(born August 1, 1940) is a former FBI agent who was convicted of racketeering, obstruction of justice, and murder charges stemming from his relationship with James "Whitey" Bulger, Steve Flemmi, and the Winter Hill Gang.
State and federal officers had been trying to imprison Whitey Bulger for years, but Bulger evaded capture until 2011.
As the FBI handler for Bulger and Flemmi, Connolly (who had grown up in the Old Harbor Housing Project with Bulger) had been protecting them from prosecution by supplying Bulger with information about possible attempts to catch them.
In one instance he tipped Bulger that Edward Brian Halloran was testifying to the FBI about his murder of Louis Litif, which led to murder of Halloran and Michael Donahue.
Connolly was indicted on December 22, 1999, on charges of alerting Bulger and Flemmi to investigations, falsifying FBI reports to cover their crimes, and accepting bribes.In 2000, he was charged with additional racketeering-related offenses.
He was convicted on the racketeering charges in 2002 and sentenced to ten years in federal prison.
In 2008, he was convicted on state charges of second-degree murder in Florida and sentenced to 40 years in prison.
He was suspected of tipping off Bulger that a former business associate, a young James "Gentleman Jim" Mulvey in Spokane and another associate in Miami were being investigated for their ties to the Winter Hill Gang; Bulger ordered them murdered to keep them from talking.
Mulvey survived and left the Boston gang scene.
Connolly was released from federal prison on June 28, 2011, and transferred to Florida State Prison to serve the remainder of his sentence for his 2008 second degree murder conviction.