During the summer of 1975, in the months between the American retreat from Vietnam and the massive Cuban military intervention in Angola, I began drafting my first national intelligence estimate, NIE–85-1-75, Cuba’s Changing International Role. By then I had about eleven years of experience as a Latin America analyst at CIA and as an air force intelligence officer, and I was completing my doctorate in Latin American history. Writing a difficult estimate was a welcome professional challenge.1
Whether they turn out to be right or wrong, prescient or mere iterations of the obvious, NIEs have rightly been considered the ultimate in intelligence analysis since the early 1950s. The various collection and analytic entities of the intelligence community participate as an estimate is drafted and coordinated and as evidence from all possible sources is brought into play. When that is done, agency heads gather to review and approve the text or offer dissenting opinions. The process is formal, often protracted, and cluttered with checks and balances. In the end, the CIA director takes personal responsibility for the facts and judgments compiled; estimates are his assessments, produced for the president and the senior national security team.
Like many NIEs, that one on Cuba was scheduled in support of urgent policy requirements. Top secret talks with the Castros’ government had been undertaken by Secretary of State Henry Kissinger with the objective of reducing bilateral tensions and moving toward a comprehensive rapprochement. Entirely an American initiative, it turned out to be the most serious effort until then to repair relations that had been veering between badly strained and conflictive since early 1959.
The first feelers, made directly to Fidel, had actually been extended in June 1974 two months before Richard Nixon yielded the White House to Gerald Ford. The earlier rapprochement with communist China was the model for what, it was thought, might be possible with Cuba too. Arms control and other negotiations with the Soviet Union had also brought results considered advantageous by both sides. It seemed reasonable, therefore, that if Mao and the Kremlin could engage constructively at the negotiating table, Fidel would also see some benefit in talking. Kissinger and his Assistant Secretary of State for Latin America, William Rogers, managed the process under a thick cloak of secrecy. At first, only a few of us in government were involved.
Ironically, nonetheless, the first round of official talks was conducted out in the open in a crowded cafeteria at LaGuardia Airport in New York, in January 1975. Lawrence Eagleburger, then one of Kissinger’s top deputies, huddled with two ranking Cuban officials to begin exploring the possibilities. He told them that ideological differences should not prevent the resolution of bilateral problems and that Washington was prepared to discuss everything of concern to Havana. The time for this initiative seemed propitious. Most Americans were tired of the long, acrimonious standoff, and many members of Congress from both parties were publicly advocating greater flexibility in the relationship.2
The pace quickened as I drafted the estimate. Exploratory meetings were held in Washington and New York, and the State Department went public, announcing that the United States was prepared to enter into serious discussions with Havana. In August, Fidel made a conciliatory gesture, returning ransom money obtained from the hijacking of an American airliner. Kissinger’s project seemed to be gaining some traction, and therefore the need for a comprehensive national intelligence estimate was unmistakable. There was a lot the American negotiators wanted to know.
Was Fidel really interested in improving relations? If he were to negotiate seriously, what would he demand and concede as the talks proceeded? What would his priorities be? Would he put any issues of concern to the United States off limits? What minimum concessions would he expect to receive? After the missile crisis, he had laid out a set of five demands, and in the early 1970s he was still stubbornly insisting they were his non-negotiable bottom line. In one appearance he stated the five succinctly: “We have demanded an unconditional end to piracy, blockade, infiltration, and airspace violations, and let them return the Guantanamo base.”3
The overarching issue for him was the economic embargo, which he has always referred to as a “blockade.” He insisted it would have to be lifted as a precondition for any real negotiations. But would he hold to that? There were hints of some flexibility.
No one doubted that the American naval base at Guantanamo, a prize left over from the Spanish–American War, would have to be returned to Cuba, and at that time—when, of course, there were no Al Qaeda terrorists detained there—even the Navy and the Pentagon probably would not have objected too strenuously. Fidel’s other three core complaints could easily be handled in ways that would assuage him.
Rereading a copy of the estimate years later, blank spaces obliterating a few sentences that were expurgated by CIA censors, I was pleased with how well it had aged. Most of what was predicted turned out to be right on the mark.
We were not sure that Fidel really wanted to engage in serious negotiations. If he did, we were confident he would drive a hard bargain. We even warned the Ford administration that he “probably calculates that, with the passage of time, pressures on the U.S. to accommodate him will continue to grow,” and that he would thus expect to “get a better settlement with a new U.S. administration.” It was hard to imagine him foregoing the anti-American bombast and vitriol that had been the rhetorical glue cementing his domestic and foreign policies for so long. Blaming the United States for nearly all of Cuba’s problems was second nature by then. Fidel would not be Fidel without the American enemy to berate.
It was the most challenging of the many national intelligence estimates I would write on Cuba and other countries in later years. It would have been much easier had we been tasked with, say, describing the strength and capabilities of Raul’s armed forces. Technical sources would have provided hard evidence of that. Writing about how the Cuban political system was evolving or how the economy was faring would have been easier, too, because reliable reporting from defectors and covert agents would be available.
Those were observable problems. But our task was to estimate abstractions—Fidel’s reasoning and intentions. I needed to get into his boots and try to think like him. Reading his and Cuban government public statements helped, but how flexible might he be once the initial diplomatic posturing had been played out? And as always when assessing him, the actual had to somehow be separated from the artifice. It was always safe to assume that elaborately interwoven substrata of deception lay beneath nearly everything he said and did in public.
Raul figured only marginally in the estimate, getting less coverage even than “old communist” Carlos Rafael Rodriguez, who was described as the third most powerful figure in the leadership. There had been no reason to believe that the brothers had feuded since their confrontation in April 1959 in Houston. All the evidence indicated they were working together harmoniously. Furthermore, the estimate was concerned with Cuban foreign policy decision making, and we knew that was Fidel’s bailiwick.
On the American side of the negotiating ledger, many thorny matters would be raised with the Cubans if serious talks developed. Havana’s military relationship with the Soviet Union was still neuralgic in Washington, more than a dozen years after the missile crisis, though the estimate emphasized it would be non-negotiable. Cuba’s commitments to exporting its revolution to other countries was a high American policy priority. We were confident, however, that Fidel would remain adamant about this. In the estimate, we concluded, “It is highly unlikely that Castro will renounce the right to support ‘wars of national liberation.’” That critical subject would be off limits in bilateral talks, with the exception, we believed, of Puerto Rico.
That self-governing American commonwealth appeared to be Fidel’s latest target as aggressive Cuban maneuvering in support of its independence intensified. More ink in the estimate was devoted to the island than to any other single subject because Fidel’s intentions there were the hardest nut we had to crack. Was supporting Puerto Rican independence a higher priority for him than improving relations with Washington? If so, there could be no progress toward rapprochement, probably no sustainable negotiations at all.
Puerto Ricans after all, are citizens of the United States. They vote democratically to choose their governor, mayors, and other local officials. A non-voting delegate in the House of Representatives stands for the island in Washington. For at least the last fifty years support for independence has been miniscule, rarely reaching more than 5 or 6 percent of the vote, and in recent years it has been falling even lower. Puerto Rico would be granted its independence in no time at all if that were the democratically expressed wish of the majority there. The issue had almost no salience anywhere else in Latin America, where even in the most nationalistic circles it was viewed as one of Fidel’s more peculiar obsessions.
The Cuban involvement in promoting independence was therefore difficult to understand. I knew that as a university student Fidel had been involved in bloody street demonstrations and that in his very first press conference after the guerrilla victory in January 1959 he had called for Puerto Rican independence. And the evidence was plentiful in 1975 that he was vigorously brandishing the matter again.
The estimate indicated that “over the past year or so the issue has been pressed with unprecedented intensity at the UN and other international forums, Havana was the site of an international conference in early September to generate support for that cause, and top Cuban officials increasingly have become identified with it.” I noted too in the text that Fidel himself had said publicly, just a few weeks before we completed the estimate, that Cuban solidarity with Puerto Rican independence was a matter of principle that he would never renounce—not even to improve relations with the United States.
Was that his hardened position, or would he be flexible once engaged in negotiations? Like all the others involved in producing the estimate, I thought Fidel would see greater advantages in putting the Puerto Rico matter aside for the sake of getting relief from the economic embargo and achieving tangible benefits from improved relations. So I wrote in the estimate that “Despite the strong public statements of its leaders, we believe that there is some flexibility in Cuba’s position on Puerto Rico.”
That judgment was one of the two embarrassing mistakes we made in that exercise. It demonstrated starkly the perils of misreading the intentions of a leader as idiosyncratic as Fidel Castro. In Washington the thinking was that the rational choice was for him to downplay his interest in Puerto Rican independence for the sake of the economic and diplomatic rewards that would come with rapprochement.
But that was not his calculus. Certainly he was thinking rationally by his unique standards. His third-world interests and allies, not better relations with the United States, were his top priorities. We had been guilty of the classic analytic trap known as mirror imaging.
We made a second major error too, an oversight or failure of imagination. There was only one anodyne sentence in the estimate about Angola. But just as work on that estimate was being completed, contingents of Cuban military advisers were secretly arriving in Angola. They were sent to help the Marxist liberation movement there consolidate power as centuries of Portuguese colonial rule was expiring. That fall more Cuban advisers, and then troops, began pouring in, and by the end of the year as many as fifteen thousand were on the ground in that large southwest African country, engaged in combat operations.
The intervention came as a complete surprise. Cuba had never done anything like it before, and I don’t think that any of us involved in thinking through the content of that estimate even considered the possibility. We were not the only ones surprised. Kissinger later wrote in his memoirs that it had been unimaginable Fidel “would act so provocatively so far from home.”4
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As the drafter of the estimate, I got to present the coordinated text to the chiefs of the nine main foreign intelligence agencies. On October 19, William Colby, the CIA director, chaired the session in the unpretentious little conference room near his office that has served all the Agency’s directors since Allen Dulles. An American flag stood in one corner. A large photograph of President Ford hung on the wall to Colby’s left. Plaster seals of all the intelligence agencies, each about a foot and a half in diameter, were arrayed on the other two walls. The FBI’s plaque hangs among them, but it was the only principal agency that did not participate that day, or at any time during the process. I would not know until later how much its absence had damaged the collective effort.
What the FBI knew but the CIA did not was that Fidel had been supporting Puerto Rican terrorists for years. The hardcore Puerto Rican revolutionaries he backed and encouraged were not like the guerrillas of the so-called national liberation movements Fidel had helped in other countries because they had virtually no popular support.
They engaged in criminal activities on the island and the American mainland, and were responsible for a number of murders, bombings, and other felonies. Cuban intelligence agents, reporting to Fidel himself, worked with them for twenty years or more, their collaboration apparently beginning in the early or mid-1960s. What the Bureau must have known in 1975 about this Cuban support for terrorism within the borders of the United States was not conveyed to us foreign intelligence analysts. Had we known, even in just the broadest outline, of the Cuban government’s activities, the estimate would certainly have reflected a harder line than it did.
Sadly, in those days, not long after the death of J. Edgar Hoover, the CIA and the FBI operated as rival intelligence services. What little cooperation there was occurred mostly on the margins, the two bureaucratic cultures rarely finding any common ground. To some extent the tensions were understandable. Law enforcement and foreign intelligence collection missions do not easily meld. FBI agents above all seek to prosecute criminals by using all the available evidence against them. By law, however, CIA officers must protect foreign intelligence sources and methods, so they are loath to go to court or to have their sensitive agent reports used as evidence.
There was a missed opportunity for greater cooperation back in 1975 that would have helped us avoid the intelligence failure on Puerto Rico, which paled, of course, in comparison to subsequent ones. The rivalries and opposing cultures persisted for many more years and contributed significantly to the inability of American agencies to predict or prevent the September 11 calamities. It is to be hoped that the new director of national intelligence will begin to rectify those problems and ensure that the CIA and FBI are really working in tandem.
By the time the Cuban-sponsored Puerto Rican terrorist groups finally played themselves out in the late 1980s, they had taken more American lives and inflicted more damage within the United States than any other international terrorists operating in the homeland other than the 1994 and September 2001 Al Qaeda attacks on the World Trade Center in New York City. The Puerto Rican operations were all mounted with concerted Cuban support.
In the 1970s and early 1980s, the two principal groups—the Macheteros and the Puerto Rican Armed Forces of National Liberation, known by the initials FALN—conducted extensive, carefully planned, professionally directed, and well-funded campaigns in a number of American cities. They were well armed and trained by their Cuban mentors. Much of what they did would not have been possible if not for sustained clandestine Cuban government encouragement and support.
Machetero terrorists were responsible for the deaths of two American servicemen and the wounding of nine others when a navy bus was ambushed in Puerto Rico in 1970. They fired on their unsuspecting targets with Soviet-made machine guns. Numerous bombings on the island and in New York and Chicago were their work. Macheteros killed a Puerto Rican policeman and took credit in 1981 for the destruction of eleven Puerto Rican National Guard jet aircraft at an island airbase.5
On September 12, 1983 a group of them implemented the well planned Operation Aguila Blanca, White Eagle. They assaulted a Wells Fargo armored car terminal in Hartford, Connecticut, stealing more than $7 million. It proved to be a perfect crime because the Cuban intelligence service was so involved. Much of the money and Victor Gerena, the main Puerto Rican perpetrator, were covertly exfiltrated to Havana in a series of typically proficient Cuban operations.6
After the robbery, Gerena hid in a secret compartment of an old motor home as it was driven from Texas across the border into Mexico. There he was met by Cuban agents and escorted to a safe house in Mexico City. Later he was provided with a false Argentine passport and smuggled to Cuba where he disappeared and probably still resides under Cuban government protection. Most of the Wells Fargo money also wound up in Havana, sent via the Cuban diplomatic pouch. Some reports indicate that the Cuban government kept a substantial portion of it for its own use in promoting revolution in other Latin American countries.7
Gerena was officially identified for the first time as a terrorist in December 2004, when the FBI announced an increase in the reward for his capture to one million dollars. At a Connecticut press conference, Bureau officials noted that Gerena and Osama bin Laden were then the only two terrorists on the FBI’s Ten Most Wanted List.8
Edmund Mahony, a Connecticut investigative reporter with the Hartford Courant, has written extensively about the Wells Fargo case and its Cuban intelligence connection. In a groundbreaking series of articles in November 1999 he described the web of ties between Cuban agents, the Macheteros, and the FALN. He found that the two terrorist groups, “created in consultation with Cuban intelligence agents,” bombed a total of more than 120 targets beginning in the 1970s and possibly earlier.
Mahony quoted an unidentified retired FBI counterterrorism specialist familiar with tapes of conversations between Machetero leaders and Cuban intelligence agents:
“They were talking about Fidel. This was being decided at the highest levels in Cuba.”9
That was consistent with the recollections of the Carter administration’s senior Latin America specialist at the National Security Council. Robert Pastor, who consulted with Fidel and other ranking Cuban officials in Havana, later wrote about Fidel’s Puerto Rico fixation.
“In discussing Puerto Rico in separate conversations with Cuba’s highest officials, I found that only one could be said to be genuinely obsessed with the issue, and that person was Fidel Castro.”10
Two former Cuban intelligence officers now living abroad also have divulged details of Cuban involvement in Puerto Rican terrorism inside the United States. Jorge Masetti defected in 1990 after many years of working in European and Latin American countries for Cuban intelligence. He named Jose Antonio Arbesu, a ranking Cuban intelligence official who later served as the top Cuban diplomat in Washington, as one the masterminds of the exfiltration operation through Mexico City.11
Domingo Amuchastegui, another former Cuban operative now living in the United States, described for the Hartford Courant Puerto Rico’s special status in Fidel’s calculus, and he later reiterated these thoughts in a conversation with me in the Washington area.
“Puerto Rico is different. For us in Cuba this was a part of a sacred policy or principle. For us, until this day, Puerto Rico is a colonial case.” He added, “Fidel Castro has stated privately many times that the day in history when only two people in the world advocate the independence of Puerto Rico, one of those two persons will be him.”
Amuchastegui remembered his former leader’s thinking accurately. Fidel told Barbara Walters almost exactly the same thing.
“So long as there is one Puerto Rican, just a single one, who wants independence for his country, so long will we have the moral and political duty to support him. Even if there is just one! If some day there are none, then that will cease to be our commitment to Puerto Rico.”12
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As Cuban intelligence agents were busy assisting Puerto Rican terrorists, they were also on the watch for sympathetic individuals who might be recruited as spies for Havana. The highest ranking Cuban mole ever apprehended in the United States was a Puerto Rican woman who worked over a period of seventeen years for Fidel. Ana Montes, a ranking Latin America analyst and a specialist on Cuba and Nicaragua, in DIA, the Pentagon’s Defense Intelligence Agency, admitted her guilt and was sentenced in 2002 to twenty-five years in prison. She was such a loyal adherent of the revolution that at her sentencing she boasted of the moral obligation she felt to Cuba because American policy has been so “cruel and unfair.”
Montes did enormous damage, and some sensitive information she provided the Cubans reportedly was then shared with the intelligence services of other countries.13 Her crimes would have become progressively more damaging to American interests had she not been apprehended when she was. She stood a good chance of becoming the ranking Latin American analyst at DIA. She had access to highly sensitive intelligence and defense information. And because of her seniority she exercised considerable influence over more junior analysts, including some at SOUTHCOM, the Pentagon’s unified military command in Miami that has operational responsibility for most of Latin America and the Caribbean.
When I was National Intelligence Officer for Latin America from 1990 to 1994, serving as the most senior analyst for that region in the dozen or so agencies of the intelligence community, Montes participated in the coordination of a number of assessments, including at least one national intelligence estimate. I never trusted her competence as a Cuba analyst, when, in retrospect, I ought to have registered a counterintelligence red flag. She was perhaps the most sour and unpleasant person I have ever worked with, but unfortunately it never occurred to me during the entire time I knew her that she was diligently working for Fidel.
I remember speaking to a veteran CIA Cuba analyst after Montes was convicted. “Everything we wrote on Cuba during those years was for nothing,” the analyst bitterly complained. She assumed, no doubt correctly, that all of our most critical assessments on Cuba were promptly transmitted by Montes to Havana. I expect that Fidel was the most enthusiastic reader of her drops and that he personally supervised her handling as he does with most high-level intelligence cases, and many lesser ones as well.
I know that I was an important collection target for Montes. I had first come to the attention of Cuban intelligence in the early 1970s, and by the time I became National Intelligence Officer for Latin America in 1990, a thick dossier had been compiled on me. During my two official visits to Havana in the early 1990s, I was under blanket surveillance by my Cuban counterparts. I have no doubt that their files on me include a large quantity of photographs, videos, and audio tapes. I know that they have transcripts or recordings of lectures on Cuba that I delivered when I was an adjunct university professor, I assume from one or more of my students who reported to them. They also retain copies of many articles and book chapters I have written about Cuba. I sometimes wonder what else they might have.
On a few occasions my opposite numbers in Havana have delighted in taunting me, but in one instance it was in a fanciful fashion. In the summer of 1993, when I was serving as National Intelligence Officer, I chaired the process of producing my last Cuba national estimate. On July 21, Havana Radio broadcast a report summarizing a story that appeared that day in Granma, the Cuban Communist Party daily. They knew I would be more likely to read the FBIS transcript of the broadcast than the newspaper report, and they wanted to make sure I was aware of the story. I suspect, given the tendentious relationship I have had with him, that Fidel himself wanted it to run, and may even have dictated much of its language.
Even though there had been no public acknowledgment that an estimate was in production, he and Cuban intelligence knew about it from Montes. The Cuban government reporter was quoted as saying the estimate “could have as its point of departure, the same old erroneous considerations that have induced earlier US administrations to err: that is, reports plagued by narrow, unrealistic views, and lacking in strategic content.14
Their final shot was to comment on some of my travels in and near Havana during my two visits to Cuba.
“The incomprehensible thing is for those men to think they can find out what the true feelings of almost eleven million people are by taking pleasure rides through the Vedado section of Havana or while seemingly on summer vacation on the beaches.…”
Overall, Cuban intelligence is one of the five or six best such organizations in the world, and has been for decades. It is narrowly focused on the Washington policy community, including Congress, and on the Miami Cuban exile community, as well as anyone who can provide useful information about either. Like all intelligence services it has had its share of failures, and following a series of morale-shattering purges of the parent Ministry of Interior in the summer of 1989, it has been rebuilding much lost competence. But it is very good still, and judging from its snide commentary on my visit to Cuba, even seems to exhibit a certain sense of humor.