The Bennett Brothers Murders - Edward, Walter & William

Lara:

Hi all! Today Nina and I are going to be discussing the Bennett brothers: Walter, William and Edward who was best known as Wimpy. Wimpy was the most infamous of the trio. Maybe more memorable because of his nickname than his actions, but nonetheless a duplicitous and complicated character that any author would be proud to claim as their own creation. The mystery of what happened to Wimpy and Walter still haunts the Bennett family to this day.

Nina:

All of the usual suspects were/are linked to their murders. FBI SA H. Paul Rico, Stevie Flemmie, Frankie Salemme and so on. Stevie later testified that Frankie wanted Wimpy killed but that he himself shot Wimpy. Other FBI informants claimed that Wimpy was killed because of Larry Baione. 

Lara:

That makes absolutely ZERO sense! 

And let’s not forget that Larry Baione and Phil Waggenheim supposedly also beat up Stevie!

Nina:

Who didn’t beat up Stevie Flemmi?

Lara:

Everyone and their mother had at some point in time.

Nina:

The man had a face that said “punch me”.

Lara:

The beating is another possible reason why Stevie hated Larry and the LCN guys, but Frankie’s story of being teamed up with Larry still doesn’t make sense.

Then there’s the story that Wimpy was skimming from Stevie and that Peter Poulos told Stevie about it after Stevie accused Peter of skimming.

And before you say anything, NO that doesn’t make any sense either! Read the 302s. No one was going to trust Wimpy Bennett to be their bookkeeper!

Nina:

Can you imagine? The man’s nickname was “the Great Deceiver.”

Also, according to BPD Sargent Walsh’s testimony the bullets that killed William Bennett matched those that killed Peter Poulos.

Lara:

We’ll get more into Poulos’ murder a little later in this episode and at the end of this season.

Frankie would later blame Stevie’s becoming an informant on his relationship with Wimpy. That may have made it easier for him but his brother Jimmy’s foray into top echelon informant land more than likely helped Stevie become a CI himself. 

Indulge me in one of my tirades for a minute. I know that people ask why confess to something you didn’t do, but look at the bullshit story that Frankie told the congressional committee about being dressed as a rabbi along with Stevie! That fucking story has more lives than a bag full of cats. And it was quite elaborate right down to Earl Smith supposedly luring Punchy to the Beth Israel Hospital parking lot.

Nina:

Earl Smith, who was neither Irish nor Italian, but a Russian Jew! Maybe that’s where Frankie got the idea about the Rabbi costumes! 

Lara:

OMG Earl looked just like Boris Nayfeld! You remember Boris. He came over in the ‘70s in the whole Jackson Varnick thing. All tatted up in full vor style.

Nina:

Tax fraud Boris.

Back to Frankie’s rabbi schtick. How many authors, journos, former law enforcement officers, congressmen and ordinary folk have bought that story and regurgutated it like they had been there watching it unfold!

Lara:

I know I’ve ranted about this several times, but read the police reports, read the news articles from when that shooting happened. Punchy was in front of the Beaconsfield Hotel on Beacon St in Washington Sq in Brookline when he was shot. That's roughly 2.5 miles from the Beth Israel Hospital. Punchy was transferred there by ambulance not lured there by Earl Smith. 

Nina:

Howie Winter had an entirely different version of events which at least had the location and events spot on. The point is these men were and are liars. They copped to crimes that weren’t theirs either to build their street cred or cut themselves a better deal. With all those supposedly involved, you would expect someone to know where the bodies of Walter and Wimpy are buried. But instead Stevie sent the Feds on a wild goose chase and the Bennett family had their hopes dashed once again.

Lara:

In June of 2018, Stevie Flemmi took the stand to testify against Frankie Salemme. The prosecutor asked Flemmi to point out Salemme in the courtroom. Guess what? He couldn’t!

Nina:

Do you buy that?

Lara:

Actually I do. Look, if it wasn’t for the Feds and I don’t mean just Rico and Condon, but all the way up to Hoover since they were all aware of what a bunch of fucking degenarate serial killers they were supporting, these guys would have been nothing! The only reason Stevie and Co. came out on top is because they had the full support of the FBI! And when they lost that support, what did they do? They turned on each other and fell apart. Winter Hill was a Fed project going back to Buddy McLean. The only reason the McLaughlins got wiped out was because they wouldn’t cooperate, they weren’t informants or collaborators and that was their undoing. Buddy Mclean - informant. Howie Winter - informant. Stevie Flemmi - informant. I know people like to say Whitey wasn’t technically an informant because he never testified against anyone in court, and that he wasn’t aware that the Feds assigned him a number. I do NOT agree. I think Whitey had a number going back to 1965 when he came home from Alcatraz. 

Nina:

You’re not going to get an argument from me.

Lara:

I swear telling people that these guys were all cut from the same cloth is like telling a kid that Santa Claus isn’t real. They know it, but want to hang onto the fantasy that these were stand up guys.

Enough of my ranting. We’ll get back to the testimony of Stevie Flemmi towards the end of the episode. 

Nina:

I bet most of our listeners don’t know where the story that Frankie Salemme murdered Walter Bennett came from. Decades later in the 1980s, Larry Baione claimed that Walter Bennett had hired Frankie to take out Larry. But while they were waiting for Larry to appear, Frankie shot and killed Walter instead. 

Another story that makes no sense! But that’s what Larry told Jerry Angiulo on the infamous wiretaps in the 1980s.

Lara:

Is that the cardboard box in the back of the beachwagon story?

Nina:

Yes!

Lara:

Gossiping old bitties!

Nina:

Who us?

Lara:

No, the wise guys!

Ok, let’s briefly talk about the early lives of the Bennett brothers, their activities and how the three men found themselves murder victims within a year of each other.

Nina:

William Frederick Jr. was born on May 29, 1911, Walter Earl on August 17, 1912 and Edward Albert “Wimpy” on January 1, 1919 in Boston to William Frederick Sr. and Flora Caroline Seymour. 

Lara:

Often the Bennetts were described as Irish gangsters which isn’t quite accurate. 

Nina:

Not the gangster part, the Irish part. They were roughly a quarter Irish from the Bennett line. 

Lara:

Our Bennett cousins were descendants of William Brewster! Pilgrims!

Nina:

They were also Loyalists, which is how part of the family ended up in Canada for a few generations.

Lara:

We won’t hold that against them! 

Nina:

I was more implying that they were government collaborators for generations.

Lara:

So their cooperation came naturally to them.

There doesn’t seem to be anything so out of the ordinary about their childhood. The only odd thing is that 11 year old Wimpy was nowhere to be found in the 1930 census.

Nina:

It was hard enough finding the census! And part of the family got counted twice. 

Lara:

I know, you just found it. But no sign of Wimpy. Maybe he was in juvie, but there’s no mention of him having a juvenile record on his rap sheet.

Nina:

Moving on. Both Walter and Wimpy enlisted in the Army at the beginning of WWII. One of our listeners who is a grand nephew of the Bennetts sent us a pic of a postcard from Walter from 1943.

Lara:

Thank goodness for our listeners sharing with us. Wimpy enlisted in the Army on December 17, 1941 and served as a private in the Air Corps as did Walter. On July 29, 1942 Wimpy married Frances Weresko in Michigan. Before the end of his time in the service Wimpy was awarded the Distinguished Flying Cross.

Nina, who was the first to find themselves in trouble with the law?

Nina:

Walter, the boy bootlegger! In August of 1931 he and Joseph Lewis were arrested in a basement at 335 Shawmut Ave for selling alcohol. Walter was just 17 at the time. His father had passed away the previous summer.

In 1949, Wimpy along with three other local guys, found himself in a jail in Maine after fleeing from the scene of a robbery they committed at Steuben’s Restaurant in Boston. But a rural jail wasn’t going to hold Wimpy. He cut a hole in the roof and off he went.

Lara:

In 1952, Wimpy was held on contempt charges after refusing to cooperate with prosecutors in the Brink’s investigation.

That investigation would last for half a decade and spawn many other investigations including one into illegal lottery operations in and around the Boston area. In 1954, Walter Bennett was accused of funding one such operation along with Anthony Pino and Vincent Costa of Brink’s Heist fame. Forced to take the stand in front of the Massachusetts Crime Commission, Walter refused to state his present occupation but admitted that he’d been running what he called “a little dice game” in Attleboro in 1949. He also accused the commission of “asking silly questions”. 

Nina:

“I just went to school for 7 years and can’t match wits with college graduates.” he added.

Lara:

That was one of dad’s lines, but he’d say 4th grade.

Nina:

The Brink’s heist would continue to haunt Wimpy Bennett for years. If you want to hear more about that case listen to episode 7. Wimpy and Fats Buccelli were sentenced to one year in Deer Island for possession of part of the Brink’s loot, but in May of 1957 Fats and Wimpy were cleared of being accessories after the fact. Buccelli was killed on June 19, 1958.

Lara:

Besides their criminal activities, Walter had his lounge, Wimpy, his variety of businesses ranging from a smoke shop, construction and smut peddling. William kept a lower profile.

Nina:

Does Wimpy’s boosting count as a profession?

Lara:

More like a hobby or in his case a condition since he appeared to be a klepto.

A crazy Wimpy story. In January of 1960 a man named Charles Kirby received a phone call at his TV repair shop by a man looking for Wimpy. The headline read that there was a tip that a hit had been ordered on Wimpy.

Nina:

As if there was a shortage of people who loathed Wimpy and wanted him dead!

Two years after Wimpy went missing the Boston Globe ran an article describing Wimpy’s Machiavelian behavior and blamed him for having a role in at least 50 of the gangland murders of the 1960s saying that he manipulated people and instigated the hits in an effort to clear out the competition. 

This was essentially a rehash of the Jerome Sullivan article from 1965 that we mentioned in the Hit Parade of 1965.

Lara:

Like you said no shortage of people that loathed Wimpy.

Nina:

It’s worth noting again that the Bennetts were paying off at least one cop, but likely more. Wimpy had a particularly close relationship with Detective Billy Stuart of the BPD, and was regularly informing to him. We’ve covered a lot of Wimpy’s activities in other episodes, so we won’t go into all of it again. We’ll link to them in the shownotes.

Lara:

And Walter also loved running his mouth to the authorities. He received frequent visits from the postal inspectors throughout the five year investigation of the Plymouth Mail Robbery.

In 1963 the Postals concluded that while Walter Bennett had not been that helpful “... he was a valuable pipeline and further contact should be maintained to nurture this cooperation.”

Nina:

Three years later, Walter was still talking to the Postals. “As usual, he was congenial and cooperative. His first remark was “Well what do you want to know about Diaferio?” Referring to Sonny.

Walter was still convinced that Punchy McLaughlin was involved in the Mail Robbery. He told the agents that until Punchy was murdered he had been “shaking down Sonny regularly… not that he had something on him, but just putting fear into Sonny that something would happen to him.”

Walter continued on that Sonny was getting a lot of people in the middle with his stories of where his wealth came from such as gambling and borrowing from shylocks, and admitted to lending Sonny a couple of thousand dollars himself. Walter ended his statement: “You guys are on the right track.”

Lara:

In October of 1966, citrus Baron Charles Von Maxcy was attacked in the bedroom of his Florida home. An intruder threw a sheet over his head, stabbed him four times, shot him once in the head and then fled from the 324-acre estate. There were no fingerprints or weapons found at the scene, but a couple of months later Von Maxcy’s widow Irene came forward to say that her lover Johnny Sweet arranged for the murder of her husband. Sweet was an associate of Walter Bennett’s and a frequent visitor of Walter’s Lounge on Dudley St. near Uphams Corner in Dorchester.

Nina:

Irene was given immunity when she testified in 1967 against Sweet who she claimed convinced her that if they murdered her husband they would share his fortune of $2 million. 

Sweet's first trial ended in a hung jury. He was convicted in a second trial and sentenced to life. An appeals-court judge later overturned the conviction on a technicality. By then, the state's star witness, Irene, had been prosecuted for perjury. Florida law won't let a person convicted of perjury testify at a criminal trial. So Sweet was freed.

A man named William Kelley did not come into the picture until 1984, when Sweet made a plea-bargain deal to testify against Kelley for being one of his hit men. Sweet claimed he paid $30,000 to William Kelley and Andrew Von Etter, to murder Maxcy. Von Etter of Mattapan had been found shot and beaten to death in the trunk of his car in Medford on February 1, 1967.

Lara:

You left out that Von Etter was supposedly a noble of German descent born in Lithuania who somehow found himself wrapped up with the Bennetts and Earl Smith. He was out on bail at the time of his murder after being indicted with Earl back in November of ‘66.

Back to the Von Maxcy case. Poor Kelley was convicted in 1984 and placed on death row all the while maintaining his innocence. In 2002 the son of Steve Busias, a cousin of Billie Aggie, came forward during Kelley’s appeal to say that he believed his late father was responsible for the murder of Von Maxcy. Kelley is still on death row.

Nina:

Back to the Bennetts and their murders. Wimpy was looking for Det. Billy Stuart on the 18th of January 1967, but Stuart didn’t have time to meet him. The following day Wimpy met with a friend at 10:00 am and was supposed to sign a company payroll after that, but never showed up. On January 28 the Boston Globe ran an article about Wimpy’s disappearance. But his son didn’t report him officially missing until March.

On August 4, Wimpy’s car was found after three boys were arrested while breaking into a grocery store in Allston. One of the boys said his boss named Steve gave him permission to use the car. Was “Steve” supposed to be Stevie Flemmi?

Lara:

That’s what I assumed. 

On April 10th, Walter’s wife, Barbara, reported him missing to the police. She had last seen him at 10:30pm the previous Tuesday. Four days later, informant number BS-922-C stated that Stevie Flemmi and Frank Salemme had taken out Walter and Wimpy Bennett. Informant added that they did this to pacify the LCN since there could not be any peace with Wimpy feuding with Larry Baione. The informant stated that Flemmi and Salemme were really moving and are going to be big with the organization.

Nina:

Which organization, the FBI?

Lara:

Hey, he didn’t specify!

Salemme’s version of events was that Walter blamed Stevie and the LCN for Wimpy’s murder and was out for revenge. They lured Walter to Frankie’s garage on the premise that Frankie would help him take Stevie out. But instead Stevie was waiting for Walter and killed him there as he was walking up the stairs. Stevie then disposed of Walter’s body. 

Walter’s car was eventually found in a parking lot at Logan Airport. 

Nina:

Walter left behind an estate of roughly $150,000.

On December 23rd, William Bennett was murdered. His crumpled body was found in a  snowbank on Harvard St. near Blue Hill Ave. with a bullet through his brain. 

Just like in the death of Walter Bennett, Salemme claimed that William Bennett was looking for revenge for his brothers. Hugh Shields and Dickie Grasso went to Stevie Flemmi and they concocted a plan to take out Billy Bennett. Supposedly their plan was to kill him and then dump the body with Walter and Wimpy in Hopkinton. Stevie and Frankie allegedly were to follow in a second car to pick up the body. But since Stevie Flemmi was involved, the whole thing went terribly wrong. Billy was shot four times in the chest. The force of impact caused the car door to open, and Billy’s dead body fell out of the car and into the middle of the street in Dorchester. A taxi driver who was passing found Billy, and the assailants couldn’t retrieve the body.

Lara:

Poor Dickie Grasso's abandoned Buick sedan was found in Brookline a week later. The cops found Dickie’s corpse face up in the trunk after they’d towed it to the police garage. You know Dickie wasn’t packing a full deck.

Nina:

No question about that. 

As we’ve recounted in numerous episodes already, the following month, Flemmi allegedly planted a car bomb in attorney John Fitzgerald’s car.

Stevie Flemmi allegedly told Rico about his involvement in Wimpy’s murder. Rico subsequently filed a false report, stating that Flemmi told him that others were responsible for the murder. 

Just a few days after Billy Bennett was murdered, Rico went to his home looking for documents pertaining to the activities of Wimpy and Walter, but not for the FBI, but rather to assist Stevie. William Bennett’s family would later sue the Feds alleging that “Rico assisted and participated in the death of William Bennett in order to strengthen Flemmi's position in his criminal operations, thus assuring the continuing flow of information regarding the LCN to the FBI, by way of Flemmi's underworld connections.” 

Rico was unsuccessful, but Stevie took over the Bennett’s illegal enterprises anyway.

Lara:

In September of ‘69, Frankie Salemme supposedly received an early morning phone call from Stevie Flemmi. Frankie picked up Stevie and they drove to Revere Beach to meet Rico who had another FBI agent with him. The second agent stood to the side and wasn’t involved in the conversation the other three men were having. Frankie’s description of the second Fed could only be Gerard Comen, dad’s handler and Rico’s partner at that time. 

Rico warned Stevie and Frankie that there were indictments coming down in the murder of Billy Bennett. He told them to get out of town and they obeyed.

The men took Peter Poulos with them but according to Frankie’s version of events, he left them in California and went back east to New York City and wasn’t present when Stevie murdered Peter Poulos in the Nevada desert.

Nina:

The indictments came down on September 11. Five men were named: Hugh Shields, Frank Salemme, Stevie Flemmi, Peter Poulos, and Robert Daddieco.

Hugh Shields had a record that dated back to the time he was in juvie. In 1953 he escaped with two other boys from Shirley. They stole a car and made their way to Albany, NY where they led the State Police in a high speed chase. After the cop shot at their car three times, they abandoned the car and took off on foot. They tried to hide in a basement of a local house, but were cornered and sent back to Shirley.

Three years later, Hugh was charged with arson in the 1955 Deer Island prison riot and sentenced to two years in East Cambridge jail.

Lara:

Just like in the other trials of the 1950s and 1960s in Boston, the Feds relied on a single witness to make their case for them. This time their trump card was Robert Daddieco. Robert was a small-time hoodlum who had been arrested in June 1969 after he and three accomplices from Canada tried to rob a bank in Somerville. They pistol whipped the guard and forced the bank manager and customers to the floor. But then the police arrived on the scene and the four men were forced to surrender at gunpoint. A fifth accomplice shot another cop and fled the scene. A couple of weeks later Robert was indicted on charges of armed robbery while masked and assault with intent to commit murder.

While Robert was sitting in Walpole awaiting trial, SA Rico pressured him into becoming the star witness in the Billy Bennett murder case. Robert was given a Confidential Informant number and made a Top Echelon informant in August. He eventually joined Joe Barboza and Vinnie Teresa in the newly created Witness Protection Program.

Nina:

The criminals weren’t the only ones in trouble. Det. Billy Stuart was indicted in February of 1970 for being an accessory after the fact in Billy Bennett’s murder. That same day he was “relieved of his duty” as a cop. He’d been with the BPD for 19 years. He pleaded innocent to the charges two days later and a trial date was set for April 7.

One of the charges against Billy Stuart was that he’d participated in moving the car that had Dickie Grasso’s body in it from Dorchester to Brookline.

At Stuart’s trial, an alleged associate of the Bennetts testified that they were paying Billy Stuart $50 a week, but the dates he gave were after both Walter and Wimpy had already disappeared. There was also a monthly payment envelope that had the initials BM on it.

Lara:

At the trial of Hugh Shields in April 1970, Daddieco testified that there were six men involved in the plot to kill Billy Bennett. Dickie Grasso and the five men who had been indicted back in September 1969. 

Robert claimed that Dickie Grasso was Billy Bennett’s bodyguard and therefore was “the only man who could get close to him”. Hugh Shields was the trigger man. But Billy saw the gun, and tried to escape from the car and that’s why he fell out into the snowbank. Stevie Flemmi and Frankie were in a second car in order to retrieve Billy’s dead body, but the passing cabbie put an end to that plan. In typical Flemmi fashion, Stevie called up Billy Stuart to save him. And as usual, Stuart came running. He drove them back to the murder scene and helped them move the car to Brookline with Grasso’s body in it.

A similar version of the story that we quoted earlier from Frankie.

Oh remember at Raymond Patriarca’s trial in 1970 when Jack Kelley was testifying against Raymond. Raymond screamed “ask him where Wimpy Bennett is, he was the last one to see him alive!”

Nina:

Raymond was pissed but Jack didn’t bat an eyelash.

In the meantime back in Boston, Billy Stuart denied that he was involved in the murder, and claimed that he’d been shocked to hear that Billy Bennett had been murdered. He did concede however that the Bennetts had all been his informants. But he stated that he had never revealed his sources even to his bosses. “Even the FBI does not reveal the names of informers.”

Hugh Shields and Billy Stuart were acquitted on April 30th. Shields was sent back to Walpole on a parole violation charge. But Billy Stuart was free to go. In an interview with the press, he lambasted the prosecution and alleged that the investigation into Billy Bennett’s murder had been sloppy because Daddieco had turned prosecution witness so quickly after the indictments. 

In 1974, Stevie Flemmi returned to Boston and the Bennett murder charge (among others) was dropped, just as the same charge against Frankie Salemme had earlier been dropped. The pair were indicted again in 1996. 

Lara:

In October of 2001 former FBI SA Dennis Condon testified: ‘‘It’s also my understanding that Daddeico positively refused to testify against Flemmi, supposedly because he had a dislike for Salemme that he did not have for Flemmi, and refused to testify.”

Included in that document was the following statement:

“It is worth noting that law enforcement did not pressure Daddeico to testify against Flemmi, and it appears that it was acceptable to law enforcement to allow the witness to testify against one defendant and refrain from testifying against another defendant based on personal friendship.

If Flemmi had been prosecuted in 1969 for the Fitzgerald bombing or the William Bennett murder, his role as an FBI informant might have been disclosed, and its legal implications might have been examined, three decades ago. Flemmi’s successful flight to avoid prosecution spared Rico, and the FBI the risk of the embarrassment and controversy that disclosure of Flemmi’s dual status as an FBI informant and an alleged murderer has recently entailed. Rico had reason to be concerned about embarrassment to the FBI. . . . By honoring his promise to protect Flemmi, Rico also promoted the possibility that Flemmi would in the future again become a valuable FBI informant.”

Nina:

In November of 2001, authorities were digging at a firing range in Hopkinton looking for the remains of Walter and Wimpy after Salemme told them the location claiming he helped bury the Bennett brothers hoping to shave time off of his sentence.

Lara:

Oh and don’t forget Vinnie Teresa claimed they were dumped in lye on a construction site somewhere along rte 93! I mean it’s only 190 miles long!

The Bennett family has yet to receive any closure. Decades back former SA and convicted felon John Connolly tried to convince one of the Bennett descendants that the Angiulos had killed the three brothers. But they knew better.

Fast forward to June of 2018, as we mentioned at the beginning of this episode Stevie was on the stand and asked to ID Frankie in the courtroom and he couldn’t. Frankie leaned into his attorney and told him that Stevie was soft, while motioning with his tongue in his cheek that he had a stroke.

Nina:

The Bennett family still has no answers. Stevie and Frankie are sitting in prison, and either can’t remember or don’t know the answer. Were the Feds involved in the disposal of their bodies? Or was someone else responsible for their demise? Was there some weight to Raymond Patriarca’s accusation against Jack Kelley? We’ve alluded to this many times but there were four missing persons cases in the 60s: Billy Aggie, Tommy Richards and the Bennett brothers and what did they all have in common?

Lara:

Jack Kelley. But we will probably never know the truth. Speaking of Jack, next week we’re going to be talking about the botched heists of the late 1960s. 

Nina:

Jack never botched anything!

Lara:

No, but the Feds had a laundry list of names that included Jack and dad that they were looking at for just about every armed robbery in those days.

Nina:

I swear they’re still using the same list since some of the men we’ll be looking at are current potential Gardner Museum Heist suspects: James Marks, Richard Megna and a few others.

Lara:

Hope you join us again. Thanks for listening!

Nina & Lara:

BYE!!!!