The Murders of the Roxbury Gang’s Own Members- WILLIAM “BILLY” BENNETT

Like in the old Westerns, Wimpy and Walter’s elder brother, William “Billy” Bennett, decided he must find out what happened to his two younger brothers. Billy was known to carry his .38 caliber pistol with him in a shoulder holster. He was arrested in 1950 for booking but he was not as prominent in the rackets as his brothers.  Despite this, he felt obliged to do something about it and to take revenge on those who might have caused their disappearance.

He came to the conclusion that his brothers were slain by Flemmi and Salemme. Perhaps that was because he saw them moving in on his brothers’ businesses afterwards. He very well might have been getting a some income out of the businesses and now he was cut off.

Billy recruited a couple of guys to assist him in his plans to take down Flemmi and Salemme: Richard Grasso (discussed next) and Hugh “Sonny” Shields. Billy, said to have earned a living as a bartender, likely knew them from hanging around barrooms.  Grasso and Shields were wise enough to realize who held the power in this situation. They betrayed Billy by keeping Flemmi and Salemme updated on Billy’s plans.

The day before Billy’s murder, Flemmi, Salemme, Grasso, Shields, Poulos and Robert Daddieco met in an apartment to hash out the planned murder. On December 22, 1967, Grasso and Shields drove to pick Billy up at his house in Mattapan. Although skittish, Billy got into the car with them. Grasso and Shields planned to kill Billy in the car and then pass him off to Flemmi, Salemme, Poulos and Daddeico.  Salemme would then take him out to the Bennett Brothers Burial lot in Hopkinton. They had driven hardly a minute from Billy’s house when Shields aimed a gun at him.

Whether Billy smelled a rat and tried to bail out or the impact of the four shots from Shields’ gun thrust him against the car’s door, Billy’s body tumbled out of the car onto the street. Grasso and Shields drove another couple of blocks and abandon the car with the motor running. Salemme somehow arrives on the scene to pick up the body but a taxi driver pulls up next to the body before he can move it.

Firm evidence points to Flemmi, Salemme, Grasso and Shields murdering Billy. They targeted him because he had targeted them.  They learned he was gunning for them. It does not mean they were involved in the murders of his brothers.

Daddieco would turn state’s evidence. Flemmi, Salemme, Shields, and Poulos were indicted. You will learn shortly why Grasso was omitted from the indictment. Flemmi and Salemme, having been tipped off that the indictments were coming down skipped town, along with Peter Poulos. Sonny Shields was the only one left to go to trial. Daddieco was the witness against him. Shields was acquitted.

Daddieco was no longer around when Flemmi was available to be tried. Some gangsters say Daddieco had been given money by gangsters to get out of town. He was in the federal witness protection program so the money story makes little sense. What does make sense is that, even though the FBI could have brought him back, the FBI decided not to do it.  The FBI wanted Flemmi on the street to give it information against the Mafia.

I have been unable to figure out what happened to Walter’s Lounge.  Today, an empty lot is all that remains of the criminal haven.  The after-hours joint across the street is also a vacant lot. Maybe no Bennetts were left to take over the businesses.  Maybe, no one in the family wanted to take on that burden and the buildings slowly fell apart.   Three brothers killed in less than a year.  Maybe time to find a new family business.