Criminal activities
During the 1970s, the gang's most prominent members were Howie Winter, John Martorano, James J. Bulger, Stephen Flemmi, Joseph McDonald and James Sims. The Winter Hill Gang was quite proficient at murdering rival mobsters in order 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) Notarangeli'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 Stephen Flemmi lost interest in running any kind of gambling operation. They would eventually only provide protection for bookmakers, drug dealers and truck hijackers. By 1975, Howie Winter and John Martorano were going broke. Eventually they had to go to Patriarca family underboss Gennaro Angiulo 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 included rigging horse races and drug trafficking. [5]
It was the decision to involve outsiders with their business that led to their downfall. By 1979, Howie Winter and the rest of the Somerville crew were all sent to prison for fixing horse races, leaving Whitey Bulger and Stephen Flemmi as the new leaders of the Winter Hill Gang. During the 1980s, Bulger's associates consisted of Kevin Weeks, Kevin O'Neil, and Patrick Nee. By 1991, even as James J. Bulger's criminal career was winding down, he remained the undisputed mob boss. His criminal associate Kevin Weeks was not considered a threat, and neither were Jim Mulvey, even though he suspected Bulger of being an FBI informant, Billy Shea, John Shea, Tim Connolly, Pat Linskey, Eddie MacKenzie, Paul "Polecat" Moore or John Cherry. Boston journalist Howie Carr commented, "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. Despite the above unsubstantiated claims of the gang's apparent inability to successfully run organized crime rackets, Bulger generated well over $25 million in racketeering proceeds alone throughout his criminal career, according to paperwork filed in federal court. [5]
The Winter Hill Gang played a role in the Irish Republican Army's paramilitary actions in the late 20th century. In his novel, A Criminal and an Irishman, Patrick Nee detailed the gang's involvement with the IRA. He said that Bulger "loved being associated with the IRA and the cause of Irish Freedom". [9] He went on to say that Bulger's association with the IRA gave him a sense of legitimacy. Nee played an active role in raising funds and smuggling weapons to the IRA. In September of 1984, the Valhalla, a fishing boat, left Boston harbor loaded with weapons. [9] The vessel was seized by two Irish Naval Service ships upon arriving in Ireland having been sold out by an Irish informant. 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. [10] The authorities attempted to use McIntyre as an informant against Whitey Bulger. However, Whitey Bulger received information from FBI agent John Connolly that the fisherman had gone to the police. Connolly provided McIntyre's whereabouts and Whitey Bulger along with his right-hand man Stephen Flemmi tortured and killed him. [10]
