John Connolly (FBI)

The Bulger family, residing a few doors down, had lived there since its New Deal creation in 1938; other residents were future US Representative Joseph Moakley, and Francis "Buddy" Leonard, who would later be allegedly murdered by Bulger in 1975 during his battle for power over the rackets.

Connolly admired his neighbor William Bulger, six years his senior; he did not meet his older brother, Jimmy, nicknamed "Whitey" because of his white-blond hair, until Connolly was eight years old.

The 19-year-old Whitey, who was already notorious as the leader of the Mercer Street gang, bought the other neighborhood boys ice cream cones 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.

John Joseph Connolly Jr. (born August 1, 1940) is an American 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.

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 later sought a career in law enforcement, joined the DEA New England Division based in Boston.

Connolly was encouraged to attend Boston College by 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.

After seeking advice from Billy Bulger, now a State Representative, about career opportunities in law enforcement, in 1968, he met with H. Paul Rico's FBI partner, Special Agent Dennis Condon, and Boston Police Department Detective Edward Walsh, an old friend of the Connolly family's. Both Condon and Walsh would later brag that they had "recruited" Connolly.

On August 1, 1968, U.S. House Speaker John W. McCormack wrote a personal note to J. Edgar Hoover on behalf of a constituent.

The letter began, "Dear Edgar, It has come to my attention that the son of a lifelong personal friend has applied to become a special agent of the Federal Bureau of Investigation ..."[17] Connolly was appointed to the FBI in October 1968.

FBI Supervisor John M. Morris, who would also later face charges of corruption, was Connolly's supervisor during much of Connolly's time working for the FBI.

Connolly began his FBI career in the Baltimore and San Francisco field offices before being transferred to New York City.

He wanted to return to Boston to be closer to his ailing father.

Ironically, Dennis Condon, who was Connolly's FBI supervisor, had approached Whitey Bulger in the early 1970's, with little result.

Because of their neighborhood ties, Connolly would prove to have the inside track with Bulger that Condon did not.

A year after he arrested Mafioso Frank Salemme, the FBI transferred Connolly to its Boston field office in the John F. Kennedy Federal Building in 1973.

Through his second marriage, he was the brother-in-law of Arthur Gianelli, a racketeer who was later indicted with Joe "Joey Y" Yerardi, who oversaw Johnny Martorano's criminal operations when Martorano was a federal fugitive in Florida between 1978 and 1995.

In 1980, he moved to 48 Thomas Park in the Dorchester Heights neighborhood, across the street from South Boston High School.

During his career in the FBI, Connolly investigated organized crime.

He was one of the primary agents involved in developing the Top Echelon Criminal Informants Program in New England.

Over the span of his career he received eight commendations from every Director of the Federal Bureau of Investigation, from J. Edgar Hoover through L. Patrick Gray, William Ruckelshaus, Clarence M. Kelley, James B. Adams, William H. Webster, John Otto, and William S. Sessions.

In 1989, the DEA was probing the Winter Hill Gang for suspected drug trafficking.

The DEA was aware that a former roommate and John's brother James both worked for the DEA.

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, Connolly was convicted on state charges of second-degree murder in Florida and sentenced to 40 years in prison.

State and federal officers 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 neighbors with the Bulgers in the Old Harbor Housing Project) had been protecting them from prosecution by supplying Bulger with information about possible attempts to catch them.

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 Miami-Dade 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 50 years.

Connolly's mother, Bridget T. Connolly (née Kelly), was a housewife.

They lived in the Old Harbor Housing Project in Boston, the first public housing project in New England, on O'Callaghan Way until John Jr. was 12 years old.