91. JFK vs the CIA: Killing Castro (Ep 2)

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Speaker 6 From Dallas, Texas, the flash, apparently official, President Kennedy, died at 1 p.m. Central Standard Time.

Speaker 1 Cuba itself is really quickly going to become the Kennedy administration's top priority.

Speaker 8 The next four years are going to be difficult and challenging years for us all.

Speaker 9 At the end of the day, the U.S. is facing off against this tiny island, Cuba.

Speaker 1 How could you lose?

Speaker 10 Castro will tell the General Assembly the United States is seeking to overthrow him.

Speaker 1 Kennedy really looks to the CIA to get the business of the Cold War done. Castro and his fellow dictators, they rule nations, they do not rule people.

Speaker 9 The CIA were kind of playing JFK.

Speaker 1 In the eyes of some CIA-trained militants, Kennedy had become a traitor to the cause.

Speaker 10 B-26 bombers of the Cuban exile air force attacked Castro's airfield.

Speaker 1 Everything that could go wrong does.

Speaker 9 Out of ammunition, men fighting in water, if no help given, Blue Beach lost.

Speaker 10 The airstrike has humiliated the United States before the world.

Speaker 1 Were you ever offered money to assassinate assassinate President Kennedy? Directly,

Speaker 9 on numerous occasions.

Speaker 1 It is clear that the forces of communism are not to be underestimated in Cuba or anywhere else in the world.

Speaker 8 It's like a nightmare.

Speaker 1 It's

Speaker 8 something you think, well, I'll wake up tomorrow and it's not true.

Speaker 9 I think that Senator Kennedy's policies and recommendations for the handling of the Castro regime are probably the most dangerously irresponsible recommendations that he's made during the course of this campaign.

Speaker 9 I do know this, that if we were to follow that recommendation, that we would lose all of our friends in Latin America.

Speaker 9 We would probably be condemned in the United Nations, and we would not accomplish our objective. I know something else.
It would be an open invitation for Mr.

Speaker 9 Khrushchev to come in, to come into Latin America and to engage us in what would be a civil war and possibly even worse than that.

Speaker 9 Well, welcome to the Rest is Classified. I'm Gordon Carrera.

Speaker 1 And I'm David McClarski.

Speaker 9 And that was Richard Nixon in the last presidential debate of 1960 against the Democratic candidate, John F. Kennedy.
And we are, of course, charting. the story of John F.

Speaker 9 Kennedy in the CIA and of Cuba and Castro.

Speaker 9 And last last time, David, we set up the story really with an understanding of Castro coming to power in the island of Cuba, just off the coast of the United States, Washington increasingly fearing that he was a danger, perhaps some kind of communist as well as a nationalist, and feeling something needed to be done and turning to what else, the CIA, to try and take action against him.

Speaker 9 And David, this time, I guess we're going to explore how that story unfolds, what the CIA is going to get up to, one of its worst disasters, some might suggest.

Speaker 9 Because we're very interested, I think, in the relationship between the CIA and political leadership. You know, it's one of the themes of our podcast, but also particularly in this story.

Speaker 9 And as that opening quote suggested, Castro comes to power in 59. 60 is an election year.
You've got the Eisenhower administration first, but also the knowledge that a new president is coming.

Speaker 1 Well, that's exactly right, Gordon.

Speaker 1 And we, I guess, really left off with the CIA having been tasked with coming up with options to remove Castro by this new policy that the Eisenhower administration has taken on, which is to remove or destabilize Castro and to do it without really an overt U.S.

Speaker 1 hand. It's been passed to the CIA.

Speaker 1 We set up Alan Dulles as the director of the CIA, but the mastermind of this plan is going to be his deputy director for plans, his head sort of covert action guy named Dickie Bissell.

Speaker 1 Richard Bissell is his Christian name. And Bissell in 1960 is going to stand up a special task force at the CIA.
Always exciting when a task force gets stood up, Gordon.

Speaker 1 He's going to stand up a group to look at options for overthrowing Castro, and he's going to request conditional approval to take covert action against Fidel.

Speaker 1 Now, that request is approved very quickly by the Eisenhower administration.

Speaker 1 And there's an interesting kind of bureaucratic story here about how COVID action programs actually get approved and eventually implemented, because we get some insight into the workings of the Eisenhower kind of White House and the connection between the political leadership and the CIA at the time, which is that there was a small subcommittee of the National Security Council called the Special Group that included Eisenhower's National Security Advisor, the Assistant Secretaries of State and Defense, and what was then called the DCI, the director of central intelligence, was Alan Dulles.

Speaker 1 And the explicit task of this group was to authorize and monitor covert action.

Speaker 1 But the not so explicit purpose of this group was to provide a buffer of plausible denial between the President of the United States and covert action.

Speaker 1 So you'll note that Eisenhower himself does not sit on this special group.

Speaker 1 And there is a brilliant book written by a historian named Jim Rasenberger called The Brilliant Disaster, JFK Castro, and America's Doomed Invasion of Cuba's Bay of Pigs.

Speaker 1 And Rasenberger makes the phenomenal point that the special group essentially is deputized by Eisenhower to act as his proxy.

Speaker 1 He doesn't sit on it, so coups, assassinations, potentially messy covert action can be approved by this group. And Eisenhower's name isn't on the minutes.
He doesn't have to be there.

Speaker 1 It's a wink and nod kind of a thing where Eisenhower fully understands and is being briefed on what's going on.

Speaker 1 He has knowledge and consent of everything the CIA is doing, and yet he can remain at arm's length from the messy details of the process.

Speaker 9 Because I'm aware in some other cases, not actually the Cuba case, where he'll say things like, we need this person removed or eliminated.

Speaker 9 And everyone will go away from that meeting knowing that he's actually ordering an assassination. Congo and Lumumba is, you know, just one famous example.

Speaker 9 But he never quite says it and his name is never on it. And that seems to be the way in which the relationship between the CIA and the White House works at this point.

Speaker 9 And so the order has been given for some pretty aggressive action, which is going to be led by the CIA, to basically get rid of Castro.

Speaker 9 They're set on that course, but it's how they do it, which is the issue.

Speaker 1 And the CIA,

Speaker 1 and really under Dickie Bissell, spent the winter of 1960 kind of throwing out a bunch of different ideas for destabilizing Castro's regime. And some of these are quite ludicrous, seeming.

Speaker 1 Many of them are not. Many of them are straightforward.
So, you know, things like sabotage, you wreck sugar refineries, economic warfare, political propaganda, the kind of usual fare.

Speaker 1 But some of them are a little bit nuts. So one idea was to use a drug, which if placed in Castro's food would make him behave irrationally in public.

Speaker 1 And here one thinks, given the overlap with the MK Ultra program at the time, which we have covered in past episodes on this podcast, where

Speaker 1 it's the CIA and the head of the technical services division, a man named Sid Gottlieb, also a friend of the pod, was experimenting with LSD.

Speaker 1 One wonders if the substance being referred to there was actually placing some LSD in Castro's food or drink.

Speaker 1 There was another idea, which was to sprinkle a depilatory powder into Castro's shoes that would cause his hair. beard and all to fall out.

Speaker 9 More like a kind of schoolboy prank. I know it's supposed to undermine it because we said last time his beard is one of his iconic features, but it is still.

Speaker 9 If I was Eisenhower and I'd wanted him removed,

Speaker 9 I think you'd be like, well, we got his beard to fall out, says the CIA chief.

Speaker 1 I'd be like, oh, great, thanks. Well, so one of the contributors to this pool of crazy ideas was none other than Ian Fleming himself.
I was shocked to learn this, Gordon, in researching this episode.

Speaker 9 Author of the James Bond novels.

Speaker 1 Author of the James Bond novels. Now, Alan Dulles was a huge Bond fan.
The kind of rumor was that if he

Speaker 1 read a Bond novel and he knew that CI didn't have the gadgetry, he might actually go ask how long it might take to produce something similar.

Speaker 1 And Fleming apparently attends a dinner party in Georgetown, this kind of ritzy neighborhood in D.C.

Speaker 1 And after dinner, the guests are having coffee when who else but then Senator John F. Kennedy turns to Fleming.
and asks him what he would do to get rid of Castro.

Speaker 1 And Fleming suggests dropping leaflets over Havana warning residents that atomic tests had poisoned the Cuban air with radiation.

Speaker 1 And since radiation lingered on beards, so the thinking goes, since Cuban men prize their virility above all else, this is Ian Fleming, that even Castro would have to shave his beard and thus be shorn of some of his revolutionary mystique.

Speaker 1 So there was a CIA officer who was present who told Dulles about Fleming's comments. Dulles was apparently quite intrigued, but

Speaker 1 I don't think that ever made it.

Speaker 9 It's not quite a license to kill. I think it's not quite sending Bond out to get him, is it?

Speaker 1 We mentioned at the end of the last episode that one of the first ideas that emerges from Dickie Bissell himself is:

Speaker 1 let's kill Castro. You know, eliminate was the word he used.
And the CIA does consider the merits of a triple assassination of Fidel, his brother Raoul, and Che Guevara.

Speaker 1 And on the morning of the 17th of March, 1960, the CIA brings a plan titled A Program of Covert Action Against the Castro Regime down to the White House. And this is the big meeting.

Speaker 1 Eisenhower actually is there for this. He's got more than a dozen top officials.
And this is the approval meeting essentially for the CIA's big plan on its covert action program in Cuba.

Speaker 1 And the program is going to call for the, basically, the creation of four distinct assets that will lead to what they describe as the replacement of the Castro regime with one more devoted to the interests of the Cuban people and more acceptable to the US in such a manner as to avoid any appearance of U.S.

Speaker 1 intervention. So, again, that covert action sweet spot.
So, four things they're after. One, a political opposition group that they define as responsible, appealing, and unified.

Speaker 1 Two, intensive anti-Castro propaganda to be broadcast into Cuba. Three, a covert force of anti-Castro Cubans that would gather intelligence and carry out clandestine missions inside Cuba.

Speaker 1 And then four,

Speaker 1 an adequate paramilitary force that could be trained outside of Cuba and later deployed against Castro. So again, nothing formally in the plan on assassination.

Speaker 1 There's no mention of a large-scale invasion.

Speaker 1 The CIA estimates that it'll take six to eight months to put that into action and require $4.4 million, which in today's dollars is equivalent to about $44 million.

Speaker 1 Eisenhower approves the plan immediately, but stresses his, really his only condition is that it absolutely must remain secret. Oops.
Didn't really

Speaker 1 stay there. With it, though, after this meeting, the overthrow of Castro really becomes a secret goal of U.S.
foreign policy. And again,

Speaker 1 it's going to fall to Dickie Bissell to make all this happen. So he stands up a new organization inside the CIA.
It is Branch 4 of the Western Hemisphere Division, known as WH4.

Speaker 1 And it starts with about 40 people at this time: 18 in Washington, 22 working covertly from Cuba, but it is going to grow massively.

Speaker 9 What's interesting, though, is that a lot of the people who are pulled into this are veterans of the Guatemala overthrow earlier in the 50s. So

Speaker 9 you get this sense that they feel like, well, we did Iran in 53, we did Guatemala in 54, now it's going to be Cuba in 60. We know how to do these kind of coups and covert action.

Speaker 9 But actually, also some of the people in there are not necessarily, if you read some of the accounts, the best people or the smartest people in the CIA. Shock horror, not everyone, is brilliant.

Speaker 9 I mean, it is quite interesting. And one of them, I mean, fascinating, isn't it? One of them is E.

Speaker 9 Howard Hunt, who becomes very famous later on because he's one of the people involved in the Watergate burglary under Nixon.

Speaker 9 And this is going to be part of the kind of grand conspiracy theories, I think, around Castro Kennedy and assassinations at Watergate.

Speaker 9 But yeah, it's a kind of weird mix of a group, and it doesn't come across necessarily as the A team, I think, from the CIA.

Speaker 1 I was heartened in a sick way to see that the same bureaucratic squabbling around task forces that I experienced while I was at the CIA was alive and well in the 1950s and 1960s, because

Speaker 1 this is exactly what I experienced when we had the Arab Awakening in like late 2010 and early 2011. There was a Middle East task force that got stood up to respond to this.

Speaker 1 And of course, it sounds great if you're the director of the Central Intelligence Agency or the director of intelligence, the deputy director for intelligence is kind of the chief analyst, to say, look, there's a task force that has been stood up.

Speaker 1 But the reality of how these task forces get staffed is

Speaker 1 not the way that a politician would want it to be staffed. Because what happens is every component that already exists.

Speaker 1 is told, okay, you've got to send 10 people based on your size and you've got to send five.

Speaker 9 And you've got to send a- And do you send your best 10 people?

Speaker 1 You do not, Gordon. You do not send the best people.
It ends up being the sort of Star Wars cantina of

Speaker 1 analysts who wind up being there. It's like people who, for whatever reason, want to work a night shift or somebody who doesn't get along with their manager, right?

Speaker 1 And who gets sent over there because the manager's like, now I know. I've got a spot I can get rid of Susie or whoever it is who I don't like.

Speaker 1 Like you send them over there to the Middle East Task Force. It does seem like what happened here is similar, that you had a lot of people that were kind of lower performers.

Speaker 1 Interestingly, a lot of the senior-ish people have a track record as performers. So one of them had been a script writer.
One was a trained opera singer. One was a trained actor.

Speaker 1 Another one was descended from a line of East European circus clowns.

Speaker 9 Send in the clouds.

Speaker 1 Yeah, exactly. So you have an interesting brew people running the Cuba show.
I do think it's worth a brief minute on Guatemala because so many Guatemala veterans come in.

Speaker 1 And I think that experience really shapes how they think Castro can be overthrown. Because they really, they think of the Guatemala scenario as kind of the template.

Speaker 1 And what happened in Guatemala in 54 is that the agency had run a campaign of political agitation and propaganda under the cryptonym PB Success, which had deposed this kind of alleged Marxist dictator and installed a more friendly client.

Speaker 1 But it was very heavy on the political side of things.

Speaker 1 And what seems pretty clear in looking back at Guatemala and then trying to compare it to Castro's Cuba of 1959 to 1960 is that the two scenarios are actually not very similar.

Speaker 1 I mean, the deposed Guatemalan leader had enjoyed very little popular support, whereas Castro really enjoys a lot of it and has really worked hard in his first year in power to consolidate his regime.

Speaker 1 And also, the CIA had kind of looked at the Guatemala operation in the years after, and there had been a memo written internally about why it had worked.

Speaker 1 And the memo underscored the, quote, unique coincidence of favorable factors and unbelievable luck that had contributed to the Guatemala operation.

Speaker 1 So comparing these two scenarios is probably not so wise analytically, but you've got a kind of top tier in this new task force who come in and think of Cuba, I think to some degree, as another version of Guatemala.

Speaker 9 So they're going to try and kind of mirror that with kind of a mixture of propaganda, kind of creating front organizations, a body called the Cuban Revolutionary Front, Frente, Revolucionaro Democrático.

Speaker 9 How is that?

Speaker 1 Nailed the friend.

Speaker 9 Not bad.

Speaker 1 Yeah, and we should say again, we said this in the Pablo series. We take no responsibility for

Speaker 1 just terrible pronunciation. We mean no disrespect.

Speaker 9 But this is the model they're going to use, which is propaganda, political fronts to try and shape an opposition movement plus kind of covert action and paramilitary work.

Speaker 1 Yeah, they set up a radio station that's going to broadcast into Cuba from... place called Swan Island.
The CIA throws money at anti-caster newspapers and runs leaflet campaigns.

Speaker 1 A new CIA station is set up in Miami to try to organize this kind of fractious opposition. And the paramilitary side kicks into gear as well.

Speaker 1 And this is going to be probably the most important kind of thread in the story to come because the CIA wants to go and recruit Cubans who maybe have served in, you know, they served in Batista's army or were part of these kind of student organizations, so familiar with some kind of discipline.

Speaker 1 They're going to go and recruit people who can actually form into small paramilitary units that can then be covertly inserted into Cuba.

Speaker 1 And the recruits that the CIA finds, as I said, you know, former soldiers, students, many are Catholic. There are some doctors, lawyers, even CPAs.

Speaker 1 Most of them have some kind of personal vendetta against Castro. You know, they saw friends or family killed during the revolution.
And the CIA begins with about 500 potential candidates.

Speaker 1 They take those candidates to an island island off of Florida's Gulf Coast where the CIA has taken over a golf course, and the recruits live there for a month.

Speaker 1 They take polygraphs, they take psychological exams, they take IQ tests, and they begin to receive basic military training, you know, guerrilla warfare, demolition, small arms.

Speaker 1 They're supplied with weapons. And, I mean, the CIA is running this, but the CIA is working hand in glove with a lot of other parts of the U.S.

Speaker 1 government, the State Department, Treasury, the Attorney General.

Speaker 9 You're trying to spread the blame, David.

Speaker 1 No,

Speaker 1 it's just to say that from the beginning, there was some measure of cooperation necessary with other parts of the U.S. government.

Speaker 1 And of course, the big one here is going to be the Pentagon, the Department of Defense, where the Army is lending military camps and personnel. The Air Force is donating aircraft.

Speaker 1 The Marines are providing staffing.

Speaker 1 The National Guard even, the Alabama National Guard is going to end up supplying pilots to help with the training.

Speaker 1 The Navy will provide the fleet that's going to escort this exile army eventually back to Cuba. So it's the CIA's plan, but it's a big operation.

Speaker 9 Which once you include all those agencies and you include the fact that you've got exiles in Miami, you can already see that Eisenhower's kind of instruction to keep it secret is going to be pretty hard.

Speaker 9 But this is all coming together through 1960. And I guess at the same time, tensions are rising.
It's becoming clearer that Castro... is veering more towards communism, towards the Soviet Union.

Speaker 9 There's some kind of trade trade beginning, Cuban sugar being sold to the Soviet Union, some kind of other agreements, even some small arms going.

Speaker 9 So you can sense tension rising, the determination growing to do something about it. And in the background, you've also got a U.S.
election campaign kicking into gear.

Speaker 1 In addition to all of the sort of jockeying at the political and economic level, The Eisenhower administration has squeezed baseball's International League, one of the sort of top minor leagues for Major League Baseball in the States, to announce that it was pulling its baseball team, the Sugar Kings, out of Havana.

Speaker 1 And Castro's livid because he had been known to suspend cabinet meetings so he could go watch the Sugar Kings play. And he goes nuts.

Speaker 1 The Sugar Kings, of course, are another casualty of this whole thing. They become the Jersey City Jerseys and then go bankrupt the next year after they're pulled out of Havana.

Speaker 1 Castro is a big baseball fanatic. This is an absolute gut punch.
So these, this year

Speaker 1 of 19th.

Speaker 9 Is this back to the idea that the World Series is basically just American teams playing each other?

Speaker 1 Is that I mean that's not an idea. That is what is the reality.

Speaker 1 I guess

Speaker 9 the Cuban teams got kicked out. Is that what you're telling me?

Speaker 1 The point here, 19, the point, Gordon, is that Cuba in 1960, as these tensions rise between Washington and Havana, it becomes, number one, Castro is consolidating power.

Speaker 1 And number two, Cuba becomes braided into U.S. domestic politics because we're in an election year.

Speaker 1 And unsurprisingly, compared to Fidel's fun trip to New York the year before where everyone's wearing their novelty Fidel beards and he's playing peekaboo, American views of Castro have absolutely tanked.

Speaker 1 So by the summer of 1960, 81% of Americans have an unfavorable view of Fidel Castro.

Speaker 9 And so let's set up the election because this is very important to the story.

Speaker 9 On the Republican side, you've got Richard Nixon, who has been vice president under Eisenhower, so quite locked into the Eisenhower policy, quite fiercely anti-communist, obviously knows quite a lot about what's going on.

Speaker 9 And then on the Democratic side, we have the young, charismatic senator from Massachusetts, John F. Kennedy.

Speaker 1 Well, and we could spend a whole series on Kennedy Gordon, but this is not the rest is history. I think they've done that right.

Speaker 1 And they've already done it. They've already done it.

Speaker 1 So I think three aspects of Kennedy's background and personality are really important for kind of framing this rest is classified journey into Kennedy, Cuba, and the CIA.

Speaker 1 And here, I think a tip of the cap to a biography of JFK called An Unfinished Life by Robert Dalek, which really does a phenomenal job of setting up the man. So

Speaker 1 the first thing is for JFK,

Speaker 1 Family is a separate institution unto itself. So he's born in 1917 into a very elite Boston family that is kind of a fusion of a banking fortune.

Speaker 1 His mom's the daughter of a legendary Boston politician, congressman, and mayor.

Speaker 1 And Kennedy's dad, Joe Kennedy Sr., really, I think, beats into the boys early on that they need to be loyal to each other above all. Now, Kennedy has an older brother, Joe Jr.

Speaker 1 And then he's got his younger brother, Robert F. Kennedy, RFK, the original RFK, not the Maha guy, okay, the guy who's around now.
Secretary's dad.

Speaker 1 JFK's relationship in particular

Speaker 1 with

Speaker 1 Robert Bobby is going to really feature in the CIA and Cuba story because

Speaker 1 they are

Speaker 1 going to look at

Speaker 1 the way that things unravel with Castro and the CIA, I think, through the lens of protecting the family to some degree. So family is an institution unto itself.
That's point one.

Speaker 1 Point two is that Kennedy has been groomed for public service throughout his whole life and has an intense interest in foreign affairs. So JFK, he goes to Harvard, he gets B's and C's.

Speaker 1 He's kind of a disengaged student. Lots of what Robert Dalek describes as catting about, which is a nice way of saying that rich young men in the 1930s who slept around a lot.

Speaker 1 He puts most of his energy into sports and social activities and girls. He's a very big traveler.

Speaker 1 His father sends him on summer tours of Europe, but he does have this real interest in what's going on in the world.

Speaker 1 I mean, he wrote his thesis at Harvard, which is very bizarrely later published as a book titled Why England Slept.

Speaker 1 And there's been lots of analysis of this work, which in many respects is a kind of typical undergrad thesis, but I think it does show JFK's belief.

Speaker 1 in kind of the importance, at least in theory, of unsentimental realism in foreign affairs. The book receives glowing reviews.
It sells well in the US and Britain.

Speaker 1 Of course, during the Second World War, JFK is a commissioned officer in the Navy.

Speaker 1 He commands a PT, a patrol torpedo boat in the Pacific, and becomes a bit of a war hero as the boat is sunk while they're attacking a Japanese convoy.

Speaker 1 Through JFK's leadership, all but two members of the crew are rescued.

Speaker 1 So he comes back, you know, this sort of notable man from a notable family with a great track record in the Second World War, and he runs for a seat in Congress, representing part part of Boston.

Speaker 1 And here we really see he kind of turns this aristocratic charm that he has into a retail political persona, right? He wins the general election handily. He enters Congress in January of 1947.

Speaker 1 But the whole point for JFK is like his brother, by the way, we should say, had died in the Second World War. And so JFK is now the kind of heir apparent to his dad.

Speaker 1 And so each of these progressions from the war into Congress, he's then going to run in 1952 for the Senate. He narrowly wins.
He's re-elected quite handily in 1958.

Speaker 1 All of this is just a stepping stone for the place that JFK knew that he and his dad wanted him to be all along, which is to run for president and to become the president of the United States.

Speaker 1 So two, that grooming for public service. And then three, this one really important is Kennedy.

Speaker 1 He is interesting, I think, Gordon, because there's a lot of idealistic talk and tone in the way he talks about the world, but he's kind of a hawk on defense, right?

Speaker 1 And he is, he's committed to this kind of rollback of communism and Soviet influence, even as he espouses those kind of liberal ideals.

Speaker 9 I find it kind of interesting to frame him in terms of a hawk or a dove, because he is obviously hawkish on communism and big on foreign affairs.

Speaker 9 And there are strains of his thinking which are more idealistic and internationalist. And there are strains which are quite hard-headed and, if you like, kind of realist.

Speaker 9 And I think he's kind of an interesting fusion of those two elements. And you see different people slightly projecting different elements onto him.

Speaker 9 And that will actually become part of the story of the assassination that we'll come to is people who wanted to see him as a kind of more liberal internationalist will kind of see a plot to stop that worldview becoming the dominant one in Washington and pursuing its interests.

Speaker 9 So I think it's worth saying he can be quite hawkish, but it's certainly complicated. And I think that actually is part of the story of Cuba and the campaign, isn't it?

Speaker 9 The kind of tension I think he feels between the different values of a kind of liberal internationalism and a kind of hawkish anti-communism.

Speaker 9 And I think they're going to come into tension with what to do about Cuba and Castro.

Speaker 1 You're right, Gordon, that he is a fusion of maybe some contradictory impulses to some degree.

Speaker 1 But what does seem pretty clear is that if he has a political opportunity to beat down Richard Nixon in the campaign in in 1960, he's going to take it and he's going to rail on the Eisenhower administration.

Speaker 1 I mean, famously, you know, Kennedy runs for president in 1960 in part on this idea that the Eisenhower administration has sort of allowed the U.S.

Speaker 1 to fall behind the Soviets in the fielding of intercontinental ballistic

Speaker 1 gaps, the missile gap, which is actually, turns out it wasn't true.

Speaker 1 The pigeon gap, but yeah. Right, the pigeon gap.
But Kennedy is going to take his political shots when he can.

Speaker 1 And the big one, the big one is going to be that, well, Eisenhower and then by virtue Nixon have lost Cuba. They've lost Cuba to Castro.
They've lost Cuba to communism.

Speaker 1 So Cuba is going to be a cudgel, I think, for JFK to beat Richard Nixon with throughout the campaign.

Speaker 9 That's right. And I think Cuba is going to be at the heart of the campaign.
And then that is going to define JFK's early days as president and then his whole presidency.

Speaker 9 So there, as we enter this kind of very heated and very close 1960 presidential election, let's take a break.

Speaker 9 And as we come back, we'll see how the campaign plays into the lead-up of what becomes the Bay of Pigs disaster for the CIA.

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Speaker 9 Welcome back. We're in 1960 and the presidential election campaign between Richard Nixon on the Republican side, JFK, John F.

Speaker 9 Kennedy on the Democratic side and Cuba and who's soft on Cuba or not and who's lost Cuba or who hasn't is a really central part of that campaign.

Speaker 9 It's going to kind of lock Kennedy into a particular position, isn't it?

Speaker 1 Yeah, Kennedy is going to recognize that he has a potential advantage over Nixon here because on Nixon's watch, so the thinking would go, Cuba became communist.

Speaker 1 And Kennedy is relentless on the campaign trail. I mean, in Florida, he'll say, you know, it's been lost to the communists.
Cuba's lost.

Speaker 1 He'll say things like, you know, in Cuba, the communists have gained a satellite.

Speaker 1 And he actually becomes very fond of a phrase throughout the entire campaign saying that Cuba is, quote, eight jet minutes away, right?

Speaker 1 So it's not just 90 miles off the coast of Florida, Gordon, it is eight jet minutes away from the United States. And he really brings up Castro like at every stop on the campaign trail.

Speaker 1 And he likes to say that those who say they will stand up to Mr. Khrushchev have demonstrated no ability to stand up to Mr.
Castro. You know, obviously a not-so-veiled reference to Richard Nixon.

Speaker 1 And in October of 1960, we're getting very close to the election in November, then candidate JFK issues a statement calling for greater U.S.

Speaker 1 intervention in Cuba, including aid to rebel forces, and he ridicules the Eisenhower administration's trade embargo as too little, too late. So JFK kind of wades into this debate.

Speaker 1 Now, we should say ongoing, unbeknownst, maybe to JFK, is a planning process by the CIA to develop this covert action program. And JFK is kind of calling for that publicly.

Speaker 9 Yes. Now, here's one of the really interesting questions: which is, is he doing this partly because he has been briefed by Dulles about the covert action program?

Speaker 9 Because that is the suggestion in some of the books I've read, not just some of the more conspiratorial books I've read, David, but some of the more serious books.

Speaker 9 And Nixon is going to actually think that because

Speaker 9 what the suggestion is, is that Dulles kind of tips off JFK, that planning is in motion to remove Castro.

Speaker 9 And JFK is kind of worried. Well, what if this happens before the election? Nixon's going to look strong because he's the vice president.
You know, I'm going to look weak.

Speaker 9 My best bet is to get ahead of that and to be... as aggressively anti-Castro as I possibly can be.

Speaker 9 So if this coup does happen, I'll have looked like I called for it and Nixon won't get the credit for it.

Speaker 9 And Nixon is certainly going to believe that Alan Dulles has briefed Kennedy on the policy during the summer. It'll be one of kind of Nixon's grievances.

Speaker 9 I mean, Nixon's got plenty of grievances with everybody.

Speaker 1 Add it to the list.

Speaker 9 And of course, Nixon can't say anything. He's vice president.
He knows there's a covert action going on, but of course, it's a secret covert action. That's what Eisenhower wants.

Speaker 9 So he can't go out there and say, oh, but we are doing something. We're planning something because that would blow it.

Speaker 9 So he's in a slight bind in terms of not being able to kind of say very much, whereas JFK can sound like the aggressive one. So

Speaker 9 I find that quite interesting because it's also, it's kind of boxing Kennedy in to a tough, hard line policy on Castro and Cuba for political advantage, which is also going to lead him perhaps into problems later.

Speaker 9 And that does seem to me to be quite plausible, whether you see Dulles, you know, head of the CIA, having done it as some kind of master conspiracy, or whether it's just what Dulles did, you know, in terms of briefing a candidate.

Speaker 9 But does seem to have been something that may have happened there.

Speaker 1 Dulles, of course, strenuously denies that he briefed JFK in July. So I think they went down to Dulles and Bissell, I believe, went down to Palm Beach to brief candidate Kennedy in July.
And

Speaker 1 I will ask, though, Gordon, did you encounter in

Speaker 1 your various sources any actual evidence that that briefing had drifted into the covert action plan?

Speaker 1 Or is it the circumstantial evidence that around this time, or really in the fall after Kennedy begins to kind of essentially call for a COVID action program ostensibly without knowing that one is actually in development?

Speaker 9 So my reading of it is that it doesn't have to be as explicit as Dulles briefing him on the COVID action plan, but you could understand how a nod and a wink could take place that something is underway, which Kennedy then understands what's being suggested and decides, well, I'm going to kind of outflank that, as it were.

Speaker 9 So I find that eminently plausible.

Speaker 1 We should say, I mean, Dulles and JFK are friendly socially.

Speaker 9 Yeah, they're in the Georgetown set to some extent at this point. They move in the same circles, and it's one of kind of Nixon's resentments.

Speaker 9 But at this point, yeah, Dulles and JFK seem like they move in similar worlds of those kind of Georgetown dinner parties in a way that Nixon always felt, you know, the outsider.

Speaker 1 Well, in any case, where we end up is Nixon, essentially, I mean, as the quote you read to start the episode, says that JFK's ideas are irresponsible and could

Speaker 1 lead to the U.S. getting involved in a Cuban civil war.

Speaker 1 Actually, this is an example of Nixon really doing something quite responsible, which is protecting the security of the ongoing covert action program, whereas Kennedy can kind of lob missiles at him from the sidelines.

Speaker 1 So in any case, we have this weird instance where Nixon could kind of be portrayed as being soft on Castro. What's not soft on Castro, though, is that by the summer of 1960,

Speaker 1 this idea of maybe killing or eliminating Fidel, which had been, again, raised by Dickie Bissell back in December of 1959, this idea comes back.

Speaker 1 And we should say, Gordon, that in 1960, the CIA is definitely in the assassination business. Peak assassination business.
This is peak assassination business.

Speaker 1 I mean, there's been the attempt against Lumumba in Congo, against Trujillo in the Dominican Republic, and now Castro. So we look back on this and think, oh, wow, this is insane.

Speaker 1 In 1960, inside the Eisenhower administration, this didn't seem insane at all. Now, they don't put anything to paper that could explicitly link the CIA or the White House to an assassination.

Speaker 1 Bissell calls them bad words, like assassination is a bad word. You don't say bad words.
It's kind of unfit for public discourse. A lot of winking and nodding in this period.

Speaker 1 And I do think Bissell's mindset on this is important because

Speaker 1 we

Speaker 1 sitting here in 2025 sort of have a knee-jerk reaction to the idea of assassinating a foreign leader.

Speaker 1 I think for Bissell, though, he's again looking at this through the context of the Second World War. So he's looking at this in the context of the fire bombing of Dresden, bombing Hiroshima.

Speaker 1 If you could avoid a disastrous conflict that's going to claim untold numbers of lives, by killing one person, doesn't that justify it?

Speaker 1 Remember the episodes we did on on Mohsen Fakrizadeh and the kind of Mossad thinking on assassinating the head of Iran's nuclear program?

Speaker 1 You can get to a point where you think, I'm killing to save lives. And I think that's exactly what Dickie Bissell thought he was doing here.

Speaker 9 Yeah. I think we can question whether that's effective or not.
I mean, that's a kind of different debate, but that's certainly where we...

Speaker 9 are at this point where it looks like Eisenhower basically without explicitly saying it has given the go-ahead for the CIA to look at how to do it. And how are they going to do it though, David?

Speaker 9 That's the question.

Speaker 1 Well, Eisenhower Gordon kind of gets a little explicit because at one point he tells, I think this is in the beginning of the summer 1960, he says he wants Castro, quote, sawed off.

Speaker 1 So, you know, it's a relatively clear directive on what sawed off sounds like the kind of euphemism the mob might use.

Speaker 1 It does.

Speaker 9 It does, doesn't it? Speaking of which, back to our friends.

Speaker 1 Back to our friends. So

Speaker 1 what happens is Bissell,

Speaker 1 Dickie Bissell, working with this this directive, essentially, from the president to come up with a way to kill Castro, approaches the head of the CIA's Office of Security.

Speaker 1 There's been some back and forth on who approached who. I don't think it really matters.
The point is, is that the idea is to use the mob to kill Castro.

Speaker 1 Let's go and subcontract this out to the mafia.

Speaker 9 I mean, that's kind of nuts. I mean, A.
You'd think to yourself, it's not very secure. It's not very reliable.

Speaker 9 I mean, you kind of think, if you're the CIA, shouldn't you be able to do this yourself rather than having to subcontract out to the mob?

Speaker 1 But you don't want to do it yourself.

Speaker 1 You don't want anyone involved who could be connected back to the CIA.

Speaker 9 You're suggesting it was a brilliant plan.

Speaker 1 You are right on the operational security point that, as we'll see, a lot of people involved in this will eventually talk about it in real time to the point where the FBI learns about the plotting from listing in on gangsters.

Speaker 1 But I actually,

Speaker 1 I think this is a brilliant idea, Gordon.

Speaker 1 Does that surprise you? Yeah.

Speaker 1 I think the more I got into this, the more I thought,

Speaker 1 why not give it a try? I mean, we talked in the first episode about

Speaker 1 how much money the mob had lost. I mean, hundreds and hundreds of millions of dollars had been lost when Castro took power.
And the mob's got grievance. The mob has

Speaker 1 tons of connections with all kinds of unseemly people in Havana. So the mob's got the ability to do it.
The mob's got the motive to do it.

Speaker 1 Why not give it a shot? Again, if you're looking at this from the standpoint of

Speaker 1 this whole Cuban situation could be resolved if we just killed Castro.

Speaker 9 Yeah, the nice, easy idea, it's thought.

Speaker 1 This program, though, we should note, like... The covert action planning that we've been describing is all rigorously logged and documented.

Speaker 9 That's the kind of paramilitary propaganda, political, though. Yeah.
And then the mob bit is,

Speaker 9 I love the fact the mob bit is being run by the CIA's Office of Security. That's the kind of bit of the CIA which is given the job of liaising with the mob.

Speaker 1 Because it's kind of based, it's based on like personal connections. Okay.
You know, it wasn't a bureaucratic decision.

Speaker 1 It was that the head of the Office of Security at the time knew and had worked with, and actually, I think, subcontracted some jobs to a middleman named Robert Mayhew.

Speaker 1 And Mayhew is the kind of guy who in the 1950s and 60s has kind of done some odd and relatively sleazy work for the CIA.

Speaker 1 So, for example, he had helped arrange for a B-movie actress to go to bed with then 23-year-old King Hussein of Jordan when he visited the U.S.

Speaker 1 So he was like procuring entertainment for visiting foreign dignitaries on the part of the CIA because the CIA didn't want to, you know, don't want to get involved with that.

Speaker 1 Maybe you don't want to have to put that on paper. So So you've got this contract with Mayhew, who's doing all kinds of kind of odd jobs.

Speaker 1 Now, Mayhew, of course, like, he's a former Phoebe Gordon, which I love. So he's kind of.
Former FBI agent. Yeah, he's a former FBI agent.

Speaker 1 And he is living in Las Vegas where he's working as a fixer for Howard Hughes, kind of watching over his assets and interests.

Speaker 9 He's a massive billionaire. Yeah, famous.

Speaker 1 Yes. Now, Mayhew is on a CIA retainer of $500 per month.
So he's tapped by the Office of Security to look into how this could be done. And Mayhew has some contacts with the mafia.

Speaker 1 And in late summer of 1960, he meets with a mobster named Johnny Roselli in Beverly Hills. Now, Mayhew and Roselli are...
longtime friends and kind of social acquaintances.

Speaker 1 Roselli has actually come to Thanksgiving dinner at Mayhew's home in Virginia. So they're they're buds.
Now, Johnny Roselli, set him up a bit here. He's got movie star good looks.
He's got thick hair.

Speaker 1 He wears diamond cufflinks. He's known as handsome Johnny.
Johnny Roselli, by the way, is actually not his real name. He's Filippo Sacco.

Speaker 1 He's actually an illegal immigrant from Italy without proper papers, but he's actually forged a birth certificate for himself.

Speaker 1 He runs the Los Angeles and Las Vegas business for the Chicago mob, known as the Outfit.

Speaker 1 He had originally worked for Al Capone, and now he works for a boss named Sam Giancana, who will also be an important mobster in this story.

Speaker 9 So he's straight out of the goldfather, basically.

Speaker 1 Yes, yeah,

Speaker 1 central casting.

Speaker 1 Now, Giancana and Rosselli together had run a resort in Cuba before Castro's revolution, and so had seen essentially a massive loss in profits and cash flow when Fidel Castro takes power.

Speaker 1 So they've got a beef with Fidel. Now, Rosselli and Giancana probably also think that

Speaker 1 doing the CIA a solid might help them down the line if they were to face any uncomfortable prosecution from the FBI or the Justice Department.

Speaker 1 So they probably think there's something to be gained here. And Rosselli, though, Gordon, he's not just a mobster.
He's also a movie producer. And he had actually helped, of course he is, right?

Speaker 1 He's good friends with Frank Sinatra and he had helped Frank Sinatra land his role in From Here to Eternity, a role for which Sinatra won an Academy Award.

Speaker 1 Also on handsome Johnny Rosselli's list of accomplishments are that he apparently controls the sort of ice-making machine business on the Las Vegas Strip, which I can imagine was quite lucrative in the 1950s.

Speaker 1 The FBI thinks he's guilty of maybe 13 murders, but he's a patriot, Gordon.

Speaker 1 He's an American patriot.

Speaker 1 And Mayhew shows up and essentially tries to sell Rosselli on a cover story, saying that he's working for a group of international businessmen who had raised $150,000 to take down Castro.

Speaker 1 And Rosselli, he understands that Mayhew has worked for the CIA in the past and probably sees right through this right away, but it's kind of okay for Mayhew to continue using that alibi. Now,

Speaker 1 Rosselli turns down the money. It says he'll do it for free.

Speaker 1 And here, you know, we should note, he probably actually is a patriot, but also if they kill kill Castro and get back in business in Havana, he stands to make tremendous sums of money from reopening his resorts in Havana.

Speaker 1 So this is not really a charitable kind of a thing. Rosselli, of course, wants some assurances that he's actually working for the government.

Speaker 1 And so he pushes Mayhew to actually have a meeting, a sit-down with members of the sort of quote-unquote international business conglomerate that are supporting this effort to off Castro.

Speaker 1 That happens in New York later that summer. The CIA officer who goes to that meeting continues with the original ruse, right?

Speaker 1 They're using this cover story that he's representing this group of industrialists. And Rosselli is fine with that because he actually recognizes the CIA guy.

Speaker 1 They had both attended a clam bake at Mayhew's house in Virginia a few years before. And so he knew him through that.
And so he understands this is good enough for Rosselli.

Speaker 1 He knows he's working for the Central Intelligence Agency. Now, Roselli has to get the approval from Sam Giancana, who is the head of the Chicago outfit.

Speaker 1 And Giancana might be responsible himself for over 100 murders. By the way, Gordon, when you asked me earlier if this idea is crazy, This is why this idea is not crazy.

Speaker 1 These guys are really good at killing people and getting away with it, right? So these are the guys you go to to get this thing done. They know Havana.

Speaker 1 They're good at killing people and they've got motive. In his book, Mafia Spies, the writer Thomas Meyer claims that Giancana's enterprise, the Chicago outfit, was worth north of a billion dollars.

Speaker 1 So it would make it about as lucrative as some massive actual conglomerates like General Motors or U.S. Steel.
But anyhow, Giancana agrees, right, in September of 1960.

Speaker 1 And there's a meeting in where else, Gordon, but the Boom Boom Room, the nightclub at the Fontainebleau in Miami,

Speaker 1 where Giancana, Mayhew, Roselli, another CIA guy, and a man named Santo Traficante, a mobster from Florida who had been deeply involved in the Cuban operations before Castro, are all meeting to talk about this plan.

Speaker 1 Now, everyone is using aliases at this meeting, except for Mayhew. And Mayhew, apparently, while they're meeting in the Boom Boom Room, does not recognize Giancana, but...

Speaker 1 A couple days later, he's reading an article in Parade magazine and sees a picture of Giancana and realizes that he's he's just met with the head of the Chicago mob.

Speaker 1 And here, Gordon, with this many mobsters introduced, I think we would be remiss in saying that we are running a very exclusive mini-series for our declassified club members where we are going to draw on these threads around the Cubans, the mob, and the CIA to look at some of the different theories around the Kennedy assassination.

Speaker 1 And the mob one, we are going to be joined by Anthony Scaramucci, the mooch, to talk about the intel that he has on the mob's potential culpability in killing Kennedy.

Speaker 9 It's his favorite theory, unlike it thinking it's the CIA, which is my preferred theory for the moment. My working theory.

Speaker 1 I can't believe it, Gordon. But that's your working theory.

Speaker 9 Maybe winding you up. But anyway, back to the story.

Speaker 1 So back to the boom boom room. Everyone in the boom boom room at this little table is talking about how they could kill Castro.

Speaker 1 And the CIA apparently thinks, okay, well, why don't you just do this like a mob hit? Like just gun him down in broad daylight. And the mobsters say, that's a suicide mission.

Speaker 1 It's going to be way too difficult to recruit for that. We should use poison.

Speaker 1 And Giancana proposes that the CIA fabricate a poison pill and suggests that they can essentially use underworld contacts in Havana to deliver the poison pills to Castro.

Speaker 1 And the CIA guys like this idea.

Speaker 1 So by October of 1960, this mobster Traffic Conte says that, well, he's got a well-placed spy in Havana who's got access to the highest reaches of Cuba's government, who could be used to deliver the pill.

Speaker 1 And the plan that kind of develops is to use Cuban exiles in Miami who will get in touch with this asset and pass the pills to this disaffected member of the Castro government in Havana.

Speaker 1 And while waiting for the CIA to fabricate the pills, because then this gets kicked back to the technical services division, Giancana kind of starts to freelance a bit and it does seem like he sent a crooked cop and a woman into Cuba posing as a couple to try to poison Castro just to see if he could take a swing at it.

Speaker 1 But allegedly, they're not able to actually get close to the Cuban leader. It's been debated at how central the assassination

Speaker 1 work stream was to the overall covert action effort because it does seem like it's a second track.

Speaker 1 And yet at the same time, it's potentially a really critical track in this effort to overthrow or eliminate Castro.

Speaker 9 Yeah, because they're kind of keeping them separate. And some people don't know about the assassination track.
That's obviously kept more secret.

Speaker 9 But as the kind of plans will eventually develop, which I'm sure we'll see, there is a view that the two need to come together. You might need both to happen in order to kind of affime change.

Speaker 9 in Cuba because the the other track the kind of training the paramilitary force and the kind of more straightforward covert operation, that's still moving forward, isn't it?

Speaker 9 And the kind of training is developing and they're trying to put in place this paramilitary force to actually launch an invasion or some kind of paramilitary move on Cuba.

Speaker 1 Yeah. And so the question here is, well, where are you going to do the training, you know, once you've recruited these guys in Florida?

Speaker 1 And by July of 1960, the CIA has cut a deal with the Guatemalan president, his friend, to take over a segment of a large coffee plantation spread across 5,000 acres on the flanks of a volcano on the Pacific coast.

Speaker 1 It is called Base Tracks, and this is going to be the kind of home base for the paramilitary training component of the covert action program. And so, American trainers and the Cuban recruits move in.

Speaker 1 There's about, after the screenings and all of this, there's about 150 Cubans who have come initially. They actually set to work building the base because there's not a base there.

Speaker 1 And that summer, as you have this kind of increasingly a flood of Cuban exiles showing up in Miami, the recruitment pool potentially for this paramilitary group really grows.

Speaker 1 And the way that this group is staffed, just to kind of walk through how you wind up training to invade Cuba in Guatemala, there's actually a political front office in Miami.

Speaker 1 You mentioned the Frente, you know, this kind of revolutionary front, anti-Castro front.

Speaker 1 So you'd show up at the Frente office in Miami, potentially after having been maybe tapped by the CIA, who's now running a big station down in Miami, to show up.

Speaker 1 You get a background check, you get a psychological test, and then a few days or maybe weeks later, your phone will ring and you'll be asked to show up at an appointed hour at the frontee office.

Speaker 1 You'll be issued uniforms, some equipment, then driven in the darkness to a nearby air base. You'll get on an unmarked C-54 with darkened windows.

Speaker 1 That plane will be piloted by men with a vague Eastern European accent. Jim Rassenberger, in his book on this hilariously notes that it's in fact Poles who are flying the C-54s.

Speaker 1 And then you fly to Guatemala and the recruits though will think they're in the Dominican Republic or will be told that they're in the Dominican Republic.

Speaker 1 Now initially many are disappointed at how small the brigade is. You get the sense that maybe the recruiters in Miami were telling these guys that it's gigantic and it's an army.

Speaker 1 It's hundreds of people, it's not thousands. It's incredibly rustic quarters.
Initially, they have to bathe in the swimming pool. The whole day is really devoted to training and exercise.

Speaker 1 And this group comes to be known as Brigade 2506.

Speaker 1 Everyone in the brigade is given a serial number. And interestingly, the serial numbers begin at 2,500.

Speaker 1 So if anything leaks, Castro would think this brigade is much larger than it actually is. And during their time in Guatemala, the brigade takes long marches up the side of the volcano.

Speaker 1 And on one of these, a very popular recruit actually tragically fell to his death. And his serial number was 2506.
And so the brigade takes that name on, their brigade 2506.

Speaker 1 And this is going to be the paramilitary asset of the Central Intelligence Agency that is going to eventually try to invade Cuba at the Bay of Pigs.

Speaker 9 I mean, it must be obvious to them that this kind of ragtag, maybe that's a bit harsh to call them ragtag, ragtag, it's a bit of a cliche, but this group of hundreds of only recently recruited and trained fighters are not necessarily going to be capable of overthrowing Castro and his government, which have now had time to kind of entrench themselves.

Speaker 9 I mean, surely that's got to become obvious to them and to others pretty quickly.

Speaker 1 I think this does become obvious to the CIA pretty quickly. What happens is the small stuff is not working.

Speaker 1 I mean, the rebels inside Cuba or these small clandestine cells are much weaker than I think the CIA had originally believed.

Speaker 1 The first attempts really to link up with anti-Castro forces inside Cuba have failed miserably.

Speaker 1 I mean, the CIA has tried to put men onto the island by boat, and Castro's troops have picked them up within a day or two.

Speaker 1 I mean, Bissell talks in this period about how basically any time they put a team into Cuba, they would just disappear. They wouldn't be heard from again.

Speaker 1 So the small kind of paramilitary and covert stuff isn't working. And so what's happening actually is that the CIA is thinking, well, we actually need to go bigger.

Speaker 1 And in October of 1960, the agency has gotten a new budget approved to expand the program. Remember, it was initially about $4.5 million.

Speaker 1 Now they think it's going to be $13 million.

Speaker 1 And the focus is starting to kind of drift into a kind of full-blown amphibious invasion. of Cuba with as many people as the CIA can get their hands on.

Speaker 1 So you kind of see that the agency is realizing we're going to have to go bigger to accomplish the political objectives you've laid out for us in the Covert Action Program.

Speaker 9 Yeah. So you originally had a Covert Action Program, which is just some guerrillas and they'll kind of help topple the regime.
Maybe assassination will help.

Speaker 9 Now they're thinking we're going to need an actual invasion force. We're going to need kind of military cover.
That's maybe not quite been conveyed to the political class at this point.

Speaker 9 And of course, we're in the middle of the election when a new president is about to be selected.

Speaker 1 I think, though, that what you can see in the approval of the larger budget is

Speaker 1 maybe it's tacit, but an understanding on the part of the Eisenhower administration that to accomplish the objectives, you do have to go a bit bigger. You know, you've got to spend more money.

Speaker 1 You've got to recruit more people. And you're going to have to do things like, for example, put together a small air force.

Speaker 1 I mean, the agency secures an air base for the brigade in Nicaragua at Puerto Cabezas.

Speaker 1 And basically, in the run-up to the election, on November 4th of 1960, there's a cable sent to the base in Guatemala where the training is happening saying we're not going to do these infiltration things anymore.

Speaker 1 The focus is going to shift to creating an assault force, which is going to consist of infantry battalions, each having about 600 men.

Speaker 1 So we're not going to kind of go into Cuba as guerrillas, but we're actually going to seize and defend a lodgement by amphibious and airborne assault. So we're going to take a piece of Cuban territory

Speaker 1 by force and hold it.

Speaker 9 This is the kind of epitome of mission creep, though, isn't it?

Speaker 9 Eisenhower has asked for a kind of covert plan to do this, and suddenly you're talking about an amphibious invasion and holding a piece of territory with a small army.

Speaker 1 Well, one man's mission creep, Gordon, is another man's flexibility when the facts on the ground change. Think about the position that Vicki Bissell is in right now as you get to November 1960.
So

Speaker 1 the small stuff that he had built the original plan around, for the most part, is not working. Castro's grip is tighter.

Speaker 1 The intelligence that's coming in in 1960 is basically saying that Castro's grip on the regime is pretty solid. And we don't see a lot of credible opposition to him in Cuba outside of the regime.

Speaker 1 As the agency, you're still being tasked by... Eisenhower to come up with ways covertly to overthrow Castro.
So you you still have this burden. You kind of have to go bigger.

Speaker 9 But I guess the crucial point here is the election, though, isn't it? It is the fact that in November, JFK is going to win the election and suddenly he's going to inherit this plan.

Speaker 9 And it's not necessarily going to be clear to him, I would suggest, what the plan actually means and involves.

Speaker 9 It's the kind of fact this is all happening at a transitional moment, which I think is going to be part of the story that effectively dooms it and perhaps even dooms JFK.

Speaker 1 I couldn't agree more because by this point in November of 1960, the Eisenhower administration has been thinking about Cuba for several years and has been in the middle of covert action programming since March.

Speaker 1 So for a long period of time, and there would be real comfort. I mean, not actual comfort, but there'd be an understanding of the details of the plan, what the CIA is up to, all of that.

Speaker 1 With Kennedy now winning the election in November, Dulles and Richard Dickie Bissell go and brief Kennedy a few weeks after the election in kind of general terms on the Cuba work.

Speaker 1 And I think here it's safe to say they probably did get him up to speed that there is some covert action planning going on. In January of 61, the U.S.
officially terminates.

Speaker 1 diplomatic relations with Cuba. The CIA station in Havana, because think about it, we had an embassy there the whole time.

Speaker 1 So there's been a station in Havana, which by coincidence had just received a new incinerator. They burn everything that can't be shipped out to Key West.
Embassy closes.

Speaker 1 And Kennedy meets a couple of times with Eisenhower during the transition. And Eisenhower tells Kennedy that the CIA is helping anti-Castro guerrilla forces to the utmost, and that the U.S.

Speaker 1 is currently training such a group, Brigade 2506, in Guatemala. Eisenhower says, in the long run, the U.S.
cannot allow the Castro government to continue to exist in Cuba.

Speaker 1 And I think, as we'll see, JFK is going to agree mightily with that statement.

Speaker 9 So there, I think, with John F. Kennedy in the presidency, about to be faced with a decision which will have huge consequences for his life and his death, perhaps.
Let's leave it.

Speaker 9 Just a reminder, of course, if you want to hear this whole series,

Speaker 9 you can do so by becoming a member of the Declassify Club at therestisclassified.com.

Speaker 9 And you'll get access to our special mini-series looking at some of the theories and some of the questions and perhaps even some of the answers, David, around the assassination of JFK.

Speaker 9 And the first episode of that will be out this Friday if you want to join the club or you're already a member. But otherwise, we will see you next time.

Speaker 1 See you next time.

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