THE QUEEN OF CUBA, PART 1: FOREIGN POLICIES

True Spies, Episode 158 - The Queen of Cuba, Part 1: Foreign Policies

NARRATOR: This is True Spies, the podcast that takes you deep inside the greatest secret missions of all time. Week by week, you’ll hear the true stories behind the operations that have shaped the world we live in. You’ll meet the people who live life undercover. What do they know? What are their skills? And what would you do in their position? I’m Sophia Di Martino, and this is True Spies, from SPYSCAPE Studios.

PETER LAPP: She figured early on that the most secure way to do the act of espionage was to memorize. There's no technology that will thankfully read people's minds.

NARRATOR: The Queen of Cuba, Part 1: Foreign Policies. Like everything in Washington D.C., lunch is political. That’s especially true here, on this day, in 1992. You’re looking at a nondescript Chinese restaurant, a stone's throw from the DC metro. Easy to get to, easy to leave. And if you were to sidle through to a seat in the restaurant’s dining room, you’d find yourself in unusual company.

PETER LAPP: Every two or three weeks she would meet in person at a restaurant and they would sit down and have lunch one-on-one for two or three hours in broad daylight, really hiding in plain view. 

NARRATOR: ‘She’ is a serious young woman, around 35, in a hushed conversation with a male companion. A friend, perhaps - but more likely a colleague. There’s no hint of flirtation here - no swapping of sweet nothings. But look closely, at just the right moment, and you might bear witness to a far more meaningful exchange. A gift from her to him. A secret.

PETER LAPP: She was meeting in D.C., which was incredibly rare - an illegal intelligence officer. It really shocked us when we found out from her that she was meeting in person with the Cubans and committing espionage literally over the course of lunch.

NARRATOR: Check, please. You’re about to meet one of the most notorious double agents in the history of US intelligence.

PETER LAPP: She does rank up there with the Hanssens, the Ames, and the Snowdens. 

NARRATOR: A spy so effective that she was able to operate with impunity for 17 years.

PETER LAPP: She, in a perfect world, should have been detected far earlier. The question is whether she could have been detected far earlier. 

NARRATOR: Her name is Ana Belén Montes. From 1985 until her arrest in 2001, she used her position at the US Defence Intelligence Agency to funnel classified documents to Cuba. Drunk on a potent cocktail of arrogance, intelligence, and ideological fervor, Ana pushed herself to the limit in her mission to undermine the American government.

PETER LAPP: Every day she went to work at DIA, working for, in her words, the war machine, it was torture.

NARRATOR: This is one of the men who brought her to justice.

PETER LAPP: My name is Pete Lapp. I'm a retired FBI special agent. I worked with the FBI from 1998 until 2020, and I was focused mostly in my career in counterintelligence and espionage. The Montes case for me was a career case. It was an accomplishment that I was a part of that I never, never topped. 

NARRATOR: Pete first heard the name ‘Ana Montes’ in the year 2000. By then, she’d risen through the ranks at the DIA to become one of the US government’s most well-respected Cuba analysts. But let’s rewind. Who is Ana Montes?

PETER LAPP: Ana was born in Germany on a military base. Her family is American. They are Puerto Rican by descent. Upper-middle-class family. They moved around a little bit because their father spent time in the Army as a psychiatrist.

NARRATOR: By Ana’s teens, the Montes clan was settled in Rockville, Maryland. After a childhood marked by a domineering father, Ana left for college in 1975. 

PETER LAPP: She went to the University of Virginia to get her undergraduate degree in international affairs.

NARRATOR: Two years later, Ana seized the opportunity to see more of the world.

PETER LAPP: She studied abroad in Spain and met a gentleman who was pretty radicalized and they actually had a romantic relationship for a period of time.

NARRATOR: This gentleman, an Argentinian living in Madrid, was a vehement critic of the USA’s foreign policy. Only four years earlier, in 1973, a US-backed coup had overthrown Chile’s leader, Salvador Allende. It was not the first time that Washington had moved to undermine governments that might align themselves with the USSR. It certainly wouldn’t be the last. Already a supporter of Puerto Rican independence, Ana was not difficult to convince. She returned to the US with a deepening sense of injustice. Nonetheless, she needed to eat. As an international affairs graduate, she found a steady job as a clerk at the Department of Justice, dealing with Freedom of Information requests. The role was relatively junior but still required a clearance. Three years in, she began juggling her DoJ role with a new course at the School of Advanced International Studies at the prestigious Johns Hopkins University. 

PETER LAPP: And there she worked on a Master's Degree in international affairs and was in the process of charting out her professional ambition to go work at something like Human Rights Watch or Amnesty International, one of these other government agencies that do good work in the world. That was her ambition until she met a woman at Johns Hopkins.

NARRATOR: At Johns Hopkins in the early ‘80s, Ana was surrounded by students and academics who stood in opposition to America’s role in Latin American conflicts. At the time, President Reagan’s support of the right-wing ‘Contra’ rebel groups in Nicaragua against the Marxist ‘Sandinista’ government was a hot-button issue.

PETER LAPP: She vehemently disagreed with Ronald Reagan's policy. And her attitude was, “How dare the United States dictate how a foreign country should run itself?”

NARRATOR: Fellow student Marta Velasquez shared Ana’s views on America’s dealings with the south. 

PETER LAPP: Back in the ‘80s in graduate school, there was the ratio of men versus women that was probably heavily skewed toward men. So Marta and Ana, being both women and Puerto Rican, just naturally drew themselves to each other in an academic environment. 

NARRATOR: But Marta’s friendship came with strings.

PETER LAPP: Marta already had a relationship with the Cuban intelligence service.

NARRATOR: Famously, the US had tried and failed to overthrow the communist regime in Cuba. Diplomatic relations between the two countries had ceased. Now, the island nation offered assistance to Nicaragua’s embattled socialist government. Sometime in 1983, Marta had written an essay that praised Fidel Castro. The DGI - Castro’s foreign intelligence agency - had taken notice and tasked her with identifying other promising students with pro-Cuban sympathies. Ana Montes fit the bill. Over a period of months, Marta earns Ana’s trust. It’s a process that intelligence officers call ‘development’. If you’re a regular listener to True Spies, you’ll know that it’s the third stage of the so-called ‘SADRAT’ process. Spotting. Assessing. Developing. Recruiting. Agent Handling. Termination.

PETER LAPP: Obviously covertly, she was in the process of spotting and assessing. And here comes this amazing woman, Ana, who's brilliant, super intelligent and already has a clearance. And - oh, by the way - is very angry at US foreign policy in a very critical part of the world. So, the right place at the right time. They become friends and in fact, friends that are significant enough to meet each other's families. There are photographs of Marta at family gatherings of Ana’s where her brother, her sister, and her mother are all attending. So a very deep personal friendship.

NARRATOR:  After graduating in 1984, the young women stay in touch. On a cloudy day in December of that year, Marta suggests that the two of them take a trip together.

PETER LAPP: She finally asks her, “Look, I've told a friend of mine about you. He's a Cuban diplomat working in New York, and he would like to have dinner with the three of us.”

NARRATOR: Remember, at this point in time, relations between the US and Cuba are so strained that neither country has an official embassy in the other.

PETER LAPP: Ana had a clearance working at the Department of Justice. And this was not a dinner meeting that would have been authorized and approved by her employer.

NARRATOR: What Pete’s saying is that Ana really should have known better. 

PETER LAPP: And she didn't hesitate at all and took the train with Marta up to New York City and had dinner with a Cuban diplomat who obviously was also an intelligence officer.

NARRATOR: Unbeknownst to Ana Montes, it would be the first of many such meals - meals like the one we eavesdropped on at the start of this episode. After that fateful conversation, it was official - she was a recruited agent of the Cuban DGI. In March of 1985, Marta, then an employee at the Department of Transportation, suggested another getaway - one a little further afield. 

PETER LAPP: It's a covert trip. And it's an illegal trip.

NARRATOR: Marta and Ana were headed to Havana. But flying direct was off the table. 

PETER LAPP: It is against the law to travel to Cuba in that period of time, especially for the reasons they were going. 

NARRATOR: No matter - the freshly-minted spies had a workaround. Ana had studied in Spain - returning to her old European stomping ground was unlikely to raise eyebrows at the DoJ.

PETER LAPP: They actually communicated with the family that they were in Madrid and going to spend some more time. So, to my mind, Ana uses some of her family members as cover, operational cover for going to Cuba. 

PETER LAPP: They traveled in their true name to Madrid. They then traveled to Czechoslovakia, and there they met with the Cuban intelligence service in a safe house. 

NARRATOR: In Prague, Ana got her first taste of real spycraft.

PETER LAPP: The folks they meet with give them fake passports and wigs. And then they fly directly from Czechoslovakia to Havana. Once there, they receive the basic Cuban 101 how-to-be-a-spy training that would help launch her and help her accomplish what she needed to accomplish over the next, at least, several years.

NARRATOR: Tradecraft, in other words. Surveillance detection and how to lose a tail. The ins and outs of high-frequency radio communications. Encryption. They also learned how to pass a polygraph test - an essential skill if the women were to climb the ranks of the US government apparatus. The Cubans had taken a risk in recruiting Ana. But they saw it as an investment in a bright young woman with a promising future. As investments go, it would prove to be a savvy one. That summer, Ana applied for an analyst position at the Defense Intelligence Agency.

PETER LAPP: So the Defense Intelligence Agency is the intelligence wing for the Department of Defense. They collect military intelligence. They try to get an understanding of the plans, capabilities, and intentions of foreign military services so that when we do go to war, the Department of Defense has its own intelligence component that is collected and analyzed.

NARRATOR: Ana’s qualifications and obvious analytical talent impressed the DIA. She was hired, despite her history of open criticism of American foreign policy, a fact that made her first assignment all the more ironic.

PETER LAPP: So she didn't work Cuba initially. Nicaragua and El Salvador were much higher priorities. We had troops there. We had folks that were fighting a guerrilla war. So her first assignment was on the El Salvador target. And for the first seven years of her career at DIA - and for the first seven years of her career committing espionage - she worked not Cuba, but El Salvador and Nicaragua.

NARRATOR: Remember, Cuba is funding the leftist opposition to US-backed rebels in these areas. The outcome of those conflicts will serve to strengthen or weaken Havana’s influence in Latin America.

PETER LAPP: Clearly, she was providing classified information to the Cuban government about what we were doing in El Salvador and Nicaragua. And there's no doubt that the Cubans would have shared that with the Sandinistas. They were getting very good intelligence from her, and the last thing they would do would take that intelligence, read it, and go, “Wow, this is really interesting” and stick it into a drawer. 

NARRATOR: This was just the first rung on the ladder. But Ana committed to growing her influence within DIA - all to the betterment of Cuba. Around this time, she publicly cut contact with Marta Velasquez. That way, if one of the spies were caught, they’d be less likely to implicate the other.

PETER LAPP: I think once she started working at DIA, her personality changed to a degree. She became laser-focused on building her career to the point where she could get access to as much information. And therefore everything she did was to enrich her career so that she could get to know as much information as possible 

NARRATOR: We don’t know the exact details of the information Ana leaked to the Cubans during this period. What we do know is how she did it - and that’s what’s really remarkable.

PETER LAPP: She's an incredibly bright woman. So, academically very, very smart. She figured early on that the most secure way to do the act of espionage was to memorize. 

NARRATOR: Using techniques like visualization and mnemonic devices, Ana trained herself to process and store reams of data in an unhackable hard drive - her brain. 

PETER LAPP: There's no bag check. There's no security system. There's no risk of getting caught with a spy camera or standing at the copy machine copying sensitive classified information. There's no putting a disk into a computer system. There's no technology that will thankfully read people's minds. And therefore, it's as near-perfect a methodology as I've ever seen. 

NARRATOR: At first, Ana met sporadically with her Cuban intelligence contacts in New York. As the years went by, she requested a change of scenery.

PETER LAPP: She was meeting in D.C., which was incredibly rare. 

NARRATOR: Washington D.C. - the nation’s capital, and the epicenter of the American intelligence community. Over egg rolls and chow mein, Ana fed the Cubans more than a delicious Chinese meal. Ana was operating in plain sight at great personal risk.

PETER LAPP: And then, in this lunch meeting, she would provide them an encrypted disk that would contain classified information and national defense information that she had collected over the previous two or three weeks.

NARRATOR: And so it went, month after month, year after year. Ana’s career went from strength to strength. 

PETER LAPP: She was seen as an incredibly exceptional analyst, highly talented, highly skilled, not well-loved but respected in terms of her analytic capability. 

NARRATOR: By 1992, she was due a promotion - from both of her employers. Around that time, Ana’s focus at DIA changed from Nicaragua and El Salvador to Cuba itself. 

PETER LAPP: She's doing this exceptional analyst program as far back as 1992, working on Cuba, on this collateral project, studying the Cuban military, actually meeting with Cuban military generals. They all facilitated this so she could do interviews with them, which was rather unprecedented. And certainly, I think the Cubans gave her that kind of access to help show DIA how important she is and how important she could be so that she could pivot to work Cuba full time so that that would be a much bigger help to them from an espionage perspective.

NARRATOR: After the fall of the Soviet Union, Cuba was vulnerable. Moscow had funneled training, arms, and funds into the island nation for decades. Now, the Cubans needed more from Ana - more information, more often. This meant that Havana needed to be able to contact Ana more easily. A covert lunch every few months would no longer suffice. 

PETER LAPP: So the high-frequency messages began in 1992, seven years into her espionage. 

NARRATOR: Using old-school radio equipment, Ana was able to tune in to special broadcasts known as ‘numbers stations’. 

PETER LAPP: These are encrypted high-frequency messages that are in Spanish voice using numbers.

NARRATOR: Each message began with an identifying phrase: “Attention. Attention.” A string of numbers would follow, an encrypted message. 

PETER LAPP: And then she would have the corresponding decryption software that would allow her to read the messages that she was receiving through the numbers.

NARRATOR: A Toshiba laptop, loaded with specialist software by the boffins in Havana, was sufficient to run the decryption.

PETER LAPP: These were on predetermined days, predetermined times of the day, and predetermined frequencies that anyone could listen to if they knew. The guy she sits across the table with at lunch is really just a means to an end. I mean, he's important because he cares about her. He's that personal connection to her. But the folks that are reading her intelligence and understanding, trying to understand what it is, they're able to communicate to her via high-frequency messages. Those meetings occurred in conjunction with high-frequency messages. She would receive a couple of messages a month on average. And then a follow-up; “Hey, we read this. We're kind of confused about that. Can you explain this?” 

NARRATOR: Even today, shortwave radio enthusiasts enjoy tuning in to these mysterious stations. Some tradecraft is timeless. And that’s good news for Ana. In 1994, she’s polygraphed for the first time.

PETER LAPP: It's her first and only polygraph that she had at the DIA and it was completely random. When she applied to DIA, they did not have a polygraph program. 

NARRATOR: By now, Ana has been spying for Cuba for nearly a decade. Her initial anti-polygraph training in Havana must feel like a lifetime ago. Now, a routine lie-detector test could put all that at risk. But this True Spy has a talent for memory. She aces it. But then again, nobody seriously entertains the notion that the Cuba desk’s star analyst might be working for the other side.

PETER LAPP: How could someone of such acclaim and accomplishment and proficiency be committing espionage? It became this balance where her reputation, I think, helped insulate her from scrutiny from colleagues and anyone who may be thinking that there was a reason to be concerned.

NARRATOR: But nobody is infallible. In 1996, a crisis at the Defense Intelligence Agency put the spotlight squarely on Ana Montes. The Cuban government has shot down two planes. Both aircraft are carrying civilians, members of an American non-profit called Brothers To The Rescue.

PETER LAPP: It's a huge crisis for the relationship and for the US government. 

NARRATOR: Brothers to the Rescue was founded in 1991, by Cuban exiles in Miami, Florida. Made up of a team of volunteer pilots, its mission was to assist and rescue refugees emigrating to the United States. 

PETER LAPP: For years, the Brothers to the Rescue had been flying mostly in international waters, but sometimes over Cuban airspace, looking out for rafters, people that are fleeing on rafts and then trying to contact the Coast Guard, the US Coast Guard, to give them information to help rescue these folks, because many, many people perished trying to flee Cuba in the Straits of Florida.

NARRATOR: By the mid-90s, the organization was dropping leaflets into Cuba in an effort to spread its anti-Castro message.

PETER LAPP: The Cuban government had started warning the US government about the Brothers To The Rescue. 

NARRATOR: The message from Havana was clear. Any further incursions by American planes, civilian or otherwise, would not be tolerated.

PETER LAPP: There was timeliness about a significant alert beforehand, but not enough time to really get that information down to the Brothers to the Rescue from the US government, and then two days later, Cubans, in cold blood, shot down two planes and killed four unarmed planes in international waters. And these were four American citizens.

NARRATOR: At best, this was a severe international incident. At worst, it was an act of war.

PETER LAPP: The day after the shootdown, Ana is called into the Pentagon because it's a crisis and it's all hands on deck if you're working Cuba. 

NARRATOR: Ana is an ideologue, an agent of conscience. She’s dedicated almost 12 years to working against US intervention in Latin America. But now there are American bodies in the Strait of Florida. Civilians.

PETER LAPP: And that morning, she and her handler did not have a planned meeting scheduled because it wasn't that particular - every other third weekend or so. But he stood on the corner of her street, on Connecticut Avenue, and knew she would be going to work and made eye contact with her. And she pulled over at a very brief meeting and he said to her something along the lines of, “Look, I know you're headed to the Pentagon. We're going to need to know everything about what's going on.” 

NARRATOR: Amid the panic, this is a major test of Ana’s resolve. How far does her conscience go?

PETER LAPP: This was an opportunity for her to say, “You know what? The killing of American citizens is a bridge too far. I am not in favor of this. And I'll still work with you, but let's take some time off. I'm not going to help you with this. This was cold-blooded murder. “And instead, she said to him, basically, “When and where do you need to meet?” And then every night at the end of the day, after she had left the Pentagon, she would meet with her illegal officer, Herman, and do a debriefing of what she learned that day about where the US government was thinking about going and its response to this unprovoked attack. 

NARRATOR: People make mistakes. Even people like Ana Montes. On the first day of the crisis, her behavior - usually unimpeachable, remember - draws the wrong kind of attention. Reg Brown, a fellow DIA analyst, gets word that Ana has been acting strangely.

PETER LAPP: She left early on the first day, I believe, and she's alleged to have received a phone call. 

NARRATOR: Now, we know that the Cubans were never going to call Ana at work. But the mysterious phone conversation, coupled with an early exit during a time of crisis, is enough for Reg to voice his concerns about the DIA’s star analyst. He turns to Scott Carmichael, a DIA counterintelligence officer - or spycatcher, to you and me. Scott is concerned enough to pull her in for an interview. But Ana plays it cool.

PETER LAPP: It was a Sunday. Her explanation to Scott later is that the cafeteria was closed. She hadn't eaten all day. She was starving and there was nothing else for her to do. So she just let herself out the door. And, in his mind, a lot of what she tells him checks out as making sense. 

NARRATOR: Ana’s name is on Scott Carmichael’s radar. One day, that’ll prove to be an unlucky place to be. But for now, she’s allowed to continue her work unmolested and her star continues to rise.

PETER LAPP: According to the Department of Defense Inspector General report on Montes, they have - unredacted - that she was read into a Special Access Program in May of 1997 that belonged to the National Reconnaissance Office, NRO.

NARRATOR: The NRO is the arm of the Department of Defense that designs, builds, and launches satellites. It’s a crucial source of signals and image intelligence for the US government. Its projects deal with highly classified, multi-million dollar technology. This is the kind of access that represents a huge payoff on the Cubans’ investment. But the late ‘90s are about to become lean years for Cuban spies.

PETER LAPP: So in South Florida in September of 1998, the La Red Avispa network, the WASP Network, was investigated and ultimately arrested by the FBI for espionage-related charges. This had been an investigation that was going on for two or three years. Dates and origins date back to 1995, I believe, and a complex investigation involving multiple, I think, up to 10 people. The arrests in Miami were very damaging to the Cuban intelligence service. It took out a very significant network. Obviously, Montes became concerned about this. I mean, there was a high-profile arrest, which made a lot of national news. I remember watching it on CNN, news of the arrests just after my graduation from the FBI Academy. And it was clearly on her mind and very much a concern of hers and I'm sure elevated her level of anxiety to a pretty significant level by that point.

NARRATOR: Ana doesn’t know it but her anxiety is more than justified. 

PETER LAPP: We found out about Montes, around the same time we learned about the WASP Network and the existence of the WASP Network.

NARRATOR: A few years earlier, the US government had made some new Cuban friends.

PETER LAPP: They had had enough of the corruption of the Cuban regime, banded together, teamed, and created an insider-threat problem for Cuba. We often say in espionage that ‘spies catch spies’. 

NARRATOR: Along with the seeds of the WASP Network investigation, the Cuban defectors had come to the FBI with information about a high-ranking foreign agent within the American intelligence community. An ‘Unsub’.

PETER LAPP: When you have an individual that you don't know who, but you know that there's been a crime committed until you identify that individual, we refer to those cases as ‘Unsubs’.

NARRATOR: Unsub is a snappy contraction of ‘Unknown Subject’. And if you’ve come this far, there’ll be no prizes for guessing who this one is. But at the time, Ana Montes was a ghost - nameless, featureless, even … genderless.

PETER LAPP: The Cubans went to great lengths to disguise her gender. 

NARRATOR: And the FBI didn’t have much to go on. The intelligence community is a big place.

PETER LAPP: We knew we had a penetration within the US government. The Unsub was either at the FBI, at the CIA, or at the Department of Defense. DoD itself has 1.3m uniformed personnel and almost 800,000 civilians. So if you are looking at the Department of Defense for suspects, you had well over 2m suspects just at the Department of Defense. Our suspect pool legitimately was 2.5m.

NARRATOR: And the high-frequency messages that the US government was able to intercept could be picked up anywhere from North Carolina to New England. 

PETER LAPP: We're obviously not worried about DoD folks that are west of the Mississippi, that are over in Korea or Hawaii. But at the same time, we still had several hundred thousand potential suspects. 

NARRATOR: That’s a lot of data to crunch. 

PETER LAPP: And the difficulty about the original source information is the classification level was Top Secret and sharing that with [the] selected few who had a need-to-know. It wasn't our information, number one, it didn't belong to the FBI. And we'd be very careful about who we were sharing this with because we couldn't just put out an all-points bulletin and say, “Hey, the FBI's looking for a Cuban spy who… blah, blah, blah, blah, blah.” We would alert the suspect before we even would identify the suspect. 

NARRATOR: So how to find the one in 2.5m? Next time on True Spies, a brave investigator takes matters into her own hands.

PETER LAPP: She’s kind of a Nancy Drew-type character where she was really trying to figure out this mystery. 

NARRATOR:  And closely-held secrets cause tension in the American camp.

PETER LAPP: So DIA came to the FBI and said, “We have a match for your Unsub.” And the FBI basically said, “Who are you and how did you find out about our case?” 

NARRATOR: I’m Sophia Di Martino. Join us next time for the conclusion to The Queen of Cuba.