Vincent James Flemmi (1935–1979), also known as "Jimmy The Bear," was an Italian-American mobster who freelanced for the Winter Hill Gang and the Patriarca crime family. He was also a longtime informant for the Federal Bureau of Investigation. He was also the brother of government informant Stephen Flemmi.
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Vincent J. Flemmi was born to Italian immigrants Giovanni Flemmi and Mary Irene Flemmi. He was raised in the Orchard Park tenement located at 25 Ambrose Street in Roxbury, Massachusetts. His father Giovanni was a bricklayer who, according to fellow mobster Kevin Weeks, served in the Royal Italian Army during World War I. His mother was a full-time homemaker who never lost her thick Italian accent. He was the brother of Stephen Flemmi and Michael S. Flemmi.
During the Boston gang wars of the 1960s, Vincent, along with Joseph Barboza became so feared, that the city's newspaper photographers often attached a note on the back of their arrest photos: "NO credit on photograph."
In May 1964, FBI Special Agent John Connolly filed a report on a conversation another one of his informants had with Vincent: "Flemmi told him all he wanted to do now is kill people, and that it is better than hitting (robbing) banks." Vincent's homicidal tendencies became so out of hand that Gennaro Anguilo held a sit down with Vincent inside an FBI-bugged room on Tremont Street. From now on, Anguilo told him—Raymond Patriarca would have to approve each of his hits, personally, just as he had done with Joseph Barboza. In March 1965, H. Paul Rico wanted to make Vincent a Top Echelon Informant for the FBI. On March 10, 1965 H. Paul Rico filed a report quoting an informant as saying that Vincent was going to murder Edward Deegan and that a "dry run has already been made and that a close associate of Deegan's has agreed to set him up." Two days later, despite their knowledge of the impending murder of Deegan, the Boston FBI office approved Vincent as an informant and assigned him to the agent who had recruited him, H. Paul Rico.
That evening, Edward Deegan was shot to death by Vincent Flemmi and Joseph Barboza, among others in an alleyway in Chelsea, Massachusetts. Within hours, J. Edgar Hoover had a memo from the Boston field office on his desk accurately identifying all the shooters, the actual shooters, as opposed to the four innocent men who would be convicted of the crime on the false testimony of Joseph Barboza in 1968.
Radio talk host Howie Carr would later surmise, "For the FBI, it was more important to keep Vincent, and later Barboza, on the street as informants than it was to prevent the framing of innocent men. In fact, the railroading of the four men served two purposes for the FBI, it would enable Vincent and Joseph Barboza to escape conviction for a murder they had committed, and it would also remove several Patriarca crime family members or associates from the criminal world that the FBI had not been able to eliminate in a legal manner". One of Deegan's friends told him about a bank burglary in Chelsea, and he'd meet up with several guys from Ebb Tide, a Mafia-run gin mill on Revere Beach. Vincent's shooting party would include mob associate, Joseph Barboza.
Theodore Deegan was a maternal nephew of Bonanno crime family capo Alphonse Indelicato and Anthony Indelicato.
According to Kevin Weeks, a longtime associate of Flemmi's brother Stephen,
"The murder of Francis Benjamin, for which the Bear had gotten the life sentence, was a particularly ugly one. After he'd shot Benjamin in the head, using a gun that belonged to a cop, the Bear had cut off the head to avoid any ballistics evidence tracing the gun to the crime. But they fingered him anyhow."[1]
In 1975, while serving an eleven-to-eighteen-year sentence for assault with intent to commit murder, he'd received one of the state's first weekend furloughs from prison. Vincent had immediately fled, and was not apprehended until three years later, in Maryland, Maine. On October 16, 1979, Vincent died of an apparent heroin overdose at the state prison in Norfolk, Massachusetts.
According to South Boston mob boss Kevin Weeks,
"When Stevie's brother Jimmy the Bear died of a heroin overdose while serving a life sentence at MCI Norfolk for the murder of Francis Benjamin, Jimmy and I went to the wake. While we were viewing his brother lying in the casket, Stevie was standing there with his mother and father and Michael. Mary went over to Jimmy and said, crying, 'Vincent was such a good boy. He never hurt anyone.' Stevie looked at her and said, 'Stop, Ma. He killed everybody.'"[2]
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