Vincent J. “Jimmy the Bear” Flemmi, DOB 9-5-35. Hitman brother of Whitey’s partner, Stevie Flemmi. In and out of prison after 1969, later released under Gov. Dukakis’ weekend-furlough program for vicious killers. Like Willie Horton, once they cut him loose the Bear never looked back. Escaped from Massachusetts after unsuccessfully trying to murder a woman (and settling from strangling her cat). Recaptured in Baltimore in 1978 after assaulting a woman, died a year later at MCI-Norfolk of a drug overdose. (Now do you understand why in some other photos on Whitey Watch, the Bear is always wearing a hat or cap?)

 Jimmy the Bear was released first and became a feared gangland killer while Benjamin languished in the can. Finally, in 1964, Benjamin was released from prison, and soon stopped into one of the Bennett brothers’ buckets of blood in Dorchester for a cocktail, where Jimmy the Bear was also hanging out. At some point, for reasons that remain obscure, Jimmy the Bear became annoyed enough with his old pal to borrow a gun, which he then used to shoot Benjamin in the head. Normally, Frankie’s intact corpse would have been dropped somewhere far from where the murder occurred – Southie, say. But there was a problem: Jimmy the Bear had used a cop’s gun, which made a ballistics test very risky for all concerned. So Jimmy the Bear decided to saw off the head (where the bullets were) and dispose of it separately from the body.

This, however, created such a mess in the taproom that the boys decided they’d better torch the building too, to destroy any lingering evidence. A day or so later, Benjamin’s headless body was discovered in the back of a stolen car… in Southie. Frankie Benjamin’s head was never recovered. Soon thereafter, Mafia underboss Gerry Angiulo delivered a personal message to Jimmy the Bear from “the Man,” Raymond L.S. Patriarca: You can’t keep killing people just because they look at you the wrong way.

Despite the warning, Jimmy the Bear continued killing people because they looked at him the wrong way. He died of a drug overdose at MCI-Norfolk in 1979.