The Rest Is Classified - 92. JFK vs the CIA: Raising Hell in Havana (Ep 3)

Episode Date: October 19, 2025

Upload notice - 20th Oct: Is episode 3 sounding the same as episode 2 on your device? There has been a technical error (since rectified). Please go back to episode 2, clear your downloads, and listen again for the updated version. "Hell, Mr. President, we are involved." That was Admiral Burke's desperate plea to John F. Kennedy as the Bay of Pigs operation was underway. In the days before the April 17th invasion, the CIA's cover story begins to unravel and Castro is aware the invasion is coming. Kennedy, determined to avoid overt US intervention, draws a red line, declaring there will be "no intervention in Cuba by the United States Armed Forces". Join Gordon and David as they detail the critical turning point that doomed the operation. Despite air superiority being absolutely critical to success, Kennedy cancels the essential second round of pre-invasion airstrikes. This single decision means the men of Brigade 2506 must land without controlling the air, turning their ships into sitting ducks for Castro's planes. ------------------- Join The Declassified Club: Start your free trial at ⁠⁠therestisclassified.com⁠⁠ - go deeper into the world of espionage with exclusive Q&As, interviews with top intelligence insiders, quarterly livestreams, ad-free listening, early access to episodes and live show tickets, and weekly deep dives into original spy stories. Members also get curated reading lists, special book discounts, prize draws, and access to our private chat community. To sign up to the free newsletter, go to: ⁠⁠https://mailchi.mp/goalhanger.com/tric-free-newsletter-sign-up⁠ ⁠ ------------------- Order a signed edition of Gordon's latest book, The Spy in the Archive, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠via this link.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Order a signed edition of David's latest book, The Seventh Floor, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠via this link.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ------------------- Email: [e-mail] Twitter: ⁠⁠⁠⁠⁠⁠⁠@triclassified⁠⁠⁠⁠⁠⁠⁠ Video Editor: Nathan Copelin Social Producer: Emma Jackson Producer: Becki Hills Senior Producer: Dom Johnson Exec Producer: Tony Pastor Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Explore the new Peloton Cross-Training Treadplus at OnePeloton.ca. Is it the matcha, or am I this energized from scoring three Sephora holiday gift sets? Definitely the sets. Full size and minis bundled together? What a steal. So cute, it practically wraps itself. And I know I should be giving them away, but I'm keeping the Summer Fridays and Rare Beauty by Selena Gomez.

I don't blame you. The best holiday beauty sets are only at Sephora. Gifts sets from Summer Fridays, Rare Beauty, Way, and more are going fast. Get full-sized favorites and must-have minis, bundled for more value. Shop before they're gone, in-store online at Sephora.ca. From Dallas, Texas, the flash apparently official President Kennedy died at 1 p.m. Central Standard Time. Cuba itself is really quickly going to become the Kennedy administration's top priority. The next four years are going to be difficult and challenging years for us all.

At the end of the day, the U.S. is facing off against this tiny island, Cuba. How could you lose? Castro will tell the General Assembly, the United States is seeking to overthrow him. Kennedy really looks to the CIA to get the business of the Cold War done. dictators, they rule nations, they do not rule people. The CIA were kind of playing JFK. In the eyes of some CIA trained militants, Kennedy had become a traitor to the cause. B-26 bombers of the Cuban Exile Air Force attack Castro's airfield.

Everything that could go wrong does. Out of ammunition, men fighting in water, if no help given, Blue Beach lost. The air strike has humiliated the United States. humiliated the United States before the world. 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. The concept envisages the seizure of a small lodgment on Cuban soil by an all-Cuban amphibious airborne force of about 750 men. The landings will be preceded by a tactical air preparation beginning at dawn of D1 Day. The primary purpose of the air preparation will be to destroy or neutralize all Cuban military air. aircraft and naval vessels, constituting a threat to the invasion force. It's expected that these operations will precipitate a general uprising and cause the revolt of large segments of the Cuban military and militia. The lodgment, it's hoped, will serve as a rallying point

for the thousands who are ready for overt resistance to Castro, but who hesitate to act until they can feel some assurance of success. A general revolt, if one is successfully triggered by our operations may serve to topple the Castro regime within a period of weeks. The question has been raised in some quarters as to whether amphibious airborne operation could not be mounted without tactical air preparation or support or with minimal air support. It is axiomatic in amphibious operations that control of air and sea is absolutely required. The Cuban Air Force and naval vessels capable of opposing our landing must be knocked out or neutralised before our amphibious shipping makes its final run into the beach.

If this is not done, we will be courting disaster. Well, welcome to the rest is classified. I'm Gordon Carrera. And I'm David McCloskey. And that was a CIA-Cuba Task Force memo from January 1960 planning what will become known as the Bay of Pigs. David, one of the great disasters for the CIA, which will define. the relationship of the CIA with President Kennedy, and as the more conspiratorially minded out there might believe, actually lead even to his assassination in 1963. That is the story we're on, the journey we're on. We left last time with John F. Kennedy just being elected president

in 1960, inheriting Eisenhower's Cuba policy, which is regime change, but done very quietly. It's so easy to overthrow regimes quietly, Gordon. I can't believe it didn't work. I also note for our listeners that if you're not watching the video and if you were sort of not totally engaged with Gordon's tone in what he just said, that Gordon has taken, I would say, a disturbing amount of pleasure. Every time you mention this is a failure for the CIA, you seem quite energized. I'll just point that out. I'm not making, I'm not exactly, I'm not saying why. I'm just noting that you seem quite excited by this failure. And as your cousin across the Atlantic, deeply disturbing, let's just say.

Well, I could only apologize, but I just think it's a chance to show that the CIA isn't perfect. There's not many stories we can share about the CIA not being perfect, so we've found one. But also, you know, as we discussed in previous episodes, I haven't gone entirely down the rabbit hole. My head is kind of peeking out of the rabbit hole. I'm kind of half in, half out of the rabbit hole of kind of CIA conspiracy land on this one. So I stand ready to be persuaded that the CIA was all sweetness and light in this story. And we should note, Gordon, for our listeners, that we are in the middle of a very special exclusive miniseries that is connected to the story we're telling here, that looks at how different parties in this story,

be it Castro and the Cubans or the CIA or the mob, may have had motive to kill President Kennedy. we're kind of looking at the theories about their involvement in his assassination, which is where you sort of more fully go down the rabbit hole. But maybe you can share here, your working hypothesis from your sort of tinfoil hatland has been that the story that we're about to share gives the CIA potentially some motive to assassinate President Kennedy. Is that right? Yeah.

Let me present it as the view of others rather than necessarily my own view. Let me give myself a little bit of distance from the tinfoil hat. But the story of what goes wrong with Bay of Pigs, and particularly what we're really focusing in on, is the relationship between a kind of COVID action and a politician authorising it, which in this case, without giving too much away, it doesn't go very well. Whether that leads to a degree of anger and a desire for revenge, which could at least give you a motive for murder, that is the claim that's made by some. By some, not necessarily Gordon Carrera. And we would encourage listeners if you haven't already, go to the rest is classified.com, sign up for the declassified club. You get access to that mini-series and listen to Gordon not framing that view as the opinion of others, but really claiming it as his own. So let's see where that view comes from because we left last time with John F. Kennedy having taken over the presidency.

it is January of 1961, and within days really of his election even, I mean, prior to him taking office during the transition, JFK announces that who else, friend of the pod, but Alan Dulles is going to stay on as the director of the CIA. And this is already quite an interesting moment, isn't it? Because I think some of his aides try and persuade him that he should clear house, both in the FBI and get rid of J. Edgar Hoover and get rid of Alan Dulles at the CIA and have a fresh start without the kind of baggage that comes from these two heavily invested spy chiefs,

these quite dominating figures over their agencies. And he doesn't do it. And I think there are interesting questions as to why he doesn't do it. I mean, one is perhaps he's only won a narrow victory in that election. He doesn't necessarily feel he's got the political capital to kind of clear house in that way.

Others have suggested that Poova, but maybe even Dulles, knew quite a lot about Kennedy and the Kennedy family and some of the predilections and other things, and that would it be too difficult to take on these power centers? But anyway, the result is he's going to keep them on, and I think that is going to shape part of his presidency. It was also, I mean, I think a less partisan time in Washington, and Dulles had served a Republican. He served Eisenhower as the director of Central Intelligence, but it wasn't an automatic thing as it is now to switch over

your entire national security team. So there's also that piece of it. Also, I mean, Dulles and Kennedy knew each other socially. I'm not sure I would call them friends necessarily, but they were definitely friendly with each other. In fact, Jackie Kennedy had gifted Alan Dulles a copy of Ian Fleming's Bond novel from Russia with Love, thinking that the spy chief would love it, which of course, he did. And he did. Yeah, he did. So I think Dulles is perhaps a little taken with the Kennedys. I think Kennedy himself is a little bit taken with CIA. I mean, And I think Kennedy, in now this 60 plus years on, we've kind of come and interpreted the story and say, oh, you know, JFK had this kind of sour view of the Central Intelligence Agency. But when he takes office, I think it's not the case at all.

I think JFK and his brother Bobby, they love the Bond novels. I think they see the CIA guys as being these kind of swashbuckling, cold warriors. We introduced a character named Dickie Bissell, Richard Bissell, who's the deputy director for plans at the CIA. head of covert action. I think they see, the Kennedy's seeing guys like Bissell and Dulles, these kind of high character, smart, adventurous guys that fit in with the New Frontier, Kennedy's New Frontier perfectly. Bissell had actually described himself as a man-eating shark to the Kennedys during the transition, which apparently the Kennedys are absolutely delighted with. And you can see Kennedy's sort of fascination with the Central Intelligence Agency and the

numbers. I mean, over his three years in office, Kennedy is going to approve 163 major covert action programs. Eisenhower did 170 and eight years in the office. So I think Kennedy really looks to the CIA to get the business of the Cold War done. So on November 18th, just, you know, a few days after the election, Dulles and Dickie Bissell, travel down to Palm Beach. They're carrying big folders with maps, and they briefed Kennedy on their covert action plan to essentially invade Cuba. And Dulles will claim that this is really the first time that Kennedy had ever been briefed on the operation. Now, of course, last time you raised the idea that in July, Dulles may have briefed candidate Kennedy with some detail on this operation.

Yeah, that's what Nixon certainly believed. That's what Nixon believed. But Dulles will stick to the line that Kennedy hadn't heard any of the details before November. And inside CIA Gordon, this Cuba task force that's operating in the Western Hemisphere Division is getting considerably larger, too. I mean, it's gone from 50 people-ish in March of 1959 to over 300 dedicated positions inside CIA when Kennedy takes over. So bureaucratically, it's growing. And Cuba itself is really quickly going to become the Kennedy administration's top priority. And it's really going to start to crowd out almost everything else from his plate in those first few months. I think Kennedy has kind of

made the jump that a lot of Americans have made when they look at Cuba. I think in 1958-59 as a kind of as a senator on the Foreign Relations Committee, Kennedy is almost sympathetic in some ways to Castro's revolution against the Batista regime. But by 1960, during the campaign, as we saw, and certainly by the time he takes office, Kennedy has, I think, come to the conclusion that Castro is a communist and that he, President Kennedy, needs to do what is required to prevent Castro from consolidating his regime, spreading his revolution throughout Latin America. And so Kennedy, I think he signs on to this view of the Eisenhower administration that the policy of the United States should be regime change in Cuba. So where do preparations stand on this Cuba task force in the days before

JFK takes office? So Cuban crews, the Brigade 2506, the exile paramilitary group that will be leading the charge of the invasion, their training to operate the landing craft that will be used to transport them to Cuba's shores. But in many respects, the planning or the preparations are going more slowly than CIA would like. 10 B26 bombers have been procured, but only five Cuban pilots at this point are capable of flying the planes. The brigade, that brigade 2506, is undergoing rigorous training at its camp in Guatemala, but only 500 men have been successfully recruited. And the CIA envisions a force in maybe the low thousands, right? So they're sort of lagging from a manpower standpoint.

And as you read in that opening quote, Gordon, the idea that is jelling in early 1961 is that this group of paramilitary exiles will hold a strip of territory inside Cuba. So they won't just be infiltrated clandestinely. They'll hold that lodgment, that beachhead, and then use that as kind of. of a toehold to hopefully instigate a broader uprising or even a military coup in Havana. That's the bit which seems to me where things start to look a bit wobbly in terms of a plan. I mean, because I feel like this has got echoes for me of even some of the kind of crazy talk before the Iraq war in 2003. Not actually in that case from the CIA, but more from people around the Pentagon who were like, yeah, well, just drop in some Iraqi exiles. Ahmed Chalabee's friends, you know, as it was then, the kind of this.

Iraqi opposition group, and everyone hates Saddam so much. The regime is a house of cards. It'll just fall apart. And this kind of ability to underestimate the strength of regimes and the ease with which they will just collapse with a little kind of prod. And I think one of the problems here is I think I'm right in saying that directorate of plan, so the operational bit of the CIA, was obviously running this. But the Directorate of Intelligence, the McCloskey's, the analysts, they weren't being asked, how strong is the Castro regime, how stable is it, how much support is there? Because actually, there was quite a bit of support for Castro. Yeah, I think the stove piping between the analysts and the operations folks, which frankly

was a problem even when I was working at the agency, is much more of a problem in the 1950s and 1960s. I mean, you could essentially think of the analysts and the operations people as being entirely separate organizations at this point in time. I also think that, you know, when you look at the national intelligence estimates from this period, you're not getting a particularly rosy picture of the prospects for regime change in Havana. I think what the operations people, what Dickie Bissell will be banking on here, well, really two things. One is you don't know what happens until you try it, right? Which is a bit of, I mean, it's true. If you invade part of Cuba and hold it, who knows what happens, right? The other piece of this is the CIA has,

has been told by the president that the policy of the United States is regime change. So you are trying to come up with the best possible plan under really tough circumstances to affect that outcome. And it kind of doesn't matter what the analysts say. That's the policy. So there'll be a lot in this story where we can't really defend what the CIA does, but I do think in these kind of programs. And again, I think to Syria, you are stuck in a position of the policymakers have decided. I mean, on Syria, you know, Obama said, well, Assad must step aside. So the policy of the United States becomes regime change, effectively. Assad is not the legitimate president of Syria.

Well, what do you do to accomplish that? I mean, it kind of doesn't matter at that point. If the analysts are saying, well, Assad's got a bunch of staying power, you've been handed a covert action program. You've been handed the guidance for the White House to do something and you have to do it. But it's interesting here, isn't it? Because the Pentagon are going to get brought into the planning. for a Cuba operation. And they're going to look at it and go, you're facing a much bigger military. So if you're going to do this, you need a much bigger force than the kind of

the few hundred that the CIA's got. They're not ready yet, are they? They haven't got the manpower. Yeah. And the Pentagon had tapped a kind of liaison to the CIA task force who did look at this and said, you probably would need 5,000 men to hold a lodgment of kind of appreciable size with an airstrip. Because Castro has a gigantic militia, several hundred thousand strong. And then he has an army that's at least got 30,000 men in it. So Castro can, over time, throw a lot of resources at you. 500, 700 exiles isn't really going to cut it. It's also clear from the memos at this point in time, including those that are briefed at the White House, that the CIA and the Pentagon agrees with this are absolutely

crystal clear, that whatever size the paramilitary force might be, it requires. aerial dominance of the beachhead. And we'll come back to that, because that's going to be a key part of the story, isn't it? So at this point, the CIA basically being told you've got to grow this force. You've got to kind of build up your paramilitary group to be at least a bit bigger to have any chance against the Cubans. That's right. And part of this effort is happening in Guatemala.

There's another training base that is opened in Nicaragua. The code name is Happy Valley, not a super happy place. definite prison vibes at Happy Valley. It's surrounded by razor wire. It does have a runway. It's a facility that had been built by the United States in the Second World War to defend the Panama Canal. It's got a structure with a sign over the door that reads bar. So there's a bar on the base in Happy Valley. The shower at Happy Valley is a horizontal pipe over a wooden platform that just kind of leaks water out. It has a latrine, which is a lime-coated trench covered with a wooden plank. It is infested with scorpions.

One soldier actually has to be airlifted back to Florida for medical treatment after being stung by a scorpion in the shower. And despite all of that awfulness, it's actually not a bad place to stage a kind of semi-clandestine invasion of Cuba because it's 550 or so miles south of Ivana. It is far enough from Castro to avoid raising obvious suspicions, but it is just within range of a B-26 outfit. with auxiliary fuel tank. So it's kind of going to become the staging point for the invasion and ultimately where the small exile air force will operate from. But tensions are running pretty high at the camp, so high in fact that just as Kennedy is taking office in January of 61, a few hundred of those very precious exile brigade members abruptly resign. A lot of these guys are not trained soldiers. They're living in this extremely rustic camp, being prepared to go on

something that's maybe not quite a suicide mission, but getting pretty close to it. And you can imagine how you wouldn't, over time, want to stay there for much longer. They eventually convince most of these guys who wanted to leave to stay. A few dozen of the most troublesome are actually flown to a prison in the Guatemalan jungle, where they'll sit out the invasion. And if you're the CIA looking at this, right? Because this is just as JFK is taking over. I mean, in one light, this is a major problem, because if you have an exile brigade that's only several hundred strong, and a few hundred of them have basically set out, we'd prefer to not be here. Number one, your force isn't that cohesive. Number two, how in the world, if you can't get these people to agree on anything,

will you get six billion Cubans to agree that once these guys invade, they should be supported, right? But this is really important. Dulles and Dickie Bissell draw the exact opposite lesson from this kind of semi-mutiny, which is we need to move faster before this whole thing falls apart. Which is kind of interesting, isn't there? That's an interesting lesson to take because they basically say this thing has a shelf life now and we have to move quickly. Yeah, I find that really interesting. They're struggling with recruits. They're losing people. And instead, they're kind of like, let's not rethink the plan, heaven forbid, or do something different. But I guess the question is, why the urgency?

Why the pressure? I mean, you'd think at that point you could go, let's rethink this, let's do this properly. But instead, it seems like momentum, maybe. Yeah. Well, also, agency is being asked, told that it is going to be the primary action arm of the president to conduct this covert action to achieve U.S. policy. this is the best asset that the CIA has to accomplish that. And if this thing goes away, the CIA will have very little left. And so what it compels the agency to do is to basically water down the selection criteria for the brigade.

The agency had been pretty choosy prior to this about who actually got into the brigade. They got polygraphed. They did some rudimentary background investigation. They did a psych exam. They tested their IQ. it seems like in kind of January, February, 1961, the selection criteria get a little bit weaker, right? Because they need to add more men. And what happens as a result of that is that 900 more are added to the roles between January and mid-April.

So you have more people, which is good. But you also have people now who more of the brigade doesn't have any military experience, right? you have more doctors and lawyers who get added. You have more married men. They're a little bit older. So a lot of these guys are obviously, they've got a bit of a clock on them in terms of their willingness to go sit in a Guatemalan jungle at a training camp. Also in 1961 in January, the CI brings in former Special Forces officers to work with the Cubans to kind of train them and to get really the kind of exile navy set up that will ship them to Cuba. for the invasion. So what we see is this kind of building urgency inside the CIA, but urgency is

also building inside JFK's national security team, so the policymakers. And just days after the inauguration, Dulles tells JFK that, look, we've really got like two months before something needs to be done about the Cubans that were training in Guatemala. And I think there's a couple reasons for this urgency. I mean, one is that Castro's grip on Cuba is getting much tighter. I think from the scene from the agency, there's a kind of closing window to affect any kind of political change in Havana. A second point, and really a big one, is that the CIA has intelligence that arms shipments will very soon be arriving in Cuba from the Soviet bloc, which is going to make the Castro regime a far more formidable foe, right? So at this point in time, Castro is kind of

operating a banana republic level, Navy, Air Force, Army, and that's going to change, right? So by the end of April, the CIA thinks, the Cubans will have more tanks, more artillery pieces, more small arms, and really important, 41 Soviet megs, so fighter aircraft, are just months away from being operational and Cuban pilots have been sent

to Czechoslovakia to learn how to fly the jets and to train. So you're seeing, like, the military picture is going to change considerably by the time you get to the end of April. And also, I mean, a bit pedantically,

I guess, but important for the invasion, the rainy season in Cuba begins in April, and you'd prefer to not conduct an amphibious invasion in the middle of hurricanes and rainstorms. Yeah. So you've got a picture of kind of momentum building, this force being built up, a slight sense of kind of use it or lose it to that force, that there is this narrow window and a window which is closing.

But how much do you think JFK realizes that this plan is a little bit tenuous? I mean, he's going to ask for evaluations of it. So you get a sense he is asking the questions. that you want a policymaker to ask. I guess one of the questions I have is whether he's really told the truth. And I mean, we'll get to the kind of chance of success later. But it does feel like just the momentum is driving them onwards at this point. I do think these kind of programs have their own momentum that becomes an actual reason for it to continue.

It's just that it's already going. You know, and no one wants to be the one to kill it. I think that's at play here with Kennedy. Jim Razzenberger, in his wonderful history of the Bay of Pigs, makes the comments in several places in that book, again, which I'd really commend to listeners, that JFK's engagement with the planning process was shallow, that he wasn't asking very penetrating questions about the operation. And I think really it's actually more of a commentary on Mack Bundy, his national security advisor, the national security advisor is supposed to represent

the president on foreign policy and make sure that the president's interests are protected both from the standpoint of geopolitics and national security, but also from the standpoint of politics, domestic politics. And the policy process in this case, I think, was abysmal in that in a lot of these meetings, JFK is actually just not prepared, I think. And so you you end up with a shallow engagement with the topic and I think with inability on the part of the president to ask deep questions. The flip side of that is that I think because there's so much that the CIA is presenting, I think there are pieces of the operation and in particular critical aspects like when the battlefield will be prepared with airstrikes that Bissell and Dulles

don't communicate effectively to the president. I guess that's the question is you can say yeah, Kennedy's team, they're a bit more informal, they're fresh, they're maybe not asking the right questions. But you do wonder, and I do wonder, whether Dulles and others were really giving them the kind of detail briefing that they might have needed. The Pentagon are going to give an evaluation, aren't they, on the CIA plan, and they're going to say, you know, it's contingent on local support, the amphibious support should be successful. There's a lot of kind of might-be should-bees in it. There's a line in it. The Joint Chiefs of Staffs consider that timely execution of this plan has a fair chance of ultimate success, even if it does not achieve immediately

the fuller results desired and could contribute to the eventual overthrow of the Castro regime. So what does fair mean, right? What's fair? Yeah, and that is the really interesting one because fair, intelligence speak, is pretty low, isn't it? Isn't fair like a 30% chance of success? Well, later on, that's what this, because this report is authored by the Pentagon kind of

liaison to the CIA task force. And later, he will say that fair meant exactly a 30% chance of success. But that number didn't make it into the report. And this report, when you just read it, I think comes across as fairly supportive of the CIA plan. Yeah, it could work. It's basically going to go, it could work. It could work. But if someone says to you, oh, there's a fair chance this plan works, if you're Kennedy, you're going to, okay, you know, that's pretty good. But if someone says there's a 30% chance this plan works. That feels very different. So I think how you communicate risk as a kind of intelligence official or, you know, advisor to a decision maker is crucial. And I think in this case, I think something goes wrong in terms of how that risk is communicated, because

Kennedy kind of seems to proceed on the basis that there's a better chance of it working than maybe there is. He realizes, I think, that it isn't guaranteed to work and that the choices don't look Great. You get a sense of that, don't you? You do. And you definitely get a sense that as this process kind of runs in January and February, because there's meetings all the time where Dulles and Dickie Bissell are going down to the White House and briefing Kennedy's team, JFK basically has two bad choices, right? On the one hand, if he scraps the invasion, he's going to have to disarm the Cubans in Guatemala. He's going to risk public attacks from the Cubans for failing to implement

kind of Eisenhower's plans and frankly Kennedy on the campaign trail had essentially called for a covert action plan like the one he's looking at right now and so if he kills it he risks politically being seen as soft on Castro secondly then if he goes a second bad choice

he goes forward with the invasion you could wind up in the middle of an international disaster and one of his aides actually says you know look this could lead to a wave of protest in Latin America and, quote, fix a malevolent image of the administration in the minds of millions. The geopolitical context is also important, too, because JFK is thinking, well, if I'd go ahead, Khrushchev in the Soviet Union, they might retaliate by further isolating or cutting off West Berlin, which at this point is another kind of really flashpoint in the Cold War. And if the Soviets retaliate there, how does Washington then

respond. So you can, you don't have to be a geopolitical genius to kind of walk a couple steps ahead and see how a failed invasion of Cuba or frankly even a successful one gets you into a pretty tough spot with the Soviets. That's right. So maybe there with those two choices laid out. I mean, Kennedy has been boxed in, perhaps boxed in by his own rhetoric during the campaign trail. Perhaps one might suggest boxed in by the CIA and it's briefing of him, depending on how you want to look at it and how sympathetic you are to the different different actors, but we're there with Kennedy left with these choices about how to proceed. Let's take a break, and afterwards we'll come back and see what he does.

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And from 1st of October to the 31st, you'll be able to pre-order a copy from Waterstones for half price using the code Rest 2025, Rest 2025. Rest 2025, capital R that is. Pre-order your copy of the Restis quiz by Goalhanger from Waterstone using the code, Rest with a capital R, 2025. Now. Well, welcome back. We left with newly minted President Kennedy, left with a pretty difficult choice by his CIA and National Security.

security team, what do you do? Do you go ahead with this operation, which is certainly not guaranteed success? Yeah, what do you do? And you left Gordon on the cliffhanger before the break of sort of suggesting that perhaps the CIA had boxed him in. And it's not coming from a desire to deceive the president, but it's coming from the CIA's belief that this whole thing would fall apart if Kennedy doesn't move quickly. Dickie Bissell at the end of one of these briefings says, you can't mania on this thing to JFK. So you got to move now. And I think What do you do if you're John F. Kennedy and you're stuck between a rock and a hard place. You've boxed yourself in. The logical thing to do, which is exactly what he does, is let's pair this operation down to the bone. Let's try to find this sweet spot, potentially an imaginary sweet spot, where it can still succeed, but you can keep the U.S. rule, the U.S. hand behind this hidden, very minimal. Wishful thinking, some I'd say, but yes.

Right. And I think it is, but that is exactly what John F. Kennedy does. So in a meeting on the 8th of February, JFK asks the CIA team, you know, okay, well, could the Cubans be landed gradually and quietly and make their first major military efforts from the mountains so that way they don't appear as this kind of invasion force, right? So you start to see here, he's kind of thinking, oh, are there ways there's just make this thing really quiet. JFK is also really seeking assurances from the CIA that the Cubans will not need direct overt U.S. military intervention to succeed. And the CIA gives assurances that the Cuban exiles can succeed without that kind of participation, but they do tell the president that ultimate success is going to depend on the extent to which the initial assault serves as a catalyst for anti-Castro elements throughout Cuba. So again, we're coming back to that kind of key point of does the taking and holding of a lodgment inside Cuban territory compel other anti-Castro Cubans in Havana or elsewhere to kind of rise up? And JFK, over the course

of kind of February, he gets those assurances and he starts to just kind of walk things back a little bit, right? So he wants to be sure that the U.S. role isn't obvious or it's, you know, less obvious than it would have been. And so Dulles and Bissell assure him that, look, Castro isn't going to fall without outside help, right? So we've got to, if this is the policy, you've got to do something. There's that clock ticking again. The Cuban exiles that we're training have a good chance of overthrowing Castro or of causing a civil war that we could then intervene in. And that that third point is true without the U.S. having to commit itself to an overt military campaign. So you kind of see this back and forth, as Kennedy is digging into this, he's getting assurances from Dulles and Dickie Bessel that all is well. I mean, not that there's not risk, but that this is the best possible option in front of him. Now, importantly, in March of 1961, the CIA receives a really important validation from the Pentagon when a group of colonels actually travel.

to Guatemala to review the Exile Brigade, Brigade 2506, and they come back with a report that basically in every category of training, looking at weapons handling, their leadership, the morale, the brigade soldiers receive really high marks, good, excellent, superior across most of the categories. So on the face of it, great news for the CIA, great news for Kennedy. But buried in that report, in a line that ends up getting very little attention at the time, was the colonel's assessment that the whole operation would fail without the element of surprise and that achieving surprise had only a 15% chance of success. So that is called, in journalism, that's called burying the lead.

You don't put the most important bit at the top of the story. Well, and this is another theme of the whole policy planning process is that a lot of the people who harbored real skepticism about this plan, who looked at, at it closely and very analytically and had their doubts, did not speak up clearly when they had the opportunity to say something or to inject something into the policy planning process to kind of steer it differently, or at least to make plain how risky this was to the president. So there's a lot of, and again, I can't help but think that everybody is kind of trying to please the new president and nobody, I mean, because he's brand new.

wants. Nobody wants to rock the boat. Yeah. So the message they want to go is, we can do this, you know, and, and there's fallback options, aren't there? Like, maybe rebels could fade to the mountains and hide even if the initial assault doesn't kind of collapse the regime and then, you know, it's going to continue to put pressure on the regime. So they're giving the president options, aren't they? But people are saying if the initial assault, the amphibious assault doesn't work, it could collapse. And yet still, JFK is also kind of like, can you tone it down a bit more? And he's got the kind of pressure. So I think, you know, you can see that the problems in this process, that no one's quite being honest with each other and saying, we need this or this is the chance or if you do that, this won't happen. The escape into the mountains that you mentioned is really important because that idea of this, like, there's an escape hatch. So if we land this brigade on the beach and it goes terribly,

they can just kind of fade into the mountains. And become a guerrilla force or something. And, yeah, continue to destabilize the country. Exactly. And what that tells the president and everybody else in the room is that it's not all or nothing. The cost of failure is low. So if we don't hit option A, we can just kind of roll into option B. And that's a really important mental piece of this is that all of a sudden this doesn't seem like the option is either success or everyone dies on the beach. There's something in between and we can kind of flexibly roll to that if we need to. So that's really important as well. And by the way, this is when the landing site is not at the Bay of Pigs. So just to Call that out. The landing site is not at the Bay of Pigs right now, which is important. You get to 11th of March, 1961. And in this meeting, JFK looks sticky Bissle directly in the eye and says, you got to tone it down. This is too spectacular still. It sounds like D-Day. You have to reduce the noise level of this thing. And the president gives CIA four days to revise the plan. It's not a lot of time to revise an amphibious invasion plan. And it ignores the fact that, of course, the noise level is kind of critical to the plan's overall success because you're trying, when you take this lodgment, you're trying to create a ruckus so that people in Havana and elsewhere at the island actually rise up. You don't want it to be all that quiet, right? And I think here we reach one of the points where Dickie Bissell in particular and the CIA in general do come in for some merited criticism because this point.

point where JFK is saying, tone it down, tone it down, tone it down, at some point, if you're Bissell, you've got to say, if we tone it down, it means it doesn't work. So which one do you want? And that doesn't happen. But part of the turning it down is finding a new landing zone, which is how they eventually end up at the Bay of Pigs, isn't it? Because they pick a different site from the original one, which is actually not a very suitable landing site. I mean, this is what's kind of crazy about it. It's kind of swamp land, and it's further away from the mountains, which we've just heard is the kind of escape plan. And yet, dialing it down is suddenly undermining the plan as well, isn't it? So the new landing site, the Bayo de Cochinos, is that how you pronounce it,

Gordon? How is that? Very good. Spanish. It's like an excellent Spanish. It has its advantages and its disadvantages. It's been much mocked that it sits right next to the swamp. But from the standpoint of the plan, the swamp is actually helpful because, again, the point isn't that this force is going to just, like, roll into Cuba and take Havana. The point is they're going to hold a beachhead. And so the swamp actually serves as a, you know, a sort of defensible barrier for Castro's forces to send tanks and armored columns and troops into the lodgment, the beachhead. The swamp is a moat in some ways, right? Now, the advantages of the Bay of Pigs are that it does have sandy beaches that are at least look ideal for an amphibious landing. There is a long

airstrip just inland that if the brigade can take it would work as an air strip for their B-26 Air Force, right? The area is sparsely populated, which means there's less risk from Castro's militias or interference from civilians. And again, you've got that swamp. So that's all good. But as you mentioned, there are some really notable problems. You know long have that escape hatch option. You're too far from the mountains. So if you get stuck on the beach, there is no escape. That's a really, really big downside to this new site. And it's clear that Kennedy, at least, doesn't walk away from the meetings with a sense that the escape hatch option is gone. The second problem, as pointed out by the chief propagandist on the task force

inside the Western Hemisphere Division at CIA says is the name of the spot. The Bay of Pigs. How can we have a victorious landing force waiting ashore at a place with that name? And I think that's actually right. That's actually right. So the new plan, now known as Operation Zapata, is handed into the White House four days later on the 15th March. And Kennedy looks at it, says, this is an improvement. But he's still trying to dial it down, dial the noise level down. looking for an invasion that's a little bit less invasion-like. And here, you know, I mean, if you're Bissell and Dulles, and by the way, Dulles is pretty checked out in this process. I mean, Bissell is the one who's in the weeds. I like to think of Dulles looming in the background. He's looming, yes, in a very sinister manner. I mean, actually, there is a slightly conspirator view, which is that Dulles, he knew Bissell was likely his successor, who the Kennedys might pick.

And his attitude is, I'll let Bissell take this one on. And then if it fails, well, it fails and he's gone, you know, and he could take the blame. But that may be it's conspiratorial. But anyway, yeah. Well, and Dulles stands in for plenty of blame, too. So if that was his idea, it certainly backfired. And I think this is where it's not explicit, but if you're sitting in these meetings and your Bissell and you're constantly being asked by the president to kind of tone things down, you get to a point where you have to say, the CIA and Kennedy are just talking past each other about what this operation actually is. Let me raise the, with my conspiratorial hat on, the view that some have taken about the way the CIA was playing this, which is they haven't briefed Kennedy properly. They haven't given him a decent understanding of the chances it would fail. And that that is almost deliberate. I mean, the really conspiratorial view is they set up this initial plan for failure knowing that a president couldn't allow a failure on his watch or thinking that. And that therefore,

he would then throw the weight of the US military behind the plan when it initially fails and kind of send the Pentagon to the rescue, if you like, to overthrow Castro and finish the job. And that actually, this is the kind of view of some people, which is the CIA were kind of playing JFK in that way. They knew the chances were low, but they want it to at least start and then go to the president and go, really sorry, Mr. President, I know you didn't want to put the military in, but you're going to have to go in now to finish the job. That's the kind of cynical view. Let me just lay it out there. I love that theory. It just doesn't comport with the facts. That's the problem. Whatever. Whatever. Well, it doesn't. Like all good theories. All good

theories, it's running ground on the rocks of the facts. Damn it all. I think we will see as we actually get into the, the dark days of this attempted invasion and, and see how poorly it goes. I think a stark fact that stands in the way of that theory is that the CIA team, Bissell and the people underneath him working in that task force, were fighting and clawing for the air assets required to make this plan potentially work. They were fighting for them up until the 11th hour, and they were denied them. So if you have an agency that's sort of maniacally trying to get the plan to fail, they did a pretty good job trying to make it succeed against really strong kind of pushback from the president and other senior advisors in the Kennedy White House.

Those two things are not mutually exclusive because you can still think, okay, we want this plan to work. So actually, you're not setting it up for failure, but we want this plan to work. But we We think we can persuade the president to bail us out if it doesn't. So what's happened here by the time you get to mid-March is that, you know, I think JFK is basically saying, I don't really want the strike force plan that you've built. He wants a night landing so that all of the brigade ships and the Navy, the U.S. Navy ships that will escort them will be gone by dawn. That's not part of the original plan. JFK, he's questioning even at this point, are they, are the pre-invasion air strike?

to destroy Castor's Air Force. Are those really necessary? Bissell keeps saying that they are. It's in the plan. But JFK just kind of keeps pushing back. And I think that here, again, Bissell's a really smart guy. And this is a clear example of his blind spot where instead of stepping back and basically saying, look, Mr. President, we're not seeing this thing eye to eye. He keeps pushing going forward. And it's interesting, isn't it, JFK himself is not very happy with this process. And there's this great quote where on March 28, Schlesinger, with one of his aides, asked JFK, what do you think about this damned invasion? And Kennedy replied, I think about it as little as possible. Not really what you want the main decider to be saying about your invasion plan just weeks before. I'm not really,

I'm not really thinking about it. It's like, you know, looking away from a car wreck. I don't want to see what's going to happen. Yeah, nothing to see here. And then we should mention. they're also in parallel as well. The other bit of the covert action, which we'd mentioned last time, is still going on, isn't it? Which is the attempt to kill Castro and the kind of the mafia plan. And that's a kind of separate but parallel track to the kind of Bay of Pigs Operation Zapatan. Yeah, it's a bit of the Hail Mary pass, I guess. Maybe you don't have to do any of the kind of big nasty stuff if the mafia ends up successfully killing Castro. And it really is the kind of second track of that Cuba effort. But at this point in the planning process, and by the way, we should

just restate, these two things are not integrated with each other. Bissell knows about both of them, but the mafia plot is not being run inside the Cuba Task Force. And there's very little evidence that the Cuba Task Force guys even know that it's going on. It turns out, Gordon, that the mafia bosses are not particularly discreet in sharing details of what they're up to with the CIA. They're talking to a lot of people about their anti-Castra plotting. And they've even gotten the CIA in trouble with the FBI because one of these mobsters, Sam Giancana, who's a big wig in the Chicago outfit, had convinced his CIA cutout, Bob Mayhew, to bug the hotel room of a man that Giancana suspected of

sleeping with his girlfriend. The bug is discovered by a hotel maid. The FBI is alerted, and then the CIA has to intervene and kind of say, don't push this any further. So already you can kind of see that it turns out, you know, I know last time I was pretty gung-ho on the idea of working with the mobsters, but they're causing problems for the CIA with the, with the Feebs, which nobody in CIA is going to like. Dickie Bissell is keeping his distance from all this. Kind of get the sense from Bissell's testimony later on and his writings that he was always kind of uncomfortable with the idea of using the mobsters. His secretary actually said later that when his phone would ring at the CIA and there'd be some kind of like shady underworld figure on the other end, which is probably Bob Mayhew, wanting to talk to the deputy director personally, that Bissell would not take the calls. And his secretary said, I don't know how they got the inside telephone number.

Bissell just didn't want to have any part of it. So you kind of get the sense that they've let the stick loose. They've said, look, 150,000 to whoever could kill this guy. And there's some crazy plans, aren't there, involving poisonings and some of the other attempts to kind of go after Castro. None of which seem to get close, but it's kind of the wilder side of CIA or mafia operations at this time, isn't it? Which becomes something part of popular culture, I think, as well, some of these ideas. Totally. Well, and recall that the mobsters had probably wisely thought when the CIA brought this plan that, look, we can't have an assassin just guncaster down. It's a suicide mission. We won't be able to recruit for it. And so we had last left this second track with, you know, the CIA developing poison pills, some kind of poison that could be handed off to the bob who would hand it to an agent who would deliver it into Castro's food or drinkers. something like that. And here, come back to Friend of the Pod, Sidney Gottlieb, Poisoner-in-Chief,

head of the Technical Services Division, star of episodes 35 through 39, of the rest is classified, Gordon. M.K. Ultra. He and his techs get to work developing a poison that could be delivered into Cuba. They look at options to slather something on one of Castro's cigars. Gottlieb looks at, you know, how could you coat the cigars with a botulinum toxin, which is a bacterial poison that would take several hours to be fatally absorbed into the body that would give the assassin enough time to get away. They test it on actual guinea pigs. But the guinea pigs, Gordon, they survive. And the cigars are, I don't know how they got a guinea pig to smoke a cigar. If you can't kill a guinea pig, then you did not kill the guinea pig. So, Sid Gottlieb shelved

that idea. Gottlieb did have a wild idea in this process to dust the insubes. side of Castro's diving suit with a fungus that would produce a chronic skin disease, but that idea is also put by the wayside. Wild stuff. And they just go for, I love, you know, you kind of go through these crazy ideas that eventually you just get to like,

let's go with the idea that we know is going to work, which let's just make pills that have poison at them. And technical services create a batch of six pills that contain a botulidum toxin, presumably one that's more potent than the toxin placed

on the cigars, they made those poor guinea pig smoke. And those pills are delivered from the CA to Bob Mayhew, who's that former FBI agent cutout, who's been interacting with the mob. This is actually the second batch. The first one had been rejected because the pills failed to dissolve in water, but Sid Gottlieb has tested the second batch on monkeys and found that the pills work. So Mayhew hands over the pills in Miami in mid-March, 1961. So right at the same time that Kennedy is making all these fateful decisions on the Bay of Pigs planning, Mayhew Hands Over the Pills at a meeting with handsome Johnny Raselli, Sam Giancana, and Santo Traficante, who is the kind of Florida Cuban connection in this trio of mobsters that the agency has recruited.

Now, there's an exile based in Miami, a Cuban exile named Tony Verona, who is going to arrange the job inside Cuba. These names are not for real. Verona was well known to the CIA. He's actually one of the leaders of Frente, the exiled Cuban political leadership council that is kind of the front for much of what the CIA is doing in Miami. Verona is a big wig in the Cuban exile community. He is also, according to the chief of the Cuba task force, Verona was, quote, a scoundrel a cheat and a thief who was cozy with the mafia because he hoped someday to return to Cuba and join them in business. So dealing with exiles, Gordon, is never, it's never that clean, is it?

Whether they're Iraqi or Syrian or Cuban, right, they have their own agendas. But Verona claims that he knows a man in Havana who held a ministerial post in the Castro government and might be willing to poison Castro. So that seems like, you know, this is maybe one of the best shots the agency has had, but the poison pills are never delivered to the target. There's a bit of mystery on why this was the case. Yeah, I mean, I read the different accounts of kind of girlfriends of Castro turning up in his bedroom and this kind of wild stories never quite comes off, which is maybe not

surprising because Castro knows they're after him. I mean, he's got pretty good security. You know, the idea you're going to be able to get that close to someone, but unlikely, sadly, even though this is the bit everyone loves about the CIA trying to kill Castro with poison pills and wetsuits and stuff. It never gets that close. And this is where you can start to build a really plausible case for Castro to have motive to try to kill Kennedy, right? Which will, of course, be discussing in our exclusive mini-series for club members.

Yeah, you're right. It is plausible because Castro knows Kennedy's tried to kill him. Because he's going to see evidence of some of these plots. By some accounts, he's going to confront people and things like that. But he's going to see that. So, yeah, I think it is worth saying when we're going to our, you know, who might have a motive to kill JFK, it does. Castro does.

Castro does. So JFK, the planning process is going through this whole spring. He sets a meeting for the 4th of April, 1961, to make a final decision on the plan. Now, in the meantime, the CIA, along with the State Department, the Pentagon, they're moving forward with all the logistical planning, right? And it is worth calling out, I think, the Navy's role in all of this, because it's particularly complicated. The Navy is basically going to shadow the brigade's small flotilla, because the brigade has essentially rust bucket ships that have been procured from a Cuban shipping line that was owned by an anti-Castro Cuban, right? Because no. None of the stuff that's going to be used in the actual invasion can be directly sort of linked back to CIA. So the Navy is going to escort this flotilla to the shores of Cuba. There's six ships in the flotilla. There'll be 1,500 men in the brigade that'll be landed on the shores of Cuba at the Bay of Pigs.

And kind of off in the distance, there will be a U.S. aircraft carrier, seven U.S. destroyers, 5,000 sailors aboard, who were kind of going to hide behind the horizon. and pretend like they just happen to be there while this is happening, right? So you have a whole bunch of very complicated military planning that's going on in this period. So Easter weekend of 1961, which is before that for April big decision meeting, Kennedy goes down to Palm Beach. He plays golf. He goes to Good Friday and Easter Sunday Mass, like a good Catholic. He's having meetings with his secretary of state, his military advisors. He hangs out with his father, Joe Kennedy Sr. He watches movies with the family. And when he comes back from Florida, he's a changed man. He has decided that he's going to do this. And there's been a lot of

speculation ever since about what actually changed his mind. I think it seems likely that it was the conversation with his father, who maybe bucked him up. Maybe JFK expressed some doubts about doing this and his dad weighed in in the opposite direction. Don't be a coward, son. Right. Take on the communists. Yeah. I'm not sure it was more complicated than that, to be honest with you. Because Mack Bundy, who's Kennedy's National Security Advisor, says later, he, Kennedy, went down there and something happened that made him come back and say, we're going ahead. So JFK has made up his mind. And he comes back to Washington in the meeting on the 4th of April. Dickie Bissell briefs the plan.

There's a kind of back and forth over the escape hatch again, where it's not made clear that that is no longer an option. They talk about the likelihood of Cubans actually rising up in the aftermath of the invasion. Again, inconclusive answer or an unsatisfactory answer. And at the end of the meeting, JFK goes around and basically asks everyone to say yes or no on the invasion, which I think is a terrible way to run a meeting, personally, Gordon, because it injects chaos. And also, there are a lot of junior staffers who are in this meeting as well as, like, the Joint Chiefs of Staff and the head of the CIA. And everybody is kind of, their opinion is getting weighed equally.

It's a very bizarre. I mean, I understand the reasons for Kennedy to want that kind of display, but I just don't, I just don't get it. And you know what? I mean, there are a lot of people in that room who later on are going to say they had serious doubts. Not one person spoke against it. No one in that meaning votes no. Yeah. And I think it's fascinating, isn't it?

Because, I mean, why, I mean, there's groupthink. I think that is definitely, this is a perfect example of group think. A group convinces themselves, you know, of a particular analysis or an outcome and kind of no one wants to dissent about it. He's the new virile, vigorous president. doesn't want to be seen to be the kind of guy who backs off. You can see all those kind of psychological, political pressures, you know, as well as you said, the kind of personal and family. And yet, you know, the chance of success are low, and some people know that.

And it's there in some of the paperwork. And yet, here we are. Here we are. And frankly, in a sign of, I think a very troubling sign, if you're Dickie Bissell or any of the military planners, as the meeting winds down, JFK is still tinkering with the plan and suggest it, oh, maybe we break the brigade into units of 250 men and then infiltrate them separately into Cuba. So you have darkness hanging over this. You have this total group think situation where everyone has voted yes for a plan that many of them have serious doubts in.

And as the meeting breaks up, Kennedy is still fiddling around trying to make it less noisy. But I think what's clear at this point is that the question isn't if the invasion is going to happen. It's how. And so there, I think it is a perfect place to leave it with the Bay of Pigs about to be set into motion. A moment that is going to define JFK's presidency is going to lead to so many other things. And as we'll see next time, we'll end in many ways in disaster for him and for the CIA. But of course, a reminder, if you want to hear the whole series, the whole six-part series, you can hear that now by joining the declassified club at the rest is classified.com. And you'll get access to our special mini-series, looking at why the CIA really did kill JFK.

Well, maybe not. Go on. No, that's just one of the theories. We'll be exploring the theories, including that the mafia did it with the mooch and with others. So do sign up if you want to hear us go down the rabbit hole. But otherwise, we'll see you next time. We'll see you next time.