Michael: Alright Kevin, if you had to describe U.S.-Cuba relations for the last 60 years in one word, what would it be? Kevin: Awkward. Like a family reunion where one cousin tried to overthrow the other cousin's government... and they both have to be at the same dinner table for half a century. Michael: That's... surprisingly accurate. And it's the perfect setup for the book we're diving into today: Back Channel to Cuba: The Hidden History of Negotiations Between Washington and Havana by William M. LeoGrande and Peter Kornbluh. Kevin: Okay, so this isn't just another history of the embargo and the Bay of Pigs, right? This feels different. Michael: Exactly. These authors are basically the Indiana Joneses of declassified documents. Peter Kornbluh directs the Cuba Documentation Project at the National Security Archive. They spent over a decade digging up secret files and interviewing everyone from Fidel Castro himself to U.S. presidents to tell the story that was happening behind the public shouting matches. Kevin: Wow. So they got the actual receipts. Michael: They got the receipts. The book was widely acclaimed, won diplomatic history awards, and it completely reframes the narrative. It argues that what Henry Kissinger once called the "perpetual antagonism" between Washington and Havana was, in fact, a myth. Kevin: A myth? The whole thing? I mean, it seemed pretty real from the outside. Michael: The public hostility was real, absolutely. But underneath it, there was this constant, secret conversation happening. And that hidden dialogue is where the real story is.

Michael: Let's start with the most dramatic example, which comes from the Kennedy administration. This is right after the Bay of Pigs disaster and the Cuban Missile Crisis, a moment when the world literally held its breath, thinking nuclear war was imminent. Kevin: Right, the absolute peak of hostility. You couldn't get more adversarial than that. Michael: You would think. But at that very moment, President Kennedy's brother, Robert Kennedy, sends a private lawyer named James Donovan to Havana. His official mission is to negotiate the release of prisoners from the Bay of Pigs invasion. Kevin: Wait, James Donovan? The guy from the movie Bridge of Spies? That guy? Michael: The very same. He was a master negotiator. And while he's in Havana, he builds this incredible rapport with Fidel Castro. They have these long, candid conversations. And during one of them, in early 1963, Castro turns to Donovan and asks a stunning question. He says, "If any relations were to commence between the U.S. and Cuba, how would it come about and what would be involved?" Kevin: Whoa. So Castro himself is opening the door, asking for a roadmap to peace, just months after the Missile Crisis? That’s unbelievable. Michael: It's a bombshell. And Donovan's response is pure genius. He looks at Castro and says, "Do you know how porcupines make love?" Castro says no. And Donovan replies, "Well, the answer is ‘very carefully.’ And that is how you and the U.S. would have to get into this." Kevin: That's a perfect analogy. It captures the danger, the prickliness, the need for caution. It’s brilliant. But it also shows a real willingness on both sides to at least think about it. Michael: It does. It shows that even at the height of the Cold War, pragmatism could find a way. Both leaders recognized they were stuck with each other, 90 miles apart. A perpetual state of war wasn't sustainable. This conversation opened the very first secret back channel of the Kennedy era. Kevin: Okay, that alone changes my entire perception of that period. But it sounds too good to be true. There has to be a catch. Michael: Oh, there's a catch. And it's a catch that defines the entire 50-year story. While James Donovan is having these delicate "porcupine" conversations on behalf of the White House, another part of the U.S. government has a very different plan for him. Kevin: I have a bad feeling about this. Michael: The CIA's covert operations unit—the "executive action" folks, which is a euphemism for the assassination squad—sees Donovan's access to Castro as the ultimate opportunity. They devise a plot. Donovan was an avid scuba diver, and he planned to give Castro a custom wetsuit and a snorkel as a gift. Kevin: Oh no. Don't tell me. Michael: The CIA's plan was to contaminate the breathing apparatus of the snorkel with tubercle bacillus, to give Castro a debilitating respiratory disease. And for good measure, they would dust the inside of the wetsuit with a fungus that would cause a chronic skin disease. They were going to turn Donovan, the peace emissary, into an unwitting biological weapon. Kevin: That is pure, uncut, spy-movie villainy. It's insane. So one arm of the government is trying to make peace, and the other is literally trying to poison the guy at the other end of the table? How does a government even function like that? Michael: It barely does. And that's the core of the book's findings. The only reason the plot failed is that Donovan's own CIA handler, a man named Milan Miskovsky, found out about it. He was horrified that the agency would try to use their own negotiator as an assassin. He intervened and made sure the contaminated gifts never reached Donovan. Kevin: So Donovan never even knew he was almost used as a hitman? Michael: He never knew. But Castro found out years later and was, as you can imagine, absolutely furious. He said, "They tried to use him as the instrument... the lawyer who was negotiating the liberation of the prisoners!" It perfectly illustrates the deep, almost schizophrenic contradiction in U.S. policy. Kevin: Schizophrenic is the right word. It’s like the right hand doesn't know what the left hand is plotting. It sets up an impossible situation. You can't build trust when there's a literal poison plot happening in the background. Michael: Exactly. And that dynamic, that tension between the pragmatists seeking dialogue and the hardliners seeking destruction, is the engine of this entire hidden history. It wasn't just a Kennedy-era problem; it plagued every single administration for the next five decades.

Kevin: Okay, so that story is the perfect microcosm of the problem. You have people trying to build a bridge, and others simultaneously trying to blow it up. What were the main forces that kept sabotaging these efforts? Michael: The book lays out a few key "saboteurs," and the first one is exactly what you'd expect: domestic politics in the United States. No president wanted to look "soft on communism." It was political poison, especially with the rise of the powerful Cuban-American exile community in Florida, which was staunchly anti-Castro. Kevin: The political pressure must have been immense. Michael: It was. Take Richard Nixon. Before he was president, as Vice President under Eisenhower, he met with Castro during his 1959 goodwill tour to the U.S. The meeting was a disaster. Nixon basically lectured Castro like a school principal, warning him about communists. Castro left the meeting feeling insulted. Kevin: I can't imagine Castro takes well to being lectured. Michael: Not at all. And Nixon came away convinced that Castro was a dangerous enemy. He wrote a memo saying Castro had those "indefinable qualities" of a leader but was ultimately "inimical to U.S. interests." Within weeks, Nixon became one of the biggest advocates inside the Eisenhower administration for a policy of overthrowing Castro. That impulse never left him. Years later, as president, he told Kissinger he never, ever wanted to hear about normalizing relations with Cuba. Kevin: So his personal animosity, fueled by that one disastrous meeting, shaped U.S. policy for years. It shows how much the personalities of leaders matter. Michael: Immensely. But it wasn't just U.S. politics. The book is fair in showing that Cuba was far from a passive player in this drama. Castro was a master of geopolitics, and he often made moves that directly undermined any progress toward peace. Kevin: What's a good example of that? Michael: The biggest one is probably Cuba's military intervention in Angola in the mid-1970s. At the time, Secretary of State Henry Kissinger was secretly conducting the most promising talks with Cuba in years. They were making real progress. They'd signed an anti-hijacking agreement. Things were looking up. Kevin: Okay, so there was real momentum. Michael: There was. And then, in 1975, Castro sends thousands of Cuban combat troops to Angola to support the Marxist MPLA movement in their civil war. From the U.S. perspective, this was an outrageous provocation. Cuba, a small island nation, was projecting military power in Africa and directly challenging U.S. interests. Kevin: And that just blew everything up. Michael: Completely. President Ford was furious. Kissinger felt betrayed. The secret talks collapsed overnight. The U.S. went from exploring détente to contingency planning for military action against Cuba. Castro later argued he was supporting a legitimate anti-colonial movement, but in Washington, it was seen as a deliberate choice to prioritize revolutionary adventure over normalizing relations with the United States. Kevin: It's that "awkward family reunion" again. Just when you think you might be able to talk civilly, one cousin decides to send an army to Africa. It's a pattern of one step forward, two steps back. Michael: It is. And the authors, LeoGrande and Kornbluh, are really good at showing this isn't a simple story of U.S. aggression and Cuban victimhood. It's a complex dance where both sides made choices that prolonged the conflict. They document how these back-channel talks would gain momentum, only to be derailed by a CIA plot, a domestic political firestorm in the U.S., or a provocative foreign policy move by Castro. Kevin: The book sounds incredibly well-researched, but given that it focuses so much on the failures of the U.S. hardline policy, did it face any criticism for being, say, too sympathetic to the Cuban side or too pro-negotiation? Michael: That's a great question, and it's something critics have pointed out. The book's narrative is definitely driven by the belief that dialogue is better than isolation. The authors are, by their own admission, advocates for engagement. However, they build their case on a mountain of declassified evidence. They're not just offering an opinion; they're documenting a history that was deliberately hidden. They show that every president, even hardliners like Reagan, eventually found it necessary to talk to Cuba on some level, whether it was about migration, drug trafficking, or peace in Southern Africa. The talks were a diplomatic necessity. Kevin: So their point isn't that Castro was a saint, but that refusing to talk was an illogical and ultimately failed policy. Michael: Precisely. They let the historical record speak for itself. And the record shows 50 years of a policy that failed to achieve its main objective—regime change—while closing the door on opportunities for cooperation on issues of mutual interest.

Michael: When you pull back and look at the whole fifty-year arc, the story of Back Channel to Cuba is really about the clash between two opposing forces: ideology and pragmatism. Kevin: The ideologues who wanted total victory versus the pragmatists who just wanted to solve problems. Michael: Exactly. The hardliners in both countries saw the conflict as a zero-sum game. One side's gain had to be the other's loss. But the negotiators in the back channels, the Donovans of the world, understood that some issues—like preventing hijackings or managing migration—required cooperation. They were trying to find the small spots of overlapping interest in a vast sea of disagreement. Kevin: And they just kept getting overruled by the bigger political forces. Michael: Time and time again. There's a beautiful quote in the book from Raúl Castro, Fidel's brother. In 1977, he was talking to some U.S. senators, and he used a powerful metaphor. He said, "Our relations are like a bridge in war-time. I’m not going to talk about who blew it up... The war has ended and now we are reconstructing the bridge, brick by brick... It is not a bridge that can be reconstructed easily, as fast as it was destroyed. It takes a long time. If both parties reconstruct their part of the bridge, we can shake hands without winners or losers." Kevin: Wow. "Brick by brick." That perfectly captures the slow, painstaking, and fragile nature of the work these secret diplomats were trying to do. Michael: It does. And for decades, it felt like for every brick they laid, someone would come along and knock two down. The book's ultimate power is that it reveals this hidden history of construction. It shows that the eventual normalization of relations under President Obama wasn't a sudden miracle. It was the culmination of fifty years of secret, patient, brick-laying by people on both sides who believed a different relationship was possible. Kevin: It really makes you wonder, doesn't it? How many other global conflicts that seem like black-and-white standoffs have this hidden layer of conversation, this secret history of people trying to build a bridge? Michael: It’s a profound question. This book suggests that behind the headlines and the political posturing, there's often a more complex and more human story unfolding in the shadows. It’s a reminder that even between the most bitter of adversaries, the conversation never truly stops. Kevin: A fascinating and, in a weird way, hopeful thought. Even in the most awkward of family reunions, someone is still trying to pass the salt. Michael: We'd love to hear what you all think about this. Does this hidden history change how you view U.S.-Cuba relations, or even international diplomacy as a whole? Drop us a line on our socials and join the conversation. Kevin: This is Aibrary, signing off.