For a book Gleijeses was working on about the 1944 Guatemalan revolution and the United States, Velázquez pored over Guatemalan newspapers on microfilm. “We never discussed politics,” Gleijeses told me. “We discussed the work we were doing together. I told her what I was looking for. We would meet once a week or after she had done a number of hours of work. She would give me the printout and we would discuss what she had found,” he said. “She was excellent. I remember Marta as a very pleasant person and excellent research assistant. I have a soft spot for her.”
Kendall Myers taught British politics and European history at SAIS, where he’d earned his doctorate in 1972. Beginning in 1977, he was also an instructor at the State Department’s Foreign Service Institute, where he prepared government employees for overseas duty. At Cuba’s urging, he applied for an analyst position at the CIA in 1981, but was turned down.
Six foot six with a walrus mustache, an accomplished yachtsman and WASP blue-blood whose ancestors included telephone inventor Alexander Graham Bell, Myers was infatuated with the Castro regime. Invited by a Cuban intelligence officer in New York, Myers visited Cuba in December 1978. “Everything one hears about Fidel suggests that he is a brilliant and charismatic leader,” he wrote in his diary. “He has helped the Cubans to save their own souls. He is certainly one of the great political leaders of our time.” He and his wife, Gwendolyn, joined up six months later.
The couple passed information to their handlers by switching shopping carts in crowded Washington supermarkets, and also hooked up with Cuban intelligence in Trinidad and Tobago, Mexico, Brazil, Ecuador, Argentina, Italy, France, and the Czech Republic. His biggest thrill was a four-hour audience in Havana in 1995 with Fidel Castro himself.
Myers received a top-secret security clearance in 1985 and rose to become a senior analyst at the State Department’s Bureau of Intelligence and Research from 2001 to 2007, giving him access to sensitive intelligence. He also coordinated State Department conferences and research projects.
“I would see him once every couple of months” at CIA headquarters, when Myers dropped by to discuss upcoming conferences, recalls Fulton Armstrong, former national intelligence officer for Latin America. “I’d try to snag him for a cup of coffee to lobby him for more conferences on Cuba and Latin America. Not once would he show me a glimmer of interest in anything to do with Cuba.” Perhaps Myers was concealing his fidelity to Fidel.
Chris Simmons, a former specialist on Cuban intelligence at the Defense Intelligence Agency, says that the U.S. secrets Myers supplied to Cuba were less valuable than his assessments of which SAIS students were ripe for recruitment.
Whether Myers recommended Velázquez or Montes to Cuban intelligence isn’t certain. “In my opinion, Myers suggested Rita Velázquez, and Rita suggested Montes,” said García, the former Cuban intelligence officer.
According to her indictment, Velázquez began spying for Cuban intelligence in 1983. That September, she traveled to Mexico City, intending to meet with Cuban agents. The planned rendezvous was aborted because Mexico had just arrested two Cuban officials. She also began cultivating Montes by appealing to their mutual disdain for U.S. policy in Nicaragua. In the summer of 1984, she took Montes to dinner and explained that she had friends who were “looking for someone to translate Spanish language news articles into English” and could fulfill Montes’s “expressed wish to assist the people of Nicaragua.”
Around that time, they finished their studies at SAIS and Velázquez became a lawyer for the U.S. Department of Transportation, with a security clearance. That July, she wrote to Montes, “It has been a great satisfaction to me to have had you as a friend and comrade during this time we’ve spent as students. I hope our relationship continues outside the academic sphere.”
It did. In December 1984, and again in early 1985, they rode by train to New York to see a Cuban intelligence officer. Montes “unhesitatingly agreed to work through the Cubans to ‘help’ Nicaragua,” according to the inspector general’s report. At the instruction of Velázquez, who also supplied the typewriter, Montes wrote an autobiography, describing her Justice Department job. Then, in the spring of 1985, they traveled on false passports via Prague and Madrid to Cuba, where they were given intelligence training in how to receive encrypted radio messages and how to pass lie detector tests that might be required for employment at U.S. intelligence agencies. (Montes later explained that the technique required tensing the sphincter muscles.) Montes applied to the Office of Naval Intelligence, the Arms Control and Disarmament Agency, and the Defense Intelligence Agency. Velázquez gave her a character reference, and DIA hired her as a researcher—a gateway to scoping out U.S. military plans and intelligence activities involving Cuba.
Possibly for security reasons, once Montes established herself at the DIA, she and Velázquez stopped hanging around together—and made sure everyone knew it. “I vaguely remember Marta telling me, they used to be friends, but weren’t anymore. Ana Montes had broken relations,” Gleijeses said. “I would imagine they intentionally broke relations.”
“They had a falling-out,” Emilia Montes said. “They stopped speaking to each other. I don’t know why.”
The rupture “was odd,” said the relative who asked not to be identified. “I had never heard of Ana arguing with a friend before. I’m sure now it was a lie.”
Although Montes had completed her SAIS coursework in 1984, Johns Hopkins withheld her master’s degree in Latin American studies until 1989 because of unpaid tuition. According to Simmons, who helped expose Montes as a spy and debriefed her after her arrest, she “got into a philosophical argument” with the university, insisting that her education should be free. On graduation day, Emilia Montes said, Ana marched with her classmates and received what looked like a diploma sheath but was empty inside. She explained to her mother that she was behind on her bill.
Montes hit up her father, but he refused to pay, Simmons said. Finally, Cuban intelligence stepped in. Making an exception to its usual practice of expecting agents to spy gratis, it covered her bill.
“She met with her case officer and said she owed her tuition and couldn’t pay it,” Simmons said. “The case officer was horrified. Operationally, it puts Cuba at risk. You don’t want a spy with a credit history issue. It’s a security issue. The Cubans paid it not because they wanted to, but because they had to.”
* * *
IN 1994, WITH the personal approval of Fidel and Raúl Castro, Gleijeses was granted unusual access to Cuba’s historical archives. His coup spurred a visit from his former student, Ana Belén Montes, by then the DIA’s top analyst on Cuba, who began asking him for his impressions about Cuba and its military. Gleijeses told her that he wouldn’t share information with her because he opposed U.S. policy on Cuba.
Ostensibly, Montes was seeking his help on behalf of the U.S. government. But Gleijeses later wondered if she was on a mission from her Cuban handlers. Some Cuban officials thought he was a CIA spy and that giving him free rein in the archives was a mistake. Under a pretext, Montes was testing his scholarly independence.
“Once I realized she was a Cuban agent, I thought that perhaps she had been sent by Cuban intelligence to see how I was behaving,” Gleijeses told me. “They wanted to see how I might respond. I clearly passed with flying colors.”
Montes’s dual role in their encounter—ostensibly as a U.S. official, actually as a Cuban agent—illustrates her double life in her heyday. “By day, she was a buttoned-down GS-14 in a Defense Intelligence Agency cubicle,” a 2013 Washington Post profile observed, referring to her federal pay grade. “By night, she was on the clock for Fidel Castro, listening to coded messages over shortwave radio, passing encrypted files to handlers in crowded restaurants and slipping undetected into Cuba wearing a wig and clutching a phony passport.”
Montes enjoyed a meteoric rise to the highest circles of federal policy making on Cuba. She briefed the Joint Chiefs of Staff and the National Security Council, and badgered the
U.S. Drug Enforcement Administration about its investigations of Cuban drug trafficking. She successfully opposed a U.S. military response to Cuba’s 1996 shooting down of two civilian planes, operated by the Miami-based group Brothers to the Rescue, that were releasing leaflets over Cuban territory.
She struck colleagues as aloof and arrogant, but also smart and well prepared, skilled at testing arguments against empirical evidence. “She kept to herself, and showed patience as she developed an argument and hit you between the eyes with it,” Fulton Armstrong recalls. She could puncture another analyst’s long-winded presentation with a brusque “So what you’re saying is you don’t know?”
“Everybody would try to crystal ball what Fidel and [his brother] Raúl are thinking about,” Armstrong said. “She would say, ‘Look, we don’t know. Our views represent our biases more than our facts, and it’s useless to speculate.’” Possibly she eschewed such speculation for fear of accidentally revealing that she did know what Cuban intelligence officials were thinking about, if not the Castro brothers themselves.
Montes is often credited with shaping a controversial Defense Department assessment that dismissed Cuba as a “negligible” threat with “minimal conventional fighting ability.” Congressional critics and Cuban-American politicians attacked the assessment for ignoring Cuba’s support for guerrilla insurgencies and terrorist groups. However, Armstrong says that Montes’s first draft aimed at placating Republicans by hyping the Cuban threat. He and another intelligence official then rewrote it, eliminating the alarmist tone.
Armstrong has searched his memory in vain for clues to Montes’s treachery, “including whether she advocated analytical lines that would serve the Cuban government’s interests,” he said. “But I reached the personal conclusion that she didn’t want to call attention to herself by advocating. If she’d written an exculpatory paper, people would have said, ‘She’s soft on Castro.’”
The U.S. director of central intelligence named her an exceptional intelligence analyst and rewarded her with a year’s sabbatical, on full pay, to study the Cuban military. Her report, which was likely guided by her Cuban handlers, exaggerated the Cuban high command’s interest in a relationship with the U.S. military, according to former CIA analyst Brian Latell.
“I was very impressed with Montes,” said Jorge Domínguez, the Harvard professor of Latin American politics, who met her at a session on Cuban military capabilities. “She was knowledgeable, smart, articulate, and precise. She focused on the facts, without spinning. There was this aura of competence.”
Pinned to the wall of Montes’s DIA cubicle was a handwritten quotation: “The king hath note of all that they intend / By interception which they dream not of.” It was a private woman’s private joke; although Shakespeare was referring to Henry V, the couplet applied equally well to Montes’s “interception” for her king, Fidel. As she ate lunch alone at her desk, she memorized page after page of classified documents on Cuba, which she would type at night in her apartment into her Toshiba laptop. She would transfer the floppy disks to her handlers over dinners at Chinese restaurants in the Washington area, during her Caribbean vacations, and on trips—official or clandestine—to Cuba itself.
She supplied Cuban intelligence with names and biographical sketches of more than four hundred Cuba watchers in the U.S. government, Simmons said. “Montes compromised all Cuban-focused collection programs, calling into question the reliability of all U.S. intelligence collected against Cuba,” Van Cleave, the former national counterintelligence executive, told Congress in 2012. “It is also likely that the information she passed contributed to the death and injury of American and pro-American forces in Latin America.”
“What makes Ana Montes so extraordinary, though, is that she not only had access to the United States’ innermost secrets but also actually created many of the secrets—the highly classified assessments representing what we thought we knew about Cuba,” Carmichael wrote. “Fidel Castro himself might as well have dictated our policy and positions concerning Cuba.”
* * *
WITH THE BREAKUP of the Soviet Union, prospects seemed ripe in the early 1990s for détente between its former satellite, Cuba, and the United States. Many Cuban-American professors longed to connect with the island of their birth. They joined organizations such as the Institute of Cuban Studies and the Cuban Committee for Democracy (CCD), which held conferences both in Cuba and the United States advocating for reconciliation.
The Cuban intelligence service was curious about these groups, wondering if they were sincere or CIA/FBI fronts, and whether it could recruit any of their members. A comment at one Havana conference by Fordham University sociologist and CCD member Orlando Rodriguez, that many Cuban-Americans have dual loyalties to the United States and Cuba, marked him as a possibility. Bearing a gift of fine Cuban cigars, a man whom Rodriguez guessed to be an intelligence officer congratulated him on the remark, calling it “very cathartic for us.”
Back in the States, a diplomat from the Cuban mission to the United Nations, also presumably a spy, dropped by Rodriguez’s office to ask about his views on Cuba and about Fordham. Rodriguez sent him a university catalog and other materials. “As a member of the CCD, which wanted dialogue, I couldn’t say to the diplomat, ‘I don’t want anything to do with you,” he told me. After Rodriguez’s son, an assistant vice president at Cantor Fitzgerald, was killed in the September 11, 2001, attack on the World Trade Center, a staffer from the Cuban mission visited Rodriguez at Fordham again, expressing condolences and discussing events in Cuba.
Likely sensing that Rodriguez wouldn’t help, Cuban intelligence never progressed beyond chatting him up. But, unbeknownst to Rodriguez, one of his friends and fellow academics, Carlos Alvarez, a member of both the CCD and the Institute of Cuban Studies, was a Cuban agent.
Born in Cuba, Alvarez participated in an underground anti-Castro student movement and then fled to Venezuela. He studied for the priesthood but left the seminary for the United States, where he earned his doctorate at the University of Florida. In 1974 he joined the faculty of Florida International University (FIU), which has about seventeen thousand Cuban-American students, the most of any U.S. university. A psychologist specializing in conflict resolution, he sought to apply his expertise to improving relations between his homeland and the United States.
In classic fashion, Cuban intelligence used a fellow academic to recruit him. In New York for an Institute of Cuban Studies meeting, Alvarez began chatting at a party with a Cuban diplomat, who was actually an intelligence officer. When Alvarez said he wanted to visit Cuba to promote dialogue, the diplomat referred him to a Cuban psychologist who could arrange an invitation to the University of Havana, and would also appreciate his insights for a paper she was preparing on the Cuban-American community in South Florida. Alvarez had lunch with her the next day. Her husband was assigned to Cuba’s mission at the United Nations in New York, and soon Alvarez was in contact with handlers there. (In an ironic twist, the psychologist who recruited Alvarez would be convicted in Cuba in 2013, along with her husband, of spying against the regime. She was sentenced to fifteen years in prison, half as long as her husband.)
Alvarez received instructions from Cuba through “personal meetings, messages written on water-soluble paper, coded pager messages, and encoded electronic communications via shortwave radio,” according to court documents. Unlike Ana Montes, Alvarez lacked access to classified documents and high-level federal officials. He supplied Cuban intelligence with various tidbits, including the phone number of an FBI analyst who was one of his students, and an assessment of FIU president Modesto Maidique, a close friend. Although prosecutors said in court documents that Alvarez prepared a report to Cuban intelligence containing “sensitive information” about Maidique’s personal finances and private business ventures, Maidique told me that Alvarez “didn’t have a fucking idea of my finances.”
He said what Alvarez told Cuban intelligence about him was harmless, and they re
main friends. “The totality of information that he provided them was that I was a very proud guy and egocentric, which is not inaccurate,” said Maidique, who described himself as the first Cuban-American university president in U.S. history. “Carlos is one of the finest men I have met in my whole life.” Alvarez is so kindhearted and innocent, Rodriguez told me, that when a prostitute solicited him on the streets of Havana, he tried to counsel her.
With what he later called a “heavy dosage of idealism and naïveté,” Alvarez figured that he could manipulate Cuban intelligence. If he cooperated even minimally, it would let him travel to Cuba and run programs and workshops, fostering unofficial communication between Cubans and Cuban-Americans and liberalizing the Castro regime. “By [the] mid-eighties, I had already identified the intelligence service as a potential change agent in the island,” he wrote. “In exchange for providing them with my analysis and other innocuous information regarding the Cuban-American community in South Florida, I expected to get access to decision-makers in the island, whom I would convince of the importance of establishing the channel for unofficial dialogues. I believed that I could control the situation.”
He didn’t reckon with the FBI. After four years of surveillance, two agents confronted him outside a Miami grocery in 2005. Telling him that it was the most important day of his life, they persuaded him to accompany them to a hotel room for what became a three-day interrogation. They assured him that he wouldn’t be prosecuted if he cooperated fully.
Alvarez confessed, but the agents expected more. “Since you helped the … Cuban government, we want you to help the United States now,” agent Rosa Schureck told Alvarez. “Okay? Do you understand?”
Unlike South Florida professor Dajin Peng, who would later finesse FBI agent Dianne Mercurio’s request to spy on China, Alvarez flatly refused. “I want something else,” he answered. “I want peace in my life.” He pleaded guilty to conspiring to act as an unregistered Cuban agent, and was sentenced to five years in prison.
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