SpyCast 1.24.23
Ep 571 | 1.24.23

“Code Name Blue Wren: Cuban Spy Ana Montes” - with Jim Popkin


Andrew Hammond: Hi, and welcome to "SpyCast." I'm your host, Dr. Andrew Hammond, historian and curator here at the International Spy Museum in Washington, D.C. "SpyCast's" sole purpose is to educate our listeners about the past, present and future of intelligence and espionage. Every week, through engaging conversations, we explore some aspect of a vast ecosystem that looms beneath the surface of everyday life. We talk to spies, operators, mole hunters, defectors, analysts and authors to explore the stories and secrets, tradecraft and technology of the secret world. We are "SpyCast." Now sit back, relax and enjoy the show.

Andrew Hammond: This week's episode is on someone who has been called the most important spy you have never heard of - Ana Montes. For over 17 years, Ana was a Cuban agent at the heart of the U.S. intelligence community, an analyst at the Defense Intelligence Agency, or DIA. She wrote policy documents, advised presidents and generals and had four family members in the FBI, all of whom were loyal patriots, heartbroken by what she did. Our guest is author of a new book on Ana, "Blue Wren." Jim Popkin is an investigative journalist who has worked for many years at NBC and the U.S. News and World Report. He has a very interesting tie to this story in particular. He spent many, many hours in Ana's house in the Cleveland Park neighborhood of Washington, D.C., because his friend would go on to sell the house to a person named - yes, you've guessed it - Ana Montes. 

Andrew Hammond: I'm so pleased to speak to you about your book. And it's very timely because Ana Montes was just released from prison. So for our listeners that haven't heard of her - and in your book, you note that she may well be the most famous spy that you've never heard of - or most important spy you've never heard of. Who was Ana Montes? Why is she significant for the history of espionage and intelligence? 

Jim Popkin: Yeah. So Ana Montes is an American, to start with. And she entered the government working for the DIA - the Defense Intelligence Agency. That is the intelligence arm of the U.S. military. And the reason that I say she's probably the most famous and most dangerous spy no one's ever heard of was because she was arrested right after 9/11 - 10 days after 9/11. And even though it was a very significant arrest, it kind of came and went just because of, you know, the importance of that event. And, you know, it made some headlines, but most folks have never heard of her, as they have, let's say, Robert Hanssen, who was the spy who worked for the FBI and was spying for the Russians, or Rick Ames, the CIA spy, as you know. 

Andrew Hammond: And can you just break that down for us just a little bit? So the DIA - so the intelligence arm of the DOD - how does that relate to Army intelligence, the NSA - well, all of these other parts of the DOD that people have heard of that are involved in intelligence? What are the DIA doing specifically? Or - yeah, just break that down for us, please. 

Jim Popkin: The DIA is a, you know, really big organization - very important. Today, I believe they have about 16,000 employees. And they're - they don't like when I use this analogy, but they're basically the CIA, if you think of it, for the military. And they don't like that 'cause they - you know, they're their own proud agency. But that's an easy way to think of it. They provide intelligence on militaries around the world. So as an example - and this actually came into play with Ana Montes when - after 9/11, when the U.S. government was prepared to go in and invade Afghanistan, it was the role of the DIA to prepare the military. They have plans both just on the shelf for any scenario, but then they obviously adapt based on what's going on. 

Jim Popkin: And actually, Ana inadvertently was assigned to a unit where she was going to be looking at bombing targets for our government in Afghanistan. And that was done by well-meaning people within DIA who didn't know that she was a Cuban spy. At that moment, she was under investigation. The leadership at DIA and certainly the FBI knew that she was a spy, but she had not yet been arrested. And she got promoted to this unit where she was looking - would have been looking at bombing targets in Afghanistan. And I mention that just to say that's the kind of role of the DIA. They - you know, in that case, when we're going to war, they're helping prepare the war actors, if you will, to get ready for a war and give them specific intelligence. 

Andrew Hammond: You mentioned 9/11 there. It's quite interesting the timing of that. Can you just walk us back to the beginning of the story? How did she first get involved in becoming a Cuban spy? Because I know that it's not like she was already in place at the DIA and then she was recruited. She was actually recruited and directed towards the DIA. Is that correct? 

Jim Popkin: Yeah. So Ana Montes actually was born on a U.S. military base in West Germany. She came as a - basically a baby with her sister, Lucy, and her parents to Topeka, Kan. Her father, at the time, was a doctor in the U.S. Army. So they moved to Topeka, Kan. They lived there for a couple of years. And then he left the military and became a psychiatrist, and they moved to the Baltimore area. So Ana, really, for all intents and purposes, grew up in the Baltimore area, in Towson, Md. So she lived there - a great student, very, very bright, clashed with her father - and we can - I'd be happy to talk about that and her very turbulent relationship they had together. And she ultimately went to UVA - the University of Virginia. That's important because, in her junior year, she went to Madrid, spent a year in Madrid, and she kind of got radicalized there. 

Jim Popkin: She was already politically very liberal. But in Madrid in the late 1970s, it was really in the air - like, a very anti-American sentiment at the time. And she fell in with a big group of folks who were very opposed to U.S. foreign policy. And she fell in love with an Argentinean who was kind of a radical - politically - pretty radical guy, and that had a very big impact on her. She comes back. She graduates from UVA. She ends up working for the Department of Justice in their Freedom of Information Act office, and she gets a security clearance there, which is important to the story. She later goes to graduate school at the Johns Hopkins graduate school called SAIS - S-A-I-S. It's in Washington, D.C., on Massachusetts Avenue. 

Jim Popkin: And at SAIS, she falls in with a number of students who also are opposed to U.S. foreign policy in the Reagan era. If you recall that time, President Reagan was very active with the civil wars that were raging in Nicaragua and El Salvador. Ana Montes was strongly opposed to the U.S. intervention at that moment. So she fell in with some folks there - very outspoken. And she met a woman who also was a student at that time. Her name is Marta Velazquez. 

Jim Popkin: Marta was born in Puerto Rico. By the way, Ana's parents were Puerto Rican. And Ana didn't know it at the time, but Marta had already been recruited by the Cubans as an agent. So the two of them become, really, best friends. And Marta convinces Ana at one point to go to New York City - this is in late 1984 - and they have a meal, and she then - Ana is introduced to a Cuban intelligence officer who worked out of the U.N. mission in New York. And Ana makes the decision - she's a young woman. I think she was 27 at the time - to spy on behalf of Cuba. She's working for the Department of Justice - a low-level position, but she does have a security clearance. She and Marta go on a so-called girls trip, where they pretend that they're going to Madrid for fun in the sun and, you know, to hang out in Spain. 

Jim Popkin: But reality, they're met in Madrid by another Cuban intelligence officer, given fake passports. They fly to Prague. And then, from Prague, they're flown with a chaperone, essentially, to Havana. And in Havana, that's where they get their first spy training. And Ana insists, during that visit, that she is taught how to defeat a polygraph because she knows that, when she goes back to the states, that she's going to apply for more important jobs within the intelligence community. And that's what she does. With Marta's help and the Cubans' help, she applies for a number of positions, and she ends up getting accepted into the DIA, the Defense Intelligence Agency. 

Andrew Hammond: And Marta's a Puerto Rican. How does she - how is she involved with Cuban intelligence, or how does she make that connection? 

Jim Popkin: Marta's a fascinating element in this - really bright woman, went to Princeton undergrad, Georgetown Law School and then finished off her career - or academic career at SAIS, getting a master's degree. When she was a senior at Princeton - I read her thesis - she went to Cuba as, you know, an undergraduate. It's believed that she probably ran into Cuban intelligence at that point. And she was already in the tank for Cuba at that moment. She was recruited and met with Cuban intelligence agents even before she was introduced to Ana. So she was kind of an agent in place at SAIS. And that's pretty typical for spy agencies, speaking to you here at the Spy Museum. So they will target graduate schools in the U.S. It's just a really great place for many different spy agencies to meet young, impressionable people and try to interest them in a very low-key way to begin spying. And that's what happened with Ana as well. 

Andrew Hammond: And just for context, for people that are not familiar, SAIS is really one of the leading places that you can come to study foreign relations, U.S. foreign policy and the world, really, isn't it? And it's right here in the heart of Washington, D.C., and has had lots of people that were policymakers or would go on to be policymakers involved with it. 

Jim Popkin: Yes, absolutely. And, you know, they include even Madeleine Albright, who obviously became our secretary of state. It's a very prestigious place. And that's - if you're interested in foreign policy, it's, you know, one of the top schools where you would go to. And that's why spy agencies are attracted to it. 

Andrew Hammond: And this is quite interesting. I don't think it's something we've discussed before on the podcast, but are there - so you have these people coming to these graduate schools in places like Washington and then Washington's a city of espionage and intelligence. So there's people there maybe looking to recruit people, but what is the - is there a counterintelligence component to that? And then that's quite interesting to think of, as well. You're just some idealistic want-to-be grad student, and you turn up, and there's an intelligence game that's taking place in the background you don't - you may not even know about. 

Jim Popkin: Well, that's one of the things that I just absolutely love about Washington in general is the spy-versus-spy kind of cat-and-mouse game that happens behind the scenes that, you know, you wouldn't really be aware of. The FBI is definitely cognizant of this, that our graduate schools in the U.S. are great targets for spy agencies, and they try to keep an eye out for this. But, you know, obviously, we have freedom of speech, so young students can express whatever views they want. It is interesting, more from the SAIS point of view, they've - they had two Cuban spies there at the time. And somewhat unrelated, there also was a professor there named Kendall Myers. He's in prison right now. He was arrested as a Cuban spy. They were all there at the same time. So I don't know what SAIS is doing to keep an eye on this, but they do have an issue. 

Andrew Hammond: OK. Wow. And it's quite interesting to me, the Ana Montes story, as well. So we've got born in Germany, a couple of years in Topeka, Kan., and then we've got Baltimore, Md., area. And then the - a lot of the story is really a District of Columbia or the surrounding area story, isn't it? She lives in Northwest Washington, her drop box is a couple of neighborhoods over, she works at the Bolling Air Force Base in - just over the river. I think that's a fascinating part of the story that a lot of it is located in and around Washington, D.C. 

Jim Popkin: This is a quintessential Washington story, as you mentioned. She lived in Washington, the Cleveland Park area, in a condo building right by the zoo in Washington. She works at DIA, which is in Anacostia in D.C. She's at graduate school at SAIS, which is in Washington, and all the areas where, ultimately, the FBI is keeping an eye on her, surveilling her, it's all in Northwest Washington. So it is - it's a perfect Spy Museum location. 

Andrew Hammond: So just a little bit more background before we start digging into everything a little bit more. So it's quite interesting to me, you know, the queen of Cuba, she's called somewhat derisively by some people, she's an ideological spy on behalf of Cuba. But one part that I'm just unsure about in terms of the motivation is so she's an ideological spy. Initially, when I came across this story and I heard that she was an ideological spy, I assumed there was some kind of Cuban ancestry there. But her grandparents were from Spain. Then her parents were from Puerto Rico. So there's not a Cuban family connection. Is it because she is a communist or is it just because she's anti-U.S., anti-imperialist in her mind, or, like, what's the ideology that she's attaching herself to? 

Jim Popkin: So her - yeah, her family goes back a long time in Puerto Rico. And you could look at - there's some members of the family who were very opposed to U.S. policy and politically very, very liberal. But I really think that her rationale for this had to do with more contemporary politics. She was vehemently opposed to the Reagan-era aggression, particularly in Latin America. 

Jim Popkin: But starting when, as I mentioned, in her junior year abroad in Madrid, she really got a sense of how the U.S. from, really - I think she said from 1898 to present, how the U.S. has comported itself around the world. And she was very uncomfortable with that. I can't say she was a communist, but she absolutely had communist sympathies. She may argue the point a little bit and say, well, I am really more of a socialist. But she was opposed to U.S. policy. She believed in the Cuban mission, if you will, and what Castro was trying to accomplish in Cuba. And that's what she wanted to see. There's certainly some anti-American sentiment in her. 

Jim Popkin: And it's fascinating that once she gets to DIA - think about this. If you have anti-American leanings and then you go and you work not just for the U.S. government - let's say the State Department - you work for the military. She is surrounded all day by people in uniform, and they're carrying out the mission of the U.S. around the world. That was upsetting to her and helped to explain why she was so dismissive of people. She was a very difficult personality. She was called the Queen of Cuba behind her back in a - as you said, Andrew - in a derisive fashion. And it helps explain - if every day you're going into work, and you're seeing these people she called the war machine around her - she couldn't stand them. 

Jim Popkin: And yet, as a good spy, if you look at - this may sound trivial - but if you look at her hairstyle and how it changed, as a younger woman when she was at UVA and even in graduate school, she had long kind of flowing hair. She had - a couple of photos she looks like Farrah Fawcett, that kind of hair in that era. As she enters DIA, she changes. Her clothing changes. It starts to look much more formal, conservative, more military-like. And her hairstyle - she cuts her hair short. And she starts to fit in, like a good spy, with all the folks around her. But during that whole period, she can't stand the people that she's surrounded with and all these people in uniform. 

Andrew Hammond: It's quite interesting to me to compare her to other spies. So, like, Kim Philby, one of the main members of the Cambridge Five - so five undergraduate students who were recruited by Soviet intelligence in the 1930s. When he becomes a communist, he's told to start leaning towards the right to fit in, like Ana Montes, to seem more conservative, more wedded to the regime and the U.K., et cetera. But he doesn't let his personal inner feelings bubble forth or come to the surface. But one of the things that undoes her in the end is that she makes these comments. She has this reputation as someone that makes these comments about American foreign policy or shares her personal views or maybe just lets some things sneak out occasionally. 

Andrew Hammond: So she does look the part, but she doesn't always speak as someone that is corresponding to the part that she's trying to project. So I just wonder if you could tell us what's going on there. I mean, not everybody can be as good a spy as Kim Philby. But, like, how did that happen? Did she not recognize that passing the polygraph and looking like she could fit in was only one part and the other part of it was just keeping her thoughts to herself? 

Jim Popkin: She was very careful about how she conducted her business. Early on, she did make an error. When she was at the Department of Justice, she confided her true feelings to someone. We don't know the name of this person. But someone came forward - one of her colleagues at DOJ - and told - during her background investigation with the FBI - told the FBI that this person, this colleague, thought that Ana Montes was disloyal to the United States. That was an obvious red flag that was later discounted. The DIA knew about that, but allowed her to join their agency anyhow. 

Jim Popkin: But as she went on, she became much more careful. She didn't share her personal views. There were instances in meetings where she clearly seemed to kind of favor a Cuban perspective. But she - remember, she - at this point, she's an analyst with the DIA. And it was conveyed in a way in which no one questioned her loyalty. They did question maybe her judgment in supporting some Cuban points of view. Very famously, at one point - I believe it was 1998 - she helped author an analysis of Cuba that was presented to the secretary of defense, ultimately given to Congress, that was - reflected our - the American point of view on Cuba. She was the initial author of this. The summary was that Cuba did not pose a military or even intelligence threat to the United States, which is laughable. Yes, military - they're a paper tiger. I get it. But they have a great intelligence service, trained by the Soviets, and Ana Montes is the best example of that. 

Jim Popkin: Think of how brilliant they were. They find a graduate student with a clearance and help her enter the U.S. military and the intelligence community. And then they sit back and wait as she is promoted, year after year, going up the ladder within DIA and gaining more and more access to classified documents. They're playing the long game. They were patient and really smart about her. And they protected her, too. So I would say just, you know, back to your question, early on, she was indiscriminate in talking about her political views. Later, when she really became a part of DIA and the intelligence community, she was much more careful. She didn't share any personal views with anyone. No one went to social occasions with her. Even with her own family, she became very circumspect and really didn't reveal herself very much. 

Andrew Hammond: OK. And one of the things that I also find really interesting is, in some respects, she's an all-American girl, isn't she? Topeka, Kan., - she's born on a U.S. military base, goes to Topeka, Kan. In her high school yearbook - I like summer, beaches, chocolate chip cookies, soccer and having fun with my friends. I mean, you don't get any more American than that. 

Jim Popkin: (Laughter). 

Andrew Hammond: And she's - she goes to the University of Virginia - of course, very long, you know, history with that school. And then she goes to SAIS, a place that trains lots of future U.S. policymakers. So if you look at her in one angle, she looks every part what she seems to be on the surface - an American girl who's doing the Lord's work for the DIA. 

Jim Popkin: It's a great point. And I'll just add one other factor in there that we touched on. Her father was in the Army. He ultimately retired as a colonel in the U.S. Army. So she grew up watching her father put on the uniform and go into work early, as a young person. Later, he went into private practice and then returned to the Army again. So, yeah, she was an all-American girl. 

Jim Popkin: You know, it's fascinating - I'm sure we'll get into this - but four members of her family ultimately joined the FBI. Her sister Lucy became a translator for the FBI in Miami. That's a fascinating story. Lucy's then-husband was with the FBI in Miami. And then Lucy encourages her sister-in-law Joan and her brother Tito to join the FBI. They both become FBI special agents. So you're right, this is an all-American family who's, you know, unbeknownst to them, living with Fidel Castro's greatest spy of all time. 

Andrew Hammond: We'll be right back after this. 

Andrew Hammond: So let's just contextualize this geographically. So Puerto Rico - a U.S. territory in the Caribbean. Then we've got Cuba, an island not far off of the coast of Florida. And then we've got Florida. So you mentioned her sister working as a translator in Miami. And Miami in Florida is the epicenter of the Cuban American community, and it's also where there's lots of Cuban intelligence officers operating. 

Andrew Hammond: So can you just help us get our heads around that geography a little bit more? So Puerto Rico - is there - are there Cuban emigres there? Did people flee the Castro regime to go to Puerto Rico? Is there a pro-Castro or anti-Castro grouping of people there? Or are the people of Puerto Rico - how did they orientate themselves with regards to U.S. policy in the region? And then flesh out the Florida part for us because there's lots of people that are very anti-Castro in Florida, but it's also a natural place for Cuban intelligence to set up shop. So just help us understand all of that geographical context, please. 

Jim Popkin: Yeah. I think it's important - yeah - to kind of - to set the table here. So Ana's family - her parents, born in Puerto Rico. Ana lives in Puerto Rico briefly after college. Puerto Rico - there's a community there that is upset with what they see as the, you know, colonial shackles that the U.S. holds over the island. And some of them, very forcefully, want complete independence. That's Ana's point of view on this. And it's very interesting. She just was released from prison. She went back to Puerto Rico. That's where she's living now. She has family there, to this day, who are supportive of her. There's also a community there. 

Jim Popkin: You can look on Facebook. There are affinity groups for Ana Montes. They consider her to be a hero and a martyr to the cause. And so there is a - kind of an undercurrent in Puerto Rico of political opposition to the U.S. and also, I would say, an affinity with Cuba. The islands have no real connection except that they support each other and want independence, particularly, you know, some folks, regarding the U.S. So there's - historically, there has been support between these countries among some - I don't want to oversell this - but among some of the population. 

Jim Popkin: In terms of Florida, after the Castro revolution in '59 - right? - yeah - there was a, you know, mass exodus to the United States and many other places. And Miami has become, you know, the titular home for folks who used to live in Cuba. Politically, Miami is important. It's the epicenter for anti-Cuban, anti - really, anti-Castro - beliefs - a lot of very conservative Americans who now are living in Miami and are opposed to the repression and tyranny of the Castro regime. So that is where, totally coincidentally, Ana's sister, Lucy, ended up. And actually the whole Montes family now is in southern Florida, again, somewhat coincidentally. 

Andrew Hammond: And just very briefly, Puerto Rican independence, is that a super fringe group of people in Puerto Rico, or is it 50/50, or is it - yeah, just ballpark, like, where are we with that? 

Jim Popkin: I would say fringe in terms of complete independence. There are many folks that want more, you know, more control, but there are also people that want Puerto Rico to become a state. So I don't know the polling numbers, but Ana's position, which is I want - that we want complete independence, is absolutely a minority position in Puerto Rico. 

Andrew Hammond: So it has some political representation, but it doesn't have two senators, for example, that represent it. 

Jim Popkin: Now you're catching me... 

Andrew Hammond: I'm sorry. That was more of a statement. Sorry. 

Jim Popkin: Yeah. Because the only reason I'm hesitating is because even in - you know, I live in Washington, D.C. We have - it's called shadow representation. They're not full members of Congress or senators. So I'm not sure about that. 

Andrew Hammond: No taxation without representation. So let's move on to the - what she was up to at the time. So she's identified and recruited. She goes to DIA, and then, even though she's an analyst, she learns a lot of operational tradecraft. So black bag operations are involved in all of this, number stations for her to communicate. She wears wigs. She gets fake passports. She learns how to fake polygraphs. She has disappearing paper. So she has all of that part going on. Where is she trained in all of this? Is this the period of time that she spends in Cuba? 

Jim Popkin: Yes. So on her first - she took at least four trips to Cuba in her lifetime - two were unauthorized, two were authorized through the DIA. But on this first trip to Cuba in 1984 with Marta Velasquez, her classmate and another Cuban agent, she learned some basic tradecraft there. She learns how to realize if she's being followed and defeat that. She insists on learning how to defeat a polygraph. She learns how to communicate covertly with Cuba, and that's fascinating and involves shortwave radio, and some other basic tradecraft. 

Jim Popkin: I don't want to oversell. She's not the greatest spy. She didn't learn all the different tools of the trade, but she had enough skills to get by and to be pretty successful for nearly 17 years. She did have water-soluble paper that, you know, would disappear when wet. That's how she kept some of her codes. So she definitely had some of the great, you know, classic spy tools. But she also - there are a couple areas where she was sloppy and needed to up her game, I would say. 

Andrew Hammond: OK. Yeah. I was just thinking there - it's like the difference between doing an advanced first-aid course and going to med school (laughter). 

Jim Popkin: That's a good point. Yes, yes. 

Andrew Hammond: So what were the areas where she could have used a bit of extra work? 

Jim Popkin: She was not great at tech. So it's fascinating. When the FBI, in May 2001 - this is now - she's under investigation. This is the end of her spy career. She's under investigation by the FBI. They get special legal authority to break into her apartment in Cleveland Park. And they go in, they find her shortwave radio, which is how she's getting her messages from Cuba, and they find her refurbished Toshiba laptop. And on her laptop, the FBI gets a mirror image of her hard drive. And couple days later, they read the results, and there's communication back and forth with the Cubans. Part of the communication says, Ana, here's how you delete messages on your... 

Andrew Hammond: (Laughter). 

Jim Popkin: ...Laptop and you have to do this every time we send you something or you open this document. And she didn't do that. She left really incriminating stuff on her laptop. It's really interesting to read this from the Cubans. It's almost like, you know, going to the Apple Store and talking to the geniuses at Apple. This is the tech community in Cuba telling her what to do. 

Jim Popkin: She really wasn't great at that. And that - ultimately, really, that's what nailed her, those messages back and forth that she clumsily left on her laptop. Because the FBI, they followed her for quite a while. They never saw her meet a Cuban. They never saw her pass a document, unlike Hanssen - Robert Hanssen, the FBI spy, they caught Hanssen red-handed. He dropped classified documents in a park in Virginia. That never happened with Ana. They were waiting for it, but it didn't happen. And so that laptop communication is really what convicted her. 

Andrew Hammond: Wow. And it is quite surprising that this is the case because on another level, she really goes above and beyond in terms of her tradecraft. So, for example, she never - this is such an interesting part of the story - she never physically or electronically removes any documents from work. She just memorizes them, which is kind of incredible. And she has books in her apartment how to basically work out your memory, how to do P90X... 

Jim Popkin: (Laughter). 

Andrew Hammond: ...For your memory, which is pretty incredible. So on one level, she's really, really protecting herself more than the vast majority of people because she never physically or electronically removes anything. But then her tech game is sloppy... 

Jim Popkin: Right. 

Andrew Hammond: ...And that's quite interesting. 

Jim Popkin: Yeah. So it is true, she almost never took a document out of the building, which is obviously risky. So here's what she did. She had two jobs. Her day job at DIA, she goes and works, like clockwork, 9 to 5. She takes lunch at her desk and works right through it - really disciplined, efficient and competent person. But while she's there - I mean, it's - her day job is reading classified documents, raw intel from the field and analyzing it, which really meant writing. She was essentially a writer. She would write long-form analysis of what was going on in the world. 

Jim Popkin: It started with Nicaragua and then El Salvador and then she got promoted to the Cuba desk. So that's her job with the government. Excuse me. And that's her day job. Her night job is come home to her apartment in Washington, and she - as you said, Andrew, she has memorized an enormous amount of classified information. And now she types up what she finds to be most relevant into her Toshiba laptop night after night. And this goes on for nearly 17 years, so it's a voluminous amount of information that she's passing to the Cubans. 

Jim Popkin: She had a good - not great - memory. After the fact, post-arrest, the CIA did an analysis of her. They tested her, you know, using the kind of tests that you would - that one would use for psychology, let's say, or aptitude. And they found that she had a good memory but not great. But when I was at her sister Lucy's house in South Florida, Lucy has Ana's books from Washington. You know, they pulled them out - some of her possessions - after her arrest. 

Jim Popkin: So I got to go through Ana Montes' library. And one of the books that I found that was underlined many places is a book on how to improve your memory. So she had a good memory, she made it a lot better, and she used it to great effect day after day, memorizing classified secrets from the U.S. and passing it to Cuba. One good point about Cuba is it doesn't end in Cuba. So when she would pass along secrets to the Cubans, they would - this is their habit - they would either trade or sell that information to Russia and other American adversaries. So it had the potential of going much beyond Cuba. 

Andrew Hammond: OK. Wow. And just briefly, on the numbers stations and the shortwave radio, can you just flesh that out for us? 'Cause this is really, really fascinating. 

Jim Popkin: I absolutely love this technology. And for anyone who's interested, if you just look up numbers station on the internet, you can find great examples of this from around the world. So spy - you know, intelligence agencies have used this method for a long time. And I'll tell you about how Cuba did it. A woman would go into a radio booth in Havana and she would say, atencion, atencion - attention, attention - and then read a series of 150 numbers in Spanish. And this would be broadcast two to three times a week, and Ana knew the frequency and the time. And it would - it was on a loop so it would be repeated. And so she would dial in with her shortwave radio - and for younger folks who don't know, shortwave radios - you can buy one anywhere. They're inexpensive. And it's really cool. And you can listen to frequencies from around the world. So she would dial into this frequency and listen to these 150 numbers. They seem like just gibberish - right? - garbage. But she'd write them down, and then she'd type it into her Toshiba. And she had the means to decode those numbers in her computer. The Cubans had loaded that in. And it told - it revealed a message. It was her weekly orders from Havana saying, good job. Here's what we want you to look into. This is what we're interested in now. 

Jim Popkin: So it was a great way for her to communicate. And it's a safe way for intelligence agencies to communicate to their agents in the field because if you think about it, how would you - as a law enforcement agency, how do you know who's listening in? Anyone at any time can own - legally own a shortwave radio and listen in on a certain frequency. So it's a very safe way and a kind of old-school, reliable way to communicate. And, you know, it's been going on since the Cold War. It really is a Cold War tech that continued to be used into the '80s and '90s by Cuba. 

Andrew Hammond: Wow. And I was just thinking there when you were talking about her memory, if you've got a good memory but not a great memory - I mean, sure, great is always better than good. But if you're doing something for 17 years at a level of 6 or 7, that's a lot of information over... 

Jim Popkin: Yeah. 

Andrew Hammond: ...That period of time, more than you would get at doing a level 10 for five years or 10 years or something. 

Jim Popkin: Right. 

Andrew Hammond: So the fact that she had a good memory, and she made it better but done it for such a long period of time is quite significant. 

Jim Popkin: Yeah. And let me explain why, you know, my - the book is called "The True Story of America's Most Dangerous Female Spy - and the Sister She Betrayed". Why do I say she's so dangerous? Couple reasons. One, longevity - as you point out, Andrew, 17 years - it's a lot of secrets to spill. Number two, she very cavalierly revealed the true identities of Americans working undercover in Cuba. These are presumably CIA agents that were hired by our government to work undercover in Havana. And she revealed their true names. 

Jim Popkin: There's a haunting message that was found on - the FBI found on her laptop from the Cubans. It said, thank you so much for revealing - and the name is redacted. We were waiting for him here with open arms. So she revealed the real name of someone who was headed to Cuba. The Cubans were aware of it, and they were, quote, "waiting for him with open arms." We are not aware of anyone being executed or arrested as a result of that. But this is a dangerous little game to play. And these folks - clearly, their operations were hampered by the Cubans knowing about this. 

Jim Popkin: She also revealed the names of hundreds of other Americans who just worked on the Cuban account through many different intelligence community offices. And then what - another reason why I'm - distinguishes her from Hanssen and Ames and other notorious recent spies - she played a policy role, as well. She wasn't just an analyst or just passed classified information. She, as I mentioned - 1998 - she writes the first draft of our government's assessment of Cuba. And she claims that Cuba does not pose much of a threat, even their intelligence community. So she's got her thumb on the scale. That makes her very unusual. 

Jim Popkin: She also had high-level access. She briefed a president. At one point, she was called in to brief the then-president of Nicaragua, Violeta Chamorro. And think of that - that was - the Nicaraguan war was a Cuban proxy war. They were involved with that opposing the U.S. in that war. Ana Montes goes in to brief the newly elected president of Nicaragua, turns right around and shares all of that information with Cuba. She operated at a very high level, and that's what made her so dangerous. She wasn't just a paper shuffler. She was involved with briefing generals in the U.S. And so she had a very - a larger-than-life kind of role in her spy capacity. 

Andrew Hammond: Wow. I was actually going to go on to the title a little bit later, but maybe we can just clear that up now. Tell us a little bit more about her code name. When I read about her code name, it sounds a little bit more like a World War II code name or something... 

Jim Popkin: (Laughter). 

Andrew Hammond: ...Doesn't it? "Code Name Blue Wren" - yeah, where does that come from? Yeah. Tell us a little bit more about it. 

Jim Popkins: "Code Name Blue Wren" is the code name that is given to the investigation looking for Ana Montes. And that - that's a fascinating story in and of itself. So here's what happened. The NSA, the National Security Agency, played a very important but largely unknown role in this case. And that was one of the things that I got into in the book that had never been reported before. What happens is - and the NSA is our - really, our greatest spy agency, with satellites all around the world and the ability to listen in on communications all over the world. An analyst at the NSA - ironically, a Cuban American - who came here with her family when she was just 6 years old, forced out of Cuba - and they end up in Miami - at one point, she and her team gain access to these shortwave radio broadcasts from Cuba sent out into the world but meant for their agents in the U.S. Again, these are numbers stations broadcasts - right? - so just gibberish - lots of numbers. 

Jim Popkins: But the NSA figures out the - a way to decode these communications. And they see frequent mention of, quote, "Agent S." And they don't know who Agent S is. They don't know what agency. But in context, they realize Agent S has to be a pretty senior person within the U.S. intelligence community. And obviously, they're excited about this, but they also need to figure out who this is. The NSA can't investigate spy cases. That's the job of the FBI. So in approximately 1997 or 1998, the NSA has a big meeting. And they brief the FBI, the law enforcement officials. And it's obviously a classified briefing. But this analyst - I call her Elena Valdes in the book. She's asked that her - she be given a pseudonym. But Elena and her boss and others on the team briefed the FBI on what they've found from these previously coded communications from Havana. And it's a very exciting development. And they report on a lot of these clues regarding Agent S. 

Jim Popkins: They know that Agent S visited Guantanamo Bay, the base in Cuba - U.S. base in Cuba - in a very finite period, within a couple weeks. That's intriguing. They know that Agent S has access to information at a high level and maybe even can figure out who Cuban defectors are - that would imply that this person really operates at a very senior level - and a number of other very specific clues, unusually specific clues. But they don't know the name. They don't even know a gender. And in fact, often the Cubans - for spy reasons and to throw off the enemy, they refer to Agent S as he 70% of the time and she 30% of the time. So all of this information is presented to the FBI. And an FBI agent is assigned to this case. His name is Steve McCoy. And he's the first agent to work on this. McCoy deliberately starts on this but - and I'm kind of tough on him in the book because he doesn't get anywhere for a couple years. 

Jim Popkins: But keep this in mind. The FBI and McCoy - they were worried that the spy, Agent S, would learn about the investigation. So they had to keep it very close-held. They couldn't talk about it with a lot of different American intelligence agencies because they're very worried that the spy would hear about it and flee. So they were cautious. And he worked very slowly and deliberately for a long time. Unfortunately, Elena at the NSA started to get frustrated. 

Jim Popkins: Almost three years went by, and there was no progress. Her feeling was, I gave them these clues, these Easter eggs, very specific. They should be able to figure this out. And she has a personal motivation. She's Cuban American. She hates the Castro regime. She now thinks she's found evidence of a spy within the U.S., within the U.S. intelligence world, and she is determined to get this person arrested. She's - goes back and forth with her FBI contacts. What's going on? Where - how - where are you now? How's it going? And she's treated somewhat dismissively, not by McCoy, but by others. 

Jim Popkins: At one point, she tells me in an interview - and this is the first interview she's ever given in her life - she tells me that the FBI - her contact informs her that the case is closed, that they couldn't go anywhere and the case has been closed. That was inaccurate. I don't know why she was told that. It might be because she was annoying them and the analyst at the FBI who told her that just wanted to get her off of his back. But the upshot was it motivated her. She got really, really frustrated. And in frustration and desperation, she told analysts at the DIA about this open case. 

Jim Popkins: OK, so keep in mind, she had no idea that the spy worked at the DIA. And as we discussed, it turned out that Ana Montes did work there. She started there in 1985. But Elena from the National Security Agency finds out that there's a unit that's pretty smart about Cuba - investigators at DIA. She had never even known this before. She arranges a, quote, "meet-and-greet" at DIA headquarters. And she goes with a number of her colleagues. This is spy tradecraft in and of itself because what she tells them up front is, I don't know much about DIA. I'd just like to come and check it out. Could I have a tour? 

Jim Popkins: She shows up with about four or five of her colleagues, and they meet a DIA investigator named Chris Simmons. And Chris Simmons thinks, well, this is going to be a - just a fun meet-and-greet, and I'm going to show them around, maybe show them the museum. And what Elena says right away - she says, look, this is not a meet-and-greet. I need to share some information with you. Can you put us in a secure room, a SCIF, where - you know, it's like a lead-lined room where you can't listen in from the outside. 

Jim Popkin: And that gets Chris's attention. And he says, sure, let me figure that out - brings them into a meeting room. Elena sits down and plunks down some documents in front of Chris Simmons, and he is absolutely stunned. Elena tells him there's an open investigation by the FBI. There's a spy somewhere. We don't know where it is, and we need your help. Chris sees enough in there to think that this, A, is very interesting, B, perhaps we can help. He informs his boss. 

Jim Popkin: I'll condense some of this. Ultimately, that information is passed to an investigator, another hero of this story, named Scott Carmichael. Scott is essentially a mole hunter, a spy hunter within DIA. That's his job. He's given this information and these very specific tips, and he enters it into the DIA databases, and he very quickly learns that this has to be Ana Montes. Her name pops up on his computer screen. 

Jim Popkin: I'll just give you one example, one area that was helpful. They knew that the spy, Agent S, had been to Guantanamo Bay within a - I think it was about a two- or three-week period in a given year. Scott Carmichael, because he worked at DIA, had a lot of access to travel receipts and also employees at DIA and where they had traveled. And he's able to quickly ascertain that Ana Montes had been to Guantanamo Bay at this same period. Now, he already knew of her and actually had interviewed her. So it was a familiar name to him. But getting that information and confirming that she had been there at the same time as Agent S sent him on a path. 

Jim Popkin: He started to collaborate with Elena at NSA. All of this is happening behind the back of the FBI. They don't know that these discussions are going on. When they're told, they're irate because they're worried, for good reason, that someone is going to learn, that this spy is going to learn. But this investigation is building behind the scenes and without the knowledge of the FBI. And it's Elena and Scott Carmichael and a couple other key folks at DIA who figure out on their own that Agent S is Ana Montes. It's amazing what they did on their own. And they ultimately present that information to the FBI, and the investigation goes from there. 

Andrew Hammond: A couple of just really quick follow-up questions there. So when Elena takes that information forward, does she have the blessing of her bosses to do this, or is this off the books? Does she get rapped on the knuckles afterwards? 

Jim Popkin: It's off the books. 

Andrew Hammond: OK. 

Jim Popkin: And she does, yes. She is threatened with being fired from NSA. And when the FBI finds out about this - and they find out very quickly 'cause so few people knew - an FBI supervisor threatens to prosecute her and arrest her for doing this. She still, to this day, is upset about how she was treated and how she had to go, as you said, you know, kind of off the books to figure out this riddle. And she still harbors a lot of resentment about how she was treated. 

Andrew Hammond: This, like, interagency whistleblower, you know... 

Jim Popkin: Yes. Yes. 

Andrew Hammond: ...Something - right? - but still within the confines of the government. 

Jim Popkin: Correct. 

Andrew Hammond: Yeah. 

Jim Popkin: And she makes the point that what she did was legal and that she had the authority, but she definitely did not have the blessing of the FBI, or even her own supervisors, to do this. 

Andrew Hammond: OK. So just help our listeners understand. You know, you mentioned the mole hunter within DIA and the - their counterintelligence and security office. Why were they not the people doing the investigation in the first place? Or why do they only come into the picture later on when they're the people that could have cleared up so much of the, well, she was at Guantanamo Bay on this day, etc., etc.? 

Jim Popkin: The FBI didn't know where the spy was. They believed that the spy was likely a man because the Cubans had said 70% they referred to Agent S as he. So they believed, well, it's likely a man. And most spies are men. In the U.S. until recently, it was about 90% of all the recent spies that have been identified in the U.S. had been men. So a woman spy is still unusual. As I mentioned, even though they knew that the spy had been to Guantanamo Bay, well, that's a big universe of folks within the U.S. government. 

Andrew Hammond: Sorry, briefly, to interrupt. So they didn't know that it was someone from the DIA at... 

Jim Popkin: Correct. Yes. 

Andrew Hammond: ...This point? OK. Got it. OK. 

Jim Popkin: Yeah. Sorry. Yeah. Yeah, they didn't know where this spy was. In fact, early on, the belief was this must be a CIA officer. So there was no reason to reach out to DIA. You could make the argument that they should have reached out to someone within the Defense Department because Agent S had been to Guantanamo Bay. That's a military facility. It would stand to reason that that would be a good place to start. 

Jim Popkin: But as I said, Agent McCoy from the FBI was under orders to be very, very careful and circumspect about this investigation. He was told that both by the NSA, whose initial tips and information this was, and by his own supervisors at the FBI. It would have been a nightmare if he had been indiscreet about this because Ana Montes would have heard about it. She was a good spy. She had her fingers all over the place in anything having to do with Cuba. And she presumably would have heard about the investigation, and she would have fled. She would have left the country. 

Andrew Hammond: Wow. This is so fascinating, the way that these things shake out. I was just thinking, as well, like, when you were, like, doing the research for this book, you know, someone like yourself that comes along that's trying to look at - you know, that's trying to get into the trees but also look at the forest - and it's something where most of the major players are still living, and they've all still got their reputations, their careers, etc., what's it like to write a book like that? Because you must - it must get quite testy sometimes, where people - you know, because you're potentially saying that this person was, you know, maybe not doing their job as well as they could have, or this agency didn't perform as well as it could have. And - but you're - these are some of the same people that you may have to go to to - you know, this is your chance to... 

Jim Popkin: Such a great... 

Andrew Hammond: ... Sort of form the writing of the book. So how does that go? 

Jim Popkin: That's such a great point. 

Andrew Hammond: Do you have to get used to just not being liked sometimes? Or... 


Jim Popkin: I've had that a lot in my life, Andrew. No, it's such a great point. And, you know, just in setting this up, I should have said, I'm an investigative journalist. I was at NBC News on 9/11 and I was covering the FBI. And I've covered the FBI for a long time. And as an investigative journalist, your job is to cultivate sources and get information from folks. But you're right. I'm an outsider to this story. And I also don't have a dog in this hunt, so to speak, unlike some other folks who were personally involved. 

Jim Popkin: I am both relying on my sources to tell me what happened, but at the same time, I'm vetting what they're saying versus all the other information. And, yeah, you're right. I'm - some places, I am critical. And it's a conversation, and sometimes even a negotiation, with folks to accurately report what happened. And, look, sometimes you don't - you're not going to know every last detail. And so in those cases, what I'll do is say, this person says this, and this person counters and says this, and let readers decide. It takes some judgment to try and do this and try to do it as fairly as possible, which is obviously the goal, right? 

Andrew Hammond: Well, congratulations on the book. It's a great accomplishment. I was wondering, as well, why - you know, so in the book, you make a good case that Ames and Hanssen, of course, they're very consequential. They pass on the names and information. But, you know, you make a good case. Ana Montes is briefing presidents. She's the first author on things that are helping to set up U.S. foreign policy towards one of its most critical adversaries, especially in the region. Why was she released in January while Ames and Hanssen are still in supermax prisons and getting one hour outside their cells per day, and they're never getting out? Like, how does - how is she getting out if she'd done just as much, if not more damage? 

Jim Popkin: Yeah. One thing to bear in mind is that with Ames and Hanssen, on, you know, the other side of the ledger, there are Russians who were executed as a result of their information. And that's super important. There's no allegation of that sort with Ana Montes. So I think that's a very important distinction. 

Andrew Hammond: And just briefly on that, do we not know what happened to any of - 'cause it's hundreds of people that she identifies. Do we not know what happens to any of them, or they're in prison or - but none of them were executed? Or... 

Jim Popkin: Yeah. To be more specific, she identified four covert agents - again, presumably CIA - in Cuba. We - we're not aware of them being arrested or executed. But that's basically, you know, another sign of how good the Cubans are in some ways because what they presumably did in those cases is just keep watching and then also probably try to feed false information to those people working for America to try to gum up the works back in Langley. Fortunately, none of those assets were executed, which was the case with Hanssen and with Ames. 

Jim Popkin: But to your question, why did she get a 25-year prison sentence? Arrested right after 9/11, the government never saw her meeting with any Cubans. So they didn't catch her red-handed, but they did have this information from her laptop when the FBI went in and conducted this black bag operation and grabbed her - the contents of her laptop. So they had that to use against her. But it was a somewhat circumstantial case in that way. 

Jim Popkin: They also did find in her possessions the crypto codes that she had and also the pager codes that she was using. We didn't talk about that. But she would go to pay phones - even though she had a cellphone in her purse, she would go to pay phones throughout Northwest Washington and enter - call pager numbers which were associated with the Cubans and enter short codes. And that was also a way to communicate. And she would do this in periods when she was not meeting with her handlers. She typically would meet with her Cuban handlers in restaurants in Washington, and she would slip them a disk - a computer disk - with all the information that she had gathered over the previous weeks or months. 

Jim Popkin: When she wasn't able to do that - and there was a long period where the Cubans just went dark on her and wouldn't meet with her - the only way for her really to communicate was by these cryptic pager codes. And so we see them, and some of them say, I'm in danger. I couldn't hear - you know, we were - a communication problem. There are all these little short codes that she had. And the photos are in the book, and some of them are online now. They're really interesting, and it's a shorthand way for her to communicate. 

Andrew Hammond: And it was different restaurants, or did she have a favorite restaurant? Anybody that listens in the D.C. area, is there one that they may know? 

Jim Popkin: She was a fan of Chinese restaurants, so a lot of inexpensive Chinese restaurants near the Metro in safe areas in Washington. She always insisted, you know, that it be safe. There was a lot of street crime back then in D.C. 

Andrew Hammond: OK. 

Jim Popkin: I wanted to get back to what you asked, that, well, why 25 years and why she was released. So it was largely a circumstantial case. It's a woman that they were prosecuting. I don't know if that entered into the equation with the prosecution, but they may have been worried about that with a D.C. jury. Maybe a jury would feel sympathetic towards her. And typically, DOJ and the prosecutors do not want to expose these cases. They don't want to go to trial. She had an excellent lawyer in Plato Cacheris, who also represented Robert Hanssen and Ames and Monica Lewinsky and many others. And he was a great lawyer. And they cut a good deal for her. So she got 25 years. She had to cooperate. She had to be debriefed and reveal what she knew about her - about the conspiracy and her spying. And she went and did - she did 21 years and three months. She got out early for good behavior. 

Jim Popkin: You're right. Hanssen and Ames and even the spy that I mentioned who was a professor at SAIS, Kendall Myers - he also spied for Cuba, doing a life sentence at supermax. So Ana was fortunate in that sense. She got 25 years. There are many folks who believe that she should have gotten a life sentence or worse. It's eligible for the death penalty. But they just never had enough evidence to prove that against her. 

Andrew Hammond: And I don't think we brought that out, but they were hoping to sit and watch her for longer so that they could see who her handler was. But then 9/11 happened, and you mentioned that she was going to be involved in targeting in Afghanistan and so forth. So basically, they decided to close the net and just roll her up, and that was the case that they had at that particular time. 

Jim Popkin: Right. The - I interviewed the DIA director at the time, Admiral Thomas Wilson - pretty remarkable. He knew that Montes was a - his employee at DIA and was being investigated by the FBI. The FBI - I talked about Elena and Scott Carmichael. They brought all this information to the FBI in late 2000. The FBI at first really fought them on it. They were upset that anyone outside of the family knew about this. Scott Carmichael had to be very persuasive and persistent in convincing the FBI that he actually had identified Ana Montes. Ultimately, he was successful. The FBI opens an investigation - a full field investigation in November of 2000. ******** 

Jim Popkin: **** So Admiral Wilson, who's running DIA, now knows, well, the FBI believes that there's a Cuban spy working in my agency. To his credit, he lets her stay there, you know, in the hopes of the greater good that the FBI will develop more information. But it was risky for Admiral Wilson to do that and keep her in place because she had - continues to get access to classified information during that period. So the FBI - they break into her apartment. They start to surveil her, follow her... 

Andrew Hammond: It's a black bag operation. 

Jim Popkin: It is a black bag operation - couple of times breaking into her apartment in Cleveland Park. And then 9/11 happens. And after 9/11, Admiral Wilson - he's running the DIA. He's got a couple major things going on. Number one, one of the hijackers' planes slams into the Pentagon. It kills DIA employees in the comptroller's office. So he's dealing with grieving families. And I mean, the whole office got - obviously got wiped out. So he's dealing with that. Secondly, he runs the DIA. He is responsible within the Pentagon for helping to plan our invasion of Afghanistan. So this is the world's busiest guy. 

Jim Popkin: At one point, a piece of paper crosses his desk that says that Ana Montes - who he and, you know, just only a couple of top officials know is under investigation - but that she is now going to get access to our bombing targets in Afghanistan. And when he learns that - and by the way, that was done by well-meaning folks who thought, well, Ana's really smart. She's a good analyst. They obviously did not know she was under investigation as a Cuban asset. 

Jim Popkin: When he learns that this Cuban spy is going to gain access to our bombing targets in Afghanistan. He says, guys, that's it. He contacts the FBI and says, you have to arrest her by Sep. 21, or I'm going to fire her. So on Friday, Sep. 21 - again, 10 days after 9/11 - that is when everyone realizes the gig is up, and she's got to be arrested. The FBI and DIA, Scott Carmichael put together a plan to arrest her. There's a kind of final deception where they call her into the inspector general's office at DIA on a ruse. They say that there's a problem with an employee. They get her to leave her office, come down to a conference room at the inspector general's office. And there waiting are the two FBI case agents who ultimately arrest her. 

Andrew Hammond: And who are the two case agents? 

Jim Popkin: The case agents are Steve McCoy, who I mentioned before, and then a younger agent named Pete Lapp. 

Andrew Hammond: OK. And unfortunately, this could easily be another whole hour, Jim. And I would love to talk to you for another hour. But there's so much that we never touched on. But I think that people can find the answers to some of these intriguing parts of it in the book. And it is available - Spy Museum bookstore. And there's going to be signed copies there very soon. So some of the things that we've never touched on that are really, really fascinating - in the book, you can learn why she never done this for money. She only reclaimed some expenses. 

Andrew Hammond: She - although she was released this month, she isn't repentant. She's not contrite. She still stands by what she done. She suffered from panic attack. She arguably delayed or never had a family because of her life in espionage. She's the product of a violent and domineering father. And we can - in the book, you mentioned some of the psychology that surrounds her and who she goes on to become. And there's just so much that you have to say that is very fascinating. And again, we could speak for another hour. But unfortunately, we're going to have to draw a line under it. But it's been really great to speak to you. And thank you so much. 

Jim Popkin: Absolutely. It's such an honor to be here at the Spy Museum and to talk to you as well. You guys are the true experts on this. And I just jumped in on this one story. But it really, really, truly is an honor to talk to you. Thank you very much. 

Andrew Hammond: Thank you. And what a great story it is. 

Andrew Hammond: Thanks for listening to this episode of "SpyCast." Go to our webpage, where you can find links to further resources, detailed show notes and full transcripts. We have over 500 episodes in our back catalog for you to explore. Please follow the show on Twitter - @intlspycast - and share your favorite quotes and insights, or start a conversation. If you have any additional feedback, please email us at spycast@spymuseum.org. I'm your host, Dr. Andrew Hammond. And you can connect with me on LinkedIn or follow me on Twitter - @spyhistorian. This show is brought to you from the home of the world's preeminent collection of intelligence and espionage-related artifacts, the International Spy Museum. The "SpyCast" team includes Mike Mincey and Memphis Vaughan III. See you for next week's show.