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Cuban Missile Crisis: Why Cuba Was An Obsession For US Covert Operators

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The question of America’s intentions in Cuba may sound simple, yet the answers are not. The essay will attempt to make the reader understand why America spent decades trying to intervene in Cuba and overthrow the Castro government. Numerous American presidents launched covert operations in Cuba to destabilize the government and failed. Using the available literature on the history of Cuba, the business and industries, the rise of Castro, the Bay of Pigs, and the Cuban Missile Crisis, the essay lists the reasons explaining why American intelligence was obsessed with Cuba.

The first section of the essay is about the role of businessmen and other interest groups that had a monumental stake in Cuba, who worked with the CIA to achieve their goals, and how American business was negatively affected by the reforms undertaken by the Cuban government. The second section of the essay is about the threat of communism spreading in Latin America. The third section is about Castro turning to communism and the Soviet Union. The fourth section is about the Kennedys’ obsession with Cuba relating to the Bay of Pigs and the Cuban missile crisis. The fifth section talks about the counterrevolutionaries.

Business in Cuba

The purpose of the Central Intelligence Agency was to undertake the dirty work of American foreign policy. When the US government decided to topple Castro’s government, this task was handed over to the CIA. The Central Intelligence Agency from inception was well connected to business and corporate interests in America, most of which originated from Texas at that point in time (Mellen, 2016). Various actors in Washington had stake in Cuba, like the US ambassador to Brazil and Peru, who owned a gas company in Havana. He was closely associated with executives working at United Fruit Company, who also had stake in Cuba. To understand the extent of penetration of American businesses in Cuba, this essay explores some figures. President Kennedy once remarked that US companies owned 40% of Cuban sugar lands. American investments in public utilities in Cuba was $316 million in 1956, which comprised 90% of stake in public utilities. American capital controlled 50% of the stake in public service railways in Cuba and American banks had 25% of bank deposits. FDI from America totalled $850 million (Smith, 1960). Fulgencio Batista was the President of Cuba from 1940 to 1945 and 1952 to 1959 during which period he was backed by the US. He represented stability to American interests despite engaging in nationalistic rhetoric and the United States supplied arms and advisors to Batista, especially to crush the rebellion. To secure their business interests in Cuba, it was necessary to maintain internal stability.

Most of Cuba was under the influence of the “Sugar King” and the American market. American-owned industries received nearly 40% of the profit from the sugar industry. Landholding patterns continued from colonial times in rural areas. A minority of the population owned and controlled most of the resources and part of this minority were American citizens. This contributed to a sense of resentment among the Cubans, as many were suffering in extreme poverty. Castro’s ascendance in this environment is not surprising. Castro was not like the typical leaders in Latin America at that time. He built hospitals, hundreds of miles of highways, schools, etc. Large cities in Cuba were cleaned up and Havana was safer than it was a few years before Castro came to power. The particularly problematic part for America was the proposed land reforms, which were not taken seriously at first by American businessmen. In June 1959, it became apparent that Castro was determined to make Cuba lesser and lesser reliant on the United States. In the first wave of reforms, “interventors” were installed by the Cuban government to supervise American-owned companies (Smith, 1960). In October 1958, a meeting was conducted at the State Department regarding the Cuban political situation and consequences for American interests. Some of the people in attendance included representatives from Lone Star Cement, Freeport Sulphur, United Fruit Company, etc. Freeport was working on a $119 million nickel-cobalt project in Cuba. In exchange for overthrowing the Cuban government, they offered to support Nixon in his upcoming election (Escalante, 2004). Corporate interests that were present in a meeting with the FBI in 1958 included King Ranch, The Texas Company, Chase Manhattan Bank, Manati Sugar Company, among many others. This was the extent to which American businesses had penetrated Cuba. They would find unlikely allies in the Mafia, whose large prostitution and gambling rings had come to a halt following the revolution. Certain businessmen who were worried about communism in the Castro movement raised their concerns, but the State Department seemed unperturbed at that point in time. The CIA, however, seemed willing to act against Castro (Mellen, 2016, p. 92). Satellite King Ranches were joint ventures spread out in Latin America and other parts of the world. Robert. J. Kleberg, Jr. was the president of King Ranch, the largest private ranch in America. He was also on friendly terms with the highest levels of authority within the CIA. Becerra in Cuba was the satellite ranch that was the most important in the eyes of Kleberg. When Fidel Castro expropriated Becerra, Kleberg stood to lose all his investment and contacted the CIA to find out what measures were being undertaken (Mellen, 2016, p. 9). Many of the properties Castro confiscated in Cuba were US-owned properties. A segment of the 33,500-acre King Ranch was expropriated and 30,000 acres of United Fruit Company’s land had been “intervened”. It was determined by the State department that American-owned property expropriated was worth $5 to $6 million. Batista was put under trial, to which the Cuban people clamored for justice for his crimes (Smith, 1960).

American businessmen were against the land reform program and communicated their dissatisfaction to the US government. They urged the US government to cut the Cuban sugar quota. The Cuban expropriation program and development of friendly relations with the Communist bloc gave President Eisenhower the justification to cut the sugar quota. The American properties that were confiscated belonged to business interests who had deep connections to the CIA. Freeport Sulphur and United Fruit were names of two such companies. In Washington, the president formed the “Special Group”, which consisted of the Foreign Advisory Intelligence Board and the Forty Committee. This was required for approving covert actions for which the President would be otherwise accountable for. This way, the President would not be held accountable for the illegal actions of the United States. The Special Group was a medium that enabled the CIA to participate in policy-making under an official cover. Kleberg pursued a resolution to finish Castro politically, and in a CIA document, it is revealed that Kleberg and other American businessmen had been willing to fund an assassination attempt of Fidel Castro, his brother and Che Guevara. While this assassination did not take place, it exposed the hand of Kleberg and other corporate interests who supported it such as United Fruit, Lykes Steamship, and Dixie Industries (Mellen, 2016, pp. 128-132). There were also CIA assets in officials working in Pepsi. Part of CIA policy after inception was to achieve certain goals for the benefit of its client corporations. Kleberg and Malone, the vice-president of Czarnikow-Rionda sugar brokerage, became keenly involved in the policy-making of CIA (Mellen, 2016, p. 195). Malone met with Romualdi, the chief agent for labour operations in Latin America, who was leading CIA-managed ‘Free Trade Union of the American Federation of Labour’, which prepared people to challenge communism. It is clear from the opposition from various business interests who possessed influence with the higher level that they lobbied for American intervention to topple the Cuban government so as to further their respective agendas.

Communism in Latin America

According to Robbins (1983, pp. 3-4), Cuban agents were suspected at that time to have instigated revolutions in nearly every Latin American country during the 1960s. The activities included guerrilla operations in Argentina, devising assassination plots in Colombia, transporting arms to Venezuela and provoking student riots in Puerto Rico. Guerrilla training schools based in Cuba produced thousands of Latin American insurgents who went back to their respective countries to lead revolutions. Reagan Administration’s reports detailed the threats Cuba posed to the security of America. According to the reports, Havana was supplying weapons, training and guiding revolutionaries in Nicaragua and El Salvador. It was also believed that Castro’s government was providing guerrilla training and asylum to rebels and terrorists from various countries of Central and South America. A State Department report accused Cuba of organizing a drug-smuggling ring based out of Columbia to ensure finance for the guerrilla activities in these countries. However, these charges were more likely exaggerations due to Washington’s perception of Cuba as a threat. Castro’s government did not possess the military capabilities or the support of allies necessary to conduct a major campaign to launch revolutionaries across Latin America. During the 1970s, various American intelligence analysts came to admit that these charges were exaggerated greatly. During the period between 1961-1969, there was a maximum of 1,500 guerrillas trained in Cuba, which did not match the estimate of 1,500-2,500 guerrillas every year. The threat of such revolutions was manufactured by America for overthrowing Castro’s government and spending millions of dollars to supply weapons to the rest of the hemisphere.

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Castro moves towards communism

America employed various weapons in its arsenal to overthrow Castro from economic and political destabilisation, employing propaganda and even assassination attempts. This is regarded as one of the most large-scale campaigns which was ultimately ineffective. US hostility towards Castro’s government can be explained as a combination of the Monroe Doctrine and the Cold war. According to Robbins (1983, pp. 72-73), one of the reasons US covert operators were obsessed with Cuba was because they were wary of the domestic policies in Cuba, especially the land reform and nationalization of most American companies. This was interpreted as a Communist attack on private property. America could not accept the revolution’s foreign policies and Castro openly adopting Marxist-Leninism and merging with the socialist bloc. As per Robbins, these were the strongest reasons why America viewed Cuba as a threat that must be contained. Further (Robbins, 1983, pp. 92-95), the Soviets sent a trade mission to Cuba only 13 months after Castro in power, signing an agreement in which they would buy 5 million tons of sugar for the next 5 years. This signalled to the American government that Cuba was willing to risk trading with the Soviet despite the tensions with America at that point of time. They also effectively deprived America of possible economic sanctions they could use against Cuba as a weapon. The trade agreement also included sale of crude oil by the Soviet in exchange for Cuban sugar. The American and British refineries notified Castro that they would not refine Soviet oil and were threatened with consequences by Castro. As he warned, he seized these companies. In response, America cut its sugar quota by 700,000 tons and the Soviet Union offered to purchase the sugar. They further deepened their commitment to Cuba by promising Soviet missiles for Cuban defense in case of any future intervention by America. Cuba’s continuous alliance with the Soviet Union was enough evidence to America that it was a threat to American interests. The Cold War climate was taken so seriously that America failed to notice facts that the resources at the disposal of Cuba were limited, there were limited number of guerrillas, and that the Soviet had not actually offered to endorse or sponsor Cuba’s internationalist approach (The National Security Archive, 2001). America was supportive of Cuban independence on the grounds that no foreign navy use its ports and Guantanamo belonged to the US. Prior to the second world war and throughout the period, there was a persistent concern for the straits vulnerable and threatened by German boats and of a Cuba-Germany alignment. Hence, the Soviet Union was keen to further its relationship with Cuba due to its strategic location. It was not solely about nuclear missiles but also the 90 miles distance from the United States, which was a major sea lane. Soviet submarines in this particular area threatened both the straits. It was not Cuba that America was scared of as much as Soviets allying with Cuba and using the opportunity to increase presence in this region (GPF, 2016). In July 1962, the CIA reported abnormal levels of activity in Cuba. There was an influx of Soviet ships onto Cuban shores who appeared to be transporting construction equipment and the unspecified weaponry on an almost-daily basis. The construction seemed to be progressing in several military sites. CIA analysts who assessed the data concluded that Moscow was enhancing Cuba’s air defense system. While America was concerned about the development, it could not protest these defense measures, especially in the light of the then-recent Bay of Pigs fiasco. Meanwhile, Washington received inputs from the Cuban refugee community regarding the construction of nuclear missile sites, which was received with some skepticism as such reports were received for well over a year and a half without any proof. The CIA doubted if these informants could legitimately differentiate between an offensive and defensive missile. It was only in late August when the truth was discovered after Kennedy ordered increased surveillance and photographs were taken that showed surprising activity in San Cristóbal. The Soviets were indeed developing launch sites for medium and long-range missiles and one such missile was discernible from the ground (Robbins, 1983, pp. 105-106). Cuba was effectively the base for Soviet Union’s nuclear missiles and it was dangerously close to American shores.

The Bay of Pigs and the Cuban missile crisis

According to the Church Committee report (Bohning, 2005, p. 3-4), covert action has been defined as an “activity meant to further the sponsoring nation’s foreign policy objectives, and to be concealed in order to permit that nation to plausibly deny responsibility.” The authority for covert option was a command from the National Security Council, NSC 5412/2. The instructions to the CIA were to tackle, minimise and discredit ‘International Communism’ all over the world in a way that was in line with American foreign policies. It was deemed necessary in the cold war era to battle communism with any means necessary. With the emergence of Castro, the communist threat was no longer a battle in a distant land, but from an alarmingly close one to American soil. After the successful regime changes in Iran and at Guatemala, a general feeling of invincibility had swept over the members in the CIA. President Eisenhower sought the help and direction of the CIA to tackle Castro. While there wasn’t enough evidence that Castro was actually a Communist, US officials were convinced that he was steadily under Communist influence. It was in 1960 that President Eisenhower approved an assassination plot to overthrow Castro. This plan came together during the Bay of Pigs, which was a fiasco for the CIA. The Bay of Pigs was a failed military operation of the CIA to invade Cuba. Cuba’s proximity to the United States and the comparably small size showed what a significant victory it was. It seemed that the imperial power of America was collapsing, and even small countries could count on the Soviet Union against imperialism. Castro stated that America could not tolerate that Cubans were undergoing a socialist revolution that they could not control. The Soviets promised the necessary aid required for Cuba during the progress of Bay of Pigs. After the victory of Cuba at Bay of Pigs, the Soviet was able to re-evaluate the balance of forces and could afford to offer more nationalist leaders support if they desired to revolt against the imperialist system. The Kennedy administration reluctantly had to swallow this bitter pill of defeat and humiliation. It was noted in a report ordered by the CIA director, Richard Helms, that the first serious CIA plan to assassinate Fidel Castro included members from the Mafia with contacts in Cuba. The Mafia, with funding from the CIA, was instructed to poison Castro with a pill given to them by the CIA following which, it was passed on to their contacts within Cuba (Bohning, 2005, pp. 25-26).

There are various conflicting accounts of how this was exactly linked to the Bay of Pigs invasion but the effort to topple the Castro government was a build-up to the Bay of Pigs. After the failure of the invasion, President Kennedy publicly accepted blame. In private, he was furious at the CIA, blamed them for the failure and accused the agency of providing him with incomplete information. The agency believed that it was President Kennedy’s actions that were to blame as he did not approve an attack on Cuba’s air force to occur simultaneously with the landing of the commandos. He was also blamed for calling off an airstrike at the last minute. This has been the subject of much debate even today. To understand America’s obsession with Cuba at that period of time, one must be aware of the nature of the Kennedy brothers, particularly Robert Kennedy. From their vantage point, Castro has one up over them and they could not accept the embarrassing outcome. They wanted to exact revenge as it had become shameful for them personally and the desperation drove them to do whatever it takes to oust Castro from power. The aim of the Kennedy brothers was to harass Castro in any way possible. Only six months after that, a multiagency covert action programme for subversion was formulated by the Kennedy administration called Operation Mongoose. Unlike Bay of Pigs, it was a small-level covert operation of economic sabotage, infiltration and propaganda. While it wasn’t the final plan itself, the goal was to contribute to the breakdown of the Castro government. Robert Kennedy took control over this small-time covert operation and the atmosphere in the White House left little doubt for compromise in ensuring Castro would not remain in the neighbourhood for long. He grew more and more restless due to the lack of significant progress in developing a concrete plan (Bohning, 2005, pp. 69-79). Meanwhile, missiles were being transported to Cuba discreetly under Moscow’s project Operation Anadyr. The increased threat of a US invasion of Cuba required Cuba and Soviet to work together to redress the nuclear missile imbalance. This operation lasted went on for a year till the missile crisis and accomplished nothing substantial for the amount of $50 million in expenditure. Bohning (2005, p. 150) states that the missile crisis was settled by January 1963. However, Kennedy was still determined to overthrow Castro. Months after approving a focused “sabotage and harassment” program, he was assassinated. In handling Cuba, Kennedy would be remembered for his inexperience that led to disastrous consequences which almost triggered a nuclear war.

After the Bay of Pigs, Castro was convinced that the Americans were going to try to invade again. Fearful that he may be overthrown, Castro accepted the offer from Khrushchev to bolster his country with nuclear missiles. The Cuban missile crisis was one of the most dangerous situations the world had experienced. As Cuba gravitated further towards communism, the Soviet missiles were transported into Cuba. It was not anticipated by either Khrushchev or Castro that placing missiles in Cuba would lead to a nuclear war, although they did consider that America would attempt to invade the country. With the Soviet standing firm in its commitment to Cuba’s defense, America was forced to act. President Kennedy decided to place a naval quarantine on Cuba to block off any further shipments. America and Soviet Union came close to nuclear war after increased tension in exchanges. After negotiations, Khrushchev decided to withdraw the missiles placed in Cuba back to the Soviet Union. The Cuban missile crisis deeply affected both Kennedy and Khrushchev. There was an unshakable fear of the dangers of the Cold War after a situation they had both misjudged, and a greater agreement on the need to reduce the probability that the arms race could lead to nuclear conflict. While Castro was displeased with the withdrawal of the Soviets, America was forced to publicly state that it would not engage in military intervention in Cuba.


Hundreds of middle-class Cubans, with the politicians who moved to their country in search of former jobs they lost in the revolution, migrated to the United States. There, they unleashed a propaganda campaign condemning communism in Cuba. The goal was to create counterrevolutionaries who could destabilise the Cuban government in the future, one the CIA was fully behind (Escalante, 2004, pp. 36-37). These Cubans lived in the Florida region and there was constant communication with the CIA and they acted as informants. The counterrevolutionaries in Cuba engaged in criminal behaviour to manufacture a chaotic atmosphere similar to a civil war so that America could justify military intervention. Counterrevolutionary leaders coordinated with the CIA regarding arms supply and other support. The CIA began to create disturbances in the region. Air and sea movements between Costa Rica, Nicaragua, Guatemala and Florida were frequent. Soon, American and Cuban people began to trade illegal weapons in the guise of fight for liberty. This would be eventually replaced with drug trade. Escalante (2004, p. 59) states that the CIA and their partners were at the forefront of the drug trade, transporting thousands of tons of marijuana, cocaine, and other drugs. He also states that the US Central Intelligence Agency officials enriched themselves through drug trade in the process of overthrowing the Cuban government.


The reasons as to why US covert operations were obsessed with Cuba are many. The American business interests clearly had a huge role to play in various covert operations. The scope of the CIA is not limited but evidently involves protecting interests well beyond the traditional realm of intelligence and operations detail. The spread of communism in Latin America in the form of revolutions has been a fear for America, which has been apprehensive of communism so close to its shores. Since parts of Latin America were underdeveloped, it made them more susceptible to communism and America was fearful that it would spread with Castro’s influence. Castro’s conversion to communism and movement to the Soviet bloc was worrisome for America, as any Soviet presence in Cuba was unacceptable to America’s security. The fiasco at the Bay of Pigs was a huge embarrassment for Kennedy, who privately blamed the CIA. Robert Kennedy and President Kennedy were determined and obsessed to oust Castro so much that they launched Operation Mongoose, which didn’t achieve anything significant. The Missile Crisis was a moment in history when America was confronted with nuclear war so close to sovereign territory. Kennedy vowed to continue to harass the Cuban government in spite of publicly stating that America would not intervene in Cuba any longer. America is an imperial power that was losing grip on the countries that it could once control without question. Cuba was a country that challenged America’s imperial ambitions and America used every justification to quell the rise of Castro. These are some of the reasons why American covert operators were obsessed with Cuba.

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