AFTERWORD

DURING THE KENNEDY YEARS, LITTLE WAS OFF LIMITS IN THE intelligence wars waged across the Florida Straits. CIA had the authority to plot Castro’s assassination, so covert actions designed to compromise Cuban officials would hardly have been considered morally objectionable—even if innocent targets might be executed for treason. That possibility loomed through the more than three years the Agency ran an especially sensitive and ethically questionable operation apparently code-named AMROD. It continued in force until March 1966, covertly implicating prominent Cuban officials in capital crimes.¹

According to a declassified CIA summary of the case, it was designed to stir dissension in the Cuban leadership and sow discord between Havana and its Soviet patrons. Originally approved by an interagency coordinating committee in 1962 when Bill Harvey was running Task Force W, it reached full velocity a year later, coinciding with Des FitzGerald’s efforts to divide the Castros’ armed forces. It was a supercharged effort, one too sensitive to be mentioned even in large group meetings with the president in attendance. I have found no record that he or the attorney general was briefed on AMROD, but given its scope and success, and their interest, there can be no doubt that it was brought to their attention privately.²

Two prominent Cubans—a deputy defense minister and a diplomat at the Mexico City embassy—were tarred and were lucky to escape with their lives. Sixty-two-year-old Joaquín Ordoqui was the principal target. One of four deputies in Raúl’s ministry, he also served as armed forces quartermaster. An “old communist”—that is, a founding member of the pre-revolution Communist Party—he remained especially close to the Kremlin. Tensions flared early in 1962 when Castro and his “new communist” followers, nearly all veterans of his guerrilla movement, condemned the older generation of Marxists for engaging in pro-Soviet subversion. Fidel launched a purge of those “sectarians” who were allegedly more devoted to Moscow than to him. Dozens were disgraced and exiled. In reality, the show Castro staged was mostly smoke and mirrors meant to demonstrate his absolute authority and to weed out a few rivals. But the affair was closely tracked in Langley and provided appealing operational opportunities.³

The objective was to jolt fault lines in the leadership, with the added hope that Moscow would side with Cuba’s “old communists” against Fidel. Generous Agency resources at headquarters and in Mexico City were devoted to carrying it off. The large Mexico station—with about forty CIA personnel in late 1963—was up to the task. It surreptitiously photographed most people entering or leaving the Cuban diplomatic compound and tapped at least six phone lines there, including the ambassador’s. By late 1963, CIA had recruited about fifty agents in the Mexican capital to work against the Cuban target, including two inside the embassy. Declassified records show that, wittingly or not, the Cuban chargé, code-named AMRIFT, played a critical role in the AMROD operation.⁴

It was one of the more remarkable covert operations ever run against Cuba’s leaders. In April 1963, counterfeit documents falsely attributed to a disaffected CIA agent in Mexico were passed to a Cuban embassy official, probably AMRIFT. The documents made it appear that Ordoqui was a CIA agent and that he had handed over sensitive military information in the run-up to the missile crisis. According to a CIA record of the operation, “the Cubans accepted the spurious papers and paid for them per our demand.” Additional deliveries of falsified documents were made through the summer, and the eager DGI paid several thousand dollars more. At first, nothing seemed to happen to Ordoqui, although there can be no doubt he was put under round-the-clock audio and visual surveillance.⁵

In November, as the Cubela conspiracy was ripening and there were still no signs of new political turmoil in Havana, fifty-year-old Maria Teresa Proenza was also targeted. The respected Cuban cultural attaché in Mexico was an “old communist” friend of Ordoqui’s. A celebrity and socialite, Proenza was a former personal secretary of the acclaimed Mexican muralist and painter Diego Rivera. Her enormous influence in Mexican artistic and intellectual circles, hardcore communist beliefs, and virulent anti-American attitudes caused her to become the Agency’s newest victim. Another document sale falsely fingered her to the DGI as a CIA agent. Within weeks she was recalled to Havana and put under house arrest.⁶

The first Cuban reactions to the deceptions were not evident until the following March. A young communist protégé of Ordoqui’s was arrested and tried for capital crimes to which he confessed. In reality, however, when the death sentence was carried out, he was a surrogate for Ordoqui. “It was really a trial of the latter,” according to the CIA summary of the operation.

The deadly charade was typical of Fidel’s operating style, and there were few among the island’s political elite who misunderstood. Ordoqui was too closely connected to the Kremlin to be put up against the execution wall, especially as relations had warmed following Fidel’s long sojourn in the Soviet Union the previous spring and as economic and military subsidies increased. In 1964, he had no taste for another sweeping purge of Cubans beholden to Moscow.⁷

But Ordoqui was not given a free pass; he was arrested that November as the sale of counterfeited documents continued apace in Mexico City. His wife, a cabinet minister, was detained too. AMROD stayed on track for another sixteen months, CIA document counterfeiters artfully producing new ones, all so seemingly authentic that they were totally believable to Cuban intelligence. Finally, according to an official record of the operation, and for unknown reasons, “the Cubans ceased taking an interest in it.”

Only a few relevant documents have been declassified, so it is not possible to tell how many other Cuban officials may have been affected. Two years after the last ersatz papers were sold, however, Fidel unleashed a second purge of “old communists.” In the aftermath of that so-called microfaction affair, only a handful of the old-guard Marxists remained in important positions. Operation AMROD may very well have been decisive in their collective downfall.

The three defendants survived and eventually were paroled. Ordoqui died of natural causes in Cuba in 1973. His wife was allowed to live out her years in Spain. Proenza remained in Havana, where she was interviewed in 1978 by the House assassinations committee. She was a close friend of her Havana neighbor Luisa Calderon; “I see her often now,” she said. Unverified but credible reports had also linked Proenza to Oswald during his visit to Mexico. She denied any knowledge of him, saying she knew nothing either about his threat, reported by Jack Childs, to kill Kennedy. Proenza gave no indication of knowing that she had been framed by the enemy CIA.⁸

To my knowledge, this story has never been aired publicly before. Published references by two CIA officers, however, do seem to point at AMROD. In their memoirs, David Phillips and Ted Shackley appear to mention it in fleeting, shielded terms. Phillips, who was in charge of covert operations against Cuba at the Mexico City station beginning in mid-1963, wrote that the targeted cultural affairs officer was “energetic and bright, despised Americans, and had hatched . . . dirty tricks aimed at CIA.” Although he disguised the nature of the operation and depicted Proenza as a man, Phillips’s description neatly fit her. Not surprisingly, he says nothing about how dangerously she was compromised or that she might easily have been executed as a CIA spy.⁹

Shackley was more critical in his brief reference to an operation that closely resembles AMROD. But his complaint was not on moral grounds. He wrote that “[i]n a limited sense this was indeed a success because it caused some disruptions and discord in the enemy’s bureaucracy.” On balance, he thought the case was largely a lark that did little more than give CIA “the satisfaction of poking Fidel in the eye.” Perhaps he was not aware of the show trial and execution of Ordoqui’s young disciple, the sacrificial lamb in the affair. And perhaps the cold-blooded Shackley considered the operation just as fair and routine as the commando and sabotage campaigns he ran that resulted in considerable loss of life on both sides of the clandestine war with Cuba.¹⁰

It is not known when Fidel and his intelligence chiefs realized how grandly they had been deceived. No Cuban official or any state media has commented on the case. It is not their practice to admit to any such embarrassing calamities, especially since they paid dearly for the flow of forged documents. But by the mid- to late 1970s, they apparently had learned of the deceptions, perhaps from CIA turncoat Philip Agee, who had some knowledge of the case. I have concluded that since that time, the Cubans have toiled to exact revenge. They chose a single target. ¹¹

If, as seems likely, Dave Phillips was the Mexico City principal in charge of AMROD, a long-running disinformation campaign against him—continuing today, long after his death—is probably a maliciously calculated case of Cuban retribution. According to some Kennedy assassination conspiracy theorists who have been taken in by the disinformation, Phillips used the alias Morris or Maurice Bishop when supposedly meeting with Oswald as his CIA case officer.

Cuban intelligence may not have been the first to promote the canard, but counterintelligence general Fabian Escalante soon became one of its most prolific propagators. Cuban government commentators and others have repeated it ad nauseum. The CIA has denied any knowledge of Bishop and that it had dealings with Oswald, and Phillips successfully sued publications in the United States and Britain that alleged he used that alias to meet with Oswald. Of course he could not sue Cuban government media, and, undeterred, they have continued to proclaim the infamous lie that he was a CIA conspirator in Kennedy’s assassination. Even some otherwise sensible American scholars have been taken in.¹²

NO OTHER ADVERSARY INTELLIGENCE SERVICE has enjoyed gloating rights comparable to Cuba’s since the 1930s and 1940s, when more than five hundred Americans assisted Soviet intelligence. Those fellow travelers were seduced by the myths of a Marxist paradise or traveled there and naively came away enamored and eager to help. Others were born in Russia before emigrating or identified with the Kremlin because of shared ideology. Americans have conspired for Fidel for the same reasons and also because, like Lee Harvey Oswald, they idolized him and were persuaded that he and revolutionary Cuba were the innocent victims of brutal Yankee imperialism. For nearly all the converts, working for Castro has been an unremunerated labor of love.¹³

In most years since the early 1960s, the number of Americans assisting Cuban intelligence—moles and spies, doubles, access and influence agents, spotters, sycophants, and support assets—probably add up to between three and five hundred. Some of them—say, when meeting with Cuban operatives posing as diplomats or cultural affairs officials and accepting tasks or guidance from them—may not be aware they are actually aiding Cuban undercover programs. But most Americans in such situations who sympathize with Cuban government objectives cannot have any illusions about whom they are serving.

As early as September 1963, the Miami Herald reported that Castro’s intelligence agents had penetrated “every facet of the Cuban exile movement.” DGI operative Gerardo Peraza, who defected in 1971, knew that more than three hundred recruited Cuban agents were then working for Fidel in Miami alone. Today, the numbers throughout the United States are probably comparable, and the underground infrastructure that supports them is probably better than ever. That is partly due to the loss of other intelligence priorities. Since the disintegration of the Soviet bloc, Cuban support for foreign revolutionaries has withered. Similarly, from the 1960s through the 1980s, illicit acquisition of American technology and manufactured goods was a costly Cuban intelligence priority. That has also faded in recent years as legalized trade and contacts across the Florida Straits have multiplied. The result is that nearly all Cuban intelligence resources have been directed to focus on Washington and Miami.¹⁴

Espionage and counterintelligence have been the beneficiaries. Infiltrating sleeper agents and illegals is astonishingly easy for Cuban intelligence. At least thirty thousand émigrés arrive every year in the United States from the island and meld into American society. Twenty thousand of them come under the terms of an immigration agreement concluded with Havana during the Clinton administration. The remainder travel by way of third countries, or on small craft to Florida, but usually are not repatriated as long as they reach American soil.

All qualify a year later to begin the process of acquiring citizenship under the terms of the Cuban Adjustment Act, legislated in 1966 at the height of the cold war. These antiquated immigration laws and rules—which apply only to Cubans among all émigré nationalities—work to the continuing great advantage of Cuban intelligence. For this reason, and because they are discriminatory and outdated, they are no longer justified.

The Cuban intelligence threat is compounded by liaison and sharing agreements it maintains with other regimes and groups hostile to American interests. Sensitive information acquired through espionage is provided in exchange for reciprocal favors, profit, or as a show of ideological solidarity. Civilian and military technology and American spyware have been compromised this way. Ana Montes, the Cuban mole in the Defense Intelligence Agency, was arrested just a day before she would have gained access to secret targeting data for the October 2001 military operations against al Qaeda and the Taliban in Afghanistan. The Pentagon feared that she would pass sensitive military plans to her Cuban handlers in time for them to warn the enemy. She is reported to have given the Cubans copious details of secret American electronic eavesdropping systems that may have been shared with other countries. And Montes was suspected of having provided information about US military and intelligence operations in Central America during her long service for Cuban intelligence.¹⁵

But American counterintelligence capabilities have improved dramatically in recent years. Only four Cuban spies were arrested in the United States between 1959 and 1995. Then, beginning in September 1998 and through 2011, about four dozen Cuban agents have been prosecuted or neutralized. More than thirty were members of the sprawling Avispa, or Wasp, network wrapped up that year.¹⁶

Since their arrests, six other American citizens working for Cuba have been prosecuted successfully. Carlos Alvarez, a Florida International University professor, and his wife, Elsa Prieto, a university counselor, pled guilty in Miami to conspiracy. Mariano Faget, a naturalized American born in Cuba, was convicted in 2000 of spying while he served as an upper-level official of the Immigration and Naturalization Service. The prosecutions of Ana Montes, Walter Kendall Myers, and his wife, Gwendolyn, have been discussed already. Still others, some prominent in academic circles, who wittingly assisted Cuban intelligence have been neutralized as viable secret assets without being criminally prosecuted.

The Montes case remains the most troubling. She spied for sixteen years, rising into steadily more sensitive and responsible positions in the intelligence community. She first came under suspicion early in 1996 and was interrogated that November by a Defense Intelligence Agency security officer after consultations with the FBI. Although he believed that she lied to him and found her evasive and manipulative, remarkably, she was allowed to resume her sensitive work as a political and military analyst on Cuba. The wiser course would have been to reassign her to some other specialty or country desk while investigating her further. At least then her utility to Cuban intelligence would have been minimized.¹⁷

I have learned that the FBI also missed opportunities that could have led to Montes much sooner. Miguel Mir, the Cuban intelligence and security officer who served for six years on Fidel’s personal security squad, defected from his post at the Cuban diplomatic mission at the United Nations in May 1996. He told me of information indiscreetly shared with him by two of the most senior officers at the large Cuban intelligence Center in New York. In retrospect, he believes that both colleagues were making indirect references to Montes.¹⁸

The first incident occurred in early 1995. Mir drove to Washington from New York as a security escort for intelligence lieutenant colonel Luis Carrera, who was allegedly Montes’s principal contact in the United States at the time. During the boring drive south, Carrera boasted, “I have contact with a very important person who works at the highest levels of the American government.” He provided no details, but Mir believes the purpose of the trip was for Carrera to meet secretly with Montes or, more likely, to execute a brush pass with her somewhere in the Washington subway system in order to clandestinely provide or receive sensitive materials. Mir recalls Carrera later said it took two or three tries to effect the exchange.

The second fragment of information came from a conversation the defector had in New York. In February 1996, the outspoken Mir had a confrontation there with the visiting Cuban foreign minister. The next day, Center chief José Odriozola summoned Mir to be privately admonished in the secure cabina, a plastic enclosure within a larger room where sensitive conversations could he conducted without fear of audio interception. Mir told me how Odriozola reprimanded him, saying: “It is really ironic; you were given the twentieth-anniversary-year Ministry of Interior medal and many other honors, how could you have been so lacking in respect for the foreign minister?”

Odriozola was a senior and experienced intelligence officer who had previously served as Paris Center chief. Other defectors have also described him to me, and his name is included in the list of DGI officers I received from Aspillaga. But in rebuking Mir, this veteran operative committed fundamental errors of tradecraft, violating basic rules of compartmentalization when he revealed this information: “We have penetrated the Congress of the United States,” he bragged, “the Senate, and the Pentagon, and we have a very powerful operating network . . . and you have been so disrespectful of us!! We should send you back to Cuba, but because of your accomplishments, we will let you remain here.”

Mir later concluded that his boss was referring to the Wasp network in Miami and to Montes. A few months later—a day before he was scheduled to return to Cuba, his tour of duty in New York completed—Mir defected.

He told me he provided these leads to the FBI in May 1996. It is possible that they helped investigators in the search that five years later led to Montes. But there is no reason to believe they were factored in when she was interrogated at DIA a few months later. The published account by the security officer who grilled her makes no mention of information provided by a defector. Were the tips Mir passed on from the two senior Cuban intelligence officers disregarded or considered too vague and ambiguous to pursue?¹⁹

American authorities have never revealed how Montes finally came under sufficient suspicion to be put under surveillance and then caught red-handed in espionage. The Defense Intelligence Agency security officer who wrote about her case stated only that “a tidbit of information that might help identify a Cuban spy surfaced within the counterintelligence community.”

He did not elaborate, and no details of the evidence trail surfaced during Montes’s prosecution. The mysterious tidbit could have come from another defector or an intercept of Cuban communications. Montes or her handlers may have made an incriminating error in the way they arranged contacts. A colleague or family member could have become suspicious and reported her to the FBI. Most embedded spies are ferreted out in one or another of these fashions.

But I suspect that in her case, the critical tidbit came from an egregious error committed by Fidel Castro himself. He was surely Montes’s ultimate case officer and followed her with intense interest. He probably met with her in Havana. But his health—and mental acuity—were deteriorating by 2000, after earlier life-threatening surgeries. In June 2001 he was filmed for the first time faltering during a speech. He appeared disoriented and dizzy, nearly collapsing before being carried off by aides. Nothing like that had ever happened before, and the international press reported that he had briefly lost consciousness. In two subsequent appearances that summer, audiences squirmed in embarrassment as he became strangely incoherent for short spells. Something, both physical and cognitive, clearly was wrong.

I cannot support my surmise about Fidel’s responsibility for Montes’s arrest with hard evidence. It is based mainly on my understanding of how he and Cuban intelligence have operated. I suspect that Fidel, in a disoriented state, boasted when he was among other Cuban officials of an extraordinary, high-level spy working for him in Washington. Odriozola and Carrera had both bragged in a similar unguarded way to Mir, who had no need to know.

When he was younger and fitter, Fidel would never have made such a fundamental error. But as he aged and began declining mentally, he was driven more powerfully than before by narcissistic excess. He sought gratification and congratulations. He wanted others to know of his accomplishments. If, as I suspect, he boasted of his super-mole Montes, he may have provided some identifying information; for example, that it was a woman or an American of Puerto Rican descent. One of the Cubans who heard him, duly impressed and perhaps later a defector, may have provided that information to American authorities. It would have been considerably more than the tidbit the Defense Intelligence Agency investigator cited, and it would have set in motion the counterintelligence dragnet that snared Montes.

If this is correct, ironically it was Fidel Castro, the infirm supreme spymaster, the modern world’s most venerable and intuitive intelligence boss, who compromised one of the most valuable secret agents he ever handled. There is a strange justice in supposing that Cuba’s seemingly infallible, prescient, and Machiavellian leader for so many decades could have in the end failed so abjectly. But I believe this is exactly what happened.

TOO ILL TO CONTINUE AS PRESIDENT, Fidel stepped aside provisionally in July 2006 and definitively in February 2008. Today, eighty-five years old and rarely seen in public, his continued decline is irreversible. Meanwhile, his legacy is being cautiously dismantled, his enormous failures on the home front implicitly acknowledged by his successors. Under the presidency of his brother Raúl, the emphasis has been on bread rather than revolutionary circuses, on problem solving at home rather than global grandstanding. Raúl has assembled a new leadership team nearly entirely of his own choosing.

Fidel no longer serves as supreme spymaster. Intelligence operations are now in the hands of distinctly lesser men, bureaucrats and military officers for whom the long covert war with the Americans cannot possibly have the same exhilarating meaning as it did for Fidel. War with the Yankee imperialists was always his personal crusade, the unyielding raison d’être of his revolution. As long as he lives and his brother rules Cuba, the conflict he wanted and needed will be honored in Cuban propaganda, but it will never again determine nearly everything else in national policy.

Raúl has little firsthand experience in the intelligence operations and conspiracies Fidel thrived on. He is more cautious and pragmatic, and he has always delegated responsibilities. Not ruled by lifelong vendettas, he is less inclined to order the executions of enemies or traitors. When he speaks in public, he does so softly, with none of the pageantry or vitriol that accompanied Fidel’s performances. Raúl pays lip service to his brother’s hatred of the United States and the need for continued vigilance—as if recent administrations in Washington were still plotting coups and assassinations—but he clearly has higher priorities than baiting and condemning the Americans. When Fidel is gone, the anti-Yankee obsession will likely expire with him.

Eighty years old as I write these words, Raúl is unchallenged in power and likely will rule until he too falters physically or mentally. His health, like Fidel’s, is a state secret, but the odds are high that he also suffers from serious ailments and debilities, some no doubt related to his decades of heavy drinking. The greatest burden on his leadership, however, is the fact that Fidel is still alive, still issuing “reflections” that are circulated by the Cuban media. Probably they are composed now by others in Fidel’s entourage, which suggests that a hard-line, fidelista sect still is powerful in the leadership. These commentaries rarely critique Raúl’s decisions, but it is also clear that the younger brother self-censors in order to avoid that. As much as he might like to, it is extremely unlikely that Raúl will flatly repudiate any of Fidel’s sacrosanct policies of the past while his brother lives.

Boxed in this way, Raúl has focused on remedying Cuba’s dire economic crises. More than five years in power in his own right, however, he has little to show for the effort. He has publicly promised some radical changes—such as laying off as many as a million public sector workers—only to retreat, no doubt fearing public unrest. He has talked incessantly about implementing agrarian reform, but here too his measures have been halfhearted and cautious.

He is tough—though not as ruthless as Fidel always was—in dealing with Cuba’s small but valiant internal opposition. Pro-democracy groups, independent journalists and librarians, and a world-famous blogger, among many other scattered voices of dissent, continue to pressure the regime, especially by bringing international scrutiny to its appalling human rights record.

Raúl will continue to cast about for ways to force efficiencies and reduce expenditures. He knows how perilously close to economic calamity Cuba balances. If the enormous subsidies provided by gravely ill Venezuelan president Chávez should end, the lights in Havana would literally dim and a severe recession, like the one that occurred after the collapse of Soviet subsidies, would be inevitable. In this climate of uncertainty and cost-cutting, the virtually unlimited resources Fidel devoted to intelligence functions have probably diminished. I am not aware of accurate estimates of the number of active Ministry of Interior or intelligence personnel today, but it is likely that foreign intelligence, at least, has endured cutbacks through early retirements and reassignments.

Capabilities have all but certainly diminished. Raúl’s cronies, the elderly military officers who now run intelligence, are pale, plodding successors to the swashbuckling Redbeard and his founding generation of inspired, audacious operatives. The new leadership is more on the defensive because it faces more determined American counterintelligence efforts than ever before. Many Cuban operatives must doubt the urgency of their missions as they confront the American enemy that cannot possibly seem as threatening as it did before. Faltering morale would be one of the worst consequences of all the new challenges and constraints Cuban intelligence faces. That explains why the regime maintains a deafening drumbeat of propaganda in support of the Wasp spies in American prisons.

Some of the defectors who have been quoted in these pages believe that until the 1989 Ministry of Interior purges, intelligence professionals were the most sophisticated, enlightened, and progressive elite in Cuba’s governing apparatus. Many in the DGI were attracted to the reform movement that fractured the communist bloc between 1989 and 1991, and some officers may actually have plotted against the Castros. I have asked some of my defector sources if the service, now known as the Intelligence Directorate (the DI), could someday be the wellspring of reformist dissent and lead the way to a pluralist, entrepreneurial, even democratic Cuba. Alternatively, might some wily and barnacled intelligence veteran employ his guile, and that of colleagues, to rise to the top of the political heap? It happened in Russia.

The answers vary, but generally my sources conclude that the innovative, iconoclastic spirit they remember when civilians ran intelligence has been muffled during the last twenty years of military dominance. On balance, then, the defectors I consulted are inclined to speculate that a hard-line, authoritarian leader is more likely to emerge from the Cuban military or intelligence services than a democratic reformer. I imagine they are right.

Some of the more extreme DGI practices that Fidel demanded in his day— pumping sleeping gas under closed doors, running a personal squad of assassins, hunting down prominent foreigners—may well have been abandoned by new, more cautious Ministry of Interior chieftains. Only time, and tough American counterintelligence efforts, will tell, however, just how aggressive and creative Cuban espionage remains. Until there is a comprehensive normalization of relations with Havana, however, it would be folly for American officials again to underestimate Cuba’s remarkable foreign intelligence abilities.

Somewhere along that inevitable path toward reconciliation—which now cannot be too far in the future—I hope that a Cuban comes forward with evidence to corroborate what Tiny Aspillaga told me about his memory of the morning of November 22, 1963. Confirming that Fidel knew of Oswald’s intentions to shoot President Kennedy—and did nothing to deter the act—would not stifle the warring among rival assassination conspiracy theories or dissuade those who insist that Oswald did not act alone that day. But additional evidence from somewhere in Cuban archives, from Luisa Calderon, or from another Cuban witness would confirm what I now believe was Fidel Castro’s most despicable decision during his nearly five decades in power: to stand aside, build an elaborate alibi, lie and dissemble, launch decades of disinformation pointing at others, all the while maintaining a conspiracy of silence about the murder of John F. Kennedy.