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

Summary

The Rest Is Classified

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

Air Date: October 12, 2025
Hosts: David McCloskey (former CIA analyst, spy novelist), Gordon Corera (veteran security correspondent)

Overview

In this first episode of a six-part series, McCloskey and Corera launch a deep exploration of the fraught and fateful relationship between President John F. Kennedy’s White House and the CIA, with Cuba as their battlefield. Through detailed storytelling and vivid historical context, the hosts unpack how Cold War intrigue, covert action, and government-mob collusion intertwined—and how these dark currents ultimately shaped American politics, culture, and enduring conspiracy theories around JFK’s assassination.

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Key Themes and Episode Structure

• The Explosive Relationship: JFK, the CIA, and the mission to overthrow Castro
• Setting the Stage: Pre-revolutionary Cuba—American playground, mob haven
• Castro’s Rise: Nationalism, radicalism, and the anti-American pivot
• America’s Dilemma: From cautious engagement to covert action and regime change
• The CIA in the 1950s: WASPish elites, unchecked power, and the birth of covert operations
• Seeds of Conspiracy: How Cold War schemes morphed into enduring public suspicion

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Detailed Summary & Discussion Points

The Stakes: Cuba Becomes Washington’s Obsession

• [00:56] David McCloskey: “Cuba itself is really quickly going to become the Kennedy administration’s top priority.”
• The episode opens with archival audio on JFK’s death, setting a somber tone of historical consequence.
• The hosts highlight Cuba as the unexpected “epicenter” of Cold War rivalry, capturing Kennedy’s, the CIA’s, and the mob’s competing interests.

Setting the Tone: The Godfather II Parallel

• The hosts dramatize a scene from The Godfather Part II to underscore real-life collusion between the US government, exiled mobsters, and intelligence agencies targeting Castro.
  • [03:56] David McCloskey: “All these mobsters have been shoved out of Havana, lost all their money, 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.”

Cuba Before Castro: The American-Mob Playground

• Geographical proximity: Cuba is only 90 miles from Key West, a fundamental factor in US foreign policy fears ([11:45]).
• Historical control: Extensive political and economic domination by the US since the Spanish-American War.
• Mob influence: Havana in the 1950s rivaled Las Vegas as a hub for American mob bosses, casinos, and vice.
  • [15:50] David McCloskey: “The Batista regime has struck a deal with the American mob...it’s a symbiotic relationship between the regime and the mob.”
  • [16:51] Gordon Carrera: “It’s a kind of playground for the mob, isn’t it...a decadent, particularly Havana in the 50s, in which it is pretty wild.”
• Cultural iconography: The mob’s power, debauchery, and celebrity allure made Havana “the actual Las Vegas of the 1950s” ([17:10]).

Batista, Corruption, and the Cuban Grievance

• US-backed dictator Fulgencio Batista is portrayed as “fabulously corrupt,” pocketing millions, and maintaining power through violence and mob money ([15:32], [15:50]).
• The reality of “Yankee exploitation” and economic hardship sows deep anti-American resentment and primes the island for revolution ([19:53]).

Castro’s Biography and Revolutionary Charisma

• Early life as a nationalist, shaped by direct experience of American corporate dominance ([22:58]).
• [24:28] Gordon Carrera notes: Castro was more a nationalist and anti-imperialist than a committed communist at first.
• Prison, exile, alliance with Che Guevara, and a daring return to lead a successful guerrilla war against Batista ([28:30]).
• [28:54] David McCloskey: “He is remarkably charismatic. He is a force of nature. He is a gifted orator and somebody that people want to follow.”

Washington’s Initial Ambivalence Towards Castro

• On gaining power, Castro becomes an American media darling—embraced even by elements of the counterculture ([32:22]).
• [32:33] David McCloskey: “Spring of 1959...you might have given them a costume Fidel beard made from treated dog or fox hair. That was a common novelty item in America.”
• CIA officers initially doubt that Castro is truly a communist, reflecting confusion within the US government ([33:51]).

The Turn: Nationalization, Mob Fury, Rising Tensions

• As Castro nationalizes US assets and kicks out the mob, he gains potent enemies among American business, organized crime, and anti-communist officials.
• The US policy quietly shifts, culminating in a State Department strategy to “encourage and coalesce opposition” to Castro while avoiding open intervention ([39:29]).

Notable Quote

• [46:48] David McCloskey (quoting Dulles):
  “What is the CIA? ...It’s the State Department for unfriendly countries.”
  (An encapsulation of the CIA’s covert-action ethos.)

Introducing the 1950s CIA: Culture, Power, and Agency

• Elites in charge: Led by Allen Dulles and staffed by Yale/Bullingdon types, the CIA is portrayed as a clubby, energetic old-boys’ network with minimal oversight.
  • [40:17] Corera’s skeptical sighs: “A deep state endures.”
  • [43:28] Corera: “There is this sense in which Allen Dulles is emblematic of a certain type of American elite and a certain view of the world and of what the CIA should do.”
• Unchecked authority: Congress offers little interference; executive branch directs policy.
• Mission: Roll back communism covertly, not through open war—using coups, subversion, and assassination as tools.
• Rapid growth: By the end of the 1950s, the agency is “sprawling” both in real estate and influence ([49:47]).

Shifting Towards Regime Change

• The State Department’s covert directive leads the CIA into plotting against Castro, even as agency assessments lag in calling him a communist ([51:29]).
• Enter Richard “Dickie” Bissell—a quintessentially elite, energetic CIA operator, becomes the architect of anti-Castro covert action.
  • [54:37] McCloskey: “He’s full of manic energy...a PhD who could win a bar fight.”
• Assassination discussions: By late 1959, Bissell formally suggests considering “elimination” of Castro; Dulles tones it down to “removal” ([57:31]).
  • The seeds for the CIA’s involvement in plots against Castro are sown, a thread that will later reappear in JFK conspiracy theories.

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Notable Quotes and Memorable Moments

| Timestamp | Quote | Speaker |
|:---:|---|---|
| 03:56 | “What better way...than to read from the Godfather Part 2...It sets the tone for this, this whole series about this insane chapter in the Agency's history.” | McCloskey | | 08:59 | “So much of the talk about what the CIA could do is shaped by what’s come out through the stories related to JFK.” | Carrera | | 15:50 | “The Batista regime has struck a deal with the American mob...a symbiotic relationship between the regime and the mob.” | McCloskey | | 24:28 | “He’s primarily a nationalist at this point, isn’t he, rather than a communist?” | Carrera | | 32:33 | “If you were looking for a great party gift to give someone, you might have given them a costume Fidel beard...” | McCloskey | | 46:48 | “What is the CIA? ...It’s the State Department for unfriendly countries.” | McCloskey (quoting Dulles) | | 54:37 | “He’s full of manic energy...a PhD who could win a bar fight.” | McCloskey (on Bissell) |

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Timestamps for Major Segments

• 00:56–04:55 — Setting the Series: Why Cuba? Godfather II analogy
• 11:45–21:53 — The pre-revolutionary Cuba: US dominance, mob rule, economic background
• 22:58–28:30 — Castro’s emergence, background, and revolutionary victory
• 29:38–35:21 — US confusion: How do we handle Castro? The “cool” rebel; business losses and growing hostility
• 39:29–46:47 — US policy shift: Quiet regime change, CIA empowerment
• 46:47–54:37 — CIA of the 1950s: Personnel, mission, lack of oversight, growth
• 54:37–58:58 — Richard Bissell and the move toward covert action and assassination plots

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Tone & Style

• Conversational and witty, yet precise: The hosts blend narrative history with wry asides and references to pop culture.
• Insider’s insight: McCloskey lends first-hand CIA experience; Corera offers journalistic skepticism.
• Directly engaging the audience: Frequent invitations to question official narratives and explore deeper conspiracy theories.

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Closing & What’s Next

The episode concludes with the hosts teeing up the coming installments: the disastrous Bay of Pigs invasion, the unraveling of US-Cuba relations, and a descent into the assassination plots and cover-ups that forever changed American history.

[58:58] Gordon Carrera: “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 invasion…”

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For Further Exploration

• Exclusive miniseries for Declassified Club members delving into the JFK assassination and related theories, featuring guest Anthony “The Mooch” Scaramucci.
• Book recommendation: Havana Nocturne by T.J. English for a deeper dive into the Havana mob scene.

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Summary prepared for listeners new to the podcast or this series, highlighting all major themes, events, and characters in the episode—while capturing the spirit, tone, and texture of the hosts' discussion. Advertisements, audio distractions, and non-content sections have been omitted for clarity.

Transcript

[David McCloskey]

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@the restisclassified.com hey, Ryan.

[Ryan Reynolds]

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[David McCloskey]

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[Ryan Reynolds]

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[David McCloskey]

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[The Flash (Narrator/Archive Voice)]

See mintmobile.com from Dallas, Texas, the Flash. Apparently official President Kennedy died at 1:00pm Central Standard Time.

[David McCloskey]

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

[The Flash (Narrator/Archive Voice)]

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

[Gordon Carrera]

At the end of the day, the US is facing off against this tiny island, Cuba. How could you lose?

[The Flash (Narrator/Archive Voice)]

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

[David McCloskey]

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

[The Flash (Narrator/Archive Voice)]

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

[Gordon Carrera]

The CIA were kind of playing jfk.

[David McCloskey]

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

[The Flash (Narrator/Archive Voice)]

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

[David McCloskey]

Everything that could go wrong does out.

[Gordon Carrera]

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

[The Flash (Narrator/Archive Voice)]

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

[Gordon Carrera]

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

[David McCloskey]

That was the past.

[Gordon Carrera]

Don't give up on Cuba. Not yet.

[David McCloskey]

Why not?

[Gordon Carrera]

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

[David McCloskey]

We have different agendas, but we have the same goal.

[Gordon Carrera]

And we have the same resources, intelligence. The only thing we don't have is a way to get inside.

[David McCloskey]

Anyone can get inside Cuba. Smugglers do it all the time.

[Gordon Carrera]

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.

[David McCloskey]

And what's this someone gonna do?

[Gordon Carrera]

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.

[David McCloskey]

And I'm David McCloskey.

[Gordon Carrera]

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 2. And why are we using that legendary scene, David?

[David McCloskey]

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 Garleoni 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 an 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, 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.

[Gordon Carrera]

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 decades 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, and Cuba being the critical aspect which shapes this relationship and which actually strange how that one island is going to shake JFK, the 35th President of the United States. Whole time as president, his, his career is death. And the questions around his assassination all kind of revolve around the CIA and Cuba, I think.

[David McCloskey]

Yeah. And we should say, Gordon, we have a very special surprise for listeners. For the first time on the Rush is Classified, we are going to 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 you want to listen to that exclusive miniseries, make sure you're signed up for the club@the restisclassified.com to get access to those episodes when they go live. Because the story we're gonna 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 gonna look at each of those theories in that exclusive miniseries for our club members.

[Gordon Carrera]

I mean, that's right. It's a story about COVID 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.

[David McCloskey]

You've lost your mind. You've become.

[Gordon Carrera]

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 tinfoil.

[David McCloskey]

Hat, but maybe I will be soon.

[Gordon Carrera]

Maybe you might be soon, Gordon. I might be there soon. I'm on the way.

[David McCloskey]

We're going to talk about a story from the late 1950s and early 1960s, right up until the point where John F. Kennedy is assassinated in Dallas. And, and that time period, 60 plus years later has incredible resonance 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% after Oliver Stone's movie JFK comes out in the early 1990s, which I've been 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 unspecified, that's about 20%. And then the CIA at 16%. Right. And then another 11% think the mafia or 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 US Government about what happened in the Kennedy assassination. It is alive and well today.

[Gordon Carrera]

Yeah. And I think what's so interesting about it is it, it's not just alive as a theory, but it has 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. 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. 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, 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 COVID action and some of the things that we're particularly interested in in this show.

[David McCloskey]

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 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 in just digging into this has been there's kind of an official narrative and we'll, 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 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 COVID 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.

[Gordon Carrera]

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?

[David McCloskey]

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 US 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 looked 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, it is very, very close.

[Gordon Carrera]

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.

[David McCloskey]

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, 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 it American military governor. A few years later, actually in 1903, something called the Platt Amendment granted Cuba limited self rule. But it gave the US a 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.

[Gordon Carrera]

I've visited three times, so weird way of seeing Cuba.

[David McCloskey]

But yeah, that is a weird way of seeing Cuba. You've, you've earned a lot of points in your Guantanamo Bay stays, Gordon?

[Gordon Carrera]

I have, yeah.

[David McCloskey]

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 US influence and control is very significant. And the US landed troops on the island whenever Washington perceived its interests 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 owned. And 80% of Cuban imports came from the US 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 Fulgencio 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 US 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.

[Gordon Carrera]

Big mustache.

[David McCloskey]

I don't. I don't know if the mustache game was exactly what you're expecting, Gordon. In the pictures I've seen, he's not very well mustachioed.

[Gordon Carrera]

Okay.

[David McCloskey]

But those could be dated photos. By the 50s, he could have been rocking a strong mustachio game.

[Gordon Carrera]

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

[David McCloskey]

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 II is based on a real life mobster named Meyer Lansky who was one of the controlling mobsters in havana in the 1950s. And that 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 essential. Just a Documentary because it is a.

[Gordon Carrera]

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.

[David McCloskey]

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 free for all. Right? 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. It's an expansion of their operations. And you're right, Gordon. I mean, this. 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 Nocturne 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. 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.

[Gordon Carrera]

Becky, at that point, suggested I start singing Mambo Number five, which I'm not going to do because it immediately ends. Any chance of anyone listening to the rest of this podcast.

[David McCloskey]

It would really. It would really tank our downloads, Gordon. So I'm glad you. I'm glad you've heard that. Let's not do that 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 ii 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.

[Gordon Carrera]

Was it because he was a mild mannered reporter called Clark Kemp by the day?

[David McCloskey]

Yeah, exactly. He was a reporter by day, journalist by day. That's a good point. Yeah. And he wore, yeah, he just put glasses on during the day and, and.

[Gordon Carrera]

Then wear his underpants. Maybe he just wore his underpants on the outside like super does outsides.

[David McCloskey]

He was definitely wearing underpants for all of his shows. Celebrities wanted to be seen in Havana. Marlon Brando was a, 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 is very common. And Batista is firmly onside in the Cold War. Right. So Cuba's friendly, it's, it's a playground. You have fun. There's 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 US 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 postcolonial movements that are erupting all over the world, gaining momentum. And from this tinderbox is going to come Castro and his revolution.

[Gordon Carrera]

So a country ripe 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.

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[Gordon Carrera]

Welcome back. We've set the scene of Cuba just off the coast of the United States, a decadent place ripe 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, isn't he, David?

[David McCloskey]

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.

[Gordon Carrera]

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 start.

[David McCloskey]

There's been a lot of ink spilled about when Castro becomes a communist in, in ideology and spirit. And I, 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 regiment. 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 Laws 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, he is a student radical in his, 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 US 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, 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 rebel's 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.

[Gordon Carrera]

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.

[David McCloskey]

He's not just a guy from T shirts, he's a real guy. He's a real person 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 claims 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.

[Gordon Carrera]

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 and Che were kind of offering this vision of change. So it means that, you know, remarkably, it's a guerrilla movement which succeeds in taking the country.

[David McCloskey]

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, 50s with this push toward sort of postcolonialism and, 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 US backed mob financed regime in Havana that is not popular at all.

[Gordon Carrera]

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 they? 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 the, those early days about how to see him?

[David McCloskey]

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, 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 taken 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.

[Gordon Carrera]

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

[David McCloskey]

Right. And so at this point you have maybe some hope that the US 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 US 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 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 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.

[Gordon Carrera]

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?

[David McCloskey]

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 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.

[Gordon Carrera]

So brilliant piece of CIA analysis, great.

[David McCloskey]

Piece of analysis that from a McClosmy McLoss failed the brief, right?

[Gordon Carrera]

Yeah, he did not get his analysis right.

[David McCloskey]

And well, it is true that unlike his brother Raul, 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 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.

[Gordon Carrera]

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 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 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.

[David McCloskey]

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, 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 in 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, 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, are you 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, 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. 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, at this point in, in the Cold War, you don't have any sort of communist stronghold that close to the US in the Western hemisphere. So this is a new and very threatening development.

[Gordon Carrera]

And of course, the US views this as its hemisphere and, 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?

[David McCloskey]

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 security services and the KGB. Communist influence, I think 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, 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 their department stores in Havana that are bombed. There's a ship in Havana harbor that's blown up, that kills. More than a hundred sugar plantations are burned. You have, as we said, this, 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.

[Gordon Carrera]

Which makes it sound like a job for the CIA.

[David McCloskey]

It is a job for the CIA. Gordon. I thought you'd never say it. I thought we'd never get there.

[Gordon Carrera]

If you want to encourage opposition but without giving the impression of direct pressure, I wonder which part of the US government that will fall to. I think it's time for the CIA to enter the story properly.

[David McCloskey]

It is, it is. And of course, you know, 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, for those who didn't hear that faint noise that Gordon made, that was a, a sound of incredible skepticism.

[Gordon Carrera]

A deep state endures.

[David McCloskey]

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.

[Gordon Carrera]

Wasps.

[David McCloskey]

Wasps. Skull and bones types. Guys who graduated from Yale. You've compared them before. To which the Bullingdon Club.

[Gordon Carrera]

Yeah. The BUL 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.

[David McCloskey]

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'd 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 COVID action, you could say, where it's, it's a little bit less. Let's just kind of get cerebral. The world.

[Gordon Carrera]

Yeah, yeah, yeah.

[David McCloskey]

Yes.

[Gordon Carrera]

Led by Alan Dulles.

[David McCloskey]

Yes. Friend of the pod.

[Gordon Carrera]

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, I'm not going to call them conspiracy theories involving the CIA and jfk, which we, which will end up coming to. Because I think we should just spend a moment on Dulles because he is kind of emblematic, isn't he, of that kind of crowd who are from the elite who've served in World War II. He'd been a corporate lawyer, I think, you know, had been his background in the, 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 at 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, including the United Fruit Company. We mentioned 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 Allen 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.

[David McCloskey]

Well, you've kind of, you've said this in sneering tones, which makes me, makes it Sound diabolical. I mean, I don't disagree. I think it's just a happy alignment of geopolitical and corporate interests that just so happen 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?

[Gordon Carrera]

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

[David McCloskey]

It's efficient. It's, keep it in the family. And then later in the story, of course, we'll have jfk, and then his brother rfk, will be the attorney General. So we've got distinct 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, uncharitably described as a CIA coup in Iran that Dulles was involved in. Now, Dulles, just from a character standpoint, he likes a tweed suit and 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.

[Gordon Carrera]

He looks.

[David McCloskey]

He looks like a kind of grandfatherly figure, I would say. And you're right that he's. He's. 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, we. 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. There's a great story from one of Dulles's administrative aides where he basically says that when Dulles would brief Congress, because they would. 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 once asked Dulles, what is the CIA? And he said, it's the State Department for unfriendly countries.

[Gordon Carrera]

That's such a good quote.

[David McCloskey]

So countries where we might have to do some stuff to make them more amenable to US Interests. That's when the CIA in this period gets involved.

[Gordon Carrera]

And I find it very interesting because under Eisenhower, 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 COVID 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 it 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 presidency, he possibly thinks too much latitude. I think that's one of the, the things he might think in Eisenhower's case, but certainly covert action becomes quite intrinsic to US Policy in this period under Eisenhower.

[David McCloskey]

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. So they are trying to avoid that at all costs. 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. 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, US 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.

[Gordon Carrera]

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

[David McCloskey]

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. Right. 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 most of our story. The, 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 US 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.

[Gordon Carrera]

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 US Coast. And I mean, you can see 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.

[David McCloskey]

Yeah, it's interesting. The CIA now, looking back at this period, I think 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, you know, 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. As late as November 59, so after the State Department has essentially said US policy is that we need to find a way to quietly push CASTOR out, the CIA deputy Director testifies to Congress that Castro himself is not a Communist. 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. Now, Dulles in this period is. 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 the new friend of the podcast will refer to him as Dickie. Dickie Bissell in these episodes. Dickie Bissell, now Bissell, is a 1950s CAA officer out of central casting. He is this kind of brilliant character. He's raised in a wealthy Connecticut family. Actually 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. 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. dickie Bissell graduates from Groton and where else? Yale. He, 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. So Dickie Bissell basically was the purse strings for the Marshall Plan. 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.

[Gordon Carrera]

In the area called Georgetown. Just in.

[David McCloskey]

Yeah, the Georgetown area. D.C. features people like Katherine 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, PhD who could win a bar fight. He, 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, of nervous energy. Dickie Bissell has wound up at the CIA because he befriended Alan Dulles. And then as well 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 Dickie Bissell was a W2 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.

[Gordon Carrera]

Yeah, to overthrow a government on behalf of a US corporation, United Fruit, 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.

[David McCloskey]

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 U2 spy plane. Gordon the Air Force had predicted that it would take six years to develop the U2. 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, 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. He falls 30ft 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 gonna be really important. Domineering, perhaps, but domineering, yes.

[Gordon Carrera]

Blind spots.

[David McCloskey]

And he's got real blind spots. 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. 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 Cuba file 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 11 of 1959, says 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. 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.

[Gordon Carrera]

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 questions of who really killed jfk.

[David McCloskey]

But of course, if you don't want to wait for that episode, you can join the declassified club, go to thereestisclassified.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 miniseries 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 [e-mail] we'll see you next time.

[Gordon Carrera]

See you next time.

[Alastair Campbell]

Alastair Campbell here from the Rest is Politics. Now, we've just released a series on one of the most controversial and consequential people of the past 50 years, Rupert Murdoch.

[James (Rest is Politics Co-host)]

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.

[Alastair Campbell]

Power without responsibility. The prerogative of the harlot throughout the ages. This is where he becomes not just a newspaper owner, he becomes a major newsmaker.

[James (Rest is Politics Co-host)]

Fuck Dacre publish. There is always a premium on bringing him gossip.

[David McCloskey]

I don't know what you mean by down market and upmarket, but that is so English class ridden snobbery.

[Commercial Announcer]

When you talk like that, how you.

[James (Rest is Politics Co-host)]

Get it doesn't make any difference. Actually, to be perfectly honest, whether it's true or not doesn't make much difference.

[Alastair Campbell]

There is a massive, massive scandal brewing. This was industrial illegal activity. And that I think is what really cuts through to the public thinks you people are really, really bad.

[Gordon Carrera]

I would just like to say $0.01. This, this is the most humble day of my life.

[James (Rest is Politics Co-host)]

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.

[Alastair Campbell]

To hear more, just search the rest is Politics. Wherever you get your podcasts.