Stephen Flemmi


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.
Despite delivering a great deal of intelligence about the inner workings of the Patriarca crime family, Flemmi's own criminal activities proved a public relations nightmare for the FBI. He was ultimately brought up on charges under the Racketeer Influenced and Corrupt Organizations Act, and pleaded guilty in return for a sentence of life in prison.

Early life

Stephen Joseph Flemmi was the eldest of three sons born to Italian American parents Giovanni "John" Flemmi, an immigrant from Bari, Apulia, and Mary Irene Flemmi, who was born in Massachusetts to a family from Ceccano, Lazio. He was raised in the Orchard Park tenement located at 25 Ambrose Street in the Roxbury neighborhood of Boston, Massachusetts. His father was a bricklayer and veteran of the Royal Italian Army during World War I, and his mother was a full-time homemaker.
Flemmi was first arrested at the age of 15 on a charge of "carnal abuse", and he later served time in a juvenile detention facility for assault. He enlisted in the Army in 1951 at the age of 17 and served two tours of duty in Korea with the 187th Airborne Regimental Combat Team. Flemmi was awarded the Silver Star and Bronze Star Medal decorations for valor and honorably discharged in 1955.

Criminal career

After leaving the military, Steve "The Rifleman" Flemmi, along with his brother Vincent, joined the Roxbury Gang in the late 1950s. The gang was led by the brothers Walter, William and Edward "Wimpy" Bennett and controlled bookmaking and drug dealing in the Roxbury and South End neighborhoods of Boston. A soft-spoken and slender man of around 5-feet-8 and 140 pounds, Flemmi operated out of the Marconi Club, a combination bookmaker's, massage parlor and brothel, in Roxbury. Although he had a reputation as a ruthless killer, Flemmi was a popular man who was fond of nightlife, cars and the company of young women.
Flemmi, along with his mentors Walter and "Wimpy" Bennett, became a confidential informant for the Boston Police Department detective William Stuart, who offered protection to the gangsters in exchange for information on their criminal rivals. In September 1964, Stuart saved the lives of Stephen Flemmi and his brother Vincent by intervening at gunpoint to stop the hoodlum William McCarthy from gunning down the pair. McCarthy had sought revenge on the Flemmi brothers after Vincent Flemmi had killed his associate, Leo Lowry.
During the 1960s, gang warfare erupted in Boston and across New England, with Irish and Italian gangsters battling over control of lucrative criminal rackets. The fiercest fighting involved two rival Irish mob groups, the Winter Hill Gang and the Charlestown Mob. Flemmi and his friends Joseph "the Animal" Barboza and Francis "Cadillac Frank" Salemme were recruited by the Winter Hill Gang and fulfilled a string of lucrative murder contracts during the gang wars. In addition to his links with Irish gangsters in Somerville, Flemmi associated with the Italian Mafia. Flemmi formed a partnership with his childhood friend Salemme, and the duo became enforcers, bookmakers and loan sharks for the Patriarca crime family in Boston's North End.
Flemmi was recruited as an informant for the Federal Bureau of Investigation in the mid-1960s, adopting the code name "Jack from South Boston". The FBI later referred to Flemmi as "Shogun". By the fall of 1965, Flemmi was being supervised by the FBI agent H. Paul Rico. Rico had cultivated Flemmi as an informant due to his association with the Patriarca family. Because of Flemmi's ability to provide information on the family's leadership, Rico had him designated a Top Echelon informant, the highest status an FBI source can achieve. Due to the shifting alliances and ongoing killings during the gang wars, Flemmi's life was constantly under threat, and he relied on Rico to alert him to any threats he may have learned from other informants. Because of Flemmi's usefulness as an informant, Rico overlooked Flemmi's criminal activities. By the late 1960s, Flemmi was a suspect in several murders, but the FBI chose not to question him about the killings.
Rico leaked information to members of the Winter Hill Gang which allowed them to track down and kill rival gangsters. Rico had been offended when he heard the Charlestown gangster Edward "Punchy" McLaughlin refer to Rico and his boss, J. Edgar Hoover, as "fags" on an illegal wiretap, and, in retaliation, alerted McLaughlin's rivals of his location. Flemmi and Salemme first attempted to murder McLaughlin when they shotgunned him in the parking lot of Beth Israel Hospital while disguised as rabbis. McLaughlin had his jaw blown off but survived. On the second attempt, Flemmi and Salemme fired upon McLaughlin with machine guns during an ambush as he arrived at a girlfriend's house in Weston. Although the pair missed their target, Howard "Howie" Winter shot McLaughlin's hand off with a scoped.308 Winchester rifle before he fled. McLaughlin was finally killed by two gunmen on a bus in West Roxbury on October 20, 1965. Flemmi and Salemme were alleged to be the two shooters.
Although Flemmi's first gangland boss, "Wimpy" Bennett, had vowed to remain neutral in a feud between the Patriarca family and an East Boston crew headed by Barboza, a rivalry persisted between Bennett and Ilario "Larry" Zannino, Flemmi and Salemme's closest contact in the Mafia. Flemmi and Salemme shot and killed the brothers "Wimpy" and Walter Bennett in succession. At the behest of Zannino, 47-year-old "Wimpy" Bennett was murdered in a garage owned by Salemme on January 19, 1967. After Bennett disappeared, Flemmi notified his FBI handler Rico that there was "absolutely no chance" that he would be found alive. 55-year-old Walter Bennett then went missing on April 3, 1967 after he had been deemed a threat to Flemmi. Both men were buried at a remote location in Hopkinton.
When the third Bennett brother, William "Billy" Bennett, "began vocalizing his belief that Flemmi had murdered both his brothers", Flemmi "reluctantly decided" that he too must be killed. 56-year-old Billy Bennett was dumped from a moving car and found dead against a snowbank in the Mattapan neighborhood of Boston on December 22, 1967 after getting into a vehicle with Richard Grasso, an associate from South Boston. Stuart assisted Flemmi in post-killing cleaning after Bennett's murder. A week later, Grasso was shot twice in the head and left in the trunk of his 1967 Buick Wildcat in Brookline. Grasso was killed by Flemmi after he had "panicked" because his car was used in Billy Bennett's murder. After the killings of the Bennett brothers, Flemmi assumed control of the Roxbury Gang.
In the summer of 1967, Zannino and Peter Limone decided to sponsor Flemmi and Salemme for membership in the Patriarca family. Although prospective members would ordinarily be required to carry out a murder in order to be inducted into the Mafia, the family offered to waive the requirement due to Flemmi and Salemme's reputation as seasoned killers. In the winter of 1967, Flemmi was summoned to Providence, Rhode Island to meet with Patriarca family boss Raymond Patriarca. Unlike Salemme, Flemmi ultimately resisted the family's attempts to recruit him as he did not trust the Mafia and felt he had sufficient protection as an FBI informant.
Flemmi was instrumental in Rico's efforts to develop Barboza into a cooperating witness for the government against the Patriarca family. After Barboza turned state's evidence, Raymond Patriarca ordered the murders of potential witnesses who might corroborate Barboza's testimony as well as Barboza's attorney, John E. Fitzgerald. On January 30, 1968, Flemmi and Salemme planted a car bomb under the hood of Fitzgerald's Cadillac automobile in Everett. Fitzgerald survived but lost his lower right leg in the explosion. According to Rico, in May 1968, Flemmi killed and buried Thomas Timmons, who had been involved in a dispute with the Patrarca family.
In September 1969, Flemmi was indicted by clandestine grand juries in two Massachusetts counties. He was charged in Suffolk County with the murder of William Bennett, and, along with Salemme, in Middlesex County with the attempted murder of Fitzgerald. After Flemmi was tipped off by Rico about the imminent indictments, he, Salemme and Peter Poulos, an associate of "Wimpy" Bennett in the South End who had witnessed Bennett's murder and assisted in the Fitzgerald bombing, fled Boston for the West Coast. After the trio made their way to Los Angeles, Salemme left to go into hiding on his own. While driving across the country with Poulos, Flemmi shot and killed his associate outside Las Vegas because he and Salemme "felt wouldn’t be able to stand up to pressure in court". Poulos' body was found in the Nevada desert in late 1969.
Flemmi spent four-and-a-half years as a fugitive, firstly in New York City and then in Montreal, where he worked as a printer at a newspaper. During his time on the run, Flemmi remained in contact with Rico, who kept him informed on the status of the cases against him. Rico also kept Flemmi's whereabouts confidential from Massachusetts authorities who were hunting him. After separating from Salemme because of a series of disagreements, Flemmi alerted the FBI to Salemme's location. As a result, Salemme was captured and sentenced to fifteen years in prison for the Fitzgerald bombing. The charges against Flemmi were ultimately dropped after key witnesses recanted their testimony, and Flemmi returned to Boston in May 1974.

Relationship with James J. Bulger and the FBI

In 1965, James J. "Whitey" Bulger was released from Federal prison after serving a nine-year sentence for robbing banks. After a few years of working as a janitor, he became an enforcer for South Boston mob boss Donald "Donnie" Killeen. After Killeen was murdered by an enforcer for the Mullen Gang, Winter Hill Gang boss Howard "Howie" Winter mediated the dispute between Bulger and the remaining Killeens and the Mullens, who were led by Patrick "Pat" Nee. Winter soon chose Bulger as his man in South Boston. At this time, the Boston FBI office tried to convince Bulger to become an informant, but he initially refused. In 1974, Bulger became partners with Flemmi as enforcers for the Winter Hill Gang.
Bulger joined Flemmi in the Top Echelon informant program in 1975 when he was recruited by the FBI agent John "Zip" Connolly. Bulger allegedly told Flemmi that he knew his secret. Flemmi has insisted that he did not know at the time that Bulger was also an informant. The mobster Kevin Weeks, however, insists that Flemmi's story is untrue. He considers it too much of a coincidence that Bulger became an informant a year after becoming Flemmi's partner. He has written of his belief that Flemmi had probably helped to build a Federal case against him. Weeks has said that Bulger was likely forced to choose between supplying information to the FBI or returning to prison.
Rico, Flemmi's initial handler, was transferred to the Miami office of the FBI in 1970 and retired in 1975. With assistance from Bulger, Connolly revived Flemmi's relationship with the FBI. Connolly served as the handler of Flemmi and Bulger from 1975 until his retirement in 1990. United by a shared antipathy for the Patriarca family, a desire to profit from its destruction, and the protection of the FBI, Flemmi and Bulger forged a formidable and enduring partnership. As the alliance between the gangsters and the FBI developed, Flemmi and Bulger dined periodically with FBI agents investigating the Mafia, including Connolly and several of his colleagues on the Boston Organized Crime squad, Connolly's supervisors, John Morris and James Ring, and Joseph D. Pistone, who had went undercover to infiltrate the Bonanno crime family in New York as "Donnie Brasco".
In 1997, shortly after The Boston Globe disclosed that Bulger and Flemmi had been informants, former Bulger confidant Kevin Weeks met with Connolly, who showed him a photocopy of Bulger's FBI informant file. In order to explain Bulger and Flemmi's status as informants, Connolly said, "The Mafia was going against Jimmy and Stevie, so Jimmy and Stevie went against them." According to Weeks,
Flemmi and Bulger assisted the FBI in planting a covert listening device in the headquarters of Patriarca family underboss Gennaro "Jerry" Angiulo at 98 Prince Street in the North End. At Morris' request, the duo visited the location in November 1980 and Flemmi subsequently produced a drawn diagram of Angiulo's office, which let FBI agents know exactly where to place bugs. Although Flemmi was concerned that information gathered on the wiretap may implicate him and Bulger in criminal activity, the FBI assured him that nothing on the tapes would be used against them.