BETTER THAN US
I confess that many times I have meditated on the dramatic story of John F. Kennedy.
It was my fate to live through the era when he was the greatest and most dangerous adversary of the Revolution.
—Fidel Castro, April 24, 2009
WE SPOKE SOFTLY, SEATED AT A CORNER TABLE IN A RESTAURANT a few miles from CIA headquarters in the northern Virginia hamlet of Langley. My friend had retired several years earlier, but I still considered him the foremost Agency expert on Fidel Castro’s remarkable intelligence services. I was seeking insights and anecdotes, stories of success and failure in the CIA’s decades of jousting with Cuban spies. But my old colleague, a classically trained operations officer, was uncomfortable talking about his work. So, I wasn’t prepared for what he eventually volunteered, sheepishly to be sure: “I believe the Cubans have the best intelligence service in the world.”
Since then, I have heard variations of that judgment from other qualified intelligence veterans more times than I can remember. Many retired CIA officials stand in awe of how Cuba, a small island nation, could have built up such exceptional clandestine capabilities and run so many successful operations against American targets. As another CIA officer told me, “Boy, did they do a job on us!”
Current and former FBI officers agree. They share a grudging admiration for Cuban intelligence and the ease with which it burrowed spies and moles and agents of influence into significant American institutions. A former FBI officer who tracked Cuban intelligence told me, “They outperformed us by any objective measure.” Indeed, for years they ran circles around both the Agency and the Bureau.
The Cubans were underestimated for more than a quarter of a century. From New Year’s Day in 1959, when Castro won power, until the summer of 1987, they were viewed as bush-league amateurs, Latino lightweights in the conspiratorial sweepstakes of superpower espionage. And that was exactly the way the cunning Cubans wanted to be perceived. It allowed them to work clandestinely, in the shadows, largely beyond the sight and even the cognizance of their American adversaries.
Another American intelligence official who worked against the Cubans in the 1970s and 1980s admitted to me: “We just didn’t think we needed to be that good against them, but we did. They were better than us. In truth, we lost during most of the Cold War to the Cubans.”
They simply were not taken seriously. After all, as the thinking went at CIA, how could an impoverished third-world country—a Caribbean one at that, and in the grips of a chaotic revolution—possibly compete with the best intelligence service in the world? The fun-loving Cubans would not make good spies or spy-masters. They had no experience in espionage or international intrigue and, until Castro took power, Cuba had never run a foreign intelligence service. His neophyte spies had to learn the complex, rarefied world of intelligence tradecraft from scratch. Surely they would need many years to acquire real competence. Or so the Americans believed.
The reality was different. The General Directorate of Intelligence, or DGI, and other Cuban intelligence and security services got up and running in record time. Like besieged Israel following its independence in 1948, Castro and his communist revolution—under mortal threat from the United States during the early 1960s—developed a foreign intelligence service that quickly rose into the ranks of the half dozen best in the world. And in some covert specialties, particularly in the running of double agents and counterintelligence, my friend was right: For decades Cuba’s achievements have been unparalleled. There, as in Israel, the government knew that perfecting undercover capabilities, for both offensive and defensive purposes, would be essential for survival.
Yet for about three decades Washington remained ignorant of Cuban capabilities. A document prepared in the CIA in the 1960s and recently declassified highlights the foolishly patronizing attitudes of an Agency officer involved in Cuba operations. “Cubans generally constitute very poor agent material,” the anonymous author concluded. “They do not know the meaning of security. They do not take orders well, and the lonesome courage required for espionage is rarely part of their make-up. They make good fighters but poor spies.”1
It would not be until June 1987 that the Agency finally came to rue such self-defeating nonsense. It was on the first Saturday of that month when Florentino Aspillaga Lombard, the most informed and highly decorated officer ever to defect from Cuban intelligence, thrust himself into CIA hands through the American embassy in Vienna.
In 1985 he had been honored by the Cuban leadership as “intelligence officer of the year.” He was so consistently good that a year later he was runner-up for that award. He had also once received a handwritten commendation from Fidel, a rare honor few others experienced. He had to keep it locked in a safe, however, because the document was classified Muy Secreto, Top Secret. It singled him out for the crucial role he had played in July 1979 helping to ensure the military victory of the Marxist Sandinista guerrillas in Nicaragua. Fidel did not want the extent of Cuba’s role in that intervention to be known beyond Cuban military and intelligence circles.
Aspillaga had spent much of his earlier career in the DGI’s sister service in the Ministry of Interior, the even more obscure General Directorate of Counter-intelligence, the DGCI, known on the island as Contra Inteligencia. His last assignment was as the commanding DGI officer—the Center chief—in Bratislava, in what was then communist Czechoslovakia. He went there late in 1986 under light cover as a Cuban trading company official but was actually in charge of all intelligence and counterintelligence. He was the only DGI officer in that region, now the nation of Slovakia, handling all the Cuban agents operating from there and conducting counterintelligence operations across the border in Austria. He also had monitoring responsibility for the four thousand Cuban workers toiling in local factories as restitution for the economic subsidies Cuba received from Czechoslovakia.
Although no one in the DGI ever doubted Aspillaga’s loyalty, he had been seriously contemplating defection intermittently since the late 1960s. He is not certain when those subversive thoughts of flight first developed or what provoked them. But as James Angleton, for decades the paranoiac head of the CIA’s powerful Counterintelligence Staff (CI) and an expert on moles and defectors, once observed—long before anyone heard of computer viruses: “You never know when a worm goes into someone’s head.”2
None of the motives that typically move defectors seem to have applied in Aspillaga’s case. He was at the top of his form, respected and honored. Barely forty when he switched sides, he already held the rank of major—comandante— and was all but assured of further promotions. He had been a member of the Communist Party and its Marxist predecessor organizations since he was twenty. He had suffered no personal humiliation, was not an alcoholic or seeking fame or fortune. He had not stolen from his service, and suffered from no financial problems. He does not speak of any bolt-from-the-blue realization that instantly turned him against Castro or communism. He loved Marta Plasencia, a beautiful young Cuban woman working in one of the Slovak factories, and he took her with him when he defected, but she was not why he decided to flee. He could have divorced his wife—also a DGI officer—and married Marta in Bratislava.
There were precipitating events, however, “push” and “pull” factors that motivated him to commit treason. A few weeks before Aspillaga’s run across the Austrian border, Rafael del Pino, a two-star general and one of Cuba’s most decorated military officers, defected by flying a military Cessna to Key West. He was the highest-ranking Cuban military officer ever to seek asylum in the United States. Aspillaga admired this aviator hero and was moved to emulate him.
And, to the CIA’s enduring credit, Aspillaga told me of another reason for his decision. It may in fact have been the most compelling motive. He had greatly admired from a distance an Agency officer—handsome and dashing, and deeply involved in covert Cuba operations. Aspillaga told me that when he was in Havana running counterintelligence operations against the Agency, he had regularly observed this man, whose identity cannot be revealed here.
American intelligence officers played a similar role in unknowingly inducing at least one other high-level Cuban defection. A second former DGI officer I have interviewed extensively told me that he decided to leave communist Cuba because he also admired individual CIA officers. Another dozen defectors from Castro’s intelligence and security services who are quoted or cited here fled for a variety of other reasons. For nearly all of them, however, a slowly nurtured hatred of the oppressive communist system, a coalescing fear and loathing of Fidel Castro, and admiration for American freedoms and opportunities were the “worms” wriggling in their heads. Two have settled in Paris, others in Latin America, but the United States—though not necessarily the Cuban exile mecca of South Florida— is the preferred destination for nearly all the rest.
For the complex and brooding Aspillaga, there were still more reasons for his defection. Slowly, during the many years he served Fidel, he was being alienated by his narcissistic commander in chief. A jolting experience occurred in 1977 in Angola, on the west coast of Africa. Aspillaga was present one night at a Cuban military base near Luanda, the Angolan capital, when Fidel arrived, strutting and preening like a conquering Roman legionnaire. It was in fact a triumphal moment worthy of celebration: Two years earlier, Cuban intelligence and military forces had played the decisive role in assuring the victory and rise to power there of an allied Marxist revolutionary movement. The Cubans had fought and defeated powerful South African military forces and put down a coup against the leader they had secured in power. The lengthy intervention had been a heroic and dangerous undertaking thousands of miles from home.
Castro delivered a speech late that night to hundreds of his military and intelligence officers, all standing before him in uniform and at attention. Aspillaga recalls being in the front echelon, no more than twenty or thirty feet from his commander in chief. Fidel was exhausted after traveling several thousand miles by air. Fatigue might explain why he said things he would never want on the public record.
He was euphoric, glorying in what he had accomplished in Angola and elsewhere in Africa and other Cold War conflict zones. The speech was all about his triumphs, his valor, his audacity, his exceptional leadership qualities. He said almost nothing about the contributions of the uniformed men arrayed before him or the sacrifices of the many Cuban dead. Aspillaga was repulsed; it was the first time he had been in Castro’s presence. He told me Fidel compared himself to the Nazi propaganda chieftain Joseph Goebbels: “Castro said he could lead the multitudes better than Goebbels. That’s how he said it . . . how to guide people to do what you want them to do.” It was fidelista hubris in the most heinous extreme. “I knew he was evil,” Aspillaga said. “I told myself, this man is crazy.” It was the first staggering blow to the unqualified loyalty Aspillaga had felt for Fidel and the revolution since childhood.
Personality factors no doubt also influenced the decision to defect. Like so many of his former colleagues—indeed, like the best intelligence officers anywhere—he is strong spirited, adventurous, iconoclastic, and inclined to risk taking. So, perhaps, like not a few defectors, he was drawn to the danger of the act, the sheer excitement of switching sides and running the gauntlet to get there: a moth drawn to a flame. That morning when he made the fateful decision to seek out the CIA in Austria, he knew that a death sentence would be imposed on him in absentia. And because of the extraordinary and sensitive secrets he would share with his new American friends, he had no illusions that he would ever receive a reprieve from Fidel.
Aspillaga was in his early sixties when we sat down together on three different occasions in safe, out-of-the-way places, talking in extended recorded conversations. I was impressed with his intensity, religious convictions, and exceptionally good memory. He was always loquacious and cheerful, although, like most defectors uprooted from their countries, I knew he also suffered bouts of emotional turmoil.
He asked nothing of me in exchange for sharing his personal history and many remarkable insights into the inner workings of Cuban intelligence. During our first session he gave me an English-language copy of a nearly two hundred-page typed manuscript of analysis and recollections of his work. He had finished composing these untitled memoirs in 1990, three years after his arrival in the United States. In its pages, and in our conversations, he chose to put on the public record for the first time some of Fidel Castro’s most closely guarded secrets.
Scarcely any of his spectacular revelations have been openly discussed before. He told me, for example, about the DGI’s most valued acquisition, at least until the time of his defection: a penetration agent, or mole, in the upper reaches of the government in Washington. This man was so sensitive and influential an inside source that only Fidel and a single DGI case officer ever knew his identity.
The Cuban case officer had no other responsibilities but to meet with the American spy when he traveled abroad, where clandestine rendezvous could easily be arranged. This was before the introduction of sophisticated computer-based communications systems the DGI later would use with its top American agents. Back in Havana, the case officer brought the man’s reports directly to Fidel, who then decided whether any information could be shared with others in the DGI, including its director, or in the political leadership. Aspillaga told me, having been told by the case officer, that even Ramiro Valdés, Fidel’s trusted minister of interior who had oversight responsibilities for all Cuban intelligence and security agencies, was rarely if ever informed.
The American spy was Castro’s personal supermole in the Washington establishment. Fidel made every decision about how to deal with him: where and how clandestine meetings would be conducted; what questions the DGI officer should put to him; how to use him in deception and influence operations. This was the ultimate in compartmentalization and source protection, rare in the intelligence practices of other countries but not in Castro’s Cuba. It was probably because only Fidel and the Cuban case officer knew the American spy’s name and position that he was never prosecuted in the United States. Aspillaga did not know his name or where he worked in Washington, but told me he suspected the man was burrowed in at either the CIA or the Pentagon.
Judging from the extreme care taken in handling the spy, he must have been an equally or even higher level penetration than Ana Belen Montes, Cuba’s other star Washington mole. She spied for nearly sixteen years, most of them in the Pentagon’s Defense Intelligence Agency, before being arrested in September 2001. By then she had achieved high rank, enjoyed top-secret and other special clearances, and worked in a position of considerable responsibility. If, as it seems, the earlier penetration was an even more treasured Cuban source, he must have occupied an important subcabinet or comparably sensitive position.
Fidel and the mysterious mole apparently developed a long-distance affinity. Castro may even have met secretly in Cuba with this traitor to congratulate and encourage him and to revel in their success at duping the American “imperialist” enemy. As his country’s supreme spymaster for a few months short of forty-eight years, Fidel always delighted in personally meeting with his best foreign agents.
Three other American moles who ultimately were prosecuted and imprisoned are known to have basked in private audiences with the leader they adored. Montes, Walter Kendall Myers—who held a senior position in the intelligence branch of the State Department in Washington—and his wife, Gwendolyn Steingraber, all enjoyed congratulatory conclaves with Fidel. Put up at a Havana guesthouse in January 1995, the Myers couple spent about four hours with Castro one evening. Myers later enthused that the Cubans had given him “lots of medals” and that Fidel “was wonderful, just wonderful.” It was the rapture of a true believer in Castro and his revolutionary causes.
According to Juan Antonio Rodríguez Menier, another important DGI defector, a still-unidentified English woman said to be working undercover for Cuba somewhere in the United States was also honored this way. Like the four Americans, she had allegedly spied for many years, and also, according to Rodríguez Menier, provided Cuba with unspecified but “priceless information.”3
Aspillaga told me that the DGI had enlisted two productive spies inside the State Department. He said that sometime before his defection, two elected members of the US House of Representatives had been separately recruited and had visited Cuba by way of third countries, leaving no traces. It is difficult to imagine that Fidel was not personally involved in those triumphs, secretly meeting with the congressmen, charming and encouraging them to support Cuban causes. Gerardo Peraza, another defector from the DGI, told a Senate subcommittee in 1982 that Cuban intelligence had also made clandestine inroads within the US Senate, but the senator questioning him in open session interrupted him before he could provide details on the public record. Peraza did emphasize that the Senate was a major Cuban intelligence target. There can be no doubt that elected members and staffers of both houses of Congress still are.4
Aspillaga warned the Agency of a DGI operation that was planned against a CIA officer overseas just in time to defeat it. Information he provided compromised penetration agents seeking sensitive government positions.
He shared with me glimpses into Fidel’s personal life, including the story of a previously unknown child, named Ramón, that Castro had with a young American woman not long after he won power. I also learned of a university professor in the United States who worked as a trusted DGI influence and access agent. She was American born but fluent in Spanish, and had spent time in Cuba as a volunteer in the sugarcane fields as a member of what the Cubans called the Venceremos—We Shall Triumph—Brigade. Aside from her subversive effectiveness in molding her students’ thinking, her principal value to Cuban intelligence was as a talent scout and proxy recruiter. Notably, according to Aspillaga, she persuaded one of her most outstanding students, a young man of Latin American descent, to work for Cuban intelligence. Aspillaga described her as the student’s maestra guia, a master or teacher guide.
When she thought her student was ready to be pitched, she traveled with him to a third country friendly to Cuba and handed him off to her own DGI case officer. By then, as a result of her influence, the young man was ready to serve Fidel. He was recruited and went clandestinely to Cuba for tradecraft training. One of the more important skills he acquired was the ability to beat the Agency’s polygraph—the lie detector machine. The expectation was that he would gain employment at the CIA and begin working there as a Cuban mole. Indeed, Aspillaga recalls that the plan came alarmingly close to succeeding, and might have, had he not defected when he did. He told me that he never knew the identities of any of these Americans, or how many others in addition to that student were detected and neutralized by the FBI. But I am not aware of evidence on the public record that anyone meeting his descriptions was ever prosecuted.
Sadly, the same was true with respect to three turncoat CIA officers. Aspillaga shared recollections of two with me, and other DGI defectors I have interviewed provided additional details. All three of the CIA traitors seem to have begun working for Fidel after they had already left the Agency. That is small solace, however, because they inflicted grave damage and served their new masters for extended periods. Sharing sensitive secrets about CIA sources and methods, they exposed former colleagues and served as expert advisors after they switched sides. Two, Philip Agee and Frank Terpil, allegedly were used as spotters and bait in operations against Agency personnel. They—and perhaps the third American—worked at DGI headquarters in Havana as resident advisors to Cuban intelligence.
Agee, who died in a Havana hospital in January 2008, was the best known of the three. He did considerably more damage than the third defector, who I will not name. Suffice to say that this man was also an experienced Agency case officer, considered so valuable an acquisition by the DGI that he was housed in a luxurious Havana guest villa with a swimming pool. The facility was known, for obscure reasons, as La Lata (the can).
Russian spymaster and defector Oleg Kalugin wrote in his memoirs that Agee first approached Soviet intelligence in Mexico City in the early 1970s but was turned away. He then went to the Cubans, who, according to Kalugin, “welcomed him with open arms.” Aspillaga insisted that Agee “always worked for Cuba” and never for the Soviets. Kalugin added that in the 1970s and 1980s, the DGI continued to go after current and retired CIA officers and, without elaborating, claimed they “enjoyed some success.”5
Frank Terpil, code-named Curiel, or “guinea pig,” by the Cubans, was for a number of years the most valuable operational asset of the three American turncoats. He traveled to Bratislava during the winter of 1987 on a forged Cuban passport with two DGI officers. Their objective was to recruit a supposedly disaffected CIA officer, a computer specialist. He was to be offered $500,000 for his services but did not appear at an arranged rendezvous. Terpil was also housed comfortably by his hosts, in a spacious home at the Hemingway Marina outside of Havana. I am told that the residence was liberally seeded with concealed bugs and cameras. By 1995, the surveillance had found him wanting; Terpil reportedly was arrested, accused of financial crimes.
MORE SHOCKING YET was Aspillaga’s revelation that Cuban intelligence was running what was probably the largest and longest-lasting double-agent operation in the annals of modern spycraft. More than four dozen Cubans, recruited by the CIA as spies, were actually doubles working for the DGI. After Aspillaga had revealed their deceptions, the official Cuban media identified twenty-seven of them, men and women of various ages and from different walks of life. I. C. Smith, a senior FBI officer who worked Cuban issues in Miami at the time, wrote that with respect to Cuba, “the human intelligence capability of the CIA and the United States . . . was suddenly zilch.”6
Incredibly, counterintelligence warnings or investigations do not seem to have come into play in the CIA. Even Angleton’s large CI staff was never involved. Cuba was outside of its mandate. Nor had it been involved during the CIA’s calamitous Bay of Pigs invasion in April 1961, an operation that also had been thoroughly penetrated by Cuban intelligence. The obsessive Angleton was focused on the Agency’s main enemy, the Soviet KGB. No one on the CI staff, or anywhere in the CIA, thought that the Cubans were good enough to be running their own moles and double agents.
Yet there had been at least one earlier known case, perhaps forgotten in subsequent years. An official Agency history, now declassified and stored at the National Archives outside of Washington, acknowledges the existence of an exemplary Cuban double. Known in the Agency by his cryptonym, AMFOX–1, he had been recruited by CIA as a “stay-behind” agent before the American embassy in Havana was shut down in January 1961. He continued reporting covertly for a dozen years, until 1973, when he was finally detected and his duplicitous services were terminated by CIA.7
Most of the approximately four dozen Cubans who served as doubles against the CIA had been unreliable from the start. They were “dangles,” attractive bait— carnada in Cuban terminology—that the DGI proffered to unsuspecting and eager CIA officers. They had been carefully selected by Cuban intelligence for their psychological and intellectual suitability and the positions they held, and then they were intensively trained in a special school. Once recruited by the CIA, some remained on the Agency’s payroll for many years. In clandestine meetings with CIA case officers in cities all over the world, they were debriefed and given new assignments. Not all of them were Cuban; a few European sycophants of Castro’s revolution also worked as doubles. Aspillaga told me of one he knew as “Spaghetti.”
If the official Cuban media can be believed, one of the Cuban doubles— Eduardo Leal Estrada, an official in the Ministry of Communications—was actually feted by the CIA in a secret award ceremony “with drawn curtains and in total silence” in a hotel room. On the recommendation of CIA director William Casey, he was supposedly given a $10,000 bonus for his spurious spy work and a gold medal with appropriate Agency inscriptions. Known as Agent Alejandro to the DGI, he was considered an especially valuable source by the CIA because of his knowledge of Cuba’s national communications systems, including the coaxial cable network then being installed across the island. “The enemy was very interested in trying to defeat that endeavor,” he told the Cuban government press after being exposed.8
Antonio Garcia Urquiola was another typical case. Like more than a dozen of the double agents, he was regaled as a hero by the Cuban media soon after Aspillaga exposed him. A captain with Cuba’s main shipping line, he had been trained in counterespionage in the mid-1960s and assigned the code name “Aurelio.” He was therefore an ideal candidate for the DGI to dangle. He was offered up in Amsterdam in 1978, quickly recruited by the CIA, and assigned the code name “Alejandro.” He began meeting with case officers during ports of call. The CIA provided Aurelio/Alejandro with secret writing equipment, and supposedly he sent hundreds of messages to his handlers using invisible ink. He was later given a sophisticated transmitter that beamed concentrated burst messages to an American satellite or, according to the Cuban government exposé, to a CIA office on the fifth floor of the American diplomatic mission that was established in Havana in 1977. The code name he was assigned when transmitting messages to the Agency was supposedly “Dadon.”9
Garcia later claimed he had been paid $1,500 monthly in the latter years of his double service. By the time he was exposed, more than $120,000 had been deposited for him in secret American bank accounts. With DGI training, he says he was able to pass the Agency’s polygraph test. Later he boasted to a Cuban government reporter that “the device is meaningless.” (Another of the doubles claimed to have passed it three times; only one admitted to failing.) Garcia admired one of the CIA officers he dealt with frequently, describing him as “very experienced and professional.” But overall, he claimed, they “underestimated us and viewed us with contempt . . . they really blundered.”10
In some of the double-agent cases, the Cubans outsmarted the Agency by using clever psychological deception and performance techniques. One of their dangles—they called him “Robert”—presented himself as rebellious and eccentric. According to Cuban press accounts, he intentionally missed meetings with his CIA case officer and was cavalier when explaining why. It was a role scripted by the DGI to shake up the mix with the belief it might actually increase the CIA’s interest and confidence in him. He would not come across as a trained intelligence officer. And perhaps too it was done just for the sport of it, following guidelines laid out by Fidel himself, to see how much they could get away with. Another Cuban artfully played the role of a naïf who could easily be satisfied and fooled.
The challenges of orchestrating this symphony of counterespionage deceptions would have strained the ingenuity and resources of even the largest spy services. The best-known earlier example—the double-cross system run by British intelligence—succeeded in completely controlling German espionage on the home front during World War II and, prior to the Normandy invasion, ingeniously deceiving the Nazi High Command in Berlin about where the Allied forces would land. Winston Churchill, intimately involved in those deception operations as prime minister, famously referred to them as his “bodyguard of lies.”
J. C. Masterman was an Oxford don enlisted into a leadership role in running that complex operation. “Administrative problems were formidable,” he wrote, “almost overwhelming.” Copious records had to be kept on every double agent in order to avoid inconsistencies in reporting that might betray them. Every bit of information passed, the time it was done, and the likely implications of releasing it to the enemy had to be recorded. And there were fewer British doubles than in the Cuban operations.11
In wartime Britain, as in Castro’s Cuba, double agents had to be quarantined from each other. Only a small number of staff officers could be aware of any one case, and in Cuba, there were just a few, including Aspillaga, who knew of them all. Nonetheless, the DGI’s elaborate doubles structure was inherently precarious: If the CIA had uncovered any one of them, others might well have come under suspicion too as counterintelligence concerns were heightened. Any serious error could unravel the entire complex. The Cubans’ skill at keeping their own double-cross system secure for so long was an unparalleled accomplishment. After Aspillaga’s defection, CIA officers could only grudgingly marvel at how totally they had been duped.
The Cuban successes were a tribute to the country’s supreme spymaster. Other men, handpicked by Castro and his brother, Raúl, held the top offices in the DGI and other security services, but it was Fidel himself who led and personified Cuban intelligence. He presided as the grand master of the Cuban double-cross system, just as he insisted on managing all the most important agents and moles. Each of the doubles was handled by a DGI case officer who had to be intimately familiar with every development in a case. But these officers were mainly record keepers, logisticians. Fidel made all the most critical decisions.
He conceived the strategy, playing the game of deception three or four moves ahead and always with a number of pieces simultaneously in motion. He decided who could be dangled and who could not; which ministries and government agencies should be shielded from the CIA; and what information—termed “feed” or “smoke” by American and British intelligence—could be passed to the enemy. I have not been able to determine whether Fidel personally screened candidates to be dangled, but chances are good that he did at least in some cases.
Often he permitted doubles to share surprisingly sensitive data with the CIA to enhance their credibility. Most of the disinformation was factual and truthful, so when it was passed, it would more likely be accepted as valid. The feeds would have to seem sufficiently important too—revealing Cuban government secrets— in order to keep the ruse from raising suspicions. The CIA, after all, measured the worth and reliability of its agents on the merits of their reporting. Still, obviously the doubles could not give away really sensitive information. This is why no one from Cuban intelligence or the military was ever dangled.
Fidel’s commanding role stands in surprising contrast to how the British double-cross system was managed. The Twenty Committee was a collegial body of intelligence careerists and university dons, chaired by Masterman. It was represented by the Roman numerals XX—also, of course, signifying “double cross,” the X being a close typewriter keyboard symbol to a cross. Members met weekly in near-total secrecy to weigh all important decisions. Together, they approved what feed could be given to the enemy and devised the deceptions to be inflicted on German intelligence and military planners.
Masterman wrote that the Twenty Committee acted “as a clearinghouse where the work of various agents could be compared and kept within a reasonable measure of consistency.” Agents should neither contradict nor parrot each other when passing their feed; either course could raise suspicions on the receiving end. Keeping it all straight and in balance was a formidable challenge for Masterman’s team.
Fidel was not tempted to create anything like a Cuban XX committee. He played that role himself, with the boundless self-confidence and audacity that are among his defining traits. He was not averse to incorporating some checks and balances into the running of the Cuban doubles, but there was never any doubt in the ranks that it was really his show. In short, Fidel was the singleton equivalent of Masterman’s Twenty Committee, and he was just as flawlessly successful.
After Aspillaga’s defection, the theory and practice of doubles and dangles tradecraft was enshrined in DGI instructional literature. One sophisticated study was drafted by Zayda Gutierrez Perez, a DGI major who studied at the communist East German Ministry for State Security, the infamous Stasi. Completed in 1987, it reveals in considerable detail many of the underlying principles Fidel dictated for running penetration agents. Originally published in German and stored in the Stasi archives in Berlin, the study came to light after the two Germanys were reunited. It is the only substantial internal DGI document that I know of that has found its way onto the public record.12
Gutierrez wrote about “intelligence offerings,” the quaint Cuban term for “feed.” Fidel’s role in choosing the offerings is not explicitly acknowledged, though the major hinted at his involvement, writing that “the highest state officials . . . must take part.” She made clear that the overriding objectives of the program were manipulating and disinforming the CIA. The DGI learned a great deal from the deceptions; “highly valuable knowledge was gained,” she wrote. Cuban intelligence perfected its own tradecraft as it learned from CIA methods. According to the Cuban media, it acquired a bonanza of satellite and other advanced communications gear from the double agents.
But in fairness to the many CIA professionals at all levels who were taken in by the Cuban deceptions, it must be emphasized that, when carried out by a skilled intelligence service, doubles deceptions are exceedingly difficult to detect.
Richard Helms, from 1962 to 1965 the CIA deputy director for plans, the top spymaster, and future director, testified under oath about this area of secret tradecraft during a Senate hearing in 1975. He said, “This is one of the most difficult and tricky aspects of secret intelligence work, and there isn’t anybody who’s been in it very long who hasn’t been tricked once, twice, maybe many times. You just start each time afresh, taking the same chances and hazards . . . it is extraordinarily frustrating.”13
AS ASPILLAGA WAS UNMASKING Cuban operations during the summer of 1987, Fidel was plotting his revenge. The DGI was instructed to put together an elaborate media campaign to expose still more Cuban successes against the American archenemy. These new revelations were also acutely embarrassing.
About two dozen of the doubles and some of their family members were rounded up in Havana and transformed briefly into media stars. Carefully scripted, they told similar tales of CIA perfidy, real and invented. Lengthy feature stories and photo spreads about their double lives soon began rolling out in the pages of Granma, the official Communist Party daily paper, and on state television.
More than thirty of the doubles were sent on a whistle-stop tour around the provinces, presented everywhere as intelligence heroes. Fidel took part, hosting an assembly in the defense ministry’s main hall, the Sala Universal, with many of the double agents present. His brother, Defense Minister Raúl, and dozens of ranking intelligence officials were there. Incredibly, Fidel spoke for fourteen hours, reading many of the feeds he had helped draft that the double agents provided to the CIA. One of his bodyguards, a DGI officer who later defected in New York, shared his recollections of that event with me. He had to endure the entire spectacle, standing adjacent to Fidel. “My feet were swollen and sore,” he told me. “I was standing near Castro the whole time, guarding him.”14
Cuban television aired an eleven-part series, The CIA’s War Against Cuba, claiming to show in shocking detail how Agency personnel and operations on the island had been compromised for about a decade. The programs were viewed with mounting alarm at CIA headquarters, each containing fresh new surprises.
Fidel was orchestrating the entire show. Aware of the historic tensions that marred relations between the CIA and FBI, he found a devious way to exacerbate them at the CIA’s expense. He had the DGI prepare dubbed English-language versions of the programs and arranged for a set to be delivered to I. C. Smith, the FBI’s Assistant Special Agent in Charge of the Miami field office. Visiting CIA officials later asked Smith how he had acquired the dubbed tapes; they could find only Spanish-language versions. He was coy, indulging in a bit of harmless interservice gamesmanship. “I asked them for a set,” he said in his syrupy North Louisiana drawl. Then he walked away from his annoyed Agency counterparts, providing no further explanation.15
The Cuban documentaries were professionally done. Aspillaga told me that a special production group he knew of must have done all the work. The series featured extensive filmed coverage of Americans from the diplomatic mission in Havana as they engaged in what appeared to be basic intelligence tradecraft in remote areas of the island. Smith has written that they were CIA officers surreptitiously filmed by Cuban counterintelligence “leaving and picking up packages containing radios, money, and instructions for Cubans ostensibly working for the CIA.”16
The DGI surreptitiously recorded and filmed a few of the Americans during clandestine meetings with double agents in European capitals. The television series also featured documents supposedly written and photographs taken by CIA officers at various locations in Cuba. There was no explanation of how Cuban intelligence managed to acquire those materials, although clearly it had been through clandestine means. The exposé showed containers with bundled Cuban pesos, radios, and racks of seized communications gear. A hollow artificial rock was said to have been used in the countryside as a dead-drop device for the CIA to pass documents to a double agent.
One of the programs pictured a child’s toy, batteries, and furniture and described them as CIA concealment devices. An elegant Italian Maltese named Mauro Casagrandi—Cuban code name “Mario”—claimed in an hour-long interview with Cuban security officers to have been recruited by the CIA in Madrid, where he also passed a polygraph exam. A longtime resident of Cuba, he chuckled as he explained in fluent Spanish that over time the Agency paid him a quarter of a million dollars while he worked under Cuban control as a double agent. He did not say whether he got to keep the money.17
Double agent Juan Luis Acosta, captain of the Cuban tuna fleet—“Mateo” to the DGI—was one of those featured in a starring role in the press and on the TV series. He was selected to send the final coded message to the Agency after it became clear in Havana that all the double-agent deceptions had been exposed. The Cuban press claimed it was sent via an RS–804 satellite transmission device provided by the CIA. “On behalf of the state security agents and our fighting people, I am sending this last message. Viva Fidel!”18
The televised series was meant, of course, to put the CIA in the worst possible light. An American was shown conducting an operation wearing a T-shirt with “SUPERMAN” imprinted in large block letters running across his back. As the camera panned to get a close-up, the narrator intoned about the CIA’s arrogance and bullying belief that it is all-powerful.
Another American was seen near his car, searching for his keys supposedly lost when he placed a package in a wooded area, presumably for an agent to retrieve. In a similar rustic setting, the irate wife of another American is heard shouting “You idiot!” as he is seen outside his car concealing an object. A man is shown conspicuously leaving chalk marks on a park bench. Another is viewed perching on the tailgate of his vehicle in a wooded area testing what the Cuban media claimed was satellite communications gear intended for an agent.
All of the men caught on film, and the wives, are oblivious to the Cuban surveillance. Yet clearly multiple cameras were used in filming some of the incidents. Segments were shot from above, which probably means that small, sophisticated cameras with telescopic lenses were placed in tree limbs. They must have been remotely controlled because they panned left and right to follow the Americans as they moved about. Aspillaga believes the Cubans’ surveillance skills—what they call chequeo visual—were “among the best in the world.”
Targets were seen in close-ups and from various distances, so the cameras had zoom capability. Some of the sequences were filmed from eye level, dead straight ahead of the subjects. All of the footage shown on Cuban television was clear and in sharp definition. The programs demonstrated exceptionally sophisticated technical and surveillance skills. They also demonstrated that the DGI must have assigned a huge number of agents to monitor the Americans. All of the films were taken during daylight hours; it is not clear to what extent operations that may have been conducted at night went undetected.
Fidel and his intelligence bosses took considerable pleasure in taunting the Agency, hoping no doubt that the programs would ignite a firestorm of media and congressional criticism in the United States. It is interesting, nonetheless, that Castro and other top leaders stayed out of the show. To my knowledge, he never spoke on the record about his successes or the CIA’s humiliations.
As it turned out, the programs and their implications received scant attention in the American media during the summer of 1987. Other major developments— especially the Iran-Contra scandal and questions about President Reagan’s role in it—dominated the news that season. And, fortunately for the CIA, the two intelligence oversight committees in Congress cooperated either by suppressing the story or by never insisting on being fully apprised of it. Surprisingly, too, there were no leaks until years later. Perhaps in the summer of 1987 no one in Washington had a taste for another witch hunt.
There cannot be any doubt, however, that the CIA leadership was motivated to keep a lid on the story. So in the end, despite the Cubans’ determined efforts, the Agency sailed through the crisis with only minimal damage to its reputation by the televised exposé and the fiasco of the Cuban double-cross operations. In contrast, the wounds to morale were devastating.
Yet a tantalizing question the exposé left open, groaning to be answered, was just how the Cubans knew in advance precisely where to position their cameras. The double agents could not have told counterintelligence where to install surveillance equipment to capture the Americans on film and audiotape. Agents would not be told in advance by the CIA where they would need to go, say, to retrieve money or communications gear. They would receive detailed instructions only after their handler had made the delivery. These fundamental practices are described in any beginner’s manual about human intelligence or law enforcement tradecraft. The inescapable conclusion, therefore, was that, somehow, the CIA had been penetrated.
No matter how they had managed to do so—most likely it was in Havana, where they have overwhelming operational advantages—it was clear that the Cubans had been at it for a number of years and had attained extraordinary access to sensitive Agency secrets.
To my knowledge, these dreary conclusions have never been openly discussed before. I believe they would be indisputable, however, to anyone who viewed the Cuban television series and had even an amateur’s understanding of clandestine tradecraft—say, from watching spy movies or reading good espionage fiction. It was, of course, the regime’s intention to dramatize in the TV series that the CIA was deplorably inept and remained vulnerable to superior Cuban tradecraft.
Yet the most troubling question was never asked in public as far as I know. How had the CIA been penetrated?
I can only speculate. The Cubans may have had access to a CIA facility or, much less likely, were intercepting and decoding Agency communications. The worst of the possibilities—and one of the least likely—is that the suspicion Aspillaga shared with me was correct: Fidel’s personal supermole in Washington was a CIA officer assigned to the Cuban affairs staff. Perhaps there was such an Agency traitor, who might eventually have come under suspicion and was then neutralized and removed but who could not be prosecuted due to a lack of evidence to prove treason.
Still, the most likely explanation is simpler: The Cubans had regular access to the American diplomatic mission in Havana. The six-story building on the seafront Malecon Boulevard had stood empty for nearly seventeen years. It had housed the U.S. Embassy until diplomatic relations between Castro’s regime and the United States were severed and the building shuttered in January 1961, shortly before John F. Kennedy’s inauguration. Thereafter, the Swiss government was responsible for safeguarding the facility, but with a small staff in Havana and limited resources, there was not much it could do.
It is highly unlikely that the Americans had left any sensitive CIA records or equipment for Cuban intelligence to pick over when the facility closed. The official CIA history previously mentioned, reported:
When the break came, the Embassy had three days’ notice that it would close on January 4. The CIA station had just installed a new incinerator and managed to burn what files could not be shipped to Key West. . . . When they were not burning papers or smashing technical equipment, case officers were caching radios or making advance payments to agents left behind. . . . Station files not absolutely essential were crated and shipped back to headquarters. Case officers were working fifteen-hour days, seven days a week.19
A few colorful footnotes to the hasty American exodus across the Florida Straits are also worth mentioning. The deputy station chief, who anticipated the break in diplomatic relations, was able to make a “special trip on the Havana–Key West ferry to take out his personal car, silverware, and a valuable violin.”
Other CIA personnel were not so lucky. They “had maintained houses until the end and lost everything in them.” And then the last act was performed ritualistically, the exhausted CIA officers in Havana banding together in solidarity one last time: “On January 4 station personnel met at the embassy, rode in a convoy to the ferry, and sailed to the States.”20
Years went by, and the beautiful white embassy building stood vacant, regularly doused by Caribbean sea spray. There were no official Americans there during the Bay of Pigs fiasco in 1961, the terrifying missile crisis a year later, and the numerous other confrontations with Castro during the Kennedy, Johnson, Nixon, and Ford administrations.
Finally, limited diplomatic relations were reestablished on September 1, 1977. Jimmy Carter’s new administration and Cuba agreed to open “interest sections” in their respective embassy buildings in Havana and Washington. The American legation—known by the acronym USINT, for U.S. Interest Section, Havana—was technically a section of the Swiss embassy. It eventually grew nonetheless, into the largest diplomatic mission in Havana, even though it does not have the status of an embassy and is headed not by an ambassador but by a lower-ranking principal officer. The contrivance is necessary because the United States does not fully recognize the legitimacy of the Castro brothers’ government and has not established normal diplomatic relations.
Alan Flanigan, a career diplomat, served as USINT principal officer from 1990 to 1993. In an oral history interview a few years later, he was candid about the vulnerability of the facility even during the years when he served there.
We were never sure how secure the protection of the embassy building had been. Our assumption was that it wasn’t very secure at all, that Cubans had access to it rather freely over those many years, so when we moved back in we had to operate on the assumption that the Cuban intelligence service had the capacity to listen to everything we did there.21
Flanigan also recalled that “we had about 120 Cuban employees at USINT.” He did not need to add that virtually all of them worked in one way or another for Fidel’s intelligence services. Under the circumstances, a revealing Cuban government boast must be taken seriously. According to Granma, the television exposés during the summer of 1987 demonstrated how “the activity of the CIA station . . . has been under the surveillance of Cuban security forces at all times.”
The phrase “at all times” suggests not only that American personnel were constantly surveilled as they traveled around the island but that a CIA facility had been penetrated and that nearly everything that took place there was being observed or heard, and possibly both. The logical but repellent conclusion is that, when it opened, USINT was peppered with the most sophisticated and miniaturized audio and visual surveillance devices available at the time, honeycombed with tunnels and underground entrances connected to Cuban government buildings nearby, and stripped bare to the DGI’s prying eyes and ears. After all, Fidel’s men had more than a decade and a half to make the old embassy structure virtually their own.
It is easy to imagine that Castro ventured into the building himself, perhaps late at night, with intelligence officers guiding him and briefing on their handiwork. He has always relished this kind of vicarious pleasure in dealings with the United States. But regardless of whether he actually prowled the premises, it is very likely that DGI filmmakers prepared comprehensive documentaries for him showing the innards of the building. Surely, too, detailed architectural drawings and measurements were compiled. All of that would be of continuing use for future penetration operations.