Top Echelon Informant Program - License to Kill

Lara:

Welcome back everyone! This week Nina and I are going to be discussing the FBI’s Top Echelon Informant program. Originally created back in 1961 by J. Edgar Hoover, it was first known as the Top Hoodlum Program.

Nina:

Hoover really seemed to love the word hoodlum.

Lara:

Tell me about it! The 302s from the 1950s and ‘60s are riddled with it! On March 14, 1961, Hoover issued a letter to the SACs:

“Today the press, television and radio along with the express interests of the Administration keep this phase of criminal activity in a position of prominence in the public eye. Certainly we cannot relax even momentarily our efforts in combating the criminal underworld including the prosecution of Top Hoodlums. The foundation from which we forge our attack must be kept strong and fresh with a full flow of information from well placed informants. All agents in conducting investigation of criminal matters should be constantly alert for the development of new informants and new potential informants who may be in a position to assist us.”

Nina:

The program was inaugurated on June 21, 1961. Each SAC was charged with cultivating informants from the top tiers of organized crime. 

“It is mandatory that the development of quality criminal informants be emphasized and the existing program be implemented and greatly expanded. You are again reminded that the penetration and infiltration of organized criminal activity is a prime objective of the Bureau, and to accomplish this it is necessary to give a renewed impetus to the development of quality criminal informants.”

Boston wasn’t on that original list, but that soon changed, and this episode will focus on the informants and agents of the Boston field office in the 1960s. And the lives ruined and lost because of this so-called “special program.” But first let's give an overview of the program itself. The SACs were instructed to “develop particularly qualified, live sources within the upper echelon” of organized crime. 

Each informant was given a code number when they were placed on the books. And each FBI office had their own set of numbers. BS for the Boston office, CG for Chicago and so on. Then a number: 812, for example. Then either C for Confidential Informant or PC for Potential Confidential Informant. When a source was made a Top Echelon Informant, the letters TE would be added at the end of the sequence. For example, Vinnie Teresa’s number was: BS 812-C-TE. That code was supposed to protect the Confidential Informants as the memos whizzed across the country between the various FBI offices. But as you will see, that didn’t work out in practice. 

Lara: 

In addition to the TE informant program, the FBI used electronic surveillance devices to listen in on conversations between organized crime leaders, including informants. As we mentioned in previous episodes, in 1962, the FBI placed wires in the headquarters of Raymond Patriarca and Jerry Anguilo. March 6, 1962 for Raymond’s office and July 1962 for Jerry’s office. Each wire was given a code like a live informant would have but an asterisk was placed at the end to mark the differentiation. Raymond’s wire was BS 837-C* and Jerry’s wire was BS 856-C*. It was SA Kehoe’s responsibility to monitor and create the logs and 302s from the wire at Patriarca’s. He was paid an annual salary of $11,415 for his efforts. At first, the full transcripts were sent to Hoover in DC, but after just 6 days Hoover issued an airtel:

“You are authorized to discontinue submission of daily teletypes in this case and in lieu of same submit summary type airtels on Tuesday and Thursday of each week. . . .  This case is to continue to receive full-time attention and every effort must be made on a daily basis to develop any criminal violation which Patriarca is committing or has committed with any relevant statute of limitations period.”

The same directive was handed down from Hoover concerning the wiretap at Jerry’s office later that same year. On December 8, 1963 Hoover sent another airtel to the Boston SAC. 

“Boston should submit a weekly summary airtel to the Bureau setting forth information obtained from this source and a verbatim transcript of any significant data specifically set out.” In the future your airtels setting forth the information received from BS 856-C* can be set out as you would information received from a regular informant.  By doing so, it will not be necessary to submit your communications as JUNE mail and the information can be filed in the regular case file.”

Nina:

I still feel bad for Kehoe having to listen to that nonsense day in and day out. But I can’t tell you the number of times I’ve wanted to scream at him from beyond the grave for over-complicating the whole thing. In some of his reports to Hoover he would pretend like he had 12 different sources: BS T-1, BS T-2, and so forth. But when you got to the end of the report, and saw the key, it turned out that all twelve sources were just the wiretap. It also appears that Kehoe was inserting intel from live sources (specifically Vinnie Teresa) and passing it off as being from the wiretap.

Lara:

Have I mentioned recently that intel laundering should be a crime? 

Nina:

Yes, you have! 

Lara:

Ok I’ll spare you another tirade.

These special informants were only useful if their identities remained a secret.They weren’t required to testify or wear a wire. Most were given immunity to commit illegal activities such as drug dealing, bookmaking, loan sharking and fencing stolen items. But they were NOT sanctioned to commit acts of violence and murder. At least on paper.

Nina:

But there was a don’t ask, don’t tell policy in place that allowed more than a few serial killers to roam the streets. I’m sorry, but you can’t tell me that guys like Jimmy Flemmi and Joe Barboza weren't serial killers. I won’t even get into Whitey, Stevie Flemmi and Johnny Matorano. Literally a license to kill.

Tell us who the first TE was in the Boston office.

Lara:

The first TE informant in the Boston office was Vincent Teresa, BS 812-CTE.  If you’ve been listening in recently, you know I am less than a fan of Vinnie’s. The court martialed Navy cook fancied himself to be a walking encyclopedia of organized crime in New England. To add to the list of Vinnie’s let’s say qualities, he was also a degenerate gambler.

Nina:

If it wasn’t for Vinnie’s uncle, I doubt he would have been much more than a court martialed cook and thief.

Lara:

Vinnie’s uncle was Joseph Lombardo's driver. The story goes that Dominick Teresa saved Joe Lombardo and Joe was so grateful that he gave him a job.

Nina:

That sounds like another one of Vinnie’s tall tales. That being said, in the 1930 census, Dominick Teresa did report that he was a chauffeur, so at least that part of the story might be true. But I’m pretty sure Joe Lombardo was perfectly capable of taking care of himself. Maybe it was Uncle Dominick who escorted Joe to the police station when Joe turned himself in after the Gustin Gang murders. The Teresa family had all lived in the West End since at least 1911: Vinnie’s grandmother, his aunts and uncles and cousins.

Lara:

My family’s neighborhood. I know you want to torment me and tell me that my aunt’s father-in-law’s cousin’s kid was married to Vinnie’s aunt.

Nina:

That’s what you get for having such a resentment against Vinnie! 

Lara:

I have another twisted connection to Vinnie too, but that has to wait until season 2. Do you want to tell us anything else about Vinnie’s family before we move on?

Nina:

Vincent Charles Teresa was born on the 28th of November 1929, the oldest child of Charles Teresa and Mary Calogero. Vinnie was named for his deceased grandfather, Vincenzo Teresa, who had come to the United States from Termini Imerese, Sicily, in 1891. Vinnie’s mother’s side was a bit harder to track down but I believe that they were from Calabria.

Let’s move onto Vinnie’s crimes.

Lara:

Vinnie was arrested in September 1958 for conspiracy to violate the Small Loans Act. 20 secret indictments were handed down to ten men. The Staties said that the accused had bilked more than half a million dollars in exorbitant interest rates and forced many of their victims into crimes to pay their debts. Cornelius Crowley was the Officer in Charge of the case. You might remember him from episodes 8 and 10 as he was the arresting officer twice in dad’s cases.

In December, Vinnie pleaded guilty to the conspiracy charge. But that same day, the Boston Globe reported that the judge allowed him to change his plea to innocent. Bail was continued at $5000 and he was freed. 

Nina:

I suspect he made a deal to feed information to the Feds in exchange for his release. He might not have had an assigned CI number at that point, but he was probably giving them information off the record. But what drove him to become a CI? His father, Charles Teresa died in January 1962. So maybe that influenced his decision.

According to Vinnie’s memoir, Jerry was pissed off at him after he beat up a Gambino caporegime named Joseph Paterno who was based out of NJ. Paterno went crying to Jerry, and Teresa was called to a sit down. Vinnie claimed that Jerry always hated him, and wanted to use the beating as an excuse to whack him. He claimed he was living in fear for his life until Raymond intervened on his behalf. 

We’ll never know the real reason, but it is also more than likely that Vinnie was a paid informant throughout the 7 years he served as a CI. Yes, he boasted about how much money he earned and how much was stolen from him by Raymond, but to describe those claims as hyperbolic would be a huge understatement. The reality is that Vinnie was officially feeding info to the Feds for more than a year before Valachi testified at the McClellan Hearings in October 1963. And given his number in relation to the other numbers in the Boston Office, I actually think it was closer to two years.

Lara:

After listening to those recordings and researching Valachi, I believe that the Feds told Valachi what to say from the info they had gleaned from their wiretaps and other CIs. They used him as a vehicle to get their message out to the public and feed the fear monster.

Nina:

I agree. How was it possible that this relatively low ranking soldier had such a wealth of information not just on a local level, but a national one? Not realistic. 

Back to Vinnie’s statements.The first 302 we could find with information provided by Vinny to SA Kehoe was from September 20, 1962 when he reported that Jerry Anguilo was made “boss”  of Boston. The next 302 was from November 29, 1962. He provided the Feds with a detailed outline of Italian organized crime. In that 302, Vinnie claimed to be the grandson of a Don from Palermo, and said that was the reason he knew this information. Another likely tall tale. As I said, Vinnie’s Sicilian grandfather passed away more than a decade and a half before he was born. Vinnie’s maternal grandfather was not Sicilian and had abandoned his family about the same time that his paternal grandfather died.

Nevertheless, Vinnie provided details to the Feds about what qualified a man to be “made.” The candidate would have had to have performed an “outstanding” act and have the proper temperament and be trustworthy. The man would be proposed and voted on before being inducted. Vinnie went on to say that once a man was made, he couldn’t resign and only death would terminate the contract. A Don had to be Sicilian, but Italians could be made.

Lara:

That brings me back to Raymond and Jerry. How were they bosses? They weren’t Sicilian!

Nina:

I know! That’s why I still think that the old timers, Bruccolla, Lombardo, Modica, and Nene put them both out front to be lightning rods and take the hits. Vinnie went on to list the Dons as follows:

Phillip Bruccolla, Joseph Lombardo, Joseph Pepino (Joe Modica’s honorific), Anthony Lamattina, Frank Cucchiara, Anthony Della Russo, and Frank Morelli. We introduced several of these men in Episode Eleven.

Vinnie said Raymond represented Phillipo when he was in Italy, and Jerry represented Raymond in Boston.

The made men were:

Anthony Sandrelli, Ralph Lamattina, Nicolo Giso, Michael Rocco and Henry Selvitella.

Lara:

Vinnie also gave information on Vito Genovese of NY and Frankie Carbo of Baltimore. The info he gave on Genovese was sketchy and Frankie Carbo wasn’t the boss of Baltimore. 

When questioned about Peter Limone, Vinnie said he worked for Jerry, but didn’t believe he had been made yet.

Nina:

At least Peter Limone was actually Sicilian!

Lara: 

As we mentioned in last week’s episode, Vinnie was informing on Pro in 1963. The first date we could find was November 4, 1963 when he said that he believed Albert Giorgio, Billie Aggie and Pro robbed the Boston 5 Cent Savings bank. Then on December 2nd he said he believed Billie and Albert held up the Suburban Trust Company. He referred to Pro as Reno, and asked the Feds not to look into him as Pro would know he gave him up.

Nina:

What he was feeding to the Feds was questionable. For instance he said that Ralphie Chong and Nicky Giso blew $150,000 of the mob’s money, and that Ralphie was marked for a hit. Ralphie lived into his 90s. Later Vinnie would say he was robbing banks with Pro and Billie. By that time Vinnie was close to 400 lbs. Picture him hopping over a bank counter or not being picked out of a line up immediately. 

Lara: 

I’ll pass on that imagery, thanks!

In 1969, Vinnie was convicted of transporting and selling stolen securities. While he was appealing that conviction, he was arrested again for a similar offense. He became a cooperating witness in 1970, and entered the witness protection program. Throughout the remainder of his life, he never admitted that he was an informant prior to that. He said that SA John F Kehoe was the one who convinced him to turn State’s evidence. Tell us about Vinnie’s handler.

Nina:

Vinnie’s handler was SA John F Kehoe Jr. The same man who was manning the wiretap at Raymond’s office. We already introduced Kehoe in Episode 9, and I’d encourage you to go back and listen to it. But I’ll do a short recap here.

John Francis Kehoe Jr was born on 17 Oct 1919 to John Kehoe Sr and Emma O’Connell. He was the captain of the Boston College High School hockey team his senior year. Kehoe went on to graduate from Boston College in 1941. 

He applied to join the FBI straight out of college. His draft card has the DC address of the FBI penciled in across the top. He was stationed in New York City, among other locations, before returning back home to Boston in 1947. 

Lara: 

Kehoe was one of the original members of McNamara’s team tasked with solving the Brinks case. Once that job was completed in 1956, the team wasn’t dissolved, but rather rebranded and became devoted to rooting out Organized Crime. Eventually it was expanded to cover Massachusetts, Maine, New Hampshire, and Rhode Island. All of New England except Connecticut, which fell under New York’s jurisdiction.

Kehoe was a member of that team, but in addition, he ran the so-called “informant program”. 

On February 13, 1961, Bobby Kennedy declared Raymond Patriarca one of the 39 “top hoodlums” in the US. The following months the agents were directed to recruit new CIs. Then on June 21st that same year the Top Echelon program was officially launched.  

Nina:

Two more Top Echelon Informants, BS 801-CTE and BS 829-CTE, were recruited in the Boston area in the latter half of 1961. As far as I can tell, neither of them were ever outed. I have my suspicions about who one of them was, but I don’t know for sure, so I’m reluctant to name him. He always swore up, down and sideways that he wasn’t a Confidential Informant but he was so vocal about it, it makes me think he was lying. And for all his protestations, he still ended up getting gunned down in the 70s. So make of that what you will.

There is one other Top Echelon Informant who was recruited as a CI much earlier than 1961 that I just want to touch on briefly. BS 670-C-TE was informing on activities in the Federal Hill neighborhood of Providence at least into the late 1960s. This person was never outed either, and I keep going back and forth on who I think it is. But we’ll be bringing all three back in later when we talk about Federal Hill.

Lara:

Before we move on, I want to briefly cover what happened to Vinnie Teresa after he entered the Witness Protection Program. He testified at the McClellan Hearings. Three novels later he must have become bored with the “normal” life. Under his identity of Charles Cantino, he was arrested in 1982 for smuggling exotic birds and Komodo Dragons.

Nina:

You left out the conspiracy to smuggle cocaine!

Lara:

Well compared to the Komodo Dragons that seemed mundane. In Seattle in 1990 he died of kidney failure. Before we introduce our next TEI, let’s talk about another one of the handlers.

Nina:

Dennis Condon was born in Boston's Charlestown neighborhood on Bunker Hill Street on November 23, 1923, he youngest son of Dennis Condon Sr and Nora Haggerty. His father, a Boston fireman, passed away in 1937. Another Boston College graduate, Dennis was 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.

Condon’s speciality throughout the 1950s seems to have been catching serial escapees. There’s one story where he catches a 25 year old woman who had escaped from the Woman’s Reformatory at Framingham on four previous occasions. Intriguingly she managed to be out on her own for months at a time before the FBI caught up with her. 

When Frank Martin Feeney and Russell Halliday escaped from Norfolk Prison in the summer of 1954, Condon was the FBI’s representative in court. The other law enforcement agencies waived jurisdiction in favor of Federal prosecution. You can listen to that story in our Thanksgiving Bonus Episode.

By the beginning of the 1960s Condon began handling CIs. Another mystery informant who was reporting to Condon, BS 1159-PC, became a TE in 1970. In total it appears he was a handler for at least 6 of the TEs in the Boston office, and many other PCs and CIs.

Lara:

On February 23, 1963 Condon received a $150 cash incentive for his contribution to the establishment of highly confidential informants in the FBI’s efforts to take down Jerry Anguilo. That’s just after the wire at Jerry’s office was officially approved and Condon was given the additional responsibility of that device.

On February 25, 1965 Condon received a $150 incentive award for his outstanding work investigating and apprehending Georgie McLaughlin, who had been on the lam for the Sheridan murder.

Nina:

I know it was 1965 and money went further in those days but that still seems paltry. 

Lara:

In November of 1966, Condon was “involved in a substantive error write-up case when a review of an informant file assigned to him disclosed an instance of failure to properly disseminate information obtained from the informant.”  

An informant had reported that an individual who was a suspect in another FBI case had a machine gun in his possession and was “crazy.”  Condon didn’t send this information to the Treasury Department. Condon said that he inadvertently failed to follow the proper protocol because the suspect was under active investigation by the FBI. No administrative action was taken against him.

On March 31, 1967 Condon received an excellent rating for how he handled complicated matters. He was said to be enthusiastic and showed a great interest in the Bureau’s work. It further stated that he had “outstanding knowledge of the hoodlum and gambling element in the Boston area and is considered to be an outstanding investigator.”  According to the review, Condon was not interested in administrative advancement.

Nina:

Although there is much more to tell about Condon, we’re going to move on for now. The next TEI we’re discussing is Vincent “Jimmy” “The Bear” Flemmi. Good old BS 919-C. Remember that one of the qualifiers for being a TEI was being a serial killer. I’d say Jimmy qualified under that moniker. Vincent Flemmi was born on September 5, 1935 to Giovanni Flemmi and Mary Irene Misserville. He and his brothers, Stevie and Michael, who would become a cop, grew up in Roxbury. 

Jimmy’s record dated back to 1949 when he was still a juvie. Then in 1953 he was sentenced to 18 months in the House of Correction on robbery charges. But by 1954 he was out again and once again arrested for assaulting two Navy officers. He was sentenced to 2 years in the Dedham House of Correction but he didn’t serve the full term. In December of ‘56 he was picked up for robbing a credit union. 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 Richie in the Desisto home invasion. Once Jimmy arrived in Walpole, Mesiti was disfigured and blinded in an acid attack. Although Jimmy was never tried for that attack nor was anyone convicted, the odds that it was Jimmy who attacked Mesiti are pretty high. Especially considering Jimmy’s track record of violence both in and out of prison.

Lara:

In July of that year, Jimmy attempted to escape from custody, but that was a flop. On October 12th, he was sentenced to 10 years in State Prison. In June of 1960, Jimmy was charged with stabbing to death a fellow inmate, 30 year old Raymond Gabriel, only to be acquitted in March of 1961.

Talk about a mistake! Not long after, Jimmy was back on the street. On March 27, 1964, Jimmy claimed he found Andrew Pappas stabbed and dying in the gutter on Dudley St in Roxbury. On May 4, 1964 Francis Regis Benjamin was beheaded by Jimmy. In September, Jimmy was shot in the leg in Dorchester. Two months later, Jimmy was targeted to become an official CI. This was after SA Condon was reporting in 302s regarding informants’ statements that Jimmy had cut off Francis Benjamin’s head, threatened to kill Teddy Deegan, and bragged that he only wanted to kill as it was easier than robbing banks. The informant also stated that Jimmy felt he could become the number one hitman in the area and intended to do so.

Nina:

Like you said earlier, the man was a serial killer. In a letter to Hoover from the Boston office dated June 4, 1964, he was advised that Jimmy was a suspect in a number of gangland murders and told an informant he planned to be the number one hitman in the area. Shortly after the Feds began grooming him as a CI. 

Lara:

On September 28, 1964 Jimmy blinded an unnamed man with an unknown substance. The information was provided to 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.

Nina:

It was believed that Jimmy murdered George Ashe in late December 1964 because he found out that Ashe was an informant for the FBI. George Ashe had made a deal in 1959 to get a reduced sentence on a murder accessory charge. His handler was H Paul Rico. Ashe was stabbed 50 times and shot in the head. Hoover was informed of the murder on the same day that it took place. 

I have to ask the question, was Rico responsible for calling some of the hits in the 60s? To protect himself and his pet CIs? And one CI in particular?

Lara: 

You know I have my suspicions about that possibility too. Nothing is impossible in any of these stories. 

Nina:

In late January 1965, just after Dorothy Barchard found Henry Reddington murdered, Jerome Sullivan wrote in the Boston Globe: “There is hardly a detective on the Boston police force or an agent in the local FBI who was surprised that Reddington was slain. His photograph, his home address and the type of car he drove have been contained in a confidential Boston police circular for more than six months. The circular, bearing the names and pictures of 18 to 20 known hoodlums, divides the list into two groups – those friendly to suspected slayer and FBI fugitive George P McLaughlin and those hostile to him.”

Lara:

The article concluded: “The police circular is beginning to take on the appearance of a list of those marked for death.”

Nina:

In January of 1965 an airtel was sent to Hoover from the SAC in Boston. The airtel stated that according to information received via the wiretap at Raymond’s office a man named Frankie stated, “all the people are getting scared of Jimmy.” Frankie asked Raymond to talk to Jimmy and tell him there should be no more murders in Boston. 

Lara:

On March 3rd Jimmy and Joe Barboza were picked up on the wiretap at Raymond’s office. Frank Smith had been giving Jimmy orders about who to whack without Raymond’s permission. That same day Jerry Anguilo told Raymond that Jimmy was with Barboza when they took out Joseph Francione, and Frank Smith had ordered the hit. Raymond told Jerry that he was to tell Smith that there were to be no more unsanctioned hits. Jerry told Raymond that he lectured Jimmy about not killing people just because they got in an argument.

Nina:

A lot of good that did. I don’t understand why Jerry and the rest of them let him roam around causing trouble. As for Frank Smith, I have my doubts about that story. But Episode 31 will be dedicated to him.

Just 3 days before Jimmy was made a CI he was picked up on the wiretap at Raymond Patriarca’s office complaining about Rico Sacramone being killed back in October, saying it was unnecessary. The word on the street was that Teddy Deegan had killed Sacramone. 

I’ve got to interject again here: Rico Sacramone wasn’t killed until 1975. It was his brother, Anthony, who was murdered in Everett in the early morning hours of October 17, 1964. He was stabbed four times in his head and neck before being shot twice in the back of the head. The Everett police said, “Whoever murdered Sacramone first tried to stab him to death, then went berserk and shot him when the knife failed to kill.”

Everything about that description says Jimmy Flemmi murdered Sacramone. But the Feds were covering for Jimmy and told the Everett police that Teddy Deegan had committed the murder. Jimmy also told Raymond that Teddy Deegan wanted to whack Bobby Donati because he believed Bobby was trying to set him up to be whacked by Buddy McLean. Joe Barboza was also present at that meeting in Providence. Raymond reportedly gave Jimmy and Barboza the greenlight to take out Teddy Deegan.

Lara:

Teddy was with the McLaughlins and both Sacramone brothers were with Buddy McLean. Buddy had met Rico Sacramone in the can during a boxing match. Now, I know that there’s been more than enough speculation that Teddy and Sacramone were both junkies, so that was the excuse for two rivals to be in the car together. Teddy was long dead before I was born, but his brother Larry was a constant in my home until he passed. And all of dad’s guys were at one point in with the McLaughlins. There was never any talk of Teddy being on drugs. Now we all know Jimmy was on everything but the kitchen sink and died of a heroin overdose. The more likely scenario is yours, that Jimmy killed Sacramone. Both were with the McLeans. Jimmy probably concocted the story about Teddy killing Sacramone to cover his own insanity and for another excuse to kill Teddy. I don’t believe that Teddy was a hitter. A thief yes, but not a killer. Jimmy on the other hand was a stone cold killer and proud of it. We won’t get into the Teddy Deegan story here. Episode 29 will be dedicated to Teddy. 

The following day, another CI reported to Rico that Teddy was on the hit parade because Teddy was with the McLaughlins. Then on March 12th, 1965, the same day that Jimmy is officially anointed as a TECI, Teddy Deegan was murdered. SA H. Paul Rico was formally assigned as his 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.” 

Nina:

The following month, the first reported contact between Jimmy as a CI and Rico occurred. Two days later, the wiretap picked up Jerry Anguilo telling Raymond that Jimmy and Wimpy Bennett were stool pigeons. Raymond fluffed it off. Jerry also told Raymond that Jimmy was paid $1500 to dispose of the body of a dead girl and had cut her into pieces. He also reported that Jimmy was bragging that he was friendly with Detective Billy Stuart of the Boston Police Department. The same Stuart that Wimpy Bennett had a “relationship” with. 

We have not discussed this previously. At some point, it is unclear when, Boston Police Detective Billy Stuart and Wimpy Bennett linked up. Stuart became a cop in 1954 and was mostly doing welfare fraud cases in the late 50s. The story is that Wimpy was informing to Billy Stuart. But Wimpy was also using the Detective for protection. When Wimpy was shot at outside his home in early 1965, the first person he tried to contact was Billy Stuart. The detective wasn’t available but Wimpy let the cops know that he knew who had shot at him. That story does not seem to have made the newspapers. But it didn’t need to. Jerry had his own source at the BPD, and he was happy to play messenger and head to Providence in his truck and let Raymond know. Raymond later reportedly said that “anyone who would call upon law enforcement to help them when they have a problem has got to be a “stool pigeon”.”  He also said he didn’t want to believe it because Wimpy had once done him a favor years before.

Lara:

Jimmy and Rico met again the day after Jerry informed Raymond that Jimmy was a stool pigeon.

Then on May 3rd, Jimmy was shot again. This time by two men with shotguns. He was on his way to meet Joe Barboza. Earlier in the day Jimmy was picked up on the wire at Raymond’s being questioned about his relationship with Stuart. The wire also picked up Raymond giving Jimmy the ok to whack Frank Smith. 

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 at the hospital, in their pitch. Flashback to March of 1963, the wiretap at Jerry Anguilo’s office at Jay’s lounge picked him up saying Ronnie was a rat.

Nina:

Jerry thought everyone was a rat. But between the wire at Raymond’s and the wire at Jay’s Lounge, the Feds knew everything Jerry was saying.

Lara:

Joe Lombardo himself intervened on Sammy’s behalf. Lombardo was evidently extremely angry that Ronnie Cassesso and Barboza were associating with Flemmi. Lombardo told Tameleo that he was to tell Jimmy and Barboza not to touch Sammy. 

Nina:

On June 8, 1965 Rico told Flemmi that he could only provide information to the FBI and only receive payment from them. Obviously, the comments on the wires about Jimmy talking to Billy Stuart ruffled some feathers. Jimmy stated, “I am willing to aid the Bureau, as I can help put away the individuals who attempted to kill me.”

Lara:

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. 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.

Nina:

On June 25th, Jimmy appeared in court 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. The following month Rico and SA 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.

Lara:

Then on August 22nd, Wady David became the 23rd gangland slaying. Wady, a heroin dealer, was friends with both Spike and Jimmy. We’ll get more into Wady’s story later in the season when we profile some of the narcos from the Boston area.

Nina:

But it wasn’t long before buyer’s remorse set in for the Feds. On September 15th 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 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.”

Jimmy’s bail was forfeited and he was officially a lamister.

Lara:

But no need to worry. The Feds had a backup plan, Jimmy’s brother, Stevie. On November 3rd, 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.” 

Nina:

Less than two weeks later Jimmy was arrested on the outstanding armed assualt with intent to murder charges. In court he claimed “Punchy tried to kill me.” The trial dragged on for months. On January 26, 1966 he was deemed incompetent by the court. But that didn’t stop the Feds from using his prior statements. With Jimmy 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.

Lara:

Finally, Jimmy was sentenced on March 10th to 4 to 6 years in State Prison. He was released on March 28, 1969, but back in front of a judge again on January 8, 1970 on attempted murder charges once again. Eventually he was sentenced to 18 years in Walpole State Prison. He was stabbed in the chest in September of 1974. The following year he was granted a weekend furlough and fled. The authorities wouldn’t catch up with him for another 3 years. On October 16, 1979, he died of a drug overdose in Norfolk State Prison.

Nina:

Before we move on to Joe Barboza, let's cover H. Paul Rico. My least favorite Special Agent. 

Rico graduated from Boston College in 1950 with a Bachelor's Degree in History. On February 26, 1951 he was inducted into the FBI. He completed his training on April 21st and married his high school sweetheart the same day. He was sent to Chicago, where his first child was born in November of that year. He was transferred back to Boston in April of 1952 because his father was ill. His father died in 1955, and his mother died a little more than two years later. 

Lara:

On March 5, 1956 a confidential memorandum from the Boston field office SAC was sent to Hoover. The memorandum was about James “Whitey” Bulger: 

 “This office had known Bulger because of his suspected implication in TFIS tailgate thefts.  We knew of his extremely dangerous character, his remarkable agility, his reckless daring in driving vehicles, and his unstable, vicious characteristics.”  Agents Paul Rico and Herbert F. Briick, undertook to develop a PCI [Possible Confidential Informant] who could and would inform on Bulger’s location...  SA’s Briick and Rico continued to contact (redacted name) and ultimately developed his confidence and willingness to cooperate. The SAC recommends that Rico, who took Bulger in to physical custody, and the other agents involved in Bulger’s arrest receive a letter of commendation, with particular emphasis on the fine work of SA’s Rico and Briick in cultivating the informant who made the arrest possible.” 

Nina:

Two weeks later Hoover notified Rico of his promotion to Special Agent.

“It is a pleasure to approve this promotion in view of your superior accomplishments in connection with the Bank Robbery case involving James J. Bulger, Jr., and others.”  

Hoover also commended Rico for his outstanding work “in developing a valuable source of information” and “in developing other confidential sources of information.”

Lara:

As Rico and his fellow agents were busy recruiting informants under Hoover’s new directive, there was a gang war brewing in Boston. The lines were already drawn, but it wasn’t just between the two gangs themselves. Most criminals fell into one of the two camps. You were either with the McLaughlins or the McLeans. But it wasn’t just the street guys. The Feds chose a side too. In their effort to wipe out the “Italian faction” of organized crime, they made a deal with the devil or devils in this case.

Nina:

A perfect example of this is Ronald Dermody. But the Alliance between the Feds and Winter Hill went on long after the 1960s. As most of you know, Whitey Bulger and Stevie Flemmi, the two most famous CIs of the Boston office were aligned with Winter Hill. Let’s tell Ronnie’s story.

Lara:

Ronnie Dermody’s dead body was discovered slumped across the front seat of a parked car on the corner of School and Belmont Streets in Watertown. The story goes that Ronnie was in love with his sister-in-law, Dorothy Barchard, and was jealous of her longtime boyfriend, Spike O’Toole. He went to the McLaughlins and told them that he’d take out Buddy McLean if they’d take out Spike. Of course, Spike O’Toole was an associate of the McLaughlins, so I don’t think that the McLaughlins were actually that interested in the deal, but if Ronnie wanted to kill Buddy for them, they weren’t going to say no. However, Ronnie, who had just recently been released from prison, had no idea what Buddy looked like. He shot wildly with a .22 at a man he mistook for Buddy, but didn’t manage to kill him. From his hospital bed, 33 year old Charles Robinson told the police that he had no idea who had shot him or why. 

Nina:

But now the word was out that Ronnie had intended to kill Buddy McLean, but failed. Panicked, Ronnie called the one person who he thought could help him. FBI SA H Paul Rico. Ronnie knew Rico from back in the mid-50s when he’d been arrested for the Pawtucket bank robbery that he had committed with Whitey Bulger. But unbeknownst to Ronnie, Buddy McLean was a favorite Confidential Informant of Rico’s. Rico set up a meeting with Ronnie, but Rico didn’t show up alone, he had Buddy with him. Buddy shot Ronnie 3 times in the head through a partially opened window on the passenger’s side of the vehicle. The fatal bullet struck Ronnie in the neck and passed out on the left side of his head, leaving a trickle of blood that ran down his face. 

Lara:

A witness reported hearing the gunshots, then about a minute later, the slamming of a car door and a car engine firing up. Her husband stepped outside in time to see Rico and Buddy driving away in a blue sedan. The two men returned to Rico’s home in Belmont, where Rico let Buddy hide out in his basement until the danger of arrest had passed.

Ronnie was the first of Whitey Bulger’s original crew to be released from prison, and the first to be murdered. 

Nina: 

It wasn’t the first time that Rico would sanction murder as an FBI agent and it wasn’t the last. 

On January 14, 1966 The US Attorney’s Office in Boston, Massachusetts, received a report entitled “Boston Gangland Murders; Criminal Intelligence Program” that was prepared by John Kehoe dated January 14, 1966.  It covered the investigative period between November 15, 1965, and January 11, 1966.  This report was approved by Boston SAC James Handley and contains a section entitled “Informants” that is completely redacted except for the following sentence:  “Redacted is BS 955-PC [Stephen Flemmi], contacted by SA H. Paul Rico.” 

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:

With Jimmy locked away and Stevie on the hook, the FBI was in the market for a new informant. On March 8, 1967 Rico and Condon met Joseph Barboza at Walpole State Prison. Barboza told them he would speak to them as long as they didn’t use his statements in testimony against him, and they agreed to keep the conversation confidential. He told Rico and Condon that he used to meet with Raymond Patriarca to get permission before he made a move. Barboza “made statements that he was going to kill several” people who killed three of his friends Thomas J. DePrisco, Arthur C. “Tash” Bratsos, Joseph W. “Chico” Amico, and they stole $70,000 from him. Barboza stated that he knew what happened in practically every murder that had been committed in the area.  He also said that he wouldn’t provide information that would cause Jimmy Flemmi to ‘fry’ but would consider furnishing information on these murders.” 

Nina:

Those meetings continued for weeks. Denny, as Barboza called Condon, and Rico were frequent visitors in their effort to romance him into becoming an informant. But knowledge of those visits leaked out. On March 21st the Boston ‘Record American’ received a call from someone at the Walpole prison that Barboza was taken out by federal authorities and headlines read  “U.S. Government opened its war on crime by bringing gang leader from Walpole for appearance before a federal grand jury.”

Lara:

I don’t want to get into Barboza’s background and history in this episode since he will be the topic of discussion in episode 26. But he had a record dating back to 1948 when he was just 13 years old. And like Jimmy, he was essentially a serial killer. 

On March 28, 1967 the Boston SAC sent a memorandum to Hoover regarding an interview of Joseph Barboza conducted on March 21, 1967. It was a follow-up to an interview conducted on March 8, 1967. Rico and Condon conducted the interview with Barboza at the Federal Building in Boston.  Barboza conferred with his attorney, John Fitzgerald, and the Feds knew that Fitzgerald’s girlfriend, Dorothy Barchard was an informant, of course. They didn’t mention that Barboza was also having an affair with her. Barboza stated he would not testify to any information that he was furnishing. After his meetings with Rico and Condon, he decided that they had a common enemy in the “Italian organization”, and wanted to help the FBI bring them down. Barboza hoped that DA Garrett Byrne appreciated his assistance and would cut him a deal on his two cases pending in Suffolk County.  Barboza told the Feds that he discussed his cooperation with Jimmy Flemmi, and that he was considering having Patrick Fabiano cooperate with the FBI also.  He said Jimmy thought that was an excellent idea.  Barboza told Rico and Condon that Teddy Deegan had been causing some problems and had been “out of order” at the Ebb Tide Restaurant.  The heavily redacted document stated:

“This office is aware of the distinct possibility that Barron [Barboza], in order to save himself from a long prison sentence, may try to intimidate Fabiano into testifying to something that he may not be a witness to.” 

Nina:

Barboza’s plea for leniency fell on deaf ears. On April 24, 1967 he was convicted for unlawfully carrying a weapon and a dagger in a motor vehicle, and sentenced to not more than 4-5 years for the first charge and 4-5 years for the second charge.  Both sentences were to be served concurrently. But Rico and Condon didn’t stop visiting Joe seeking his continued “cooperation.” 

Lara:

Then on July 3rd Rico and Condon were once again given $150 bonuses. It was noted that Condon received accolades for his handling of TEIs BS 868 C-TE, BS 954 C-TE and BS 955 C-TE. Two days later Barboza was transferred into protective custody at a secret location. 

On August 9th a memorandum was sent to Hoover from the Boston SAC.

“In a statement to the press, District Attorney Byrne stated that this tremendous penetration into the La Cosa Nostra and the hoodlum element was effected through the outstanding investigative efforts of the FBI and his office. As a matter of information, this entire case which was presented to the grand jury by DA Byrne was developed through the efforts and able handling of Barboza by SA H. Paul Rico and Dennis M. Condon of the Boston office. They also cooperated fully with DA Byrne in the preparation of this matter for the grand jury. I know that this indictment would not have been possible in any sense of the word if it were not for the efforts of these agents and the FBI at Boston. . . .  I further recommend that Supervisor John F. Kehoe who supervised this entire program and was involved deeply in the developments and the planning relative to Barboza and the matters attendant to this indictment be strongly commended for his excellent supervision.”

Nina:

That was one of 60 commendations SA Kehoe received over the course of his three decade career in the FBI. He went on to be appointed Commissioner of MA State Police in 1971.

We’ll get deeper into Teddy Deegan and Joe Barboza in their respective upcoming episodes. The same for what happens on the Hill with Raymond and the boys throughout the season. In season 2 we’ll be covering the 1970s which includes the end of the Top Echelon Programs in 1978. It was rebranded as the Confidential Informant Program, but it was the same old, same old. The two most famous Informants, Whitey Bulger and Stevie Flemmi, continued to murder not just wise guys, but innocents as well. All known, sanctioned, aided and abetted by the authorities. 

Lara:

The Bureau’s end goal was to wipe out LCN. We will see how all of that plays out over this season and the next one. Raymond’s decision to choose sides with the McLean/Winter Hill faction and essentially with the Feds will be the topic of many an episode. Next week we’ll be discussing Sam Giancanna, the rumored CIA plots to kill Castro and theories about the mob being responsible for the assasination of President JFK. Please subscribe, share and leave a review!

Nina & Lara:

BYE!