U.S. Covert Activities Against Cuba

The Untold Tale of Secret Foreign Policy

by | May 15, 2005

Street protest, 1959. Photo by Ernesto Fernandez

Less than a year after Fidel Castro seized power in Cuba on January 1, 1959, the United States concluded that co-existence between Washington and Havana would be impossible. This conclusion led to six years of futile covert programs under three different American presidents to depose Castro. U.S. efforts included every arrow in the covert quiver, from organizing and supporting a proxy exile invasion to economic and political destabilization, from sabotage and propaganda to psychological warfare and assassination plots.

It is now painfully obvious that the myriad U. S. covert activities directed at Cuba more than four decades ago failed miserably. Not only did they fail to oust the Cuban leader, but instead triggered the Law of Unintended Consequences, consolidating and prolonging Castro’s rule and contributing to a Soviet decision to install nuclear missiles in Cuba. Simultaneously, they transformed South Florida into a hub of anti-Castro ferment and upheaval, making it the frontline in the attempts to end his rule.

The U.S. public—if it was aware at all—saw only the tip of the covert iceberg. The broad outlines emerged slowly and piecemeal in newspapers, magazines and books over the ensuing decades. Only in recent years has the scope of the U.S. government’s secret war against Castro become apparent—abetted by the declassification of thousands of once secret documents and increased willingness of surviving participants to talk with the passage of time.

Essentially, this covert war can be broken down into three phases, beginning under President Eisenhower, continuing under President Kennedy and ending under President Johnson. Each of the three phases included Castro assassination plots, but none came close to succeeding. The debate continues today as to whether Eisenhower, Kennedy or Johnson was even aware of them.

The first phase began in late 1959 with the accelerating deterioration in Washington- Havana relations. By October, U.S. officials were convinced that if Castro wasn’t a Communist, he was under Communist influence and had to go.

In January 1960, a Cuban task force within the CIA was formed to undertake the effort. Jake Esterline, a guerrilla warfare veteran with the OSS in Burma during World War II and prominent in the CIA’s 1954 overthrow of Jacobo Arbenz, Guatemala’s left-leaning president, was selected to lead it. Two months later, March 17, 1960, President Eisenhower approved a covert action plan to remove Castro. After a change in administrations from Eisenhower to Kennedy—and with many permutations in the original concept—the first phase culminated with the disastrous April 1961 Bay of Pigs invasion by a U.S. trained and supported Cuban exile brigade.

Esterline originally designed the plan to train and infiltrate several hundred guerrillas into the Trinidad area in the middle of the island’s south coast to join with anti-Castro insurgents already active in the Escambray Mountains of central Cuba. But Richard Bissell, then head of the CIA’s clandestine services, had other ideas and the plan evolved from a guerrilla infiltration to an exile invasion. The hopes was that the invasion would spark an internal revolt or, at the least, seizure of a beachhead where a provisional government could be established which could appeal for international help. In September 1960, Jack Hawkins, a Marine colonel with amphibious landing experience, was brought in as the project’s paramilitary chief.

Kennedy succeeded Eisenhower in January 1961, raising uncertainties about the future of the project, but Kennedy eventually gave his approval. However, in mid-March, he ordered the exile brigade’s landing site changed from Trinidad to a “less noisy” locale, in the hopes of keeping U.S. government’s fingerprints off the action. The isolated Bay of Pigs, 80 miles west of Trinidad, was the new choice, providing the criteria Kennedy demanded to maintain “plausible deniability” of U.S. involvement. Still, on Sunday, April 16, 1961, the eve of the invasion and under pressure from Secretary of State Dean Rusk, Kennedy ordered the last minute cancellation of already approved D-Day air strikes intended to take out the remnants of Cuba’s ragtag air force.

Esterline and Hawkins made it clear in interviews that they believe the belated change in landing site and cancellation of the D-Day air strikes doomed the invasion. They held Kennedy and Rusk responsible. However, as once-classified documents emerged, Esterline and Hawkins added Bissell to the blame list, accusing him of withholding vital information both from them and from President Kennedy, so convinced was Bissell by his own arrogance that the invasion could not fail.

As Esterline declared at a 1996 Bay of Pigs conference: “I don’t think he [Bissell] was being honest up…with Kennedy and maybe with [Allen] Dulles, too; and I don’t think he was being honest down in dealing with his two principal aides, Esterline and Hawkins. I don’t believe he was leveling with any of us.” This sentiment was further reinforced later when the two aides learned for the first time that Bissell had agreed with a Kennedy request only days before the invasion to cut back on air support but did not tell them of the decision.

In a significant incident largely overlooked by historians, Esterline and Hawkins met for three hours with Bissell at his home in the Cleveland Park section of Washington on Sunday morning, April 9, eight days before the invasion brigade’s landing at the Bay of Pigs. They told Bissell that the change in landing site and other limitations put on the project by the Kennedy administration made it impossible to succeed. They recommended he call off the invasion saying would resign if he did not.

Bissell beseeched them to stay. He argued that the project would go ahead anyway but had a better chance to succeed with them on board. They agreed, extracting a pledge from Bissell that the promised air support they felt needed for success would be forthcoming. Yet, after their Sunday meeting, Bissell agreed to cut it back, despite his pledge to Esterline and Hawkins. They did not learn that until reading declassified documents 34 years later.

The invasion debacle led to the second phase, this time with the active participation of Robert F. “Bobby” Kennedy, the president’s brother and attorney general, who previously had played no role in either Cuba policy. In an April 19, 1961, memo to the President the day the invasion collapsed, he urged a renewed campaign against Castro. Another Cuba task force was formed—headed by White House aide Richard Goodwin—to draft a new covert program. President Kennedy approved it in November 1961. Codenamed Operation Mongoose, it brought together all the relevant government agencies under a single umbrella.

Reflecting the distrust of both Kennedy brothers of the CIA following the Bay of Pigs, President Kennedy named Brig. General Edward Lansdale, a flamboyant and eccentric officer with a reputation gained earlier in the Philippines as a counter-insurgency expert. But everybody involved knew Bobby Kennedy was the real Mongoose czar, making sure Cuba became the Kennedy administration’s highest priority.

The overall objective of Mongoose, in Lansdale’s words, was “to bring about the revolt of the Cuban people [that] will overthrow the Communist regime and institute a new government with which the United States can live.” Under Lansdale’s programmed timetable for Mongoose, Castro’s fall would come the following October, coincidentally just a month before U.S. Congressional elections. Mongoose effectively ended in November 1962, not with the revolt Lansdale had scheduled, but with the Cuban Missile Crisis, a crisis Mongoose helped provoke by signaling Moscow and Havana that a new Cuba invasion was likely.

Even without the missile crisis, it appears that Mongoose eventually would have floundered to an unmourned end. It failed to achieve even minimal expectations, except for intelligence gathering. Many of its participants, institutional and individual, had little enthusiasm for Mongoose. There was, as well, a general antipathy among them for Lansdale and Bobby Kennedy, its two leaders and principal proponents.

By the beginning of 1963, Mongoose was officially dead. The missile crisis had been resolved. The remaining Bay of Pigs prisoners returned to the United States in exchange for a $53 million ransom of food and medicines. The time had come for the Kennedy administration to again revamp its Cuba policy, but one now constrained by Kennedy’s no-invasion pledge given Moscow in return for the missile withdrawal.

So began phase three of the covert war, this time with the State Department in the coordinating role.President Kennedy made clear that “an assurance covering invasion does not ban covert actions or economic blockade or tie our hands completely. We can’t give the impression that Castro is home free.”

A cornerstone of the new Cuba policy, as suggested earlier by Ed Martin, the assistant secretary of State for inter-American affairs, was to be a “program of ‘giving Cubans their heads’ in an effort to affect the downfall [of Castro] from within.”

Although not officially approved by President Kennedy until June 1963, the new covert program was well underway by early 1963, its rough outlines sketched by Bobby Kennedy to invasion brigade leaders Manuel Artime and Erneido Oliva at his Hickory Hill, Virginia residence within a month after their release from Cuban prisoners. As one component of the new effort, the CIA would continue to externally mounted sabotage raids against Cuba, but the greater focus was to be on two so-called “autonomous groups” of Cuban exiles, one headed by Artime and the other by Manolo Ray. Both were to receive CIA logistical and financial, but not tactical, assistance.

The autonomous program remains among the least known, least understood, most creative and most controversial of all the U.S. covert activities targeting Cuba. At the same time President Kennedy named Oliva, the second in command and a hero of the invasion brigade, as the official representative of all Cubans in the U.S. military, with the idea clearly being that he would work in tandem with Artime.

Ray, an early cabinet minister under Castro and favorite of the Kennedy White House, but a man who many Cuban exiles regarded negatively as a proponent of Fidelismo sin Fidel—Castroism without Castro— had been a late addition to the Cuban Revolutionary Council, the exile group organized by the CIA to front for the Bay of Pigs invasion. Artime, already a member of the Council, was its representative to the Bay of Pigs Brigade and was captured at the time of the invasion.

The “rules of engagement” for the Ray and Artime autonomous groups specified that all their operations would be “mounted outside the territory of the United States” and that the “United States presence and direct participation in the operation would be kept to an absolute minimum.”

Sam Halpern, a CIA official involved in Cuban covert activities at the time, put it most succinctly as the program got underway. “The next thing we knew,” said Halpern, “the word was, ‘let Cubans be Cubans.’ Let the Cubans do their own thing. But the Cubans didn’t have any money. So the CIA’s got money. Give ‘em money. We gave them money. We told ‘em where to by arms, ammunition. We didn’t give it to ‘em. They went out and bought their own. They decided what they wanted. They picked their own targets, then told us what the targets were. We provided them intelligence support…and we didn’t have anything to do with what they were up to. They just told us what they were going to do and we said ‘fine. We’re not stopping you.’ And we didn’t.”

Artime set up camps in Costa Rica and Nicaragua, with full knowledge of both Central American governments and Washington. After more than a year of preparation, his commandos carried out their first raid May 13, 1964, against a sugar mill in Cuba’s Oriente Province. By then, President Kennedy had been assassinated, Lyndon Johnson was president and, with both the war in Vietnam heating up and Johnson’s personal antipathy towards Bobby Kennedy, enthusiasm for the secret war against Cuba had begun to wane. The death knell sounded in September 1964 when the Artime group fired on a Spanish ship en route to Havana, mistakenly thinking it was a Cuban freighter leaving Havana with a rice shipment to Japan. Several Spanish crewmen were killed. A major diplomatic row ensued.

Ray, who claimed to have a major underground network in Cuba which he intended to exploit, accomplished even less, continuing to operate from Florida and Puerto Rico, despite pressure for him to move his operations outside U.S. territory. He set up a base in the Dominican Republic in late 1964, but did nothing, although declassified documents show him receiving a monthly subsidy of $10,000.

By late spring 1965, U.S. funded and supported covert actions—apart from intelligence gathering and propaganda—ended. The CIA’s new director, Adm. William Raborn, made an abortive effort to resurrect the covert program in a June 26, 1965, memo to President Johnson. It went nowhere. The only thing left was cleaning up the residue of six futile years aimed at ousting Fidel.

Spring/Summer 2005, Volume IV, Number 2

Don Bohning is the author of a new book entitled The Castro Obsession: US Covert Activities Against Cuba, 1959- 1965. This essay is based on his book, published this spring by Potomac Books (formerly Brassey’s, Inc.) of Dulles, Virginia. Longtime Latin America editor for The Miami Herald, Bohning covered Cuba, Haiti and the rest of Latin America for many years.

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