Vincent James Flemmi was born on September 5, 1935, in Boston, Massachusetts—the younger brother of infamous mob figure Stephen Flemmi. Raised in the same Orchard Park tenement as his brothers, Vincent's parents—Giovanni and Mary Irene—provided little shield from the tough streets of Roxbury, where criminal talent was practically a family business.

By late 1950s, Vincent joined Stephen in the Roxbury Gang, under the Bennett brothers, engaging in bookmaking and drug dealing. He earned a fearsome reputation—so notorious that photo labs would label his mugshots with “NO credit on photograph,” a rare warning from newspaper editors.

The FBI recruited him as a Top Echelon informant in March 1965, even when there was intel suggesting his involvement in Edward Deegan’s murder. Despite informant status, Vincent spiraled into addiction. In 1975, he escaped custody during a weekend furlough. He was finally caught in Baltimore three years later for assaulting a woman, extradited to Massachusetts, and sent back to Walpole prison.

Vincent “Jimmy the Bear” Flemmi was far more than just a mob soldier; he was a lethal force with reach, reputation, and institutional protection. His first known foray into homicide emerged in May 1964, when the body of Francis Regis “Frank” Benjamin was discovered. Flemmi allegedly executed Benjamin with a police firearm and removed the head—clearly intending to foil ballistic evidence. The brutality of the act solidified his deadly reputation in Boston’s underworld.

Then came the notorious murder of Edward “Teddy” Deegan on March 12, 1965, at about 9:30 p.m., in a Chelsea alley. The crime was a revenge hit for Deegan’s theft from the Patriarca crime family. Two days before the killing, FBI memos already flagged Flemmi as planning the murder—mentioning that a “dry run” had been attempted and that Deegan was being set up. Yet despite this knowledge, the FBI appointed Flemmi as a Top Echelon Informant, illustrating a disturbing moral compromise.

Joseph “The Animal” Barboza eventually became the chief witness in the Deegan murder trial—testifying that Deegan’s murder had been sanctioned by the Patriarca family. Yet Barboza remains silent on Flemmi’s role, even though FBI files clearly indicated Flemmi as a direct participant. Four innocent men were wrongfully convicted in a gross miscarriage of justice—made possible by the FBI’s concealment of vital evidence to protect their informants.

Beyond these headline killings, Flemmi was embedded in the broader gang war landscape. He freelanced as muscle for both the Winter Hill Gang and the Patriarca family, executing contracts with cold precision. As his fame—and infamy—grew, so did efforts by his allies to contain his unpredictability. Salemme even enlisted Patriarca’s help to channel Flemmi’s wrath through supervised hits.

As the 1970s unfolded, Flemmi’s criminal life blended with drug addiction and instability. In the middle of an incarceration term, he secured a weekend furlough in 1975—but instead of stepping out for fresh air, he vanished. It was three years before he was arrested in Baltimore on assault charges and extradited back to Massachusetts.

Behind bars, addiction swallowed him. On October 16, 1979, Vincent died of a heroin overdose at Norfolk State Prison at just 44 years old.