Stephen Flemmi - Relationship With James J. Bulger

Relationship With James J. Bulger

In 1967, James J. "Whitey" Bulger was released from Federal prison after serving a nine-year sentence for robbing banks. After a few years of working as a janitor, he became an enforcer for South Boston mob boss Donald Killeen. After Killeen was murdered by an enforcer for the Mullen Gang, Winter Hill Gang boss Howie Winter mediated the dispute between Bulger and the remaining Killeens and the Mullens, who were led by Patrick Nee. Winter soon chose Bulger as his man in South Boston. Shortly afterward, Bulger became partners with Flemmi.

At this time, the Boston FBI office tried to convince Bulger to become an informant, but he refused.

Disgraced former FBI agent John Connolly (FBI), who grew up with Bulger in South Boston, always claimed that he reached an agreement with Bulger during a late night meeting inside an unmarked car. According to Flemmi, Bulger became an informant on his own and quickly learned of his partner's secret.

Bulger allegedly told Flemmi that he knew his secret. Flemmi has insisted that he did not know at the time that Bulger was also an informant. Weeks, however, insists that Flemmi's story is untrue. He considers it too much of a coincidence that Bulger became an informant a year after becoming Flemmi's partner. He has written of his belief that Flemmi had probably helped to build a Federal case against him. Weeks has said that Bulger was likely forced to choose between supplying information to the FBI or returning to prison.

However, Flemmi and Bulger were quickly able to turn their informant status to their own advantage. John Connolly, who had been assigned to keep an eye on them, soon came to look up to Bulger and viewed him like an older brother. Federal prosecutors have since stated that Connolly became a member of the Winter Hill Gang, allegedly supplying them with the names of informants and funneling bribes to at least one fellow agent.

In 1979, the U.S. Attorney indicted the leadership of the Winter Hill Gang, including boss Howie Winter, on extortion, gambling, and racketeering charges. Flemmi and Bulger were both listed as unindicted co-defendants. John Connolly had convinced prosecutors that his two informants were too valuable to prosecute. At that time, Irish-American gangsters were not the FBI's main concern; they wanted to destroy the Patriarca crime family. Then, as now, arrests and trials of Italian-American mobsters garnered far more of the publicity on which the FBI's funding depends. After the conviction of Winter and his associates, the leadership of the Winter Hill Gang devolved on Bulger, who chose Flemmi as his lieutenant. The pair moved the gang's headquarters to the Lancaster Street Garage in Boston's West End.