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Wondery subscribers can binge full seasons of the Spy who early and ad free on Apple Podcasts or the Wondery app. Before we begin, a note that this episode contains depictions of violence and may not be suitable for all. And a thank you to our listener Charlotte, who requested that the Spy who Tells the Tale of Ana Montez by emailing us@thespyhoondry.com the spy who colluded With Castro is dedicated to the memory of Karen Low 1994 Bolling Air Force Base, Washington, D.C. inside the offices of the U S. Defense Intelligence Agency, a polygraph examiner prepares his lie detector kit. He looks up as the woman he's scheduled to test walks in without waiting to be invited. Her name is Anna Montes, and she's not one for pleasantries. Is this where I sit? Sure is. He steps aside as Montes sits. She's short haired, athletic, with family ties to Puerto Rico, and she works as an analyst at the Defence Intelligence Agency. It's one of America's less high profile intelligence agencies charged with collecting intel on foreign military capabilities and intentions. The examiner finishes setting up his equipment. Montes keeps glancing at her watch. Are you ready? I've got a meeting I need to be at. Montes seems irritated. That's unusual. Most people seem nervous when they're about to undergo a polygraph, but the examiner doesn't dwell on it. People show nervousness in different ways. Besides, she's not under suspicion. Today is just a routine test, but it's the first Montez has had since joining the dia, and these random security checks matter her current role. Analyzing intelligence about Cuba gives her access to some of America's greatest military secrets. Equipment ready? The examiner turns his attention to Montes. Okay, could you raise your arms above your head? He fastens a monitor around her upper chest and another round her waist. These will keep track of her breathing. Now please roll up your sleeve. He straps a blood pressure monitor to her upper arm and makes sure all the leads are connected to his machine. Then he fastens electrodes around her fingertips to measure electrodermal activity. So I'm sure you know the drill. I will ask you a few questions. You must answer either yes or no. Yes. Great. Is your name Ana Berlin Montes? Yes. The first questions are straightforward to make sure the equipment's functioning and to provide a baseline to compare later answers to. Is your sister named Lucy? Yes. Am I wearing jeans? No. Are we sitting outside? No. He watches for changes in the graph being plotted out by the polygraph machine. All the readings indicate her physiological responses Remain steady when she answers truthfully. If she lies to any of his subsequent questions, the readings should show a sudden spike. Now for the real questions. Did you recently travel to Cuba on official business? Yes. Her answer registers as truthful. Not that he'd expect anything less, but it's his job to check for signs of irregular breathing or a spike in blood pressure when the questions get more pointed. Are you a spy for a foreign power? He stares at the readings on the plotter. Montes has access to military secrets at almost every level. Secrets that enemy spies are out to get access to. If she's a spy, then America will have suffered one of the most most damaging security breaches in its history. I've never felt like this before. It's like you just get me. I feel like my true self with you. Does that sound crazy? And it doesn't hurt that you're gorgeous. Okay, that's it. I'm taking you home with me. I mean, you can't find shoes this good just anywhere. Find a shoe for every you from brands you love like Birkenstock, Nike, Adidas and more at your dsw store or dsw.com from wondery I'm indra Varma and this is is the spy who colluded with Castro. Beneath the veneer of the everyday lurks the realm of the spy. It's a murky world full of dark corners, sinister motives and corrupted morals. A place of paranoia and infiltration, sabotage and manipulation. In this series, we open the file on Ana Montez, the most damaging female spy in US history that we know of. Working as a mole for Cuba, she gained access to America's highest level secrets, stole intel that had deadly consequences, and rendered a multi billion dollar spy program useless. What you're about to hear are dramatized reconstructions of events based on the information that's been made public. But remember, in the shadow realm of the spy, the full story is rarely clear. This is episode one, A Traitor in the Making. It's 1984, ten years before Arna Montes Polygraph and in Washington, D.C. montes is taking part in a protest against U.S. policy in Central America. She's chanting while marching alongside her friend and fellow student Marta Velasquez. Death Squads no more Stop this Contra War. Dead Squad NO more Stop this Contra War. They're both students at John Hopkins University. Montes is completing a Master's in International Studies, and she and Velazquez are furious about US Interventions in Cuba, El Salvador and Nicaragua. Today's protest is a reaction to Congress approving $24 million of aid to the contras. The contras are a CIA backed right wing militia and they're trying to overthrow the ruling socialist junta. The Sandinistas Independent land you've joined their parents. The Cuban Bapt Sandinistas seized power in Nicaragua five years ago. But in the name of fighting communism, the US is supporting efforts to topple them. As the protest dissolves, the two friends head home. But Montes is still fired up. How can this be happening? Innocent people are dying and our government is backing regimes that kill and torture their own people. It's just wrong. Yeah. And it's no one off honor. They do it time after time. Chile, Cuba, Panama, Granada, El Salvador, now Nicaragua. President Reagan says the communists are evil, but look at the blood they spill. And in our names. Yeah. It's like they want another Vietnam. And you know what the most depressing thing is? What? Nobody's listening to us. Don't get me wrong. I think it's important to come here and to speak out. But I'm not kidding myself that these protests will actually make any difference. Velasquez stops walking and stares at Montes for a moment. Montes looks puzzled. What? You know, Anna, if you really wanted to do more, there's someone I can introduce you to. Several months later Manhattan Mian Chang Herman pushes open the restaurant door and steps inside. He's a Cuban intelligence officer working under diplomatic cover at Cuba's mission to the United nations in New York. He looks around and spots Marta Velasquez waving to him him from a booth near the back. He makes a beeline to where she's sitting. Next to her is another young woman. Velazquez smiles as she introduces her. This is my good friend Ana Montes. I've told her about you. Chang Herman slides into the seat opposite them. Ana, it's a pleasure to meet you. Marta tells me you share our frustration with American foreign policy. I'm ashamed at how our government acts. It forced Fidel Castro to seek an ally in the Soviet Union. You are obviously well informed. That is refreshing. Most Americans are too lazy to see what's really happening. Thank you. The US is a bully and somebody needs to stand up to bullies. My family's from Puerto Rico, but we're not treated the same as other Americans. If the US doesn't respect its own citizens, we what hope is there for the rest of the world? Chang Herman gestures towards Montes. T shirt on it is a slogan. Support the Sandinistas. Marta tells me you want to help our Comrades in Nicaragua? Yes. Protests aren't enough. I want to do more. Is there something more I could do? Well, you could translate American policy documents into Spanish for us. That would be useful. That seems kind of menial. I'm a graduate doing a master's degree in international Studies. I've a lot more to offer. You have something in mind? Most of our class are taking jobs in government. I could apply to join an intelligence agency. That way I could help influence government policy. Chang Herman looks to Velasquez, who makes a subtle nod. Then he makes eye contact with Montes. It is great to know that someone with your intellect and understanding is willing to help. I'd like to discuss your offer with my superiors. Would you be able to write a biography of yourself that I could share with them? He sees Montes look at her friend, who smiles reassuringly. Montes nods. Okay, I'll get one typed up. Chang Herman smiles. Velazquez was right. Montes has all the makings of a useful agent for Cuban intelligence. January 1985 Washington, D.C. in her apartment, Montes is reading Fodor's Guide to Spain when the phone rings. Hey, Anna speaking. Anna, it's me, Lucy. Montes pulls the phone over to the couch and gets comfortable. It's been a while since she chatted with her younger sister. When they were kids, they shared a bedroom and talked all the time. Are you at home? Is Mum there? I'm at home. Mum's not here at the moment, and I'm not going to be here for much longer. That's what I'm calling to tell you. You're moving out? I'm moving to Miami. I've got a job with the FBI. You've what? Montes Blood runs cold. She's just agreed to spy for Cuba. Now her sister's joined the federal agency that hunts foreign spies. She realizes that the Cubans might not trust her when they find out about this, and she certainly can't trust Lucy anymore. I said I've joined the FBI. Why do you want to work for the FBI? I want to do my bit for our country. I. I thought you'd be pleased. Sure, every FBI agent I've ever met is a complete jerk. But if you're happy working with a bunch of jerks, then I'm happy for you. I don't understand why you're acting this way. Dad's been really supportive. He told me to go for it, even though Miami's a long way from home. That doesn't surprise me. Dad's a complete jerk too. Well, I don't care what you think, Anna. I'm taking the job. Thanks for nothing. March 1985 A safe house in Havana, Cuba Cuatro, Tres Cincinnati. Montes and Velazquez are in Cuba being trained in espionage. Americans are banned from traveling to Cuba, so they travel to Europe and then use false passports to reach the island. And today they are learning how to receive shortwave radio messages. The friends both listen as their Cuban instructor explains the system. At prearranged times, a series of numbers will be broadcast from a numbers station here in Havana. You must write them on water soluble paper so they're easy to destroy in a hurry. Then you will be given a code to decipher the messages. Montes listens intently. There's been a lot to take in over the past few days on the streets of Havana. They've learned how to spot and lose tails. They've practiced identifying dead drops. Now they're learning how to receive instructions from their Cuban spymasters. After the instructor turns off the radio, I Montes raises her hand. What do we do with the messages once we've deciphered them? You must destroy any notes and remember your instructions. Any other questions? Will we learn how to pass a polygraph test? You don't need to worry about them. These so called lie detectors have no value. It's all pseudoscience. Maybe, but US Intelligence agencies take them seriously. I've applied for a job as an analyst at the Defense Intelligence Agency. If I'm going to pass on anything I learn there, then I need to make sure I can pass the test or I could end up in prison. Okay, okay. These tests are not reliable. But if the US Government thinks they are, then sure, we will teach you how to defeat them. Six months later Defense Intelligence Agency DIA Headquarters, Bolling Air Force Base, Washington, D.C. montes waits in reception, watching a stream of white men in suits enter through the glass doors, flash their IDs at security and head towards the elevator. After a few moments, a man gets out of the elevator and breezes towards her. Ana Montez? Yes. Welcome to the dia. You're going to be working with me to start with, on the El Salvador desk. I'll take you to the office. Follow me. Montes follows, but the security guard stops her. I need to check your bag, ma'. Am. Montes opens her bag and watches as the guard rummages through its contents. Thank you, ma'. Am. He hands her bag back and they head for the elevator. Do they always do bag checks? They're random, but they do them often. Enough. Both on the way in and on the way out. We can't be too careful. You'll get used to it. Sunday lunchtime. Two weeks later a Chinese restaurant in Washington, D.C. montes looks up from her book as her Cuban handler arrives. Ernesto, good to see you. She greets him like the old friend he's supposed to be. Their friendship is pretend, but Montes is pleased to be meeting him for lunch. She doesn't have many friends, and as a Cuban spy, she can't risk getting too friendly with her colleagues at the dia. It's good to see you, too. We should speak in Spanish. Fewer people will understand us that way. What's that you're reading? Montes pushes her book across the table. I thought it might help. How to improve your memory. They do bag searches. Any information I bring from the office has to be carried in my head. It's too risky to remove documents. Montes studies the menu while Ernesto flicks through the book. Interesting. But do you really think you can memorize entire documents? She hands him the menu. Try me. What do you mean? Choose three dishes you'd like to order. Tell me the number on the menu and I'll try to remember what it is. Okay. Number 13, Sichuan Dumplings in spicy red hot sauce. Wow, you're good. Number 23, shrimp soup, hot and sour, 34 deluxe, whole duck with bamboo shoots. And do you know the prices? $3, $2.50 and $25. Your meal will be $30.50. Smart cookie. Shall we order? After ordering, Ernesto gets to business. When you have something for me, we need to arrange a dead drop where you can leave it. Have you identified anywhere? No. No dead drops. They're too risky. Better we meet in person. Let's have lunch here every third Sunday. That feels risky. No, it's better that we hide in plain sight. If anybody sees us, we're just two Hispanic friends having lunch together. That's much less suspicious than leaving brown envelopes in tree trunks. Okay, we'll try it your way. Montes leans back in her chair, pleased with the way things are going. It's nearly a year since she first made contact with the Cubans. Now she works for a US Intelligence agency and is ready to pass its secrets to Castro's communist regime. Look, it's okay to make some financial mistakes. We've all missed payments, signed up for cars we didn't need, or ignored our credit scores. You're not alone. That's why you need Experian, your big financial friend. The Experian app helps you check your FICO score. Find ways to save and get matched with credit card offers that fit your needs. Some cards are labeled no Ding Decline, which means if you're not approved, they won't hurt your credit scores. So, yeah, it's okay if you haven't been the best with your finances. That's why you've got Experian on your side. Download the app for free today. Applying for no Ding Decline cards won't hurt your credit scores. If you aren't initially approved. Initial approval will result in a hard inquiry, which may impact your credit scores. Experian. January 1987 El Paraiso Army Garrison, El Salvador DIA analyst Ana Montez is on her first overseas mission to assess the progress of the civil war in El Salvador. The war is in its seventh year, and an estimated 60,000 people have died. The US is supporting the country's military dictatorship in its fight with the fmln, a force of Marxist guerrillas that are backed by Cuba. Montes follows Staff Sergeant Gregory Fronius through the base. Fronius is a Green Beret, one of the US Special Forces officers sent to El Salvador to help train the Salvadoran army. He briefs Montes as he guides her past columns of marching troops. We're pretty much on the front line here, ma', am, only 58 clicks from the capital. Does that increase the risk of attack? Montes role is to assess how capable the Salvadoran army is of repelling such an attack. Yes, it does, ma'. Am. But this compound is almost impenetrable. And in the unlikely event the rebels gain access, we retreat to this bunker here. Montes makes a note of its position before following Fronius into his office. There's a photo tacked above his desk. Is that your wife? Sure thing. And my two children. They're in Panama. They must miss you. They understand why I'm here. Way I see things, ma', am, is like President Reagan says. El Salvador is closer to Houston than Houston is to New York. If the Communists get a foothold here, then they have a springboard to the rest of America. We can't afford for that to happen. Absolutely not. Privately, Montes disagrees, but she pays lip service to the US Government position that American involvement in El Salvador is vital for homeland security. What I need to know, Sergeant, is if we're doing enough to prevent the rebels from gaining any sort of military foothold here. As you can see, ma', am, security is tight. But we're not just hiding behind gates. There's a major operation planned at the end of March which will strengthen Our offensive capabilities. Fronius unrolls a map and starts pointing out where exactly the troops from El Paraiso will be deployed. As far as he's concerned, Montes is an ally sent here to keep military decision makers in Washington informed about what's happening on the ground. There's no reason to keep her in the dark. Will having that many troops out on operations make this base vulnerable to attack? Every deployment into the field increases vulnerability, ma'. Am. But we'll still have troops here. And there are landmines guarding the approach here. He points to the location of the minefield on the map. Seems like you have everything well covered, Sergeant. Yes, ma'. Am. And security at the base is tight. Everything surrounding those planned operations is strictly need to know. The chances of the rebels learning of our plans are almost zero. Two months later El Paraiso Military Compound 2am Staff Sergeant Greg Fronius jumps from his bed, grabs his automatic rifle and runs outside. What the hell? The base is under attack. Mortars and rockets are whizzing everywhere. Salvadoran troops are scrambling to defensive positions. Armed rebels are already inside the compound. Somehow they got past the landmines. Fronius runs for cover. Intense pain erupts in his left arm. He's hit. He crouches behind a jeep and stays low while bandaging his blood soaked arm. He checks his surroundings. There are FMLN troops everywhere. Salvadoran soldiers are falling. A senior officer runs past and shouts get to the bunker. But it's too late for that. A group of FMLN soldiers are heading towards the bunker and they're carrying plastic explosives. It's almost as if they know exactly where the bunker is and they're here to blow it up. And if they do that, they will kill everyone inside. Fronius picks up his rifle and fires at the insurgents. Some of the rebels fall, but there are too many to take on single handed. Fronius carries on shooting, but feels the sting of bullets ripping into his body and falls to the ground. The 27 year old father lies bleeding and powerless, watching the rebel troops advance towards him. They're carrying an explosive device. When they reach him, the men raise his bleeding body and place the device right underneath him. Several months later the FBI Training Academy Quantico Virginia Montes is with her family. Her brother Tito has just graduated as an FBI agent. Montes takes a photo of him surrounded by the rest of the family. Everybody smile. I think I cut off Dad's head in that one. I'll do another. Dad, can you move in a bit? Now that Tito has the Power to arrest. I'm not sure I should get too close. Make sure you get it this time, Anna. I'm so proud of my family. Family of law enforcers. Montes forces a smile. Her dad has always had a thing about the FBI. He even took them to visit its headquarters on a family holiday. Now almost the entire family seems part of it. Tito's now an agent and his wife is in training. Her sister Lucy works for the FBI's field office in Miami and is dating a colleague. Her dad must be thrilled, but she feels sick. She takes a few more photographs before Lucy calls out to her. Now some with you, Anna. And perhaps a couple on your own, too, to mark your commendation. Montes hands her sister the camera and stands beside her dad. He looks at her. You never told me you had an award, Ana. What was it for? It's nothing really. Just recognition for some work I did related to El Salvador. I can't talk about it. You should take pride in your work. Tell me about it. Seriously, Dad, I can't talk about work. You know that. Anyway, today is Tito's Day. She forces a smile as Lucy takes a photo and backs her up. It's true, dad. Ana could lose her job if she says too much. All you need to know is that she's helping protect our country against the threat of Communism. Isn't that great? Six years later, 1993. Cuba. Montes walked through the back streets of Havana. She's now landed a job on the DIA's Cuba desk. And she's here on official US government business. But now she slipped away from the rest of the DIA team for a secret meeting with her Cuban spymasters. Montes stops outside the safe house door and takes a compact mirror from her bag. She uses it to reapply her lipstick. A passing Cuban shows his appreciation, but Montes is not really concerned with her appearance. She's using the mirror to check she's not being followed. Moments later, she's inside the safe house, ready to brief her handler. I don't have long. If I'm late back, my colleagues will get suspicious. Of course. We don't want to risk this either. You are one of our greatest assets. Since the collapse of the Soviet Union, we are more exposed than ever to American aggression. We are relying on you to counter that. And I am more committed than ever. Good. So what do you have for me? An undercover CIA agent is being sent to Cuba soon. How soon? Do you have a name? I'm working on getting that. But I do have something of immediate value. Part of the reason I'm here is to visit the base at Guantanamo Bay. Cuba permanently leased Guantanamo Bay to the United states back in 1903. But Castro wants the naval base returned. He argues that the deal was forced on Cuba. And Montes spymaster is keen to learn all he can about the base. Tell me what you saw there. A year later DIA headquarters Bolling Air Base Washington, D.C. in a small room, Montes sits in a chair, wired up to a polygraph machine and undergoing questioning. She's been a DIA analyst for almost nine years and she's never yet had to take a lie detector test. She watches the examiner adjust the settings before he poses his next question. Did you recently travel to Cuba on official business? Yes. She knows the first few questions are to make sure the machine is working. But the mention of her visit in Cuba only adds to her nervousness. Montes tenses her sphincter muscles. Her Cuban spymasters told her this controls the blood pressure and fools the machine. The polygraph examiner looks up from his machine. Are you a spy for a foreign power? No. Have you passed classified information to people without clearance? Montes clenches again. No. Did you inform your supervisor about everyone you met during your visit to Cuba? Yes. Thirty minutes later, the examiner stops the questions and starts disconnecting the sensors. Montes maintains her calm. Are we done? Yes. And you're all clear? As I said, it's just a random test. Montes relief soon gives way to renewed confidence. By beating the lie detector, she's proved herself beyond suspicion. She's one of the most senior analysts in the dia, and thanks to this polygraph test, she's just got the green light to carry on spying. Two years later February 24, 1996 the sky above Cuba. In the cockpit of a MiG 29 fighter jet, a Cuban Air Force pilot watches the horizon. He's on the lookout for three U.S. airplanes that were detected in Cuban airspace just minutes ago. He sees them in the distance and radios back to base. Objective insight. Three small Cessnas are puttering on the edge of Cuban airspace. But the control tower wants clarification. He homes in on one of the small twin engine planes. Type and color white and blue, low altitude. It's a Cessna 337. We are locked on. Give us authorization. For months, Cuban exiles in Miami have been flying these planes over the island, dropping anti Castro propaganda leaflets. Cuba has objected to this violation of its airspace, but the exiles have carried on regardless. Now it's time to stop them. The pilot feels impatience. Control, we're locked on. Hell, give us the authorization fire authorized to destroy. Copy. The pilot presses a button. A missile. Missile shoots forward and hits its target. The Cessna is destroyed. The pilot can barely contain his glee. We blew his balls off. Heading to the next target. 8am the following morning. Downtown Washington D.C. two U.S. civilian planes operated by the Miami based group Brothers to the Rescue. Montes listens to the news on the radio as she drives to the DIA offices. Yesterday, Cuba shot down two planes owned by Brothers to the Rescue, a Miami based humanitarian organization run by exiled Cubans. It's known for helping spot refugees fleeing Cuba by sea so that they can be rescued. She hits the steering wheel in frustration. Whatever way this plays out, it's not going to be good for Cuba. But that's not all. Brothers to the Rescue do they also drop anti Castro leaflets over the island? She believes the Cubans have every right to stop them. But now there's a diplomatic crisis and she's been called into work first thing on a Saturday. As she waits at an intersection, Montes spots a familiar figure standing on the corner. Her Cuban handler, Ernesto. He motions to her to pull over. Ernesto, I have to be at work. If I'm not there for this, they'll be onto me. But this is a crisis. I have new orders. I'm aware of the crisis. American citizens are dead and we need to know if the US is going to retaliate. Meet me tonight. I don't know if I can. You must. Cuba needs to be kept informed. Only you are in a position to help us. We must meet every night until this Crisis is over. Twelve hours later, a meeting room inside the DIA's headquarters. Montes watches as her colleague Reg Brown snaps open a can of Coca Cola. They haven't left the room all day. The table in front of them is littered with takeaway boxes. Brown sips his cola and refocuses on the task in hand. We need to identify suitable targets for retaliation. Anna, any suggestions? Montes glances at the clock on the wall. She's already late for her planned meeting with Ernesto. We should be de escalating the situation, not ratcheting up tensions further. Those planes were in or about to violate Cuban airspace. At least one was in international airspace. The President is the commander in chief and he's asked for a list of potential targets. Our job is to supply those targets and let him decide if we strike or not. Our job is to give him the best advice based on our intelligence. My advice is that to strike Cuba now would make them look like the victims and allow them to claim the US as the aggressor, Montes checks the time again. If President Clinton is intent on striking Cuba, then she needs to warn Ernesto. You know what? I'm tired. I'm going home. She stands and picks up her bag, aware of the shocked glances exchanged between her colleagues. It's a national emergency, and nobody is expected to leave until it's over. But she's out of the door before anyone can object. Two MONTHS later DIA headquarters Montes's colleague Reg Brown enters the office of DIA counterintelligence officer Scott Carmichael. Oh, hey, Reg. Come in. Carmichael's a big man with a round, smiling face and a friendly manner. Take a seat. What can I do for you? Despite Carmichael's friendly demeanor, Brown knows he's one of the DIA's most dogged mole hunters, and he's beginning to wonder if he should be bothering him. I'm not sure. I've spent weeks trying to decide if I should say anything, and I don't know exactly what it is I'm trying to say, but my gut tells me it's something. Carmichael tips back in his chair. I put a lot of store by gut instinct. So why don't you tell me what yours is telling you? Ana Montez. What about her? Like I said, I'm acting on a feeling. Brown relays the events of the Brothers to the Rescue crisis, how Montes pushed for de escalation and then left early. Someone told me she took a call moments before she left. Maybe it was her husband, annoyed that she was working over the weekend and missing the kids. Montes doesn't have a husband or kids, or a boyfriend, for that matter. She's all about work. And yet during one of the most important work meetings of her career, she disappears. It's kind of strange, but it's hardly a crime. Is there anything else? She's really pushy. She's always forcing her way into meetings that she hasn't been invited to and she doesn't need to be at. Sometimes you need to be pushy to get ahead. The DIA is a very privileged organization. The people in it often make me feel like a simple Wisconsin farm boy. I can imagine a Latino woman must feel the pressure to prove herself. Sure. And look, I know that she's well respected and that she's earned that, but she seems to see everything from Cuba's point of view. Maybe that's exactly what makes her a good analyst. She's paid to tell us how they think. Carmichael stands up, comes round to Brown's side of the desk and gives him a friendly pat on the shoulder. Listen, I appreciate you coming to me, but maybe your concerns are for hr. It sounds like office politics to me. I'm convinced there's more. I know she's a star and she works hard, and this probably sounds like professional jealousy. Brown breaks off. He wonders if he should just leave now before he damages his own reputation. But then Carmichael speaks. Listen, Reg, whatever it is you came here to say, why don't you just say it, okay? I think Ana Montez is a spy. Brown instantly regrets his words. Carmichael's right. There might be perfectly reasonable explanations for every concern he's raised. He's probably just put his own career on the line here. But what if he's right? Foreign have you got a spy story you'd like us to tell? Email your ideas to the spy who@wondry.com from Wondery this is the first episode in our season the Spy who Colluded with Castro. A quick note about our dialogue. We can't know everything that was said or done behind closed doors, particularly far back in history, but our scenes are written using the best available sources, so even if a scene or conversation has been recreated for dramatic effect, it's still based on biographical research. We used many sources in our research for this season, including True Believers by Scott Carmichael, codename Blue Wren by Jim Popkin, and Queen of Cuba by Peter Lapp. The Spy who is hosted by me, Indra Varma. Our show is produced by Vespucci with writing and story editing by Yellow Ant for Wondery For Yellow Ant, this episode was written by Lizzie Enfield and researched by Louise Byrne with thanks to Marina Watson. Our managing producer is Jay Priest for Vespucci. Our senior producer is Ashley Clivery. Our sound designer is Alex Port. Felix Natalia Rodriguez is the supervising producer. Music supervisor is Scott Velasquez for Frisson Sync. Executive producers for Vespucci are Johnny Galvin and Daniel Turkan. Executive producer for Yellowant is Tristan Donnifie. Our senior producer for Wondery is Theodora Luludis. Executive producers for Wondery are Estelle Doyle and Marshall Louis. Wondery plus subscribers can binge full seasons of the Spy who early and ad free on Apple Podcasts or the Wondery app. It's okay not to be perfect with finances. Experian is your big financial friend and here to help. Did you know you can get matched with credit cards on the app? Some cards are labeled no Ding decline, which means if you're not approved they won't hurt your credit scores. Download the Experian app for free today. Applying for no ding decline cards won't hurt your credit scores if you aren't initially approved. Initial approval will result in a hard inquiry which may impact your credit scores. Experian.
Original Air Date: September 30, 2025 | Host: Indira Varma, Raza Jaffrey
The series premiere of "The Spy Who" unpacks the chilling true-life story of Ana Montes, deemed the most damaging female spy in U.S. history. Driven by ideology and resentment toward U.S. policy in Latin America, Montes becomes a mole for Cuba, infiltrating the Defense Intelligence Agency (DIA) and handing over high-level military secrets for decades. Through dramatized reconstructions based on solid reporting, this episode traces her radicalization, recruitment, and first years as a Cuban spy — all while her own family rises through the ranks of American law enforcement.
[00:00–07:06]
[07:07–14:54]
"How can this be happening? Innocent people are dying and our government is backing regimes that kill and torture their own people. It’s just wrong."
[09:10]
[14:55–22:07]
"It’s great to know that someone with your intellect and understanding is willing to help.”
[18:37]
[22:08–27:34]
“Every FBI agent I’ve ever met is a complete jerk. But if you’re happy working with a bunch of jerks, then I’m happy for you.”
[24:46]
[27:35–34:18]
“If I’m going to pass on anything I learn there, then I need to make sure I can pass the test or I could end up in prison.”
[31:42]
[34:19–41:57]
[41:58–52:25]
[52:26–57:52]
"Seriously, Dad, I can't talk about work. You know that. Anyway, today is Tito’s day."
[56:13]
[57:53–1:04:16]
"By beating the lie detector, she's proved herself beyond suspicion."
[1:04:02]
[1:04:17–1:14:11]
"Our job is to supply those targets and let [the president] decide if we strike or not."
[1:11:09]
"If President Clinton is intent on striking Cuba, then she needs to warn Ernesto."
[1:12:49]
[1:14:12–1:21:35]
“I think Ana Montes is a spy.”
[1:21:24]
Montes on ideological motivation:
"I'm ashamed at how our government acts. It forced Fidel Castro to seek an ally in the Soviet Union."
[18:02]
Cuban instructor's dismissive advice:
“These so-called lie detectors have no value. It's all pseudoscience.”
[32:03]
Montes’s handler on hiding in plain sight:
“No, it’s better that we hide in plain sight. If anybody sees us, we’re just two Hispanic friends having lunch.”
[39:50]
Family irony:
"All you need to know is that she's helping protect our country against the threat of Communism. Isn't that great?" (Lucy about Ana)
[57:37]
Montes after passing polygraph:
“By beating the lie detector, she’s proved herself beyond suspicion.”
[1:04:02]
Episode 1 of "The Spy Who Colluded with Castro" offers a gripping introduction to Ana Montes—motivated by ideology, schooled in tradecraft, operating in the shadows, and ultimately, hiding in full view among law enforcement kin. Her duplicity goes unnoticed for years, leaving listeners both stunned by her skill and chilled by the ease with which she evaded detection—at least for now. The seeds of doubt and suspicion planted here promise a riveting continuation as the series exposes the depth and cost of her betrayal.
*Sources referenced in the episode include: