The Spy Who - The Spy Who Colluded with Castro | How Ana Montes Fooled Her FBI Siblings | 4

Episode Date: October 21, 2025

How did Ana Montes spy for Cuba for 17 years while surrounded by FBI agents, which included her own relatives? Investigative journalist Jim Popkin joins spy novelist Charlie Higson to reveal how the Pentagon's top Cuba analyst maintained her double life, and shared Thanksgiving dinner surrounded FBI family members while feeding America's military secrets to Havana. Having spent extensive time with Montes’ own siblings, Popkin knows this remarkable story of deception inside out - from Montes’ risky romance with an intelligence officer, to the psychological discipline that kept her hidden in plain sight. It's a tale that shook US intelligence to its core, wrapped around a family drama that still reverberates today.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wonderry plus subscribers can binge full seasons of the Spy Who early and add free on Apple Podcasts or the Wondery app. From Wondery, I'm Charlie Hickson, spy novelist, actor, comedian and this is The Spy Who. Thank you for joining us for our final episode of The Spy Who colluded with Castro. The real art of espionage is to stay hidden, and Anna Montes remained hidden in plain sight for 17 years. Working at the Defence Intelligence Agency, the nerve centre of US military strategy, Anna shared its secrets with its closest enemy, Castro's Cuba.

Eventually, her actions earned her the title The Most Dangerous Females Spy in US History. From a young age, the army was a defining part of Arna, life. Her controlling father was a US army colonel. Her brother and sister both became FBI agents, with her sister Lucy specifically tasked with finding Cuban spies in the US. Little did she know there was one on the opposite side of the dinner table. To hear how her story unfolded, make sure you've listened to episodes one to three of this season. In this episode, I'm going to talk with author and investigative journalist Jim Popkin.

He wrote the book, Codename Blue Wren, the true story of America's most dangerous female spy, and the sister she betrayed. Jim knows the world of Anna Montes. He knows the family, he knows the agents who worked with Anna, the ones who trusted her,

the ones who eventually took her to her sentencing. I want to understand how Anna was able to work undercover for so long, how she could sit across the dinner table from her family and loved ones and not crack, and whether he thinks the Cubans really cared for at all. Well, welcome, Jim. Thanks for joining me on The Spy Who. Where are you actually joining me from? Where are you there? Hello, I'm in New York City today. Do you live there, or is that you're just there? No, I don't live here, but I'm in the city a lot. Working hard. Yeah, something like that, yeah. Well, let's get straight on to Anna, and we start with, it's the most obvious question, is what drew you to writing

about this story. How did you become involved in it? I was at NBC News back in the day. I was an investigative reporter for NBC in Washington, D.C. And I was covering the FBI and CIA at the time. And I first heard about Anamontes when she was arrested, which, you know, was 10 days after 9-11. After I wrote the book, I looked back and realized we never even did a story, a proper story on the evening news about, about Anna and the arrest because of the events of 9-11. But a friend of mine, after the arrest, called me up and said, she bought my condominium in Washington. And that meant that I had spent, it was my college roommate.

Just the thought that I was there so many times, hanging out the living room in a place where Anna used to get encrypted messages from her Cuban handlers, It just connected me, rooted me in this story. It's a story about two sisters trying to patch together a relationship while one of them is living a massive lie. It's a family story wrapped around an espionage tale. That's what pulled me into this story in some ways a lot more even than the spying element. And that's really like why I loved the Sopranos.

The Sopranos was on the surface about the mafia, but really it was about a family and how a man was running his family with this extremely complicated secret life. Were you able to start getting a picture of her as a person? And what sort of a person emerged? I had no access to Anna, no reporter did. Under the conditions of her plea deal,

she was not allowed to talk to the media. I reached out to Lucy. Lucy was at the time an actor employee of the FBI. But at that moment, they had communicated back and forth with Anna writing letters from prison, phone calls, and the occasional visit. And Anna continued to be unrepentant. And these two sisters were, I would say in terms of Lucy's point of view, kind of at each other's throats at this moment, and gave me, you know, an interview was pretty angry about her sister. She really wanted to get the word out that Anna had betrayed the family and betrayed the nation.

And then I broadened from there and talked to Anna's friends, her professors, her colleagues. Some of it was complimentary. She's very intelligent. She was really organized. She was very close with her niece and nephew. She was a really good attentive aunt. And she had some friends who were, and to this day, remain extremely loyal to her.

I thought that was important as part of the picture. I knew I was going to get a lot of the negative part, but it was important to hear the positive attributes, too. And I think that's what made her a successful spy. But early on, especially when, you know, as a younger woman in college and in graduate school, she was as described often a lot of fun, a fairly typical person,

and that really changed later in her career. You mentioned there about her being so successful, and Arna did cause an enormous amount of damage to the U.S. military. A billion-dollar spy program, potentially rendered useless war plans could have been influenced and revealed to America's enemies. You've described her as the most dangerous female spy in U.S. history. Do you think she was probably one of the best spies, too, or I guess the best spies are the ones we'll never know about? Yeah, that's a good point. Yeah, I mean, I consider one of the most successful spies, period, and certainly one of the most consequential female spies. But one of the reasons why I make that argument is, first of all, 17 years.

She's at it so long. She rose up to a fairly high level within the Pentagon, and she was smart as hell. So she did really well in her job. You have other spies like Rick Ames over at CIA who had a drinking problem and a lot of other issues. Anna kept her personal problems kind of in check most of the time when she was at DIA. And so she kept getting awards and cash rewards from the government for her excellent service. And she was really relied on by politicians, by other U.S. officials, even some journalists before they went to Cuba, would get briefed by Anna Montez, which is, you know, really remarkable. Correct me if I'm wrong, but she didn't seem to have any huge.

ideological drive. I mean, in terms of being a communist or anything like that. And she had no ties to Cuba. So what was her motivation through that? I would say she was a communist adjacent. Right. I can't say that she is or was, you know, a communist, but she certainly believed in a lot of those ideals. Well, there are two main reasons why I think she spied. Number one is she was offended by the very muscular U.S. foreign policy. But also she was a student of history and looking back at U.S. intervention around the world. And she just saw the United States as playing a bully role, you know, intervening in the lives and the political operations of many other countries. And she just thought that was grossly unfair. Cuba's a small country. They don't have a lot of

resources, the United States has played an oversized role in controlling the lives and the economy of Cuba. And she was very offended by that. So you have that. And then on the personal side, there absolutely was something going on. I think she spied because it gave her power. She also had this very complicated relationship with her father who had been in the military and was physically and psychologically abusive to her, you know, as a young person that was able to get my hands on a CIA behavioral analysis of Anna post-arrest. And there were a number of psychologists who interviewed her. And their take, and you could say, you know, maybe this is dime store psychology, but their take was one reason is that she wanted to get back at her father. And what

better way to do that if your father had been in the military, then basically attack the U.S. military. Audible.ca. slash Wondery. You mentioned her father earlier. Did her father live to see her arrested? No, he didn't. He died about a decade before Anna was arrested. So, I wonder what he would have made of that moment.

I mean, he would have been absolutely horrified. He grew up in Puerto Rico, worked for the army, was a very proud American. And in doing the research for the book, I realized he's from a kind of a long line of fathers who were physically abusive to their children. And so he grew up with a belt himself and had a very tough upbringing. And by the way, I don't want to oversell this. I'm not saying he didn't love his children. This is how he raised them. It just created a huge amount of conflict and tension, especially between Anna and her father, Alberto. She was the oldest. She was an overachiever. She went to the University of Virginia, which is a great school.

She had terrific grades. She was kind of the apple, the eye of Alberto, and he was probably harder on her than on any of his children. I think he would have been absolutely just shocked and horrified at her behavior. And what about Anna's mother? What was her relationship with her like? Anna was much closer with her mother. The parents had a pretty nasty divorce and breakup. And Anna certainly kind of favored the mother during that. Mother was, I think, more nurturing to her. An activist in her own way, more about community and not so much political, but more about community, local life and ultimately in Florida. And she got very involved with Puerto Rican and Latino events in the area. And they were just a lot more simpatico as readers and kind of intellectuals in the way. Although the father was

very smart too, but they just were a lot closer. You mentioned there Anna's mother being involved with the local Puerto Rican community. I mean, is Anna's background as a Puerto Rican, Do you think that's important? Could she have had an outsider's view of America? Yeah, I think it is and was important. She's living in Puerto Rico now. It's kind of where she fled to upon her release from prison. She had family there, and she often would go with her siblings in the summer.

She moved there briefly after college, and then right before her, she got her first real job at the Department of Justice in Washington. So she had a, you know, a strong first. familial bond with Puerto Rico. Puerto Rico resisted a lot of colonial attempts. And there's also a connection between Puerto Rico and Cuba politically. And I think Anna probably was influenced by that as well. Now, all the spies we look at on the spy who have to hide their true selves from people who are close to them. But I mean, in Anna's case, it was so much more extreme because her immediate family were working in the very fields that she was attempting to undermine. The U.S. military, the FBI, the Pentagon, and the discipline that was required to do that, do you think, ironically,

that a lot of that would have come from her father? That's a very good point. I think you're probably right. You know, at the end of the day, she's the daughter of an American military man. There comes with it, you know, certain rigor and discipline. I mean, I think the other engine for her, was that she wanted to be successful. And she was, right, in two jobs. Job number one is the job on her resume. I'm an analyst at DIA. I work for the Pentagon. And then job two is, secretly, I'm a spy for Cuba, and I want to be successful there. I think she just really wanted to be perceived as intelligent, capable, disciplined in her own way. I think she probably did get some of those lessons from her father. use them not for good in this context. I mean, it's incredible that she was able to balance those

two lives. And, I mean, there's a Thanksgiving dinner that you write about in your book that I think really very clearly illustrates the sort of tensions she was having to deal with at home. Yeah, I just always have really loved this anecdote. So just a little bit of context. Anna decides to spy for Cuba while she's in graduate school. And completely coincidentally, at the same time, her sister Lucy, starts working for the FBI. Lucy then, she meets a guy in Miami who she marries, who also is at the FBI. Okay, so now that's two members of the family at the FBI. And then at one point, there's a big recruiting drive at the Bureau where they want folks who are, you know,

know, from varied backgrounds. Lucy thinks, you know who would be great is my sister-in-law. She'd be terrific at this. So she calls her sister-in-law, Joan, and has a conversation with her. She's very interested in joining. And then out of the blue, Joan says, you know what? I'm going to ask my husband, who is Anna and Lucy's Tito, if he wants to join, and he says he would love to also. They become FBI special agents, you know, the real deal. We think about it, the FBI. So in a matter of years, Anna has four family members who all work at the FBI. Now, back to the question about Thanksgiving.

You can just imagine, Anna shows up at Tito's house, and they're in Atlanta now, and they're FBI agents. No, that means handgun badge, right? and they invite a bunch of their friends who also all are FBI agents. So the place is just creeping with feds in walks on Amontes. It must have been extremely uncomfortable for her. And it's kind of just serendipity that any of this happened. And it's just because Lucy read a classified ad in the Baltimore Sun that she ended up at the FBI and everyone else did.

And I gather when it all came out that, Lucy was almost guilty of thinking, oh, my God, you know, that must have been so terrible for Anna when I joined the FBI. And at the same time, thinking, I can't believe my sister was a spy. In retrospect, she realized that when she made that call to her sister, say, hey, great news, I'm going to work for the FBI. She understood why she got this, you know, flat response. And they had been very close when they were little. And in fact, Anna was almost like a mother. figure to her. She would help bathe Lucy when she was a little girl and then helped her get to school. Even on day one of school, wasn't mom who took her. It was Anna who took Lucy, rather. And Lucy

really looked up to her older sister. Their relationship absolutely soured over the years. And Anna refused to talk to her about anything really of any consequence and especially about work. And let's give Anna some credit in this area. It's possible that she made a decision early on not to tell her family anything about what she did. And that is pretty much true, according to Lucy, that Anna pretty much never shared any office gossip or anything about what she was up to

because she was trying to protect her sister. And again, this is a theory. If Anna thought, well, if I tell her, I'm going to the Pentagon today for a classified meeting, Well, then she's involving her sister in her crime. Maybe she thought in the back of her head, if I'm ever arrested, I want Lucy to be able to say, I never knew anything about her job at all. Ana never shared a damn thing, and it drove me crazy.

That's what Lucy ultimately told the FBI, and it helped protect her. And by the way, after Anamontes is arrested, Lucy is allowed to stay and continue to work at the FBI for years. They must have been very confident that she wasn't involved in any way and that Anna worked in complete isolation. So many of these spies that we've looked at, it is the idea of isolation. Do you think Anna liked that sense of isolation,

that private place that she had? I think she did at first. She can be a very private and, you know, sometimes a sullen person also, but very private for sure. It's a very hard situation that you're putting yourself in because you can't talk about your job, your real job, with almost anyone. And you rely so heavily on your handlers, your handlers become almost like your therapists. Those were the most important people to her in her life, because she could be herself with them, you know, confess, if you will, to them and discuss her problems openly.

As Ana's career progressed and got closer to arrest, and there was the WASP arrest in Miami of other Cubans who had infiltrated the U.S., the Cubans basically withdrew. They pulled a lot of their folks out of the region, and Ana's handler went dark for a long time. That really took a toll on her. And then on top of all this, and she's trying to negotiate all of this. She meets and falls in love with Roger, who happens to work at the Pentagon. You know, can you be a spy and fall in love?

Or are the two mutually exclusive? Well, if you're going to fall in love, don't fall in love with someone whose job it is to try to catch Cuban spies. Because that was Roger's job in the world. Honest in a tough place because who do you meet day-to-day? You meet the people that you work with, right? Other folks around you. She fell in love with Roger because she had access to them at work. that's never going to work

it's very difficult if not impossible to leave and they're not going to just let you walk away because you fall in love with someone and just stop spying it just doesn't work that way I don't think Anna knew that when she signed up for this line of work that really added to the stress and kind of torment that she was under

as her career progressed yeah and she did start getting more and more stressed towards the end Did she suspect the FBI was catching up with her? At the very end, she heard the FBI agent talking into a walkie-talkie at one point. She acknowledged this later, but didn't leave. And she had a go bag and escape bag in her apartment and cash and maps. And there was a museum in Mexico City where she was going to flee to if she had to leave the country.

And there was a code that she could press into a pager that the Cubans controlled. So there was a whole apparatus set up if she felt like she was about to be arrested. Why'd you feel she didn't leave then? To just leave, that means leaving your family. Going to Mexico City would have been just a stopover. It means I'm living the rest of my life in Cuba. And I think she just wasn't ready to do that, you know, potentially never seeing her family. again. Do you think there might have been a sense that she thought, I can't carry on with this,

it might be easier if I just let them take me? I don't have any evidence of that at all. Right. Even after she pled guilty, she stood up for her values in the court. She moved to Puerto Rico upon release from prison. And since then, she's, you know, she's made some statements to make it clear she's not changed her stripes. She still feels the same way politically. And I don't think she regrets her decision. I'm sure she's not happy that she got caught and had to spend all that time in prison.

But I don't know that she would do it any differently. There must have been some sense of relief, though. Yeah, I would think so. She, you know, toward the end, especially, it was so incredibly stressful for her. she started showering for really long periods of time using a lot of soap and hot water she started eating a diet of only or primarily boiled potatoes with i think with salt she had all her soap lined up perfectly in the closet of her apartment she you know she was really starting to display some oCD 10 She starts to see her psychiatrist more frequently.

She's taking antidepressants. The walls really started to close in on her tour. I think she probably didn't know how do I get out of this situation where I fell in love with a guy that Cubans don't want me to leave. Yeah. It just got, went from bad to worse for her. It sounds like an extreme case of PTSD in many ways. Yeah, I think so.

I think it became really difficult. to operate and she, you know, became more and more kind of brittle in her personality. It comes to a head to some degree at Lucy's 40th birthday. She invites Anna to South Florida where Lucy lived. And Anna was almost catatonic. She couldn't talk to anyone. She just kind of sat like a lump. And all the friends were like, what is up with her? It just went to what was happening inside Anna's head, the pressure that she was under, and then just the lousy and, you know, kind of weakening relationship between the two sisters. How did Lucy feel when Anna was arrested? Now, it's 10 days after 9-11. Lucy gets called to her boss's office, which was, you know,

really unusual. She was a translator, essentially, you know, language specialist. She gets called to the big boss's office. And she assumes, I'm about to get assigned to a big night. 9-11 case. They walk in, they sit her down, and they say, Lucy, we have bad news for you. Moments ago, your sister, Anna, was arrested in Washington, D.C. Your sister is a Cuban spy. Lucy couldn't believe it. And she fought it at first and said, you're absolutely wrong. This is crazy. As the moments were on, she realized the FBI is not going to make an arrest and make an allegation like this without a lot of evidence. And then slowly she started to think about how her sister had changed over the years. The one other major emotion that Lucy told me about is that she felt

relief. She felt relief. And the reason why was, oh my God, now I understand. Now I understand why Anna has been so weird to me for 17 years. We used to be so close. And so Lucy experienced relief in a way for just understanding the puzzle, the riddle that was her sister. And, I mean, she was obviously very important to the Cubans. She was Fidel Castro's mole, which is quite an odd line to say out loud. But, I mean, the Cubans didn't really seem to care when Arna wanted out. And, I mean, I think this happens in all these cases. It's no, you've got to keep going. And they pushed her to keep going. And do you think the Cubans treated her fairly? I think they used her over time. When she started, keep in mind, they had her

prepare a biography, an autobiography right out of the gates. And this is, you know, pretty common in spy world. But as she's applying, we want to get to know a little bit more about you. So, you know, kind of write down your life history for us. I'm presumably a lot of that is about her dad and what was happening psychologically in the family. I think they probably used that against her. Anna also, as I mentioned, wanted to be needed by the Cubans and by the Americans. So I think they probably played on that as well. You know, in the end, she wants to get out, she wants to go, you know, have a normal civilian life and live with Roger and they won't let her. I think they used her to get what they could from her over time. Doesn't mean they didn't care about her. On the other hand,

they really didn't lift a finger after she was arrested. They issued one kind of positive comment about her, but there was, as far as I know, there was never an offer made, a formal offer made by the Cubans to, you know, exchange prisoners for her, anything like that. So, you know, they got what they needed out of her, and they seemingly moved on. And then did she immediately plead guilty?

Was there any question of that? It was just like, fine, okay, let's get this over with. Well, she's accused essentially of being a spy, you know, upon arrest. The FBI had a little set up where they're trying to get her to admit her crimes. They acted like they thought that her brother and sister also were involved as a way to say, they were hoping that she would say, it's not them, it's me. And she didn't fall for it. She asked almost immediately to lawyer up. She ultimately decided to plead guilty. It was a 25-year sentence. She didn't even serve all 25 years in prison and some of the toughest prisons in the country. One of her cellmates was Squeaky From, Charlie Manson's lover.

That just goes to show you how intense this prison was when there were a lot of very kind of deranged and dangerous people in prison with her in Texas when she ultimately got to Texas. But she could have easily gotten a life sentence. There are other Americans who were convicted of spying for Cuba who got life sentences. And because of her plea deal, maybe because of 9-11, she was allowed to plea. You know, she ended up serving her time and was released from prison.

And she's now under house arrest in Puerto Rico. And that's due to stop in a year or two. Do you have any idea as to what she's planning after that when she's fully free? She's on probation now, so, you know, not technically house arrest. She's living in Puerto Rico. She has some family there. She has supporters. And it's kind of crazy, but there are all these affinity pages on Facebook for Anamontas,

supporting Anamontas as a, you know, hero of sorts. And so she's kind of found her people over there, starting to rebuild her life. She's trying to rebuild her life with her family, with her mother in South Florida. Will she talk? Will she write a book? What else will she do with her life? You know, she's, what, late 60s, I think. And there may be another chapter there for sure.

I mean, are you angling to meet her, Jim? I would love to meet Anna. I don't think I'm her favorite person after having written this book and a long piece for the Washington Post. In fact, and if she listens to this, please give me a call. I've reached out to her lawyer multiple times. But after I wrote a piece for The Post, she wrote to a friend from prison about my article. She said the article really should have been in People magazine.

And what she meant by that was it's tabloidy. This is kind of a trashy version of the story of her life. And so it was not in any way a compliment. It really was meant to say, he focused on all the kind of wrong, salacious elements of my life, but really it should have been a study of American foreign policy from 1898 to present. And if you did meet her, I mean, what would be your first question? I think I'd want to go deep on the why.

Your sister has said that it was ultimately about power and ego. Is that fair? Is that a fair presumption to make about, why you took this enormous risk. If her motivation solely was political, you know, go work for an NGO, work at, you know, work at the State Department and try to change U.S. policy. Go work for a member of Congress who's opposed to U.S. policy in Cuba. It wasn't your only option to spy for Cuba. That's the most extreme option of all. By the way, that wouldn't be my first question because that would be my last question if it were my first question and it's just a very

it's a life of discipline and sadness to me and you know there were moments of joy and she did have a couple really close friends I said some of them have remained super close to her but that's what strikes me about her just the day-to-day boring disciplined element of spying the reality of it. It's a far cry from James Bond. I mean, you know, it is a fascinating story and, you know, it's incredible. I mean, particularly you mentioning that, the connection with Charles Manson. Incredible that it's not been made into a TV show or a film yet. I agree with you.

I think that there's a fantastic, dramatic series waiting to spring forth from this great true material. Well, thank you so much, Jim. It's been a real pleasure speaking to you and getting all. that insight into Anna. Well, thank you so much. Anna Montez is such a fascinating character. She was diligent, hardworking, very disciplined, and I thought it was really interesting what Jim was saying

about this sort of very mundane drudge of what she was doing, of typing up all this information and sending it off to her Cuban contact with seemingly very little reward and you know you wonder what is driving her what was she getting out of it and it keeps coming back to that idea of just really just not liking how she saw America behaving on the world stage and yes Jim talked about dime store psychology but that relationship with her bullying father which then becomes her relationship with a bullying country I think Jim felt too that there is still an enigma at the heart of Arna of really what was driving her and what she was getting out of it.

Thank you for listening and do join us for our next episode of The Spy Who, hosted by Razor Jafri. I'm Raza Jafri, and in the latest season of The Spy Who, we open the file on Morton Storm, the spy who lived inside al-Qaeda. Unfulfilled with his life in a Danish biker gang, Morton Storm stumbles into a library, picking up a book about Islam. He doesn't realize it yet, but that moment will hurl him into a world of radicalism,

seeing him rise within al-Qaeda's inner circle and get caught in the crosshairs of the world's most feared spy agencies. Follow the spy who now, wherever you listen to your podcasts. Wonderry plus subscribers can binge full seasons of the Spy Who early and add free on Apple Podcasts or the Wonderry app. From Wondery, this is the final episode in our series,

The Spy Who colluded with Kastra. This episode of The Spy Who is hosted by me, Charlie Higson. Our show is produced by Vespucci for Wondery, with story consultancy by Yellow Ant. The senior producer is Ashley Clivory. Our sound designer is Alex Port Felix. The supervising producer is Natalia Rodriguez. Music supervisor is Scott Velasquist for Frisson's Sink.

Executive producers for Vespucci are Johnny Galvin and Daniel Turcan. The executive producer for Yellow Ant is Tristan Donovan. Executive producers for Wondery are Estelle Doyle, Theodora Laudis and Marshall Louis.