The Winter Hill Gang was a loose confederation of American organized crime figures in the Boston, Massachusetts area.
Winter Hill Gang members are alleged to have been involved with most typical organized-crime-related activities, but they are perhaps best known for fixing horse races in the northeastern United States and shipping weapons to the Provisional Irish Republican Army (IRA).
While at a party, Georgie McLaughlin made an advance on the girlfriend of Winter Hill Gang member Alexander Petricone, Jr. (who fled the Boston area during the war and became an actor under the name Alex Rocco).
[8] McLaughlin was subsequently beaten unconscious by members of the Winter Hill Gang and was dumped outside the local hospital.
One of the surviving McLaughlin brothers, nicknamed "Punchy", was shot while waiting for a bus in the West Roxbury section of Boston.
A year later, in 1966, the last two associates of the McLaughlin Gang, brothers Connie and Steve Hughes were killed, allegedly by hitman Frank Salemme.
In the book Black Mass by Dick Lehr and Gerard O'Neill, the authors make the unsubstantiated claim that the Winter Hill Gang was far more feared and powerful than their rivals, the Boston branch of the Patriarca crime family run by the Angiulo Brothers.
They learned the lesson of their gang's disastrous foray into gambling after wiping out Joseph (Indian Joe) Notarangeli's crew.
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.
[7] The Winter Hill Gang played a role in the Irish Republican Army's paramilitary actions in the late 20th century.
The Winter Hill Gang also had a plot spoiled by a local fisherman John McIntyre who they had partnered with but who went to the police after hearing word of a gun-running mission.
[11] In 1998, during a trial for racketeering and fixing horse races, Steve Flemmi and Whitey Bulger were revealed under disclosure to be FBI informants.