It's a story too wild to be fiction, yet it's all true. A secret alliance between America's most feared criminal syndicate and the highest levels of US intelligence. An audacious Cold War plot to assassinate Fidel Castro that reads like a James Bond screenplay, but with more misfires, betrayals, and bodies left behind. The story begins in Havana, Cuba, where the mob made millions controlling casinos until Castro's revolution swept it all away in 1959.
And in the panicked of the Cold War, the CIA turned to the unthinkable, hiring mafia gangsters to do its dirty work. I sat down with investigative reporter Thomas Mayer, whose book Mafia Spies blows the lid off one of American history's darkest and most secret chapters. Mayer and I have mutual friends among investigative journalists. He is among the best. I've placed a link in the show notes to help you keep track of the cast of characters.
Mayer's journey into this twisted tale did not start with the mafia. It began with JFK and the Kennedys. I've written previous books about the Kennedys. I wrote a book about twenty years ago about their Irish Catholic immigrant experience, and also wrote another book about ten years later about the Churchills and the Kennedys. In both those books, I did tangentially mention the incident that happened with JFK and Judith Exner, who in Mafia Spies is generally known as
Judy Campbell. That Judith Exner was her married name. But it was a, an affair that involved JFK, a Chicago Mobster by the name of Sam Giancana, and Judy Campbell. And so even though I had mentioned them very briefly, I was intrigued about perhaps writing a book about, Giancana. And I wasn't really sure if I had enough meat on the bone, if you will, to do a book
by itself. And it wasn't until I did more research, and I learned about, this particular aspect of how the CIA hired both Sam Giancana and another really fascinating gangster by the name of Johnny Roselli. It wasn't until I found out about this plot to kill Castro by the CIA by hiring these two gangsters to go out and kill Castro during the Cold War, that I realized, that this was something that was really intriguing, particularly the friendship between Giancana
and Roselli. It was almost like if you ever watch that movie Butch Cassidy and the Sundance Kid, it's kinda like these two outlaws who are hired by the government to to to do really a dastardly deed, and kill a foreign leader, Fidel Castro, at the height of the Cold War. Set the scene of what the tension was between The United States and Cuba. What was the vested interest of the mafia in Cuba and then the US government, I e, the CIA?
Well, in the late fifties, what happened there were two things that really shook the American government. One was, the the shooting off of the Sputnik rocket. It was the first thing into outer space, and that was sent up by the Russians. And so that really threw off the US government because we came out of World War two very preeminent. We were the first ones to develop the bomb.
So the idea of having a rocket that could conceivably have a have a an atomic bomb attached to it, that really sent shutters through official Washington. But the other satellite, if you will, was the creation of Cuba as a satellite of the Soviet Union, Russia, at that time. And, the revolution led by Fidel Castro really sent, again, shivers down the the spines of the
the US government. And so we couldn't do anything about shooting Sputnik out of the sky, but the decision was made that, Castro had such held such a a threat to the defense and the security of The United States that something had to be done about it. And it was approved by president Eisenhower at the end of his administration, and it was adopted by the Kennedy administration, in the early nineteen sixties. So the Kennedy administration was aware that there
was a plot to assassinate Castro? You know, they have said no. You know, people who associated with, president Kennedy's administration have said no. But when you look at the papers, these documents that particularly have been released in recent years pertaining to the JFK assassination, a lot of them have to do with the operation by the CIA in Florida. Essentially, we were running an undeclared war out of, the Miami, the, the Keys area, of of
Florida. And so even though there's been denials about it, we were definitely trying to kill Castro. And, certainly, Bobby Kennedy was aware of that. Even despite the denials, when you look at all of the papers, it's impossible, it seems to me. I mean, Bobby Kennedy was flying down to Florida during the course of this. He was in he would he had his hands all over this. He was the attorney general, but he was, almost in essence, the head of the CIA overseeing this operation
to overthrow the Castro government. Well, and here he is, the attorney general, yet the US government forms an alliance with the mafia, a criminal organization. And do they end up kind of giving them a free pass on their criminal activities? Well, you know, it's interesting because particularly on that point, the Kennedys, Bobby Kennedy claimed that he didn't know anything
about it. It's hard to really believe that, frankly, given all of the evidence, all of the documents, and all of his deep participation in in this. So, yeah, I I think what was interesting about the the mafia, Giancana, Sam Giancana, and Johnny Roselli with this, is that they thought by agreeing with Frank Sinatra, who was a pal of Giancana's and Roselli's, Sinatra was a very prominent supporter of JFK in the nineteen sixty election.
And they felt by supporting the the Kennedy effort that they would go easy on them. In fact, when Bobby Kennedy became attorney general, though, he put up he put more of the heat on the mafia than had, than had ever been before. And so Xi and Khan and Roselli were really upset, as the Kennedys came to power that they essentially betrayed or, at least in their perception, betrayed the promise of going easy, getting a getting, like, a get out of jail free card.
And in fact, they were being chased by the FBI more than ever. Well, when you have this alliance, they start cooking up these schemes to assassinate Castro. And it's it's James Bond esque. But it, like to me, it becomes the gang that couldn't shoot straight. Yeah. You know, I I think I that aspect of the almost the, dark comedy or comedic aspect of of this, particularly when you look back with some degree of perspective historically.
Or certainly in, my book was made into a TV series on Paramount plus by the same name, Mafia Spice. And I think we kinda capture that as well in the TV show, both the book and the TV show. There was a certain level of craziness about the whole thing that I think is captured in both. Try to portray that. I I think there's a level of hubris, a a word that we don't hear hear
too much. But hubris, the whole idea that, whatever I do will be fine, it will will never blow up in my face, and that this is well intentioned. And that wasn't the case. It was very poorly thought out, and it was very suspect
in terms of getting involved. The idea of the the United States government getting involved with the mafia was suspect to begin with, but the fact that, the attorney general of United States was overseeing an operation that had any type of component with organized crime is something that remained a secret for for about ten years afterwards. The all of this really didn't come out until the mid nineteen seventies, and still many details are are still coming out with some
of these JFK assassination papers. But it does give you pause about the overall judgment of the Kennedy administration. Well, one of the methods they'd come up with to kill Castro was a a poison cigar with botulism in it and stuff. Did that come out of the James Bond movie? I mean, it it none of this stuff ever worked. Right. Well, I guess if you come up with the idea by watching a movie, maybe Yeah. That may be that may be the grounds why it doesn't work. It is fictional to begin with.
You know, it's interesting to me in in looking at this time period, the Bond movies were just getting off the ground. JFK was a big fan of James Bond novels. So was Jackie Kennedy. Jackie Kennedy actually sent a copy of one of the James Bond novels to the head of the CIA, Allen Dulles. And Dulles also heard at at a dinner party that the creator of James Bond, Ian Fleming, was invited to JFK's
residence for a dinner party. And so Dulles, who wanted to keep his job, decided to keep the president happy and his wife happy and and all of those fans for James Bond that he directed people in the CIA to see if that any of these ideas from James Bond films might might be doable. We might be able to take some of these ideas, exploding cigars or or, other type of devices, gadgets that somehow could be killing devices. These were all suddenly the focus
of a lab at the CIA. The other thing I found interesting then is that this assassination conspiracy meetings unfold at the Fontainebleau Hotel in Miami, which is the big scene of one of the James Bond movies, and in Vegas, which is another big setting for the early James Bond movies. It is. Goldfinger, it begins with somebody jumping off of a very high diving board at the Fontainebleau Hotel
in Miami Beach. Miami Beach is, well, specifically, the Fontainebleau is a fascinating scene that because the the the big first meeting between the the, CIA and the mafia takes place at the Fontainebleau. And it's around the same time that Sinatra is appearing at the Fontainebleau. He's hanging out with Sam Giancana, the gangster, who's getting involved in all of this plot to kill Castro along with Johnny Roselli. And Sinatra is filming a TV special at the Fontainebleau
with Elvis. Actually, you could go on to YouTube and actually see Elvis and Frank Sinatra singing, together. And that's at the Fontainebleau during the same time period. And then we see other meetings in Vegas, which in those days, the mob controlled. Right. Well, Las Vegas, particularly became important. Las Vegas, the Las Vegas that we know, its origins became,
started right after World War two. But at that time period, Cuba was still the place that had its own casinos, were was run by the mob. In the fifties, most Americans, certainly on the East Coast during the winter months, they didn't go to Las Vegas. They would go to Havana. And there are a number of different casinos, including one that was run specifically by, Sam Giancana and Johnny Roselli, the San Sushi. But there are other mob controlled casinos.
When Castro came to power in 1959, he shut down all of the American casinos, all of the American businesses, but he shut shut down all of the mob controlled casinos as well. So that's where it it really gave a big boost to, Las Vegas. But that was also why the mob, who was now losing millions of dollars that they used to make in Havana. That's why the mob was so angry with Castro and what had happened in Cuba.
Did Sam Giancana, who was out of Chicago, become involved because he had lost so much money down in Cuba? Tell us about him. I think so. I used to work as a reporter for the Chicago Sun Times, and that was also part of the rationale for me, the curiosity that I had about Gina as a figure. But, fundamentally, yeah, it's about money. Money, money, money, money. The outfit, the the mob as the mob was known in Chicago, was headed by Giancana
at that time period. It was on the scale of a Fortune 500 company in terms of its revenues. And so it was all about money. And so when they lost, the casinos in in Havana, it was a place where the mob ruled. In fact, Meyer Lansky, another gangster, was appointed by the Cuban government as the head of tourism and such. So it was it was a little heaven, if you will, for the mafia and all of its nefarious activities. And and Sam Giancana had big ambitions.
And so his friendship with Johnny Roselli really was a a a a reflection of those ambitions as well, because they got involved not only, with Las Vegas and and running things in in Cuba, but the idea of now getting involved with the government, becoming hitmen for the CIA, that was extraordinary. That's the type of thing that the average mobster didn't do. They were concerned about, like, local stuff, local gambling,
numbers, rackets, stuff like that. No. These two guys, Roselli and Gene Conner, they were talking about getting involved in entertainment, the movies, and and they certainly got involved with the CIA. Was Roselli the connection to the CIA? How do they how do they make that connection? Yeah. It's it is a little bit of a complicated one. But, yes, Johnny Roselli was the main connection. He knew a guy named Bill Harvey, who was known as the James Bond, the real life James Bond of
the CIA. I think there's a couple of people that can make that claim. But, certainly, Harvey was a very successful spy for the CIA over in Europe, and he was acquainted with, Johnny Roselli. And so the connections there were part of it, part of the story. But there was also a middleman involved in this. And he also, this middleman worked for Howard Hughes, the the then
the wealthiest man in The United States. And it was, through that middleman that the CIA was connected to Johnny Roselli, and and Roselli recruited, Sam Giancana into this whole escapade, if you will. For those that don't know, Howard Hughes was the Elon Musk of today. Right. I was about to say that. Yes. Yeah. And it He was. All kinds of technology. But that connection to Hughes is what, Robert Mayhew? Right. Exactly. His name was Robert Mayhew.
And really a fascinating character because he had been an FBI agent, had a lot of friends in the CIA, and he had done other jobs for the CIA, the type of jobs that the CIA didn't didn't wanna get its hands dirty, if you will. And so they kinda hired out people that they trusted, and Mayhew was one of those people. And it was Mayhew who knew Roselli pretty well. He had invited Roselli to a backyard party, and that's where there was a couple of CIA people there. That's
where they met Johnny Roselli. So when the subject came up from very up on high from the White House and from the upper reaches of the CIA that we wanna get rid of, Fidel Castro, they said, well, how do we do this without, getting it connected directly to to us? And so they employed Robert Mayhew, and then Mayhew recruited the mob into this whole scheme to kill Castro. And these people in the spy craft are usually referred to as cutouts.
Yes. They have a language unto themselves, the whole spy world does, and Cutout is one of those. But, essentially, he was a he was a a go between. He was an intermediary. He was a middleman between, or if you ever watched the, Godfather movies, there's at one point where somebody says, the family has a lot of buffers. Well, Mayu was, in a way, a buffer for the CIA. It was a way of implementing their plans to kill Castro without, in their eyes, hopefully getting directly, held responsible
for it. But, of course, that didn't happen. Eventually, it all came out. And then part of the plot to overthrowing was the Bay of Pigs invasion, which broke down, fell apart. Yeah. This was an attempt this was the big attempt to overthrow the Castro government. The Cuban Americans who fled to Florida were trained by the CIA. They had a base down in Florida. They they were trained in other countries as well, but but there was a big effort to train people in Florida.
And that was it was remarkable to me that we could run, essentially, an undeclared war in Florida, and it really did not come out. People were not even fact, there there was one incident where there was some type of shooting incident, and the the local newspaper in Miami found out about it. And they were gonna write a story about it. And the CIA and the the, US government contacted the newspaper, and they decided not to run the story.
What ends up happening to Sam Giancana and Johnny Roselli, the two mobsters that got into bed with the CIA? The friendship between Sam Giancana and Johnny Roselli, fascinated me. I think that was one of the big appeals of of this book on a personal level. Just their friendship they had started together in Chicago. Johnny goes out to Hollywood. He's sent by Al Capone out there because Johnny suffered from tuberculosis. Johnny becomes kinda the mob guy out in Las Vegas. He was a fixer out there.
He knew a lot of the studio heads. Sam Jean kinda rises to the head of the Chicago mob. His wife drops dead, screaming at their kids. They she has they have three daughters, and suddenly, Sam Jean kinda finds himself as bachelor father. Johnny is kind of a Casanova character. So these two men together, to me, just on a personal level, was fascinating, how they interacted with them and with Sinatra, the Rat Pack, and such.
I think getting involved with the CIA was part of the ambition that Giancana had, which was to grow the mob outside of just Chicago into, not not only domestically, but even in international places like Cuba and other other places internationally, particularly in terms of casinos and things of that nature, things that would make big, big money, not petty anti type of gambling.
And so the the relationship between, Roselli and and Giancana was based upon their own ambitions and and and and getting involved with the CIA. Thinking that if they if they did a favor for the CIA by killing Castro, not only would they get back into Cuba, but they would have a won over on the on the government. They would they would have a get out of jail free card. And, that sounded very attractive to them, and that's really why they got involved
in all of this. And what ends up happening to them at the end of this checkered story? Well, it becomes even more complicated. Giancana was warned, don't draw attention to yourself because it can be disastrous, just like it was with Al Capone or, in more recent vintage mob history, John Gotti in New York. In other words, if you love the limelight, if you love the celebrities, and he was told, don't do that. Gene Conner was told, don't
do that. In fact, he was selected by the elders in the mob in Chicago, who were retiring or semi retired, at least keeping an eye on things. But they thought that Giancana was married, that he he was known for mowing his lawn out in the suburbs, that he was a solid guy. He was a money earner, and so will give the job to Sam Giancona. When his wife drops dead, he starts hanging out with Johnny Roselli. He meets various different people, the Maguire sisters. He starts going out with one of the
Maguire sisters. And now his photos and and he becomes friends with Frank Sinatra. So now the, we have Sam Giancana as a prominent figure in the in in the tabloid newspapers and such. So this is the type of attention that the mafia in Chicago, they didn't want any of it. And so they they wound up, after the JFK assassination, Giancana essentially is pushed out of power in Chicago. He winds up going down to Mexico and trying to get involved in international, business and such.
He eventually comes back to The United States in the mid nineteen seventies. By that point, he's got some health problems. He comes back to Chicago, and there's a question about whether or not he'll he'll try to grab the reins of the Chicago mob and run it again. He had been replaced and whether or not he would try to grab the power there.
And, when that happens in that time period, he subpoenaed by the senate to talk about, what was had happened in the early 1960s and the attempts to kill Castro. Again, with the a lot of things are complicated. There's a lot of spinning plates in this story. After the Watergate investigations of the early 1970s, the senate was looking at the operations of the CIA, and they became aware of the plot to kill Castro involving the two gangsters, Giancana and Roselli. And so the senate
subpoenaed both of them. And in the case of Giancana, there were investigators who flew out to see him. And that night, he had dinner with his family. And and when the family went home, Sam was cooking up a little snack for himself. He had, like, a little man cave in the cellar of his home in Oak Park, and it was late. And I brought 11:00 or so. And somebody, we still don't know who, came in with a silencer and put six bullets into Giancana's head.
And he did the the assassin did so, with the telltale mark of putting the shots around his mouth, which basically was a message. Anybody who talks like this will wind up just like Sam Giancana. They'll wind up dead. By that point, Johnny Roselli realized that he was had a target on his back. He he went, down to Florida, start started hanging out with his sister, living with his sister. But he was subpoenaed. He did initially say virtually nothing to the senate.
But then the FBI, who was investigating Johnny and Johnny had gotten in trouble, some cheating scandals at the Friars Club in Beverly Hills. So the FBI, the government was looking to deport Johnny Roselli because Johnny Roselli had a a big secret in his life. He was an illegal immigrant from Italy. His mother came over. He he did not have the proper papers, and he was feared being deported. In fact, Johnny Roselli was not even his real name. It was completely made up by Roselli himself.
His real name was, Filippo Sacco. And when the government found this out after much investigation of Johnny, they said that we're going to deport you. So Johnny, by the mid seventies, was worried he would be deported, and he intimated that he knew something about the JFK assassination. His lawyers intimated that to the senate committee. And so they subpoenaed him again. And just before he was to be deposed about what he knew, Johnny
was murdered. He went off to play golf, and they later found his body in a 55 gallon barrel that was thrown into the bay in Miami Beach in that area. And that was the end of Johnny. As they say, sleeping with the fishes. Exactly. So it's quite a story. And both the murder of Giancana and both the murder of Roselli are unsolved. Readers of my book, Mafia Spies, will come to the conclusion well, you get a pretty good idea of who I think was responsible, had his hand involved, in the murder
of of both Giancana and Roselli. And that's the last man standing. Castro is the last man standing on one level, but there's a mobster who was involved in all of this, guy named Santo Trafficante. And I think he had a hand in both murders. The secret plot and partnership between the CIA and the mafia to kill Fidel Castro first became public during the investigation of the Watergate scandal in the mid-1970s.
Some of the ex CIA operatives involved in the plot to kill Castro played a part in the bungled burglary of the Democratic National Committee headquarters office at the Watergate Office condominium complex in Washington, DC on 06/17/1972. President Richard Nixon, facing likely impeachment for his role in covering up the scandal, resigned two years later. Nixon became the only US President to resign.
At the time of the break in, I was a new congressional aide to Representative Wright Pattman, chairman of the House Banking Committee. I would later conduct Watergate related investigations on his behalf for the Joint Committee on Defense Production. Since then, I've watched the revelations explode into an industry of conspiracy theories about the assassination of President John F. Kennedy. Did the CIA do it? Did the mob
do it? Did Castro do it? Did the FBI miss warning signs about Lee Harvey Oswald? Well, the latest batch of JFK documents released by President Donald Trump reveals that the KGB had Oswald under surveillance during his time in The Soviet Union. Covertly observing Oswald at a firing range, they concluded he was a bad shot. So, how did Oswald, perched in the Sixth Floor window of the Schoolbook Depository in Dallas, hit the president with a deadly headshot in a moving motorcade?
In my next episode, Mayer reveals a new revelation about the Warren Commission and how then CIA Director Allen Dulles steered the murder investigation away from the CIA mafia plot to kill Castro. You'll wanna stay tuned for this one. This is Robert Riggs reporting.