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 Boston Irish Gang War started in 1961 and lasted until 1966 . 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 .Howie Carr, "The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century"
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 a Winter Hill Gang member. He was subsequently beaten unconscious by members of the Winter Hill Gang, and dumped outside of the local hospital.Howie Carr, "The Brothers Bulger: How They Terrorized and Corrupted Boston for a Quarter Century"
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 McLaughlin twice in the back of the head.
In 1965 McLean was shot and killed. 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 gang in the New England area but along the east coast as well. It was claimed they could hold their own against the local Italian crime family.
- James "Buddy" McLean - ''Boss 1950's-1965, killed 1965.''
- Howard "Howie" Winter - ''Boss from 1965 until 1978 . Jailed, released in 2004 .''
- James "Whitey" Bulger - ''Boss from 1978 to 1997 , perhaps one of the most infamous Irish Mob bosses. Fled Boston in 1994 due to being on the F.B.I. Ten Most Wanted list and has a $1 million reward for his capture.
- Stephen "The Rifleman" Flemmi - ''Second in command to Bulger. When he was arrested 1995, he exposed himself and Bulger as FBI informents 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.''
- Salvatore "Sal" Sperlinga - ''Howie Winter Lt. 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 due out 2007.''
- James "Jimmy" 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 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 in 1976.
- Kevin Weeks - ''Bulger Lt. 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 "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 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.
- Alexander "Bobo" Petricone , aka Alex Rocco - ''It was Petricone's girlfriend on class="copylinks">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.''
- Michael Roark - ''Soldier for the John Martorano crew.''
- James "Jimmy" Simms
- George Kaufman - ''Small time hustler and mechanic, owned the garage where the gang frequently met. Died in 1996 of natural causes.''
- Charles Hughes - "Enforcer of the Winter Hill Gang in Sommerville, and good friend of Jimmy. he was feared throught the Boston area."
- Rob Hill - ''Soldier, bookmaker, and drug dealer for the Winter Hill Gang.''
- Tommy Ballou
- William "Billy" Emma
- John Mary "Fingers" McGrath
- Anthony Ciulla - ''Horse race-fixer for the Winter Hill Gang.''
- John Shea (mobster) - '' 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 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.
- Jim "Jimmy Two Times" Distler ; An "Associate" linked to The Chicago Outfit as well as affiliations with Florida and Midwestern mafia syndicates. In 2003 he received probation for Money Laundering . It is rumored to be operating several businesses for the Chicago Outfit as well as The Mountain Boys crime syndicate. Cannot be a "made man" due to his German-Irish background, "Jimmy Two Times" is considered to be a solid money maker for both organizations.
- David Crowley - ''An associate of Bulger.''
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.
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