90. JFK vs the CIA: The Battle for Cuba (Ep 1)

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Speaker 17 From Dallas, Texas, the flash, apparently official, President Kennedy, died at 1 p.m. Central Standard Time.

Speaker 19 Cuba itself is really quickly going to become become the Kennedy administration's top priority.

Speaker 17 The next four years are going to be difficult and challenging years for us all.

Speaker 14 At the end of the day, the U.S. is facing off against this tiny island, Cuba.

Speaker 22 How could you lose?

Speaker 23 Castro will tell the General Assembly the United States is seeking to overthrow him.

Speaker 22 Kennedy really looks to the CIA to get the business of the Cold War done.

Speaker 24 Castro and his fellow dictators, they rule nations, they do not rule people.

Speaker 14 The CIA were kind of playing JFK.

Speaker 24 In the eyes of some CIA-trained militants, Kennedy had become a traitor to the cause.

Speaker 23 B-26 bombers of the Cuban exile air force attacked Castro's airfield.

Speaker 26 Everything that could go wrong does.

Speaker 22 Out of ammunition, men fighting in water, if no help given, Blue Beach lost.

Speaker 23 The airstrike has humiliated the United States before the world.

Speaker 24 Were you ever offered money to assassinate President Kennedy? Directly,

Speaker 24 on numerous occasions.

Speaker 17 It is clear that the forces of communism are not to be underestimated in Cuba or anywhere else in the world.

Speaker 23 It's like a nightmare.

Speaker 14 It's

Speaker 14 something you think, well, I'll wake up tomorrow and it's not true.

Speaker 14 Can you see it, Dominic? It's our future. Cuba.
90 miles away, no goddamn Justice Department. No FBI.

Speaker 27 That was the past.

Speaker 14 Don't give up on Cuba, not yet.

Speaker 28 Why not?

Speaker 14 Because we haven't given up. The CIA wants change in Cuba as much as you do.

Speaker 29 We have different agendas.

Speaker 14 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.

Speaker 20 Anyone can get inside Cuba.

Speaker 30 Smugglers do it all the time.

Speaker 14 That's not what I mean. Look, we want to restore order there.
We've funded dissidents, staged invasions, but none of those things are working. It's time for a new approach.

Speaker 14 No more big operations this time. Just one man, inside, close to the government.
Someone the Cubans feel they can trust.

Speaker 31 And what's this someone gonna do?

Speaker 14 Kill Castro.

Speaker 14 Bring back the president. We're trying to protect this country from communists, Dominic.
You could be part of that.

Speaker 14 Well, welcome to The Rest is Classified. I'm Gordon Carrera.

Speaker 6 And I'm David McCloskey.

Speaker 14 And that

Speaker 14 was not just a random bit of conversation you happened to dropped into between me and David, but a bit of dialogue from the legendary scene in The Godfather Part 2.

Speaker 14 And why are we using that legendary scene, David?

Speaker 7 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 2, that legendary scene where Henry Mitchell and Hyman Roth and Dominic Garleone are talking about getting back into business in Cuba in the years after

Speaker 48 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.

Speaker 47 And they're finding that they have an overlapping interest with the United States government and with the Central Intelligence Agency to stick it to Fidel Castro.

Speaker 52 So that's why we're reading it up front, Gordon.

Speaker 40 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.

Speaker 14 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.

Speaker 14 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,

Speaker 14 the 35th president of the United States, whole time as president.

Speaker 14 His career, his death, and the questions around his assassination all kind of revolve around the CIA and Cuba, I think.

Speaker 2 And we should say, Gordon, we have a very special surprise for listeners.

Speaker 34 For the first time on The Rest Is Classified, we are going to put out an exclusive mini-series 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.

Speaker 34 Kennedy that spring directly from the story we're going to tell over the next six episodes.

Speaker 1 And so we should say, if you want to listen to that exclusive miniseries, make sure you're signed up for the club at therestisclassified.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 kill John F.

Speaker 1 Kennedy.

Speaker 47 And we're going to look at each of those theories in that exclusive mini-series for our club members.

Speaker 14 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.

Speaker 14 And yes, the theories of whether different parties could have had motive to kill President Kennedy.

Speaker 14 And I mean, I have to say, when we started researching this, David, I I felt like I was a pretty kind of skeptical, rational journalist. And then you've sent me down some rabbit holes.

Speaker 5 You've lost your mind.

Speaker 69 You've become...

Speaker 14 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.

Speaker 14 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.

Speaker 14 And that surprised me, but maybe I'm not wearing a Tim Fole hat, but maybe I will be soon.

Speaker 21 Maybe I might be soon.

Speaker 14 I might be there soon. I'm on the way.

Speaker 71 We're going to talk about a story from the late 1950s and early 1960s, right?

Speaker 72 Up until the point where John F.

Speaker 1 Kennedy is assassinated in Dallas.

Speaker 34 And that time period, 60 plus years later, has incredible resonance today.

Speaker 2 I mean, there was a Gallup poll done just a few years ago in the States showing that fully 65%

Speaker 52 of Americans believe that others besides Lee Harvey Oswald were involved in the assassination of President Kennedy, right?

Speaker 60 And that number is actually down from a peak of, you know, around 80%

Speaker 58 after Oliver Stone's movie JFK comes out in the early 1990s.

Speaker 14 Which I'll be watching.

Speaker 21 Which you've been watching as you feast on these conspiracies.

Speaker 42 And you mentioned the CIA, Gordon, when respondents to that poll are asked, the number one cited sort of co-conspirator with Oswald is the federal government, unspecified.

Speaker 1 That's about 20%.

Speaker 67 And then the CIA at 16%, right?

Speaker 1 And then another 11% think the mafia or organized crime was responsible.

Speaker 77 So this idea that this story has really set much of the American public against the official narrative.

Speaker 1 espoused by the Warren Commission and really the U.S.

Speaker 47 government about what happened in the Kennedy assassination.

Speaker 32 It is alive and well today.

Speaker 6 Yeah.

Speaker 14 And I think what's so interesting about it is it's not just alive as a theory, but it has shaped American political culture.

Speaker 14 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.

Speaker 14 So much of the talk about what the CIA could do is shaped by what's come out through the stories related to JFK.

Speaker 14 And we had some document releases just in the last few months from the Trump administration. And of course, also depressingly, some of the stories about political assassination.

Speaker 14 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.

Speaker 14 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.

Speaker 14 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 COVID action and some of the things that we're particularly interested in in this show.

Speaker 73 Yeah, the COVID 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 COVID action for the Central Intelligence Agency and for the American presidency, because

Speaker 68 we're going to see that this really becomes, I think, a how-not to manual in the execution of a covert action program.

Speaker 6 And, you know, one of the fascinating things for me in just digging into this has been there's kind of an official narrative, and we'll explore this as the series goes on, that

Speaker 45 Bay of Pigs, this covert action program to overthrow Castro, was kind of foisted on John F.

Speaker 48 Kennedy.

Speaker 1 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.

Speaker 47 So far from being a kind of unofficial or rogue effort by the Central Intelligence Agency, this is going to be a case study

Speaker 20 in how the collaboration between the White House and the CIA can go terribly wrong on a covert action program.

Speaker 40 It made me think, 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.

Speaker 26 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.

Speaker 14 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?

Speaker 52 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.

Speaker 30 I mean, it's really starting to become a centerpiece of the Cold War.

Speaker 74 And there's a lot of history with respect to the U.S.

Speaker 3 and Cuba.

Speaker 52 But just, I mean, to set it up, to begin, Cuba is 90 miles from Key West, Florida.

Speaker 1 So if you think about it as an American, as some kind of distant place, it is absolutely not.

Speaker 1 That's just a bit further than the distance from, I looked this up, Gordon, to help our UK listeners, from London to Oxford.

Speaker 5 Or to help our Texans, it's the distance from Dallas to Waco, Texas.

Speaker 38 So it is very, very close.

Speaker 14 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.

Speaker 31 Well, we've set it up now. We've got three different yardsticks to help everybody.

Speaker 77 The point is, it's very close. You can drive a boat there very quickly.

Speaker 70 And Cuba has been, by the time we get to the 1950s, coveted for generations by American statesmen, going all the way back to the founding fathers.

Speaker 44 I mean, there's some choice Thomas Jefferson quotes about how much he wanted to possess Cuba.

Speaker 75 And there is a sordid history of American domination of the island.

Speaker 72 In 1898, President William McKinley, of course, famously sent American troops to Cuba to help rebels overthrow Spanish control.

Speaker 72 Those troops were not withdrawn, and then afterward, McKinley named it American military governor.

Speaker 30 A few years later, actually in 1903, something called the Platt Amendment granted Cuba limited self-rule, but it gave the U.S.

Speaker 30 a significant number of sort of powers and rights over Cuba in exchange for withdrawing most of those troops.

Speaker 8 Of course, that led to the continuation of an American naval base at Guantanamo Bay, which we still have today.

Speaker 14 I've visited three times. So weird way of seeing Cuba, but yeah.

Speaker 31 That is a weird way of seeing Cuba.

Speaker 30 You've earned a lot of points in your Guantanamo Bay stays, Gordon.

Speaker 10 It's exciting.

Speaker 19 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.

Speaker 31 The extent of sort of U.S.

Speaker 67 influence and control is very significant.

Speaker 76 And the U.S.

Speaker 68 landed troops on the island whenever Washington perceived its interests as being threatened.

Speaker 67 And that happened again in 1906, 1912, and 1917.

Speaker 2 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.

Speaker 34 80%

Speaker 31 of Cuban utilities were owned by Americans.

Speaker 72 40% of the sugar industry is American-owned. And 80% of Cuban imports came from the U.S.

Speaker 30 And prior to Castro,

Speaker 1 there was a period in the 30s and 40s of a tremendous amount of political instability in Havana.

Speaker 72 And coming out of this was effectively a dictatorship run by a man named Vulgencio Batista.

Speaker 1 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.

Speaker 64 He is a U.S.-backed Cold War strongman out of central casting who is not a communist, but also exceptionally brutal and fabulously corrupt.

Speaker 49 He's pocketed maybe $300 million.

Speaker 21 Big mustache?

Speaker 5 I don't know if the mustache game was exactly what you're expecting, Gordon.

Speaker 46 In the pictures I've seen, he's not very well mustachioed.

Speaker 10 Okay.

Speaker 52 But those could be dated photos.

Speaker 46 By the 50s, he could have been rocking a strong mustache game.

Speaker 14 Yeah, it doesn't look actually when you look at it quite clean-shaven, but yeah.

Speaker 74 So Fulgencio Batista is running Cuba through most of the 50s.

Speaker 1 He's pocketing a tremendous amount of money from a feature of Cuban life life in the 50s that is going to play a really important role in this story, which is the mob.

Speaker 79 The mob.

Speaker 3 The mob.

Speaker 40 The Batista regime has struck a deal with the American mob, hence our reading from The Godfather Part II to start this episode.

Speaker 42 The Hyman Roth character in The Godfather Part II is based on a real-life mobster named Meyer Lansky, who was one of the controlling mobsters in Havana in the 1950s.

Speaker 49 And

Speaker 52 that scene that we read from is also based on a real incident which took place in Havana.

Speaker 1 And it was this kind of big meeting between American mobsters to establish criminal operations in Cuba and a partnership with the Batista government.

Speaker 5 So all of that stuff from The Godfather Part II is essentially just a documentary.

Speaker 14 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?

Speaker 14 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.

Speaker 60 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.

Speaker 1 And then the Batista regime sets up kind of development institutions and financial institutions which are financed by profits from the casinos.

Speaker 33 So it's a symbiotic relationship between the regime and the mob.

Speaker 78 It's also a sort of playground for the mob in the sense that it's a bit of a free-for-all, right?

Speaker 62 It's the American mob that can kind of come down out of Chicago, New York, Vegas, and set up a new operation.

Speaker 74 So it's new turf for the mob, right? It's an expansion of their operations.

Speaker 73 And you're right, Gordon.

Speaker 56 I mean, there's this sense of Havana as really,

Speaker 64 you could think about it as the actual Las Vegas of the 1950s.

Speaker 74 This is before Vegas gets big.

Speaker 47 It's a bigger operation for the mob than Vegas in the 1950s.

Speaker 26 And there's a wonderful book on this period in Havana called Havana Nocturne by TJ English, which is all about the mob, the Batista regime, the building revolution in the countryside.

Speaker 76 And the picture of Havana at this time is

Speaker 49 insane.

Speaker 66 I mean, again, the casinos are bigger than Vegas.

Speaker 1 There are nightclubs that are sort of set in the jungle outside of Havana.

Speaker 47 It's an entertainment destination for Americans in particular, but also Europeans.

Speaker 1 It's got this fantastic nightclub scene.

Speaker 74 The nightclubs have huge orchestras.

Speaker 1 The Mambo dance craze comes out of this period in Havana.

Speaker 14 Becky, at that point, suggested I start singing Mambo number five, which I'm not going to do because it would immediately end any chance of anyone listening to the rest of this podcast.

Speaker 21 That's right.

Speaker 26 It would really tank our downloads, Gordon.

Speaker 21 So I'm glad you're not from doing that.

Speaker 8 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.

Speaker 1 Prostitution is widespread. There's lots of sex shows, private clubs, and brothels.

Speaker 52 It is a very active sexual marketplace.

Speaker 48 And you recall, Gordon, that scene, another sort of famous Havana scene in The Godfather Part II, when Michael and company go to this theater and see a fairly insane live sex show.

Speaker 41 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.

Speaker 8 The scene is actually based off of a performer who worked at this theater.

Speaker 82 His name was Superman, and he was very well known in Havana in the 1950s.

Speaker 8 I don't know why he was called Superman, Gordon.

Speaker 14 Was it because he was a mild-mannered reporter called Clark Kent by the day?

Speaker 52 Yeah, exactly.

Speaker 21 He was a reporter by day. Journalist by day.

Speaker 5 And he wore, yeah, he just put glasses on during the day.

Speaker 21 And then wear his underpants.

Speaker 14 Maybe he just wore his underpants on the outside, like Superman does.

Speaker 10 I think some tights.

Speaker 26 He was definitely wearing underpants for all of his shows.

Speaker 5 Celebrities wanted to be seen in Havana.

Speaker 52 Marlon Brando was a frequent visitor.

Speaker 66 Errol Flynn.

Speaker 55 Hemingway was kind of a local mascot in this era.

Speaker 30 He's living in Havana.

Speaker 18 Sinatra's there.

Speaker 31 JFK went in the 1950s because people went there.

Speaker 26 Americans went there.

Speaker 48 It was very common.

Speaker 75 And Batista is firmly on side in the Cold War, right?

Speaker 44 So Cuba is friendly.

Speaker 1 It's a playground.

Speaker 40 You have fun there.

Speaker 68 But all of this, as seen by ordinary Cubans, a little bit less fun.

Speaker 60 So I think this kind of wild, kind of garish nightlife is seen in some quarters in Cuba as Yankee exploitation.

Speaker 72 There is grievance, a lot of grievance building throughout the 1950s against the Batista regime.

Speaker 79 And throughout that decade, Cuba becomes a kind of tinderbox for what will eventually become Castro's revolution.

Speaker 58 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.

Speaker 60 Batista is being financed by mobsters and has turned Havana into this kind of sinful destination for predatory Yankees from the north.

Speaker 62 Also of note, the Cuban economy in this period, not doing so well for ordinary Cubans.

Speaker 34 The price of sugar falls pretty precipitously in the 1950s.

Speaker 15 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.

Speaker 26 And from this tinderbox is going to come Castro and his revolution.

Speaker 14 So a country ripe for revolution and Castro on the horizon. At that moment, let's take a break and we'll we'll come back and we'll see how revolution comes to Cuba and what that means for the CIA.

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Speaker 14 Welcome back. We've set the scene of Cuba just off the coast of the United States, a decadent place, ripe for revolution.

Speaker 14 And here comes the man, Fidel Castro, who is going to deliver that revolution and really become a thorn in the side of Washington, isn't he, David?

Speaker 54 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.

Speaker 28 And in many ways, his

Speaker 1 fate and the fate of John F.

Speaker 62 Kennedy are going to be tied together in a very kind of interesting and bizarre way.

Speaker 82 So he's an important guy to set up here.

Speaker 2 So Castro, born in 1926, 1927 in some reports, he is the illegitimate son of a wealthy landowner in eastern Cuba.

Speaker 1 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.

Speaker 36 So I think for Castro, even just growing up, he is quite literally in the shadow of Yankee imperial domination of his island.

Speaker 51 Castro studies at Havana University.

Speaker 91 He earns a law degree.

Speaker 98 And in this period in the 1940s, Havana, it is, as I mentioned earlier, a very tumultuous kind of political period in Cuban history.

Speaker 73 Castro

Speaker 86 really immerses himself in radical politics in this period of time.

Speaker 59 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.

Speaker 14 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?

Speaker 14 Rather than a communist. He's a kind of anti-imperialist, it seems to be his primary motivation from the start.

Speaker 30 There's been a lot of ink spilled about when Castro becomes a communist in ideology and spirit.

Speaker 1 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.

Speaker 47 And 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.

Speaker 2 He sees the sort of succession of weak governments in the 40s as being an extension of U.S.

Speaker 37 power and influence on the island. And

Speaker 35 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

Speaker 47 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.

Speaker 74 By the way, he earns that Doctor of Laws degree, which will lead to him having the Dr.

Speaker 21 Castro honorific that he'll carry with him for the rest of his life.

Speaker 66 Castro, as we said, he is a student radical in

Speaker 82 his time in Havana at university.

Speaker 27 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.

Speaker 56 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.

Speaker 42 Castro initially appeals the legality of canceling that election, but that, of course, doesn't go anywhere.

Speaker 29 And soon he drifts into military opposition to the regime.

Speaker 58 So in the summer of 1953, young Castro leads an attack on a Cuban army barracks.

Speaker 52 It fails.

Speaker 47 He's sentenced to 15 years in prison, but in a massive and world-changing mistake,

Speaker 34 Batista will release Fidel Castro early after serving just two years.

Speaker 46 And at this point, Batista thinks, well, the rebels' energy is kind of spent.

Speaker 30 Batista's under pressure, to some degree even from Washington, to show that he's not really a bloodthirsty dictator.

Speaker 1 And so Fidel goes out of prison in amnesty after the 1954 presidential election in Cuba, and he goes to exile in Mexico City.

Speaker 14 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.

Speaker 14 So they're kind of similar, but not quite the same. Che famous for being pictured on Student Wall.

Speaker 51 He's not just a guy from t-shirts.

Speaker 45 He's a real person

Speaker 54 in his story who helps Castro.

Speaker 6 Yes.

Speaker 74 And I think, I mean, Che in this period, of course, is a Marxist.

Speaker 55 I think, again, Castro's ideology a bit harder to pin down, but certainly drifting that direction.

Speaker 34 And in Mexico City, they join forces and raise funds to support a return and another attack on Batista in Cuba.

Speaker 53 And in December of 1956, Castro, his brother Raul, Che, and 79 others sail across the Gulf of America, Gordon.

Speaker 49 They land in Cuba, and Batista claims that Basically all the rebels, including Fidel, are killed.

Speaker 46 But, of course, they're not.

Speaker 73 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.

Speaker 34 And it slowly, over time, begins to encircle Batista in Havana.

Speaker 14 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.

Speaker 14 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.

Speaker 14 So it means that, you know, remarkably, it's a guerrilla movement which succeeds in taking the country.

Speaker 64 Yeah, and something to set up in terms of Fidel's personality is

Speaker 93 he is remarkably charismatic.

Speaker 34 He is a force of nature.

Speaker 66 He is a gifted orator and

Speaker 25 somebody that people people want to follow.

Speaker 1 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.

Speaker 72 I mean, Castro has so much going for him in this period.

Speaker 8 And also, he's going up against a brutal, U.S.-backed, mob-financed regime in Havana that is not popular at all.

Speaker 14 So by 59, he is in power. But what's so interesting is he's kind of overthrown this U.S.-backed dictator.
But actually, Washington doesn't quite know what to make of Fidel, do they, at the start?

Speaker 14 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.

Speaker 14 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.

Speaker 78 So,

Speaker 46 CIA thinks at this point: well, maybe we should get in contact with Castro.

Speaker 52 You know, he might actually establish a more representative, democratic government in Cuba.

Speaker 48 That was something that was on the table in those kind of early months in 1959 as Castro is taking power.

Speaker 57 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?

Speaker 55 He orders the execution pretty much right after taking Havana of more than 500 Batista supporters who are shot.

Speaker 14 Can't have a revolution without firing squads, as Lenin would say.

Speaker 10 Right.

Speaker 31 And so at this point, you have maybe some hope that the U.S.

Speaker 47 can work with Castro and also a sense that, well, this is not going to be a particularly peaceful takeover.

Speaker 92 Now, Castro actually visits.

Speaker 19 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.

Speaker 7 And it's a wild trip, Gordon.

Speaker 47 Castro is generally quite amiable.

Speaker 91 He's greeted by well-wishers everywhere.

Speaker 38 He meets a raft of very senior U.S.

Speaker 54 officials.

Speaker 31 The acting Secretary of State, he spends two and a half hours with then Vice President Richard Nixon.

Speaker 62 He shakes Jackie Robinson's hand.

Speaker 6 Jackie Robinson, of course, famous for breaking the color barrier and being the first African-American to play Major League Baseball.

Speaker 61 Fidel Castro, you know, plays with school kids.

Speaker 48 He's kind of embraced by elements of American society and certainly by the kind of growing American counterculture at that point in time.

Speaker 54 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.

Speaker 49 He knows what's hip and bugs the squares.

Speaker 72 That's essentially a 1950s version of a Che Guevara t-shirt at that point.

Speaker 14 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.

Speaker 14 He's this kind of, you know, cool, revolutionary, younger generational figure, isn't he?

Speaker 31 That's right.

Speaker 1 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 as a common novelty item in America that spring.

Speaker 25 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.

Speaker 30 And he's asked this question constantly on the trip to New York. Are you a communist, Dr.

Speaker 67 Castro?

Speaker 83 Are you a communist?

Speaker 52 And he says he's not.

Speaker 35 He refutes the idea that he's a card-carrying communist.

Speaker 77 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?

Speaker 79 And Gordon, a CIA officer, meets Castro during this trip and actually sits down with him 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.

Speaker 21 Brilliant piece of CIA analysis.

Speaker 76 Great piece of analysis.

Speaker 10 That from a McCloskey that many McCloss

Speaker 69 failed the brief.

Speaker 14 Yeah, he did not get his analysis right.

Speaker 59 And well, it is true that unlike his brother Raoul, Fidel has not been in the Communist Party.

Speaker 3 He doesn't yet have a relationship with the Soviet Union.

Speaker 1 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 incredibly naive about communism and the strength of sort of communism inside his own government, or he's under communist discipline.

Speaker 47 And essentially, I think Nixon is saying, like, we have to kind of deal with him as though he is a communist.

Speaker 14 I think what's interesting is as his regime starts to take shape back in Cuba, he starts to do things which are against

Speaker 14 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 communists, you'll say is 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.

Speaker 14 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 this point.

Speaker 8 No, not necessarily.

Speaker 40 And I think even as Castro starts appropriating, you know, American investments to the tune of hundreds of millions of dollars in Cuba.

Speaker 41 You're right, Gordon.

Speaker 64 I mean, you could spin a story that he is just a nationalist who wants Cuba to be much more independent.

Speaker 52 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.

Speaker 2 And loads of American mobsters are essentially kicked out of Havana and lose their shirts in the process.

Speaker 47 I mean, a lot of these organizations had invested considerable sums in setting up and running these casinos and hotels, and they are basically shoved out and not compensated for it.

Speaker 47 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.

Speaker 72 And Castro, I mean, to your point on sort of, you know, is he a nationalist?

Speaker 64 I mean, he pursues land reform, which, again, is that, are you communist or are you just a Cuban nationalist?

Speaker 1 Which, of course, makes the American owners of big sugar mills and plantations and cattle ranches extremely anxious.

Speaker 5 He's imprisoning, Castro's imprisoning thousands of Cuban citizens, some with very close ties to the U.S.

Speaker 60 The executions continue.

Speaker 35 So, Castro is building a pretty diverse set of enemies in the United States.

Speaker 76 So, you have a kind of growing exile community of Cubans that have gone to Florida, in particular, Miami.

Speaker 15 There's just a steady flow and are still there.

Speaker 45 You have American corporate interests, where you have properties that have been nationalized.

Speaker 76 You have the mob.

Speaker 64 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, at this point in the Cold War, you don't have any sort of communist stronghold that close to the U.S.

Speaker 46 and the Western hemisphere.

Speaker 66 So this is a new and very threatening development.

Speaker 14 And of course, the U.S.

Speaker 14 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.

Speaker 14 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?

Speaker 43 No, it's not.

Speaker 64 I think the KGB, the Soviets, are also trying to feel out Castro in this period.

Speaker 1 There is a connection that begins pretty soon after he takes Havana between Castro's security services and the KGB.

Speaker 36 Communist influence, I think, though, over the course of 1959, does become more apparent inside Castro's regime.

Speaker 72 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.

Speaker 73 So if you're writing the analysis, you can start to build a picture of this is a communist takeover.

Speaker 44 And in resistance to this, a spate of anti-Castro terror begins in Havana and around Cuba with Cubans starting to resist.

Speaker 29 There are department stores in Havana that are bombed.

Speaker 37 There's a ship in Havana Harbor that's blown up, that kills more than 100.

Speaker 30 Sugar plantations are burned.

Speaker 84 You have, as we said, this growing exile community that's fleeing and coming to Florida.

Speaker 33 And amid all of this, I think the Eisenhower administration is looking at this and saying, what is the Cuba policy going to be?

Speaker 81 So in October of 1959, Eisenhower tasks the State Department to come up with that policy.

Speaker 30 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.

Speaker 14 Which makes it sound like a job for the CIA.

Speaker 52 It is a job for the CIA, Gordon.

Speaker 21 I thought you'd never say it.

Speaker 69 I thought we'd never get there.

Speaker 14 If you want to encourage it, it's a job for the CIA. But without giving the impression of direct pressure.

Speaker 14 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.

Speaker 90 It is. It is.
And of course,

Speaker 74 so the State Department writes the words.

Speaker 47 The CIA is going to do it.

Speaker 5 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,

Speaker 94 because the CIA of the 1950s is very different from the Central Intelligence Agency of today, as we'll see.

Speaker 21 That's okay, Gordon.

Speaker 32 For those who didn't hear that faint noise that Gordon made, that was a sound of incredible skepticism.

Speaker 14 Deep state endures.

Speaker 21 Yeah, exactly.

Speaker 47 And a sign of maybe Gordon's trip down the rabbit trail of conspiracy.

Speaker 71 So the CIA.

Speaker 84 At this point in time in the late 1950s, is a very young organization.

Speaker 1 It's been around only since 1947.

Speaker 5 It is full of white Anglo-Saxon Protestants,

Speaker 67 wasps,

Speaker 2 skull and bones types, guys who graduated from Yale.

Speaker 76 You've compared them before to which

Speaker 21 the Bullingdon Club.

Speaker 14 Yeah, the Bullingdon 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.

Speaker 14 But it's a kind of elite crowd, isn't it? Slightly entitled, some people might say.

Speaker 52 Just slightly, yes.

Speaker 74 So I think there's four things to know about the CIA of this period.

Speaker 86 One, to this point on kind of wasp-y skull and bones types.

Speaker 77 it is staffed with rich, well-connected white guys who'd spent a lot of the Second World War blowing things up all over Europe.

Speaker 47 Okay, so this is full of OSS, Office of Strategic Services guys whose experience in intelligence is destroying Nazi railroads and supply depots, right?

Speaker 91 So this is an organization of

Speaker 69 covert action, you could say, where it's a little bit less,

Speaker 62 let's just kind of get some

Speaker 10 about the world. Yeah.
Yeah. Yeah.
Yes.

Speaker 14 Led by Alan Dulles.

Speaker 76 Yes, friend of the pod.

Speaker 14 He is the leader of the CIA at this point and is going to be a big figure, I think, in our story and actually in some of the theories.

Speaker 14 I'm not going to call them conspiracy theories involving the CIA and JFK, which we'll end up coming to.

Speaker 14 Because 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 II.

Speaker 14 He'd been a corporate lawyer, I think, you know, had 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.

Speaker 14 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.

Speaker 14 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.

Speaker 14 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.

Speaker 14 And even if we go back to Iran, you know, oil is part of the motivation.

Speaker 14 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?

Speaker 31 Well, you've kind of said this in sneering tones, which

Speaker 31 makes it sound diabolical.

Speaker 5 I mean, I don't disagree.

Speaker 1 I think it's just a happy alignment of geopolitical and corporate interests that just so happen to be connected.

Speaker 65 You know, I mean, you can have instances where a country's geopolitical or security interests sort of conflict with its corporate interests.

Speaker 43 And in this case, we just have a wonderful example of alignment between Washington and giant U.S.

Speaker 26 conglomerates, Gordon.

Speaker 52 It feels, I mean, what's more innocent than that, right?

Speaker 14 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.

Speaker 14 Also worth saying that his brother, John Foster Dulles, is the Secretary of State. I mean, it is amazing.

Speaker 14 One brother as Secretary of State and the other brother as running the CIA through the 50s under Eisenhower. It's amazing, really.

Speaker 36 It's efficient, you know? Keep it in the family.

Speaker 82 And then, you know, later in the story, of course, we'll have JFK and then his brother RFK will be the Attorney General.

Speaker 77 So we've got distinguished brothers left and right in this story.

Speaker 34 Now, I only said, Gordon, that Alan Dulles was a friend of 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, uncharitably described as a CIA coup in Iran that Dulles was involved in.

Speaker 1 Now, Dulles, just from a character standpoint, he likes a tweed suit and a pipe.

Speaker 91 He has a remarkable libido.

Speaker 60 He's a notable philanderer.

Speaker 75 He probably has an affair with the queen of greece at work in his in his office.

Speaker 92 He does not look like a sinister spy master.

Speaker 52 He looks like a kind of grandfatherly figure, I would say.

Speaker 47 And you're right that he is a feature of this story and really an embodiment, I think, of the Central Intelligence Agency by the time we get to the Kennedy administration.

Speaker 6 We should also say, so that's point one on the agency.

Speaker 58 It's staffed with guys like Dulles.

Speaker 52 Two, is that there really isn't any congressional oversight in this period.

Speaker 1 So there isn't much of a check on the executive branch's control over the CIA.

Speaker 47 And there's a great

Speaker 64 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.

Speaker 1 And Dulles would go and ask for money.

Speaker 62 They would usually give it to him.

Speaker 15 And Dulles would say, I think, Mr.

Speaker 47 Chairman, I've asked for as much as I can spend wisely.

Speaker 30 If I get into trouble, I'll come back to your committee.

Speaker 60 And the congressman would bang his gavel and say, Meeting adjourned, and that was that.

Speaker 47 So, there is a very loose congressional hand over the Central Intelligence Agency at this period.

Speaker 79 So, that's two.

Speaker 48 Three is the CIA is charged with rolling back communist influence worldwide without triggering a third world war.

Speaker 1 And it functions in many respects as the kind of executive action arm of the White House.

Speaker 90 And a reporter reporter once asked Dulles, what is the CIA?

Speaker 40 And he said, it's the State Department for unfriendly countries.

Speaker 14 That's such a good quote.

Speaker 31 So countries where we might have to do some stuff to make them more amenable to U.S.

Speaker 1 interests.

Speaker 47 That's when the CIA in this period gets involved.

Speaker 14 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 U.S.

Speaker 14 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.

Speaker 14 And I think for that reason, I think it feels like

Speaker 14 he does give Dulles and the CIA a lot of latitude. And I think as he comes to the end of his presidency, he possibly thinks too much latitude.

Speaker 14 I think that's one of the things he might think in Eisenhower's case. But certainly, COVID action becomes quite intrinsic to U.S.
policy in this period under Eisenhower.

Speaker 7 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 it basically destroyed the European continent and much of Asia and resulted in the dropping of nuclear bombs on Japan.

Speaker 8 So

Speaker 42 they are trying to avoid that at all costs.

Speaker 44 And covert action in this period, and 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.

Speaker 81 These were unwise.

Speaker 88 They were all being crafted by guys like Dulles and Eisenhower and many of the other characters that we'll 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.

Speaker 47 They're trying to use the CIA to roll that influence back without getting everybody into a total war.

Speaker 1 So Eisenhower, I think, becomes very enamored with using the CIA for covert action purposes because you could conceivably avoid that total war.

Speaker 73 You don't have to be overt with the way you're using, you know, U.S.

Speaker 44 power and prestige.

Speaker 10 And I think Eisenhower also, Gordon, would have seen,

Speaker 3 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.

Speaker 45 at work in the Second World War.

Speaker 1 I mean, the breaking of German codes, Eisenhower would have understood the value that an intelligence service could play in winning a conflict.

Speaker 86 And I think just turns more and more to the central intelligence agency throughout his term.

Speaker 14 But he's not going to be shy of using the most aggressive tools, as we'll see.

Speaker 60 Well, that's right.

Speaker 97 And fourth,

Speaker 60 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, right?

Speaker 47 It is literally sprawling into new real estate.

Speaker 89 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.

Speaker 74 So it's being, throughout most of our story, the headquarters building is being constructed.

Speaker 47 It is a 258 acre campus with a million square feet of office space that makes it in terms of sort of U.S.

Speaker 1 government office space only second in size next to the Pentagon.

Speaker 25 And it's massive.

Speaker 47 There's a 500-seat auditorium.

Speaker 1 There's a cafeteria that can accommodate a thousand people.

Speaker 8 There's a 3,000-car parking garage.

Speaker 1 So American intelligence has gone in the span of a decade from a really,

Speaker 30 really small elite enterprise to part of the Washington sort of bureaucratic establishment by the end of the 1950s.

Speaker 14 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.

Speaker 14 And then there is Castro in Cuba, just off the U.S. coast.
And I mean,

Speaker 14 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.

Speaker 66 Yeah, and, you know, it's interesting.

Speaker 64 The CIA, now looking back at this period, I think...

Speaker 76 gets a bit of a bad rap, Gordon,

Speaker 49 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.

Speaker 66 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.

Speaker 64 The State Department, of course, had developed that policy.

Speaker 60 And throughout 1959, though, the agency is assessing that while Castro is drifting left, he's tolerating communists rather than embracing them.

Speaker 55 So the national intelligence estimates that are produced in that period run a a bit counter to the State Department's or the assumptions underlying the State Department's policy.

Speaker 10 And as late as November of 59, so after the State Department has essentially said U.S.

Speaker 90 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.

Speaker 26 So the CIA is, I think, slowly, or maybe more slowly, than some of the other arms of government coming to terms with Castro as a communist.

Speaker 1 Now, Dulles in this period is quite old.

Speaker 52 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.

Speaker 53 Much of the work on Cuba is going to fall to Dulles' deputy director for plans.

Speaker 73 Richard Bissell.

Speaker 3 Now, the deputy director for plans is essentially the equivalent of the deputy director for operations today.

Speaker 84 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?

Speaker 53 Now, Richard Bissell is Dick to his colleagues and Dickie to his friends.

Speaker 42 And I think a new friend of the pod will refer to him as Dickie

Speaker 52 in these episodes. Dickie Bissell.

Speaker 31 Now, Bissell is a 1950s CIA officer out of Central Casting.

Speaker 62 He is this kind of brilliant character.

Speaker 64 He's raised in a wealthy Connecticut family.

Speaker 26 He actually grows up in Mark Twain's old house.

Speaker 1 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.

Speaker 10 Wow.

Speaker 81 And 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.

Speaker 78 Dickie Bissell graduates from Groton and where else?

Speaker 88 Yale.

Speaker 1 He works for the Marshall Plan, where he was a deputy assistant administrator, which doesn't sound that interesting, but it meant that quite literally he controlled the flow of cash that rebuilt Europe.

Speaker 78 So Dickie Bissell basically was the purse strings for the Marshall Plan.

Speaker 1 He works for the Ford Foundation.

Speaker 30 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.

Speaker 14 And live in an area called Georgetown, just in the Georgetown area.

Speaker 46 features people like Catherine Graham, who's the publisher of the Washington Post at the time.

Speaker 37 The elite.

Speaker 76 Yeah, the elite.

Speaker 65 Now, he also likes to sail.

Speaker 77 He's got a 54-foot sailboat that he sails off the coast of Maine.

Speaker 27 He tours in Europe.

Speaker 89 He's also got manic energy, Gordon, and I think really is the epitome of the 1950s CIA man, this kind of, you know, PhD who could win a bar fight.

Speaker 63 He paces incessantly.

Speaker 5 He charges down hallways.

Speaker 52 When he's sitting, he's always, his hands are always moving.

Speaker 15 He's, you know, twisting paper clips and throwing pencils.

Speaker 47 He's kind of got this bundle of nervous energy.

Speaker 31 Dickie Bissell has wound up at the CIA because he befriended Alan Dulles.

Speaker 78 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.

Speaker 44 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.

Speaker 95 I actually don't think that Dickie Bissell was a W-2 employee of the Central Intelligence Agency in this period.

Speaker 53 He was like a contractor who had been brought in by Dulles to run a covert action program in Guatemala.

Speaker 14 Yeah, to overthrow a government on behalf of a U.S. corporation, United Troop, basically.
It's a very interesting story. We should do that one another time.

Speaker 14 But I think we're getting a picture of this slightly aggressive,

Speaker 14 confident operator, basically.

Speaker 33 He's also extremely competent.

Speaker 85 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.

Speaker 1 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.

Speaker 3 And by early 1959, he is Dulles' deputy director for plans.

Speaker 25 And if...

Speaker 35 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.

Speaker 55 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.

Speaker 93 And he is

Speaker 68 remarkably stubborn.

Speaker 35 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.

Speaker 1 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.

Speaker 93 He is confident.

Speaker 31 He's very persuasive, very persuasive in meetings, which is also going to be really important.

Speaker 14 Domineering, perhaps.

Speaker 60 Domineering, yes.

Speaker 14 Blind spots.

Speaker 7 And he's got real blind spots.

Speaker 64 And the man who will become JFK's national security advisor, McGeorge Bundy, and who is actually a friend of Bissell's 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.

Speaker 65 So we've got this really

Speaker 32 competent, aggressive, stubborn guy full of manic energy who is going to be essentially put in charge of the cubophile at the CIA.

Speaker 8 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, Bissell sends Alan Dulles a memo suggesting that, quote, thorough consideration be given to the elimination of Fidel Castro.

Speaker 31 And then Dulles, looking at this, pencils in a correction.

Speaker 47 He strikes out elimination and replace, which I think elimination kind of suggests that you are going to kill him.

Speaker 27 So Dulles replaces it with removal.

Speaker 84 And so, right away, we have this idea of assassinating Fidel bubbling up to the surface of the CIA's thinking.

Speaker 36 It's put on the back burner, but planning is going to begin in earnest to orchestrate the overthrow of Fidel Castro.

Speaker 14 So, there, with plans for elimination or removal of Fidel Castro and his beard by the CIA,

Speaker 14 we're going to leave it next time.

Speaker 14 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 invasion, as it's called.

Speaker 14 And we'll also look at how that in turn feeds in to the Kennedy presidency and to the questions of who really killed JFK.

Speaker 31 But of course, if you don't want to wait for that episode, you can join the Declassified Club, go to therestisclassified.com, become a member.

Speaker 1 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.

Speaker 62 Kennedy.

Speaker 30 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.

Speaker 30 Kennedy. So go and join the club at therestisclassified.com.

Speaker 49 We'll see you next time.

Speaker 14 See you next time.

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