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Stephen Joseph Flemmi (born June 9, 1934) 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).
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.
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.
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. The George Hamilton Cold Case: How to Get Away With Murder Carly Carioli, Boston (February 11, 2024)
During the 1960s, gang warfare erupted in Boston and across New England, with Irish and Italian gangsters battling over control of lucrative criminal rackets. Mob and FBI have violent history David D. Haskell, United Press International (May 4, 2001) The fiercest fighting involved two rival Irish mob groups, the Winter Hill Gang and the Charlestown Mob. Flemmi and his friends Joseph Barboza and 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 American 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 (FBI) 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. Former mob boss tells of access to FBI Shelley Murphy, The Boston Globe (February 13, 2004) 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.Howie Carr (July 26, 2009). "Rifleman's 'Fifth' toll rises". Boston Herald. Flemmi and Salemme first attempted to murder McLaughlin when they shotgunned him in the parking lot of Beth Israel Hospital while disguised as . 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, 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.
target="_blank" rel="nofollow"> Emily McIntyre and Christopher McIntyre v. the United States Casetext (September 5, 2006)
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, ‘Rifleman’: Flemmi thought about killing his pal Whitey Howie Carr, Boston Herald (April 8, 2013) a rivalry persisted between Bennett and Ilario Zannino, Flemmi and Salemme's closest contact in the Mafia.
target="_blank" rel="nofollow"> United States of America v. Francis P. Salemme Casetext (December 23, 1999) Flemmi and Salemme shot and killed the brothers "Wimpy" and Walter Bennett in succession. Asked to identify mob boss, witness says: 'I can't see him' Brian Amaral, The Providence Journal (June 6, 2018) At the behest of Zannino, 47-year-old "Wimpy" Bennett was murdered in a garage owned by Salemme on January 19, 1967.Carr, Howie (March 2, 2008). "Mobster of the Week: Peter Poulos". Boston Herald. After Bennett disappeared, Flemmi notified his FBI Agent handling 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. Two Fugitives Indicted for Bombing Ronald A. Wysocki, The Boston Globe (October 10, 1969) 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. Former Mob Enforcer Recounts Murders At Boss Frank Salemme's Request Isiah Thompson, WGBH Educational Foundation (June 6, 2018) While driving across the country with Poulos, Flemmi shot and killed his associate outside Las Vegas because he and Salemme "felt Poulos 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.
Bulger joined Flemmi in the Top Echelon informant program in 1975 when he was recruited by the FBI agent John "Zip" Connolly. Whitey Bulger's Trial Conspiracy: John Connolly Speaks T.J. English, Newsweek (June 18, 2012) Assets and Liabilities Patrick Radden Keefe, The New Yorker (September 14, 2015) 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. Detective dents Rico case after decades of pursuit Kelly Kurt, The Standard-Times (October 20, 2003) The Paul Rico Case FBI Studies (June 14, 2016) 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 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. Agents gave Bulger starring role - but was it real? Gerard O'Neill, The Boston Globe (June 11, 2014) 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. United States of America v. Stephen J. Flemmi FindLaw (September 11, 2000)
Flemmi met Debra Davis at a jewelry store after his return to Boston in 1974, and the couple dated for more than seven years. They lived together at an apartment in Randolph, along with Davis' sister, Michelle. Family of mobster’s murdered girlfriend awarded $33.5 million – but gangsters are unlikely to pay John P. Kelly, The Patriot Ledger (September 18, 2009) Flemmi and Davis' relationship became strained after Flemmi began sexually abusing 14-year-old Michelle Davis. During an argument at the Bay Tower Room restaurant at 60 State Street, Flemmi, in frustration, tacitly admitted to her that he and Bulger were FBI informants. An enraged Bulger then allegedly insisted that Davis be killed, to which Flemmi acquiesced. On September 17, 1981, 26-year-old Davis was strangled to death in the basement of Flemmi's mother's home in South Boston. Flemmi claimed that Davis was murdered by Bulger. According to John Martorano, Flemmi admitted that he had "accidentally" strangled her himself. Flemmi pulled out Davis' teeth and cut off her hands to complicate identifying the body, and she was buried at Tenean Beach on the Neponset River in North Quincy. As he and Bulger buried the body, Flemmi claimed to have considered killing Bulger for the murder. Flemmi misled Davis' mother Olga into thinking her daughter had moved to Texas. Wracked with shame and guilt over the abuse she had suffered at the hands of Flemmi, Michelle Davis fell into drug addiction and alcoholism, and died from a drug overdose in January 2006.
Four years after killing Davis, in 1985, Flemmi and Bulger killed Deborah Hussey, who was also Flemmi's stepdaughter (born to his common-law wife, Marion A. Hussey). Deborah was first sexually molested by Flemmi in her teens—she informed her mother that Flemmi had molested her for years—and had been his girlfriend since. In the days prior to her murder, Hussey was close to breaking up with Flemmi and telling her mother about their relationship, which is thought to have been the motive for her murder.
It is thought that Flemmi, Bulger, and Weeks lured her to the house at 799 East Third Street in South Boston and her. Her body was then buried in the basement. According to Kevin Weeks,
By 1991, Salemme was the de facto leader of the Mafia in New England. To assure his position as the head of the Patriarca family, Salemme built an alliance between the Mafia and the Winter Hill Gang, effectively uniting Boston's Italian and Irish crime groups. Reputed Mafia leader arrested after 2 years Tampa Bay Times (August 13, 1995) Flemmi and an associate, George Kaufman, served as the liaisons between the Winter Hill Gang and the Patriarca family. Feds indict alleged New England mob bosses United Press International (January 10, 1995) Nonetheless, Bulger and Connolly's plan to sow discontent in the Patriarca family to prevent the Mafia from usurping the Winter Hill Gang as Boston's preemeninent organized crime force succeeded as the Patriarca family descended into a state of internal warfare following the shooting of Salemme.
According to Flemmi, he witnessed the murder of nightclub owner Steven DiSarro when he happened to visit Salemme's home in Sharon on May 10, 1993, walking in on Salemme's son, Francis "Frankie Boy" Salemme Jr., strangling DiSarro as an associate, Paul Weadick, held his legs and Salemme Sr. looked on. 'Pure evil': Ex-New England mob boss gets life in prison for 1993 murder Nate Raymond, Reuters (September 14, 2018) Salemme had ordered DiSarro's murder over fears he may cooperate with a federal investigation into illegal activities at the Channel nightclub in South Boston, in which Salemme and his son held a financial interest. Former Mafia Boss and Associate Convicted of 1993 Murder United States Department of Justice (June 22, 2018) DiSarro was buried behind a mill in Providence, Rhode Island.
In April 1994, a joint task force of the Drug Enforcement Administration (DEA), the Massachusetts State Police, and the Boston Police Department launched an investigation into gambling operations in which the Winter Hill Gang and the Patriarca family collaborated. Photos: Who's Who in the Bulger Case WCVB-TV (June 25, 2011)
According to Kevin Weeks,
Flemmi, however, miscalculated how soon the arrests would take place and remained in Boston. On January 5, 1995, he was arrested by the state police as he left Schooner's Restaurant in a car along with a woman companion. A bewildered Flemmi asked agents "Is this a gag?" as he was being arrested. Howie Carr: Happy 90th birthday to Stephen ‘The Rifleman’ Flemmi, Boston’s most prolific serial killer Howie Carr, Boston Herald (June 9, 2024) He was held without bail and incarcerated at the Plymouth County House of Correction. Flemmi's son to testify against father in court Martin Finucane, The Standard-Times (December 15, 2000)
During the discovery phase, two of Flemmi's co-defendants, Boston mafiosi Frank Salemme and Bobby DeLuca, were listening to tape from a roving bug, which is normally authorized when the FBI has no advance knowledge of where criminal activity will take place. They overheard two of the agents who were listening in on the bug mention that they should have told one of their informants to give "a list of questions" to the other wiseguys. When their lawyer, Tony Cardinale, learned about this, he realized that the FBI had lied about the basis for a roving bug in order to protect an informant. Suspecting that this was not the only occasion that this happened, Cardinale sought to force prosecutors to reveal the identities of any informants used in connection with the case.
Eventually, both Bulger and Flemmi were revealed to be FBI informants. Flemmi believed that as a result, he had protection from the FBI, but not immunity. He initially planned to prove through his own testimony and that of others that he was being prosecuted for crimes that were effectively authorized by the FBI. He believed that as a result, Judge Mark L. Wolf would have no choice but to throw out the entire indictment. Flemmi's problem was that, without immunity, he could not admit to killings he had not been charged with. By the time Flemmi took the stand, in August 1998, John Martorano had pleaded guilty and started outlining the details of almost twenty murders he'd committed. Many of his murders had been done at the direction of Bulger and Flemmi, who had paid him more than $1 million during his years as a wanted fugitive between 1978 and 1995. To many questions about the murders Flemmi was involved in, he pleaded the Fifth Amendment.
However, by 2000, it was obvious this gambit had failed. Out of desperation, he ordered Weeks to get in touch with retired state police lieutenant Richard J. Schneiderhan, a lifelong friend who had been on Winter Hill's payroll for virtually his entire career, to leak information about several wiretaps investigators were monitoring in hopes of tracking down Bulger. However, when Weeks reached a plea bargain a year later, he admitted Schneiderhan's role in the leak. Schneiderhan was ultimately convicted of obstructing justice and was sentenced to 18 months in prison. In 2000, Flemmi's brother Michael, then a retired Boston Police Department officer, was arrested for moving an arsenal of more than 70 weapons from their mother's shed after learning that it was to be the target of a search warrant. He was convicted in 2002 and sentenced to 10 years in prison. A year later, he pleaded guilty to selling a load of Flemmi's stolen jewelry for $40,000.
By 2003, Flemmi realized he was out of options. Salemme and several others had joined Weeks in turning informer, and had disclosed enough information to ensure Flemmi would die in prison. He also faced possible execution for murders in Florida and Oklahoma. In October, Flemmi pleaded guilty in U.S. District Court in Boston to 10 counts of murder and accepted a sentence of life in prison without parole. "Winter Hill Gang Leader Pleads Guilty" Drug Enforcement Administration. October 14, 2003. As a part of a deal, the sentence given to his brother, Michael, was reduced.
Flemmi testified against Connolly at the latter's trial for the murder of John Callahan, the former president of World Jai Alai. Callahan had been killed in 1981 after he was implicated in the murder of his successor as president, Roger Wheeler. According to Flemmi, Connolly told him and Bulger that Callahan could potentially turn state's evidence and implicate them in Wheeler's murder. He also testified against Bulger in the latter's 2013 trial for murder and racketeering, at which Bulger was sentenced to life plus five years.
As a cooperating witness, Flemmi is held in an undisclosed penitentiary as part of the Federal Bureau of Prisons' Witness Security (WitSec) program.On August 18, 2021, Flemmi was denied parole by the Florida Commission on Offender Review after seeking compassionate release. His next review is not scheduled until 2028, when he will be 93 years old. His parole is scheduled for May 4, 2218.
Married life
In the 1950s, Flemmi was married to an Irish-American woman named Jeanette, from whom he later became estranged. By 1980, he planned to divorce Jeanette to marry his longtime mistress, Marilyn DeSilva, but it is unknown whether he ever followed through with the legal actions. Throughout his life, Flemmi was engaged in clandestine affairs with several other women, including sisters Debra and Michelle Davis, and Deborah Hussey. According to Salemme: "There's two things with Flemmi paramount to everything – his money and his women, not necessarily in that order". Howie Carr: Final look at Salemme’s history before sentencing Howie Carr, Boston Herald (June 24, 2018)
Relationship with Frank Salemme
Flemmi's longtime partner Salemme was released from state prison in 1988 after serving fifteen years for the attempted murder of Fitzgerald, Frank Salemme, One-Time Head of the New England Mafia, Dies at 89 Clay Risen, The New York Times (December 21, 2022) and was subsequently inducted as a "Made man" member of the Patriarca family. ‘Cadillac Frank’ Salemme obituary The Times (December 29, 2022) To the disillusionment of Bulger, Flemmi drifted closer to Salemme and the Patriarca family as Salemme attempted to recruit him into the Mafia. Using his contacts with Connolly, Bulger plotted to have Salemme eliminated by his own crime family. Connolly had a story planted in a newspaper falsely stating that Salemme was planning to eradicate the East Boston faction of the Patriarca family. On June 16, 1989, Salemme survived a murder attempt when he was shot by East Boston mobsters outside a pancake house in Saugus.
Arrest and imprisonment
By the end of 1994, the Massachusetts State Police and the U.S. Attorney's Office had amassed enough evidence to indict Flemmi, Bulger and Salemme on 35 counts of racketeering and extortion. Galway native set to testify against Bulger in murder trial Pierce O’Reilly, The Irish Echo (February 16, 2011) In December 1994, Connolly informed Bulger and Flemmi that several imprisoned Jewish-American bookmakers had agreed to testify to paying them protection money. As a result, sealed indictments had come from the Department of Justice, and the FBI was due to make arrests during the Christmas season. Mobster tells of gang payoffs to FBI United Press International (May 16, 2002) In response, Bulger fled Boston on December 23, 1994, accompanied by his common law wife, Catherine Greig. Bulger girlfriend testifies at mob trial Curt Anderson, Telegram & Gazette (October 17, 2008) Flemmi in turn warned Salemme, Bulger’s long ties to south suburbs The Boston Globe (February 12, 2012) who took flight to Providence and then West Palm Beach, Florida. When The Feds Moved In, Whitey Slipped Away David Boeri, WBUR-FM (January 5, 2010)
Victims
Murdered
Others
Stephen Flemmi and Whitey Bulger are alleged to have committed statutory rape against numerous underage girls, some as young as 13, during the 1970s and 80s, deliberately getting them hooked on heroin and then sexually exploiting them for years.
Depictions in popular culture
In the Whitey Bulger biopic Black Mass (2015), Flemmi is portrayed by Rory Cochrane.
See also
Further reading
External links
Categories: 1934 Births, Living People, 20th-century American Murderers, American Male Criminals, American Gangsters Of Italian Descent, American People Convicted Of Murder, American Prisoners Sentenced To Life Imprisonment, American Rapists, Fbi Informants Convicted Of Crimes, Gangsters From Boston, Gangsters Sentenced To Life Imprisonment, Mafia Hitmen, Military Personnel From Massachusetts, Patriarca Crime Family, People Convicted Of Murder Under The Rico Act, People From Milton, Massachusetts, Police Informants, Recipients Of The Silver Star, United States Army Personnel Of The Korean War, United States Army Soldiers, Winter Hill Gang, Child Sexual Abuse In The United States
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