The Boys of Winter Hill

Lara:

Welcome Back, everyone! Today we’re revisiting Winter Hill, but unlike in previous episodes we won’t be focusing on Buddy McLean. We’ll be looking at Buddy’s murder in episode 33.  Instead today, we’ll be discussing the men who were not just part of his crew, but also those who would take the reins after Buddy was killed in 1965, and were allied with him prior to that. For our listeners who aren’t from the Boston area, Winter Hill is located in Somerville. The Winter Hill Gang was named for its neighborhood, not for Buddy’s heir, Howie Winter.

Although the group became organized in 1955, it was not called the Winter Hill Gang until sometime in the 1970s while Howie was still the leader. The label begins to appear in FBI 302s before Howie’s race track case became public. Many of our listeners will be familiar with Winter Hill because of Whitey Bulger, but in the 1960s under Buddy’s leadership they were famous for the bloody gang war that raged between them and the McLaughlin Gang of Charlestown that took dozens of lives on both sides.

Nina:

Just for clarification, Howie’s last name was Winter not Winters. In our research for this episode we often came across his surname in the plural. Another note about Howie, he was not half Italian. We’ll talk about Howie’s ancestry when we profile him a little later in the episode. Jimmy and Stevie Flemmi have been covered briefly in other episodes, but today we will dive deeper into their backgrounds and crimes as well as Johnny Martorano and Frank Salemme.

Lara:

To include a bit of history, we’ll give more information about Joe “Mac” McDonald, Buddy’s mentor, than we did in episode 13. Whitey Bulger, Howie’s heir to Winter Hill, will have his own episode in the middle of season 2. Today we’ll focus on the ‘60s, but we'll also talk about the ‘50s and a bit about what the future would hold for some of the gang members. In season 2 we’ll be dedicating many episodes to Winter Hills activities in the ‘70s and ‘80s. Since Joe McDonald was who many considered the founding father, let's start with his story.

Nina:

Joseph McDonald was born in Massachusetts on July 14, 1917 to Matthew and Margaret McDonald. His parents immigrated to the Somerville area from Nova Scotia before Joe was born. He was one of 8 children. There’s no shortage of folklore about Joe Mac including having once been arrested in a New York City train station while dressed as a nun and toting a machine gun in a hockey bag.

Lara:

Legend also has it that he dressed in drag to attend a family member’s wake while on the lam.

Joe was also a WWII vet having enlisted at the beginning of the war with one of his younger brothers. Both served in the Navy. The ship they were serving on was sunk by the Japanese on August 9, 1942. Joe was wounded, but helped rescue others and would later receive an accommodation. His brother did not survive the attack. Upon returning home, he started drinking heavily, but desiring to dry out he headed to the local YMCA where fate would have it he met Buddy McLean who as we’ve mentioned before was a fitness fanatic. 

Nina:

Besides being a WW2 veteran he was known as a bookie, loan shark, thief and killer with a drinking habit. Joe was also a big boxing fan. Bank robbery was said to be his crime of preference. Unlike many of the other men we’ve profiled, he had a reputation of being a good planner. But his luck ran out on January 16, 1960 when he and his brother Leo robbed the Sunburst Dairy Farm in Stoneham. Their haul was $36,000. Leo received a 20 year sentence but on appeal it was increased to 30 years. Joe was sentenced to 12 to 18 years. During his appeal the judge said he would have received a sentence reduction if he identified the third man in the heist, but Joe refused.

Lara:

But that wasn’t going to keep Joe off the street. On November 6th, 1963, the father of four fled from the Forestry Camp in Plymouth. I won’t call it an escape as there was no wall to scale or bars to saw through. While on the run he was said to have threatened the witness who put him away. He would remain on the lam until July 23rd, 1966 when he was finally captured after a chase and shootout with Boston Police in Brighton. In addition to the escape charge he was facing attempted murder charges. Off Joe went to Charles St. Jail. In October of that year Joe was found guilty of three charges, two counts of assault and battery and illegal possession of a weapon, and sentenced to an additional 8 to 10 years. By the time Joe was released from prison Howie Winter had become the leader of the Winter Hill Gang, but that wouldn’t be the end of his criminal career. We’ll be covering what Joe was up to after his return to Winter Hill in season 2. To give you a hint about whether or not he went straight, Joe passed away in prison awaiting trial along with Johnny Martorano and FBI SA H. Paul Rico for the murder of Roger Wheeler. When Jimmy Martorano was asked about Joe years later he said, “Who do you think was doing all the killings for Winter Hill? It was Joe.”

Nina:

I don’t know how that can possibly be true because most of the Winter Hill murders and murderers are accounted for. And not one of them was done by Joe Mac.

Lara:

Unless Johnny Martorano, Stevie Flemmi and Frankie Salemme are all liars!

Nina: 

They all claim to have killed the same people.

On that note let’s move onto Howie Winter. Howard Winter was born in Boston, Massachusetts on March 17, 1929 to William Winter and Helen Corkhill. He was the youngest of 4 boys. English and Irish on his mother’s side. Irish and German on his father’s side. In the early 40s the family relocated to Somerville from West Roxbury. He and Buddy met the first day the family moved in. Howie was a year older than Buddy, but Buddy was definitely the leader of the pack. Buddy was the brawler and Howie was the peacemaker. During WW2 he enlisted in the Marines. Upon his return to the neighborhood, Howie fell back in with his buddies and began working the docks with Buddy, Joe Mac and Tommy Ballou.

In 1958 Howie was arrested after being found in a bar breaking into cigarette vending machines. 

In December of 1959 he was arrested on gambling charges along with Bobo Petricone and 26 others in a huge raid by the Staties. All of them were indicted on those charges in January of 1960, but nothing seems to have come of the case.

Howie was Buddy’s right hand man and also rumored to have killed Punchy McLaughlin. 

Lara:

Who wasn’t rumored to have killed Punchy?!? And how many people took credit for it?

Nina:

Howie Winter did not kill Punchy McLaughlin! Everyone and their mother claimed they killed Punchy except for the guy who probably did do it. It was a get out of jail free card and who was going to come after them after they’d wiped out the McLaughlins?

Lara:

Who was left? Just Georgie rotting in jail!

Nina:

On September 4th 1962 Bobo Petricone’s wife borrowed Howie’s car to run errands in Somerville. While she was backing into a parking space, an explosion occurred. No one was injured, but the police stated that the type of bomb that was planted was identical to the one planted on Buddy’s car back in ‘61. The police believed that the intended victim was Howie rather than Mrs. Petricone. That morning Howie had driven the car to her house, so she could go to the bakery. No one was ever charged.

Lara:

So here’s the weird thing about that. It’s always been assumed that it was the McLaughlins who tried to take out Howie, but there was another theory that it was Stevie Flemmi. If that’s true then there’s the possibility that Stevie tried to take out Buddy. Was there a power struggle going on even that far back?

Nina:

Well, that is a possibility, but my question is who was rigging the explosives for him?

Lara:

The one possibility I can think of off the top of my head would be Joe Puzzangara. But so many of these guys had military experience including Stevie Flemmi and Georgie Mclaughlin, so we’ll never know the real story.

Speaking of Stevie, let’s move on from Howie and talk about the Flemmi brothers.

Nina:

Stephen Joseph Flemmi was born on June 9, 1934 and Vincent “Jimmy” “The Bear” Flemmi was born on September 5, 1935 to Giovanni Flemmi and Mary Irene Misserville. Irish twins! They had another brother, Michael, who would go on to become a cop. More on him in a little while.

Jimmy’s record dated back to 1949 when he was still a juvie. On a different path, Stevie enlisted in the Army in 1951 at the age of 17 and served two tours of duty in Korea with the 187th Airborne Regimental Combat Team. He was awarded the Silver Star and Bronze Star for valor, and honorably discharged in 1955. 

Back home, his brother Jimmy was sentenced in 1953 to 18 months in the House of Correction on robbery charges. In December 1954, Jimmy, Rocco and Salvatore Balliro, and another man were convicted of assaulting two Navy officers. Jimmy was sentenced to two and a half years in the Dedham House of Correction. In addition he was given a two year suspended sentence to begin after his jail term, and placed on probation for five years. But he didn’t serve the full term.

In April 1956, the youngest Flemmi, Michael, fell 45 feet from the roof of a Roxbury house. Michael was on leave from Shaw Air Force base, and he claimed that he was looking for a prowler who was stalking a woman living in the building. But I think he was a peeping tom! Either way, he fractured both knees and ended up in the hospital. 

Lara:

He was probably the stalker! Considering who his two brothers were that would not surprise me!

At 7:35 on the morning of December 19, 1956 Jimmy and Salvatore Mesiti forced an official at the Boston and Albany Employees Credit Union to open the safe of his second floor office at South Station. They strapped the 68 year old treasurer of the Credit Union to a chair with adhesive tape and taped his mouth before fleeing with $15,000. They also grabbed the wallet off of a porter in the building. 

Warrants for their arrest were issued the following day, and on the 24th, Jimmy was arrested and held on $5000 bail.

The following month, Salvatore Mesiti was also arrested for that robbery. If you listened to episode 8, you might recall that Mesiti was convicted along with dad in the Desisto home invasion. In February Mesiti was cleared of the bank robbery charges, a crime which he probably did commit. Jimmy and another man named Robert Boucher were indicted.

Jimmy was released on bail and went on the lam. So much for the five years probation.

Nina: 

The FBI finally caught up with Jimmy in Saugus in July 1957. But while Jimmy had been on the lam, he’d also forged and cashed nearly $100 in checks in a Roxbury food market. The following day, Jimmy was back at court in Roxbury. He was being sent back to jail to wait for a Grand Jury decision on the check forging charge when he attempted to escape from custody at the Roxbury Courthouse. In the corridor outside the second floor courtroom, he knocked down a court officer and dashed downstairs. He fled down Roxbury Street and through several alleys before another court officer caught up with him two blocks away near Vernon Street. Jimmy kicked and punched the clerk, knocking him down, and shattering his glasses. But the clerk held on until the cops arrived at the scene. 

Lara:

In the meantime, Jimmy’s brother, Stevie, was also getting into trouble with the law. On October 4, 1957, Stevie was arrested just moments after attempting a payroll holdup in Roxbury. A stakeout of 25 plainclothes police officers were waiting for him and his accomplice. They’d been warned ahead of time that someone was going to rob a market in the neighborhood. But they weren’t sure which one. 

While the police were watching a supermarket, a wallpaper company salesman was walking down the street carrying a payroll of $4000 in a brown paper bag. When he passed a man leaning against a wall, the loiterer jumped him from behind and grabbed his throat. A second man stepped over menacingly. The salesman dropped the bag on the street. The first man bent to retrieve the fallen money and the salesman grabbed him by the waist. 

“Don’t be crazy,” snarled the man looking at the salesman. The victim released his attacker who turned and fled into the market. 

Nina:

The police officers took up pursuit with guns drawn. A detective cornered the first man in the rear parking lot. The second assailant ran in the Dearborn street housing project where he was captured. 

Stevie and his accomplice allegedly admitted to the holdup and implicated a third man. Stevie told the cops that he had been following the salesman for three weeks and was completely familiar with the man's weekly payroll routine. The third man was supposed to pull off the actual job but he bailed on them at the last minute and didn’t show up. Instead of bailing out themselves, Stevie and his accomplice decided to go ahead with the plan. 

Lara:

Years later Frankie Salemme told John Durham that “Stevie wasn't a planner. He would go if you took him by the hand, but he wasn't a planner at all. He had his own agenda, and he wasn't deviating from that.”

Obviously Frankie had a good reason to have a grudge against Stevie. Stevie set him up to go to the can for two decades for the Fitzgerald car bombing. Something that I still do not believe that Frankie was involved in at all. 

Stevie was arraigned on October 6, and the case was continued to October 18, but it doesn’t appear that anything happened after that.

Nina:

On October 12th, Jimmy Flemmi was sentenced to 10 years at Walpole State Prison for the Credit Union robbery. Three days later, Salvatore Mesiti was found unconscious in a prison corridor and rushed to the hospital at Norfolk Prison Colony. Initially, the authorities reported that he had been stabbed in the stomach with a bread knife by an unknown assailant. Of course there were no known witnesses even though the attack had taken place at 10 in the morning and there were 94 guards on duty at the time. 

The prison officials said they suspected that Mesiti was attacked “for revenge”. “...he was first knocked unconscious, after which he was stabbed several times with a homemade knife in the chest and face.” 

At first the authorities thought that he was also set on fire after being stabbed. But it turned out that a liquid containing some kind of acid had been thrown on Mesiti, disfiguring and blinding him for life. 

Lara:

The authorities alleged that he’d been attacked by three men: James Parker, Russell Halliday, and William Cavanaugh. If you’ve been listening in you might remember that Cavanaugh was Sonny Diaferio’s partner in the pepper theft and was convicted of aiding Elmer Trigger Burke’s escape from Charles St. And Russell Halliday’s story was featured in our Thanksgiving Bonus Episode along with Frank Martin feeney.

 The inmates raised $600 for the defense counsel of the three. The defense attorney was Joseph Sax who stated, “There isn’t a man in the prison who doesn’t know who really committed the attack.”

All three defendants were acquitted in December of 1957. 

Nina: 

Jimmy was one of the 23 men who were voted out of Walpole and transferred to Concord in January 1958. 

Lara:

Don't forget Billie Aggie was also in that bunch!

Nina:

But Jimmy was back at Walpole just a few months later. 

In April 1958, Robert Boucher, who had been convicted with Jimmy of the bank robbery, was beaten at Walpole. He was taken to Norfolk Prison Colony where he was treated for head injuries and a possible skull fracture. The authorities alleged that another inmate named John Daley had attacked Boucher with a club. But Daley had also been knifed in the forehead, the back of the head and the mouth in the fight, and was given nine stitches. Daley did have a history of fighting with other inmates, so I’m not discounting it entirely, but it’s awfully suspicious to me. 

Lara: 

In November that same year, Jimmy attacked a prison guard at Walpole while he and several other prisoners, including William Cavanaugh, tried to escape. Jimmy was placed in segregation and a complaint was issued at Dedham Court.

In June of 1961, Jimmy was charged with stabbing to death of a fellow inmate, 30 year old Raymond Gabriel, only to be acquitted in March of 1962.

Nina:

Not long after, Jimmy was back on the street. He hadn’t even served his full sentence. And there’s no way he accrued “good time” given his behavior while he was in prison. I think he made a deal with the Feds in exchange for early release. Jimmy’s CI number indicates that he was on the FBI books by late 1963 or early 1964. And the prison probably couldn’t wait to get rid of him. The man belonged in a mental institution, not a prison. But instead the authorities let him loose on the general population and made him an informant! 

Jimmy’s FBI handler was none other than SA H. Paul Rico.

Lara:

1951. Paul Rico applied to be an FBI agent in the wake of the Brink’s Heist, and finished his training in April of 1951. His father’s illness made it possible for Rico to be transferred to the Boston office in March of 1952 after he submitted a hardship request. 

Rico and his partner SA Herbert Briick proved themselves to Hoover as capable agents after they arrested Whitey Bulger in a bar in Revere in March of ‘56. The story goes that Rico already knew Whitey from his days hustling in local gay bars where Rico supposedly went to recruit informants. Whitey had been on the lam after a bank robbery spree in Massachusetts, Rhode Island, and Indiana. And Rico was a member of the Boston FBI Office’s Bank Robbery Squad. Rico received a promotion as a result of his successful apprehension of Bulger. In addition to this achievement, Whitey convinced his accomplice, Richard Barchard’s wife, Dorothy Barchard, to become a Confidential Informant for the FBI, a role she played well into the late 1960s if not beyond.

Rico first tried to recruit dad when he was locked up in Charles Street jail in 1957. At that point in dad’s life it was unthinkable to him that he would turn on his friend. Dad instantly hated Rico and the feeling was mutual, but less than five years later, Rico and dad would once again be face to face, but this time dad had too much to lose. With a trunk full of machine guns and a life sentence the only future in front of him, he agreed to become an informant, but he wasn’t about to play by Rico’s rules. 

By 1964 Rico was still working the robbery squad and juggling multiple CIs, not just dad. His band of merry and not so merry bandits included: Dorothy Barchard, Buddy McLean, George Ashe, Jimmy Flemmi and his brother Stevie, to name a few. 

Nina:

On May 4th Francis Benjamin’s headless body was discovered in the trunk of a stolen car that had been abandoned in Old Harbor Village in South Boston. He had served 5 years for armed robbery at Walpole, and only been released just two weeks earlier. The medical examiner believed that he had been shot in the head before being beheaded.

The FBI alleged that Jimmy Flemmi shot Benjamin with a revolver that was stolen from a policeman, and cut off his head so a ballistic match couldn’t be made. Which, frankly, sounds exactly like something a Flemmi would do. 

Lara:

I tend to believe that it was Jimmy who killed him. The two of them had been in the can together. Who knows what kind of a beef they had with each other, or maybe it was over drugs. 

The Boston FBI office advised J Edgar Hoover in a letter dated June 4, 1964, that Jimmy Flemmi was a suspect in a number of gangland murders and had told an informant he planned to be the number one hitman in the area. But the Feds continued to use him.

The immunity these guys enjoyed spilled over into local law enforcement. Frank Salemme told a story that one time, Jimmy Flemmi shot a guy in the South End. The cops watched him do it. Jimmy got out of the car and left the scene of the crime. The cops took the car and pushed it out of their division so they wouldn't have to investigate. Then the cops went to Stevie Flemmi and got $2500 off of him to keep quiet.

Nina: 

You realize that the “informant” who told the Feds that Jimmy wanted to be the number one hitman was Jimmy! 

Lara:

He said it was easier than robbing banks! As we know he wasn’t so successful in his bank robbing endeavors.

Nina:

He didn’t have the IQ for that! Besides, he was always high!

Back to 1964. Throughout the summer, 302s from the Boston office were full of reports about Jimmy, including that Jimmy had cut off Francis Benjamin’s head, and threatened to kill Teddy Deegan, but the Feds continued to rely on him as a source.

On September 2nd that same year Leo “Iggy” Lowry’s badly beaten body was discovered near the edge of Cross Street, off Route 139 in North Pembroke. His throat had been slashed, but his cause of death was a bullet fired into the back of his head. He had last been seen alive leaving a bar in the South End of Boston between 1:30 and 2:00 on the morning of August 31st. The police said they believed that Lowry was killed at a different location and his body dumped in North Pembroke. 

Lara:

Lowry had a long record with convictions for breaking and entering, larceny, and two escape attempts: once from Deer Island in 1951, and another from Charles Street Jail in Boston in 1952.  The main suspect in Lowry’s murder was Jimmy Flemmi. According to Casey Sherman’s book “Animal”, Lowry was bisexual and had been prostituting himself while he was in Charlestown State Prison. But upon Lowry’s release he fell for the wife of a gangster who was in the same circle as Joe Barboza and Jimmy Flemmi. The unnamed gangster spotted Lowry and his wife leaving a bar and followed them. In a fit of rage the upset husband tried to cut off Lowry’s head and when that proved too difficult, he shot him in the head. A couple of weeks later the gangster's wife shot him in the leg. Supposedly, Jimmy relayed the story to Barboza. But how did Jimmy know the story?

Nina:

Because the unnamed gangster was Jimmy! And it wasn’t a couple of weeks later, it was just 12 hours after Lowry’s body was found. Jimmy arrived at City Hospital on September 3rd at 4 in the morning with a bullet wound in his left leg. He told the police that two men had shot at him six times. He said he first noticed a station wagon following him after he drove away from a diner on Mass Ave. near Uphams Corner. He said the car had tried to cut him off several times without success and he drove onto Bird Street in Dorchester. The wagon pulled abreast of his sedan and a man fired three shots, all of which missed. Jimmy tried to escape on foot from his own car. The attackers fired three more shots and one hit his leg. After he was hit, Jimmy told the cops that the station wagon sped away and he hobbled back to his car. He further claimed that he drove back to Roxbury where he turned his car over to a friend and then had taken a taxi to the hospital. 

Lara:

Jimmy said he knew who had shot him.

Nina: 

It was his wife, Maureen!!! 

Lara: 

But he refused to say who it was.

Nina: 

Because it was his wife!!!

Lara: 

Really you couldn’t make these stories up!

Detective Billy Stuart arrested an ex-con named William McCarthy that same evening. Stuart said he’d been tipped off that McCarthy was carrying. Gee I wonder who tipped him off? You know that was a bogus pinch, but they needed a body to keep suspicions off of Jimmy’s wife, and Stuart was as crooked as the day was long. McCarthy was held on $50,000 bail for a September 14 hearing. But, of course, nothing ever happened. The police said that Jimmy had been shot by mistake.

Nina:

The only mistake was that she missed!

Lara:

Too bad she wasn’t a better shot. She would have done everybody a favor!

Back to Stuart. Jimmy was already in bed with Detective Billy Stuart at this point. Wimpy Bennett allegedly introduced the two of them. And like Stuart’s relationship with Wimpy the relationship was quid pro quo. Billy Stuart helped the guys out when they needed rescuing, like when Jimmy and Wimpy got shot at. But in return they had to help him out with his cases. 

Nina:

The Feds claim that they targeted Jimmy to become a Confidential Informant at this point, but like I said earlier, that’s a lie. He may have only been labeled a “Potential Confidential Informant”, but he already had a CI number assigned in late 1963.

Less than a month after he was shot by his wife, Jimmy blinded an unnamed man with an unknown substance. Just like Mesiti. The information was provided to SA Rico and noted in a 302 dated October 8, 1964. Later that same informant told Rico that Jimmy still wanted to kill Teddy Deegan. It was noted in a memorandum from Rico to the Boston SAC, and in a memorandum from the SAC to Hoover.

Lara:

And they never lifted a finger to warn Teddy or anyone else that they knew was marked for a hit!

Nina:

Don’t get me started. I still believe it was Rico’s wish hitlist they were running off of.

In November 1964, Stevie Flemmi was officially opened as a Confidential Informant and given a CI number: BS-955. His handler was H Paul Rico. Stevie was the last of the men we’ve covered today to be made an official FBI informant. His brother and the other members of the Winter Hill gang were already on the FBI books as informants: BS-868, BS-869, BS-919, and BS-954. That brings us to Frank Salemme, Stevie’s friend and business partner and FBI informant. 

Francis Patrick Salemme was born on August 18, 1933 to Romeo Salemme and Mary Bridget Haverty. The Salemme family were from Campania, and the Haverty family were from Northern Ireland. Frank was a jock from a young age, participating in football, hockey, and track and field. He had several auto repair shops that he ran in the Somerville area, and does not appear to have a criminal record prior to 1969 when he went on the lam. We’ve gone through the newspapers, but have come up with nothing. However, the FBI claimed that he had been convicted of assault and battery before 1969, but no arrest date was given, and we can’t find any newspaper articles to back that up. The mugshot used in the wanted poster was from 1965, but again no newspaper articles indicating why the photo was taken.

There’s also a rumor that Frank was in the can with one of the Morellis in 1957 and that’s how he got hooked in with the Patriarca family, but it’s only a rumor. 

Either way, in our opinion, Frankie Salemme became an FBI informant in either early 1963 or late 1964 and his handler was Denny Condon.

Lara:

For our listeners that didn’t catch episode 19, let’s give a brief history of Condon.

SA Dennis Condon was born in Boston's Charlestown neighborhood on Bunker Hill Street on November 23, 1923, the youngest son of Dennis Condon Sr and Nora Haggerty. Condon was a Boston College graduate, a Lieutenant Commander in the U.S. Naval Air Corps and served aboard the U.S.S. Siboney in the Pacific Theater at the tail end of World War Two. He became an FBI agent on January 29, 1951, just one month before H. Paul Rico did. His first assignment after training was the Philadelphia office, beginning March 28, 1951. He worked there for ten months. He did a brief three month stint in New York, before returning home to Boston on April, 11, 1952.

By the beginning of the 1960s Condon began handling informants. 

Nina:

Frankie Salemme admitted later that SAs Rico and Condon would drop in and visit with him and Stevie on a regular basis, several times a week. Salemme would also do favors for Rico. For example, one time Rico was in a bad car accident in an FBI motor pool car. He couldn’t take it back to the motor pool in the condition it was in, so he called up Frank, who agreed to fix the car. Frank thought it would be a little scratch, something that just needed a little touch-up, because Rico had downplayed the damage over the phone. But when Rico arrived, Frank realized that the car needed way more work than Rico had implied. Rico had been at the race track and somehow got rammed. Frank finally finished the job at 10:30 at night and when Rico drove away in the fully repaired car, the paint wasn’t even dry.

Lara:

And we’re supposed to believe that Frankie and Rico had this relationship out of the kindness of their own hearts? A relationship that went on for a decade. Yeah OK!

Nina:

Don’t question the narrative! Shame on you. No one can tell me that he didn’t make a deal in the end that he would testify in exchange for the Feds keeping his CI status a secret, so Frankie could keep his street cred. Even if half of the information was bogus, the authorities got to close the books on countless cases.

Lara:

Well one murder that was never closed out was George Ashe. Ashe was stabbed 50 times and shot in the head on Christmas night 1964. Reminds me of how Anthony Sacramone was killed. Jimmy’s handiwork. Ashe’s body was discovered in the front seat of his sedan at roughly 6 am on the 26th. Hoover was informed of the murder on the same day that it took place. The official story was that Jimmy Flemmi murdered George Ashe because he found out that Ashe was also an informant for the FBI. Ashe had made a deal in 1959 to get a reduced sentence on a murder accessory charge. Like Jimmy, his handler was SA Rico. I wonder who told Jimmy that Ashe was an informant?

Nina:

I know that was a rhetorical question, but the question I wonder is why did Rico need Ashe taken out other than his hatred of the McLaughlins?

Ashe had been released from prison in May of ‘64. Ashe was a bartender at the club that Jack Kelley and his crew frequented. As Lara mentioned before the brutality and method of Ashe’s murder was very simialr to that of Anthony Sacramone, and Iggy Lowry. The Feds all the way up to Hoover were aware of this and continued to use Jimmy as an informant anyway. Although Jimmy was not made a Top Echelon Informant until March 1965.

Lara:

Meanwhile, Jimmy Flemmi had been working with good old Detective Billy Stuart on a counterfeiting case, even traveling with him to New York to give testimony at a grand jury. 

Just 3 days before Jimmy was made a Top Echelon Informant, he was picked up on the wiretap at Raymond Patriarca’s office complaining about Sacramone being killed back in October, saying it was unnecessary. He would know since he was the one who killed him, but he spread the word on the street that Teddy Deegan had killed Sacramone. The Feds knew Jimmy was responsible for Sacramone’s death. Although in the early  302s they kept referring to him as his brother Americo.

Nina:

The following day, another CI reported to SA Rico that Teddy Deegan was on the hit parade because Teddy was with the McLaughlins. Then on March 12th, 1965, the same day that Jimmy was officially anointed as a TECI, Teddy Deegan was murdered. Rico was formally assigned as Jimmy’s handler. A memorandum was sent from the Boston SAC to Hoover that day:

“Vincent Jimmy Flemmi is being designated as a target in the Top Echelon Criminal Informant Program. Flemmi is also believed to be involved in the murders of the following people: Frank Benjamin, John Murray, and George Ashe. Flemmi was the subject of an unlawful flight to avoid prosecution.” 

Lara:

Word of Jimmy’s relationship with Detective Billy Stuart finally reached Jerry Angiulo who reported it to Raymond Patriarca in Providence, but not until after Teddy Deegan had been murdered by Jimmy. Patriarca fluffed it off and continued to meet with Jimmy. On May 3, 1965, Raymond was picked up on the wiretap questioning Jimmy about his relationship with Billy Stuart. Later that evening, Jimmy was shot at again. This time while walking out his front door. He did a complete somersault, and when his assailants closed in for the kill shot, he started firing back, emptying his own .38 caliber revolver. Jimmy later claimed that Punchy McLaughlin and two other men had shot him. He refused to name the other two.

Two days later, Joe Barboza and Ronnie Cassesso were back at Raymond’s office. This time asking for permission to take out Sammy Linden who they claimed was financing the McLaughlin gang. They included Jimmy, who was laid up in the hospital, in their pitch. 

Nina:

Patriarca wasn’t the only one unhappy with Jimmy’s relationship with Billy Stuart. On June 8, 1965, Rico paid Jimmy a visit at the hospital and told him that he could only provide information to the FBI and only receive payment from them. Obviously, the comments on the wiretap about Jimmy talking to Billy Stuart ruffled some feathers. Jimmy told Rico, “I am willing to aid the Bureau, as I can help put away the individuals who attempted to kill me.”

The following day another memorandum was sent from the Boston SAC to Hoover. It once again listed out the murders Jimmy had committed, but in a few months time that list had grown. It read: Frank Benjamin, John Murray, George Ashe, Joseph Francione, Edward “Teddy” Deegan and Iggy Lowry. The memo also noted that Jimmy was convinced that it was the Mclaughlins who tried to kill him on May 3. His emotional stability was called into question. The memorandum continued on to say that although from all indications Jimmy will continue to commit murder, the agent, H. Paul Rico, believes that the informant’s potential outweighs the risk involved.

Lara:

I suspect that either Rico convinced Jimmy that it was the McLaughlins who tried to take him out, or at the least to run with the story. Let’s face facts, Jimmy didn’t have a shortage of people that would want to bump him off.

On June 25th, Jimmy appeared in court with his attorney Al Farese to be arraigned on illegal gun carrying charges stemming from the night he was shot and returned fire at his two would be assailants. He was ordered held on $10,000 bail which was promptly posted by a bail bondsman. Jimmy returned to the hospital for yet another surgery. 

Nina:

The following month Rico and SA Raymond Ball sent a memorandum to Hoover stating that Spike O’Toole and two others, possibly Punchy McLaughlin and Stevie Hughes were the ones who shot Jimmy. They also stated that Jimmy said his only regret was not killing Georgie McLaughlin before Georgie went on the lam.

Not long after that, and on September 15th, 1965 another memorandum was sent to Hoover stating that Jimmy was closed as an informant. Jimmy had jumped bail and failed to appear in court on September 3rd to face assault with a dangerous weapon with intent to murder charges after he attacked John Cutliffe in late August. 

“In view of the fact that the informant, Jimmy Flemmi, is presently a local fugitive, any contacts with him might prove to be difficult and embarrassing. In view of the above, this case is being closed.”

Lara:

“Embarrassing!” What’s embarrassing is that they let a serial killer not only roam the streets but protected him. Then decided to drop him because he went on the lam, not because he was slaughtering people.

Nina:

Well, they just traded one Flemmi for another. On November 3rd, 1965 the Boston SAC notified Hoover of a potential addition to the Top Echelon Criminal Informant Program:

“Stephen Joseph Flemmi (BS-955-PC), is being designated as a target in this program. Although the LCN [La Cosa Nostra] in this area has not actively taken part in this gang war, there is every possibility that they may move into the picture in the near future and since Flemmi is in contact with the leaders of the different groups that are against the remaining McLaughlin faction, and that all these groups are very aware of the possibility of LCN moving in to support the McLaughlin group, it is felt that Flemmi will be in a position to furnish information on LCN members in this area.” 

Lara:

On November 15, 1965 at 7 in the morning, Robert Palladino’s body was found on the corner of Beverly and Causeway Streets near North Station. There was a single bullet hole in the back of his head, and the authorities said he’d been killed somewhere else and dumped. Less than 12 hours later, Ray DiStasio, a McLaughlin gang associate and bartender at the Mickey Mouse Cafe in Revere, and John B. O’Neil, an innocent bystander, were killed. It was 5 pm in the evening and O’Neil was just getting cigarettes.  Later that same evening, Stevie Flemmi was arrested along with Earl Smith and Peter Poulos. The cops were looking for Jimmy who had been on the lam since September. Jimmy was a suspect in all three murders, but the authorities were particularly interested in the Palladino murder since Palladino was a grand jury witness in the 1964 murder of Margaret Sylvester.

Jimmy Flemmi was arrested in the early morning hours of November 19, 1965. He’d been on the lam for two and a half months. Brookline and State Police Detectives took Jimmy into custody after finding him hiding in a closet in an apartment on Hamilton Road near Comm Ave. The official version of events was that the cops had come to the apartment to serve a warrant for a motor vehicle violation. When they knocked on the door, a male voice replied that the person they were looking for wasn’t there. The cops ordered the man to open the door or they’d use force. Johnny Martorano opened the door to the cops. A search of the apartment commenced, and a State Trooper wearing civilian clothes opened the closet door and pointed his gun at Jimmy. “Oh my god, I’ve never been so close to death!” Jimmy exclaimed.

Nina:

On January 26th Jimmy Flemmi was deemed incompetent by the court. But that didn’t stop the Boston FBI office from using his prior statements in their reports to Hoover and in later court cases. Jimmy pleaded guilty to jumping bail and was sentenced to 4 to 6 years in State Prison on March 10th, 1966. Johnny Martorano pleaded guilty to harboring a fugitive and was sentenced to jail for 6 months.

In March of 1966, Rico was commended for his “excellent work since he was exclusively assigned to handle Top Echelon Informants. “He has an exceptional talent in his ability to develop informants and his participation is considered outstanding.”

Lara:

Let’s bring in John Martorano who was born on September 13, 1940 to Angelo Martorano and Elizabeth Hunt. His younger brother James was born eleven months later on December 10, 1941. Another set of Irish twins! The family moved from Somerville to East Milton when Johnny was in 8th grade. Like Frankie Salemme, Johnny was a high school jock. He turned down multiple football scholarships and instead decided to frequent his father’s after hours lounge, Luigi’s. Johnny’s father was partners with Johnny Williams. Williams was one of the old guard in the Boston Mafia. Angelo Martorano even brought his son Johnny to Williams to try to talk some sense into him, but we all know that was a waste of time.

On April 24, 1966 a month after being released from prison, Anthony Veranis was savagely beaten and shot in the head by Johnny Martorano after he tried to outdraw Johnny in a Dorchester after-hours joint. Martorano dumped his corpse in the Blue Hills off Route 128. Veranis had boxed with Joe Barboza, Rocco DiSiglio and Rico Sacramone. 

On the same day that Anthony Veranis was killed, David Sidlauskas was also murdered. Sidlauskas had a minor record. His body was found near the Long Island Bridge in Quincy, and was still warm when it was discovered. He had been shot in the chest and arm. It’s believed that William Geraway, an associate of Johnny Martorano, killed Sidlauskas. Geraway would later go on to provide statements about Joe Barboza’s admissions in the Teddy Deegan murder and the murder of Clay Wilson that Barboza committed in California.

Nina:

We mentioned the murder of Palladino a short while ago. According to Johnny Martorano’s own confession, that was his third hit. If you listened to episode 26, you might recall that Johnny’s brother Jimmy was convicted for beating Margaret Sylvester with a shoe. Margaret was a waitress at Luigi’s. Johnny Martorano said he heard that two men were going to testify that his brother, Jimmy, was involved in the slaying.

In response, he said, he tracked them down and shot and killed both men, Johnny Jackson and the Margaret’s boyfriend, Bobby Palladino. Jackson, who was a waiter at Luigi’s was murdered outside his Queensbury Street apartment in Boston on Sept. 28, 1966, and Palladino’s body was found near North Station on Nov. 15, 1965. 

Lara: 

Sammy Linden and Stevie Hughes were murdered in a hail of armor piercing bullets fired from a rifle in a passing black sedan as they drove along Route 114 in Middleton at 2 in the afternoon on September 23, 1966. Several witnesses said they saw the black sedan with three men and a woman overtake the two men at the top of a hill and counted at least seven shots. Sammy Linden’s car knocked down several concrete guard posts and plunged off a ten foot embankment and into a swamp. 

Jimmy Flemmi and Joe Barboza had been seeking permission from Raymond Patriarca to kill Sammy Linden as early as May 1965. But Joe Lombardo found out, and was livid that they wanted to kill Sammy, and intervened on Sammy’s behalf, but in the end that didn’t save Sammy. Stevie Flemmi copped to the murder of Stevie Hughes, but not Sammy Linden. 

Nina:

Which makes no sense because they were both in the car together when they got killed.

In January of 1967, William L O’Brien was shot and killed while a passenger in Robert DeLeo’s car as they drove along Morrissey Blvd. DeLeo was injured and would later testify that Johnny Martorano was the man who shot him and killed O’Brien. O’Brien’s body was found dumped in Stoughton. O’Brien was another early associate of Whitey Bulger’s. Another one of O’Brien’s partners in crime was DIckie Joyce, who decades later would be named as a suspect in the Gardner Museum Heist. We’ll be discussing this murder and the others in more detail when we cover the hit parades of ‘65, ‘66 and ‘67 a little later this season.

Lara:

With Jimmy Flemmi officially out of the picture, on February 14, 1967 his brother, Stevie was approved as a Top Echelon Informant, according to an FBI Office of Professional Responsibility Report.

In late December of that year, William Bennett and Richie Grasso were killed. Stevie would later confess to the murder of William Bennett and Grasso. Johnny confessed to the murder of Grasso. Bennett was shot to death and pushed from a moving car in Dorchester on December 23rd. Grasso was collateral damage. They used him to lure in William Bennett who was trying to find out who killed his other two brothers Wimpy and Walter, but Grasso freaked out and Johnny shot him too.

Nina:

Then in January of 1968 Atty. John Fitzgerald lost his leg in a car bombing that Stevie Flemmi and Frank Salemme supposedly carried out. Frank was later convicted but Stevie was not. We’ve covered the car bombing in 3 other epsidoes, so we’ll link to those in the show notes if you want to hear more about that and our theories. Both would later go on the lam in September 1969 after SA Rico warned them that they were going to be indicted for the bombing.

Lara:

Jimmy Flemmi was released on March 28, 1969, but back in front of a judge again on January 8, 1970 when he pleaded innocent of charges of assault with intent to murder, assault, and illegally carrying a weapon. Jimmy was allegedly shot in the shoulder when he tried to kill Black Jimmy Abboud while both men were riding in a car together. True to form, the ADA requested bail to be set at $100,000. Jimmy’s attorney, Joe Balliro, asked for bail to be set at $5000. Bail was eventually reduced to $25,000, but on the fourth day of the trial, Jimmy failed to appear in court. He was convicted in absentia the same day. The ADA said he’d seek indictments charging Jimmy with being a habitual criminal. Jimmy was later indicted for failure to appear for trial. The FBI and the Staties captured Jimmy in October at a trailer camp near Westover Air Force Base. He later tried to claim he’d been kidnapped as his excuse for failing to appear in court, but the State Supreme Court upheld his 14-18 year sentence. 

Nina:

On January 5, 1973, Jimmy was transferred from Walpole to a prison in Illinois along with Georgie McLaughlin, and Ronnie Cassesso. Peter Limone was sent to a prison in Oregon. The authorities claimed that they’d been plotting to take over the prison. Limone and Flemmi sued later that month.

Jimmy was stabbed in the chest by a fellow prisoner in September of 1974. In May 1976, Jimmy was granted a weekend furlough and went on the lam again. The authorities finally caught up with him in Baltimore almost exactly two years later. He’d been hiding out in Maine for some portion of that time. And good old Johnny Martorano was visiting him regularly, bringing him supplies.

On October 16, 1979, Jimmy Flemmi died of a drug overdose in Norfolk State Prison.

Lara:

Kevin Weeks later recounted a conversation that took place at Jimmy’s wake which he attended with Whitey Bulger. “While we were viewing Jimmy lying in the casket, Stevie was standing there with his mother and father and [his brother] Michael. Mary went over to Jimmy and said, crying, 'Vincent was such a good boy. He never hurt anyone.' Stevie looked at her and said, 'Stop, Ma. He killed everybody.’

Nina:

We didn’t include Kevin Weeks and Patrick Nee in this episode as we won’t be getting into the 70s and 80s until next season. There were quite a few other associates of Buddy McLean and Howie Winter that we chose not to cover today. Joe Barboza being one of them. If you want to know what Joe was up to before he turned state's evidence listen to episode 24. 

Lara:

There’s so much more to cover, but hopefully this episode provided a clearer picture of how these men were connected to each other and how those connections will play out through the 70s, 80s and 90s.

Next week we will be heading back to Federal Hill in Providence, RI. Nina and I have decided to take one more look at what Raymond Patriarca was up to with the five families in New York. We both felt it’s important to give some background on why Raymond was willing to give the ok to take out Teddy Deegan before we release the two episodes dedicated to Teddy, his murder, the men falsely accused and incarcerated and the truely gulity parties.

As always, thank you for listening! Please share an episode with someone you know and leave a review. Keep the fan mail coming.

Lara and Nina:

BYE!