Winter Hill Gang

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The Winter Hill Gang is a loose confederation of Boston-area organized crime figures, mostly Irish-American and some Italian-American. It derives its name from the Winter Hill neighborhood of Somerville, Massachusetts north of Boston. Its members have included notorious Boston gangster James J. "Whitey" Bulger and hitman Stephen J. "The Rifleman" Flemmi.

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 Bulger's predecessor Howie Winter, were indicted by federal prosecutors in 1979.

[edit] Irish Gang War

The Boston Irish Gang War started in 1961 and ended in 1966. It was fought between the McLaughlin Gang of Charlestown, headed by Bernie McLaughlin and the Winter Hill Gang of Somerville, headed by James "Buddy" McLean.[1]

The two gangs had co-existed together in relative peace for a number of years until an incident on Labor Day weekend 1961. While at a party Georgie McLaughlin made advances to the girlfriend of a Winter Hill Gang member. He was subsequently beaten unconscious by members of the Winter Hill Gang and dumped outside of the local hospital.[1]

Bernie McLaughlin then went to see James McLean and demanded that he hand over the members of the gang who beat his brother. McLean refused. The McLaughlins' taking this refusal as an insult then made a failed attempt to wire a bomb to McLean's wife's car. In retaliation McLean shot McLaughlin twice in the back of the head.[1]

In 1965 Mclean was shot and killed. Howie Winter then took over the Winter Hill Gang.

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 then reputed to be the top Irish Mob gang in the New England area. It was even said that they could hold their own against the local mafia.[1]

[edit] Members of the Winter Hill gang

Boss 1950's-1965, killed 1965.
Boss 1965-78, jailed, released in 2004.
Boss 1978-1997, fled 1994, exposed as F.B.I. informer 1997, he is on the "F.B.I. Ten Most Wanted" list and has a $1 million reward for his capture.
Second in command to "Whitey" Bulger, arrested 1995, exposed himself and Bulger as F.B.I. informers in the Spring of 1997, plead out to ten murders in February 2004 in exchange for a life sentence with no chance of parole.
  • Vincent "Jimmy The Bear" Flemmi
Brother of Steve, feared enforcer and hitman, died of drug overdose in 1979.
Howie Winter Lt. & bookkeeper, killed in 1980.
  • John Martorano
Top hitman for Bulger & Flemmi, indicted & arrested 1995, flipped 1999, sentenced to 14 years 2004, with time served due out 2007.
  • James "Jimmy" Martorano
Brother of John, now a Capo in the Boston Faction of the New England Patriarca crime family.
Associate of "Whitey" Bulger's with close ties to the Irish Republican Army, arrested in 1990 by the FBI, released after 8 years. Now works in South Boston.
  • Americo "Rico" Sacramone
Buddy McLean bodyguard, with McLean at the Pepermint Lounge in Somerville when he was killed 1965, killed 1976.
Bulger Lt. and Operational Chief of Gang 1994-99, 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 "Tony Blue" D'Agostino
Buddy McLean bodyguard, with Mclean at Pepermint Lounge in Somerville when he was killed 1965.
  • Thomas "Tommy" Ballou, Jr.
Buddy McLean driver & bodyguard, killed 1970.
An original member of the gang. McDonald was a small-time hitman, World War II vet and feared street fighter. At one point held a spot on the FBI's top 10 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.
It was Petricone's girlfriend on Labor Day weekend of 1961 that Georgie McLaughlin hit on. This started the war between The Winter Hill and McLaughlin Gangs. Bobo later lost weight and became actor Alex Rocco, who appeared in the film The Godfather.
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.
Horse race-fixer for the Winter Hill Gang
  • John Shea (mobster): He was an amateur boxer who found the street life 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 tender 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 copped a twelve year plea deal. He was released in August of 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.

[edit] External links

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