Modern history



Less than forty-eight hours after narrowly winning the presidency on November 8, 1960, John F. Kennedy emerged from his waterfront home in Hyannis Port, Massachusetts, to meet reporters. More than a hundred had descended on the little village, and the only place big enough to hold them all was the National Guard armory. They waited on folding chairs to hear what the president-elect would say.

Kennedy won the election in part because of his image of dynamic vigor, and he used this press conference to announce that he had already chosen key members of his new team. One reporter wrote that he reeled off names “in rapid-fire succession.” The first one was familiar.

“I have asked Mr. Allen Dulles to stay on as director of central intelligence, and he has acceded to that request,” Kennedy said. “He has served every president since Wilson, in a variety of capacities, and a continuity of stability and direction in this particular post is imperative.”

Allen’s decision to accept reappointment would decisively reshape his place in history. He had emerged from eight years as Eisenhower’s spymaster with a powerful reputation. His triumphs were widely rumored, his failures little known, and his lack of interest in managing the sprawling CIA apparent only to Washington insiders. To all appearances he was both a brilliantly successful intelligence officer and an honorable gentleman. Had he retired at this point, he might have basked in admiration for the rest of his life.

Clover urged him to step down. In the end, though, he could not bring himself to leave the life he loved. There was still more to do. He wanted to be in office to dedicate the new CIA headquarters at Langley. His Laos station was opening a new front in the war against Ho Chi Minh. Most important, he was plotting to bring down another “monster.”

Allen had just helped crush Lumumba, but could not consider it a true CIA victory because Belgian agents had struck the decisive blow. His operations in Tibet and Laos were faltering. Eager for a decisive triumph, he went forth against Fidel Castro, the young radical who had seized power in Cuba.

Castro’s rise had set off a surge of controlled panic in Washington. Eisenhower had directed Allen to design a plan for covert action against him. Rather than produce one, Allen did something entirely new. He turned the operation over to a subordinate and withdrew into a private cocoon. As the CIA planned this far-reaching and highly complex operation, its director was almost entirely detached. He never focused on the plot. At times he even seemed to disassociate himself from it, as if it were none of his business. By sleepwalking through this history, Allen helped guide the United States to a devastating defeat that forever tarnished his legacy.

* * *

Cuba holds a unique place in the American imagination. It lies so close to the United States and offers such rich resources and strategic advantage that it long seemed a natural candidate for annexation to the United States. Presidents since Thomas Jefferson have coveted it.

“I candidly confess that I have ever looked on Cuba as the most interesting addition which could ever be made to our system of States,” Jefferson wrote. “The control which, with Florida, this island would give us over the Gulf of Mexico, and the countries and isthmus bordering on it, as well as all those whose waters flow into it, would fill up the measure of our political well-being.”

In 1898 President William McKinley sent American troops to Cuba to help rebels overthrow Spanish rule. They succeeded. Immediately afterward, the United States Congress voted to renege on its pledge, enshrined in law as the Teller Amendment, to withdraw the troops after victory and respect Cuban independence. McKinley named an American military governor. Later the United States granted Cuba limited self-rule but landed troops whenever American interests seemed threatened. That happened in 1906, 1912, and 1917—when Secretary of State Robert Lansing dispatched an occupation force at the suggestion of his nephew John Foster Dulles, whose Sullivan & Cromwell clients wished to ensure the continuance in power of a regime that respected their investments.

For much of the twentieth century Cuba remained a quasi-colony of the United States. During the 1950s, the last of its pliant dictators, Fulgencio Batista, struck lucrative deals with American gangsters, who built lavish hotels and casinos, filled them with American tourists, and turned Havana into the most garishly sinful city in the hemisphere. American businesses, including Sullivan & Cromwell clients, dominated the country. They owned most of its sugar plantations—two of the largest belonged to United Fruit—and were heavily invested in oil, railroads, utilities, mining, and cattle ranching. Eighty percent of Cuban imports came from the United States. When International Telephone & Telegraph asked Batista to approve a steep rate hike in 1957, Foster sent a message advising him that the increase would serve “the interests of Cuba.” Batista approved it. In a vivid display of gratitude—the scene became a centerpiece of the film The Godfather, Part II—executives from ITT presented him with a golden telephone.

Although most Americans could not or would not see it, Cuba’s corrupt tyranny was increasingly unpopular. During 1958 Castro’s guerrillas won a series of victories. On the last day of the year, Batista resigned. Before dawn on January 1, 1959, he fled to the Dominican Republic, taking several hundred million dollars with him. A week later, after a jubilant trip across the island, Castro arrived in Havana and began a political career that would shape world history.

Foster was convalescing in nearby Jamaica when Castro seized power. “I don’t know whether this is good or bad for us,” he mused after hearing the news.

Three months later Castro made his tumultuous trip to the United States. The nascent counterculture embraced him. Allen Ginsberg and Malcolm X came to his hotel in Harlem. Supporters cheered outside. One carried a sign reading MAN, LIKE US CATS DIG FIDEL THE MOST—HE KNOWS WHAT’S HIP AND WHAT BUGS THE SQUARES.

After returning home, Castro gave a speech scorning Vice President Nixon, the highest-ranking American he met, as “an impenitent disciple of the gloomy and obstinate Foster Dulles.” Soon afterward he confiscated hundreds of millions of dollars in American investments, grievously wounding Sullivan & Cromwell clients as well as gangsters like Lucky Luciano and Meyer Lansky. He imprisoned thousands of suspected counterrevolutionaries, including some with close ties to the United States, and executed several hundred.

Time charged that “the bearded strongman” was consolidating his “chaotic dictatorship” with help from foreign Communists and money seized from wealthy Cubans. “Vilification of the US broke all bounds of diplomacy—and even sanity,” the magazine reported after one of his speeches. “No one knows where Castro’s madness will lead him next.”

Anti-Castro terror began soon after the revolution. A large department store in Havana went up in flames, a ship in the harbor was blown up with the loss of more than one hundred lives, sugar plantations were burned, and planes from Florida dropped bombs and mysteriously disappeared. Some of the first attacks may have been carried out by freelance exiles, but soon Allen took control of the campaign. His first decision was to turn it over to Richard Bissell, his deputy director for plans.

“There was considerable discussion of the situation in Cuba,” a note taker wrote after a meeting at CIA headquarters on January 8, 1960. “The Director requested Dick Bissell to organize a special task force to insure that we were attacking this situation from all possible angles.”

“Dickie” Bissell was one of the restless sons of privilege Allen had recruited to help him run the CIA. He came from a wealthy Connecticut family, graduated from Groton and Yale, worked for the Marshall Plan and the Ford Foundation—both of which collaborated closely with the CIA—and ran with Allen’s stylish “Georgetown Set.” As deputy director for plans, he supervised one of history’s farthest-flung intelligence networks, with thousands of officers working out of fifty stations around the world. Bissell not only embraced the CIA ethos of constant action, but physically embodied it. He paced incessantly and charged down hallways. When forced to sit, he channeled his nervous energy into shuffling his feet, wringing his hands, twisting paper clips, and throwing pencils.

“Bissell spent little time before Congress, but lots of time with the President in off-the-record meetings,” one historian has written. “What happened in those meetings no one knew, but it was likely to be interesting. Many believed that next to President Eisenhower, Richard Bissell had more raw power—power to make things happen, power to change the shape of the world—than any man in Washington.”

On January 15 Allen asked the Special Group—the secret body that reviewed covert operations—for authorization to begin plotting against Castro. Eisenhower said he would favor any plot to “throw Castro out” because he was a “madman.” By mid-January, the CIA had eighteen officers in Washington and another twenty-two in Cuba designing “proposed Cuba operations.”

A lifetime of military command had given Eisenhower the habit of denying covert operations, and he maintained it as president. Less than two weeks after he authorized plotting against Castro, he told reporters that although he was “concerned and perplexed” by Castro’s anti-American statements, the United States would take no action against him. At a Special Group meeting on February 17, he brushed aside a proposal from Allen under which the CIA would sabotage Cuban sugar mills and directed him to come up with more audacious ideas, “including even possibly things that might be drastic.” Yet when asked about Cuba during a trip through Latin America in March, he insisted that the United States had “no thought of intervention.”

Eisenhower launched the anti-Castro operation with determination and focused enthusiasm. He gave his orders directly to Allen and Bissell. “There was an informal but understood short cut in the chain of command,” an internal CIA history later concluded. “Basic decisions were made at the DDP, DCI, or Presidential level.”

Allen presented “A Program of Covert Action Against the Castro Regime,” written by Bissell, to a combined meeting of the Special Group and the National Security Council on March 17, 1960. It proposed a multi-stage operation “to bring about the replacement of the Castro regime with one more devoted to the interests of the Cuban people and more acceptable to the US, in such a manner as to avoid any appearance of US intervention.” The CIA would build a covert network inside Cuba, saturate the island with anti-Castro propaganda, infiltrate small teams of guerrilla fighters, use them to set off a domestic uprising, and provide a “responsible, appealing, and unified” new regime.

Eisenhower asked several questions, then said he could imagine “no better plan” and approved. He insisted on one condition: American involvement must be kept strictly secret.

“The great problem is leakage and breach of security,” he said. “Everyone must be prepared to swear he has not heard of it.”

With that, Eisenhower made the overthrow of Castro an official though secret U.S. policy goal. Something else, almost as momentous, emerged from that meeting. Allen spoke first, but when there were questions, he deferred to Bissell. It was an early sign that Allen would not supervise this operation.

The anti-Castro plot was as ambitious a project as the CIA had ever undertaken. Much hung on the outcome. Allen, however, floated above it. Each time he and Bissell came to the White House to brief Eisenhower on its progress, Bissell took the lead while Allen listened. When Bissell briefed the Joint Chiefs of Staff on April 8, Allen did not even attend.

Allen had once played the role of clandestine world shaper and suspected second-most-powerful-man-in-Washington. In the late 1950s he ceded it to Bissell. This was a remarkable fade, a deepening of character traits—distraction, inability to focus, lack of attention to detail, aversion to rigorous debate—that people around him had long observed.

Stories of Allen’s behavior circulated quietly. One day in 1958, an analyst brought him a new batch of U-2 photos but found him unwilling to switch off his radio, which was broadcasting a Washington Senators game. He paid little attention to the photos and remained absorbed in the game, muttering comments like, “He couldn’t hit a bull in the ass with a banjo.” With this same extreme inattention, he absented himself from planning the Bay of Pigs invasion.

“He had turned the whole thing over to Dick Bissell three quarters of the time,” William Bundy, a Kennedy adviser, said afterward. “I had the feeling that by then he was slowing down a little. Thinking about it, after the whole thing was over, I came to the conclusion that he hadn’t been quite the man I had known. All through, he hadn’t been as much on top of the operation as I had expected.”

Bissell had overseen development of the U-2 spy plane, but his more relevant experience was running the theatrical “rebel air force” that had helped push Jacobo Arbenz from power in Guatemala in 1954. Most of the officers he assembled for his anti-Castro operation were also veterans of the Guatemala campaign. Tracy Barnes, David Atlee Phillips, J. C. King, and E. Howard Hunt were given roles approximating those they had played during PB/Success. Their team leader, Jacob Esterline, had directed the Washington end of the Guatemala coup and afterward became CIA station chief in Guatemala.

All had enough experience to recognize the considerable differences between Guatemala in 1954 and Cuba in 1960.

One of Castro’s closest comrades, the Argentine-born guerrilla Che Guevara, had been in Guatemala in 1954 and witnessed the coup against Arbenz. Later he told Castro why it succeeded. He said Arbenz had foolishly tolerated an open society, which the CIA penetrated and subverted, and also preserved the existing army, which the CIA turned into its instrument. Castro agreed that a revolutionary regime in Cuba must avoid those mistakes. Upon taking power, he cracked down on dissent and purged the army. Many Cubans supported his regime and were ready to defend it. All of this made the prospect of deposing him daunting indeed.

Yet most of the CIA’s “best men” emerged from backgrounds where all things were possible, nothing ever went seriously wrong, and catastrophic reversals of fortune happened only to others. World leaders had fallen to their power. They never believed that deposing Castro would be easy, but they relished the challenge. This was why they had joined the CIA.

Quietly, but watched closely by Castro’s spies, CIA officers fanned out through the Cuban sections of Miami, where anti-Castro fervor ran hot. They recruited a handful of exiles to serve as the political front for a counterrevolutionary movement, and dozens more who wanted to fight. The would-be guerrillas were brought to camps in Florida, Puerto Rico, Guatemala, and the Panama Canal Zone and trained in tactics ranging from air assault to underwater demolition.

Tensions between Havana and Washington rose steadily. Cuba recognized the People’s Republic of China and signed a trade agreement with the Soviet Union. Tankers carrying Soviet petroleum arrived in Cuba. American oil companies refused to refine it. Castro nationalized the recalcitrant companies. The United States stopped buying most Cuban sugar. Cuba began selling sugar to the Soviets.

In mid-1960 this hostility broke beyond politics and economics and into the Cuban soul. The Eisenhower administration pressed the International League, one of professional baseball’s top minor leagues, to announce that it was pulling its baseball team, the Sugar Kings, out of Havana. Love of baseball is deeply ingrained in the Cuban psyche. Castro, an avid fan who had been known to suspend cabinet meetings so he could watch the Sugar Kings play, protested that this blow violated “all codes of sportsmanship.” He even offered to pay the team’s debts. It was to no avail. The Sugar Kings became the Jersey City Jerseys, who went bankrupt the next year. The Cuban people lost one of their strongest sentimental ties to the United States.

“The thing we should never do in dealing with revolutionary countries, in which the world abounds, is to push them behind an iron curtain raised by ourselves,” Walter Lippmann warned in a column after the withdrawal of the Sugar Kings. “On the contrary, even when they have been seduced and subverted and are drawn across the line, the right thing to do is to keep the way open for their return.”

* * *

Fears of the threat from Cuba gripped Washington. So did fears of raging nationalism in the Congo. Allen, however, was most steadily preoccupied with a third country: Laos.

History is littered with the names of small places that suddenly flash to the center of world attention. So it was with Laos in the late 1950s. Some Americans came to see it as a vulnerable outpost of freedom, threatened by Communist aggression. Allen was one of them. In the jungles of Laos, he and his men launched the largest paramilitary operation the CIA had yet conceived.

Laotian leaders sought to keep their country out of the East-West conflict, and the American ambassador, Horace Smith, advised Washington to accept a neutral Laos. Eisenhower, however, rejected neutralism because it implied cooperation with Communists. Ambassador Smith was removed. CIA officers forged several thousand tribesmen into a secret army, and supported royalist factions in a civil war against neutralists and Communists. Ho Chi Minh sent units from the North Vietnamese army to fight in Laos. American and Soviet weaponry poured in. Pitched battles foreshadowed the carnage to come in Vietnam.

“We must not allow Laos to fall to Communism,” Eisenhower told aides at the White House, “even if it involves war.”

Although Allen never spoke afterward about this “secret war,” his right-hand man, Bissell, came to believe it might have been misconceived. “Our failure to support [neutralism] reflected Washington’s inability to understand the ground situation in Laos,” he later wrote. “Had we shown more open-mindedness (which is not always compatible with crisis management), the advice and perceptions of experts on Laotian politics, history, and culture might have received more attention.”

* * *

Allen stepped out of a courier plane on July 23, 1960, and into a car that took him to Hyannis Port, where he had come to brief Senator Kennedy. This was part of a traditional effort to maintain a modicum of comity between presidential candidates on national security issues. Allen knew Kennedy from their days relaxing in Florida, and their shared fascination with covert action gave them a special bond. On that summer day, the director of central intelligence spent two hours with the Democratic presidential nominee. By his own account he mentioned Cuba, but said nothing about “our own government’s plans or programs for action.” Outside, the two men bantered with reporters.

“I just told Kennedy what he could read in the morning Times,” Allen told them.

Much debate surrounds this briefing. Kennedy’s opponent, Vice President Richard Nixon, later suggested that it might have cost him the presidency. Within the Eisenhower administration, Nixon was actively promoting the plot against Castro, but he was sworn to secrecy. He suspected that Kennedy realized this after Allen’s briefing. In campaign speeches, Kennedy boldly vowed never to tolerate “a hostile and militant Communist satellite” or “a potential enemy missile or submarine base only ninety miles from our shores.” Nixon could not reply.

“Are they falling dead over there?” Nixon asked an aide in frustration over what he saw as the CIA’s failure to act. “What in the world are they doing that takes months?”

American newspapers closely covered the presidential campaign. They also had plenty of foreign news to report, including the startling split between China and the Soviet Union, new rumblings of war in Indochina, and reverberations from the U-2 spy plane crisis. One historic story, however, went unreported and remained secret for decades.

This was the summer when Eisenhower did twice what no previous American president is known ever to have done: approve plans to assassinate a foreign leader.

In accordance with ancient principles of statecraft, Eisenhower never explicitly decreed anyone’s death. Understandings of his intent emerged from private conversations he had with Allen, and from his veiled comments at small meetings. Castro was the first he seemed to sentence. On May 13, 1960, after a briefing from Allen, Eisenhower told the Special Group he wanted the Cuban leader “sawed off.” His second target, Lumumba, had not yet risen to power.

Years later Richard Bissell, who set both assassination plots in motion, testified that Allen ordered him to do so. Both times, he said, Allen told him the orders had been approved “at the highest level.”

“In that period of history, its meaning would have been clear,” Bissell recalled. “Eisenhower was a tough man behind that smile.”

Since no American intelligence officer had ever been sent to kill a foreign leader, Bissell had to conjure a way to strike at Castro. His idea was either brilliant or ridiculous: hire the Mafia.

American gangsters had forged a rewarding partnership with Batista and lost everything when Castro swept to power. Bissell saw what he wanted: men angry enough at Castro to want him dead, and experienced enough to know how to kill him. He dispatched a middleman to meet with “Handsome” Johnny Roselli, a dapper Mafia figure whom the FBI had connected to thirteen murders. Roselli brought other gangsters into the plot. At one point the CIA passed them six poison pills compounded by Dr. Sidney Gottlieb, chief of the agency’s “health alteration committee.” Allen did not monitor this project. Bissell mentioned it to him once, and he “only nodded.”

On August 18, 1960, as the plot to kill Castro was unfolding, Eisenhower decreed his second death sentence. Lumumba’s meteoric rise in the Congo terrified Washington. It temporarily distracted Eisenhower. He found himself juggling two regime change operations, both involving murder.

After Kennedy won the presidential election in November, Eisenhower might have frozen the anti-Castro operation, or at least asked Allen to test Kennedy’s interest. Instead he expanded it. He approved what Bissell later called a “change in concept”; rather than smuggle small teams of infiltrators into Cuba, the CIA would launch a full-scale invasion, perhaps with support from the U.S. military. Eisenhower’s national security adviser, Gordon Gray, suggested staging a phony Cuban attack on the American base at Guantánamo Bay to use as a pretext for war.

Against this background, Allen and Bissell flew to Palm Beach on November 18 to brief President-elect Kennedy on CIA operations around the world. They sat near the pool, hunched over a map. Precisely what was said remains uncertain. By most accounts the CIA men referred to the anti-Castro plot but did not impress Kennedy with its scope.

On November 29, Eisenhower awoke to the good news that Lumumba had been arrested. Years later, a CIA reconstruction of the anti-Castro plot included this passage: “On November 29, 1960, the level of interest of the US Government escalated sharply with the sudden resurgence of interest on the part of President Dwight David Eisenhower. In contrast to the period from July 1960 through the presidential election of early November—when, as noted earlier, there was, at most, minimal attention to the developing anti-Castro program at the White House level—suddenly the President emerged as one of the principal decision makers.… When asked for an explanation of this sudden resurgence, Jake Esterline, then chief [of the CIA Cuba task force], stated, ‘I can’t explain it.’”

One explanation lies in what only a handful of people could then have known. Eisenhower approved covert action against Castro early in 1960, but Lumumba’s sudden emergence in the Congo distracted him. When he received news that Lumumba had been captured, he realized he had won his African battle. Immediately he turned back to Cuba. He summoned Allen and Bissell to the White House and ordered them to repeat in Cuba what the CIA had just achieved in the Congo. “Take more chances and be aggressive,” he told them.

On that day—November 29, 1960—one Dulles “monster” fell into the hands of mortal enemies and President Eisenhower ordered redoubled covert action against another.

Preparations for the invasion of Cuba steadily intensified. Bissell and his men consolidated their exile army at a secret training camp in Guatemala. They borrowed several vintage B-26 bombers from the Alabama Air National Guard, repainted them with Cuban insignia, and prepared to use them for air raids that would be portrayed as the work of defecting Cuban pilots. As the base for their clandestine “air force” and embarkation point for their exile army, they chose a bluff near Puerto Cabezas, a sleepy town on the Caribbean coast of Nicaragua. They code-named it Happy Valley.

Allen understood that all of this was happening, but none of it was the result of his decisions or directives. He watched from the sidelines. Only once during the months of planning for the invasion of Cuba did he present an independent report to the Special Group. It had nothing to do with the operation itself, but reflected how close he remained to his old friends on Wall Street.

“During the 21 December 1960 meeting of the Special Group, Allen Dulles briefed the attendees on a meeting that he had participated in the previous day in New York with a group of American businessmen,” according to a CIA account that remained secret for nearly half a century. “In attendance at this meeting were the vice president for Latin America of Standard Oil of New Jersey, the chairman of the Cuban-American Sugar Company, the president of the American Sugar Domino Refining Company, the president of the American & Foreign Power Company, the chairman of the Freeport Sulphur Company and representatives from Texaco, International Telephone and Telegraph, and other American companies with business interests in Cuba. The tenor of the conversation was that it was time for the US to get off dead center and take some direct action against Castro.”

At the next Special Group meeting, on December 28, discussion turned to military requirements for the exile invasion. This time Allen deferred not to Bissell, but to Colonel Jack Hawkins, a Marine Corps amphibious warfare expert who had been detailed to organize the landing. Hawkins was forceful—and chillingly prophetic.

“It is axiomatic in amphibious operations that control of air and sea in the objective area is required,” he said. “The Cuban air force and naval vessels capable of opposing our landing must be knocked out or neutralized before our amphibious shipping makes its final run to the beach. If this is not done, we will be courting disaster.… The operation [should] be abandoned if policy does not provide for use of adequate tactical air support.”

Events moved quickly as 1960 turned to 1961. Arms from Communist countries were unloaded in Havana. The American aircraft carrier Franklin D. Roosevelt, carrying marines and accompanied by destroyers, began maneuvers off Cuba’s coast. A talkative exile leader in Miami bragged to reporters that his fighters were “ready to invade.” Cubans built barricades along the shoreline.

On New Year’s Day a powerful bomb exploded in Havana. “It is the American Embassy that is paying the terrorists to place bombs in Cuba!” Castro told a cheering crowd the next night. Then he said he would no longer allow the United States to station more than eleven diplomats at its embassy in Havana. Eisenhower responded by shutting the embassy entirely and breaking diplomatic relations with Cuba. Castro warned Cubans that this meant an invasion was imminent.

“We don’t know what they’re talking about,” Eisenhower’s press secretary told reporters in Washington.

At a Special Group meeting on January 4, the CIA circulated a memo outlining “preparations for the conduct of an amphibious/airborne and tactical air operation against the Government of Cuba.”

“The initial mission of the invasion force will be to seize and defend a small area,” the memo said. “It is expected that these operations will precipitate a general uprising throughout Cuba and cause the revolt of a large segment of the Cuban army and militia.… The way will then be paved for United States military intervention aimed at pacification of Cuba, and this will result in the prompt overthrow of the Castro government.”

Six days later the New York Times carried a startling headline: “US Helps Train an Anti-Castro Force at Secret Guatemalan Air-Ground Base.” The story was accompanied by a map pinpointing the CIA camp, where it said “commando-like forces are being drilled in guerrilla warfare tactics by foreign personnel, mostly from the United States.”

This was not the first sign that operational security had been breached. The Miami Herald had prepared a similar story, but withheld it after Allen warned editors that publication “would be most harmful to the national interest.” Allen also managed to have aWashington Post story killed. Much of the material in those suppressed stories, however, surfaced elsewhere. The Nation ran a report headlined “Are We Training Cuban Guerrillas?” A Guatemalan newspaper, La Hora, sent reporters to the CIA camp and published a host of details. Rumors about the planned invasion coursed through Miami. Allen persuaded the New York Times to downplay its story—it took up one column at the center of the front page, rather than four columns at the top—but so much was already known about the operation that Times editors felt justified publishing what they had.

“I decided that we should say nothing at all about this article,” Eisenhower later wrote.

It was an odd decision. Eisenhower had repeatedly warned that the anti-Castro operation could succeed only if American involvement remained secret. Now any hope of secrecy was gone. Upon realizing this, Eisenhower or Allen—or both—might have stepped back and reconsidered the plot. Instead they pressed ahead, determined to fight and reassured by a diffuse, supra-rational assumption that American power must always prevail in the end.

“The desire to contain the spread of Communism in our hemisphere had grown in the light of ongoing incursions in Africa and Asia,” Bissell wrote later. “Propelled by the momentum of our planning, the operation had been transformed from a guerrilla movement to a full-scale invasion.… Kennedy inherited certain policy decisions of the previous administration and was under pressure to carry them out.”

At nine o’clock on the morning of January 19, 1961, Eisenhower’s last full day in office, he welcomed Kennedy to the White House. The incoming and outgoing presidents spent nearly three hours together. The first foreign crisis they discussed was the one in Laos. Kennedy brought up the obvious next one.

“Should we support guerrilla operations in Cuba?” he asked.

“To the utmost,” Eisenhower replied. “We cannot have the present government there go on.”

* * *

During the first days of his presidency, Kennedy learned details of the plot against Castro. So did attentive Americans. Time reported “guerrilla training camps in Florida and Guatemala, arms-carrying PT boats that average a trip a week to Cuba, [and] an air group of some 80 flyers who reportedly fly out of the mystery field at Retalhuleu in Guatemala and the inoperative US Marine Corps Opa Locka airbase in Florida.”

Kennedy faced a no-win situation. He was young, inexperienced in world affairs, and new in office. During his campaign he had vowed to confront Castro. Many Americans wished him to do so. Now Allen—with Bissell always at his side—was giving him a plan.

Allen pointedly reminded Kennedy that canceling the operation would give him a “disposal” problem. Cuban exiles at the Guatemala camp would have to be discharged. Many would return to Miami. Their story would be, “We were about to overthrow Castro, but Kennedy lost his nerve and wouldn’t let us try.” This narrative would become part of Kennedy’s permanent legacy.

“We made it very clear to the President that to call off the operation would have resulted in a very unpleasant situation,” Allen later said.

Kennedy came into office determined to reshape relations between the United States and Latin America. On March 1 he signed an executive order creating the Peace Corps, and called for volunteers “anxious to sacrifice their energies and time and toil to the cause of world peace and human progress.” Two weeks later, at a glittering White House reception for 250 guests, he unveiled the Alliance for Progress, an ambitious new aid program that aimed to transform Latin America while proving that “liberty and progress walk hand in hand.” As Kennedy imagined a new era of hemispheric cooperation, however, the plan to invade Cuba gathered momentum.

“Allen and Dick didn’t just brief us on the Cuban operation, they sold us on it,” one of Kennedy’s aides groused afterward. Another said the two CIA men “fell in love with the plan and ceased to think critically about it.” Allen conceded their point.

“You present a plan, and it isn’t your job to say, ‘Well, that’s a rotten plan I’ve presented,’” he reasoned. “In presenting the merits of the plan, the tendency is always—because you’re meeting a position, you’re meeting this criticism and that criticism—to be drawn into more of a salesmanship job than you should.”

None of Kennedy’s security advisers raised serious doubts about the plan, but some on the fringes of power did. One White House aide, Arthur Schlesinger Jr., sent Kennedy a memo warning that the United States would certainly be blamed for any invasion of Cuba, and that this would “fix a malevolent image of the new Administration in the minds of millions.” Senator J. William Fulbright of Arkansas, the chairman of the Senate Foreign Relations Committee, counseled him to treat Castro as “a thorn in the flesh, but not as a dagger in the heart.” When former secretary of state Dean Acheson visited the White House, Kennedy told him that the CIA was preparing an invasion of Cuba and sketched out the plan. Acheson was incredulous.

“Are you serious?” he asked. “It doesn’t take Price Waterhouse to figure out that fifteen hundred Cubans aren’t as good as twenty-five thousand.”

Kennedy had doubts about the invasion plan, and Bissell accommodated each of them. The plan called for exiles to land near a town below the rugged Escambray Mountains, but Kennedy feared this would be too “noisy.” Bissell satisfied him by choosing a remote beach one hundred miles eastward, at the Bay of Pigs. When Kennedy worried that using sixteen disguised planes for the first wave of air strikes would increase the odds that the CIA’s role would become clear, Bissell agreed to cut the fleet to eight. Kennedy insisted that the United States military must not be involved; Bissell assured him this would not be necessary.

Historians have long wondered why Bissell allowed the operation to proceed despite these major changes, rather than telling Kennedy that they greatly reduced the chances for success.

“[He] still thought it would succeed, even as modified,” one historian has written. “Personal pride and ambition, too, may have encouraged Bissell to accept mounting changes and risks. His reputation in the CIA and the Kennedy administration was riding on this operation, as was his position as Allen Dulles’s heir-apparent. To cancel would have been equivalent to a forfeit. Nothing in Bissell’s character suggests this would have been an acceptable outcome to him. Another possible reason … was that Bissell assumed President Kennedy would not let it fail—would do, that is, whatever was necessary to make it succeed, even if that meant sending US military forces to the rescue. Yet another possibility: Bissell assumed the Mafia would finally get its act together and take out Castro before, or coincident with, the invasion.”

Bissell ignored one last, poignant warning. It came on Sunday morning, April 9, just eight days before the exile army was supposed to storm ashore at the Bay of Pigs. Bissell was at his home in the Cleveland Park section of Washington when his doorbell rang. Outside were Jacob Esterline, the CIA officer he had put in day-to-day charge of the operation, and Colonel Jack Hawkins, its senior military planner. They were evidently overwrought after a night of agonizing. Bissell ushered them in, and they poured out their hearts. They told him what he already knew: the new landing beach was isolated, with no local population to support the invaders and few escape routes; there would not be enough air cover to prevent Castro from counterattacking; the secrecy that was an essential part of the original plan had evaporated. Given these new conditions, they told Bissell, the invasion was certain to end in “terrible disaster.” If Bissell did not cancel it, they would resign.

Not even this appeal from the operation’s two most important planners moved Bissell. He told them the plot was too advanced to be called off and, as Hawkins later put it, “earnestly asked us not to abandon him at this late date.” His appeal to their patriotism andesprit de corps finally prevailed. As they drove away from his house, a last chance vanished with them.

“We made a bad mistake by not sticking to our guns and staying resigned,” Hawkins later lamented.

Equally striking is that the two officers considered Bissell the only target for their plea. Allen had so fully distanced himself from the operation’s planning that they never considered appealing to him.

At a news conference on April 12, Kennedy asserted that “there will not be, under any conditions, an intervention in Cuba by United States armed forces.” The next morning, CIA planes began transporting Cuban exiles from their training camp in Guatemala to the Happy Valley base on Nicaragua’s Caribbean coast. Before dawn on April 17, the exile force, about fourteen hundred strong, waded ashore at the Bay of Pigs. Thousands of Cuban troops counterattacked. Castro himself arrived to take command.

As this news was flashed back to Washington, Colonel Hawkins made a frantic call, awakening his boss, General David Shoup, the commandant of the Marine Corps. He told Shoup that all would be lost unless American planes were quickly ordered to strike against Castro’s troops.

“You’ve got to get ahold of the President,” Hawkins pleaded. “We’re going to fail.”

“Christ knows I can’t do anything,” Shoup replied.

Kennedy had made clear that he would not use American military power to support the invasion. When the crucial moment came, he refused to change his mind. News of his resolution was radioed from Washington to the base at Happy Valley. The senior military officer there, Colonel Stanley Beerli, commander of the Alabama Air National Guard, threw his cap to the ground in disgust.

“There goes the whole fucking war!” he swore.

On that excruciating day, the invasion force was scattered by Cuban artillery, attacked by Cuban bombers, and overwhelmed by Cuban troops. Allen was nearby. He was not in a spotter plane or aboard one of the many American warships poised near the Cuban coast. Instead he was in San Juan, Puerto Rico, joining Margaret Mead and Dr. Benjamin Spock as speakers at a convention of young businessmen. Radio Moscow reported that he had traveled to San Juan to “command in person the aggressive actions against Cuba.” That was the logical assumption; what else would the chief of a covert service be doing while his service launched its least covert operation ever? The truth was more prosaic. Allen was doing just what he seemed to be doing: delivering a bland speech while men he had helped send to war were dying on a beach not far away.

“Well, how is it going?” he asked an aide who met his plane late that night in Baltimore.

“Not very well, sir,” came the reply.

“Oh, is that so?”

The two men chatted on the ride to Allen’s home in Georgetown. When they arrived, Allen invited his aide in for a drink. Over whiskey, he shifted the subject away from Cuba and began rambling aimlessly. The aide later used a single word to describe this moment: “unreal.”

At White House meetings the next day, Kennedy fended off more pleas that he send U.S. forces to support the Bay of Pigs invaders. The strongest came from his chief of naval operations, Admiral Arleigh Burke, who came to the Oval Office late in the evening with an equally agitated Bissell.

“Let me take two jets and shoot down those enemy aircraft,” Burke pleaded.

“No,” Kennedy replied. “I don’t want to get the United States involved in this.”

“Can I not send in an air strike?”


“Can we send in a few planes?”

“No, because they could be identified as United States.”

“Can we paint out their numbers?”


Grasping for options, Burke asked if Kennedy would authorize artillery attacks on Cuban forces from American destroyers. The answer was the same: “No.”

Later that day Kennedy told an aide, “I probably made a mistake keeping Allen Dulles.” By then Allen had also recognized the scope of the disaster. He made his way to the home of one of his old friends, Richard Nixon. Nixon saw immediately that Allen was under “great emotional stress” and offered him a drink.

“I really need one,” Allen replied. “This is the worst day of my life.”

“What’s wrong?”

“Everything is lost.”

So it was. More than one hundred of the invaders died. Most of the rest were rounded up and imprisoned. For Castro it was a supreme, ecstatic triumph. Kennedy was staggered.

“How could I have been so stupid?” he wondered aloud.

Others were equally stunned. Criticism of the CIA, in both the press and Congress, rose to unprecedented intensity. Allen was not spared. The cover story in Time, headlined “The Cuba Disaster,” questioned his very concept of intelligence.

“Last week the CIA was back in the news in a big way—and will probably stay there for some time, while a basic question that has been long and heatedly debated is argued out,” Time wrote. “Should any intelligence-gathering organization also have an operational responsibility? The British have long said no, arguing that a combination of the functions gives such an organization a vested operational interest in proving its intelligence correct. That dual function seems to have been one of the causes of the Cuban tragedy.”

Standing before reporters in the White House, Kennedy took “sole responsibility” for the failure. “Victory has a hundred fathers and defeat is an orphan,” he mused.

Allen fell into a period of shock. Robert Kennedy later wrote that he “looked like living death … had the gout and had trouble walking, and he was always putting his head in his hands.” In the weeks that followed, however, he was invited to White House meetings as usual. No harsh words were spoken.

On May 1 the Senate Foreign Relations Committee held closed hearings into the Bay of Pigs debacle. Allen insisted that the military, not the CIA, was to blame. “We took the highest, the best military advice we could get,” he testified. “This included, of course, the military officers who helped formulate the plans, and also the Joint Chiefs of Staff.”

The top U.S. military commanders were outraged. Admiral Burke was withering in his judgment of Allen.

“The fact is that he just wasn’t involved in that operation,” Burke said. “He showed up at meetings and sat there smoking his pipe.… I blame him for not being there.”

Passions cooled as spring unfolded over Washington. Allen believed he had weathered the storm. He began hovering around the construction site at Langley where the new CIA headquarters was being built. Retirement, he told friends, would come in two years, when he turned seventy.

If Allen had not yet confronted the implications of the Bay of Pigs disaster, Kennedy had. In private he cursed “CIA bastards” for luring him into it, and wished he could “splinter the CIA into a thousand pieces and scatter it into the winds.” One day in August, deciding that a decent interval had passed, he summoned Allen to the White House.

“Under a parliamentary system of government, it is I who would be leaving office,” he told Allen. “But under our system it is you who must go.”

* * *

Kennedy allowed Allen to remain in office until a dedication ceremony could be held at the new Langley headquarters. It was set for November 28, 1961. Hundreds of CIA officers attended. Kennedy gave a lighthearted speech.

“Your successes are unheralded, your failures are trumpeted,” he told the crowd. “I sometimes have that feeling myself.”

The incoming CIA director, John McCone, a former chairman of the Atomic Energy Commission, was seated beside Kennedy. Richard Bissell, whom Kennedy had removed from the agency along with Allen, was nearby. It was a moment to heal family wounds.

“Would you step forward, Allen?” Kennedy asked after finishing his speech.

When Allen reached the podium, Kennedy produced a National Security Medal, the highest award for an American intelligence officer. He pinned it to Allen’s lapel and said, “I know of no man who brings a greater sense of personal commitment to his work, who has less pride in office than he has.”

Then a curtain was drawn back to reveal a Bible verse chiseled into granite. It graces the entrance wall to this day: “And ye shall know the truth, and the truth shall make you free.”

A year later, Castro released the Bay of Pigs prisoners in exchange for $52 million in donated food and medicine. That hardly closed the episode, however. Its effects have reverberated through history. This was the first time the CIA was fully unmasked seeking to depose the leader of a small country whose crime was defying the United States. It became a reviled symbol of imperialist intervention. A new wave of anti-Americanism began coursing around the world.

In 1965 two former Kennedy aides, Theodore Sorensen and Arthur Schlesinger Jr., published articles that held Allen largely to blame for the Bay of Pigs fiasco. Sorensen wrote that Kennedy had asked Allen if he was sure the invasion would succeed and that Allen had replied: “I stood right here at Ike’s desk and told him I was certain the Guatemala operation would succeed. And Mr. President, the prospects for this plan are even better than they were for that one.”

Allen set to work on a sharp rebuttal called “My Answer to the Bay of Pigs.” “The myth that President Kennedy was advised that the Cuban operation was sure to succeed [is] diametrically opposed to the facts,” he wrote. “We had a fighting chance and no more. That was the position I took with regard to Cuba in the highest counsels of our government.”

Allen’s sister Eleanor believed that he “had already begun to lose his command over his memory and ideas” and persuaded him not to publish this article. It survives—a jumble of typescript and handwritten notes—only in his personal archive. One of the notes suggests an answer to the question of why he allowed the Bay of Pigs invasion to proceed despite clear signs that it would fail.

“We felt that when the chips were down—when the crisis arose in reality—any action required for success would be authorized, rather than permit the enterprise to fail,” Allen wrote. “We believed that in a time of crisis, we would gain what we might lose if we had provoked an argument.”

Eight years of experience under Eisenhower led Allen to believe this. He presumed that Kennedy, like Eisenhower, would do whatever was necessary to ensure victory once a covert operation was under way. Apparently he never took seriously Kennedy’s vow to keep the United States out of war in Cuba.

Eleanor was another casualty of changing times in Washington. Secretary of State Dean Rusk called her into his office early in 1962 and told her, “The White House has asked me to get rid of you.” Part of the impetus may have come from Attorney General Robert Kennedy, who had been outraged at the Bay of Pigs failure and, by one account, “didn’t want any more of the Dulles family around.” Eleanor unwillingly left the State Department after fifteen years. She went on to teach at Duke and Georgetown, wrote several books, and traveled widely, most often to Germany, including with President Lyndon Johnson to attend Konrad Adenauer’s funeral in 1967. Her constitution proved hardier than those of her brothers; she remained active until near the end of her life, which came in 1996, when she was 101 years old.

In retirement, Allen found himself in demand as an after-dinner speaker. He also devoted himself halfheartedly to writing. His book The Craft of Intelligence was unspectacular—several chapters were ghost-written by a CIA comrade, E. Howard Hunt—but two collections of spy stories he assembled from history and fiction sold well. He spent time in Switzerland, where his son was in a sanatorium, and in the Bahamas. Clover traveled with him. He took pleasure in grandchildren. Twice, most unexpectedly, President Johnson gave him delicate assignments that brought him back to public life.

Allen was at his home at Lloyd Neck when he received news of John F. Kennedy’s assassination on November 22, 1963. A week later, Johnson called. He wanted Allen to serve on a high-level panel that would investigate the assassination—the Warren Commission.

Johnson told friends in Congress that the Kennedy assassination had “some foreign complications, CIA and other things.” Placing Allen on the Warren Commission ensured that these “complications” would remain secret. Allen never told the other members of the Warren Commission that the CIA had plotted to kill Castro, or revealed what it knew about Kennedy’s accused assassin, Lee Harvey Oswald. He advised other members of the commission about ways to question CIA officers, while at the same time advising the officers how to reply. By one account he “systematically used his influence to keep the commission safely within bounds, the importance of which only he could appreciate.… From the start, before any evidence was reviewed, he pressed for the final verdict that Oswald had been a crazed gunman, not the agent of a national and international conspiracy.”

Allen was in a unique position: the former director of central intelligence, dismissed by President Kennedy, helping to investigate Kennedy’s murder while guarding the CIA’s own murder plots. Some have found this suspicious.

As the Warren Commission was completing its work, Johnson asked Allen to take on a very different mission. On June 20, 1964, three civil rights workers disappeared in Mississippi. Johnson wanted to send an envoy and settled on Allen because he was not identified with any side in the civil rights debate. Allen protested his ignorance—he did not even know the name of Mississippi’s governor—but accepted. He spent two days in Mississippi, met with black and white leaders, and submitted a bland report warning about polarization between segregationists and a “new breed of Negro agitators.” It had no apparent effect and was quickly forgotten.

Once these projects were behind him, Allen made a sentimental trip back to Ascona in southern Switzerland, where he had helped broker the “secret surrender” of Nazi forces twenty years before. Other veterans of the operation met him there for a reunion. One was Karl Wolff, the former “second man of the SS.” Wolff had reason for gratitude. Documents released decades later show that Allen played a key role in shielding him from prosecution at the Nuremberg tribunal after World War II; keeping him free for more than a decade, until a West German court convicted him of complicity in genocide; and, after he was released, ensuring that he was not banned from employment as a convicted war criminal.

Allen weakened during the late 1960s. His body ached. A torrent of anti-CIA books, articles, and investigations disoriented him. He began losing his way on the streets of Georgetown. “Perhaps it was what we call Alzheimer’s disease today,” a relative who cared for him suggested later.

When Allen came to CIA headquarters one morning in 1967 for a final honor, he was pale and overweight, had trouble walking, and looked all of his seventy-four years. Richard Helms, the director of central intelligence, welcomed him warmly and then unveiled a new memorial. It was a profile of Allen, chiseled in bas-relief, above a simple inscription:


Director of Central Intelligence 1953–1961

His Monument Is Around Us

Allen talked of writing a memoir but never did. “I am too old, I have forgotten so much,” he told historians who approached him in his later years. He had several strokes. After the last one, he was admitted to Walter Reed Army Medical Center. His room was near the one in which his brother had drawn a final breath ten years before. He died there just before midnight on January 29, 1969, of influenza complicated by pneumonia.

Allen’s memorial service, as he wished, was small. Only a few dignitaries attended, led by Vice President Spiro Agnew, representing President Nixon. Tributes were warm but brief. The Washington Post called Allen “the most creative, powerful, and eminent American intelligence officer of recent times.”

“He possessed a zest for the romance of cloak-and-dagger work which is rarely found at the top of intelligence bureaucracies,” the Post concluded. “On the other hand, the Bay of Pigs—another product of the Dulles CIA—is generally considered the greatest US intelligence blunder.”

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