Winter Hill Gang

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The Winter Hill Gang is a loose confederation of Boston, Massachusetts area, mostly Irish-American organized crime figures. 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.

The Winter Hill Gang also played a central role in the Boston Irish Mob Wars of the 1960s between Winter Hill leader James "Buddy" McLean and Bernard McLaughlin's Charlestown Mob. The Somerville crew ended up eliminating the Charlestown crew and took over as the top "Irish Gang" not only in Massachusetts but up and down the east coast.

The gang was also tied to the murder of Roger Wheeler in Tulsa, Oklahoma.

[edit] Members of the Winter Hill gang

Boss 1950's-1965, killed 1965.
Boss 1965-78, jailed.
Boss 1978-1999, 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, pled 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.
  • Salvatore "Sal" Sperlinga
Howie Winter Lt. & bookkeeper, killed in 1981.
  • 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.
  • Americo "Rico" Sacramone
Buddy McLean bodyguard, with McLean at the Pepermint Lounge in Somerville when he was killed 1965, killed 1976.
  • Kevin Weeks
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 entiltled 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 driver for Johnny Martorano on the Roger Wheeler hit 1981, died 1997.
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 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.

[edit] External links

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