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The Winter Hill Gang is a loose confederation of Boston, Massachusetts-area organized crime figures, predominantly Irish-American with a small Italian-American faction. It derives 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^{citation needed}. 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 north-eastern 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 2003. 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.¹

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 Rocco² He was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside of the local hospital.¹ 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. This was the start of Boston's Irish Gang War.¹

In 1965 McLean was shot and killed by one of the last survivors of the McLaughlin Gang, Stevie 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 Family. 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 who, like all mafia in the United States, reported to the branches of the Five Families of New York, New Jersey and Connecticut, The Tri-State Mafia. When the five families, then headed by Paul Castellano, became disillusioned with the Boston activities, production, and effect on the bottom line in the mid 1970s, they cut a deal with the FBI to use Bulger's gang as the vector to infiltrate the Boston Family.

Productivity and overall success

The gang's most prominent members included Howie Winter and his bookkeeper Salvatore Sperlinga, brothers John Martorano and James Martorano, Lucio E. Licciardi, Jerald G. Digiovanni, 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 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. Meanwhile. 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 including rigging horse races and drug trafficking. It was this decision to involve outsiders with their business that led to their downfall on many occasions. By 1991 as James J. Bulger's criminal career was winding down, he remained the indisputed mob boss. His criminal associates Kevin Weeks was not considered a threat, and neither was 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.

Members of the Winter Hill gang

• James "Buddy" McLean - Boss 1950s-1966, killed 1966.
• Howard "Howie" Winter - Boss from 1965 until 1978. Jailed, released in 2002.
• James "Whitey" Bulger - Boss from 1978 to 1997, one of the most infamous Irish Mob bosses. Fled Boston in 1994 due a pending federal indictment. He is now on the FBI's Ten Most Wanted list, listed fourth after Osama Bin Laden and has a $2 million bounty on his head.
• Stephen Flemmi - turned state's evidence when Whitey fled in 1997.
• Vincent Flemmi ("Jimmy The Bear") - Brother of Steve, feared enforcer and hitman, died of drug overdose in 1979.
• Salvatore Sperlinga ("Sal") - Howie Winter lieutenant and bookkeeper, killed in 1980.
• John 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.
• Edward “Teddy” Deegan - Bank robber and associate of Stevie Flemmi.
• James Martorano - Brother of John, now a Capo in the Boston Faction of the New England Patriarca crime family.
• Patrick Nee - Associate of Bulger's with close ties to the Provisional Irish Republican Army, arrested in 1990 by the FBI, released after 8 years. Now works in South Boston.
• Americo Sacramone ("Rico") - Buddy McLean bodyguard, with McLean at the Peppermint Lounge in Somerville when he was killed 1965. Killed in 1976.
• Kevin Weeks - Bulger lieutenant and operational chief of Gang 1994 through 1999. He was arrested and jailed November 15, 1999 and later defected in January 2000. Released from 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.
• Anthony D'Agostino ("Tony Blue") - Buddy McLean bodyguard, with Mclean at Pepermint Lounge in Somerville when he was killed 1965.
• Thomas Ballou, Jr. ("Tommy") - Buddy McLean driver and bodyguard. He was killed in 1970.
• Joseph "Joe Mac" McDonald - An original member of the gang. McDonald was a hitman, World War II veteran and street fighter. At one point held a spot on the 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.
• Alex Rocco ("Bobo") - It was Petricone's girlfriend on Labor Day weekend of 1961 that McLaughlin hit on. This started the war between The Winter Hill and McLaughlin Gangs. Petricone later lost weight and became actor Alex Rocco, who appeared in the film The Godfather.
• 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 McLaughlin Gang in 1964.
• James "Jimmy" Simms - Released from prison in 1986 - Whereabouts unknown
• George Kaufman - Small time hustler and mechanic, owned the garage where the gang frequently met. Died in 1996 of natural causes.
• William Emma ("Billy")
• John Shea - A former amateur boxer who found crime much more appealing. He wound up working in the Winter Hill Gang's drug operation and rose to the rank of Lieutenant within the gang at the young age of 20. At the age of 24 he was indicted under the RICO Act for running an on going criminal enterprise distributing and trafficking in narcotics, at the age of 27 he accepted a twelve year plea deal. He was released in August 2005 at the age of 40 and wrote his life story in the book "Rat Bastards". He has retired from the South Boston Irish Mob.
• Richard Castucci, bar owner and FBI informant
• Vincent Teresa, New England con man and mob associate who testified 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 the La Cosa Nostra.
• Samuel Lindenbaum, independent hoodlum who was a charter Charlestown Mob member that was murdered alongside Steven Hughes
• Francis Benjamin
• John Murray
• Joseph Francione
• Edward Deegan, relative of Bonanno crime family capos Alphonse Indelicato and Anthony Indelicato from New York
• Leo R. Lowry
• Thomas J. Ballou Jr., former bodyguard of Buddy McClean and close friend of Thomas F. Birmingham
• Louis Litif was recruited by Bulger for extra muscle in the 1970s and a suspect in the 1978 Blackfriars Massacre
• Nicholas Femia, a wealthy South Boston bookmaker and cocaine dealer, shot dead while trying to rob a gas station
• Anthony Ciulla was a bookmaker who organized crooked horse races
• George Holden, local hoodlum and amatuer boxer
• Anthony Veranis, local hoodlum and boxer who was murdered by John Martorano
• Roger Lanier, bankrobber who was shot dead in the line of duty BPD patrolman and later Massachusetts State Senate lobbyist William Delaney
• Patrick Linskey, close friend of James J. Bulger and lottery jackpot winner; he is still collecting $89,000 a year after withholdings until 2011.
• William Barnoski is a Winter Hill Gang associate who was convicted with Anthony Cuilla for fixing horse races
• Joseph Lundbaum, Boston Police Department Detective and uncle of Julia Lundbaum, the wife of Stippo Rakes whose South Boston Liqour would later be taken over as the headquarters of the Winter Hill Gang
• George W. Holden, professional welterweight boxer and small time criminal
• Richard J. Schneiderham, Boston Police Department Massachusetts State Police Lieutenant who was a childhood friend of Stephen Flemmi who later accepted bribes from Flemmi and The Winter Hill Gang

Currently the Massachusetts State Police suspect there are about fifty active members of the gang, along with many other associates who have not been made.

References

External links

• The Search for 'Whitey' Bulger - The Boston Globe
• Winter Hill Gang Leader Flemmi Pleads Guilty - Department of Justice Press Release
• Whitey World A to Z
• American Organized Crime - Irish Mob - The Winter Hill Gang

Wikipedia content modification information:

• This page was last modified on 13 November 2008, at 18:48.

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