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 James J. "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.
This scandal was the basis for the book Black Mass and served as the inspiration for the setting of 2006 crime thriller film, The Departed, written by William Monahan and directed by Martin Scorsese.
In 2005, Connolly was indicted on murder and conspiracy to commit murder charges in the 1982 slaying of John B. Callahan. He stood trial in 2008 in Miami. Callahan was murdered by John Martorano who shot Callahan and left his body in the trunk of his Cadillac in a parking lot at Miami International Airport. Prosecutors alleged that Callahan was killed on the orders of Whitey Bulger and Stephen Flemmi after Connolly told them that the FBI was investigating his ties to the Winter Hill Gang in their on going investigation into the death of World Jai Alai owner Roger Wheeler. Wheeler had also been killed by Martorano in Tulsa, Oklahoma in May 1981.
During the trial, Bulger associates Stephen Flemmi, Kevin Weeks and John Martorano testified for the prosecution detailing Connolly's ties to Bulger and Flemmi. Long time Bulger girlfriend Teresa Stanley testified for the defense about her travels with Bulger. Flemmi testified that Connolly warned them that the FBI wanted to question Callahan in the death of Wheeler telling them that Callahan "wouldn't hold up" and would probably implicate them.
Also testifying against Connolly was his former FBI boss, John Morris, who admitted that he accepted $7,000 in bribes from Bulger and Flemmi. He stated he began leaking information to them after Connolly delivered a case of wine and an envelope stuffed with $1000 cash from the pair.
Testifying for Connolly was former U.S. Attorney and current U.S. District Senior Judge Edward F. Harrington who testified that Connolly was a star agent who was credited with using informants to help destroy the New England Mafia.
On November 6, 2008, a jury convicted Connolly of second-degree murder. According to the prosecutors, Connolly faced a possible sentence of 30 years to life in prison. Connolly was due to be sentenced on December 4, 2008 but sentencing was postponed until January while the judge in the case, Circuit Judge Stanford Blake, considered a motion by the defense to dismiss the case. The defense argued that in Florida, the statute of limitations had expired for second-degree murder when Connolly was convicted.
On January 15, 2009, Blake sentenced Connolly to 40 years in prison, saying that Connolly "crossed over to the dark side." The judge agreed with the defense's argument involving the statute of limitations, but noted that their motion was past the deadline for such motions. He accepted prosecutors' argument that Connolly abused his badge and deserved more than the 30-year minimum. The sentence will run consecutively with his 10-year sentence for racketeering, meaning that Connolly will spend the rest of his life in prison.
Callahan was directly involved in the murder of Roger Wheeler