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. 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.[3]
In 2000, Connolly was charged with additional racketeering-related offenses. He was convicted in 2002 and sentenced to ten years in federal prison.[4] In 2008, Connolly was convicted on state charges of second-degree murder in Florida and sentenced to 40 years in prison. He was released from federal prison on June 28, 2011,[5] and transferred to the Florida State Prison to serve the remainder of his sentence for his 2008 conviction.[6]
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.[7] A Miami-Dade judge initially declined to order his release,[8] but Connolly was later granted a medical release on February 17, 2021.[9]
Early life
John Joseph Connolly Jr. is the namesake and son of an Irish immigrant, John Connolly Sr. of Maigh Cuilinn in County Galway,[10] 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. 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,[11] and Francis "Buddy" Leonard, who would later be allegedly murdered by Bulger in 1975 during his battle for power over the rackets.[12]
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.[13]
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.[14]
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,[17] 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. 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.[13]
FBI career
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.[1] He wanted to return to Boston to be closer to his ailing father.[18] 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.[1][19][20]
In 1989, the DEA was probing the Winter Hill Gang for suspected drug trafficking.[23] The DEA was aware that a former roommate and John's brother James both worked for the DEA. As an FBI supervisor later noted in a memo, the head of the DEA's Boston office "quietly changed the duties of both these DEA special agents so they would not become aware of this matter."[14]
Boston FBI Special Agent Robert Fitzpatrick said:
Connolly just became a force unto himself, a vortex in a constantly changing system. He stayed put as new agents in charge came and went. And he could take care of other agents. He became the guy who could get you sports tickets. He could help you get a day off through the secretaries. He made no secret that he could help you get a job after retirement through Billy Bulger. But he wasn't that much of an agent. He couldn't write a report. He was no administrator. He was just this brassy bullshit artist. We enabled him to some extent. No one had the stomach for examining what he was up to. We just never came to grips with that guy.[24]
Connolly's dapper, even flashy, appearance meant he stood out as an FBI agent. Bulger poked fun at his foppishness; referring to Connolly as "Elvis" because of his perfectly combed hair.[25]
Before he was brought up on criminal charges, Connolly was mentioned in Gerard O'Neill and Dick Lehr's crime fiction book, The Underboss: The Rise & Fall of a Mafia Family (1989), which followed the FBI's campaign against Gennaro Angiulo with Connolly, John Morris, and a team of fellow FBI agents.[26]
Personal life
Connolly's first wife, Marianne Lockary, was his childhood sweetheart whom he married as he neared graduation from Suffolk University Law School. In January 1982, he and Lockary, who cited an "irretrievable breakdown" of their marriage after a four-year separation, divorced. In 1988, Connolly married Elizabeth L. Moore, a court stenographer who worked at the FBI headquarters at Government Center, Boston.[1]
Connolly had no children with his first wife but fathered three sons with his second wife, Elizabeth. His sister-in-law Mary Ann Moore is married to Arthur Gianelli. Gianelli and Connolly purchased adjoining properties in Lynnfield, Massachusetts, from Rocco Botta, a reputed Mafia extortionist. Their adjacent homes were built by Thomas F. Tuffo, the real estate partner of Kevin P. O'Neil, who the FBI claimed was a long-time money launderer and enforcer for Bulger and Flemmi.[27]
Meeting Flemmi and Bulger
Connolly first met with FBI informants Stephen Flemmi and Whitey Bulger at a coffee shop in Newton, Massachusetts. Louis Litif, one of the top bookmakers and a Winter Hill Gang mob associate, was one of Connolly's handball partners at the Boston Athletic Club. Bulger nicknamed Connolly "Zip" because the lawman shared the same South Boston ZIP Code as the Bulger clan.[28]
He occasionally lectured FBI agents at the FBI Academy in Quantico, Virginia on informant development tactics and techniques and was a member of the Boston FBI's Organized Crime Squad. Retired FBI Special Agent Joseph D. Pistone wrote in the book, The Ceremony, "The reign of the Patriarca Family is virtually ended. A substantial amount of the credit for the demise of that mob Family must be given to one man, Special Agent John Connolly."[29] Connolly retired from the FBI honorably in 1990 and accepted the position of Director of Security/Public affairs for Boston Edison, from former Boston FBI Special Agent John Kehoe.
In 2005, Connolly was indicted on murder and conspiracy to commit murder charges in the 1982 slaying of John B. Callahan and the 1981 murder of Roger Wheeler, owner of the World Jai Alai sporting corporation. Connolly stood trial in 2008 in Miami, Florida.[30] Callahan was murdered by John Martorano, who left the corpse in the trunk of a Cadillac in a Miami International Airport parking lot.[31]
Prosecutors alleged that Callahan was killed on the orders of Whitey Bulger and Stephen Flemmi, after Connolly told them that the FBI was investigating Callahan's ties to the Winter Hill Gang in their ongoing investigation into Wheeler's death. Martorano had killed Wheeler in Tulsa, Oklahoma, in May 1981.[32]
During the trial, Bulger associates Flemmi, Martorano, and Kevin Weeks testified for the prosecution detailing Connolly's ties to Bulger and Flemmi. Flemmi testified that he and Bulger paid Connolly $235,000 over the years, but started cutting his payments in the late 1980s after he started attracting attention through too many luxury purchases, including a boat. IRS special agent Sandra Lemansky testified that during the 1980s Connolly bought a 27-foot Sea Ray for $46,567; a South Boston condo for $63,000, with a $12,000 down payment; a Brewster condo for $80,000, with a $15,000 down payment; land in Chatham for $98,000; and then built a house on the Chatham property for $132,000. During the 1980s, Connolly's annual FBI salary started at $45,000 and gradually increased to $65,000, she said. Denise Taiste, an FBI employee who worked as an assistant to Connolly in 1988 testified that on one occasion when he was not in the office, Connolly instructed her to leave his paycheck in his desk. Taiste admitted that she looked at the check, which was for $2,078.61, then opened the middle drawer of his desk and saw about 10 more uncashed checks inside.[33]
Bulger's former girlfriend, Theresa 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, and that Callahan "wouldn't hold up" and would probably implicate them.[34] Also testifying against Connolly was his former FBI superior, John Morris, who admitted that he had accepted $7,000 in bribes from Bulger and Flemmi. Morris stated that he began leaking information to them after Connolly delivered a case of wine and an envelope stuffed with $1,000 cash from the pair.[35]
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.[37] Sentencing was postponed until January 2009, while Circuit Judge Stanford Blake considered a motion by the defense to dismiss the case. The defense argued that in Florida, when Connolly was convicted, the statute of limitations had expired for second-degree murder.[38]
On January 15, 2009, Judge 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.[39] The judge accepted the prosecutors' argument that Connolly abused his badge and deserved more than the 30-year minimum. The 40-year state sentence runs consecutively with the 10-year federal sentence.[40]
Connolly served his time in FCI Butner Low facility at the Federal Correctional Complex, Butner, North Carolina. He was released from federal custody on June 28, 2011,[5] and was transferred to a Florida state prison to serve his 40-year state sentence. Connolly has stated that he had nothing to do with the Callahan murder. With Bulger's capture on June 24, 2011, Connolly's attorney said his client would appeal if Bulger corroborated Connolly's claim of innocence.[41]
On May 28, 2014, Connolly's murder conviction was overturned by a panel of Florida'sThird District Court of Appeal by a vote of 2–1. The panel held that since Connolly did not "carry or discharge the gun that was used to kill John Callahan in South Florida", it was not appropriate to convict him of murder.[42] On July 29, 2015, the full court en banc reinstated Connolly's murder conviction by a vote of 6–4, finding that the conviction was legally proper, even though he was on Cape Cod when Martorano killed Callahan. Judge Leslie B. Rothenberg, who had been the lone vote for conviction in the earlier hearing, wrote, "It now no longer matters whether the defendant hired (procured) a hit man, turned to his mob friends to murder Callahan, served as a lookout, provided the gun, or pulled the trigger himself, he is a principal in the first degree." Under Florida sentencing guidelines, Connolly was required to serve at least one-third of his sentence before becoming eligible for parole.[43]
Connolly was paroled from prison in Florida in 2021 without objection from Callahan's widow after prison officials learned he was gravely ill and possibly had only another year to live. He returned to Massachusetts, but will remain under supervision until 2047.[44] Despite his convictions, Connolly retained and continues to receive pension benefits from his service as a Federal agent.[44]
James Joseph "Whitey" Bulger Jr. was an American organized crime boss who led the Winter Hill Gang in the Winter Hill neighborhood of Somerville, Massachusetts, a city directly northwest of Boston. On December 23, 1994, Bulger fled the Boston area and went into hiding after his former FBI handler, John Connolly, tipped him off about a pending RICO indictment against him. Bulger remained at large for sixteen years. After his 2011 arrest, federal prosecutors tried Bulger for nineteen murders based on grand jury testimony from Kevin Weeks and other former criminal associates.
The Winter Hill Gang was a loose confederation of organized crime figures in the Boston, Massachusetts, area. It is generally considered an Irish Mob organization, with most gang members and the leadership consisting predominantly of Irish-Americans, though some notable members, such as Johnny Martorano, are of Italian-American descent.
Stephen Joseph Flemmi is an American gangster and convicted murderer and was a close associate of Winter Hill Gang boss Whitey Bulger. Beginning in 1975, Flemmi was a top echelon informant for the Federal Bureau of Investigation (FBI).
Harold Paul Rico was an FBI agent, indicted for murder in 2003. He was accused of the 1968 framing of four men for murder but died before his trial would have taken place.
Francis Patrick Salemme, sometimes spelled Salemmi, also known as "Cadillac Frank" and "Julian Daniel Selig", was an American mobster from Boston, Massachusetts who became a hitman and eventually the boss of the Patriarca crime family of New England before turning government witness.
The Angiulo brothers, were the leading Italian-American crime group from Boston's North End, from the 1960s until the mid 1980s. Also, the street crew extended into East Boston, Roxbury, Waltham, Newton, Watertown, parts of Revere, and all other predominantly Italian American neighborhoods in Eastern Massachusetts. Their criminal organization was dubbed "In-Town", because one had to go in to town to visit the Angiulo Brothers.
Joseph Barboza Jr., nicknamed "the Animal", was an American mobster and notorious mob hitman for the Patriarca crime family of New England during the 1960s. A prominent enforcer and contract killer in Boston's underworld, Barboza became a Federal Bureau of Investigation (FBI) informant in 1967 and later entered the Witness Protection Program. He was a star witness in the trial of six men convicted in the 1965 murder of Edward Deegan; four of the accused were sentenced to death and another two were sentenced to life imprisonment. It later emerged that Barboza had helped frame the six defendants in a case of wrongful conviction for the Deegan killing, which was allegedly actually committed by Barboza and Vincent Flemmi. He was shot dead in San Francisco in 1976 after his whereabouts became known to Patriarca underboss Gennaro Angiulo.
Roger Milton Wheeler Sr. was an American businessman from Tulsa, Oklahoma, the former chairman of Telex Corporation, and former owner of World Jai Alai. He was murdered by members of organized crime who discovered that Wheeler had uncovered their embezzlement scheme at World Jai Alai.
Kevin Weeks is an American former mobster and longtime friend and mob lieutenant to Whitey Bulger, the infamous boss of the Winter Hill Gang, a crime family based in the Winter Hill neighborhood of Somerville, Massachusetts.
Angelo "Sonny" Mercurio was an Italian-American mobster and a member of the Patriarca crime family who became an FBI informant that recorded for the first time a mafia induction ceremony. This recording led to the incarceration of family boss Raymond Patriarca, Jr. and several other high ranking mafioso. It also became a source of embarrassment for the organization. Subsequently after incarceration Mercurio was entered into the Witness Protection Program.
John Vincent Martorano is an American former gangster and former hitman for the Winter Hill Gang in Boston, Massachusetts, who has admitted to 20 mob-related killings.
Richard J. Castucci Sr. was an American member of the Patriarca crime family who owned several strip clubs and was involved in illegal gambling. Castucci eventually became a government informant.
James Martorano is an American organized crime figure with ties to the Winter Hill Gang of South Boston, Massachusetts, and a member of the Patriarca crime family as of 1995. Martorano is the younger brother of notorious "hitman" and later government witness, John Martorano.
Timothy A. Connolly III, aka "Timmy Connolly" and "TC", was an American former South Boston bar owner and mortgage broker, who wore a wire inside the infamous Winter Hill Gang and helped the federal government indict their two leaders, James "Whitey" Bulger and Stephen Flemmi. The public was led to believe that Tim Connolly was merely a businessman and an innocent victim of one of Jim Bulger's many extortions. But in truth, Tim Connolly was secretly a "made member" of the Winter Hill gang and a high ranking lieutenant in this Bulger crime family.
The 1978 Blackfriars Massacre, also known as the Blackfriars murders, is an unsolved Irish Mob and/or Italian-American Mafia massacre that occurred on June 28, 1978, in the Blackfriars Pub in Downtown Boston, Massachusetts. Four criminals known to the police and a former Channel 7 Boston television investigative news anchorman, Jack Kelly, were killed, allegedly over the sale of cocaine.
Michael S. Flemmi is an American retired Boston Police Department officer who was convicted of obstruction of justice charge stemming from his relationship with his brother Stephen Flemmi and the Winter Hill Gang.
Gennaro Joseph "Jerry" Angiulo Sr. was an American mobster who rose to the position of underboss in the Patriarca crime family of New England under Raymond L. S. Patriarca. Angiulo was convicted of racketeering in 1986 and was imprisoned until being released in 2007. According to a member of the Angiulo Brothers, he was "probably the last very significant Mafia boss in Boston’s history".
Black Mass is a 2015 American biographical crime drama film about American mobster Whitey Bulger. Directed by Scott Cooper and written by Mark Mallouk and Jez Butterworth, it is based on Dick Lehr and Gerard O'Neill's 2001 book Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob. The film features an ensemble cast led by Johnny Depp as Bulger, alongside Joel Edgerton, Benedict Cumberbatch, Kevin Bacon, Jesse Plemons, Peter Sarsgaard, Dakota Johnson, and Corey Stoll.
John Morris is an American former FBI agent who was charged with corruption for his involvement with James "Whitey" Bulger, Steve Flemmi and the Winter Hill Gang. He was the direct supervisor of John Connolly, who was convicted of racketeering, obstruction of justice and murder. He and Connolly compiled much of Bulger's 700-page FBI informant file. Morris met Bulger for the first time in 1978, when Morris hosted a dinner at his home in Lexington, Massachusetts. Morris was put in charge of the Organized Crime Squad at the FBI's Boston field office in December 1977. Morris not only proved himself unable to rein in Connolly's protection of Bulger, but even began assisting him.
Jeremiah T. O'Sullivan was a Boston-based federal prosecutor for the United States Department of Justice. In 2012, he was identified as the federal agent who, it is believed, provided immunity to Winter Hill Gang leader James "Whitey" Bulger. Bulger was accused of racketeering and being involved in nineteen murders. O'Sullivan was a lawyer in the 1970s and 1980s, prior to becoming the head of the New England Organized Crime Strike Force. In 1970, he was the Deputy Assistant Attorney-General for the Commonwealth of Massachusetts.
↑ Boeri, David (May 22, 2013). "Bulger on Trial". WBUR. Retrieved November 30, 2018.
↑ Grunwald, Michael (January 12, 1999). "A gang's unlikely ally: the FBI". The Washington Post. Retrieved November 30, 2018. ...Connolly, 58, who...has a keen sense of public relations and a master's degree from Harvard...
↑ Lehr, Dick; Murphy, Shelley (July 19, 1998). "Agent, mobster forge a pact on old Southie ties". The Boston Globe. Archived from the original on October 5, 2002. Retrieved November 30, 2018. ...Connolly had been in the Boston office of the FBI for two years, having won a transfer from New York in 1973.
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