The Rest Is Classified - 90. JFK vs the CIA: The Battle for Cuba (Ep 1)

Episode Date: October 12, 2025

“I think that Senator Kennedy's policies and recommendations for the handling of the Castro regime are probably the most dangerously irresponsible recommendations that he's made during the course of this campaign.” That was Richard Nixon, in the final presidential debate of 1960, targeting John F. Kennedy's stance on Cuba. Fidel Castro has seized power, transforming Cuba, a former “playground” for American mobsters and corporations, into a nationalist state opposing the US. The Eisenhower administration, determined to oust him, tasks the CIA to destabilise and replace the regime. Join Gordon and David as they introduce the formidable figures at the heart of this confrontation: the charismatic and increasingly communist-aligned Castro, and the brilliant, manic CIA Deputy Director for Plans, Dickie Bissell. Discover the CIA's initial ludicrous ideas - from drug-laced food to a plan to make Castro's beard fall out - and the dangerous decision to subcontract a deadly task: a plot to "eliminate" Fidel, with the American Mafia. ------------------- 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

For exclusive interviews, bonus episodes, ad-free listening, early access to series, first look at live show tickets, a weekly newsletter, and discounted books, join the Declassified Club at the Rest Is Classified.com. What a run! This champ is picking up speed. But they found a lane. Phenomenal launch into the air! Absolutely incredible air transad!

Fly the seven-time world's best leisure airline champions, Air Transat. Maybe it's just a phase you're going through. You'll get over it. I can't help you with that. The next appointment is in six months. You're not alone. Finding mental health support shouldn't leave you feeling more lost. At CamH, we know how frustrating it can be trying to access care.

We're working to build a future where the path to support is clear, and every step forward feels like progress. Not another wrong turn. Visit Cam H's. to help us forge a better path for mental health care. Halloween is on Disney Plus. Hello. So you can feel a little fear.

What's this? Whoa. Or a little more fear. I see dad be more. Or a lot of fear. Mom. Or you can get completely terrified. Who's that?

Choose wisely. Wisely with Halloween on Disney Plus. 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. And 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. Castro and his fellow dictators may rule nations. They do not rule people. The CIA were kind of playing Gen. F.K. 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 before the world.

Were you ever offered money to assassinate President Kennedy? Directly. There are 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. Can you see it, Dominic? It's our future. Cuba, 90 miles away, no goddamn justice department.

FBI. That was the past. Don't give up on Cuba, not yet. Why not? Because we haven't given up. The CIA wants change in Cuba as much as you do. We have different agendas. But we have the same goal, and we have the same resources.

Intelligence. The only thing we don't have is a way to get inside. Anyone can get inside Cuba. Smugglers do it all the time. That's not what I mean. Look, we want to restore order there. We funded dissidents, staged invasions, But none of those things are working. It's time for a new approach.

No more big operations this time. Just one man, inside, close to the government. Someone the Cubans feel they can trust. And what's this someone going to do? Kill Castro. Bring back the president. We're trying to protect this country from communist, Dominic. You could be part of that.

Well, welcome to the rest is classified. I'm Gordon Carrera. And I'm David McCloskey. And that was not just a random bit of conversation you happened to drop into between me and David, but a bit of dialogue from the legendary scene in the Godfather part two. And why are we using that legendary scene, David? Well, what better way, Gordon, to start a big new series on Cuba and the CIA and JFK than to read from the Godfather part two?

that legendary scene where Henry Mitchell and Hyman Roth and Dominic Garlioni are talking about getting back into business in Cuba in the years after Castro took power and all of these mobsters have been shoved out of Havana, lost all their money, and they're trying to get back in, and they're finding that they have been overlapping interest with the United States government and with the Central Intelligence Agency to stick it to Fidel Castro. So that's why we're reading it up front, Gordon. It sets the tone for this whole series about this insane chapter in the agency's history and really a moment, I guess, in the Cold War where an island off the coast of Florida

was the center of world affairs. That's right. Insane is the word, I think. It's an insane story. And I think it's almost driven America insane in the decade since. Because we're looking in this six-part series, really, at the relationship. between the CIA and JFK, but through the lens of Cuba, and Cuba being the critical aspect, which shapes this relationship, and which actually, strange how that one island is going to shape JFK, the 35th President of the United States whole time as president. His career is death, and the questions around his assassination, all kind of revolve around the CIA and Cuba, I think. And we should say, Gordon, we have a very special surprise for listeners. For the first time on The Rest is Classified, we are going to put out an exclusive miniseries for our declassified club members, which is going to explore, I guess really the theories, the conspiracy theories, some of the mysteries surrounding the assassination of John F. Kennedy that spring directly from the story we're going to tell over the next six episodes. And so we should say, if

If you want to listen to that exclusive miniseries, make sure you're signed up for the club, but the rest is classified.com to get access to those episodes when they go live because the story we're going to lay out over the next six episodes is going to raise some questions about whether the Cubans, whether the mob, whether, God forbid Gordon, the Central Intelligence Agency may have had motive to kill John F. Kennedy. And we're going to look at each of those theories in that exclusive miniseries for our club members. I mean, that's right. It's a story about covert action. It's a story about the relationship between presidents and the CIA. It's a story about political assassination and murder. And, yes, the theories of whether different parties could have had motive to kill President Kennedy. And I mean, I have to say, when we started researching this, David, I felt like I was a pretty kind of skeptical, rational journalist. And then you've sent me down some rabbit holes. You've lost your mind. You've become a... I've lost my mind. No, I'm going to be

honest. I've been to the grassy knoll basically now, at least in my mind and starting to at least now understand and can see why people think, not just the mob, not just Castro. But yes, even your beloved CIA could have come to hate President Kennedy so much they might have wanted to do something about it. And that surprised me, but maybe I'm not wearing a Tim Thor hat, but I'm... Maybe you will be soon. I might be soon, Gordon. I might be the... that soon. I'm on the way. We're going to talk about a story from the late 1950s at early 1960s, right, up until the point where John F. Kennedy is assassinated in Dallas. And that time period, 60 plus years later, has incredible residents today. I mean, there was a Gallup poll done just a few

years ago in the States showing that fully 65% of Americans believe that others besides Lee Harvey Oswald were involved in the assassination of President Kennedy, right? And that number is actually down from a peak of, you know, around 80 percent after Oliver Stone's movie JFK comes out in the early 1990s. Which I'd be watching. Which you've been watching as you feast on these conspiracies. And you mentioned the CIA, Gordon. When respondents to that poll are asked, the number one-sided sort of co-conspirator with Oswald is the federal government on specified. That's about 20 percent. And then the CIA at 16 percent, right? And then another 11 percent think the mafia organized crime was responsible. So this idea that this story has really

set much of the American public against the official narrative espoused by the Warren Commission and really the U.S. government about what happened in the Kennedy assassination. It is alive and well today. Yeah. And I think what's so interesting about it is it, it's, it's It's not just alive as a theory, but it is shaped American political culture. Because I think if you want to understand all the talk now about the deep state and what that deep state might be capable of, so much of it has its roots in the discussion of the Kennedy assassination and what might or might not have happened then.

So much of the talk about what the CIA could do is shaped by what's come out through the stories related to JFK. We had some document releases just in the last few months from the Trump. And of course, also, depressingly, some of the stories about political assassination, you know, we're speaking in the wake of the shooting of Charlie Kirk. Political murder is also in the news, which is at the heart of this series. So it's something from 60-odd years ago, but it's incredibly topical now and really has fed into the kind of world we live in today. And I think also does, you know, beyond the kind of conspiracy theory, it does really shine a light, I think, into the early

CIA and into the world of covert action and some of the things that we're particularly interested in this show. Yeah, the covert action point is really a fascinating one from just a pure espionage standpoint, because I think this story really illustrates a lot of the kind of promise and peril of covert action for the Central Intelligence Agency and for the American presidency, because we're going to see that this really becomes, I think, a how not to manual in the execution of a covert action program. And, you know, one of the fascinating things for me and just digging into this has been there's kind of an official narrative, and we'll explore this as the series goes on, that Bay of Pigs, this covert action program to overthrow Castro, was kind of

foisted on John F. Kennedy. But we'll see here that there's incredible connection between the Kennedy White House, the Eisenhower White House, and this program to overthrow Castro. So far from being a kind of unofficial or rogue effort by the Central Intelligence Agency, this is going to be. be a case study in how the collaboration between the White House and the CIA can go terribly wrong on a covert action program. It made me thank Gordon in some respects of Syria and the covert action experience in Syria in the early years of its civil war and just how the parallels, I mean, those two events are separated by 50 years. And a lot of the same issues that befell the CIA and Kennedy over Castro

affected the Obama White House and the CIA over Bashar al-Assad, Syria. Yeah, that's right. So it's a world of COVID action, conspiracies, and yes, cover-ups. So with all of that, let's set the scene because it all really revolves around Cuba, doesn't it?

We should probably help listeners just get into the mentality of the late 50s and early 60s on Cuba because it's not a sort of sleepy, corrupt, irrelevant dictatorship at that point in time. I mean, it's really starting to become a centerpiece of the Cold War.

And there's a lot of history with respect to the U.S. and Cuba. But just, I mean, to set it up, to begin, Cuba is 90 miles from Key West Florida. So if you think about it as an American as some kind of distant place, it is absolutely not. That's just a bit further than the distance from, I look this up, Gordon, to help our UK listeners,

from London to Oxford, or to help our Texans, it's the distance from Dallas to Waco, Texas. So it is very, very close. Or from the Isle of Man to the British mainland, as I discovered. So just imagine if you're in the northwest of England, it's the Isle of Man, which is becoming the center of British anxiety. Well, we've set it up now. We've got three different yardsticks to help everybody. The point is it's very close.

You can drive a boat there very quickly. And Cuba has been, by the time we get to the 1950s, it's coveted for generations by American statesmen going all the way back to the founding fathers. I mean, there's some choice Thomas Jefferson quotes about how much he wanted to possess Cuba. And there is a sordid history of American domination of the island. In 1898, President William McKinley, of course, famously sent American troops to Cuba to help rebels overthrow Spanish control. those troops were not withdrawn, and then afterward, McKinley named an American military governor. A few years later, actually, in 1903, something called the Platt Amendment granted Cuba limited self-rule,

but it gave the U.S. significant number of sort of powers and rights over Cuba in exchange for withdrawing most of those troops. Of course, that led to the continuation of an American naval base at Guantanamo Bay, which we still have today. I've visited three times. So weird way of seeing Cuba. That is a weird way of seeing Cuba. You've earned a lot of points in your Guantanamo Bay stays, Gordon. It's exciting. Now, at Cuba, I think we could almost think of it for much of the 20th century as almost a colony of the United States. The extent of sort of U.S. influence and control is very significant. And the U.S. landed troops on the island whenever Washington perceived its interest as being. threatened and that happened again in 1906, 1912, and 1917. There's also an American corporate stranglehold over the Cuban economy with American conglomerates and businesses owning most of Cuba's sugar plantations being heavily invested in oil, railroads, utilities, mining, cattle ranching. 80% of Cuban utilities were owned by Americans, 40% of the sugar industry is American out, and 80% of Cuban imports came from the U.S.

And prior to Castro, I know there was a period in the 30s and 40s of a tremendous amount of political instability in Havana. And coming out of this was effectively a dictatorship run by a man named Vigencio Batista. He was probably the most important figure in Cuban politics in the 30s and 40s, but he becomes the kind of unquestioned dictator of Cuba in 1952. he is U.S.-backed Cold War Strongman out of Central Casting, who is not a communist, but also exceptionally brutal and fabulously corrupt. He's pocketed maybe $300 million. Big mustache? I don't know if the mustache game was exactly what you're expecting, Gordon. The pictures I've seen he's not very well mustachioed. Those could be dated photos. By the 50s, he could have been rocking a strong mustache game. Yeah, it doesn't look at actually when you look at it,

quite clean-shaven, but yeah. So Fulgencio-Batista is running Cuba through most of the 50s. He's pocketing a tremendous amount of money from a feature of Cuban life in the 50s that is going to play a really important role in this story, which is the mob. The mob. The mob. The Batista regime has struck a deal with the American mob, hence our reading from the Godfather Part 2 to start this episode. The Hyman Roth character in The Godfather Part 2 is based on a real-life mobster named Meyer Lansky, who was one of the controlling mobsters in Havana in the 1950s. And that scene that we read from is also based on a real incident,

which took place in Havana and it was this kind of big meeting between American mobsters to establish criminal operations in Cuba and a partnership with the Batista government. So all of that stuff from the Godfather Part 2 is essentially just a documentary. Because it is a kind of playground for Americans in terms of kind of casinos and gambling, and it's a kind of playground for the mob, isn't it?

You have this vision of this kind of decadent Cuba and decadent particularly Havana in the 50s in which it is pretty wild and in which the mob has got pretty free reign in some ways. I mean, the essence of the arrangement that struck between the Batista regime and the mob is that the government grants the mobsters the right to build casinos and hotels. And then the Batista regime sets up kind of development institutions and financial institutions, which are financed by profits from the casinos. So it's a symbiotic relationship between the regime and the

mob. It's also a sort of playground for the mob in the sense that it's a bit of a bit of a free-for-all, right? It's it's the American mob that can kind of come down out of Chicago, New York, Vegas, and set up a new operation. So it's new turf for the mob, right? It's an expansion of their operations. And you're right, Gordon. I mean, there's this sense of Havana as, really, you could think about it as the actual Las Vegas of the 1950s. This is before Vegas gets big. It's a bigger operation for the mob than Vegas in the 1950s. And there's a wonderful book on this period in Havana called Havana Nocturn by

T.J. English, which is all about the mob, the Batista regime, the building revolution in the countryside. And the picture of Havana at this time is insane. I mean, again, the casinos are bigger than Vegas. There are nightclubs that are sort of set in the jungle outside

of Havana. It's an entertainment destination for Americans in particular, but also Europeans. It's got this fantastic nightclub scene. The nightclubs have huge orchestras. The Mambo dance craze comes out of this period in Havana. Becky, at that point, suggested I start singing Mambo number five, which I'm not going to do because it immediately ends Eddie Chance of anyone listening to the rest of this point.

That's right. It would really tank our downloads, Gordon. So I'm glad you've, I'm glad you refrain from doing that. Now, travel agents in this period sell a very similar vibe to what we think of Las Vegas as today, which is in the 50s what happened in Havana. stayed in Havana. Prostitution is widespread. There's lots of sex shows, private clubs and brothels. It is a very active sexual marketplace. And you recall Gordon, that scene, there's another sort of famous Havana scene in

The Godfather Part 2, when Michael and company go to this theater and see a fairly insane live sex show. And that is actually based on something that happened frequently at the Shanghai Theater in Havana. which in the 50s had been converted into a live sex emporium. The scene is actually based off of a performer who worked at this theater. His name was Superman, and he was very well known in Havana in the 1950s. I don't know why he was called Superman, Gordon.

Was it because he was a mild-mannered reporter called Clark Kent by the day? Yeah, exactly. He was a reporter by day. Journalist by day. And he wore, yeah, he just put glasses on during the day. And then wear his under, maybe he just wore his under. Maybe he just wore his underpants on the outside, like Superman does. Outside some tights. He was definitely wearing underpants for all of his shows. Celebrities wanted to be seen in Havana.

Marlon Brando was a frequent visitor. Errol Flynn. Hemingway was kind of a, you know, a local mascot in this era. He's living in Havana. Sinatra's there. JFK went in the 1950s because this is people went there. Americans went there. It's very common. And Batista is firmly on side in the Cold War, right? So Cuba's friendly. It's a playground. You have fun there. But all of this as seen by ordinary Cubans, a little bit less fun. So I think this kind of wild, kind of garish nightlife is seen in some quarters in Cuba as Yankee exploitation. There is grievance, a lot of grievance building throughout the 1950s against the Batista regime. And throughout that decade, Cuba becomes a kind of tinderbox for what will eventually become Castro's revolution. We've got a U.S. backed dictator in charge, a man who's going to end up suspending the Cuban constitution, dissolving Congress, really violently suppressing political opposition. Batista is being financed by mobsters and has turned Havana into this kind

of sinful destination for predatory Yankees from the north. Also of note, the Cuban economy in this period, not doing so well for ordinary Cubans. The price of sugar falls pretty precipitously in the 1950s. So you have this kind of point in time also geopolitically where you have nationalist kind of post-colonial movements that are erupting all over the world, gaining momentum, and from this tinderbox is going to come Castro and his revolution. So a country right for revolution and Castro on the horizon. At that moment, let's take a break and we'll come back and we'll see how revolution comes to Cuba and what that means for the CIA. With Amex Platinum, access to exclusive Amex pre-sale tickets can score you a spot

trackside. So being a fan for life turns into the trip of a lifetime. That's the powerful backing of Amex. Pre-sale tickets for future events subject to availability and varied by race. Terms and conditions apply. Learn more at amex.com. This episode is brought to you by Peloton. A new era of fitness is here. Introducing the new Peloton Cross Training Tread Plus, powered by Peloton IQ. Built for breakthroughs with personalized workout plans, real-time insights, and endless ways to move. Lift with confidence.

While Peloton IQ counts reps, corrects form, and tracks your progress. Let yourself run, lift, flow, and go. Explore the new Peloton cross-draining tread plus at OnePeloton.ca. Did you lock the front door? Check. Close the garage door?

Yep. Installed window sensors, smoke sensors, and HD cameras with night vision? No. And you set up credit card transaction alerts, a secure VPN for a private connection, and continuous monitoring for our personal info on the dark web? I'm looking into it. Stress less about security. Choose security solutions from TELUS for peace of mind at home and online. Visit tellus.com slash total security to learn more. Conditions apply.

Welcome back. We've set the scene of Cuba, just off the coast of the United States, a decadent place, right for revolution. And here comes the man, Fidel Castro, who is going to deliver that revolution and really become a thorn in the side of Washington, is neat, David. Well, he is. And it's, I think, probably helpful to set up Castro a bit, because he is going to be one of the central characters in this story. And in many ways, his fate and the fate of John F. Kennedy are going to be tied together in a very kind of interesting and bizarre way. So he's an important guy to set up here. So Castro, born in 1926, 1927 in some reports. He is the illegitimate son of a wealthy landowner in eastern Cuba. And it is a remote region of the island that's

dominated by two sugar mills that are owned by the United Fruit Company, which is a gigantic American conglomerate and kind of a symbol of that corporate dominance that we were talking about, Gordon, that American companies have over Cuba in this period. So I think for Castro, even just growing up, he is quite literally in the shadow of Yankee imperial domination of his island. Castro studies at Havana University. He earns a law degree. And in this period in 1940s, Havana, it is, as I mentioned earlier, a very tumultuous kind of political period in Cuban history. Castro really immerses himself in radical politics in this period of time.

While he's at university, most likely he comes into contact with the writings of a lot of nationalist professors who believe that Cuba's destiny has been thwarted by the United States. One thing, and I think we're going to come back to this, but I think it is worth saying, and it surprised me researching it, is that he's primarily a nationalist at this point, isn't he, rather than a communist? He's a kind of anti-imperialist, it seems to be his primary motivation. from the star. There's been a lot of ink spilled about when Castro becomes a communist in ideology and spirit. And I think it's fair to say that in this period, he's drifting that direction, but he's probably not all the way there yet. And it is, it is probably more accurate to see him as a nationalist and to view his politics through the lens of he sees the Batista regime. He sees the sort of succession of weak governments in the 40s.

as being an extension of U.S. power and influence on the island. And I think a helpful frame for thinking about really the kind of regime Castro will set up and the actions that he'll take later on is he's, I think, in this period, starting to define his political project in opposition to the United States. Not necessarily as a, you know, card-carrying communist, although he's certainly drifting toward Marxism, but as someone who is seeking to oppose the will of the United States on the island of Cuba. By the way, he earns that doctor of law's degree, which will lead to him having the Dr. Castro honorific that he'll carry with him for the rest of his life.

Castro, as we said, he is a student radical in his time in Havana at university. He leads student protests. He even takes part in an invasion of the Dominican Republic that unsuccessfully attempts to oust its U.S.-backed dictator. And in 1952, Gordon, Castro runs for Congress. But the election that year is canceled because this is the year when Batista really fully takes power in a coup. Castro initially appeals the legality of canceling that election, but that, of course, doesn't go anywhere. And soon he drifts into military opposition to the regime. So in the summer of 1953, the young Castro leads an attack on a Cuban army barracks.

It fails. He's sentenced to 15 years in prison. but in a massive and world-changing mistake, Batista will release Fidel Castro early after serving just two years. And at this point, Batista thinks, well, the Rebels' energy is kind of spent. Batista's under pressure, to some degree even from Washington,

to show that he's not really a bloodthirsty dictator. And so Fidel goes out of prison in amnesty after the 1954 presidential election in Cuba, and he goes to exile in Mexico City. Where he meets this other kind of great iconic figure of what will become 60s radicalism, Che Guevara, who is perhaps a bit more of a Marxist revolutionary, so they're kind of similar but not quite the same. Che famous for being pictured on student walls and student t-shirts.

He's not just a guy from T-shirts. He's a real guy in this story who helps Castro. Yes. And I think, I mean, Che in this period, of course, is a Marxist. I think, again, Castro's ideology a bit harder to pin down, but certainly drifting that direction. And in Mexico City, they joined forces and raise funds to support a return and another attack on Batista in Cuba. And in December of 1956, Castro, his brother Raul, Che, and 79 others sail across the Gulf of America, Gordon. They land in Cuba and Batista claim.

that basically all the rebels, including Fidel, are killed. But, of course, they're not. Fidel escapes the net. And between 1956 and 1958, essentially, Fidel's forces prosecute a kind of guerrilla war and insurgency across mostly the rural parts of Cuba. And it slowly over time begins to encircle Batista in Havana. Which I think the fact that this group of guerrillas can take the country, and they take it what, by New Year's Eve, 1958, Batista's gone. It's amazing in a way, but it's also a sign perhaps of just how unpopular Batista's regime was and how much people wanted change and how Castro Che were kind of offering this vision of change. So it means, you know, remarkably, it's a guerrilla movement which succeeds when taking the country.

Yeah, and something to set up in terms of Fidel's personality is he is remarkably charismatic. He is a force of nature. He is a gifted orator and somebody that people want to follow. And he's sort of got the wind at his backs of all of these problems that the Batista regime is facing. The kind of bigger geopolitical situation in the 1950s with this push toward sort of post-colonialism and the rise of nationalist movements all over the world. I mean, Castro has so much going for him in this period. And also he's going up against a brutal U.S.-backed, mob-financed regime in Havana that is not popular at all.

So by 59, he is in power. But what's so interesting is he's kind of overthrown this US-backed dictator. But actually, Washington, it doesn't quite know what to make of Fidel do that at the start. I mean, it is not immediately the relationship of antagonism, which we now think of, that there is this period where inside the CIA itself, but also across Washington, There are some people who actually think maybe this is the kind of new tide of nationalism, anti-colonialism, which some people in Washington kind of are quite sympathetic to, kind of sweeping parts of the world.

Maybe this is someone who's going to bring positive change to Cuba. There's definitely a tension, isn't there, in those early days about how to see him. So CIA thinks at this point, well, maybe we should get in contact with Castro. You know, he might actually establish a more representative democratic government in Cuba. that was something that was on the table in those kind of early months in 1959 as Castro is taking power. Now, what also becomes, I think, a very common assessment in Washington, and it's enforced by some of the actions Castro takes early in his tenure, is that Fidel is erratic, tyrannical, and bloodthirsty, right? He orders the execution pretty much right after taking Havana of more than 500 Batista supporters who are who are shot. Can't have a revolution without firing squads, as Lenin would say.

Right. And so at this point, you have maybe some hope that the U.S. can work with Castro and also a sense that, well, this is not going to be a particularly peaceful takeover. Now, Castro actually visits. He comes to the U.S. He visits New York in the spring of 1959 at the invitation of the American Society of Newspaper editors. And it's a wild trip, Gordon. Castro is generally quite amiable. He's greeted by well-wishers everywhere. He meets a raft of very senior U.S. officials, the acting secretary of state. He spends two and a half hours with then Vice President Richard Nixon. He shakes Jackie Robinson's hand.

Jackie Robinson, of course, famous for breaking the color barrier and being the first African-American to play major league baseball. Fidel Castro, you know, plays with school kids. he's kind of embraced by elements of American society and certainly by the kind of growing American counterculture at that point in time. There's a, there's a great picture of someone carrying a placard in New York as Fidel is visiting that said, man, like us, cats dig Fidel the most. He knows what's hip and bugs the squares. That's essentially a 1950s version of a Che Guevara t-shirt at that point. I barely understand it, but I think I know what you mean. He's cool. And the Fidel Beards become a thing. People are trying to imitate them. He's this kind of, you know,

cool revolutionary younger generational figure, isn't he? That's right. Spring of 1959, if you were looking for a great party gift to give someone, you might have given them a costume Fidel beard made from treated dog or fox hair. That was a common novelty item in America that spring. And all of this kind of builds to this idea that at this stage, you could maybe look the other way on all those executions that Castro has undertaken in Havana and believe that even though Castro's government is, in fact, peppered with communists and Marxists, maybe he himself is not. And he's asked this question constantly on the trip to New York. Are you a communist, Dr. Castro? Are you a communist? And he says he's not. He refutes the idea that he's a card-carrying communist.

And that really, though, in this moment in the Cold War, that is the existential question for the American establishment is, is Fidel Castro a communist? And Gordon, a CIA officer meets Castro during this trip and actually sits down with them face to face in Washington and comes away convinced that Castro is not a communist, but instead, perhaps a new spiritual leader of Latin American democratic and anti-dictator forces. Brilliant piece of CIA analysis. That's a great piece of analysis. That mini-McCloskey failed the brief right there. Yeah, he did not get his analysis right. And it is true that unlike his brother Raoul, Fidel has not been in the Communist Party. He doesn't yet have a relationship with the Soviet Union.

And when he sits down with Vice President Nixon, I think Nixon's assessment is pretty close to where official Washington is at that point. Because Nixon comes away and thinks Castro is either incredible. incredibly naive about communism and the strength of sort of communism inside his own government, or he's under communist discipline. And essentially, I think Nixon is saying, like, we have to kind of deal with him as though he is a communist. I think what's interesting is as his regime starts to take shape back in Cuba, he starts to do things which are against, you know, American corporate interests, the way in which America had exploited Cuba, as we talked about earlier, which, of course, if you're negatively disposed to communist, you'll say it's

communism, but also you could still see as that kind of nationalism, anti-imperialism, trying to kind of clear out the economic exploitation by the US. But what he is going to do is kind of try and eject those American forces, whether it's business or the mob, from Cuba, which he sees as having exploited his country, which, of course, if you want to see it as kind of a communist move, you could. But it isn't necessarily that, even at the this point. No, not necessarily. And I think even, even as Castro starts appropriating, you know, American investments to the tune of hundreds of millions of dollars in Cuba, you're right, Gordon. I mean, you could spin a story that, that he is just a nationalist who wants Cuba to be

much more independent. What he does do in this period, though, is he infuriates the mob because he imposes much more stringent controls on the sort of hotel and casino scene. And loads of American mobsters are essentially kicked out of Havana and lose their shirts in the process. I mean, a lot of these organizations had invested considerable sums and setting up and running these casinos and hotels, and they are basically shoved out and not compensated for it. So you have a whole bunch of furious mobsters that tuck tail and go back to Miami or Chicago or New York with a real beef against Fidel Castro. And Castro, I mean, to your point on sort of, you know, is he a nationalist?

I mean, he pursues land reform, which, again, is that you're a communist or are you just a Cuban nationalist, which, of course, makes the American owners of big sugar mills and plantations and cattle ranches extremely anxious. He's imprisoning. Castro's imprisoning thousands of Cuban citizens, some with very close ties to the U.S. The executions continue. So Castro is building a pretty diverse set of enemies in the United States. So you have a kind of growing exile community of Cubans that. have gone to Florida, in particular Miami. And there's just kind of a steady flow and are still there. You have American corporate interests where you have properties that have been nationalized. You have the mob.

And then you also have conservatives, people like Richard Nixon, who are stridently anti-communist and who see in Fidel's regime, maybe it's not consolidated yet, but at this point you at least have the prospect of a communist controlled government that is 90 miles from Florida, which has in this point in the Cold War, you don't have any sort of communist stronghold that close to the US and the Western Hemisphere. So this is a new and very threatening development. And of course, the US views this as its hemisphere and therefore, even if it doesn't have its sphere of influence and the idea of any kind of communist foothold there is something which is kind of anathema to Washington. I mean, the contacts start a little bit with the Soviet

Union, I think with the KGB. There's some signs of contact, but it's still not massive. at this point in 1959, is it? No, it's not. I think the KGB, the Soviets, are also trying to feel out Castro in this period. There is a connection that begins pretty soon after he takes Havana between Castro's security services and the KGB. Communist influence, I think, though, over the course of 1959, does become more apparent inside Castro's regime. So you have even small things like officials inside the regime calling each other

comrade or the word God being stricken from the Cuban Constitution or red stars being painted on Castro's military vehicles. So if you're writing the analysis, you can start to build a picture of this is a communist takeover. And in resistance to this, a spate of anti-Castro terror begins in Havana and around Cuba, with Cuban starting to resist. There are department stores in Havana that are bombed. There's a ship in Havana harbor that's blown up that kills more than 100. Sugar plantations are burned. You have, as we said, this growing exile community that's fleeing and coming to Florida. And amid all of this, I think the Eisenhower administration is looking at this and saying, what is the Cuba policy

going to be? So in October of 1959, Eisenhower tasks the State Department to come up with that policy. And what the State Department does is they write down that essentially the policy will be to encourage and coalesce opposition to the Castro regime's present form while avoiding giving the impression of direct pressure or intervention. Which makes it sound like a job for the CIA. It is a job for the CIA, Gordon. I thought you'd never say it. I thought we'd never get there. If you want to encourage opposition, but without giving the impression of direct pressure, I wonder which part of the U.S. government that will fall to. I think it's time for the CIA to enter the story properly.

It is. It is. And, of course, so the State Department writes the words, the CIA is going to do it. And I think it's worth setting up the CIA of the late 1950s before we get to the specifics of what the CIA thinks it might do with Fidel because the CIA of the 1950s is very different from the Central Intelligence Agency of today, as we'll see. that's okay, Gordon. For those who didn't hear that faint noise that Gordon made, that was a sound of incredible skepticism.

The deep state endures. Yeah, exactly. And a sign of maybe Gordon's trip down the rabbit trail of conspiracy. So the CIA at this point in time in the late 1950s is a very young organization. It's been around only since 1947. It is full of white Anglo-Saxon Protestants. Wasps. wasps, skull and bones types, guys who graduated from Yale. You've compared them before to which

the Bullington Club. Yeah, the Bullington Club, where David Cameron and Boris Johnson went, which is the kind of elite drinking society of Oxford and in this case, skull and bones of Yale. But it's a kind of elite crowd, isn't it? Slightly entitled, some people might say. Just slightly, yes. So I think there's four things to know about the CIA of this period. one to this point on kind of waspy skull and bones types it is staffed with rich well-connected white guys who spent a lot of the Second World War blowing things up all over Europe okay so this is full of OSS Office of Strategic Services guys whose experience in intelligence is destroying Nazi railroads and and supply depots right so this is a an organization of covert action

you could say where it's it's a little bit less Let's just kind of get the facts about the world. Yeah. Yeah. Yes. Led by Alan Dulles. Yes. Friend of the pod.

He is the leader of the CIA at this point. And he's going to be a big vigor, I think, in our story. And actually in some of the theories, I'm not going to call them conspiracy theories, involving the CIA and J.F.K., which we'll end up coming to. So I think we should just spend a moment on Dulles because he's kind of emblematic. Isn't he of that kind of crowd who are from the elite who've served in World War? War II. He'd been a corporate lawyer, I think, you know, who'd been his background in the 30s. Actually did quite a lot of work with Nazi Germany and with kind of German industrialists.

And then is in OSS, the precursor to the CIA in World War II. And he's in Switzerland, isn't he? Which is quite a kind of neutral venue where he can use some of those contacts and do all kinds of things. But he is, I think, a really interesting character because if you read some of the books I've been reading, David, about the CIA in this period, he is, emblematic of what you might call a certain vision of American power in which I think corporate interests are allied to an assertive view of American policy around the world. So a lot of what the CIA will be doing in the 50s and even beyond that will be about shaping the world, but also shaping it to be safe for some of the corporations which Alan Dulles has worked for as a lawyer,

you know, including the United Fruit Company we mentioned, you know, and they're going to launch a coup in Guatemala to make the country basically safe for the United Fruit and American company. And even if we go back to Iran, you know, oil is part of the motivation. So there is this kind of sense in which Alan Dulles is emblematic of a certain type of American elite and a certain view of the world and of what the CIA should do. Fair? Unfair? Well, you've kind of, you've said this in sneering tones, which makes it sound die of. I mean, I don't disagree. I think it's just a happy alignment of geopolitical and corporate interest that just so happened to be connected. You know, I mean, you can have instances where a country's geopolitical or security interests sort of conflict with its corporate interests. And in this case, we just have a wonderful example of alignment between Washington and giant U.S. conglomerates, Gordon. It feels, I mean, what's more innocent than that, right? Well, we'll let listeners make up their own minds about it.

But I think Dulles is emblematic of that, of this kind of Washington elite, isn't he? And of a pretty aggressive posture for the CIA. Also worth saying that his brother, John Foster Dulles, is the Secretary of State. I mean, it is amazing. One brother is Secretary of State and the other brother is running the CIA through the 50s under Eisenhower. It's amazing, really. It's efficient, you know. It's keep it in the family.

And then, you know, later in the story, of course, we'll have, you know, JFK and then his brother, RFK will be, the attorney general. So we've got distinguished brothers left and right in this story. Now, I only said, Gordon, that Alan Dulles was a friend of the pod, not because of his sort of corporate malfeasance, but because he was one of our characters in the very first episodes we did of the rest is classified on what you, I think, on charitable be described as a CIA coup in Iran that Dulles was involved in. Now, Dulles, just from a character standpoint, he likes a tweed suit in a pipe. He has a remarkable libido. He's a notable philanderer. He probably has an affair with the Queen of Greece at work in his office. He does not look like a sinister spymaster.

He looks like a kind of grandfatherly figure, I would say. And you're right that he is a feature of the story and really an embodiment, I think, of the Central Intelligence Agency by the time we get to the Kennedy administration. We should also say, so, That's point one on the agency. It's staffed with guys like Dulles. Two is that there really isn't any congressional oversight in this period. So there isn't much of a check on the executive branches control over the CIA. And there's a great story from one of Dulles's administrative aides where he basically says that when Dulles would brief Congress, because he would do this sometimes to keep them informed.

He'd brief one of the committees. and, you know, Dulles would go and ask for money. They would usually give it to him. And Dulles would say, you know, I think Mr. Chairman, I've asked for as much as I can spend wisely. If I get into trouble, I'll come back to your committee. And the congressman would bang his gavel and say meeting adjourned. And that was that. So there is a very loose congressional hand over the Central Intelligence Agency at this period.

So that's two. Three is the CIA is charged with rolling back communist influence worldwide without triggering a third world war. And it functions in many respects as the kind of executive action arm of the White House. And a reporter wants to ask Dulles, what is the CIA? And he said it's the State Department for unfriendly countries. That's such a good quote. So countries where we might have to do some stuff to make them more amenable to U.S. interests. That's when the CIA in this period gets involved. And I find it very interesting because under Eisenhower, you know, who is president through most of the 50s, Second World War General, actually this experienced military leader,

but who actually has a kind of aversion to getting the US into another shooting war, I think. And therefore actually comes to see the value of the CIA in carrying out kind of covert activity and being very aggressive in some of its programs and its covert actions, precisely because he sees it as a kind of tool to roll back communism to create the kind of world that he sees as important, but not to get into an all-out shooting war. And I think for that reason, I think it feels like he does give Dulles and the CIA a lot of latitude. And I think as he comes to the end of his presence, he possibly thinks too much latitude. I think that's one of the things he might think in Eisenhower's case. But certainly, covert action becomes quite intrinsic

to U.S. policy in this period under Eisenhower. Well, all of the significant characters we're going to talk about when they look at the world and they look at unfriendly countries, let's say. They are framing the world of possibility through the lens of the Second World War, a total war that resulted in so much misery that had basically destroyed the European continent and much of Asia and resulted in the dropping of nuclear bombs on Japan. So they are trying to avoid that at all costs and covert action in this period. I think we have a tendency to look back on some of these CIA adventures, let's say from the 50s, and think, oh, you know, that caused more sort of long-term harm than good. These were unwise. They were all being crafted by guys like

Dulles and Eisenhower and many of the other characters that would meet with the express goal of affecting political outcomes somewhere to roll back what was seen as a communist desire to sort of slowly encapsulate the world. They're trying to use the CIA to roll that influence back without getting everybody into a total war. So Eisenhower, I think, becomes very enamored with using the CIA for covert action purposes because you could conceivably avoid that total war. You don't have to be overt with the way you're using, you know, U.S. power. and prestige. And I think Eisenhower also, Gordon, would have seen, it wouldn't have been well known or known at all at the time in the 50s, but he would have seen the effectiveness of

intelligence and covert action at work in the Second World War. I mean, the breaking of German codes. Eisenhower would have understood the value that an intelligence service could play in winning a conflict. And I think just turns more and more to the central intelligence agency throughout his term. But he's not going to be shied using the most aggressive tool. as we'll see. Well, that's right. And fourth, I think this is an important thing to note on the CIA is that because of this demand from the White House, the CIA is really growing bureaucratically in this period. It is literally sprawling into new real estate. And this is throughout our story, the CIA will actually not be really working from Langley yet. But the cornerstone is laid for the Central Intelligence Agency's headquarters out at Langley. in 1959. So it's being throughout much of most of our story, the headquarters building is being constructed. It is a 258 acre campus with a million square feet of office space that makes it in terms of sort of U.S. government office space only second in size next to the Pentagon. And it's

massive. There's a 500-seat auditorium. There's a cafeteria that can accommodate a thousand people. There's a 3,000 car parking garage. So American intelligence has gone in the span of a decade from a really, really small elite enterprise to part of the Washington sort of bureaucratic establishment by the end of the 1950s. So we've got this picture of a CIA which is led by these kind of aggressive covert operators, relatively little oversight, tasked by the president with rolling back communism growing rapidly, and then there is Castro in Cuba, just off the U.S. coast. And I mean, you can see, you know, what's coming in a sense, can't you? You can see that the push is going to be there for the CIA to take the lead in destabilizing and going after Castro.

Yeah, you know, it's interesting that the CIA now looking back at this period, I think it gets a bit of a bad rap, Gordon, for the allegation that the agency kind of came up with a really hastily developed plan to deal with Castro and kind of foisted it on. the Kennedy White House. And I think it's interesting when you look back at it. The CIA is actually a bit late to the party on the assessment that Castro has to go. The State Department, of course, had developed that policy. And throughout 1959, though, the agency is assessing that while Castro is drifting left, he's tolerating communists rather than embracing them. So the national intelligence estimates that are produced in that period run a bit counter to the state departments or the assumptions underlying the State Department's policy. And as late as November 59. So after the State Department has essentially said U.S. policy is that we need to find a way to

quietly push Castro out, the CIA deputy director testifies to Congress that Castro himself is not a communist. So the CIA is, I think, slowly, maybe more slowly than some of the other arms of government coming to terms with Castro as a communist. Now, Dulles in this period is quite old. He's in his late 60s. And he is increasingly, as we'll see, I think disengaged from some of the day-to-day work that's going on at the Central Intelligence Agency. Much of the work on Cuba is going to fall to Dulles' Deputy Director for Plans, Richard Bissell. Now, the Deputy Director for Plans is essentially the equivalent of the Deputy Director for Operations today. So it is the number one guy or girl in operations at the CIA, which at that time really meant an intense focus on covert action, right?

Now, Richard Bissell is Dick to his colleagues and Dickie to his friends. And I think as a new friend of the pod will refer to him as Dickie. Dickie Bissell. In these episodes, Dickie Bissell. Now, Bissell is a 1950s CIA officer out of central casting. He is this kind of brilliant character. He's raised in a wealthy Connecticut family. grows up in Mark Twain's old house. As a boy for one of his hobbies, and it's a hobby that

will continue into his adult years, he reads railroad timetables and rate schedules for fun. Wow. As we'll see him in the middle of the Cuban crisis on weekends, he will sometimes do just that from his living room in Washington, D.C. Dickie Bissell graduates from Groton and where else. Yale. He works for the Marshall Plan, where he was a deputy assistant administrator. administrator, which doesn't sound that interesting, but it meant that quite literally he controlled the flow of cash that rebuilt Europe. So Dickie Bissell basically was the purse strings for the Marshall Plan. He works for the Ford Foundation. He runs with this kind of elite Georgetown set, this group of politicians and bureaucrats and journalists that are very

influential in Washington in the 1950s. And live in the area called Georgetown. In, yeah, the Georgetown area, D.C. features people like Catherine Graham, who's the publisher of the Washington Post at the time. The elite. Yeah, the elite. Now, he also likes to sail. He's got a 54-foot sailboat that he sails off the coast of Maine. He tours in Europe. He's also got manic energy, Gordon, and I think really is the epitome of the 1950s CIA man, this kind of, you know, Ph.D. who could win a bar fight. He paces incessantly. He charges down hallways. When he's sitting, he's always, his hands are always moving. He's, you know, twisting paper clips and throwing pencils. He's

kind of got this bundle of nervous energy. Dickie Bissell has wound up at the CIA because he befriended Alan Dulles and then, as we'll see, the CIA of the 50s is also a little bit loosey-goosey on how it sort of brings people into the organization's orbit. So he kind of just starts freelancing for Dulles and taking on odd projects, one of which becomes the overthrow of the Guatemalan president in 1954. I actually don't think that Dickey Bissell was a W-2 employee of the Central Intelligence Agency in this period. He was like a contractor who had been brought in by Dulles to run a covert action program in Guatemala.

Yeah, to overthrow a government on behalf of a U.S. corporation, United Truth, basically. It's a very interesting story. We should do that one another time. But I think we're getting a picture of this slightly aggressive, confident operator, basically. He's also extremely competent. So he does, after Guatemala, join the CIA full time. and he takes on a title of Dulles' special assistant where he leads the program to develop the U-2 spy plane, Gordon.

The Air Force had predicted that it would take six years to develop the U-2. Bissell did it in under 20 months, and he came in $3 million under budget. And by early 1959, he is Dulles' deputy director for plans, and if the story that we're going to tell had gone a different way, I think there's good reason to think he would have become the director of the Central Intelligence Agency. We should also say, I mean, Bissell is probably the most important CIA officer involved in the anti-Castro planning in the first few years of the Kennedy administration. And he is remarkably stubborn.

He has a proclivity for danger as a kid. On one occasion in Yale, when he was a student, he nearly killed himself falling off of a cliff near New Haven. Haven. He falls 30 feet and then tumbles another 40, ends up tearing his collarbone from his sternum, and then when he is healed, he goes back to the same cliff again, and this time gets up to the top. He is confident. He's very persuasive, very persuasive in meetings, which is also going to be really important. Dominering, perhaps. Stubborn. Domineering, yes. Blind spots. And he's got real blind spots. And the man who will become JFK's National Security. Security Advisor, McGeorge Bundy, and who was actually a friend of Bissells at Yale, wrote to JFK and said,

if Dick has a fault, it is that he does not look at all sides of the question. So we've got this really competent, aggressive, stubborn guy full of manic energy who is going to be essentially put in charge of the cubophile at the CIA. and we're going to see pretty much right off the bat this kind of predilection for action that Bissell has because on December 11th of 1959, so as the CIA is trying to figure out what to do with this policy that the State Department has handed it,

Bissellis sends Alan Dulles a memo suggesting that, quote, thorough consideration be given to the elimination of Fidel Castro. And then Dulles, looking at this, pencils in a correction. He strikes out elimination and replace, which I think elimination kind of suggests that you are going to kill him. So Dulles replaces it with removal. And so right away, we have this idea of assassinating Fidel, bubbling up to the surface of the CIA's thinking.

It's put on the back burner, but planning is going to begin in earnest to orchestrate the overthrow of Fidel Castro. So there with plans for elimination. or removal of Fidel Castro and his beard by the CIA. We're going to leave it. Next time, join us as we look at how those plans evolve and lead to what is, I think, David, one of the greatest catastrophes for the CIA with the Bay of Pigs invasions, it's called. And we'll also look at how that in turn feeds in to the Kennedy presidency and to the question. of who really killed JFK. But of course, if you don't want to wait for that episode,

you can join the Declassified Club, go to the Rest Is Classified.com, become a member. And we would also be remiss, Gordon, I think if we didn't say that paired with this series on Kennedy, Cuba, and the CIA, we have a very exclusive mini-series for our club members that is going to explore sort of the connection between all of this history

and the assassination of John F. Kennedy. we will also be joined in that series by a very special guest. The mooch, Anthony Scaramucci, who is going to be with us to talk about one of those theories, which is the mafia's connection to the assassination of John F. Kennedy. So go and join the club at the rest is classified.com. We'll see you next time. See you next time. Alastair Campbell here from The Rest is Politics.

Now, we've just released this series on one of the most controversial and consequential people of the past 50 years. Rupert Murdoch. I think you can argue that he is the most consequential figure of the second half of the 20th century. He holds power longer than anyone else in our time. And it's meaningful power. It's phenomenal power. Power without responsibility, the prerogative of the harlot throughout the ages. This is where he becomes not just a news, paper owner, he becomes a major newsmaker.

Fuck Daker Publish. There is always a premium on bringing him gossip. I don't know what you mean by down market and upmarket. That is so English class-ridden snobbery when you talk like that. How you get it doesn't make any difference.

Actually, to be perfectly honest, whether it's true or not, doesn't make much difference. There is a massive, massive scandal brewing. This was industrial, illegal activity, and that I think is is what really cuts through to the public and things. You people are really, really bad.

I would just like to say one sentence. This is the most humble day of my life. There is no Donald Trump without Fox News. His dream was always to elect a president of the United States. The bitter irony is that that turned out to be Donald Trump. A man, he detests. He is conquering the world. There's nothing less than this methodical step

by step progress to take over everything. To hear more, just search the rest is politics wherever you get your podcasts.