The Old Man and the CIA, Part 2: Dulles's Down | Historical
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Content warning: This episode contains references to suicide. Incoming transmission. Welcome. This is True Spies. The podcast that takes you deep inside the greatest secret missions of all time. Week by week, you'll hear the true stories behind the operations that have shaped the world we live in. True Spies. You'll meet the people who live life undercover. What do they know?

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This is True Spies. Dulles himself was a very arrogant guy. I think he was stunned by Kennedy, how stubborn he was, how resolute he was, how he stood his ground at the Bay of Pigs. I think that he thought Kennedy would pave, and he didn't. And I think he was shocked by that. I'm Sophia DiMartino, and this is True Spies from Spyscape Studios.

The Old Man and the CIA, Part Two: Dulles's Downfall. Allen Dulles played both sides of the fence during the 1960 presidential campaign in this country. On the 24th of May, 1959, Allen Dulles's closest ally was wiped from the chessboard. His brother, Secretary of State John Foster Dulles, died after a years-long battle with cancer.

With an election looming and a new president certain, the director of Central Intelligence realized that change was about to arrive in the White House, and he should take the necessary steps to weather it. A lesson he'd taken to heart after he'd backed the wrong horse before Truman's election, and subsequently endured a stint out in the cold.

And so this time, like any wise gambler, he spread his bet. He supported Richard Nixon quietly and quietly also supported a young John Kennedy. Vice President Richard Nixon, who the Dulles brothers had mentored since his earliest days in politics, might have been Allen's obvious first choice. He was, after all, a staunch Republican.

But he saw no cause for concern in the handsome upstart on the other side of the aisle. Now, Kennedy ran in 1960 as a cold warrior. Let's not forget, in some ways, he was tougher even in his rhetoric than Richard Nixon. I feel that the Kennedys knew how to win. They were not about to be Adlai Stevenson, the softer Democrat who had lost to Eisenhower twice.

They were not about to be beautiful losers. They were going to be tough, and they would do what they had to do to win. The Kennedy brothers were raised that way. So in some ways, JFK, he said as an inauguration speech, of course, we'll pay any price, fight any foe around the world. He talked tough. Alan Dulles liked that tough talk.

What's more, the Kennedys were part of the same elite to which he belonged. They were a known entity. They moved in somewhat the same circles beforehand, Dallas and Kennedy. They were both men who were comfortable with world wealth in Florida, in New York, and so forth.

And Dulles knew young Jack personally, just as he'd known his father. Old Joe Kennedy, Kennedy's father and patriarch of the family, had brought Alan Dulles down to brief his son a couple times at least when he was a young senator. One time after he had undergone back surgery and almost died, young Kennedy, Dulles was there.

In other words, Allen Dulles was convinced he could work with either of the candidates in the 1960 election. So perhaps I was wrong to compare him to a gambler. Maybe he was more like the casino. After all, the house always wins. In a sense, he didn't care which one would win.

He thought if Kenny win, he could influence them all. He was young, he was naive, and he would be putty in his hands. In the first part of this story, you got to know Alan Dulles, who became, in 1953, the first civilian director of the CIA. There, he was affectionately referred to as the old man. But don't let his grandfatherly appearance deceive you.

By the historian David Talbot's account, he is one of the most important and ominous figures in America's 20th century. A master puppeteer, fluent in the language of secret influence. Allen Dulles had already exerted that influence on Eisenhower during his two terms in the White House, luring the aging president into supposedly bloodless coups in countries like Iran and Guatemala.

And now, with a new president entering the Oval Office, he was prepared to continue the CIA's shadowy campaign against the global scourge of communism.

But in presuming Kennedy malleable, he was to make the mistake of his career. I think he thought of him as an acolyte, someone who could bend his will. Dulles himself was a very arrogant guy. I think that he thought Kennedy would cave, and he didn't. And I think he was shocked by that. Alan Dulles will not have to wait long to discover how sorely he has underestimated John F. Kennedy.

The flashpoint of their conflict will come with a backdrop of one of the most spectacular fiascos of the Cold War: the Bay of Pigs invasion. If David Talbot is to be believed, the seeds of both men's ruin will be sown on that storied beach.

But we're getting ahead of ourselves. Even before the Bay of Pigs, there were signs that JFK would not extend the same impunity to Alan Dulles that his predecessor had offered. The very first break between the CIA and President Kennedy comes even before Kennedy is sworn in, and that's with Patrice Lumumba.

Patrice Lumumba became in 1960 the very first democratically elected prime minister of the Congo. A committed African nationalist, he was determined to see his country emerge from the brutality of its colonial past.

JFK, who was a vocal supporter of the African independence movement, saw in Lumumba a kindred spirit of sorts. An inspiring, charismatic leader committed to real change. But his hope for Lumumba and the Congo was to be cut short when just months after his victorious election,

This young nationalist leader who was the hope of the third world in some ways is taken prisoner by his political enemies, tortured and brutally killed.

There's a picture taken by a young photographer that Kennedy had engaged to document his first days in office, of the moment that the new president heard the news of Lumumba's fate. And his face is crumpled into his hands as he gets the news about Lumumba being brutally killed. It will be abundantly clear to anyone looking at that photo that Kennedy is shocked by the news, but he shouldn't be.

LaMamba's demise has been orchestrated by his own intelligence services and authorized by his predecessor. Again, a coup that's backed by the CIA. And the CIA doesn't want President Kennedy to find out because they know President Kennedy will probably intervene on the imprisoned LaMamba's behalf.

And now that their dirty work has been done, the CIA still don't have the decency to let the new president know about the act that has been carried out in his name. The news does not come from the CIA. It comes from his UN ambassador, Adlai Stevenson. It's unclear when, or indeed if, JFK ever grasped the truth behind Lumumba's assassination.

Perhaps he already had his suspicions that Alan Dulles' CIA was out of control. Or perhaps he was too distracted by the ever-escalating situation in Cuba and its increasingly radical leader, Fidel Castro. As a senator, JFK had nurtured a cautious respect for the Cuban Revolutionary. Maybe he recognized something in Castro, too. There is a symmetry between the two young leaders.

They're both young. They're both nationalists. They're both progressive in their way. I believe Fidel Castro was not a full-fledged communist at the moment. He was in evolution politically. They were both Catholic. They were both the sons of wealthy families. And they were both very charismatic.

The same could not be said of Alan Dulles, who saw nothing that he liked about Fidel Castro. Castro was something he'd never come across before. He was a charismatic, very popular nationalist hero at home. And he had a following in the U.S. as well. When he came here in 59 and later in 60 during the presidential campaign, you know, crowds followed him everywhere.

Fidel Castro also had a gift for public relations. When he came to New York in 1960 as the head of the Cuban delegation at the United Nations, he was turned away from every hotel in midtown Manhattan, an embarrassment that had the fingerprints of the CIA all over it.

He ended up staying at the Teresa Hotel in Harlem in 1960. And celebrities came up there to see him. Khrushchev, I believe, came up because it was during the United Nations annual summit meeting. And Malcolm X famously met him. In the midst of his rejection, Castro found an opportunity to throw his support behind the civil rights movement.

and the charismatic revolutionary Malcolm X. So this was, of course, a great threat to people like Delos, to the establishment.

Because the civil rights movement, the Melvin civil rights movement, was now on the verge of making a pact with our mortal enemies overseas, with Fidel Castro. Though Kennedy had to take a tough stance on Cuba publicly, he clearly admired Castro's instinct for political opportunity.

Enough so that he followed in the revolutionaries' footsteps a few months later when he visited the Hotel Teresa on his own presidential campaign trail. Kennedy does go to the Hotel Teresa during the campaign in '60, right after Castro has been there, and he gives his own very progressive speech talking about how to be a Black child in this country is penalized, is a terrible burden for any Black family.

because of the racism in this country. His rhetoric is very progressive. Indeed, by David Talbot's estimation, these two leaders, ostensibly opponents, fundamentally understood one another. They were offering different paths to the same destination. So I think in ways Kennedy and Castor were offering Latin America in particular the competing visions for how you reform your country.

And Kennedy, of course, tried through the Alliance for Progress to strip the power from the oligarchies, from the backward interests that ran these countries, the military and wealthy landowners. And Castro, of course, did in Cuba at the point of a gun. John F. Kennedy was no revolutionary, but he understood the distinction to be largely a matter of context.

His American privilege meant he didn't have to take up arms to bring about the change he felt necessary for his country.

Kennedy thought that was not the way to do it, but he sympathized with Castro's aims and he sympathized with Chile, with the countries where anaconda copper in that case ruled. He told Dick Goodwin, his aide, when he was president of Kennedy, that if I had been raised in Chile, where the copper companies, foreign companies own all my resources, I'd be a revolutionary too.

But where Kennedy may have harbored some sympathies to the Cuban cause, Allen Dulles saw another communist wildfire in need of quick extinguishing.

Good American business had been heavily invested in Cuba, even more so than Guatemala, where the CIA had fomented a coup in 1954. Cuba, of course, not only was a home for U.S. interests, corporate interests, the Rockefeller brothers, Standard Oil, United Fruit, and so on, all of whom had been clients of the Dulles brothers, all of whom had been their corporate CEOs very close to the Dulles brothers.

But of course, Havana was also the gambling mecca in those years. Very important to organize crime, the mafia in this country as well, that ran those prostitution businesses, that ran the casinos and gambling interests in Havana. And of course, Castro got rid of most of that and expropriated their assets, these corporate clients of the Dulles brothers.

If you're curious to hear how the CIA leveraged the Mafia's disdain for Fidel Castro in their ongoing war against Cuba, I'd encourage you to listen to our earlier True Spies series, The Oswald Project. It will help you understand the lengths Dulles was prepared to go to to resolve the Cuban situation once and for all.

It would be no stretch to say that there was a hit-out on Fidel Castro long before Kennedy ever made it to the White House. There are plots to kill him, to assassinate him, and the CIA has those plots as well. But they also have the plan already in motion to invade his country at the Bay of Pigs.

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Like the Congo coup that saw Patrice Lumumba killed, the Bay of Pigs operation had been developed by Alan Dulles and authorized by President Eisenhower.

And he convinced the Eisenhower presidency that they should invade, that the CIA should sponsor invasion of Cuba and overthrow Fidel Castro. That was then handed over to President Kennedy, who was elected. Unlike the Congo coup, the Cuban invasion would need Kennedy's explicit approval to go ahead.

Allen Dulles convinced him that the Bay of Pigs operation was underway, that it was slam dunk, that it was easy, they were going to get rid of Castro and move on. The plan, as it was laid out to John F. Kennedy in the early days of his presidency, was as follows: A crack team of 1,400 Cuban exiled soldiers trained by the CIA would launch a surprise invasion at the Bay of Pigs.

Quickly and efficiently, they would dismantle Castro's regime and install a puppet leader. Just as they had in Guatemala. Remember, no matter what sympathies Kennedy might have harbored for Castro, he had campaigned as a cold warrior.

Allen Dulles suggested this was his opportunity to put his money where his mouth was. And he convinced Kennedy this operation could be carried out with a minimum of noise, which Kennedy had said he didn't want to be a very loud operation, a global kind of incident. He wanted this to be very local and very quiet. So Allen Dulles said, no problem, that's the way we'll operate. It's clear that Kennedy was in two minds about the plan.

Indeed, some of his closest confidants had their doubts it could go off in the way that Dulles was promising. I think that there were opponents of the invasion, but I think Kennedy was rolled by the CIA largely, was convinced there would be an easy operation and that he could go in without escalating. But according to David Talbot, Dulles always had other intentions.

I believe the 1,100 or so people who Allen Dulles and the CIA blamed on the beaches at the Bay of Pigs were meant to fail. They were a hapless crew. They were certainly not run by the A-level people, as the internal report said later at the CIA. It was meant to get bogged down on the beaches, this invasion. And then Kennedy would be forced to send in the Air Force and Marines.

to save this botched operation. It's a bold accusation, and yet it's one that might make sense of the famously catastrophic events of the 17th of April, 1961. When Dulles' elite unit stormed the Bay of Pigs, they found themselves grossly unprepared for the task at hand.

Castro's revolutionary army had benefited from intelligence that pointed towards an impending invasion and even revealed its planned location. In other words, they were ready. The casualties came thick and fast, as did the captures. Immediately it became apparent that the invasion would fail unless Kennedy was prepared to escalate the operation.

Alan Dulles tells him this is the only route forwards. They're cocked and ready to swing, the US military. The Navy, the Air Force, they're ready to go in at any point to get rid of this noxious person, Fidel Castro. Remember, Talbot says this was Dulles' plan all along. He has handed Kennedy a grenade with the pin pulled. What choice does this green president have but to throw it?

But during the frenzied White House briefings on the rapidly deteriorating operation, it becomes clear that Dulles has underestimated Kennedy. I interviewed his brother, Teddy Kennedy. I interviewed also a number of people who worked for him in the White House, including Ted Sorensen, his speechwriter.

Both of them said to me the main reason that John Kennedy, JFK, ran for president in 1960 was he, as a student of history, he was quite aware how great powers could stumble into military catastrophes. He'd read about World War I, and he knew the stakes were even higher in the nuclear age. And so he was definitely afraid of an accidental nuclear war breaking out.

Cuba is the hot spot, Cold War hot spot. Thought that it would happen there. He thought it would happen around the Bay of Pigs. Dulles has expected the young president to be malleable. But now, in this hour of crisis, he was beginning to understand the gravity of his mistake. Kennedy refused to go down in history as the president who made the Cold War hot.

I believe JFK was quite aware of the dangers that he was up against as president and the kind of forces that were pushing him towards a war, a showdown with the Soviet Union, from his military, from his intelligence advisors, was disastrous financially.

I believe also as someone who had served in the military, and of course he was a young naval officer during World War II, he was used to actually having contempt often for military commanders. And he said, you know, later on as president, these guys come into my office, they have all the salad, meaning, you know, ribbons on their chest. And I just told him, no, I stood up to them.

By this point, I don't need to tell you that Alan Dulles did not like hearing the word "no".

Just where exactly did Kennedy get the gall? I think because of his own wealth, his own sense of entitlement, his own family he'd grown up in, his own military service during the war. He lost a brother during that war, of course, in an Air Force explosion. You know, he later said that Kennedy seemed destined for great things before the war.

the war made it very clear that we were just human like everyone else. I think there was a certain humility about him, a strength but humility. And he knew what the stakes were. He knew what the nuclear stakes were. Dulles has assembled the top brass of the U.S.'s armed forces and national security advisors. All of them are saying the same thing. Kennedy must finish what he has started at the Bay of Pigs.

Virtually everybody in the room, all of his national security advisors were telling him to take a hard line. Only his brother, maybe one or two others, had the courage to back the president. But the president will not be swayed. He stunned Alan Dulles. He stunned the military, the hardliners.

President Kennedy by saying, no, I will not send in the Marines. I will not send in the Air Force. I will not make this a wider war. The Soviet Union could move on Berlin to counter this assault, this full-fledged assault on Cuba. He thought it could become a global incident.

So he refused to go along with it, and they were stunned. The hardliners like Delos were stunned by Kennedy's refusal to expand this operation and to save the 1,100 men who were bogged down at the beach, most of whom were rounded up and put in prisons for a time. With more than 100 deaths and 1,000 men captured and imprisoned, this supposedly quiet operation suddenly became very loud indeed.

The Bay of Pigs invasion had been an unmitigated disaster, and it was splashing in newspapers around the world. Cue the game of responsibility hot potato. There was an effort by Dulles' friends in the media, of course, to say there's a Kennedy failure of nerve, and they fought it out in public. Who was going to take the blame for it?

But Kennedy, you know, said as president, "The buck stops here. I will take blame for it." John F. Kennedy may have publicly accepted the blame for an operation that he'd been tricked into, but behind the scenes, it was a different story.

Kennedy was outraged and said he would shatter the CIA, famously said, and scatter to the winds as a result of him being misled by the CIA and by the generals before the Bay of Pigs. The debacle represented a first in the career of the great spymaster. It was an abject defeat. It was the first, I think, great humiliation in Delsa's career, and he never really got over it.

I think because of Bobby Kennedy, the president's brother, who was attorney general, through his own efforts, that blame was pinned where it should be, on Dulles, on the Dulles regime of the CIA. And Kennedy quickly made good on his promise to shatter the CIA and scatter its pieces to the wind. He starts with Dulles himself. He is forced out of office by President Kennedy by the end of 1961.

And he had served every president since Woodrow Wilson, so he was stunned by this upheaval in his life by being suddenly jettisoned this way. It is ostensibly the end of Alan Dulles' career. The spymaster has permitted the fanfare of a glitzy farewell ceremony, more salad for his laden chest. But make no mistake, he's out in the cold.

At least that's the official version of events. Talbot says otherwise. Allen Dulles is used to being in power. I think he went home to his house in Georgetown and he continued to operate as if he were still DCI. People came to him and related to him, deputies and aides to the CIA, as if he were still running the agency.

I think John McCone, whose candidate is for placement for him, was in over his head, didn't really know what was happening at the spy agency. I think people like Dick Helms, James Angleton and others who are actually at the agency at the high level continue to think of Dulles as, quote, the old man, which was the affectionate nickname they gave him as their true leader.

Meanwhile, Kennedy has not seen his last trial as president. Again, the flashpoint is Cuba. In October of 1962, a U-2 spy plane captures images of Soviet-built nuclear missile sites on the Caribbean island.

Kennedy establishes a naval blockade around the nation. And the world watches, terrified, as the U.S. President and Nikita Khrushchev seem to edge closer and closer to nuclear war. When I was a kid, my dad, in the middle of the October Missile Crisis, came home and said, we may not live to see the morning. Those were the kind of moments

But of course, all of this perspective comes with the benefit of hindsight.

As the crisis is spiraling in real time, Kennedy is once again encouraged by military advisers to escalate, to make an emphatic example of this cocksure revolutionary island. And when the president says no, the feelings are almost, you know, are hateful towards the president from the military commanders. They think this is a moment of cowardice, of appeasement.

And of course, Joe Kennedy, the president's father, was famously accused of appeasing Hitler during the war as the ambassador to London. So they felt once again that Kennedy had let them down and they were furious about it. It was at this point, Talbot posits, that an unbridgeable gap opened up. Not between the USA and Cuba, but between the president and his own security services and military.

Kennedy could no longer play the part of the tough, cold warrior. I think he became a man of peace, increasingly so, particularly after the terrors of the October 1962 missile crisis and the Bay of Pigs in April 1961. He thought the hardliners, like Curtis LeMay, head of the Air Force, and Allen Dulles, were more of a threat to peace than even our enemies, our Cold War enemies in Moscow and Havana.

For the remainder of his tragically short stint in office, Kennedy did what he could to declaw those threats. He had backed channels open to Havana when he was killed. He was sending reporters and diplomats, people from the administration, people outside the administration, to speak with Castro. I believe they would have come to some kind of peaceful pact.

As he would have, Kennedy would have, with the Soviet Union, he had the same back channel with Moscow. I think the CIA found out about those back channels, those secret back channels, and that was the one reason they thought Kennedy was such a threat, because he was pursuing his own diplomacy behind their backs. And he was sending people down to Havana.

Which brings us directly to the single most shocking of David Talbott's theories about Allen Dulles. The true endpoint to not only his story, but also John F. Kennedy's. I think Allen Dulles was the chief executor of the assassination of President Kennedy and also of the cover-up.

Don't forget that Ellen Dull served strangely on the Warren Commission after the assassination that investigated the murder and came to the conclusion, of course, that Lee Harvey Oswald did act it alone.

Dulles really ran that commission in some ways. He was the only high-level figure on that commission who didn't have a day job, wasn't a senator or congressman or a chief justice, who really could devote his time to running that commission, that investigation, which he did. So he ran the assassination, I believe, and the cover-up. In David Talbot's version of events, the old man never truly left the CIA.

Working quietly in the dark corridors of hidden power, he calmly and efficiently organized his revenge against the man who had tried to destroy his reputation. The man who, in his appeasement policies and peace-mongering, represented a threat to Dulles' very existence. His final flourish was to place himself at the center of the official investigation into Kennedy's assassination.

simultaneously restoring his reputation with the public and ensuring the true story of the president's murder would remain buried forever. Could it be true? Are those the strings of a master puppeteer we see in the background of one of the most shocking assassinations of all time? Like so much in this world, the answer to one riddle only creates further questions.

Was Allen Dulles a rogue? Did he do this on his own? No. He was a good officer who understood the chain of command. He answered to corporate clients, people had more power than him. But he knew how to put together assassinations. He knew how to affect regime change. He had years of experience. And he brought that expertise tragically home to Dallas in November 1963.

There's no questioning that Kennedy had made some powerful enemies during his brief time in office. Again, I'd encourage you to listen to our earlier True Spies story, The Oswald Project, for more of that context. It's also in no doubt that Allen Dulles, a man who'd always found impunity in the CIA's mandate, would have had the contacts to pull the job off.

It's always been said that Fidel Castro himself was convinced of some deeper, darker conspiracy behind the assassination. Castro himself was very stunned.

overwhelmed by the news from Dallas, said, now they'll come after me, which is true. I think that assassination in some ways was meant to trigger and all that in the military invasion of Cuba. To this day, we don't know why President Johnson didn't approve Greenlight that invasion, that assault, but I think he feared a nuclear war, rightly so.

Invasion of Cuba or no, with the arrival of Lyndon B. Johnson, America was back to business as usual. An escalating war in Vietnam, bigger and bigger stockpiles of nuclear arms, brinkmanship as the only viable politics. The window of opportunity, opened briefly by Kennedy, had slammed shut with his violent execution.

And the military-industrial complex that Eisenhower had starkly warned about in his final address as president appeared to be calling the shots once again. Maybe this is the true legacy of Alan Dulles. It's a theory that David fleshes out compellingly in his book The Devil's Chessboard, where you'll find many more stories from the prolific career of the old man and the CIA. ♪

Read it, and just like David Talbot, you'll begin to wonder what the world would look like had Dulles never found his way into the seat of secret power.

I believe that period is key to understanding America. It could have gone in two different paths. JFK briefly, of course, you know, presented a post-Cold War vision, a peaceful vision of America and the world, and we see what happened to him. I'm Sophia DiMartino.

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