John Joseph Connolly Jr. (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 feeding Bulger 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.[citation needed]

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 business associate in Miami was being investigated for his ties to the Winter Hill Gang; Bulger ordered him murdered to keep him from talking

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.