Murders by Wimpy Bennett’s Roxbury Gang

A key to figuring out unsolved murder is understanding who oversaw the area of the city where the murder took place.  John Martorano wrote that “Roxbury and the South End were controlled by” Wimpy Bennett.

Wimpy proved his tough guy status as a tail gunner on a B-29 during WWII. Martorano called Wimpy “the Fox.”  Martorano said Wimpy spoke with his hand to his mouth so nobody could read his lips. “He was continually looking for an edge.” He said he was “a treacherous old-time Irish thug.” Keep in mind the adjective before thug, it was something that would eventually not be an asset in the world of Patriarca, Angiulo and their Italian paisans.

The murder of Paul Affanato could have been done at Edward “Wimpy” Bennett’s behest. Affanato hung around the South End.  He lived on Colombia Road at the Franklin Park end.  It was not a long jaunt to get to the South End from there.  Columbia Road to the heart of the South End was about three miles distant over two or three different routes. Recall that Affanato lived in a back apartment in a four-story apartment building. It was not a location where you would usually find someone with a big balance in his bank account unless he was holding the money for another.

I eliminated it as a Wimpy hit because Affanato’s connection to Buccelli, his large sum of money in the bank, the word on the street that someone was holding Buccelli’s money and Buccelli’s desperate need for moneyafter his release from jail. Wimpy and Buccelli were both arrested for having in their possession some of the stolen Brink’s money. neither man was involved in the heist. They purchased the money from someone who was involved at a discount.

Wimpy and Buccelli were convicted of the crime of holding the Brink’s money and sentenced: Wimpy to one year and Buccelli to two. When Buccelli was released, he immediately acted on his need for money. A likely source for money would have been Wimpy. Raymond Patriarca did say, according to Martorano, that Wimpy had more money than anyone in Boston other than Jerry Angiulo. Wimpy had moved on from Buccelli and was running his own show for the year that Buccelli sat in the can. Wimpy most likely would have given Buccelli the brush off if Buccelli did approach him.

Martorano noted Wimpy “got along great with [Mafia Boss] Raymond Patriarca.” But, as Martarano was wont to pass on rumors or half-truths when he didn’t know a matter first-hand, Martorano was likely repeating street talk. Even where he was personally involved his stories are full of half-truths. Patriarca, on the intercepted FBI tapes, told Samuel Granito to be careful of “Wimpy” Bennett indicating no great friendship.

Martorano sometimes ventured into telling the truth. He accurately related that Wimpy Bennett “in the late 1950s recruited” Vincent “Jimmy” Flemmi and Steve Flemmi into his gang.  Martorano would have known about the recruitment of Steve Flemmi first-hand. They were close friends and they often hung around together in the Roxbury bars.

No greater wickedness and depravity ever walked the street of Boston that Steve Flemmi. He was born in June 1934. He allegedly joined the Army at age 17 and served in the Korean War. Rumor had it he won the Silver Star and Bronze Star in the Korean conflict but a list of Silver Star winners that is between 70% and 95% accurate does not contain his name. When he was debriefed by the FBI in 2002 and 2003, Steve Flemmi made no mention of receiving any such honors although he suggested he was involved in heavy combat in Korea.

One statement about him that makes sense is “The gangland war turned into a lucrative deal for the three unlikely pals: [Frank] Salemme, [Steve] Flemmi and Joe “the Animal” Barboza, the three most deadly serial killers in the New England History.” Consider this statement as you read about the others in this book.

After leaving the service, Stevie Flemmi hooked up with and began working for Wimpy. His younger brother, Vincent “Jimmy the Bear” Flemmi also joined the crew. Jimmy the Bear would likely have exceeded Steve’s vileness if he did not spend so much of his life in prison, ultimately dying in prison from an overdose in 1979.

Wimpy’s gang consisted of himself and his two brothers, Walter and William, the Flemmi brothers and the guys who would later become the Roxbury gang. The FBI had enrolled Steve Flemmi in its Top Echelon Informer Program. The FBI planned to bring Jimmy Flemmi into the Program even though the FBI had reason to believe the Jimmy had murdered at least a half dozen people at that time and that Jimmy said he wanted to become the number one hit man in New England. The inclusion of murderers like Steve Flemmi in the long running Top Echelon Informer Program has left a black stain on the FBI yet the FBI continues to this day to protect murderers under the Program.

The FBI Intercepted conversations of Raymond Patriarca talking about Jimmy Flemmi. The ELSUR (electronic surveillance) report noted: “Frankie (Salemme) stated that all the people are getting scared of Jimmy and asked Raymond to talk to Jimmy and impress upon him that there should be no more killings in Boston.  Raymond agreed, stating, “if the killings don’t stop, I’ll declare martial law,” but indicated he thought very highly of Jimmy. Patriarca liked Jimmy because he knew that Jimmy would commit any murders that he requested.

But who was Jimmy murdering at the time that had the people scared? The best place to look for the answer is to look at those people who interacted with Wimpy’s gang in the Roxbury and South End areas of Boston that were murdered.  Jimmy may have been involved in Affanato’s murder. He may also have done in Henry Reddington.  One big hint.  If unusual brutality or torture was involved in a murder or if the victim was desecrated, the perpetrator was likely Jimmy.

The Roxbury/South End side of Boston was the hunting ground for Wimpy and his gang. Here, they would have a good idea what people were involved in what criminal activities. Wimpy and his gang wanted a piece of every criminal activity in these areas, especially in the business of bookmaking and illegal drugs.