The Kennedy Men

by Laurence Leamer

  These CIA leaders were for the most part sophisticated men who were not terrified by words like “socialist” and “social democrat,” so-called progressives who seemed to want the same world that the president wanted. One of the president’s favorites, and his putative choice to become the next director when sixty-seven-year-old Dulles retired, was Richard Bissell, the CIA director of covert operations. An economist, Bissell was an accomplished man who had come into government during the New Deal as a protégé of the liberal Chester Bowles in the Office of Price Administration. Fifty-year-old Bissell had developed the U-2 program, which, until the Russians shot down Francis Gary Powers in 1960, had been indispensable in getting accurate information about Soviet defenses and missile sites.

  Dulles described a Cuba that had become “for practical purposes a Communist-controlled state” in which there was “a rapid and continuing buildup of Castro’s military power, and a great increase also in popular opposition to his regime.” For months the United States had underwritten a series of covert actions, including sabotage, infiltration, and propaganda, while training an insurgent guerrilla force in Guatemala. Most of this Kennedy already knew before the election, and he had learned the rest immediately afterward when Dulles briefed him.

  The tweedy, pipe-smoking CIA head explained that there was a renewed urgency to these efforts. The Soviet Union was shipping tons of munitions to the island. Cuban pilots had gone off to Czechoslovakia to train. Castro was steadily garroting his people’s liberties until soon the populace might hardly have the strength to rise up, and his agents were provoking revolution throughout Latin America. As the agency realized the magnitude of the challenge, the program of covert actions kept expanding: from the original $4.4 million the year before Kennedy took office, the budget for fiscal year 1960/61 grew to more than $45 million.

  Kennedy had met with Eisenhower on the day before the inauguration, when the Republican president had bequeathed his covert Cuba program and admonished his successor to push on with the plans. These were no longer guerrilla infiltrations that Dulles was proposing to the new president, however, but a major amphibious invasion seeking to establish an impregnable enclave that would set off an uprising across Cuba, or at least be a symbol of resistance that would grow until finally the whole island was rid of Castro and his Marxist regime. The Republican president had never authorized an invasion that might involve American troops. Kennedy was being asked to authorize a far more dangerous venture than the one that Eisenhower had signed on to, and far beyond anything the Republican president had authorized the CIA to attempt during his two terms in the White House. The CIA was hoping that its paramilitary force and its agents on the island would foment a “continuing civil war,” setting brother against brother in the streets and fields of Cuba, a struggle in which the United States or its Latin surrogates could then intervene and play savior.

  On January 4, 1961, before Kennedy was inaugurated, Colonel Jack Hawkins, the head of the CIA’s paramilitary staff, prepared a crucial memo outlining what the United States would have to do for the operation to be successful. Hawkins was a poster-handsome marine officer who had fought on Iwo Jima and at the Yalu River in the Korean War and was on the fast track to become a general. Hawkins knew little about Cuba or intelligence and was depending on what the agency told him about Cuban realities. “My belief from the intelligence provided by the CIA was that the place was ripe for revolt,” said Colonel Hawkins. “As it turned out, the CIA intelligence was hugely wrong, based largely on Cuban émigrés in Miami saying things that would promote their cause.”

  Hawkins’s CIA plan called for the brigade to liberate a small area, then to dig in, waiting for “a general uprising against the Castro regime or overt military intervention by United States forces.” If the Cubans did not rise up against Castro, a provisional government would be established on the small territory and “the way [would] then be paved for United States military intervention aimed at pacification of Cuba.”

  At the first Special Group meeting on Cuba, held Sunday morning, January 22, two days after the inauguration, Dulles told a number of Kennedy men, including the attorney general, that he thought “our presently planned Cuban force could probably hold a beachhead long enough for us to recognize a provisional government and aid that government openly.” A few days later, at another meeting on Cuba, General Lyman L. Lemnitzer, the chairman of the Joint Chiefs of Staff, said that he felt that the envisioned force of six hundred to eight hundred was inadequate, and he anticipated that “final planning will have to include agreed plans for providing additional support for the Cuban force—presumably such support to be the U.S.”

  As Kennedy listened to the arguments and perused the memos that passed across his desk, trying to decide what to do, he was so new in the Oval Office that he told Ormsby-Gore, the British ambassador, “You don’t even know which of your team you can really trust from the point of view of their judgment.” He knew this was an important decision, but neither he nor anyone else had any idea that his actions here would be one of the defining moments of his administration. His decisions would lead him up the pathway to nuclear confrontation with the Soviet Union. His judgments would dramatically affect administration polices from Bolivia to Vietnam and help create fiercely held attitudes that would determine American policy toward Cuba until the end of the century and beyond. His decisions in early 1961 may even have inspired an assassin who would be waiting to meet the president on the saddest of November days.

  What Kennedy could not have known as he attempted to make the first crucial decision in his administration was that so much that mattered was not only left unsaid but also probably unthought, unfelt, and unseen. Spanish was hardly an esoteric language, but crucial CIA officials in Miami spoke only a few words of the language and knew nothing about Latin American culture or politics. “They were a strange bunch of people with German experience, Arabic experience, and … most of them had no knowledge of Spanish … and absolutely no sense or feel about the political sensitivities of these people,” recalled Robert Amory Jr., then the CIA’s intelligence chief, the top official concerned with gathering and evaluating information. “I think we could have had an A team instead of being a C-minus team.”

  The CIA team exemplified the cultural arrogance that for decades Latins had considered the mark of the gringo. It was the same kind of parochial superiority that had rankled Kennedy when he saw it among American diplomats when he traveled through Asia in 1951. Among the officers working most directly with the brigade were men who felt superior to their Latin associates, whose character they knew only through ethnic stereotype, but there were others who bonded with their Cuban charges and respected their courage and patriotism.

  The CIA operatives in Miami put together the Frente Revolucíonario Democratico (FRD) to provide the illusion of a united anti-Castro front, and then a five-man Cuban Revolutionary Council (CRC) to provide the makings of the provisional government of a new Cuba. These Cuban leaders were nonetheless considered so indiscreet by their handlers that when the time of the invasion arrived, the plan was to put them under de facto house arrest. Yet these same men were supposed to be seen by their people, not as the tainted creatures of the CIA, but as worthy independent leaders of a new Cuba.

  Kennedy probably did not know that so many of the initial attempts at sabotage, infiltration, and paramilitary airdrops had failed. Out of the sixty-nine thousand pounds of arms, ammunition, and equipment dropped to operatives on the island, between December 30, 1960, and April 21, 1961, forty-six thousand pounds ended up in the hands of Castro’s forces. These errors were attributed to the incompetent Cuban exile pilots, never to the strength of the pro-Castro Cubans.

  The agency believed in March 1961 that the “hard core” of Castro adherents on the island of 7 million people consisted of “not more than 5,000 to 8,000 [who] would fight to the end for Castro,” while there were supposedly 2,500 to 3,000 anti-Communist guerrillas and insurgents whose numbers would gr
ow “at least ten times that size once a landing is effected.” A month later the CIA’s figure had grown to “nearly 7,000 insurgents” actively fighting Castro.

  The figures were little better than the wishful fantasies of operatives blinded by their mission. The CIA had other more realistic analyses of Cuba, but they did not reach Kennedy’s desk. CIA Director Allen Dulles kept the agency’s own intelligence chief and his operation out of the loop. “I was never in on any of the consultations, either inside the agency or otherwise,” Amory recalled. Although this was supposedly done for security reasons, Dulles and Bissell apparently did not want a more detached assessment on Cuba reaching the president.

  Castro’s government was something more than a tyranny imposed on a hapless people. The upper class had left the island, much of the middle class was leaving, and Castro was promising schooling to those who had none, cheap medicine to those who went without, and work for those who sat idle. These Cubans had somber memories of Batista’s regime, during which time Americans had owned almost all of the country’s mines, most of its utilities, and close to half of its sugar industry. When Castro appropriated foreign properties, those Cubans left on the island for the most part thought it little more than the righteous return of their property. Nor did the one hundred thousand tenant farmers and squatters who had been given land pine for the return of their landlords.

  When the CIA’s operatives set fire to three hundred thousand tons of sugar cane, forty-two tobacco warehouses, two dairies, four stores, and a sugar refinery, then bombed the Havana power station, a railroad terminal, a railroad train, and a bus station, they not only made many pro-Castro Cubans firmer in their resolve but also gave Castro further justification for his steady intrusions on Cuban liberties. Castro’s opponents were growing in force too, as citizens of the Caribbean island saw the inevitable totalitarian trajectory of the regime. But if an invasion came, there were still likely to be hundreds of thousands of peasants, workers, students, and others who believed in Castro and would defend their country with fierce determination.

  In a March NSC meeting, Kennedy asked that the United States push the Organization of American States to call for “prompt free elections in Cuba, with appropriate safeguards and opportunity for all patriotic Cubans.” Four days later, Schlesinger wrote the president that the State Department had decided “the risk is too great that Castro might accept the challenge, stage ostensibly free elections, win by a large majority and thereafter claim popular sanction for his regime.”

  As loath as many in the CIA were to admit it, Castro was an authentic revolutionary who inspired millions not only in his own land but also in the barrios of Mexico City, the wretched slums of Lima, and elsewhere across Latin America. So this enterprise that the CIA was planning would be seen in much of the world not as liberation but as invasion.

  Kennedy realized that “Castro has been able to develop a great and striking personality throughout Latin America and this gives him a great advantage.” The president also saw that it was only a matter of time before all but the politically blind would see that Castro was a determined Marxist who employed subversion, conspiracy, and state-sanctioned murder, all in the name of people’s revolution, and that the Cuban people would pay a terrible price for the illusion of equality. Kennedy had seen in Asia how communism grew best in poverty and tyranny, and the new administration would promise an Alliance for Progress for Latin America to help create a climate in which progressive democratic regimes could grow. At the same time, with the new administration’s knowledge, the CIA continued to appropriate the weapons and means of its totalitarian enemies and was using them with willful determination.

  Truth is the ultimate weapon in a democracy, but truth does not work as quickly as deception. On CIA-sponsored Radio Swan, truth became only an occasional visitor on the broadcasts to Cuba, elbowed aside for propaganda blown up into gigantic cartoons. In its planning for the invasion, the CIA intended “to intimidate so as to obtain local support,” subverting the will of the Cuban people much as Castro did.

  While in the White House, the president and his foreign policy advisers discussed the proposed Cuban operation, the CIA went ahead with its own deadly scheme to try to assassinate Castro. Bissell, the mastermind of these plots, told the historian Michael Beschloss: “Assassination was intended to reinforce the plan. There was the thought that Castro would be dead before the landing.”

  The best known of the many schemes to murder Castro involved employing Mafia figures with Cuban connections to orchestrate the deed. The intelligence community had a long-term relationship with American mobsters going back to World War II and continuing in some measure in the postwar years. In late August 1960, during the last months of the Eisenhower administration, Bissell had asked Sheffield Edwards, the CIA director of security, to contact people with gambling interests in Havana, who by implication might be interested in murdering Castro. Edwards then asked Robert Maheu, a former FBI agent associated with Howard Hughes, if he had any contacts. When Maheu introduced James P. O’Connell to John Rosselli in mid-September, the mobster immediately guessed that O’Connell represented the CIA. Rosselli then introduced the CIA agent to other Mafia figures.

  These agents were in Miami in early 1961, meeting with their collaborators Sam Giancana and Santos Trafficante, when they supposedly came upon the mobsters’ pictures in Parade, the Sunday newspaper supplement, on the Justice Department’s list of the ten most wanted gangsters. This newfound knowledge affected the CIA not at all. As for these mobsters, they had discovered a newfound patriotism, for the death of Castro would mean that they could return to Havana and rule once again over the hotels, casinos, brothels, and drug rings. That, to these gangsters, was what freedom was all about. In Florida, Rosselli was working to give botulinumtoxin pills from the CIA to Juan Cordova Orta, a Cuban close to Castro and willing to poison the leader. Trafficante was attempting to do much the same.

  The CIA-Mafia plots were so much the stuff of pop novels and cinematic fantasies that they have largely crowded out awareness that the agency made many other kinds of serious attempts to kill Castro. The non-Mafia-associated assassination attempts in the early months of 1961 included those led by Felix Rodriguez, a Cuban exile and CIA operative, who wrote in his memoirs that his teams twice tried unsuccessfully to infiltrate Cuba by ship. John Henry Stephens, another official, testified to Congress that he had led five-man teams of “Poles, Germans, and Americans” in failed attempts against Castro. On March 29, 1961, a cable arrived at CIA headquarters from an operative code-named “NOTLOX”: “(Plan [for] 9 April): Fidel will talk at the Palace. Assassination attempt at said palace followed by a general shutting off of main electric in Havana.” Raphael Quintero, a prominent Cuban exile leader, recalled: “I was part of that [NOTLOX] plot. There was going to be a big boxing match and we knew Castro was supposed to be present. We planned to have him hit with a bazooka.” The CIA asked Quintero’s group to back off, apparently giving the go-ahead to another group of exiles who were unable to pull the assassination off a few days before the planned invasion of Cuba by an exile brigade.

  The men who loved Kennedy and revere his memory most deeply are convinced that the president knew nothing about the assassination plans. They recall how repulsed the president appeared whenever such talk was even broached. Kennedy, however, was a man of many faces and possessed of knowledge far beyond that of any one of those who served him, and his denials, as passionate as they may have been, are by no means definitive. Deniability was the CIA’s god. There would be no paper trail, no bureaucratic witnesses, probably not even much detail, perhaps just a nodding suggestion so vague that the president could claim that he had not heard.

  The deadly language of euphemism hung in the air. Sometimes words meant more than they seemed to mean. Other times they meant less. On still other occasions, they meant nothing at all. When some in the CIA talked of “disposing of Castro,” they meant ending the Communist regime. When others discussed “doing
something about Castro,” they meant murdering him. In the end, these clandestine men spread a fog so thick that it was impossible to tell definitively who knew and who didn’t know about their acts, or even just when their murderous attempts began and when they ended.

  When Bissell and his subordinates talked about murder, the 1967 CIA Inspector General’s Report on the assassination attempts noted that “the details were deliberately blurred and the specific intended result was never stated in unmistakable language.” There was, in the report’s telling phrase, “the pointed avoidance of ‘bad words.’” These were deadly serious men, but they did not want to be caught speaking such murderous words as “poison,” “shoot,” or “garrote.”

  In February 1961, Bissell called into his office William Harvey, a top clandestine CIA officer, to discuss “executive action capability,” bureaucratic language for assassination. “The White House has twice urged me to create such a capability,” Harvey remembered the CIA covert director saying.

  A decade and a half after these first assassination attempts had ended, Senator Charles Mathias was among those sorting through the charred remains of the policy. “Let me draw an example from history,” the Maryland senator said. Then he recalled how Henry II, the twelfth-century British monarch, had grown angry with Thomas Becket, the archbishop of Canterbury. “Who will free me from this turbulent priest?” the king asked, and four of his knights traveled to the cathedral at Canterbury to strike down Becket at the altar.