Informant and partner with the FBI
The FBI first attempted to recruit Whitey Bulger as an informant in 1971, when he was approached by Dennis Condon, a Special Agent with the Boston office. Condon was unsuccessful. In 1974 Bulger was approached by Stephen Flemmi, a mobster with Mafia ties regarding a partnership between them. Flemmi had been working as an FBI informant since 1965. Although FBI agent John Connolly later claimed to have recruited Bulger on his own, it is likely that Flemmi was the one who got Bulger to become a High Echelon confidential informant.
Flemmi had been providing the FBI with information involving local mafia activities and members, and Bulger saw the advantage in working with the FBI to remove mafia influence, creating more room for his own operations. Bulger repeatedly denied providing any information to the FBI, and much of what was attributed to him by FBI agents including Connolly was actually provided by other informants, but there is no denying that Bulger did provide information when it was advantageous for him to do so. The relationship between Bulger and the FBI was quickly corrupted, by both parties.
Information which Bulger extracted from Connolly, or which Connolly had voluntarily provided, led to the murder of John McIntyre following the Valhalla incident. Other information provided by Connolly led to several potential witnesses against Bulger, or competitors in various operations, to vanish. In 1977, concerns within the Boston office of the FBI over Connolly’s handling of Bulger were set aside when agent John Morris was placed in charge of the Organized Crime office. Morris was soon helping Connolly in protecting both Bulger and Flemmi from FBI investigation.
Connolly continued to add information to Bulger’s file which would allow him to convince his superior’s that Bulger was a reliable High Echelon informant, despite the growing evidence that the information was actually extracted from the files of other informants and simply copied into Bulger’s file. While doing so he provided information to Bulger which tipped the latter to take action allowing him to avoid arrest, or to hide evidence from investigators. To help keep pressure off of Connolly, Bulger showered gifts on Morris, including first class plane tickets for Morris’s girlfriend to visit the agent when he was temporarily assigned for training out of Boston.
In 1982 John Callahan was being sought by the FBI to provide information regarding the murder the previous year of Roger Wheeler, a crime which had been ordered by Bulger. When Connolly learned of the FBI’s interest, he informed Flemmi and Bulger, with a warning that Callahan – who had worked with the Winter Hill gang – would likely incriminate them. Reacting to the warning from the FBI agent, Bulger ordered Callahan killed. Connolly eventually was convicted of second degree murder for his actions which impeded the investigation of one murder and led to another.