Criminal - Ana

Episode Date: August 9, 2024

Phoebe: Are there a lot of spies in this country today? Scott: Far more than people can probably even imagine. You can't rule anybody out. You never know what it is that motivates people to do this. For 17 years, Ana Montes was quietly sharing information with the Cuban government while working as a U.S. defense intelligence analyst. Scott Carmichael’s book is True Believer: Inside the Investigation and Capture of Ana Montes, Cuba's Master Spy. Jim Popkin’s book is Code Name Blue Wren – The True Story of America’s Most Dangerous Female Spy and the Sister She Betrayed. Say hello on Twitter, Facebook and Instagram. Sign up for our occasional newsletter, The Accomplice. Follow the show and review us on Apple Podcasts: iTunes.com/CriminalShow. Sign up for Criminal Plus to get behind-the-scenes bonus episodes of Criminal, ad-free listening of all of our shows, members-only merch, and more. Learn more and sign up here. Listen back through our archives at youtube.com/criminalpodcast. We also make This is Love and Phoebe Reads a Mystery. Artwork by Julienne Alexander. Check out our online shop. Episode transcripts are posted on our website. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Check out Ghost Story, a series essential pick, completely ad-free on Apple Podcasts. I just don't get it. Just wish someone could do the research on it. Can we figure this out? Hey, y'all. I'm John Flynn Hill, and I'm hosting a new podcast at Vox called Explain It To Me. Here's how it works. You call our hotline with questions you can't quite answer on your own. We'll investigate and call you back to tell you what we found. We'll bring you the answers you need every Wednesday starting September 18th.

So follow Explain It To Me, presented by Klaviyo. Very soon, I get to do my favorite thing. Go on tour and meet so many of you. This month, Criminal is coming to Austin, Tucson, Boulder, Portland, Oregon, Detroit, Madison, Northampton, and Atlanta. If you didn't get to come and see our 10-year anniversary show earlier this year, this is your last chance. You'll get to hear seven brand-new stories, most of which will probably make you laugh. I'll even try to come and say hi at the merch table. Get your tickets while they last at thisiscriminal.com slash live. Are there a lot of spies in this country today?

Far more than people can probably even imagine. Really? Oh, yeah. You can only imagine how many Americans are spying for the Russians, the Iranians, the Venezuelans, and the Cubans, and every country that has an interest in the United States, actually. So there are a lot of spies among us. Scott Carmichael spent almost 26 years as the senior security and counterintelligence investigator for the DIA,

the Defense Intelligence Agency. Do you ever feel offended that people know the CIA so well but not the DIA? Yeah, well, we kind of like it that way, actually. Truly, CIA gets blamed for everything. The DIA provides military intelligence about foreign countries. Sometimes people refer to it as the CIA for the Department of Defense. In 1988, the Defense Intelligence Agency decided to create its own internal counterintelligence element to look for spies within the agency. And so that's what I did.

Today, there are more than 16,000 people working at the DIA. We operate all over the world. Your wife is also a DIA agent. She was, yes. They're both retired now and have left Washington, D.C. for Wisconsin. Do you think that you are pretty good at picking out someone? I mean, you know, if you and I were walking down the street, you would be better at picking out someone who is maybe a spy than I was. Not necessarily. You know, you can't rule anybody out. That doesn't mean that everywhere you look, you think you're going to see a spy. But you never know what it is that motivates people

to do this. And so if you can't get inside another person's head, then you're not going to be able to spot a spy. It's a little bit more difficult than that. In the 1980s and early 90s, U.S. officials suspected that someone who worked for the U.S. government was sharing information with Cuba. They didn't know who. In the spring of 1996, Scott Carmichael got a phone call from a counterintelligence analyst at the DIA, Reg Brown, who specialized in Latin America. One of the reasons that Reg came to me was because on the 24th of February 1996,

the Cubans had shot down two civilian aircraft operated by American citizens called Brothers to the Rescue. They operated out of Miami, Florida, and their mission really was to help Cubans who were fleeing the country, but they were doing something else as well. Very often, they would throw leaflets out of the plane, which would flutter down into the streets of Havana, encouraging people to defect and saying not nice things about Fidel Castro and the Cuban government, that sort of thing. And the Cuban government did not like that one bit. In fact, they had threatened on a number of occasions to shoot down those aircraft. But, of course, they never did because they knew that they were operated by American citizens, and they could get in trouble for that. But on the 24th of February in 1996, they actually shot down two of these aircraft.

They killed three American citizens and one permanent resident alien in the process. This was a big deal. I mean, they crossed the red line in a very big way. And Reg knew, as a counterintelligence analyst, he understood that there's no way the Cubans would have done that unless they had authority from the highest levels, at least Fidel Castro. And that Fidel wouldn't have given that order unless he knew that he could cover his tracks. The next day, a retired U.S. Navy admiral went on television and said that he'd recently been to Cuba and had been told by representatives of the Cuban military that the flights could be shot down. The retired Navy admiral said that he'd gone to U.S. government officials to warn them.

And therefore his conclusion was this whole shoot-down matter was the fault of the United States government. We had failed to stop the overflights, and therefore we were at fault. Well, Reg saw that, and he said, wow, I mean, the entire story has just been spun in favor of the Cubans. And that's exactly what he would have expected the Cubans to do, to create that sort of situation. So Reg began to look into it to figure out, well, what happened here? He discovered that one day before the planes were shot down, the U.S. government had met with the retired Navy Admiral and that the meeting had been arranged by someone who worked at the DIA, a senior Cuban intelligence analyst,

a 39-year-old woman named Ana Montes. And Reds thought I was awfully suspicious that the meeting occurred just the day before the shoot-down. I mean, the timing was too coincidental. It looked to him that perhaps Cuban intelligence had set up that meeting just so that they could spin the story after the shoot-down. Retch Brown told Scott Carmichael that after the planes had been shot down, Ana Montes had been called to the Pentagon to debrief,

and that during the meeting, she took a personal phone call and left. She left around 8 p.m., and that struck him not just as odd, but just, it's almost unheard of. When you're called into the Pentagon by the Joint Chiefs because you are the expert that they need, you're not allowed to leave. You stay there on duty until they dismiss

you. You don't just pack up and go whenever you think you feel like going home. But that's what she did. Scott Carmichael reviewed Ana Montes' file and saw that earlier in her career, she'd been vocal about her disagreement with the U.S. government's policy in Cuba. She'd been questioned about her views twice before. The way she responded was, well, you're right, I don't agree with that. And as an American citizen, I'm entitled to my opinion. And I'm not the only one who has that opinion, by the way. There are U.S. congressmen and senators who also disagree with our government's policy in Latin America. But, you know, I'm a loyal person.

I've never done anything wrong. I've never advocated the overthrow of the United States and so on and so forth. It was a perfect answer. Scott Carmichael requested an in-person interview with Ana Montes. They scheduled their meeting for November 7, 1996. My first impression was that she was extremely businesslike, and she tried to take control of the meeting almost right away, before we even had a chance to sit down. She told me that she had an appointment at 2 o'clock and she couldn't miss it.

And before I even had a chance to get out my notes and things, she hit me with it again. She said, well, you know, I just hope this isn't going to take too long because I really can't spend a lot of time at this. And what I did was I said, look, Anna, this is not a routine security interview. I'm not doing a background investigation. I'm a counterintelligence specialist. And I've been watching your activities for a while, and I've got reason to be concerned that you might have been involved in a Cuban intelligence influence operation. What was her reaction?

Didn't say a word. She just stared at me. Scott Carmichael asked her about the meeting between U.S. officials and the retired Navy Admiral that occurred one day before the planes were shot down. Ana Montes explained that the son of a different DIA employee had also been on that trip to Cuba with the Navy Admiral, and he told his father about it, who suggested the meeting. So it wasn't Ana's idea at all. So it's not like Cuban Intelligence had directed Ana Montes to have this meeting. It actually was a DEI employee who asked her to do it. As it turned out later on, it happened just the way she said. Then I asked her about her leaving the Pentagon early,

and she couldn't remember receiving a phone call in the Pentagon, which would have been unusual, especially a personal phone call. She denied that altogether. Then she said, well, I did leave early. And the reason why was because I hadn't eaten all day. And she had a medical condition, and she could only eat certain foods, so she couldn't eat anything out of a vending machine. And she said, by the end of the day, I was starving, and there was nothing going on. They didn't really need me anymore, so I left. Now, again, I told Anna, I'm going to have to corroborate this in some way. Where did you go? And she said, well, I went home.

Now, I knew enough about Anna at that time to know that her grocery store was just right down the street from her condo building. So I asked her, well, where did you park? She said, well, I always park across the street from my condo building. So I asked her, well, where did you park? She said, well, I always park across the street from my condo building. I said, okay, when you park your car, did you bump into anybody? Is there anybody I can talk to who can corroborate all this? She said, no, I don't remember that. But then I asked her, well, okay, did you go down to the store to get something to eat

or maybe to fix for dinner, and would anybody working in the store remember you? She said, no, I don't remember going to the store. I said, okay, what did you do next? Did you cross the street to go to your building? And at that point, she froze and again, she stared at me like a hawk. And she denied that she saw anybody. But I felt that she was trying to hide something. After that, again, I asked her about her disagreement with the U.S. government's policy on Latin America.

And she gave me the exact same answers she had in 1986, 1991, in the same order. So I knew that she was prepared for that question. She had actually rehearsed it. It was word for word. And again, that's kind of set off alarm bells as well. I'm Phoebe Judge. This is Criminal. Tell me a little bit about her. Where was she born and how did she get into intelligence? Ana's family, Ana's parents were both Puerto Rican.

Both of them favored the idea of independence for Puerto Rico from the United States, but both of them felt that however that's going to be accomplished, it's got to be done peacefully. They weren't radicals in any sense of the word. Her father was a United States Army officer. He was a psychiatrist. Anna Montes was born in a hospital in Nuremberg, Germany, in 1957. Her family moved back to the United States when she was a baby. She was the oldest of four children. They eventually settled in Towson, Maryland. She graduated from high school there in 1975. In her yearbook, she said her favorite things were summer, beaches, soccer, Stevie W., PR, chocolate chip cookies,

having a good time with fun people. She went to college at the University of Virginia, and when she was a junior, she studied abroad in Spain. And, you know, for many students who are in college, when they go abroad, especially to Europe, you know, it's about the culture and the fun and drinking and traveling. Author and reporter Jim Popkin. Well, in her case, she met a young Argentinian who was very politically active and astute. And she fell in love with him, and he kind of convinced her of the evils of U.S. politics around the world. And she stayed in touch with him and his friends for decades after that. And they had a profound influence on Ana that kind of set her on her course. When she graduated from college, she went to Puerto Rico, where she lived and worked for a

short time before applying for a job as a typist in Washington, D.C., at the Justice Department's Office of Privacy and Information Appeals. She got the job. It was 1979. Her colleagues described her as loyal, very moral, and extremely independent. She was promoted and given a top-secret security clearance, giving her access to classified DOJ files. She reviewed files that had received FOIA requests and evaluated what information should and should not be made public. She decided to apply to graduate school. She enrolled in a program at Johns Hopkins, the School of Advanced International Studies. that she was trying to prove in addition to just the sheer politics and her own political views about what the Reagan administration was doing at that time. Many young people were offended

with what Reagan was doing in Central America. The U.S. was inserting itself in Nicaragua and El Salvador, and many people were offended by what Reagan and his cronies were up to at that time. She got close with a classmate at Johns Hopkins, a woman named Marta Velazquez. Marta Velazquez was born in Puerto Rico. She had studied Latin American studies at Princeton and completed law school at Georgetown before enrolling in Ana's program at Johns Hopkins. She was also working for the Cuban government. Marta Velasquez had been asked to find like-minded students at Johns Hopkins. According to the Department of Defense,

Marta started her recruitment effort with a soft pitch. She told Ana she had friends who wanted some help translating news about Nicaragua into English. If Ana was interested, Marta could make an introduction. They took the train to New York to meet Marta's friend for dinner. That was the night Ana Montes was recruited. It was December of 1984. She was 27. We'll be right back. Subtle results.

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a seven-part series that follows journalist Tristan Redman as he tries to get to the bottom of a ghostly presence in his childhood home. His investigation takes him on a journey involving homicide detectives, ghost hunters, and even psychic mediums, and leads him to a dark secret about his own family. Check out Ghost Story, a series essential pick, completely ad-free on Apple Podcasts. Around the time Ana Montes agreed to work with the Cuban government, her sister, Lucy, accepted a job with the FBI. She would be based in Miami, working as a translator, in a field office dedicated to locating Cuban spies.

When Lucy told Ana about her new job, she told Jim Popkin that her sister snapped at her and said FBI agents were jerks. Lucy said she didn't understand her sister's reaction at all. In March of 1985, Ana and Marta took a trip to Madrid. They posed for pictures as if they were on a European holiday, taking, you know, snapshots in front of, you know, major capitals and museums and that kind of thing. And then they went and they met some Cuban agents. They got fake passports. They got wigs. And Ana also got her training, her initial

training, how to pass a polygraph test, a lie detector, how to avoid someone following you, how to communicate surreptitiously. So she got her SPY-101 training and then came back to the U.S. and the Cubans at that point helped her apply to the DIA to work inside the U.S. military establishment. In September of 1985, she began work as an analyst for the DIA. Jim Popkins says she had access to field reports from all the key U.S. intelligence agencies and would research and write reports on the Latin American countries she was assigned to cover. She had a good reputation, you say, at the agency. Oh, absolutely.

Anna's work ethic was matched by no one. I mean, I watched her, obviously, during the course of the investigation, and I can tell you that she's like a machine. Scott Carmichael. She would come into work at eight o'clock, right on the dot, and while most people would sort of ease into the workday, they would be chit and chatting and maybe talking about the football game. They might go get some coffee and have a donut or something. Anna never did that. She went straight to her desk. She would sit down. She usually left a pile of paperwork next to her computer to go through the next day.

She would sit down. She would start working right away. She would work straight through until noon. Typically, she would go down to the cafeteria, and she might get a salad, bring her tray back up to her cubicle, and continue working until 4 or 5 p.m., and then she would just pick up and go home. As a consequence, I had an opportunity to talk to her immediate supervisor, and he said, you know, Scott, she probably put out at least four times more on average

than anybody else in the intelligence community. She was what we called a blue flamer. Anna was a super producer, and she received lots of recognition for her work. She was recognized as probably the best analyst that we had at DIA at the time. What did you learn about her personal life? Anna was aloof. She was not a gregarious kind of person. I mean, she didn't have any real close friends that we could see.

She certainly was not close to anybody at work. And as far as her life off-duty, we had no idea. I mean, she lived on a condominium, and she had neighbors, and she interacted with the neighbors, but it's not like they would do things together, socialize. So Anna was a very private person, and we figured that that might be driven in part by just her personality, but also in part by the fact that she was trying to keep people at a distance because she was engaged in espionage. She wouldn't want anybody to pick up on that. Ana Montes had been a spy for 11 years

when Scott Carmichael sat down to interview her. Cuban intelligence trains their agents to maintain a very low profile. They tell them, you know, here's your list of do's and don'ts, and pay particular attention to the don'ts. They want to make sure that they don't bring any attention to themselves, especially attention by security. So she would naturally be a little bit paranoid about the possibility that somebody would suspect her. Now, when I interviewed her in 1996, she actually, we know now, that she told her Cuban handlers about my interview, but she felt that she got through it just fine.

She felt that, as a matter of fact, she celebrated. We knew that Ana, when she wanted to celebrate, she would drink a couple of Heineken beers. Ana never drank beer. She only drank beer if she was celebrating, and she had a couple of Heinekens after the interview. I'm just thinking about how hard it must be to catch someone who's trained in methods of deception. Yeah. Well, I'll tell you, the whole idea of tradecraft is to protect the agent. And that tradecraft is designed to make sure that people like me did not develop any concerns about her.

Anna was really creative in the sense that she didn't take documents out of the building like the Russian spy Robert Hansen did when he was an FBI agent. He stole a lot of documents and handed them to the Russians for cash. Anna was motivated by politics, and she learned early on that the safest way to operate was to memorize. So she memorized every day she came in. She basically had two jobs. Her day job was work at the DIA as a top analyst, and she had the right to read classified documents from many, many agencies, the CIA, DIA, many others. And so she would read all day, and she's looking at documents with the frame of thinking, what's going to be helpful

for Castro and the Cubans? What should I remember today? So she would try to memorize it. She used mnemonics. I found one of her books that she bought on how to improve her memory through the use of mnemonics. And then her second job would begin when she went home to her apartment in Cleveland Park. And she would try to regurgitate everything important that she had learned that day and type it into her Toshiba laptop. And she did that every day for practically 17 years. So it was just an enormous volume of information that she was able to turn over to the Cubans. How did she turn the information over? Ana met every couple weeks with her handler. It was not an officer with the Cubans. It would be

like a business person or someone with a legitimate cover. And she would typically meet them in Chinese restaurants near a metro in D.C. And she would have typed all of her information onto her laptop, coded it. She had software the Cubans had given her to code it and then put it onto floppies, onto, you know, disks and then covertly hand them over to her handler. So every couple weeks, it was basically a data dump to her handlers. And then her handlers also would give her instructions. And then she also would get her weekly instructions by listening to the shortwave radio in D.C. Tell me a little bit, it was just coming to her? Is it encrypted, the messages? Yeah, it's fascinating and it's still being used.

So shortwave radio was used, especially during World War II, to communicate with spies all over the world. In this case, you'd have a woman in a soundstage in Havana who would read a series of numbers, blocks of five, and they would go on for 150 sets. And it's just numbers in Spanish. 0, 4, 4, 7, 3. But if you have the code, those numbers obviously are all words, and they were instructions to Ana, offered twice a week to her, repeated often in case she wasn't always at home at the right time, and that told her where to look and what to do that particular week.

It seems like there were indications to Scott Carmichael and his colleagues at the DIA that she was operating outside of normal protocols. But the FBI didn't initially listen. Yeah, that's right. And, you know, I give Scott and the DIA credit because they got onto Anna early and but for their work. The FBI, I think, would not have solved this case. In fact, they thought it was probably a man at the CIA. What kinds of things were they noticing her doing that put her on their radar? Anna was an interesting or is an interesting person. She was very short with people who she didn't feel lived up to her intellectually.

And she often invited herself on her own to meetings. And some people thought that was odd. She kind of pushed her way into a lot of meetings. But back then, that started to make some people suspicious about her, why she was poking her nose into areas that maybe she didn't really deserve to be in. And that and a couple other clues started to make people think that maybe everything wasn't right with Ana Montes. Something that amazed me was learning that when you work in counterintelligence, you know, your personal life, what you do on the weekends, who you spend time with, even whether you go to therapy is fair game for your employer to look into. Yeah, especially the therapy point.

And I, you know, this is kind of incredible to me as a reporter, but I learned the name of Ana's therapist and talked to him and interviewed him. And he did an on-the-record interview, which is, you know, pretty remarkable. And yeah, I mean, by the way, he says that Ana never shared with him that she was a spy. She just talked about the stress that she was under at work. But that was something that she had to reveal to the DIA, to her employers, and she did. And, you know, it really, it's pretty common, right? So it didn't really raise any red flags in and of itself. But yeah, when you have a security clearance as high as Ana did, you give up a lot of your kind of personal freedoms and the privacy that a normal person would have. I mean, it makes you realize that if you're going to be a spy within one of these organizations,

your life is going to be pretty lonely and quiet. It's walking around with this giant secret that you can't share. It's very, very isolating and really tough for her. She locked herself in in her late 20s into this life of kind of deprivation and loneliness. Scott Carmichael said that there are more spies in this country than we can imagine. Yeah. I mean, look, I think that's absolutely right. And Scott would know for sure because he did this for a living.

But this city, Washington, is dripping with spies. I mean, is this how diplomacy really works? And we see these television shows and think, oh, you know, that's fiction. But maybe this is actually how everything gets done. I don't know if it's how everything gets done, but it certainly is how it works. And by the way, the CIA is, you know, is hard at work as well. We have our own spies all over the world, you know, a big network of folks. But this is how it works, you know, geopolitically, spies in major capitals all over the world. It's tolerated to some degree. The FBI is aware of who is working here under official cover, for example, for the Cubans, and they keep an eye on them. They keep a close eye on the Russians, obviously.

But there are many folks who are not under official cover who also are working for these governments, and they're all over the major capitals. Scott Carmichael had interviewed Ana Montes in 1996. And then, in the year 2000, his colleague at the DIA, Chris Simmons, got a tip from someone at the NSA. Whoever was sharing information with the Cuban government had very likely visited the Guantanamo Bay military base during a specific two-week period in July of 1996. Because Guantanamo was a military base, the Department of Defense would have comprehensive records of who came and went. We had access to information about travel to Gitmo that the FBI almost certainly did not have.

We had access to a database. If you travel early on a Gitmo, you've got to get permission, official permission, from the Office of the Secretary of Defense to do so. And those requests and messages are actually retained in the SAFE system. So I decided to query the SAFE system, and I was going to try to identify any DOD employees who may have traveled to Gitmo during that July 1996 period of time. And I came up with what we call about 100 hits. And I started clicking through those messages very quickly. I hit the 20th message, and I saw Ana B. Montes at Travel to Gitmo.

And the very moment I saw her name, I knew that she was the spy. I mean, I just knew it in my gut. We'll be right back. Hey, it's Scott Galloway, and on our podcast, Pivot, we are bringing you a special series about the basics of artificial intelligence. We're answering all your questions. What should you use it for? What tools are right for you?

And what privacy issues should you ultimately watch out for? And to help us out, we are joined by Kylie Robeson, the senior AI reporter for The Verge, to give you a primer on how to integrate AI into your life. So, tune into AI Basics, How and When to Use AI, a special series from Pivot sponsored by AWS, wherever you get your podcasts. What software do you use at work? The answer to that question is probably more complicated than you want it to be. The average US company deploys more than 100 apps, and ideas about the work we do can be radically changed by the tools we use to do it. So what is enterprise software anyway? What is productivity software?

How will AI affect both? And how are these tools changing the way we use our computers to make stuff, communicate, and plan for the future? In this three-part special series, Decoder is surveying the IT landscape presented by AWS. Check it out wherever you get your podcasts. After Scott Carmichael realized that Ana Montes had visited Guantanamo Bay during a specific two-week period back in 1996, he asked for a meeting with the FBI.

He brought a lot of paperwork with him and remembers being in a room of about 8 to 10 people, explaining why he thought Onamontes could be a spy. He said he'd been speaking for about two minutes when one of the agents interrupted him. And said, well, I think I've heard enough. I don't think that your employee is the spy I'm looking for. I've got reason to believe that the person I'm looking for is a male, not a female, and more likely a CIA than DIA.

In fact, he said, I never considered the possibility that this person was at the Department of Defense. And that was it. I was essentially dismissed. Scott Carmichael didn't give up. For weeks, he kept looking into Ana Montes and faxing what he found to the FBI agent in charge. And finally, in my frustration, I called him up and I said, look, I need to talk to your supervisor, which is something you never do. You never go over an agent's head to their boss. And if you do that, a word very quickly spreads. You know, our community, counterintelligence community, is relatively small.

There are only so many investigators who do this kind of work. And the word would have gotten out quickly that, hey, Carmichael went to the boss. And then at that point, nobody would want to work with me at all. So I was putting a lot on the line professionally there, but I was convinced that Donna was the one. so I did that. And I met with his squad leader, and at the end of that meeting, her bottom line was, well, you know, thanks, but no thanks. So again, I was dismissed. Still, he kept going, sending every little bit of information he could find

along to the FBI. And eventually, the FBI began an investigation in October of 2000. So they had established her routine, and they were used to seeing her on Sundays. She would go to this Hex store up on Wisconsin Avenue first, and then she would go across the street maybe to a sporting goods store. This was kind of normal activity, and she would always park her car in a parking garage next to goods store. This was kind of normal activity. And she would always park her car in a

parking garage next to the store. So the FBI surveillance had parked their car on the very top floor of that parking garage. And this was probably the, I don't know, probably the 20th or 30th time that she had done this, that they'd seen her doing this and didn't really think that much of it because nothing unusual had occurred before. One of the FBI surveillance just happened to be looking over the edges of the top floor, looking down at the store when he saw Anna exit the store. And she sat down on a sort of a half wall and was looking at her watch. And then at exactly one o'clock, she got up and she went to a payphone nearby and she made a phone call. Now, that was unusual.

That's not something they ordinarily saw her do. Well, then what she did is she left and she drove down the street and parked her car, walked up a couple of blocks. Now, Anna always carried a cell phone with her. She walked past a payphone during that little walk, crossed the street to a supporting goods store, and went in there. And they saw that she came out with a bag, obviously had purchased something, but at exactly two o'clock, she went to another payphone and made another phone call. What the FBI does in cases like that is they wait until the suspect leaves, and then they would go to the same phone booth, drop a quarter in,

and they would make their own phone call. And then later on, they would go to the telephone company and say, Well, look, I made a phone call at this time from this phone. I want you to tell me about the previous phone call from this phone. Now, the FBI found out what number she had called, and they knew from investigations of the New York area that she had called a pager, which was, we knew, was operated by Cuban intelligence operating out of the UN mission in New York City. So that was the first pretty good indication that she was still active as a spy.

In May of 2001, the FBI searched her apartment. And I've got to tell you that I've never met people who are so meticulous. I mean, what they have to do is they have to tear that place apart and then absolutely put it back together to an eighth of an inch. I mean, the books, everything, everything had to be put back. They did that in her apartment. They did find a few things. They found, for example, a shortwave radio.

Also, they found the Toshiba laptop underneath her bed. And of course, they copied the hard drive on that thing. When they did, what they recovered from that laptop was a lot of communications between Anna and her case officers going back and forth, messages that she was receiving directly from Havana, as well as messages that she was transmitting to Havana by another means. She was arrested in her office at DIA headquarters on Bowling Air Force Base the week after September 11, 2001. What was her reaction to her arrest? Anna was cool, calm, and collected.

She had almost no reaction. She immediately asked for a lawyer, and she walked out of that building in cuffs with her head held high. And it really surprised the FBI how she never showed her emotions and really never even broke down that day. Her mother later told the Miami Herald, quote, I'm still flabbergasted. She said, we waited and waited to find out it wasn't true. Her sister Lucy, who was working with the FBI, said, I believed it right away. It explained a lot of things. Ana Montes had a boyfriend, an intelligence officer who also specialized in Cuba. He had no idea. He told Jim Popkin, quote, one thing that gives me comfort is that I had already started

to date someone else. Ana Montes pled guilty to one count of conspiracy to commit espionage. This was the result of a plea agreement in which she would offer up everything she knew in exchange for a 25-year sentence. The judge told her, if you can't love your country, you should at least do it no harm. She gave a statement in court saying, quote, I obeyed my conscience rather than the law. I was interested to read the statement that she gave in court. She said, all the world is one country. What do you understand about her motive? She felt like the United States was a bully, particularly in Central and South America.

There's pretty good evidence for that. But that was her motivation. She felt like the U.S. was taking advantage of smaller countries and asserting its will on weaker countries. And that offended her. But what she would say is, how could I not have done this? Given everything that I know about America and its bullish actions around the world, I had to stand up and do something. In 2005, the Office of the Inspector General of the Department of Defense published, lack of judgment, infidelity, fascination with the art of espionage, or other frailties. The review stated that Ana Montes believed, quote, that the United States did not respect the countries of Latin America and caused the death of people who didn't deserve to be killed. Do we know what happened as a result of her sharing intelligence information with the Cubans?

Well, we know a lot of what she shared, and a lot of it was very, very classified. I'll give you a couple of examples. One is she shared the true names of CIA agents working in Havana. That's a very dangerous game to play. She's telling the Cubans who's spying on behalf of the United States in Havana. Now, they could have been imprisoned. They could have been killed. As far as we know, they weren't, but that's the level of detail that she had, her level of security clearance. She also shared a lot of information about how we communicate,

how we spied, including some very sensitive information about a spy satellite, a very secret spy satellite that the Defense Department was using at the time to spy not just on Cuba, but on all of our enemies. And so it was extremely dangerous what she was playing. The head of counterintelligence at the time, after doing the damage assessment, called Ana arguably one of the most dangerous spies in U.S. history. She had the two jobs, she worked them for 17 years, and she was very good at both of those jobs. I mean, she did this for no money. She didn't do it for the money.

And she didn't really do it for the glory either. She did it because she's a true believer. She believed in communism, and she wanted to help the little guy. That was really her main motivation. She just felt like the Cubans were being bullied, and she thought, I'm in a unique position to help. I'm going to help them.

After Ana Montes was arrested and news outlets reported that she was cooperating with the U.S. government, her old friend and recruiter, Marta Velasquez, left the country. She moved to Sweden, a country with no extradition agreement for spying. She was indicted in 2004, but has not been tried. Ana was released from prison early last year in January of 23, and she's on parole. And she immediately went to Puerto Rico, where she has a cousin. She is trying to, you know, kind of work her way into Puerto Rican society and also to see her family. Her mother is quite ill and lives in the States. And so she's

been trying to see her. And, you know, after such a long time in prison, that was a big goal of hers. And remarkably, she has a small group of very vocal, active supporters who kind of consider her to be a martyr. So she's kind of found her people in Puerto Rico. Today she's 67. We attempted to contact her through her lawyer, who replied that she does not give interviews. Jim Popkin reports that while she was in prison, she wrote a letter to a friend in 2013.

I believe that the morality of espionage is relative, she wrote. The activity always betrays someone, and some observers will think that it is justified, and others not. Thank you. Bishop is our supervising producer. Our producers are Susanna Robertson, Jackie Sajico, Lily Clark, Lena Sillison, Lucy Sullivan, and Megan Kinane. Our show is mixed and engineered by Veronica Simonetti. Julian Alexander makes original illustrations for each episode of Criminal. You can see them at thisiscriminal.com. Both Scott Carmichael and Jim Popkin have written books about Ana Montes. Scott Carmichael's book is called True Believer, Inside the Investigation and Capture of Ana Montes, Cuba's Master Spy.

And Jim Popkin's book is called Code Name Blue Wren, The True Story of America's Most Dangerous Female Spy and the Sister She Betrayed. We'll have links in the show notes. You can sign up for a newsletter at thisiscriminal.com slash newsletter. We hope you'll join our membership program, Criminal Plus. Once you sign up, you can listen to criminal episodes without any ads, and you'll get bonus episodes with me and criminal co-creator Lauren Spohr, too. To learn more, go to thisiscriminal.com slash plus. We're on Facebook and Twitter at Criminal Show and Instagram at criminal underscore podcast. We're also on YouTube at youtube.com slash criminal podcast. Criminal is part of the Vox Media Podcast Network. Discover more great

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