John J. "Zip" Connolly Jr. is a former FBI agent, currently incarcerated in a federal penitentiary for racketeering and obstruction of justice convictions stemming from his relationship with Whitey Bulger, Steve Flemmi, and the Winter Hill Gang. He is the brother-in-law of Arthur Gianelli who is married to Mary Ann Moore, the sister of Connolly's wife Elizabeth.
State police and other federal officers had been trying to imprison Whitey Bulger for years, but somehow Bulger always avoided getting caught. 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 feeding him information about possible attempts to catch them.
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 10 years in prison.