timothy A. Connolly 3rd , aka "Timmy Connolly" and "TC" is a former South Boston bar owner and mortgage broker, who wore a wire inside the infamous Winter Hill Gang and helped the federal government indict their two leaders, James "Whitey" Bulger and Stephen "The Rifleman" Flemmi...

     - was a soldier for Bulger until becoming an informant in 1989, owned the Corner Cafe, is half Italian-American and half Irish-American.
  • James M. Murphy
    James M. Murphy
    James M. Murphy was an Irish-American Winter Hill Gang mob associate who in 1970 became the subject of a massive manhunt by the then-Boston Police Department Commissioner Francis Roache. He was a fugitive wanted in the shooting of two people murdered at a Christmas Eve party on December 24, 1968...

     - was on Boston Police Department
    Boston Police Department
    The Boston Police Department , created in 1838, holds the primary responsibility for law enforcement and investigation within the city of Boston, Massachusetts. It is one of the oldest police departments in the United States...

    's "Most Wanted List".
  • Paul Moore ("Polecat") - is currently a soldier.
  • Dennis Horkenbach ("Blumpkin") - known associate.
  • Ronnie Fronduto - former associate.
  • Jimmy Flynn
    Jimmy Flynn
    James P. "Jimmy" Flynn is an American teamster and film actor. He was a reputed member of the famous Winter Hill Gang....

     - was a soldier who later became an actor.
  • Tommy McKinnon - known associate.
  • Edward "Eddie Mac" MacKenzie, Jr- 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."

See also

  • Brotherhood (2006 TV series)
  • The Departed
    The Departed
    The Departed is a 2006 American crime thriller film, fashioned as a remake of the 2002 Hong Kong film Infernal Affairs. The film was directed by Martin Scorsese and written by William Monahan...

  • Irish Mob
    Irish Mob
    The Irish Mob is one of the oldest organized crime groups in the United States, in existence since the early 19th century. Originating in Irish American street gangs of the 19th century — depicted in Herbert Asbury's 1928 book The Gangs of New York — the Irish Mob has appeared in most...

  • James J. Bulger
    James J. Bulger
    James Joseph "Whitey" Bulger, Jr. is a former organized crime figure from Boston, Massachusetts.Local folklore depicted Bulger as a Robin Hood-style social bandit dedicated to protecting the neighborhood and its residents. Bulger allegedly masterminded a protection racket targeting drug kingpins...

  • John Connolly (FBI)
    John Connolly (FBI)
    John J. Connolly, Jr. is a former FBI agent, who was convicted of racketeering and obstruction of justice convictions stemming from his relationship with James J. "Whitey" Bulger, Steve Flemmi, and the Winter Hill Gang...

  • Charlestown Mob
    Charlestown Mob
    The Charlestown Mob was an Irish Mob group in Charlestown, which figured prominently in the history of Boston for much of the 20th century....

  • Mullen Gang
    Mullen Gang
    -Gang members:Paulie McGonagle was a Boston mobster and onetime leader of the Mullen Gang, a South Boston street gang involved in burglary, auto theft, and armed robbery. During the war against Donald Killeen and his brothers, McGonagle successfully led the Mullens in a string of shootings which...


External links

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