Opinion ID: 201862
Heading Depth: 2
Heading Rank: 1

Heading: The Winter Hill Gang and the FBI

Text: 6 The Winter Hill Gang was the name for the dominant organized crime syndicate in the Boston area in the 1970s and 1980s. The Gang's activities included murder, bribery, extortion, loan sharking, and illegal gambling. James Whitey Bulger (Bulger) and Stephen The Rifleman Flemmi (Flemmi) were two prominent members of the Gang. 7 In 1967, FBI Agent H. Paul Rico (Rico) recruited Flemmi as an FBI informant. In 1976, Agent John Connolly (Connolly) recruited Bulger as an informant. Connolly and Bulger were childhood neighbors in South Boston. Eventually, both Bulger and Flemmi were promoted to the status of Top Echelon informant. The Winter Hill Gang's main rival in crime was the Boston branch of La Cosa Nostra, another organized crime syndicate. The FBI wanted to bring down La Cosa Nostra and Bulger and Flemmi were very pleased to help it do so. 8 This convenient relationship eventually took a turn for the worse. While they were informants, Bulger and Flemmi were responsible for multiple murders, including those of Roger Wheeler, Brian Halloran, and Callahan, to be discussed below. The FBI, intent on keeping its informants happy, turned a blind eye to their crimes and failed to follow FBI guidelines for dealing with informants. For example, FBI agents interfered with the investigation of Bulger and Flemmi for the murder of Callahan by preventing Oklahoma FBI agents from interviewing them. The FBI also informed Bulger and Flemmi of a bugged location to prevent them from incriminating themselves. At the same time, Bulger and Flemmi ingratiated themselves to the FBI by assisting the agents. For example, when FBI Agent John Morris (Morris), Agent Connolly's supervisor, was in Georgia for training and he wanted his secretary to fly to meet him for a romantic tryst, Bulger and Flemmi paid for her plane ticket. This cozy relationship created a protective shield around Bulger and Flemmi that emboldened them in their criminal activities — so much so that at one point Flemmi stated that the FBI gave Bulger and him free reign to commit any crime short of murder. 9 Eventually, this cozy relationship between the FBI and Bulger and Flemmi broke down when more reputable law enforcement agents charged Bulger and Flemmi with numerous crimes. Agent Connolly tipped off Bulger, who, to this day, is in hiding from law enforcement authorities. Agent Morris was granted immunity for his testimony, and he testified against Flemmi.