John Connolly (FBI)

John Joseph Connolly Jr. (born August 1, 1940) is an American former Federal Bureau of Investigation (FBI) agent who was convicted of racketeering, obstruction of justice and murder charges stemming from his relationship with Boston mobsters James "Whitey" Bulger, Steve Flemmi and the Winter Hill Gang.

State and federal authorities had been trying to imprison Bulger for years, but he evaded capture until 2011. As the FBI handler for Bulger and Flemmi, Connolly (who was previously neighbors with Bulger's family in the Old Harbor Housing Project) had been protecting them from prosecution by supplying Bulger with 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, Connolly was charged with additional racketeering-related offenses. He was convicted 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 forty years in prison. He was released from federal prison on June 28, 2011, and transferred to the Florida State Prison to serve the remainder of his sentence for his 2008 conviction.

In April 2020, Connolly asked to be allowed to serve the remainder of his sentence on home confinement due to fears of contracting COVID-19, citing a 2018 federal law allowing for compassionate release under "extraordinary" circumstances, such as age, health and other critical factors. A Florida judge initially declined to order his release, but Connolly was later granted a medical release on February 17, 2021.

John Joseph Connolly Jr. is the namesake and son of an Irish immigrant, John Connolly Sr. of Maigh Cuilinn in County Galway, a Gillette employee for fifty years. His mother, Bridget T. Connolly (née Kelly), was a housewife. The Connolly family lived in the Old Harbor Housing Project in Boston, Massachusetts, the first public housing project in New England, until John Jr. was twelve years old. The Bulger family, residing a few doors down, had lived in the project since its New Deal creation in 1938; other residents included future U.S. Representative Joseph Moakley, and Francis "Buddy" Leonard, who would later be allegedly murdered by Bulger in 1975 during his violent takeover of Boston's underworld.

Connolly admired his neighbor William "Billy" Bulger, six years his senior; he did not meet Billy's older brother, James "Whitey" Bulger, until he was eight years old. The nineteen-year-old Whitey, who was already notorious as the leader of the Mercer Street gang, bought the other neighborhood boys ice cream and convinced an awestruck Connolly to accept the treat. Later that same year, Connolly found himself outnumbered in a skirmish over a ball with some older boys. According to Connolly, Bulger came along and chased the bullies away.

In 1952, Connolly's family moved to the City Point neighborhood of South Boston. John Jr. was able to attend Columbus High School, a Catholic high school in the Italian North End neighborhood. His younger brother, James, who also later sought a career in law enforcement, joined the Drug Enforcement Administration's New England Division based in Boston.

Connolly attended Boston College with the encouragement of Billy Bulger, and after graduation took classes at Suffolk University Law School. He later earned a graduate degree in Public Administration from Harvard University's John F. Kennedy School of Government. After completing his studies, Connolly worked as a teacher at South Boston High School and at Dorchester High School.