The Spy Who Colluded with Castro | The A Traitor in the Making | 1

0:00Audible subscribers can listen to all episodes of The Spy Who ad-free right now. Join Audible today by downloading the Audible 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 at thespywho at wondery.com.

0:33The spy who colluded with Castro is dedicated to the memory of Karen Lowe

0:541994. Bolling Air Force Base, Washington, D.C.

1:02Inside 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 Ana Montez, and she's not one for pleasantries. Is this where I sit? Sure is. He steps aside as Montez sits. She's short-haired, athletic, with family ties to Puerto Rico. and she works as an analyst at the Defense 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.

1:51Montez keeps glancing at her watch. Are you ready? I've got a meeting I need to be at. Montez 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 analysing intelligence about Cuba gives her access to some of America's greatest military secrets. Equipment ready, the examiner turns his attention to Montez.

2:38OK, could you raise your arms above your head? He fastens a monitor around her upper chest and another around 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 Anna Berlin Montez? Yes. The first questions are straightforward, to make sure the equipment's functioning and to provide a baseline to compare later answers to.

3:25Is 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.

4:11Are you a spy for a foreign power? He stares at the readings on the plotter. Montez 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 damaging security breaches in its history.

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5:31From Wondery, I'm Indra Varma, and this 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.

6:27But remember, in the shadow realm of the spy, the full story is rarely clear. This is Episode 1. A Traitor in the Making.

6:46It's 1984. Ten years before Ana Montez's polygraph. And in Washington, D.C., Montez 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 Velázquez. Death squads, no more! Stop this contra-war! Death squads, no more! Stop this contra-war! They're both students at John Hopkins University. Montez is completing a master's in international studies. And she and Velázquez 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.

7:38The Contras are a CIA-backed right-wing militia, and they're trying to overthrow the ruling socialist junta, the Sandinistas. Independent lands, future in their hands. The Cuban-bapped 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 Montez 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, Anna. They do it time after time.

8:26Chile, 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. Velazquez stops walking and stares at Montez for a moment. Montez looks puzzled. What? You know, Ana, if you really wanted to do more, there's someone I can introduce you to.

9:11Several 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 from a booth near the back. He makes a beeline to where she's sitting. Next to her is another young woman. Velázquez smiles as she introduces her. This is my good friend, Ana Montez. I've told her about you. Chang Hermann 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.

10:00I'm ashamed at how our government acts. It forced Fidel Castro to seek an ally in the Soviet Union. You're 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, what hope is there for the rest of the world? Chang Hermann gestures towards Montez's T-shirt. On it is a slogan. Support the Sandinistas. Marta tells me you want to help our comrades in Nicaragua.

10:44Yes, 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 have 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 Hedman looks to Velázquez, who makes a subtle nod. Then he makes eye contact with Montez. It is great to know that someone with your intellect and understanding is willing to help.

11:29I'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 Montez look at her friend, who smiles reassuringly. Montez nods. OK, I'll get one typed up. Chiang Hermann smiles. Velázquez was right. Montez has all the makings of a useful agent for Cuban intelligence.

12:00January 1985, Washington, D.C. In her apartment, Montez is reading Foda's Guide to Spain when the phone rings. Hey, Ana speaking? Ana, it's me, Lucy. Montez 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? Montez's blood runs cold.

12:50She's just agreed to spy for Cuba. Now her sisters join the federal agency that hunts foreign spies. She realises 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 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.

13:31That doesn't surprise me. Dad's a complete jerk too. Well, I don't care what you think, Ana. I'm taking the job. Thanks for nothing.

13:46March 1985. A safe house in Havana, Cuba. Cuatro. Tres. Cinco. Ocho. Montez and Velázquez are in Cuba being trained in espionage. Americans are banned from travelling 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 pre-arranged 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.

14:34Montez 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 are learning how to receive instructions from their Cuban spymasters. After the instructor turns off the radio, Montez 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.

15:15It'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 learned there, then I need to make sure I can pass the test, or I could end up in prison. OK, OK. These tests are not reliable. But if the US government thinks they are, then sure, we will teach you how to defeat them.

15:47Six months later, Defense Intelligence Agency, DIA, headquarters, Bolling Air Force Base, Washington, D.C.

15:59Montez 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. Montez follows, but the security guard stops her. I need to check your bag, ma 'am. Montez 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.

16:40Do 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. Montez 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 Montez 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.

17:24We should speak in Spanish. Fewer people will understand us that way. What's that you're reading? Montez 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. Montez studies the menu while Ernesto flicks through the book. Interesting. But do you really think you can memorise 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.

18:05OK. 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.

18:59That's much less suspicious than leaving brown envelopes in tree trunks. OK, we'll try it your way. Montez 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 U.S. intelligence agency and is ready to pass its secrets to Castro's communist regime.

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21:13January 1987 El Paraíso 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 U.S. is supporting the country's military dictatorship in its fight with the FMLN, a force of Marxist guerrillas that are backed by Cuba. Montez follows Staff Sergeant Gregory Fronius through the base. Fronius is a Green Beret, one of the U.S. Special Forces officers sent to El Salvador to help train the Salvadoran army. He briefs Montez as he guides her past columns of marching troops.

22:00We're pretty much on the front line here, ma 'am. Only 58 clicks from the capital. Does that increase the risk of attack? Montez's 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. Montez makes a note of its position before following Fronius into his office.

22:36There'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. The 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. Montez 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.

23:23As 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 Paraíso will be deployed. As far as he's concerned, Montez 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

24:30Two months later, El Paraíso military compound, 2am.

24:39Staff 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.

25:05Fronius 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.