Historical Figure / Narrator (e.g., JFK or Castro quotes) (2:45)

Castro will tell the General assembly the United States is seeking to overthrow him.

David McCloskey (2:51)

Kennedy really looks to the CIA to get the business of the Cold War done.

Historical Figure / Narrator (e.g., JFK or Castro quotes) (2:55)

Castro and his fellow dictators May rule nations, they do not rule people.

Gordon Carrera (3:01)

The CIA were kind of playing jfk.

David McCloskey (3:05)

In the eyes of some CIA trained militants, Kennedy had become a traitor to the cause.

Historical Figure / Narrator (e.g., JFK or Castro quotes) (3:11)

B26 bombers of the Cuban exile air force attack Castro's airfield.

David McCloskey (3:16)

Everything that could go wrong does out.

Gordon Carrera (3:18)

Of ammunition, men fighting in water. If no help given Blue beach lost.

Historical Figure / Narrator (e.g., JFK or Castro quotes) (3:24)

The airstrike has humiliated the United States before. Were you ever offered money to assassinate President Kennedy directly? On numerous occasions. It is clear that the forces of communism are not to be underestimated in Cuba or anywhere else in the world. It's like a nightmare. It's something you think, well, I'll wake up tomorrow and it's not true.

Gordon Carrera (4:02)

We still know too little about the real situation inside Cuba, although we are taking energetic steps to learn more. However, some salient facts are known. It is known that the Communist regime is an active Sino Soviet spearhead in our hemisphere and that communist controls inside Cuba are severe. Also, there's evidence that the repressive measures of the communists together with disappointments in Castro's economic dependency on the communist formula have resulted in an anti regime atmosphere among the Cuban people, which makes the resistance program a distinct and present possibility. Since late November we've been working hard to reorient the operational concepts within the US Government and develop the hard intelligence and operational assets required for success in our task. Americans once ran a successful revolution. It was run from within and succeeded because there was timely and strong political, economic and military help by nations outside who supported our cause. Using this same concept of revolution from within, we must now help the Cuban people to stamp out tyranny and gain their liberty. Well, welcome to the Rest is classified. I'm Gordon Carrera.

David McCloskey (5:14)

And I'm David McCloskey.

Gordon Carrera (5:15)

That was Brigadier General Edward Lansdale writing in a top secret memo for the White House in February 1962 entitled the Cuba Project, which sounds like the title of a kind of one of those sinister conspiracy theory films.

David McCloskey (5:30)

It's a good spy novel title, I.

Gordon Carrera (5:31)

Think it is the Cuba Project.

David McCloskey (5:32)

It's got some legs. Yeah.

Gordon Carrera (5:34)

But we're now in the aftermath of the Bay of Pigs, the kind of fiasco, disaster, whatever other word you can use to talk about it. But it's not the end, is it, of the story of jfk, the CIA, Castro and the kind of battle between those different parties. I mean, if anything, the heat's actually going to get turned up after the US failure.

David McCloskey (5:56)

If you were expecting the Kennedy brothers to just sort of let Castro go after Bay of Pigs and go find some other political problem to deal with. You're wrong. I mean, as we teased at the end of the last episode, I think one of the most impactful consequences of the Bay of Pigs is that the Kennedy brothers, and now it's the brothers, because JFK has pulled Bobby in to essentially run Cuba. At the National Security Council and White House, they are even more committed, bizarrely, to Austin Castro. And it's personal now, I think. You know, I come back to that kind of family cohesion, brotherly loyalty point that their dad had really beat into them when they were young. Although, as we'll see, lots of different bureaucratic elements of the US government will get involved in this next phase of the fight against Castro. But it looks a lot like Kennedy's V. Castro at this point in time. And their attitudes on Cuba haven't really changed after Bay of Pigs. There are National Security Council meetings in the weeks after the Bay of Pigs that show that US Policy is still aimed at the downfall of Castro. Bobby Kennedy is going to set up a new special group, parentheses augmented at the National Security Council to deal specifically with Cuba. And despite the fiasco at Bay of Pigs, I mean, the CIA is still working. The Cuba Target Brigade 2506 might be gone, but the CIA has a commando unit that's got 35 exiles in it. It's got dozens of agents and radio operators that it can infiltrate into Cuba. It's got 26 agents in Cuba, most in Havana, that the agency is in contact with. There's still support to exile groups. They're still running that propaganda unit, Radio Swan, that's pumping CIA kind of written and funded programming onto the airwaves in Cuba. So it's got tools, right, that it can deploy against the Cuban problem. Now there's been a leadership shakeup at CIA. Dulles and Dickie Bissell are over the.

Gordon Carrera (8:02)

Really.

David McCloskey (8:02)

The rest of 1961 shown the door. They're not pushed out right afterward because.

Gordon Carrera (8:08)

That would look too much of an admission of failure, wouldn't it?

David McCloskey (8:10)

And two new characters join us. One, Richard Helms becomes the deputy director for plan, so he takes over Dickie Bissell's slot. Helms will become, in later years, the DCI himself. And then a man named John McCone is made the DCI. Now, McCone is personally close to Bobby. There are great stories about Bobby Kennedy's wife Ethel actually picking John McCone up from Langley on her motor scooter to drive him out to Hickory Hill, this estate that Bobby lived at. Bobby, really, in this part of the story, becomes I would argue a micromanager of the Cuba effort. And keep in mind, Bobby Kennedy is the Attorney General of the United States of America at this stage, but he is interacting, as we'll see, with all kinds of kind of mid level officers of the pentagon and the CIA that are a few steps down from Helms and McCone.

Gordon Carrera (9:10)

Yeah, it's interesting because some of Kennedy's aides, I think Schlesinger particularly writes a memo basically saying we need to kind of clear out the CIA, we need to reform the whole bureaucracy. This whole thing is broken, but the decision is not really to do that. Yes, Dulles and Bissell are gone, but Helms, Angleton, some of these other figures who we hear about who've been involved in Cuba stay and rise up. And yeah, McCone is there, but he feels like he's Kennedy's man who's there, relatively close to him, but it's still the same world. There's not been the shakeup that I think some people felt there should have been or ought to have been at that point. So it's interesting, isn't it, because there is a kind of continuity. And the Kennedys again, opt for continuity rather than radical reform.

David McCloskey (9:53)

No, they, they move high level personnel around. I mean, for example, the, the Cuba task force that Bissell had been running is kind of stood down, but then reconstituted in different parts of the bureaucracy. So the org chart kind of changes, but I think a lot of the mid level players are still there. Right. And nothing massive has really changed.

Gordon Carrera (10:15)

And so now this new leadership is going to be told, basically we want regime change in Cuba, but also specifically go after Castro, isn't it? I mean, that was always, as we'd heard, a kind of priority. But it's, it's going to be even more so now.

David McCloskey (10:28)

And there's going to be two new men who are brought in to lead the Cuba charge that are kind of seen as bringing a fresh perspective on this problem. The first one you read an excerpt from a memo that he wrote to start the episode, Brigadier General Edward Lansdale. And by the way, tip of the cap here to Max Boot's wonderful book the Road, Not Edward Lansdale and the American Tragedy in Vietnam. He's got some just exceptional stuff in there on Lansdale's experience with respect to Cuba here, which is remarkable. So Lansdale is a supposed expert on guerrilla warfare techniques. He's alleged wrongly to be the model for the protagonist in the Quiet American, the Graham Greene novel. Fantastic novel, fantastic novel. But rightly, he is the Inspiration for one of the few positive characters in the Ugly American. So Lansdale is kind of a notorious figure. He's got a reputation as a can do covert action specialist. He's an advertising exec turned Air force officer turned CIA man. And in the early 50s, he had helped to mastermind the defeat of a Communist uprising in the Philippines. And then he was in Saigon in 1954. So Lansdale is seen as kind of a covert action guy. He's got no experience in Cuba. The Kennedys, Bobby, see this as an asset. So he's kind of bringing in a fresh perspective. He'd not been involved in the Bay of Pigs. And in late 1961, Lansdale is a special operations chief at the Pentagon. He's no longer working for CIA and he is made chief of an interagency task force which comes to be known as the Caribbean Survey Group. And for cover purposes, it's given a much better name, Gordon, which is Operation Mongoose.

Gordon Carrera (12:16)

Good code name. Which is a good code name.

David McCloskey (12:20)

Good code name. It will report directly into Bobby Kennedy's special group augmented at the National Security Council. And the goal is to put as much pressure as possible on Fidel Castro. And what Lansdale does is he produces a wild, pretty detailed, and also, you know, I would argue, kind of thoroughly delusional plan for Cuba in February of 1962. So we're not yet a year away from the Bay of Pigs. This plan is to start in March. It runs over six phases, from gathering intelligence up to guerrilla operations. And then it's supposed to culminate in October of that same year with what Lansdale called the touchdown play, which is the overthrow of Castro by an open revolt. And there's a lot of different elements to this plan. There's eight different sub plans to the different elements of the main plan. And includes things like inserting pathfinder agents, establishing a clandestine headquarters, conducting work, slowdowns, sabotage. And all of this sort of culminates in the overthrow of Fidel. After being briefed on the plan, RFK says that Mongoose is to be the top priority of the US Government. All else is secondary. No time, money, effort or manpower is to be spared. Some of the ideas in Mongoose are run of the mill, like blowing up infrastructure, burning down crops, you know, broader sabotage. All things had been considered before, right? Yeah. How do you destabilize the regime? In one case, actually, a team was inserted into Cuba and then they used Belgian diplomatic pouches to smuggle in spy gear. The team created a network of almost 100 agents that operated through late 1963 helped create supply lines for armed groups. So what we're going to talk about here in a minute is going to show that mongoose kind of goes nowhere. But there are elements of the plan that do come to fruition. And you get the sense in this time period that there's a lot of this activity of, you know, inserting exiles or commando groups into Cuba to conduct raids, to gather intelligence, to sabotage, you know, critical infrastructure. But it's kind of happening slowly and in a little bit of a drip. So by really the Middle of Summer, 1962, the CIA expected that 11 teams would have been inserted into Cuba. But a huge number of the missions have been aborted at sea. Agency operations had managed to only really plant four or so supply caches in Cuba. And they had plans for sabotage. But most of the sabotage that had been carried out by summertime had been sparked by Cuban exiles directly who were kind of freelancing rather than by the CIA.

Gordon Carrera (15:05)

And so that's the kind of, if you like, the more obvious side. But I guess what this period becomes known for is some of the wackier ideas which come out precisely because the mainstream ideas, and clearly not working, not effective, probably not going to work. So you get this sense that people in the CIA are kind of like, hell, what can we do? Maybe partly, what can we do to keep RFK off our backs and show we're doing something? You know, they're just throwing out some of these ideas, which. Some of them are bizarre, aren't they?

David McCloskey (15:32)

Some of them are insane. I do think when we look at this whole stretch of the JFK presidency and Cuba, it's basically a rite of passage for anybody looking at destabilizing the Castro regime or trying to kill him, that you have to come up with an insane idea, and you have to put that idea on paper for the historical record so that now we can look back on it and talk about what a lunatic you are. And Lansdale, he undergoes this rite of passage just like everyone else does. So on October 15th of 1962, I think, to your point, Gordon, realizing that a lot of the sort of mainstream stuff is just not really working, Lansdale writes a memorandum titled Illumination by Submarine, and it proposes firing star shells from a submarine to illuminate the Havana area After dark on 2 November, critical date, which is All Souls Day, in order to, quote, gain extra impact from Cuban superstitions. Now, the memo, contrary to the popular lore on this, which argued that the net effect of this would be to convince Castro and the Cuban population that this was the second coming of Christ. That's not actually what Lansdale was intending to accomplish, but the memo does suggest that the star shells could be coupled with a CIA generated rumor inside Cuba about mysterious portents signifying the downfall of the Castro regime and the growing virility and strength of the resistance. When this idea came out over a decade later in the church pike earrings, it was mocked as elimination by illumination.

Gordon Carrera (17:14)

I mean, it is a bit almost medieval when they used to think that a comet was a kind of portending some doom for your king or your country. If you saw it overhead in those days. I mean, it sounds pretty desperate to me. Although we should say they'd already done some pretty desperate stuff already. I mean, we've heard previously that we've had the poison cigars, drugs and things and diving suits for fungus. So, I mean, I just get the feeling these people inside this area are kind of spitballing, well, what can we do? We could do this, we could do that.

David McCloskey (17:41)

And I will share with you without giving away any of the details of which country I'm talking about a very similar experience I had almost 60 years later when I'm working at the CIA and there's a covert action program that is targeting an unspecified country. And we had written a paper on the pillars of support that this particular regime enjoyed. And the tasking that came to us was, doesn't matter how crazy the idea, give us a list of all of the different things we could do that would chip away at these pillars of support. Don't censor yourself, just write everything down. And so we came up with dozens of ideas, many of which were insane.

Gordon Carrera (18:29)

You're obviously not going to share any of those details.

David McCloskey (18:31)

No, I'm not going to share any of the details. But I mean, as we're writing it, it's like some of these are bonkers.

Gordon Carrera (18:36)

It's pub talk, as we'd call it here.

David McCloskey (18:38)

The request is to be comprehensive and to not, not let the risk or, you know, frankly, even just the, the appropriateness of an idea get in the way. So this is a long standing CIA tradition, obviously, and I mean some of.

Gordon Carrera (18:55)

The ideas here of Mongoose, I mean, just, just to run through some of them. Operation Freeride. Create unrest and dissension among the Cuban people by airdropping valid Pan Am or KLM one way airline tickets good for passage to Mexico City or Caracas. I mean, giving people free airline ticket. I mean, I guess, you know, saying you can get out of the country. I mean, quite expensive, but also, I just don't see why how that's going to work. I mean, Operation Good Times. Disillusion the Cuban population with the Castro image by distribution of fake photographic material, such as an obese Castro with two beauties in any situation desired, ostensibly within a room in the Castro residence, lavishly furnished and a table brimming over with the most delectable Cuban food. Airdrop toilet paper into.

David McCloskey (19:46)

That's one of my favorites.

Gordon Carrera (19:47)

Airdrop toilet paper into Cuba with pictures on alternate sheets of Fidel and Khrushchev. I mean, it is slightly childish, it's slightly prank like, but I guess if you're desperate. Desperate times call for desperate measures.

David McCloskey (19:59)

I mean, this one, which would have been real grim, Operation Northwoods, which was to create pretexts that would provide justification for US military intervention in Cuba. And one idea here was having friendly Cubans in Cuban army uniforms attack Guantanamo Bay. There was another one about potentially carrying out a terror campaign in the Miami area that could be blamed on Castro.

Gordon Carrera (20:24)

False flag.

David McCloskey (20:24)

Right. I mean, none of these plans are adopted.

Gordon Carrera (20:26)

Yeah, we should say none of them were adopted. Yeah.

David McCloskey (20:28)

But I think what they do signal is, number one, the immense amount of pressure that's coming down on Mongoose by Bobby Kennedy to just come up with results, to generate results. And the fact that the kind of normal stuff that the CIA would do as part of a covert action program, working with exiles, building up a paramilitary group, propaganda, sabotage, they're not working. Right. It's just not having the desired effect. Now, another character is indeed a character who gets involved in the Cuba effort at this point is at the CIA. He's a renowned case officer named William Harvey, who had been station chief in Berlin and had helped actually mastermind the Berlin Tunnel operation, also had been one.

Gordon Carrera (21:15)

Of the first to spot that Kim Philby might be a bad UN when Philby was in Washington. So he's kind of very interesting character, but also kind of slightly erratic, slightly tricky.

David McCloskey (21:27)

I think it's fair to say he's pear shaped. So if you're picturing a sort of swashbuckling James Bond figure, Bill Harvey is not that, Although he does seem to have the Bond libido. Bill Harvey claims that he slept with a woman every day of his life since he'd been an adolescent. He also carried a gun at all times, which is not common for CIA officers. Now what he starts to run at the CIA is something called Task Force W, which is going to be the kind of revamped Cuba effort. At the agency, he stands up a group called ZR Rifle, which is going to undertake executive action against Castro. And so very interestingly we have this contrast between JFK essentially not authorizing the airstrikes that might have enabled the Bay of Pigs invasion to succeed. Doesn't want to get into overt conflict with Castro, but we're now sort of doubling down on actually killing him. GORDON we have not talked in a while about our Mafia hitmen friends who had been dispatched to go after Castro. Right now, Bill Harvey, in kind of the spring, summer of 1961, he takes over that portfolio in his running. If you recall, our Mafia friends were Handsome Johnny Roselli, Sam Giancana of the Chicago outfit. And they were being essentially run by a guy named Bob Mayhew, who was a former FBI agent who the CIA used for sort of odd and sometimes sleazy jobs.

Gordon Carrera (22:59)

And I can imagine Harvey being just the right man for this because he's more like them than anyone else. I mean, he kind of looks and feels a bit Tony Soprano. Bill Harvey So I think he's going to get on quite well with these gangsters, which is perhaps again going to lead to some of the conspiracy theories which will come later on down the line.

David McCloskey (23:16)

One of the first things that Bill Harvey does is he looks at the interaction with the mobsters. And I mean, plotting had kind of been stalled since the first failed effort to deliver poison pills to an anti Castro agent in Cuba. Now Harvey looks at this and says, okay, I want Sam Giancana out of the picture. You remember, Sam Giancana has a big mouth and also had convinced the agency to help him bug a hotel room to see if his girlfriend was cheating on him and gotten the CIA and some hot water with the FBI. So Bill Harvey says, this guy's a liability. There's another mobster involved named Santo Trafficante who is a drug runner. But that's not the only reason he's fallen out of the agency's favor. And it's because he's actually suspected of maybe sabotaging that earlier poison pill attempt. Or perhaps more worrisome, that the agent to whom those pills were passed was in fact a double and working for Castro. And so this whole network under Trafficante is sort of suspect. And what happens is that the mob effort is essentially whittled down to Handsome Johnny Roselli. And they hatch another plan. Gordon and do you know what it is?

Gordon Carrera (24:27)

It is poison pill.

David McCloskey (24:28)

It is, it is the exact same plan as the one they hatched before. And the idea is that again, The CIA will deliver poison pills that a band named Tony Verona, who's part of this exile group in Miami. Tony Verona will run those poison pills to a contact in Havana who works at one of Castro's favorite restaurants. And in exchange, Tony Verona's group wants guns and money. So Bill Harvey and the CISG was stationed in Miami, fill a U haul trailer with $5,000 worth of explosives, detonators, 30 caliber rifles, 45 caliber handguns, radios, they leave it all parked in the U Haul at a drive in restaurant in Miami. Verona's people pick it up and those pills will eventually find their way into Havana. Now Roselli is pulled deeper into the work by Bill Harvey. And it seems that Roselli and Bill Harvey get along really well. Actually. There's like a mutual respect between them. Essentially Roselli, who is a member of the Mafia, is tapped by Harvey to help organize Cuban exile kind of commando and gun running missions into Cuba, oftentimes outside the purview of the station in Miami. And this is a period where there are just wild stories of near miss assassination attempts against Fidel. In one case, Roselli prepares a team who had allegedly nearly assassinated Castro at a Havana intersection in September of 1961. That team's rolled up and captured and executed. In another case, a team is infiltrated into Cuba with the idea that they will fire rocket propelled grenades at Castro when he appears during a public ceremony. But there's problems with the weapons and they're arrested. And then back to the poison pills. In Another case in 1963, one of Verona's, Tony Verona's assets, who's a waiter in Havana at one of Castro's favorite haunts, the Hotel Havana Libre, is working when Fidel shows up and orders a chocolate shake. Now, the asset apparently has one of the poison pills hidden in the freezer of the restaurant in kind of a back panel. But the pill had frozen to the metal siding. And when the waiter is trying to claw the pill off so he can put it into the, the shake, it bursts open and is, is totally useless. So again, we have just failed assassination attempt after failed assassination attempt. All the while the CIA's effort against Cuba is, is getting huge. I mean, this is a period where the CIA station in Miami is probably one of the largest in the world. And there are so many boats ferrying agents and supplies into Cuba that the agency may have controlled the third largest navy in the Caribbean at that period of time. But despite all of this activity, By October of 1962, Mongoose and the CIS Task Force W under Bill Harvey have fallen well short of expectations. They're putting together kind of lists of targets to hit inside Cuba. They're compiling a target list, but really not much has actually happened.

Gordon Carrera (27:46)

And there, I think, is a perfect moment to take a break because in October 1962, something else is going to happen in Cuba, which is going to be very important when it comes to JFK's presidency. So let's take a break and after that we'll look at the last months, really of JFK's presidency leading up to his death. See you after the break.

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Gordon Carrera (29:51)

Now, welcome back. We left things in October 1962 and of course that is a, you know.

David McCloskey (30:03)

Big month in world. What happens, Gordon?

Gordon Carrera (30:06)

Something called the Cuban Missile Crisis. Now I should say, in case you're wondering how we're going to kind of squeeze that in into the last of a six part series we're going to.

David McCloskey (30:13)

Do it in 15 minutes.

Gordon Carrera (30:14)

Let's do it. 10 second summary. Some missile. No, we're not going to do it in 10 seconds because I think it's worth its own series, particularly because it intersects with some really interesting spy stories about Penkovsky and about imagery, intelligence and things like that. But, you know, the crucial point is October 62, US intelligence. U2 spy planes detect the fact that the Soviet Union looks to be putting missiles onto the island of Cuba. And this is going to cause one of the great crises of the Cold War, isn't it? Because President Kennedy is going to have to decide what to do about it, how far to go to confront the Soviet Union about these missiles. The fear being, of course, that they are nuclear tipped missiles which are going to be close to the United States. And that is something which he's not willing to tolerate. And it's very interesting, I think, because he learns quite a lot from Bay of Pigs. And one of the things that I think he learns is not necessarily to listen to people like the CIA and the military, because I think he feels that was my mistake that time round. And of course, when it comes to the Cuban Missile Crisis, the military particularly are saying, let's go to war, let's invade Cuba, let's go to war. Some of them are basically thinking, let's just get on with this whole World War three thing with the Soviet Union, because we've got to do it. And Kennedy, actually, you can see him having grown from the experience, I think, of Bay of Pigs in the way he handles the Cuban Missile Crisis. And I think it's really interesting because, you know, he could have taken that opportunity to basically do what he wants to do, which is get rid of Castro. And there are definitely people wanting him to do that, but he's learned to be skeptical and back away from the most aggressive option and think quite carefully. So he learns. And, you know, it's emblematic of a person who suddenly put the right structures and right systems in place to handle a crisis. And it comes through very well. But of course it does leave this issue of Cuba unresolved.

David McCloskey (32:03)

But it does have a very significant impact on how the Kennedy administration pursues its goal of eliminating Castro. Because those U2 reconnaissance flights, they showed not just missiles, but actually a massive Soviet military buildup on the island. Aircraft, thousands of troops. Much later, historians will learn that the number was like 40,000 Soviet troops. So all of a sudden, the risk of military or covert action adventures in Cuba has gone way up from the perspective of The White House. So every commando mission, every act of sabotage could result in direct conflict with the Russians, in theory. And on the 29th of October. So this is in the middle of the missile crisis. RFK goes to Mongoose, goes to the CIA and basically says, shut down the Cuba operations. Like, I don't. I don't want there to be any commando missions or infiltrations done anymore. And I think the Russian presence there and the kind of sense of a near miss in the missile crisis, what it does is I think it drives the Kennedys to actually kind of look even more closely at executive action or assassination targeting Castro rather than this broader effort to kind of sabotage the island or to run exiles or commando raids in that might potentially hit the Russians.

Gordon Carrera (33:28)

A more targeted option is better, but it also leads to a massive row with Bill Harvey, doesn't it? Which I think is very, very interesting, because they're worried during the Cuban Missile crisis of CIA covert action kind of triggering a war or undermining the policy. And Bill Harvey is basically kind of still, still going at it.

David McCloskey (33:48)

Well, Bill Harvey sends a team in during the missile crisis, which is nuts. Which is nuts.

Gordon Carrera (33:54)

And against orders.

David McCloskey (33:56)

Harvey had approved an infiltration operation during.

Gordon Carrera (33:59)

The Cuba missile crisis.

David McCloskey (34:01)

And when RFK finds that out, I mean, he goes absolutely nuts. And it's also, I think, the case that there was kind of simmering personal beef between RFK and Harvey that had been building up. There's a story about how the year before RFK had actually been stopped by Harvey when he was walking out of the. Out of a room with a classified CIA cable. And Harvey tells him, basically, give that back to me. So there's like a personal beef here. I also think that Bill Harvey looked back at Bay of Pigs and said Kennedys were responsible for this. There's sort of an actual verbal altercation between Bill Harvey and RFK over the Bay of Pigs. That leads McCone, who's the head of the CIA, basically, to say, look, Harvey has destroyed himself today. His usefulness has ended. So Bill Harvey gets sent to Rome, although he does meet one more time with Handsome Johnny Roselli in January of 63. It's a little murky because he pays Rosselli to defray some of his expenses. And then a few weeks later, Harvey tells Handsome Johnny that, look, the operation against Castro is terminated, but this bounty, this $150,000 bounty is still in place. So what seems to have happened in this kind of Mafia stream is that throughout 1963, there's probably something like an open contract on Castro that the mob has put out there that's well known inside the Cuban exile community in Miami. So even if the CIA isn't pulling the strings, there's kind of an outstanding mob reward if someone could pull it off.

Gordon Carrera (35:38)

Yeah, and it's also worth just saying, you know, Bill Harvey, who has this massive falling out with the Kennedy White House, blames them for the Bay of Pigs. He clearly leaves with a grievance and a gun. And one of the kind of tracks of the theories around the conspiracy, around the Kennedy assassination will involve Harvey. Actually, the people who do believe that the CIA might have been responsible people will point to Harvey as a man who had this kind of real bitterness towards the Kennedys and who felt they'd let the CIA down and who's been moved out of his job and has contacts with the mob. So you can see why he becomes part of the kind of folklore of around what might have happened there.

David McCloskey (36:16)

A theory that we will be and are exploring in our exclusive miniseries for declassified club members about these theories surrounding the JFK assassination in Cuba and the.

Gordon Carrera (36:28)

Mob and the CIA. Don't forget the CIA.

David McCloskey (36:30)

I always forget to mention the CIA there, Gordon, for some reason.

Gordon Carrera (36:33)

But meanwhile, back in the run up to the assassination, I guess Harvey is out. He's going to be replaced by someone else, Desmond Fitzgerald. I guess partly because he's more of a RFK man.

David McCloskey (36:44)

Yeah, I mean, RFK is basically making personnel decisions four or five rungs down the ladder at the CIA. So Desmond Fitzgerald takes over the cube effort at CIA. He's a Harvard man, like the Kennedys. Been a lawyer in New York before the Second World War. He's part of this elite kind of Georgetown set of journalists and politicians and CIA men in Washington. Des Fitzgerald sees RFK socially on the weekends. Kind of like Bacone. Like all good Cuba guys at the CIA, he has his own sort of dabbling with lunatic ideas of how you get rid of Castro. Fitzgerald is the one who apparently came up with the, I think now, infamous idea to develop an exploding seashell that would be so attractive that Castro, who was an avid diver, would be sorely tempted to pick it up while he's underwater.

Gordon Carrera (37:32)

This is one of the most stupid ideas. It's no wonder it becomes legendary. How do you know he's going to pick up that particular attractive seashell?

David McCloskey (37:39)

That's the problem, Gordon.

Gordon Carrera (37:40)

Or that some other random diver isn't going to, you know, pick it up and blow themselves up. I mean, that's kind of nuts, isn't it? And what, it's going to be placed by a midget submarine, Is that right? I mean, anyway, I think that's one.

David McCloskey (37:52)

Of the other problems. You have to. You have to. A midget submarine has to get very close to the Cuban shore to deposit the seashell, and you have no idea who else is going to pick it up. Also, how do you design a seashell that's just unbelievably attractive, such that Fidel could not help but pick it up? Anyway, lots of problems. That idea is abandoned.

Gordon Carrera (38:10)

So more ideas on assassination and more ideas on sabotage as well, I guess, to try and kind of keep the momentum going.

David McCloskey (38:16)

That's right. In the spring of 63, the CIA is kind of getting, I think, fed up with these commando raids that the exiles are running. It's kind of seen as a way to pump up the exiles, but it's having really no impact inside Cuba. And it, again, runs the risk of direct conflict with the Russians. So In April of 1963, JFK asks for the CIA to go back and come up with an updated sabotage plan. So we get some sense here of, like, it's the definition of crazy. You just kind of keep doing the same things over and over again, you know, expecting different results and getting the same one. Kennedy's go back. Let's. Let's try sabotage. So Des Fitzgerald works up a plan over the summer. In June, he presents his proposal to jfk. The sabotage plan would be targeted at four different segments of the Cuban economy. Electric power, oil refineries, railroads, and highways, manufacturing. The program was designed to kind of interlock with efforts by the exiles to keep conducting these raids. And interestingly, though, Gordon, there's a question at this meeting about whether the Cubans might retaliate in kind. And this seems to be maybe the first or one of the first times that the possibility of any Cuban retaliation appears in notes of discussions at the National Security Council level, which, again, when you're talking about different theories around the assassination, I mean, this is the middle of, you know, 1963. We're just. We're months away from John F. Kennedy's assassination. Where's that coming from? You know, the Cubans started to think about how do we make the Americans pay a price for everything they're doing on that.

Gordon Carrera (39:48)

Yeah, and they've tried to do some things, haven't they, the Cubans? I mean, in 1962, I think Castro dispatches some agents to New York to carry out some bombings targeting the Statue of Liberty and Grand Central Station. They get caught by the FBI but it does show that Castro wants to do something, which again feeds into one of the theories around jfk. He knows that they're trying to kill him, there's no doubt about that. So it's not implausible to think he might want to return the favour.

David McCloskey (40:15)

One of the other threads here in the last months of JFK's life is that Dez Fitzgerald and the CIA are looking for an asset close to Castro who might be willing to help kill him and then to maybe instigate a coup. Right. So there is an effort in the fall or the autumn, as you would be fond of saying, Gordon, to kind of look at the Cuban military, the upper echelons of the Cuban military, and evaluate each of those personalities for suitability as a recruitment target. And the agency looks through maybe 150 potential recruits. It's in contact with a very small number of them, maybe three or four. And one of those is a Cuban major named Rolando Cubela Sequedes, who will get the kryptonym Am Lash AM is the digraph for Cuba, for Cuban assets back in those days. Now Cubella, he's a prominent Cuban who had been a communist, he'd actually been a player in the revolution. He was responsible for killing the deposed dictator, Batista's director of military intelligence. But Cubella has had a falling out with Castro and he has met with CIA handlers off and on and always outside of Cuba. Since 1961, he's considered defecting. He's gone back into Cuba for periods of time and been incommunicado, he's refused a polygraph, he's really hot headed and very mercurial. So he's not a great asset from the standpoint of having any kind of control over him. What the CIA had tried to set him up with from a commo standpoint was the idea that he would have a one way listen radio receiver. Right. And the idea with that is that the agency would send messages into Cuba on the radio, but he would not respond back, which would make it much harder to track the frequencies. He would respond back using secret writing. That combo plan had not actually worked when he was inside Cuba, so he had gone dark. But By September of 63, the CIA has reestablished contact with Cubella and he seems to be warming up to the idea of helping to instigate a coup. But again, in a sign of just how, you know, rough of an asset this guy was to handle, in order to do that, he wants to meet with Bobby Kennedy, which of course is a no Go. So instead, Desmond Fitzgerald flies to Paris to meet him. And of course, the whole idea here is maybe this guy would run a military coup for us, right? And we can handle Castor that way. What Cabello wants is an indication of some kind of, kind of policy support from the Kennedys. He wants weapons, he wants explosives, and he wants a means of protecting himself in a confrontation with Castro or his security forces. Now, there has been endless speculation about whether Cubella was real or whether he was a dangle from Castro in this period. And of course it's fed these conspiracy theories that, you know, Castro knew in the days and weeks running up to JFK's assassination, the CIA was actually trying to instigate a military coup against him. So there's arguments and theories on both sides. But what is clear is that the Agency ends up authorizing a bundle of kind of weapons for Cubella that'll be hidden at a cache inside Cuba. And while DEZ Fitzgerald says, look, we don't want to kill Castro, it's clear that the Agency also seems to be arming Cubella with weapons that he could use in just such a case. And what ends up being delivered to him and worked on by the Technical Services division inside CIA is that Fitzgerald gives to Cubella a poison injecting pen. It's a Papermate pen filled with a poisoned hypodermic syringe. And Cubella has to fill it with Blackley 40, which is this kind of lethal mix of nicotine and pesticide. The CIA report later said that the pen's needle is so fine that the victim would hardly feel it when it was inserted. The pen, Gordon, which the CIA hopes will finally put an end to Fidel Castro, is delivered to Cubella on When else? November 22nd of 1963.

Gordon Carrera (44:30)

A fateful day. I guess that pen has echoes, doesn't it, of the ricin umbrella tip used against Markov in London many years later. You know, as a kind of a device where someone will barely notice that they've been poisoned, but yes. So the pen is delivered to Kabela on that day. And that is of course, what will be the final day of JFK's presidency. November 22, 1963.

David McCloskey (44:55)

That's right. It's a bright, sunny and windy day in Dallas, Texas, where you are now 10 minutes from where I'm recording this. JFK is at the tail end of a four day tour of Texas. He's been to San Antonio, Houston, Fort Worth. He's now in Dallas. After Dallas, he's planning to go on to Austin and then spend the weekend at his Vice President LBJ's East Texas ranch. JFK wakes up that morning in Fort Worth. There's a small rally that he attends across the street from his hotel. He goes to a breakfast and when he returns to his hotel room, his wife Jackie shows him a full page ad in the paper that is highly critical of him. And he makes this famous comment that they're in nut country, which I love, that the city that I now live in is referred to as nut country. And he says that, you know, someone could have assassinated him with a pistol the previous evening. So at 12:30pm, JFK on that bright sunny day is riding in an open top motorcade accompanied by Jackie, the Governor of Texas and the Governor's wife. And they're driving through downtown Dallas. He's headed to a luncheon at the Dallas trademark. The motorcade passes through Dealey Plaza. At that time it's a grassy square surrounded by fountains and concrete pergolas. And there are three shots, although some will say as many as six. With three shots are fired. The first one is a miss. The Second one, about three and a half seconds later, tears through JFK's upper back, between his neck and right shoulder and exits through his neck, hits Governor Connolly. The third, five seconds later, is a straight on shot through the brain. He is rushed to Parkland Hospital and declared dead by 1pm later that day, of course, Lee Harvey Oswald is arrested on suspicion of being the lone gunman who murdered John F. Kennedy. And Gordon, case closed, right?

Gordon Carrera (46:45)

And just three shots, no magic bullet, no grassy knoll.

David McCloskey (46:49)

Well, that's the thing is it's part of the resonance of this entire story today is coming out of the fact that case is absolutely not closed in the minds of most Americans. Case not closed.

Gordon Carrera (47:02)

We'll get into this, obviously much more in the miniseries, some of the theories around it. I think what's so important is if you see that moment of the assassination in, in the context of what has come before, you can start to see where the theories come from because you can start to see, you know, the kind of anger from Cuban exiles. You can see the anger from some parts of the CIA. You can see the anger and the relationship between the CIA and the mob. And you start to see this web which can be woven into a, an idea that it wasn't a low government. And of course, Lee Harvey Oswald as well is such an extraordinary character. I mean, this is someone who has defected to the Soviet Union, who approaches Soviet embassies after redefecting Back to the United States in Mexico City, who's involved in kind of Cuba campaigning in New Orleans. So the kind of overlap between the Cold War, between the Soviet Union, but also between the Cuban issue specifically, is all there in the gunman, Lee Harvey Oswald. So with this kind of context, it's not hard to understand why there will be so much focus on the question of whether it really was a lone government or not. And finally, I mean, the big investigation, the Warren Commission. Who's going to be appointed the Warren Commission?

David McCloskey (48:17)

Oh, I knew you were going to bring this.

Gordon Carrera (48:19)

Alan Dulles, everyone's favorite shadowy spymaster, gets appointed to the commission, which kind of very much wants to say it's a lone gunman. Now, I, I'm not saying it's not a lone government. You know, we'll come to that later. But there's a kind of pressure to not open up the can of worms about all these other things. And there are all these other secrets, you know, about what the CIA has been up to about Cuba, about the mob, about assassination plots which will feed into that. And it's that secrecy which is still only now, you know, with more releases in the recent months being unwrapped.

David McCloskey (48:51)

But I think you can also draw a pretty straight line that begins in this period and includes Bay of Pigs, the zany and oftentimes illegal plotting by the CIA against Castro and the Warren Commission. And you look at those three things and I think the Warren Commission, as we'll talk about in the miniseries, kind of riddled with politics and problems and conspiracies of its own, you can look at those three things and kind of draw a line to say this is a period where prior to this, in the 50s, the 40s, there was a knee jerk trust of institutions and government by most Americans. And after you no longer have that, and you just have to look at the way the CIA is viewed today through the lens of a lot of these kind of activities, or the way the Warren Commission is viewed today. I mean, the official record on the assassination is not trusted by the majority of Americans and at one point in the late 90s was not trusted by 80% of Americans. So this distrust of institutions, this distrust of the political narrative, this distrust of the Central Intelligence Agency, I think we've talked a lot in other episodes of this podcast about the role of the kind of Church pike proceedings in the 70s as being this turning point. But you could make the argument that the seeds of that distrust start in this period under Kennedy and go back to Cuba.

Gordon Carrera (50:29)

I think that is absolutely right. I think, you know, there's a sense in which innocence is lost for America, in which a kind of cynicism and conspiracism takes root because of the kind of psychic shock of having this hugely popular, young, vibrant, virile president murdered in this dramatic way. People are going to want to look for answers. And we know, you know, people will often want to look for reasons behind it. And then, of course, because of this history with the CIA and because of the fact Leo Harvey Oswald has this kind of curious background, there's going to be layers of secrecy which are placed over the story of the assassination and over Lee Harvey Oswald. We had document releases just in the last few months which may have not told us a different answer as to who killed Kennedy, but which certainly kind of reveal, for instance, you know, what the CIA was up to in Latin America in a different way, or what they knew about Lee Harvey Oswald, what they were doing in Mexico City. And of course, all these secrets had been kept because the CIA felt they needed to keep them. But because people knew there were secrets there, that's also fueled the kind of conspiracies which has come out of it. And so we'll have more time, I guess, to explore who we really think did kill Kennedy. But I think this series does give you a feel of why at least a theory that it wasn't a lone government has taken root and just the kind of crazy nature of those times.

David McCloskey (51:49)

I think, and why. And again, we'll discuss this much more in our miniseries for club members, which I would encourage everyone who is listening to this, if they have not already, to go to thereestdisclassified.com, become a club member and listen to that, to that miniseries. Because in the wake of the assassination, Bobby Kennedy asks McCone if the CIA did it. Bobby Kennedy wonders if it could have been the Cubans. So again, he's obviously grief stricken. But at the time, given this history we just talked about, these are not zany ideas. These are hypotheses or suggestions that are held by senior officials in the United States government. Right. I. I do think also the connection between Cuba, Bay of Pigs, Kennedy, the agency, and the deepening involvement of the United States and Vietnam is also an enduring legacy of this time period where when JFK takes office, there are maybe a few hundred American advisors in Vietnam. And by the time he's shot on November 22, 1963, there's over 15,000. So it obviously becomes LBJ's war. But so much of the pivot in many ways to Vietnam. And the focus on Vietnam is a legacy, I think, of the very personal failure that JFK felt at the Bay of Pigs and a desire that you wouldn't have governments in other parts of the world lost to communism on his watch.

Gordon Carrera (53:25)

I mean, just to wrap it up, I think that is why this is such a consequential story, because, you know, it tells you something about the CIA, tells you something about the CIA, and JFK tells you something about America and the American psyche. And it tells you something about international history and Cold War history, whether it's the Cuban missile crisis or the buildup in Vietnam. So many of those things kind of relate back, almost so many of them to the kind of Bay of Pigs and to the failure that takes place there. I think it's a kind of remarkably pivotal and important and kind of consequential event. So it's been a kind of absolutely fascinating series and I think it has opened up my eyes to just how important that event was and the consequences of it. So just a reminder, if you want to hear more, we will be talking about the assassination and how the CIA might have done it, but David Scott and the Cubans and the mob, we're.

David McCloskey (54:17)

Going to look at all the alternatives that connect into this story with the Mooch, amongst others.

Gordon Carrera (54:22)

Yeah, yeah. So do join up if you want to hear that. But otherwise, we'll see you next time.

David McCloskey (54:26)

We'll see you next time.

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