13

Dangerous Ideas

Shortly after 9:00 p.m. on March 12, 1956, Jesús de Galíndez, a lecturer in Spanish and government at Columbia University, finished leading a graduate seminar at Hamilton Hall and headed home. One of his students offered to drive him to the Columbus Circle subway station so he could take a downtown train to his Greenwich Village apartment. He was never seen again by friends or colleagues.

Galíndez was a charming, forty-year-old bachelor, popular with his students and attractive to women. Born to a prominent Basque family in Spain and educated as a lawyer, Galíndez was tall, slim, well dressed, and good-looking, with deep, dark eyes, and a receding hairline that added to his distinguished appearance. He emanated a warm, if somewhat melancholy, intelligence. He had the look of a man who had seen perhaps too much of the world but was determined not to be undone by it.

During the Spanish Civil War, Galíndez had fought in a Basque brigade against Franco’s forces. After Franco’s triumph, he fled for his life to France and booked passage on a ship to the Dominican Republic, where strongman Rafael Trujillo had promised sanctuary to Spanish exiles. Arriving in late 1939 in Santo Domingo, the capital city, which the dictator had renamed Ciudad Trujillo after himself, Galíndez found work as a professor of history and languages, and later as a government adviser. But he and most of his fellow Spanish refugees soon discovered that they had “left Franco’s frying pan and landed in Trujillo’s fire,” in the words of a Dominican diplomat.

Rafael Trujillo had ruled the Dominican Republic since 1930, an operatic reign of terror that combined equally florid measures of violence and pageantry. His theater of blood included the horrific 1937 mass slaughter of thousands of Haitian immigrant workers, including women and children, many of whom were hacked to death with machetes. Trujillo’s political enemies were rounded up and tortured in the notorious concentration camp at Nigua and in the La Cuarenta dungeon. Others were assassinated and their bodies displayed in macabre festivals, like the murdered rebel leader Enrique Blanco, whose corpse was tied to a chair and paraded throughout his home province, where his peasant followers were forced to dance with his remains.

Those who fell into disfavor with Trujillo’s regime lived in mortal fear of being denounced in the notorious gossip column of the leading government newspaper, El Caribe. Denunciations could ruin careers or destroy lives. It was “a method of [execution] that was slower and more perverse than when he had his prey shot, beaten to death, or fed to the sharks,” as the novelist Mario Vargas Llosa observed. “El Jefe,” as the dictator was known, was a master of fear. During the later years of his regime, in the 1950s, all it took to spread panic in the capital was for one of his security cars to crawl through a neighborhood. The black VW Beetles, known as cepillos, created the suffocating “sensation that Trujillo was always watching,” in the words of one historian.

Trujillo was also infamous for his official larceny, taking over all of his country’s core industries, including oil, cement, meat, sugar, rice—and even the prostitution trade. Running the Dominican economy as a family business, he amassed a personal fortune that made him one of the wealthiest men in Latin America. Trujillo’s sexual appetites were equally gluttonous, earning him the title of “The Goat” on the streets of the capital. He plowed his way through three wives, two mistresses, and countless young women whose physical charms briefly captivated him. Trujillo, whose mother was a Haitian mulatto, sought out plump white women—the beauty standard of the local aristocracy, which never fully accepted the coarse former army sergeant. At his 1929 wedding to socialite Bienvenida Ricardo, Trujillo horrified the guests and confirmed Dominican high society’s worst suspicions when he used his military sword to cut the elegant wedding cake, sending the towering confection—adorned with frosty angels and delicately sculpted sugar flowers—crashing to the floor.

But Trujillo’s common ways won the admiration of many in the poor, uneducated ranks of Dominican society. He was especially popular among men, who admired his naked ambition, sexual aggression, and dandified fashion style. He embodied a strutting style of masculinity known by locals as tigueraje, an earlier version of “gangsta” bravado that turned flashy bad boys, or “tigers,” from the barrios into emblems of cool. Trujillo also provided thousands of young men from the lower orders—including mestizos, blacks, and other traditional social outcasts—a path upward, by expanding the Dominican civil service as well as the military, transforming his army into the second most powerful force in Latin America, after Venezuela’s.

Trujillo further ensured his control of the presidential palace by assiduously courting the powerful giant to the north, pledging his nation’s allegiance to the United States during World War II and the Cold War, and showering money on Washington politicians and lobbying firms. Trujillo’s courtship of Washington paid off. By 1955, John Foster Dulles’s State Department was celebrating the strongman as “one of the hemisphere’s foremost spokesmen against the Communist movement.” That same year, Vice President Nixon visited the Dominican Republic and made a public display of embracing Trujillo. The United States should overlook the notorious defects of the Dominican dictator, Nixon later advised Eisenhower’s cabinet, because, after all, “Spaniards had many talents, but government was not among them.”

Despite his enormous wealth, Trujillo himself was too thuggish a character to work his way into polite company, at home or abroad. But by the 1950s, his roguish social circle had produced several personalities smooth enough to be embraced by the international jet set, including his first daughter, the sexy bad girl, Flor de Oro, and the suave ladies’ man she was once married to and never got over, playboy-diplomat Porfirio Rubirosa. The leading symbol of Dominican masculinity on the world stage, Rubirosa started his career as a lowly military aide to Trujillo, parlaying his connections, good looks, and sartorial elegance into becoming one of the most celebrated Latin lovers of his day—“the Dominican Don Juan,” the “Caribbean Casanova,” as the international press anointed him.

Rubirosa, affectionately known as “Rubi,” was the son Trujillo always wanted—much more polished than his own crude, debauched offspring, Ramfis (named, in Trujillo style, for a character in the Verdi opera Aida). The dictator, like the rest of the Dominican male populace, reveled in the tales of Rubi’s romantic exploits. The dapper playboy had passionate affairs with blond movie goddesses like Kim Novak and courted some of the world’s richest women, including American heiresses Doris Duke and Barbara Hutton, both of whom he married. Some in high circles sneered that Rubirosa was unworthy of their company, a lounge-room charmer with a permanent tan and an oily sheen. But women sang his praises. Hutton was particularly graphic about Rubi’s appeal, recalling her former husband with ripe fondness even after their divorce: “He is the ultimate sorcerer, capable of transforming the most ordinary evening into a night of magic . . . priapic, indefatigable, grotesquely proportioned.”

This was the Dominican image—lusty and glamorous—that Trujillo wanted to project to the world, and particularly to the United States. Maintaining this positive image of robust vitality with his neighbors to the north was not simply a matter of ego gratification for the dictator. Trujillo reaped $25 million a year in foreign aid from Washington, much of which ended up in his personal overseas bank accounts, and he was eager to keep the American dollars flowing. The CIA further enriched the dictator with secret payments, delivering suitcases stuffed with cash to his hotel suite whenever he visited New York for UN meetings.

While Trujillo succeeded in crushing dissent at home, by 1956 there was one man—Jesús de Galíndez—who, in the dictator’s mind, threatened his regime’s world image. Galíndez, who lived in a book-stuffed apartment on lower Fifth Avenue and enjoyed going to Latin dance clubs at night, did not strike his academic colleagues at Columbia as an international man of danger. But to Trujillo, he was a treacherous serpent who was poisoning opinion against his regime. Not long before he vanished, Galíndez had completed a damning, 750-page dissertation on the dictator’s odious rule, “The Era of Trujillo,” and submitted it for a PhD degree at Columbia. Scholarly theses do not normally incite violent passions. But Trujillo knew that Galíndez, who had worked in the Dominican civil service, had inside information about his savage and corrupt regime. El Jefe, who saw the Galíndez monograph as a stab in the back, brooded about the betrayal. Trujillo agents tried to convince Galíndez to sell the manuscript to them, offering as much as $25,000, but the scholar refused. The dictator decided that left him with only one course of action.

Galíndez saw his scholarly exposé of the Trujillo tyranny as part of a broader campaign of popular liberation. In the mid-1950s, ironfisted regimes like Trujillo’s dominated Latin America, with dictators ruling thirteen of the region’s twenty nations. The Eisenhower administration found these despots to be useful Cold War allies; they allowed U.S. corporations to exploit their nations’ people and resources, and they cracked down on labor agitation and social unrest as Communist-inspired. But Galíndez’s scholarly activism—which included numerous magazine articles and pamphlets he published in Mexico and the United States, attacking the Trujillo regime and championing human rights in Latin America—was part of a new intellectual ferment that was challenging the old order.

It was his experience as an exiled Basque freedom fighter, said Galíndez, that made him deeply sympathetic to the region’s social struggles. His own people’s doomed crusade for self-determination made “the problems of Puerto Ricans in New York . . . or the drumbeat of a black Caribbean” reverberate inside him, he wrote.

Galíndez’s life in New York, as a politically active refugee at the height of the Cold War, was a complex web. In addition to his activism against Trujillo, the scholar served as the U.S. representative of the Basque government-in-exile. Galíndez also maintained an ambiguous relationship with U.S. security officials. Galíndez’s escape to the United States in 1946 was no doubt made smoother by the fact that he had been secretly working as an informant for the FBI during the war, passing along information about suspicious pro-Nazi activity in the Caribbean. After he arrived in New York, the bureau asked him to spy on Communist-affiliated members of the anti-Franco resistance in the United States. In May 1951, the special agent in charge of the bureau’s New York office told FBI chief Hoover that Galíndez was “an invaluable informant,” whose reports were “extremely detailed, accurate and thorough.”

But FBI reports on Galíndez also noted that the Basque exile was strongly critical of U.S. foreign policy in the Eisenhower-Dulles era. He had been heard denouncing the administration for supporting the admission of Franco’s Spain to the United Nations, and for backing Latin dictators like Trujillo and Nicaragua’s Anastasio Somoza. In April 1955, Galíndez told an FBI informant in Miami that “since John Foster Dulles entered into the picture, the United States has started to write the blackest pages of its international relations. Never before in the history of the world has one single Government more effectively supported dictatorial powers in free nations.”

Despite his scathing remarks about Eisenhower-Dulles policy, which made their way into Galíndez’s FBI files, the bureau continued to have confidence in him, paying the university lecturer up to $125 a month plus expenses for his information. The FBI also helped Galíndez gain permanent residence status in the United States. The activist-intellectual placed limits on what he would do for the FBI—he refused, for instance, to publicly testify against suspected Communists in the anti-Franco movement, arguing that it would blow his cover. He was clearly playing a deeply intricate game of exile politics, perhaps believing that his relationship with the FBI provided him and his embattled causes some protection.

But the bureau knew that Galíndez was not safe. On March 6, 1956—five days before he disappeared—an FBI official noted in a memo that Galíndez’s dissertation on Trujillo “may involve informant in personal difficulties . . . this matter will be watched closely and the Bureau kept advised.”

Galíndez was well aware of his perilous situation. Trujillo maintained a network of agents in the United States, and they had already killed at least one opponent of his regime in New York. Strange notes were slipped into his books on campus and disturbing phone calls were made to his home. One day, two tough-looking Dominicans in bright tropical shirts sat in on a class he was teaching.

But it was not Trujillo thugs who were responsible for Galíndez’s disappearance on that chilly March night after he taught his final class. His kidnapping was a sophisticated operation run by Robert A. Maheu and Associates, a private detective firm staffed by former CIA and FBI employees that the intelligence agency used as a “cut-out” to do dirty jobs on U.S. soil, where the CIA was forbidden by law to operate.

Grabbed by Maheu agents who were waiting for him in his apartment, Galíndez was drugged and carried into an ambulance, then driven to a small airport in Amityville, Long Island. There he was loaded into a twin-engine Beech airplane that was specially equipped to fly long distances and flown south, stopping for refueling after midnight in West Palm Beach, before continuing on to the Dominican Republic. After landing in Trujillo’s kingdom, Galíndez—still half conscious—was transported to Casa de Caoba, the dictator’s favorite hideaway. There, Trujillo, dressed in a riding outfit, confronted the traitor with the evidence of his betrayal—a copy of the dissertation, which his agents had stolen. “Eat it,” he commanded. The dazed Galíndez took the pile of papers but could not keep hold of them, letting them fall to the floor as his head slumped to his chest. “Pendejo!”screamed the dictator in his high-pitched squeal as he flayed Galíndez’s head with a riding crop.

Galíndez was taken to a torture chamber in the capital city, where he was stripped, handcuffed, and hoisted on a pulley. Then he was slowly lowered into a tub of boiling water. What remained of him was thrown to the sharks, a favorite disposal method of the dictator.

The abduction of the Columbia University academic from the streets of Manhattan is the first flagrant example of what would become known during the War on Terror, with bureaucratic banality, as “extraordinary rendition”—the secret CIA practice of kidnapping enemies of Washington and turning them over to the merciless security machinery in undisclosed foreign locations.

During his final seminar, Galíndez mentioned several times that he was being “threatened by Trujillo people.” Maria Joy, one of his students, thought that he was showing off. But later, after she read about his disappearance in the newspapers, Joy felt “horrified”—not only because Galíndez had vanished but because something like this “could happen in the United States.”

“If this can happen here, what is left?” she wrote in a letter printed in The New Republic. “There is no hope. . . . Everybody who has some sense of responsibility and a feeling for democracy and freedom should be concerned.”

There was a flurry of public concern over Galíndez’s disappearance. On April 24, a group of Columbia University professors asked the Justice Department to investigate charges that Trujillo’s regime had assassinated their colleague. The following day, the case worked its way into President Eisenhower’s press conference when a reporter for the Concord (New Hampshire) Monitor asked if the administration planned to examine whether “the agents of a dictatorship which enjoys diplomatic immunity are assassinating persons under the protection of the United States flag?” Eisenhower replied that he knew nothing about the Galíndez affair but said he would look into it.

But, in truth, the CIA had already moved swiftly to shut down the case. New York Police Department officials, informed that the disappearance was a highly sensitive national security matter, put the case in the hands of the Bureau of Special Services (BOSS), the NYPD’s intelligence section. The CIA, which had no jurisdiction to investigate domestic criminal cases, used secret police units like BOSS to take charge of delicate investigations within the borders of the United States. Dulles himself communicated the importance of the Galíndez case to the NYPD, asking police officials to send a detective to the scholar’s Greenwich Village apartment to retrieve the contents of his briefcase. Police commissioner Stephen Kennedy made sure the CIA director’s request was promptly carried out, and the papers inside Galíndez’s briefcase were delivered to Dulles. Kennedy made it clear to the detective that he was to keep his mouth shut about the errand.

John Frank, the Maheu operative who organized Galíndez’s kidnapping, was closely connected to some of the principal BOSS inspectors working on the case. Frank was a shrewd, ambitious operator who, like Maheu himself, had begun his career as an FBI agent during World War II, before going to work for the CIA. The forty-two-year-old Frank lived in Washington, where Maheu’s detective agency was based. But he kept an office in Trujillo’s salmon-colored, Italian Renaissance–style palace, as the high-paying dictator became an increasingly important client of the Maheu firm. Frank won the trust of the volatile El Jefe, who made him his bodyguard during state visits to Europe and the United States. The Maheu agency was also given a lucrative contract to upgrade Trujillo’s security in the Dominican Republic.

Although Frank liked to play tennis with friends in the spy set and boasted of reading Voltaire in French, he was not part of the CIA’s Georgetown inner circle. Men like Frank and his boss, Maheu, were CIA contractors, entrusted with some of the agency’s most risky and squalid tasks. They were not the sort of men who played tennis on Allen Dulles’s backyard court. Maheu later claimed that the Mission: Impossible TV series was based on his firm’s exploits—a secret team whose actions would be “disavowed” by the government should any of their agents be “caught or killed.” Men like Maheu and Frank were expendable.

Bob Maheu fit the profile of an FBI gumshoe more than a CIA spook. A balding, rubbery-faced man, he had the bright-eyed, genial looks of a comedian who was overly eager to please his audience. But his eyes could go suddenly dead, and his jaw could become grimly set. He came from humble origins—the son of devout Catholic, French-Canadian immigrants who ran a small soda bottling company in a Maine mill town. Maheu worked his way up, graduating from Holy Cross and then Georgetown Law, and getting hired as a field agent by the FBI, where he worked on sensitive national security cases during the war. But Maheu was not content to stay on J. Edgar Hoover’s civil service payroll.

In 1954, he opened up his own security business, with the CIA—which put him on a $500 monthly retainer—as his leading client. The CIA used Maheu and Associates as a front, putting undercover agents on Maheu’s staff. The agency also directed a stream of highly sensitive, and rewarding, contracts to Maheu, including a major job for Greek shipping tycoon Stavros Niarchos that established the company as a leading player in the private security field. Maheu’s firm was hired to help sabotage an agreement between Niarchos’s business rival Aristotle Onassis and the Saudi royal family that the international oil cartel and the Dulles brothers feared would corner the oil shipping business and harm Western interests. The oil caper involved a series of shady maneuvers aimed at smearing the reputation of Onassis—and perhaps even more ruthless actions to eliminate supporters of the Onassis deal in the Saudi royal court. After the successful resolution of the case, a grateful Niarchos gave Maheu a bonus big enough for him to buy a dark blue Cadillac and a split-level house in Sleepy Hollow, Virginia, to which he added a swimming pool. Maheu would become the top-paid security contractor in the country, taking on confidential missions for Vice President Nixon and eccentric billionaire Howard Hughes, who later hired him to run his Las Vegas empire.

Despite his success, Maheu liked to say that he never forgot where he came from. Among the multitude of celebrity photos and gold-plated plaques hanging in his office, he claimed to cherish most of all the wood sign that said “Elm City Bottling,” his family’s mom-and-pop business. “Call it my personal Rosebud,” he wrote in his memoir.

Maheu did not socialize with the top CIA men like Helms, Angleton, and Wisner. He met Dulles only once. “It was an accident,” Maheu recalled years later. There was something about the Dulles brothers’ cozy power act that did not sit well with Maheu. “I always resented the fact that Allen Dulles’s brother was secretary of state. You can’t have respect for the diplomatic pouch and be in intelligence at the same time. The State Department should not have to know how you got the information.”

It was his CIA handlers—Sheffield Edwards, who ran the agency’s security office, and Edwards’s deputy, the hulking Jim O’Connell—whom Maheu trusted and invited to his home. These were the cops of the CIA—tough men, many of them ex-FBI and Catholic, who, like Maheu, were not afraid to get their hands dirty. The CIA had an elite reputation, but within the organization there was a distinct class system: the Ivy League types on the top; the ex-FBI hard guys and former cops in the middle ranks of enforcement; and the even more ruthless, and disposable, hired guns at the bottom.

On Saturdays, Maheu would invite Edwards, O’Connell, and other Washington security types like Scott McLeod—the zealous anti-Communist watchdog who had been hired by Foster Dulles to clean house at the State Department during the McCarthy red scare and then conveniently ditched—to watch Notre Dame football games and enjoy barbecue banquets and clambakes in his backyard. Maheu, who prided himself on his cooking skills, carefully monitored the boiling pots filled with lobsters that he had shipped from Maine. Buoyed by the free-flowing booze at the clambakes, Maheu’s regular crowd would find themselves in cheerful conversation with a curious range of special guests, from senators to gangsters. They were all part of Maheu’s colorful world, where the powerful mingled with the infamous.

Working with Shef Edwards’s team and their contacts in the NYPD’s BOSS unit, Maheu and Frank initially succeeded in containing the Galíndez story. Columbia University president Grayson Kirk—a friend of Dulles and a trustee of several foundations that served as pipelines for CIA funding—did nothing to keep the missing lecturer’s case alive, prompting charges of university “indifference.” Meanwhile, the Trujillo regime spread the word that Galíndez was “suffering from a persecution complex” and had likely disappeared for personal reasons. Phony Galíndez sightings were reported throughout Latin America and as far away as the Philippines.

At the same time, the CIA disseminated other disinformation about Galíndez to its friendly press assets, claiming that the missing scholar had absconded with more than $1 million of CIA funds, which the agency allegedly had given him to set up an anti-Franco underground in Spain. Other CIA documents, which circulated as high as Dulles’s office, tried to brand Galíndez as “a witting tool of the Communists.” The agency’s smear campaign succeeded in making Galíndez’s character the story, rather than the shocking crime, and public interest in the case began to wane.

But in December, just as the story seemed to be flickering out, Trujillo threw gas on the smoldering fire when, in predictable fashion, he went too far and ordered the murder of the young American pilot who had flown Galíndez to the Dominican Republic. Twenty-three-year-old Gerald Murphy had dreamed of being a pilot his whole life, but, prevented by poor eyesight from joining the U.S. Air Force, he pursued a career as a mercenary pilot, winding up in the Dominican Republic, flying missions for Trujillo. “It beats the hell out of Oregon,” the handsome Portland native—who affected a James Dean look, complete with Ray-Bans—told his friends about life in the tropics. But Murphy’s life took a fateful turn when he was engaged by John Frank to fly the heavily sedated Galíndez to Ciudad Trujillo.

John Frank told Murphy that Galíndez was a wealthy invalid who wanted to visit Dominican relatives one last time before he died. But after photos of Galíndez began appearing in the press, the pilot figured out the true identity of his passenger. Given to reckless chatter when he was drinking, Murphy began boasting in Ciudad Trujillo watering holes about the big story that he was sitting on, and his chances of striking it rich by making a deal with the Dominican regime to stay quiet. Trujillo, however, preferred a more certain method of ensuring the pilot’s silence. Frank brought Murphy to the National Palace, telling him he had been granted an audience with El Jefe himself. It was the last time the pilot was seen. On December 4, the young American’s Ford was found on a cliff near a slaughterhouse, where the offal that was dumped into the sea attracted swarms of sharks. Known as the “swimming pool,” the lagoon was a favorite disposal site for Trujillo’s enemies.

Murphy’s suspicious disappearance ignited a new uproar, with his Oregon congressman, Charles Porter, demanding that the Eisenhower administration get to the bottom of this latest Trujillo-related mystery. In March 1957, even Stuyvesant Wainright, the wealthy Republican congressman from Long Island’s Gold Coast, waded into the growing controversy, writing directly to his neighbor Dulles and asking for more information about the Galíndez affair, which he called “an incredible invasion of a human being’s personal protection in our country.” Wainright told Dulles that he felt a personal connection to the case, since Murphy had flown Galíndez to his fate from a Long Island airport. Dulles blandly replied that the CIA had no jurisdiction on American soil, so the congressman’s inquiry about the case was better directed to the FBI.

The Galíndez case, in fact, was turning into a major source of friction between the two federal agencies. Hoover, who informed Attorney General Herbert Brownell Jr. that Galíndez had been a valued informant for the FBI, took his probable murder personally. Hoover was further enraged by the suspicious disappearance of young Gerald Murphy and the new round of embarrassing political fallout from the case. To make matters worse, the FBI soon tied John Frank to the crimes, a man who was not only a former bureau agent, but, like his boss, Maheu, was now part of the shadowy CIA orbit that operated serenely above the law. As was common when Hoover sought revenge in Washington’s political wars, he leaked much of the Galíndez story to the press. In late February, Lifemagazine ran a dramatic version of the affair under the headline “The Story of a Dark International Conspiracy.”

The Eisenhower Justice Department knew that despite the sensitive national security ramifications, someone had to take the fall in the sensational case, and John Frank was the obvious choice. But, as federal prosecutors began to build a case for conspiracy, kidnapping, and homicide against Frank, the CIA’s general counsel, Lawrence Houston, and Dulles himself huddled anxiously with the attorney general. Brownell assured the CIA that he would keep the case tightly held to avoid further press leaks because he realized that the affair involved “keen” national security interests. Brownell’s deputies grew frustrated as they tried to peel away the layers surrounding the case. In March 1957, Assistant Deputy Attorney General Warren Olney III complained in a memo to Brownell, “In my opinion the information given to you by CIA is vague and uncertain and does not resolve the question as to whether [Frank] has in fact been used in any capacity by CIA.” Olney recommended that the CIA “be requested directly and definitely” to state its exact relationship with the man at the center of the Galíndez mystery.

After intricate negotiations between the Justice Department and the CIA, John Frank was finally charged with an astonishingly light offense: failure to register as a foreign agent. “I fully appreciate that to indict a person involved in a possible murder and kidnapping for violation of the Registration Act is like hitting a man with a feather when he should be hit with a rock,” acknowledged one chagrinned Justice Department official. But considering the highly charged political atmosphere surrounding the case, he observed, it was the only way to ensure that “the subject will [not] escape scot-free.”

In December 1957, Frank was convicted of multiple counts of violating the Registration Act and sentenced to a maximum eight months to two years in federal prison. But the following year, his conviction was overturned by a federal appeals court in the District of Columbia that ruled that Frank had been denied a fair trial because of “the prosecutor’s attempt to connect him in the jury’s mind with the Galíndez-Murphy affair.” As he entered the second round of his legal battle, Frank made it clear that he was not going to be the fall guy for the CIA on the Galíndez case. Before his new trial began, Frank played his trump card, making it known that his line of defense would be that he had been working for U.S. intelligence throughout the affair. When Frank’s lawyer issued subpoenas for several CIA witnesses to appear in court, agency officials quickly moved to block them from testifying, thereby aborting the trial. The Justice Department was forced to strike a plea bargain with Frank, and in March 1959, he paid a modest fine, signed an agreement not to work as a foreign agent, and walked out of court a free man. Nobody was ever charged in the murders of Jesus de Galíndez or Gerald Murphy.

Allen Dulles’s CIA believed in the power of ideas. It was easy for Dulles’s Ivy League–educated executive team to understand why the Trujillo regime became so obsessed with a doctoral dissertation written by an obscure academic. They knew that ideas mattered: they floated like seeds on the wind, over mountains and seas, and took root in the most unexpected places. The Cold War was, in fact, a war of ideas, fought primarily in the realm of the symbolic, through propaganda campaigns and “proxy” conflicts, instead of on battlegrounds where the superpowers clashed head-to-head.

Joseph Stalin, too, understood the power of words, calling writers “the engineers of the human soul.” The Soviet leader had a way of expressing himself with industrial bluntness. “The production of souls,” he stated, “is more important than the production of tanks.” Stalin engineered a conformity of Soviet thought by executing writers, intellectuals, and artists who did not toe the party line, or by exiling them to the gulag’s frozen extremities.

The CIA’s methods of cultural engineering were far more subtle but no less effective. The agency spent an inestimable fortune on the war of ideas, subsidizing the intellectual and creative labors of those who were deemed politically correct and seeking to marginalize those who challenged the “crackpot realism” of Cold War orthodoxy. The main front organization used by the CIA to spread its largesse and influence was the Congress for Cultural Freedom, “a kind of cultural NATO,” in one critic’s words, founded in 1950 to counter the propaganda efforts of the Soviet bloc. The Congress for Cultural Freedom grew to become one of the biggest arts patrons in world history, sponsoring an impressive array of book publishing start-ups and literary magazines—including the influential Encounter and Paris Review—as well as art exhibits, literary prizes, concert tours, and international conferences held in Paris, Berlin, and the Rockefeller Foundation’s Bellagio retreat overlooking Lake Como.

There was a seductive appeal to the CIA’s cultural patronage, for it offered not only the satisfaction of doing one’s patriotic duty and resisting Stalinist tyranny, but also a comfortable reprieve from the financial anxieties of the freelance, creative life. “These stylish and expensive excursions must have been a great pleasure for the people who took them at government expense,” remarked Jason Epstein, former Random House editorial director and cofounder of The New York Review of Books. “But it was more than pleasure, because they were tasting power. Who wouldn’t like to be in a situation where you’re politically correct and at the same time well compensated for the position you’ve taken?”

Many leading artists and intellectuals fell into the ranks of the CIA’s generously funded culture war, including Arthur Schlesinger Jr., Mary McCarthy, Robert Lowell, Dwight Macdonald, Daniel Bell, Isaiah Berlin, George Plimpton, Peter Matthiessen, and Mark Rothko. But the recipients of CIA sponsorship paid a price: their intellectual independence. As historian Frances Stonor Saunders observed, “The individuals and institutions subsidized by the CIA were expected to perform as part . . . of a propaganda war.” Those who took agency funds became “cheerful robots” of the Cold War, in C. Wright Mills’s memorable phrase. Mills, one of the few prominent American scholars to actively resist the siren calls of the Cold War intelligentsia, was predictably attacked in these circles. While Mills was coming under fire in the pages of CIA-funded publications likeEncounter, he was embraced by leftist intellectuals in Europe such as Ralph Miliband (father of British Labour Party leader Ed Miliband) and historian Edward Thompson, who declared, “Wright is fortunate in his enemies.”

Mills was fortunate in other ways, too. His intellectual gifts and personal fortitude allowed him to carve out a prominent public position for himself, even at the height of Cold War conformity in America. But most of those who challenged the era’s mandatory spirit of American triumphalism soon found themselves intellectually isolated and professionally invisible. Under the reign of CIA-approved thought, unpleasant realities about the U.S. imperium were considered out-of-bounds for scholarly or journalistic exploration, including the bloody regime changes in Iran and Guatemala and the boiling cauldron of racial injustice at home. The grants, literary prizes, journalism awards, and academic endowments went to those who saw America as the hope of the world, not to those who focused on its deep flaws.

Those CIA-approved intellectuals who dared to assert their independence soon found that once-welcoming doors were closed to them. In 1958, Dwight Macdonald—a frequent intellectual sparring partner of his friend Mills—broke out of the Cold War thought bubble with a cranky article forEncounter titled “America, America,” in which he railed against the idiocy of the country’s mass culture. There was nothing particularly surprising about Macdonald’s highbrow lament about the spread of primitivism in pop culture. But the article was deemed unacceptable by the editors ofEncounter, and though Macdonald was a former editor of Encounter, the magazine refused to publish it.

Like many of the CIA-sponsored literary projects, Encounter reflected the aesthetics of James Jesus Angleton, the CIA’s unofficial cultural commissar. As a Yale undergraduate, Angleton had founded the avant-garde literary magazine Furioso and befriended Ezra Pound and e.e. cummings. The spy wizard was a devotee of the modernist school of poetry—particularly its high priest, T. S. Eliot—and the pages of Encounter were dominated by an Eliotic sensibility, though Eliot himself shunned the London-based publication as so “obviously published under American auspices.”

A new generation of Beat poets led by Allen Ginsberg was beginning to challenge the reign of literary modernism, invoking the lush populism and unabashed deviancy of Walt Whitman. As the Beats laid siege to Eisenhower-era cultural banality, the CIA-funded poetry establishment struggled to keep these barbarians outside the gates. Years later, Ginsberg imagined a confrontation between himself and Angleton’s favorite poet on the fantail of a boat in European waters. “What did you think of the dominance of poetics by the CIA?” Ginsberg asks Eliot. “After all, wasn’t Angleton your friend?” The old master admits he knew of the infamous spook’s “literary conspiracies” but insists they were “of no importance to Literature.” But Ginsberg passionately disagrees. The CIA, he tells Eliot, secretly funded a “whole field of Scholars of War” and “nourished the careers of too many square intellectuals,” thereby undermining efforts to “create an alternative free vital decentralized culture.” The result, as Ginsberg wrote in his 1956 masterpiece, Howl, was the unchallenged rise of the American Moloch, “vast stone of war . . . whose soul is electricity and banks,” and a culture that devoured the souls of its own children.

Angleton carried an elaborate portfolio at the CIA, from the politics of art to the metaphysics of assassination. In December 1954, Dulles officially named him chief of counterintelligence, the department tasked with blocking enemy penetration of the agency. But, in reality, his manifold duties were as hard to get a hold on as the smoke curling up from the chain of cigarettes he inhaled throughout the day. “I remember Jim as one of the most complex men I have ever known,” recalled Dick Helms, one of Angleton’s vital defenders and patrons within the agency. “One did not always have to agree with him to know that he possessed a unique grasp of secret operations. As a friend remarked, Jim had the ability to raise an operational discussion not only to a higher level but to another dimension. It is easy to mock this, but there was no one within the agency with whom I would rather have discussed a complex operational problem than Angleton.”

Angleton’s activities ranged from purloining documents at foreign embassies to opening the mail of American citizens (he once jocularly referred to himself as “the postmaster”) to wiretapping the bedrooms of CIA officials. It was his job to be suspicious of everybody, and he was, keeping a treasure trove of sensitive files and photos in the locked vault in his office. Each morning at CIA headquarters, Angleton would report to Dulles on the results of his “fishing expeditions,” as they called his electronic eavesdropping missions, which picked up everything from gossip on the Georgetown party circuit to Washington pillow talk.

As Dulles was well aware, Angleton had even tucked away explosive secrets about the CIA director himself. That is why Dulles had rewarded him with the most sensitive job in the agency, Angleton confided to journalist Joseph Trento near the end of his life. “You know how I got to be in charge of counterintelligence? I agreed not to polygraph or require detailed background checks on Allen Dulles and 60 of his closest friends. They were afraid that their own business dealings with Hitler’s pals would come out.”

Angleton’s selection as the top hunter of Soviet moles struck many in the agency as peculiar. During and after the war, Angleton had been badly fooled by his close chum in British intelligence, the legendary double agent Kim Philby. The witty, bibulous, stammering Philby, who had betrayed his class and country by secretly going to work for Soviet intelligence as a young Cambridge graduate in the 1930s, forged a tight friendship with Angleton in London during the war. Philby and the Anglophilic Angleton, who had attended the upper-crust British boarding school Malvern, renewed their relationship when Philby was posted to Washington, D.C., in 1949, as the British Secret Intelligence Service liaison. The two men shared long, sodden lunches at Harvey’s, a Washington power restaurant also favored by the likes of Hoover and his companion, Clyde Tolson.

Angleton’s children remembered the drunken nursery games played by Philby and his friends Guy Burgess and Donald Maclean, who belonged to the same secret ring of Cambridge-bred traitors, when they were invited to the Angleton home in Arlington for dinner. “They’d start chasing each other through the house in this little choo-choo train,” according to Siri Hari Angleton, the spymaster’s youngest daughter, “these men in their Eton ties, screaming and laughing!” At another raucous party, she recalled, “Philby’s wife passed out, and was just lying on the floor. Mummy said, ‘Oh, Kim, don’t you want to see how Mrs. Philby is doing?’ And he said, ‘Ahhh . . .’ and just stepped right over her to get another drink.”

Angleton struck people as a wispy figure of a man. He was known as the “Gray Ghost” in agency circles—a tall, stooped, ashen-faced figure, with a bony, clothes-rack frame, draped in elegant, European-tailored suits, and wreathed in his customary rings of smoke. But around Philby, Angleton seemed to come alive, to glow. They were boarding school boys again.

After Philby was finally exposed, ultimately fleeing to Russia, Angleton’s anti-Soviet sentiments hardened into a fundamentalism that clouded his judgment. “I have no doubt that the exposure of Kim Philby was lodged in the deepest recesses of Jim’s being,” Helms later commented. If he were the sort of chap who murdered people, Angleton told a friend in British intelligence, “I would kill Philby.” The betrayal was painfully intimate, and it bred a paranoia that bloomed darkly within Angleton. When he was named counterintelligence chief, he saw traitors and signs of Soviet treachery everywhere. His compulsive mole hunting ruined the careers of dozens of CIA agents, doing more to damage agency security than to fortify it. “I couldn’t find that we ever caught a spy under Jim,” said William Colby, the CIA director who finally terminated Angleton’s long tenure in 1975.

But under Dulles, Angleton enjoyed free rein to pursue his demons. He dreamed up Cold War phantasms and bogeymen, and then invented all-too-real methods of destroying these horrible apparitions. He operated a kind of virtual CIA within the CIA, reporting only to Dulles himself—and even the top spymaster was not fully aware of his murky activities. “My father once said, ‘I’m not a genius, but in intelligence I am a genius,’” recalled Siri Hari Angleton, who changed her name from Lucy as a young woman, after following her mother and older sister into the Sikh religion.

Dulles and Angleton went way back together, to the dark maze of postwar Rome. Like Helms, Dulles admired Angleton’s complex mind and the deep calculus of his spycraft. “Jim,” Dulles once told Angleton’s wife, Cicely, “is the apple of my eye.” Angleton, in turn, grew deeply fond of Dulles, whom he looked up to as a father figure, and of Clover Dulles, too, with whom he shared a creative temperament.

“Angleton was fascinating,” recalled Joan (Dulles) Talley. “My mother liked him a lot, he was very talkative, very intellectual. He was an odd one, he fussed over the orchids he grew—which I think was a wonderful obsession of his—and he drank too much. But he was lots of fun for anyone to talk to, you’d never know where the conversation was going to go. He’d jump from orchid colors to flyfishing to poetry and music. He was a real scholar, and he was an oddball. A totally unique creation.”

Angleton expressed an appreciation for Clover’s art, and he once begged her for a self-portrait that she had painted. Clover suspected that the aesthetic spy was “in his cups” when he made the request, but she agreed to give it to him, as she later told Joan, “because Jim labors day and night for CIA and Dad.” The two couples enjoyed each other’s company, and the Angletons were often invited for dinner at Q Street. Cicely Angleton came from a prosperous family that had made a fortune in Minnesota iron ore—and, educated at Vassar, she shared Clover’s interests in spirituality and the arts. Cicely later published several volumes of poetry, taking the creative path that her husband otherwise might have gone down.

Dulles and Angleton shared a disdain for Washington bureaucracy and for the governmental oversight that comes with a functioning democratic system. Later, in the post-Watergate ’70s, when the Church Committee opened its probe of CIA lawbreaking, Angleton was called to account for himself. As he completed his testimony, the Gray Ghost rose from his chair, and, thinking he was now off the record, muttered, “It is inconceivable that a secret intelligence arm of the government has to comply with all the overt orders of the government.” It was a concise articulation of the Angleton philosophy; in his mind, CIA overseers were a priestly caste that, because the fate of the nation had been placed in its hands, must be allowed to operate unfettered and above the law.

“Allen wasn’t red-tape and neither was daddy,” said Siri Hari. “You know, back then, people were much more interesting. . . . I don’t think it was a case of resenting bureaucracy, because the bureaucracy just never came that close to them anyway, so why would they resent it? They probably just felt, you know, a little beyond it, a little above it.”

Dulles entrusted Angleton with the agency’s most vital and sensitive missions. He was the principal CIA liaison with the key foreign intelligence services, including those in frontline Cold War nations like France, West Germany, Turkey, Taiwan, and Yugoslavia, as well as with Mossad, the Israeli spy agency. Angleton developed a special bond with the Israelis, forging a realpolitik relationship, with both parties conveniently overlooking Angleton’s role in the Nazi ratlines after the war. The Israelis maintained close ties to the American espionage oracle until the end of his life. Several members of Mossad came to Angleton’s home as he lay dying in the spring of 1987, to pay their last respects—and perhaps to make certain the vapory Gray Ghost was indeed finally leaving this mortal coil.

Dulles also put Angleton in charge of the CIA’s relationship with the FBI—a delicate task considering the rivalry between the two agencies. At the same time he was working with the federal bureau in charge of fighting organized crime, Angleton was also pursuing a CIA partnership with the Mafia. Angleton possessed one of those rare intellects—and characters—that allowed him to lead a life filled with contradiction. He easily passed back and forth between Washington’s overworld and the criminal underworld. He was the sort of man who could crossbreed a new orchid, cook a delicious pasta with slivered truffles imported from Ristorante Passetto in Rome, and then sit down with a criminal mastermind to discuss the fine points of murder. Though he dined and drank with Georgetown high society, Angleton’s work also brought him into close contact with the agency’s rougher characters, including Shef Edwards’s security cops, who helped install Angleton’s bugs, and Bill Harvey, the hard-drinking gun nut who figured prominently in a number of the agency’s assassination jobs.

It was all of a piece, in the intricately wired mind of Jim Angleton: countering dangerous ideas by publishing CIA-vetted literature, or by eliminating the intellectuals and leaders who expounded these ideas. One day, shortly after Fidel Castro took power in Havana, Angleton had a brainstorm. He summoned two Jewish CIA officers, including Sam Halpern, who had recently been assigned to the agency’s covert Cuba team. Angleton asked them to fly to Miami and meet with Meyer Lanksy, organized crime’s chief financial officer, who had been forced to flee Havana ahead of Castro’s revolutionaries, leaving behind the Mafia’s highly lucrative casino empire. Lansky was part of the Jewish mob but had close business ties to the Italian Mafia. Angleton told Halpern and the other Jewish CIA agent to see if they could convince Lansky to arrange for the assassination of Castro.

Angleton’s emissaries met with Lansky, but the crime mogul drove too hard a bargain for his services and the deal fell through. This was only the beginning of the CIA’s endless, Ahab-like quest to kill the Caribbean leviathan, however. Castro would never stop haunting the dreams of the CIA high command. The Cuban revolutionary was not only intellectually formidable and politically fearless; his dream of national liberation was backed up with guns. Castro and his equally charismatic comrade, Che Guevara, made it clear from the start that they would not share the fate of Jacobo Arbenz in Guatemala: they would fight fire with fire. Che, a twenty-five-year-old doctor and adventurer in search of a grander meaning to his life, was living in Guatemala City when Arbenz was overthrown. He saw what happened when Arbenz’s moderate reforms came up against the imperial force of United Fruit and the CIA.

“I am not Christ or a philanthropist, old lady,” Che wrote to his mother, Celia, in the bantering style he had developed with her, as he and Fidel prepared to board the leaky yacht Granma in Mexico with their band of guerrillas to make history in Cuba. “I fight for the things I believe in, with all the weapons at my disposal and try to leave the other man dead so that I don’t get nailed to a cross.”

To avoid Arbenz’s fate, Castro and Guevara would do everything he had not: put the hard-core thugs of the old regime up against a wall, run the CIA’s agents out of the country, purge the armed forces, and mobilize the Cuban people. By militarizing their dream, Fidel and Che became an audacious threat to the American empire. They represented the most dangerous revolutionary idea of all—the one that refused to be crushed.

It was after midnight, on September 20, 1960, when Fidel Castro came uptown to Harlem. The white, terra-cotta facade of the Hotel Theresa on Seventh Avenue and West 125th Street—“the Waldorf of Harlem”—gleamed under a battery of police spotlights as brightly as a Hollywood movie premiere. Outside the hotel entrance, a boisterous crowd was steadily growing, in defiance of the pelting rain and the intimidating phalanx of policemen, awaiting the international political celebrity who was rumored to be checking in. Suddenly a lusty roar went up from the throng as an official-looking car suddenly glided to a stop outside the hotel and the familiar, tall, bearded figure emerged from the vehicle. “Cuba si, Yanqui no!” shouted the crowd as a beaming Castro swept his arms through the air, before being hustled into the hotel.

The Cuban leader and his fifty-member delegation, who were in New York for the annual United Nations General Assembly meeting, had not received such a warm welcome at their first choice of accommodations, the midtown Shelburne Hotel. When the Cuban delegation checked in two days earlier at the Shelburne, they were greeted by a militant group of anti-Castro exiles calling itself La Rosa Blanca (The White Rose), which threatened to blow up the hotel. The Shelburne management promptly informed Castro’s party that they would need to put up a $20,000 security deposit, and an outraged Fidel, insisting that his government did not have ready access to that kind of cash, announced that they would leave the hotel and pitch tents outside the UN if necessary.

Castro’s 1960 trip to New York marked a sharp turning point in U.S.-Cuba relations. The previous year, in April 1959, the Cuban leader had enjoyed a much more hospitable reception during his eleven-day visit to the United States. Fresh from his revolutionary victory on New Year’s Eve, Fidel was still something of a political mystery to the Eisenhower administration, and the media embraced him as the silver-tongued conqueror who had liberated the Cuban people from Fulgencio Batista’s gangster reign. During his earlier visit to New York—a city he loved—Fidel roamed the streets followed by packs of reporters and photographers, dropping by a Queens elementary school, where the children all wore cardboard cut-out beards in his honor, and the Bronx Zoo, where he gulped down a hot dog and an ice cream cone, and alarmed zoo guards by sticking his hand through the bars of a cage to pat the cheek of a Bengal tiger. “This is like prison—I have been in prison, too,” said Fidel, who had survived Batista’s cages. Even the CIA seemed charmed by Castro during his 1959 visit. After meeting with the Cuban leader in his New York hotel suite, an ecstatic CIA agent reported, “Castro is not only not a Communist, but he is a strong anti-communist fighter.”

But there had been many changes over the following year, as Castro moved to deliver on the promise of the revolution, nationalizing the sugar and oil industries, and beginning to transform Cuba from a vassal state of the United States to a sovereign nation. By early 1960, Dulles had resolved the debate within his intelligence agency over Castro’s true identity, deciding that he was a dedicated Communist and a serious threat to U.S. security. The CIA director’s hardening line mirrored that of friends in the business world like William Pawley, the globetrotting entrepreneur whose major investments in Cuban sugar plantations and Havana’s municipal transportation system were wiped out by Castro’s revolution. One of a coterie of vigorously anti-Communist international businessmen who provided the CIA with foreign information and contacts, as well as guns and money, Pawley began lobbying the Eisenhower administration to take an aggressive stand against Castro when he was still fighting Batista’s soldiers in the rugged peaks of the Sierra Maestra. After Fidel rode into Havana on a tank in January 1959, Pawley, who was gripped by what Eisenhower called a “pathological hatred for Castro,” even volunteered to pay for his assassination. As the Eisenhower administration took an increasingly belligerent posture toward the Castro regime, Pawley found himself at the center of the action, boasting that he was “in daily touch with Allen Dulles.”

The Eisenhower administration responded to Castro’s expropriation of American-owned plantations, factories, and utilities by cutting imports of Cuban sugar—the country’s economic lifeblood—and by launching a secret campaign aimed at sabotaging Castro’s government. In February 1960, mercenary pilots hired by the CIA dropped bombs on Cuban sugar mills, and in March, a French freighter loaded with Belgian weapons was blown up in the Havana harbor, killing dozens of sailors and stevedores. A second explosion killed many more, including firefighters and emergency medical workers, as they rushed to the scene. The same month, President Eisenhower approved a plan to train a paramilitary force outside of Cuba for a future invasion of the island. The operation, which was spearheaded by Vice President Nixon and the CIA, would culminate the following year on the beaches of the Bay of Pigs.

The explosion in Havana’s harbor was a milestone in the Cuban revolution. At a funeral ceremony the next day at Colon cemetery, an emotional Castro vowed that “Cuba will never become cowardly” in the face of U.S. aggression. He ended his oration with the declaration that became a ringing slogan of the Cuban revolution: Patrio o Muerte, Venceremos! (Motherland or Death, We Shall Win!) Determined that Cuba would not become another Guatemala, Castro turned to the Soviet Union for economic and military aid, and the tragic dance began, locking Cuba, the United States, and Russia in a fateful embrace for years to come, and nearly ending in a nuclear inferno.

When Castro and his retinue landed at New York’s Idlewild Airport on September 18, 1960, he appeared to be in a “subdued mood,” reported The New York Times, for reasons that were not yet known to the American people. The Cuban airliner that flew the delegation to the United States had to be immediately refueled and flown back to Havana, to avoid being impounded, as a result of legal claims against the revolutionary government by U.S. business interests. It was just one of the numerous ways that Castro’s delegation was subjected to harassment during his weeklong visit to New York, as the Eisenhower administration maneuvered against the Cuban leader on multiple fronts. By the time his retinue was forced out of the Shelburne Hotel, Castro seemed persona non grata in New York. The State Department had ruled that the Cubans could not leave Manhattan, and no city hotel was willing to accommodate them. If New York was incapable of providing hospitality to world leaders, Castro fumed, perhaps the UN should be moved to another city, such as Havana.

But then Castro turned his humiliation into a propaganda triumph. As the Cuban delegation was preparing to leave the Shelburne, a political sympathizer put them in touch with Black Muslim leader Malcolm X, who intervened on their behalf with the operators of Hotel Theresa. The tallest building in Harlem, the thirteen-story hotel was a lofty—if somewhat worn-down—landmark in the black community. In its heyday, the Theresa had accommodated a glittering array of African American celebrities when they were not welcome at New York’s downtown hotels, including Josephine Baker, Louis Armstrong, Duke Ellington, Nat King Cole, and Lena Horne. In June 1938, Joe Louis celebrated his heavyweight championship victory over Max Schmeling, Nazi Germany’s great white hope, at the Theresa, as thousands of fans cheered on the streets outside.

When word spread that the Cuban delegation was headed uptown, Love B. Woods, manager of the Theresa, immediately came under the same political pressures as other New York hotel operators. Even Harlem’s outspoken congressman, Adam Clayton Powell Jr., opposed Castro’s relocation to Harlem, calling it “a publicity stunt.” Powell told reporters, “We Negro people have enough problems of our own without the additional burden of Dr. Castro’s confusion.” But Woods, an elderly and unruffled man who had grown up in Jim Crow South Carolina, knew what it was like to be denied a roof over your head. Woods stood his ground and opened the doors of Harlem’s finest hotel to the Castro delegation. “We don’t discriminate against anybody,” he said.

Other prominent figures in Harlem also stuck out their necks for Castro. Knowing that Woods might have trouble cashing the Cubans’ check because of the rising political tensions between the two countries, a Harlem attorney named Conrad Lynn arranged to have a local gambling kingpin put up $1,000 in cash to cover the delegation’s hotel costs. The gangster was not “a communist or politically developed,” Lynn recalled, “but something told me that this was a man, and that he wanted to help. And he did.”

Young Harlem activists also rallied around Castro, like Preston Wilcox, who was among those cheering the Cuban leader outside the Theresa. Wilcox saw a “spiritual connection” between Fidel’s decision to come to Harlem and the rising dynamism of the civil rights movement. He noted the color division between the opposing lines of Cubans in the crowd: the black Cubans were pro-Castro, while those loudly denouncing him were lighter-shaded. Whenever Juan Almeida, Castro’s black military commander and a hero of the revolution, left the hotel during the delegation’s stay and went strolling through the neighborhood, enthusiastic crowds swirled around him. The New York Citizen-Call, an African American newspaper, commented, “To Harlem’s oppressed ghetto dwellers, Castro was that bearded revolutionary who . . . had told white America to go to hell.”

Harlem’s show of hospitality for Castro turned out to be a public relations disaster for the Eisenhower administration. By moving to Harlem, the Cuban leader not only shamed the U.S. government for its lack of manners but focused a sharp spotlight on the nation’s seething racial tensions. Some of the city’s finest hotels suddenly offered entire floors to the Cuban delegation, free of charge, but Castro refused to move. When world leaders—including Khrushchev, Nasser, and Nehru—began coming uptown to meet with Castro, with TV camera crews close behind, Washington’s embarrassment only grew.

Castro’s mastery of the media game was on full display during his Harlem sojourn. After Eisenhower snubbed him by not inviting him to an official reception for Latin leaders, the Cuban premier responded by inviting Theresa’s all-black staff to a steak dinner in the hotel banquet room with him and the popular Almeida. When articles suddenly began appearing in New York newspapers, alleging that the Theresa was overrun with hookers, Fidel again parried the propaganda thrust, declaring in his speech at the UN, “They began spreading the news all over the world that the Cuban delegation had lodged in a brothel. For some, a humble hotel in Harlem, a hotel inhabited by Negroes of the United States, must obviously be a brothel.”

By the time he delivered his speech before the UN General Assembly on September 26, Castro had seized the moral high ground in his growing war of words with Washington. His UN speech, a marathon performance that stretched for over four hours, was a passionate defense of Cuba’s autonomy. For years, his colonized nation had no voice in world affairs, Castro told the international assembly. “Colonies do not speak. Colonies are not recognized in the world. That is why our [nation] and its problems were unknown to the rest of the world. . . . There was no independent republic; there was only a colony where orders were given by the ambassador of the United States.” But now, at long last, Castro was giving Cuba a full-throated voice.

What had his small, impoverished nation done to so offend its powerful neighbor, asked Castro? “We instituted an agrarian reform that would solve the problems of the landless peasants, that would solve the problem of the lack of basic foodstuffs, that would solve the great unemployment problem on the land, that would end, once and for all, the ghastly misery which existed in the rural areas of our country.

“Was it radical?” asked Castro, with the rhetorical skill he had mastered as a young lawyer, when his own life was on the line in Batista’s courtrooms. “It was not very radical. . . . We were not 150 percent communists at the time. We just appeared slightly pink. We were not confiscating lands. We simply proposed to pay for them in 20 years, and the only way we could afford to pay for them was by bonds—bonds which would mature in twenty years, at 4.5 percent interest, which would accumulate annually.” See, Castro was telling the world, revolutionary Cuba had been willing to play by capitalist rules. But this was not enough for Washington. Cuba’s new government “had been too bold. It had clashed with the international mining trusts, it had clashed with the interests of United Fruit Company, and it had clashed with the most powerful interests of the United States. So then the example shown by the Cuban revolution had to receive its punishment. Punitive actions of every type—even the destruction of Cuba’s foolhardy people—had to be carried out against the audacity of the revolutionary government.”

Journalist I. F. Stone pronounced Castro’s oration—which he delivered, hour after hour, by consulting just a single page of notes—a “tour de force.” It was unlike anything ever heard before in the United Nations: a scholarly, eloquent, and heartfelt broadside against the arrogance of imperial power, delivered in the capital of world finance, by a charismatic rebel leader who had risked his life to challenge that power. If Allen Dulles’s imperial guard still had any doubts about how serious a threat Fidel Castro represented, his dramatic performance at the UN that day thoroughly dispelled them.

The CIA knew how seductive Fidel’s appeal was—even in the West, particularly among college students, intellectuals, and artists. In April 1960, Robert Taber—the first African American reporter for CBS News, who had scored an exclusive interview with Castro when he was still fighting in the mountains—stirred liberal circles by purchasing a full-page ad in The New York Times that passionately endorsed the Cuban revolution. The appeal was signed by an impressive list of literary names—including Jean-Paul Sartre, Simone de Beauvoir, Norman Mailer, James Baldwin, and Truman Capote—and sparked a wave of popular interest in the Cuban cause that led to the formation of the Fair Play for Cuba Committee (FPCC). Within six months, the committee had enrolled seven thousand members in twenty-seven “adult chapters” across the country and had struck a chord on college campuses, where forty student councils were formed.

While Castro was staying at the Theresa, the FPCC organized a party in his honor in the hotel’s shabby ballroom. Among the guests were Allen Ginsberg, Langston Hughes, and C. Wright Mills, whose own impassioned defense of the Cuban revolution, Listen, Yankee, had sold four hundred thousand copies within months. Mills’s book was based on his brief tour of the island, including three eighteen-hour days in the indefatigable company of Fidel, a man who, in the words of his friend Gabriel García Márquez, was “addicted to the habit of conversation . . . he rests by talking.”

These were the early, honeymoon days of the revolution, before Castro’s caudillo tendencies had hardened, and before the Soviet “partnership” with Cuba had become its own kind of colonialism. The relentless U.S. pressure on the island would never succeed in toppling Castro, but it would help turn his nation into the tropical police state that CIA propagandists insisted it was from the very beginning, amounting to a victory of sorts for Washington hard-liners.

But there was still a glow around Castro as he and his retinue settled into the Hotel Theresa. It was the dawn of the 1960s, the gray Eisenhower-Dulles reign was coming to an end, and the world seemed to shimmer with new possibilities. The most electric moment of Castro’s week in Harlem came one evening when Malcolm X—wearing a long, double-breasted, black leather coat and tie—swept past the press pack in the hotel lobby and was whisked to Fidel’s suite on the ninth floor. Fidel invited Malcolm to sit next to him on the bed, the only comfortable oasis in a room thick with cigar smoke and crowded with aides, bodyguards, and a few specially selected members of the African American press. The two revolutionary icons seemed hesitant with each other at first, their communication made precarious by their language differences. But as Castro plunged ahead with his uncertain English, they slowly found common ground. Fidel told Malcolm that the Cubans appreciated the warm reception given them in Harlem. “I think you will find the people in Harlem are not so addicted to the propaganda they dish out downtown,” Malcolm replied.

Castro’s young foreign minister, Raúl Roa Kourí, later said that he thought the meeting between the two revolutionaries, though lasting only a half hour, turned out to be historically significant because it helped broaden the Black Muslim leader’s narrow racial parameters. Malcolm began to understand that blacks were not the only poor and oppressed group, said Kourí, “and the struggle of all was a common struggle.” Afterward, Malcolm maintained a strong interest in the Cuban revolution, saying, “The only white person that I have really liked was Fidel.” He planned to visit Cuba but never had the chance.

The meeting between Fidel and Malcolm sent shudders through U.S. security circles, where a potential alliance between the Cuban revolutionary and the militant black nationalist was seen as the stuff of nightmares. Malcolm’s broadening political outlook, which accelerated after his split with the Nation of Islam in 1964, made him an increasingly dangerous figure—and Kourí, among others, was convinced that it led to his assassination in 1965. By 1960, Malcolm was the target of intensive FBI surveillance. In fact, one of the people who had squeezed into Castro’s hotel bedroom that evening was an undercover FBI agent, who later reported back to the bureau on the two men’s conversation. According to a confidential FBI memo based on the source’s report, Malcolm told Fidel that he was predisposed to like him, because “usually when one sees a man whom the United States is against, there is something good in that man.”

By the time Castro came to Harlem, he, too, was the target of increasingly ominous U.S. intelligence scrutiny. Just days before the Cuban delegation checked into Hotel Theresa, Bob Maheu—on orders of the CIA—met at another Manhattan hotel with Johnny Rosselli, the handsome, silver-haired Mafia lord who presided over the underworld’s Las Vegas empire, to develop a plan to assassinate Castro. Maheu and Rosselli were joined at the Plaza Hotel meeting by Jim O’Connell, Maheu’s handler in the CIA security office. O’Connell posed as an American businessman who had been dispossessed by Castro’s revolution and was willing to pay for his elimination. But the savvy Rosselli was not fooled: he quickly figured out that the Mafia was being recruited for a top secret government assignment.

Once again, Bob Maheu found himself at the center of a lethal CIA operation. Near the end of his life, he recalled what he went through when the CIA asked him to serve as the main emissary with the Mafia in the Castro assassination plot. Sitting with two visitors in his ranch house on the edge of a Las Vegas golf course, sipping vodka on the rocks as golf balls periodically clunked off the roof, Maheu recounted a long night of soul-searching as he wrestled with the CIA request. Shef Edwards and Jim O’Connell framed their pitch to Maheu in terms a good Catholic would understand—killing Castro was an act of “just war,” they said; it would save thousands of lives. They made it clear that the execution order came from the top of the agency, from Old Man Dulles himself. Nonetheless, Maheu realized that he would “have blood on [his] hands.”

To ponder the morally difficult question, Maheu went down to the recreation room in the basement of his Virginia home, where he made all of his big decisions, and listened all night long to classical music on the state-of-the-art sound system that the CIA had installed for him. In conversation with his visitors years later, Maheu tried to make it seem like his decision was a tortured process. But it actually sounded like a relative no-brainer for the security contractor. The CIA had made Bob Maheu’s career—he owed everything to the agency, even the extravagant stereo system that made his Bach and Glenn Miller records sound like they were “coming out of everywhere, even the waste paper baskets.” He wasn’t about to give it all up to spare the life of a bearded, bombastic Cuban revolutionary. Maheu told the CIA yes. When it came down to it, he didn’t mind having Castro’s blood on his hands, or that of his brother Raúl Castro and Che Guevara, for that matter.

It was the beginning of a long U.S. intelligence campaign to kill the Cuban leader, stretching over several presidencies and involving untold numbers of accomplices—including mobsters, soldiers of fortune, disaffected members of the Havana regime, and security contractors like Maheu.

As Castro prepared to return home at the end of his tumultuous week in New York, he gave a spirited press conference at the airport. Why was the Cuban delegation departing on a Soviet jet, a reporter shouted? Because the United States had impounded all of Cuba’s airliners as a result of claims against his government, he responded. “What do you want us to do?” Castro asked plaintively. “You leave us without petroleum—Khrushchev gives us petroleum. You [cut] our sugar [imports]—Khrushchev buys our sugar. . . . You take away our planes—Khrushchev gives us his plane.”

The CIA knew what it wanted Castro to do. Shortly after the Cuban leader arrived home in Havana, as he addressed a teeming crowd from the balcony of the Presidential Palace, a bomb went off in the park behind the palace, followed by a second explosion within the hour. Later in the day, a third bomb—more powerful than the other two—rocked Havana. The CIA-sponsored terror campaign aimed at killing Castro and destroying his government was quickly escalating.

Two weeks after Fidel Castro checked out of the Hotel Theresa, another young dynamo made an appearance at the hotel. On the afternoon of October 12, 1960, Senator John F. Kennedy brought his presidential campaign to Harlem, speaking to a large crowd from a platform erected in front of the hotel. Kennedy was well aware that Castro had just put the Harlem hotel on the world map. JFK was fascinated by the charismatic Cuban, whose biography bore some resemblance to his own. Both men were the products of Catholic immigrant families who had worked their way up to wealth and success (Castro’s father had immigrated from Spain); both were the second sons of shrewd, entrepreneurial fathers and devout mothers; both were educated at elite schools; and both had rejected their class privilege, dedicating themselves to improving the lives of those less fortunate and to making their countries beacons of change.

After Castro’s triumph over Batista, Kennedy had warm words for the victorious revolutionary, declaring, “Fidel Castro is part of the legacy of Bolivar, who led his men over the Andes Mountains vowing ‘war to the death’ against Spanish rule.” The young senator criticized the Eisenhower administration for not giving Castro a more friendly greeting “in his hour of triumph” when he visited Washington in April 1959.

But during the presidential campaign, Kennedy, determined not to be tarred by Nixon as soft on the global Communist threat, carved out a position on Cuba that was even more militant than the Republican candidate’s, declaring that Castro had “betrayed the ideals of the Cuban revolution” and calling his regime “a Communist menace that has been permitted to arise under our very noses, only 90 miles from our shores.” Kennedy went so far as to suggest that the United States should take decisive action to remove the threat. His militant campaign rhetoric evoked a heated response from Castro during his epic UN speech, who called JFK an “illiterate and ignorant millionaire” with no understanding of Cuba’s plight.

In truth, Kennedy was keenly aware of Cuba’s colonial history and was outspokenly critical of how U.S. business interests had despoiled the country. In the same campaign speech in which he attacked Castro as a “dangerous enemy on our very doorstep,” JFK ripped into America’s corporate plunder and political domination of the island in surprisingly unvarnished terms. He also denounced Washington’s shameful practice of “propping up dictators throughout Latin America,” including the “bloody and repressive” Batista.

Kennedy’s campaign rhetoric on Cuba revealed a man who was painstakingly trying to work out the correct position for himself—and his country—on the revolutionary convulsions that were shaking the world. He did not want to appear naïve about Communist exploitation of these national liberation movements. But he was even more concerned that the United States be on the right side of history, by supporting the aspirations of the peoples of Latin America, Africa, and Asia as they threw off their colonial shackles.

On that brisk fall day outside the Hotel Theresa, where Kennedy was joined on the platform by a formidable supporting cast of Democratic dignitaries, including Eleanor Roosevelt and Congressman Powell, the presidential contender sounded more like a supporter of the bearded revolutionary in whose wake he was following than an enemy. “I am happy to come to this hotel, a little late, but I am happy to come here,” he began, to loud applause from the crowd. “Behind the fact of Castro coming to this hotel, Khrushchev coming to Castro, there is another great traveler in the world, and that is the travel of a world revolution, a world in turmoil. I am delighted to come to Harlem and I think the whole world should come here and the whole world should recognize that we all live right next to each other, whether here in Harlem or on the other side of the globe. We should be glad [that Castro and Khrushchev] came to the United States. We should not fear the twentieth century, for the worldwide revolution which we see all around us is part of the original American revolution.”

The man who was soon to become America’s youngest elected president showed Harlem that day that he, too, could deliver a speech—perhaps with less fire than Castro, but with equal passion and vision, and a bit more wit. Declaring that America’s revolutionary ideals continued to inspire people throughout the world, Kennedy said, “There are children in Africa called George Washington. There are children in Africa called Thomas Jefferson. There are none called Lenin or Trotsky or Stalin in the Congo . . . or Nixon. There may be a couple called Adam Powell,” he added, to loud laughter from the audience, which was well aware of the congressman’s reputation for womanizing.

America could not continue to inspire the world, Kennedy went on, unless it “practiced what it preaches” at home. “If a Negro baby is born here and a white baby is born next door, the Negro baby’s chance of finishing high school is about 60 percent of the white baby. This baby’s chance of getting through college is about a third of that baby’s. His chance of being unemployed is four times that baby’s.” All that must change, JFK told the audience. “White people are a minority in the world,” he said. They could no longer hold back the dreams of the rest of the world. Kennedy vowed that if he were elected, he would align America with the winds of change. “I believe it is important that the president of the United States personify the ideals of our society, speak out on this, associate ourselves with the great fight for equality.”

In the next three years, as Cuba became the flaming focal point of U.S. foreign policy, Kennedy would continue to wrestle with his relationship to Castro and the revolutionary change that he represented. As president, JFK’s posture on Cuba gradually softened, with the White House inching awkwardly toward a state of peaceful coexistence with the neighbor whom Kennedy once called “dangerous.” The fitful process of rapprochement with Cuba would set off a turbulent reaction in Washington, particularly within the national security circles still dominated by Dulles hard-liners. In these men’s minds, it was not just Havana that loomed as a hotbed of dangerous ideas, it was the Kennedy White House.

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