Fidel Castro was one of the American government’s arch-rivals for the majority of the 20th-century. Castro was a longtime critic of American economic and foreign policy and an ally of America’s foremost enemy, the Soviet Union. As the face of Cuba for more than half a century, the American government saw removing Castro as a simple way to fix their issues with their neighbors to the south. So, they did everything in their power to kill the man, short of a full-on war with Cuba. The CIA devoted thousands of man-hours to devising creative ways to kill the Cuban leader, ranging from exploding cigars to poisoned skincare products to LSD gas and much more. Despite the more than 600 attempts, though, Castro survived. Records of the failed attempts played a significant role in influencing new law prohibiting assassinations, yet, attempts on Castro’s life continued for another 25 years afterward. How did he survive the CIA’s best efforts, and how did the US justify such unlawful actions? Let’s explore.
When Fidel Castro became Prime Minister of Cuba in 1959, the United States took notice, but it was not the first they heard of the man. The CIA had been watching Castro from a distance since 1948, when, as a young law student, he became active in widespread protests against right-wing regimes throughout Latin America. But, what made the USA so interested in a student-activist on a small Caribbean island?
Cuba sits 140 kilometers from the southern tip of Florida and less than 2,000 km from Washington DC. For the first half of the twentieth century, the island was a popular holiday location for wealthy Americans. US enterprises controlled the small country’s sugar fields, cattle ranches, mines, and oil industry. Mobsters owned hotels and casinos there, where they could operate just outside American jurisdiction. So, when the pro-American dictator Fulgencio Batista took control of Cuba in 1952, they looked on approvingly.
Not only was Batista friendly with American companies, but he ensured that the island withstood the wave of Communism that was washing over much of the world. Batista was a cruel leader. In the words of American historian Arthur Schlessinger, Batista’s “indifference to the needs of the people for education, medical care, housing, social justice, and economic justice … [was] an open invitation to revolution.” And that’s precisely what happened.
Cuban anti-Batista sentiment grew throughout the 1950s, with Castro assuming a leadership role within one revolutionary group. In 1955, Castro toured the United States in search of wealthy sympathizers to back his cause. During this trip, Batista organized an assassination plot, hoping that his geographical distance from the event would allow him to avoid responsibility. Castro evaded this first attempt on his life, but it wouldn’t be the last.
When Batista vacated the presidency in 1958, several politicians stepped in to fill the void, but none of them stuck quite like Fidel Castro. Castro became Prime Minister on the 16th of February 1959, and he immediately got to work changing the country. He nationalized many of the industries previously controlled by American companies, cut off most exports to the US, and seized the land and property that had once belonged to American gangsters and businessmen.
America could handle the economic pressure— after all, Cuba wasn’t that important of a trading partner. However, Castro’s trade deal with the Soviet Union signaled to the US that their southern neighbors may pose a different threat. Castro long refrained from openly voicing his support for Communism, but the Americans were not about to watch one of their closest neighbors cozy up to the Soviet Union. As the Cuban Missile Crisis would later confirm, the Americans feared that Cuba could serve as a launching point for Soviet missiles fired at major US population centers.
So, the US wasted no time in attempting to oust the pro-Soviet Cuban leader. Barely a year after becoming the Prime Minister, in September of 1960, the CIA organized its first attempt. In the bizarre fashion typical of the mid-20th century CIA, the agency partnered with some of America’s most notorious gangsters to try to off Castro. A CIA agent named Robert Maheu partnered with Las Vegas crime boss Johnny Roselli, offering him 150,000 dollars for Castro’s “removal.” Roselli outsourced the job to two of his compatriots across the country— Santo Trafficante in Miami, and Salvatore Giancana in Chicago, a former colleague of Al Capone’s. Both men were on the FBI’s top-10 most wanted list at the time.
Giancana suggested that the most straightforward option was to sneak poison into Castro’s food via a contact he had in the Cuban government. The CIA sent this contact poison pills to sneak into the PM’s food, but, after several unsuccessful attempts, he handed the responsibility off to someone else, who also failed to do the deed. So, the mobsters found a Cuban doctor who worked close to Castro to administer the poison, but, at the last second, the attempt was called off to give way to a new plan.
The infamous Bay of Pigs invasion, orchestrated by the JFK administration, was one of the biggest foreign policy embarrassments in American history. The CIA organized a militia of Cuban exiles and sent them to the Bay of Pigs on Cuba’s southern shore, where they would enter the country, overcome the local military, assassinate Castro, and establish a new government. Except, it didn’t remotely turn out like that. The militia was overwhelmed by Cuban forces led by Castro.
The next few attempts were slightly more subtle, but similar in style, as the CIA found disaffected Cubans, armed them with rifles, and ordered them to shoot Castro. The would-be assassins got close on several occasions, even once getting the Cuban leader in their sights, but the shooter was apprehended before he could fire a shot.
After that, the CIA got much more creative, adopting tactics similar to those used by the mob in the first attempts. The agency sent cigars coated in botulinum toxin, a tasteless and scentless poison that only need touch Castro’s lips to send him to his deathbed. They sent a scuba-diving suit infected with tubercle bacilli and placed an exploding conch in one of his favorite diving locations. They sent him a ballpoint pen that held a hypodermic syringe that would inject Blackleaf 40, a lethal toxin, into the user’s hand. They planted explosives in Cuba’s Ernest Hemingway museum before a planned visit by Castro. Needless to say, none of these worked. The lethal weapons rarely made it anywhere near Castro, as his security detail screened every object to enter his vicinity.
So, the CIA started working with people who had close ties to Castro, including an ex-lover named Marita Lorenz, who was the mother to one of Castro’s children. Her personal connection meant her belongings were less likely to be searched. Lorenz successfully brought a jar of poisoned cold cream into his home, but Castro uncovered the plot before she could get him to use it. According to Lorenz, Castro placed a pistol in her hand and held its barrel against his forehead, daring her to pull the trigger. But she couldn’t do it.
The agency mostly targeted Castro when he traveled abroad. As recently as 2000, near the end of Clinton’s presidency, Castro traveled to Panama for a speech. The CIA contracted a group of Cuban exiles in Panama to place 90 kg of explosives under the podium where he would speak. Castro’s security detail uncovered the plot long before his address and removed all of the explosives. This was the last documented attempt on Castro’s life.
Not all the attempts at removing Castro focused on killing the man, though. The CIA also sought to assassinate his character. For example, Castro’s beard was seen as a symbol of his masculinity and authority. So, the agency planned to pay a shoe shiner to dust his footwear with thallium salts, which would cause the leader’s beard to fall out. They believed this blow could somehow convince the Cuban people that Castro was no longer fit to rule.
Castro was also a potential target for the CIA’s psychedelics program called MKUltra, which we’ve discussed in detail on this channel. The initial purpose of MKUltra was to find a means for mind control. But, after hundreds of tests with LSD, they realized that perhaps the best way to use the psychedelic compound was to drug world leaders, causing them to act strangely in public. So, the CIA arranged a plan to pump a gaseous form of LSD through the ventilation system of a broadcasting booth where Castro recorded weekly radio addresses. The hope was that the drug would cause Castro to say such absurd things that the Cuban people would remove him from power. However, the plot was abandoned when the MKUltra program was shut down.
Despite the constant threat to his life, Castro survived relatively unscathed for his entire run in the Cuban government, as both Prime Minister and President. At one point, the leader claimed, “If surviving assassination attempts were an Olympic event, I would win the gold medal.” He’s probably right. The exact number of assassination plots is unclear, but experts today believe it is at least 600. When Castro passed away in 2016 at the age of 90, it was due to natural causes.
While Castro was the CIA’s most common target, he wasn’t the only man they attempted to assassinate during the Cold War. In most cases, the CIA was a bit more subtle in their attempts, though. Other targets included South Vietnam’s President Ngo Dinh Diem, the Congo’s first Prime Minister, Patrice Lumumba, and Rafael Trujillo, President of the Dominican Republic. In each of these circumstances, the CIA made sure to keep their distance. Sometimes they informed the opposition that they wouldn’t mind if a leader were killed; they also supplied insurrectionists with weapons and plans. However, they never pulled the trigger themselves.
But this begs the question, how did the CIA justify these actions? Well, it’s complicated. Assassination is illegal by definition. It seems that, initially, the plan was to not get caught, and, at first, this worked. It wasn’t until the 1970s that the assassination plots were revealed by the Church Committee, a series of Senate hearings based on declassified CIA files. But, there were no repercussions for the CIA or other American leaders, as they had no explicit knowledge of the attempts to kill Castro or other foreign leaders.
This is because the CIA were experts in plausible deniability. Officials would avoid using words like “assassinate” or “kill” when discussing world leaders. Instead, they would say things like “take care of” or “remove from power,” often leaving their subordinates unclear instructions on how to proceed. In the early Cold War era, these orders were taken to mean “assassinate,” but, technically, no one ever ordered it. Plus, the CIA never personally carried out these executions. By hiring mobsters or Cuban exiles to carry out their plans, they were never directly responsible and could claim the assassins acted independently.
Seeing this problem, President Gerald Ford signed an executive order in 1976 which stated that “No person employed by or acting on behalf of the United States Government shall engage in, or conspire to engage in, assassination.” The order also included a ban on indirect involvement in assassination plots. The United Nations also explicitly prohibited any form of assassination. Yet, despite these laws, certain situations may arise where a president can legally kill a foreign leader.
The first way to do so is for the president to convince Congress to declare war on the target’s country. In times of war, killing people in command or control of the enemy military is considered fair play.
Second, the UN’s rule states that assassination can be lawful if it is done in self-defense. America’s interpretation of this law says that self-defense can be preemptive if there is reason to believe in a potential threat.
Third, the executive action can be interpreted to ban assassinations, but not military actions that may result in a leader’s death. For example, a president can order an attempt to restore a legitimate government or apprehend an international terrorist. If, in doing so, a foreign leader is killed, then it was not a direct order.
Finally, a sitting US president could strike down the executive action and face whatever limited consequences there may be in the United Nations.
Perhaps the most crucial question is whether assassination accomplishes anything. In Castro’s case, the CIA believed that he was personally holding the Cuban government together and that, with his death, the Communist regime there would fall apart. But, from a modern lens, it seems evident that this is rarely the case.
Killing a foreign leader can often lead to even more chaos, destabilizing a country or even an entire region. It reflects poorly on US leadership, especially when American operations overseas are already met with a justifiable degree of mistrust. Perhaps most importantly, assassination is undoubtedly against the American principles of free speech, religion, and association, right?
What do you think? Would killing Castro have solved America’s Cuba problem? Or would it only have led to a new, equally problematic leader and an increase in tension between the countries? Is a government ever justified in assassinating a foreign leader? Can killing a dangerous or brutal politician improve a bad situation? Where is the line between a justified killing of a foreign terrorist and an assassination of a harsh lawmaker? Let us know what you think in the comments, and, as always, thanks for watching.