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.
Early years
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, Puglia, 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 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. He was awarded the Silver Star and Bronze Star Medal decorations for valor and honorably discharged in 1955.
Relationship with James J. Bulger
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 Killeen. After Killeen was murdered by an enforcer for the Mullen Gang, Winter Hill Gang boss Howie Winter mediated the dispute between Bulger and the remaining Killeens and the Mullens, who were led by Patrick Nee. Winter soon chose Bulger as his man in South Boston. Shortly afterward, Bulger became partners with Flemmi.
At this time, the Boston FBI office tried to convince Bulger to become an informant, but he refused.
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. 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.
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 Davis and Michelle Davis, and Deborah Hussey. Flemmi met Debra Davis at a jewelry store, and the couple dated for more than seven years. In 1981, Bulger is said to have killed Davis because she knew that Flemmi was an informant.
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 garrotted her. Her body was then buried in the basement. According to Kevin Weeks,
Relationship with the FBI
Rico first recruited Flemmi as an informant in 1965.
In 1997, shortly after The Boston Globe disclosed that Bulger and Flemmi had been informants, former Bulger confidant Kevin Weeks met with John 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,