Stephen Flemmi

Stephen Joseph Flemmi (born June 9, 1934) is an American former mobster 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.

Early life

Stephen Joseph Flemmi was the eldest of three sons (the two brothers were Michael Flemmi and Vincent Flemmi) born to Italian American parents Giovanni "John" Flemmi (1892–1991), an immigrant from Bari, Apulia, and Mary Irene (née Misserville) Flemmi (1912–2000), 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 awarded the Silver Star and Bronze Star Medal decorations for valor and honorably discharged in 1955.

Criminal career

After leaving the military, Stephen 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. Flemmi became a protégé of Walter and "Wimpy" Bennett, taking and collecting bets for the brothers' numbers racket, which they ran from their headquarters at Walter's Lounge, a Dudley Street nightclub. A handsome, 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 "Bill" 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 fiercest fighting involved two rival Irish mob groups, the Winter Hill Gang and the Charlestown Gang. In addition to his links with Irish gangsters in Somerville, Flemmi associated with the Italian Mafia. Flemmi described his relationship with Rico and his partner, Dennis Condon, as "quid pro quo". 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.

Bennett murders and Fitzgerald bombing

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. At the behest of Zannino, After Bennett disappeared, Flemmi notified his FBI handler Rico that there was "absolutely no chance" that he would be found alive.

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. Fitzgerald survived but lost his lower right leg in the explosion. 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". In 1974, Bulger became partners with Flemmi as enforcers for the Winter Hill Gang. 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. 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 gone 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. 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.

Married life

In the 1950s, Flemmi was married to Jeanette McLaughlin, an Irish-American woman with whom he had two daughters. Although Flemmi left McLaughlin, they remained married until their divorce in 1980. After becoming estranged from his wife, Flemmi was involved in a decades-long relationship with Marion Hussey. Flemmi and Hussey lived together in Dorchester and Milton, and had three children, two sons and a daughter. Flemmi was also the stepfather of Deborah Hussey, Marion Hussey's daughter from a previous relationship. Throughout his life, Flemmi was engaged in clandestine affairs with several other women, including Shirley Rogers, Marilyn DiSilva, sisters Debra and Michelle Davis, and his stepdaughter Deborah Hussey. According to Salemme: "There's two things with Flemmi paramount to everything—his money and his women, not necessarily in that order".

Even while in relationships, Flemmi engaged in frequent liaisons with college girls at cocaine-fuelled parties hosted by John Martorano, although he himself was not a drug user. Flemmi and Bulger are also alleged to have committed statutory rape against numerous underage girls, some as young as 13, during the 1970s and 1980s, deliberately getting them hooked on heroin and then sexually exploiting them for years.

Flemmi first met Debra Davis in 1972 when he was 38 years old and she was 17 and working in a jewelry store in suburban Brookline. The couple dated for more than seven years. They lived together at an apartment in Randolph, along with Davis' younger sister, Michelle. Flemmi and Davis' relationship became strained after Flemmi began sexually abusing 14-year-old Michelle Davis. Afterwards, Debbie Davis decided to leave Flemmi for a Mexican businessman she had met on vacation in Acapulco. The FBI never questioned Flemmi about Davis' disappearance, however.—and had been his girlfriend since. Hussey later developed a drug addiction and turned to prostitution. and was subsequently inducted as a "made" member of the Patriarca family. 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. Flemmi and an associate, George Kaufman, served as the liaisons between the Winter Hill Gang and the Patriarca family. 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 preeminent 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 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. Flemmi's son, William "Billy" Hussey St. Croix, however, stated in a debriefing that Flemmi had told him that his presence at Salemme's home that day was not a mere coincidence and that Flemmi was in fact involved in DiSarro's murder. DiSarro was buried behind a mill in Providence, Rhode Island.

Arrest and imprisonment

thumb|right|Flemmi's January 5, 1995 FBI mugshot

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. 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. In response, Bulger fled Boston on December 23, 1994, accompanied by his common law wife, Catherine Greig. Flemmi in turn warned Salemme, who took flight to Providence and then West Palm Beach, Florida.

According to Kevin Weeks,

Flemmi, however, miscalculated how soon the arrests would take place and remained in Boston. He was held without bail and incarcerated at the Plymouth County House of Correction. Prosecutors gained sufficient evidence to bring murder charges against Flemmi after Hugh Shields became a government witness in 1995. On May 21, 1996, four charges of murder—those of Edward, Walter and William Bennett, and Richard Grasso—were added to a superseding indictment against Flemmi and Salemme.

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. 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.

Victims

===Murdered===

Arthur "Bucky" Barrett
Edward Bennett
Walter Bennett
William Bennett
Richard Castucci
Edward G. Connors
Debra Davis
Richard Gasso
Stephen Hughes Jr.
Deborah Hussey
Tommy King
John McIntyre
Edward McLaughlin
James Sousa
Roger Wheeler

Depictions in popular culture

In the Whitey Bulger biopic Black Mass (2015), Flemmi is portrayed by Rory Cochrane.

References

External links