Opinion ID: 202112
Heading Depth: 2
Heading Rank: 1

Heading: Prehistory

Text: 4 Founded in the 1960s, the Winter Hill Gang operated as a criminal syndicate in Massachusetts and beyond until its operations were disrupted in 1999. Based originally in Somerville, Massachusetts, the Winter Hill Gang prospered through participation in a variety of illegal activities, including loan-sharking, bookmaking, trafficking in arms and narcotics, money laundering, and outright extortion. Over the years, as its members achieved territorial dominance over areas that had been previously controlled by rival syndicates, among them La Cosa Nostra, which operated out of Boston's North End, the Winter Hill Gang broadened its reach to other locales. In particular, the group established a base of criminal operations in South Boston, and eventually conducted business from, among other places, a liquor store in that neighborhood known variously as the South Boston Liquor Mart, Columbia Wine and Spirits, and Stippo's Liquor Mart. This case involves the events that led up to the group's acquisition of that store. 5 Among the Winter Hill Gang's most notorious and powerful members were James J. Bulger, known as Whitey, and Stephen Flemmi, known as the Rifleman. Long before they attained prominence, both of these men became informants for the FBI. Flemmi was impressed into the service of the bureau in 1965, and was instrumental in bringing about its well-heralded success at prosecuting members of La Cosa Nostra, which was the dominant organized crime presence in Boston prior to the ascendance of the Winter Hill Gang. (Indeed, the FBI's successful campaign to fight La Cosa Nostra helped clear away the Winter Hill Gang's competition and contributed to Bulger and Flemmi becoming the renowned and powerful gangsters they became.) Bulger was convinced to become an informant in 1974. He was recruited to help the FBI in its crusade against La Cosa Nostra by his childhood acquaintance John Connolly, who joined the FBI's Boston office as an agent in the Boston Organized Crime unit in the mid-1970s. 6 Over the years, John Connolly developed a close working relationship with Bulger and Flemmi, and took extraordinary steps to secure their continued availability to the FBI as informants against La Cosa Nostra. The details of the relationship between Connolly and Bulger and Flemmi were laid out by Judge Wolf in his opinion in United States v. Salemme, 91 F.Supp.2d 141 (D.Mass.1999), and it is not necessary to this case to rehearse all of the particulars of their interactions. The crucial point is that on a number of occasions, Connolly crossed a critical line by offering sanction to Bulger and Flemmi's activities, and in so doing made the FBI a partner in some of the Winter Hill Gang's criminal enterprises. Through Connolly, the FBI offered Bulger and Flemmi virtual immunity from prosecution for a wide range of racketeering activities. See id. at 208-15. In this case, the plaintiffs' claims against the government are based in part on the free reign that Bulger and Flemmi enjoyed to further the interests of the Winter Hill Gang.