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Indra Varma
Wondery plus subscribers can binge full seasons of the Spy who early and ad free on Apple Podcasts or The Wondery app. November 1996 Clarendon, Virginia Anna Montez strides through the Virginia office of the Defense Intelligence Agency, keeping her eyes straight ahead and walking with purpose amid the buzz of activity around her. But her body is pulsing with adrenaline. She's been summoned to an interview with the DIA's senior counterintelligence investigator, Scott Carmichael. With no explanation why, she battles to suppress her rising fear. Could this be it? Could her own agency have discovered she is a Cuban spy? But if it had, wouldn't she already be in handcuffs? Montes struggles to maintain her icy calm. This could be the end of everything. She reaches Carmichael's door, pauses, exhales and knocks. Montes pushes the door open and steps inside. Carmichael sits behind his desk, chubby with an unruly mop of straw blonde hair. Montes gives him an irritated glance, then tries to take control of the conversation. Mr. Carmichael, I can only spare a few minutes. This is a very busy day. Carmichael pitches forward in his chair, the hint of a smile twisting the corners of his mouth. Ms. Montes, I'm responsible for the security of this agency. This will take as long as it takes. Montes feels wrong footed. She mistook Carmichael's unkempt appearance for weakness, but he's just let her know that he's in charge and that this meeting is serious. She breathes slow, forcing herself to stay calm as she sits opposite Carmichael. Can I ask what this is about? Sure you can. Concerns have been raised about whether you have connections to a foreign intelligence agency, namely Cubers. What? Are you serious? Montes affects a tone of indignation. This is now a duel. A single slip on her part and her double life could catastrophically unravel. Am I under investigation? No, you're not under formal investigation, but there are some questions we need to clear up. Montes feels a surge of relief that she is not under official investigation. She nods and switches to a helpful conciliatory tone. Well, of course I'll help in whatever way I can. Excellent. Thank you. Now, Ms. Montes, you remember a few months ago when Cuba shot down the two brothers to the rescue planes? Yes, of course. Well, on that Sunday after the planes were shot down, I understand you left work early, around 8pm Montes's eyes narrow. 8pm is not early. I had come in at around 8 in the morning and I was completely exhausted. And where did you go after you left? I went straight home to bed and could anyone confirm that? Well, I live alone. I suppose one of my neighbors might have heard me come in, but it would probably be a little ridiculous to ask someone if they heard me on the stairs on a random Sunday evening six months ago. Montes feels her confidence rising. If this is the sort of evidence they're throwing at her, it's incredibly thin. Carmichael shifts in his chair. I heard you often question US Policy towards Cuba in meetings. Well, yeah, that's my job. I'm meant to study and understand the Cuban regime and to stress test our policy towards it. Of course, I question things because I'm good at my job. Carmichael shuffles the papers on his desk, then looks up at Montes. Well, thank you, Ms. Montes. You've been most cooperative. I'll let you know if we need anything more from you. Montes nods, stands, and walks towards the door. Her mind is still racing. She feels waves of relief that this round of questioning amounted to nothing, nothing more than weak insinuations. But that there is even a hint of suspicion about her is troubling. From now on, she needs to operate with even more care and precision. In the game she is playing, the stakes couldn't be higher.
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Indra Varma
From wondery. I'm Indra Varma and this is the spy who colluded with Castro in the last episode. DIA analyst Ana Montes began sharing U.S. military secrets with Cuban intelligence while her brother and sister joined the FBI. But as she gains access to ever more valuable secrets, the risks of being exposed as a spy are rising. This is episode two in this building 10. 98 February 1996 years before Anna Montez met with Scott CARMICHAEL CAPE CANAVERAL, FL Inside Mission Control, two officials from the National Reconnaissance Office stare up at a bank of monitors on the screens. The space shuttle Atlantis blasts off towards the stratosphere. 3. 2, 1. Ignition. The National Reconnaissance Office, or NRO, is the agency that operates America's spy satellites, and for the nro, this is a high stage mission. On board the space shuttle Atlantis is a new, state of the art and highly classified satellite codenamed Misty. But it's hard to launch a spy satellite in secret. The NRO officials know that as soon as Misty is put into orbit, both the Soviets and amateur space watchers across the world will be tracking its every move. But the NRO has a plan for that. Eight months later Cape Canaveral Mission Control the two NRO officers once again stare up at the bank of monitors, observing the orbit of their top secret satellite. Misty, one of the officers turns to the other and gives a nod. The second officer leans down to the control desk, pauses for a moment, then presses a button. The officers look up at the screens once more, just in time to see a large flash as the multi billion dollar satellite explodes in a shower of debris. The two officers look at each other and smile. Everything's gone exactly to plan. Six and a half years later May 1997 Bolling Air Force Base, Washington, D.C. ana Montez sits in a secure room at the DIA headquarters, maintaining a relaxed, businesslike poise. Six months have passed since she was questioned by DIA counterintelligence officer Scott Carmichael. Since then, she's had her security clearance increased, and that's reassured her that she is no longer under suspicion. It's also why she's been invited to today's briefing by the nro. She listens carefully as one of the visiting NRO officers begins his presentation. Thank you for joining us today. We're here to bring you up to speed with a program we call Misty. The NRO officer switches to a slide showing a space shuttle launch. We launched the first misti satellite in 1990. We knew the Soviets would immediately begin tracking it, so six months later, we staged a decoy explosion to make it look to the Russians as if our satellite had malfunctioned. The agent switches to a grainy still image of the satellite's detonation. Montes frowns and interrupts. Wait a minute. If the Russians were tracking the satellite, wouldn't they notice that it's still there after the explosion? The NRO agent smiles. Exactly right. But this was a double bluff. The explosion gave us cover to activate Misty's unique cloaking technology. Now, satellites that collect signals intelligence, that is those that intercept calls and other electronic communications, give off a specific electromagnetic fingerprint. Satellites that take pictures emit a different fingerprint, and those fingerprints can be detected from the ground, revealing the purpose of the satellite. Misti's cloaking technology makes it appear to be a signals intelligence satellite, when in fact it takes pictures. Another member of the NRO team interjects. So every time it passes overhead, the Russians stop talking on the phone, when in fact they should be hiding their tanks in underground bunkers. Montes eyes widen at the audacity and sophistication of the operation. This covert satellite is tricking foreign powers and harvesting an intelligence bounty on the back of it. This gives the US a massive advantage in understanding what what other countries are up to. Montes knows that this information would not only have immediate value to her Cuban handlers, not least because Cuba could make millions of dollars selling this intel onto Russia, China, Iran, or any of America's geopolitical rivals. The NRO officer continues his presentation with a smug grin on his face. Now, Misd is a multi billion dollar program and highly classified. It's really one of the jewels in the crown of U.S. espionage. Montes heart races in her chest. She feels an immediate compulsion to inform her Cuban contacts about this program. But she also knows that divulging intelligence of this magnitude would not just be considered espionage, but treason. This is a secret so big that if she were caught sharing it with the Cubans, she could face the death penalty. A few weeks later, Washington, D.C. montes leans back in a soft chair and looks around at the soothing abstract art in her therapist's dimly lit office. She runs her hands through her short, tightly cropped hair, then presses her palms to her eyes. I'm not sleeping well right now. Just feels like. Like the walls are closing in. The therapist crosses her legs, a concerned look in her eyes. Is there anything specific that's been going on? There's a big decision I have coming up at work. I can't talk about the specifics, but this decision, it could be really crucial and I don't know which way to turn. But I need to make the right choice. Ever since the NRO briefing, Montes has been wrestling with whether to reveal the secrets of the misty satellite program to her Cuban contacts. She always wanted to change the world. Now she has the power to do just that. On the one hand, it would be a tremendous aid to Fidel Castro's regime, a chance to rebalance the geopolitical order and she feels duty bound to play her chosen part. But it would also be by far the most high level information she has ever passed over. It would render the multi billion dollar spy satellite program completely useless and she would literally be putting her own life at risk. Her therapist leans forward. Anna, when you talk about needing to make the right choice, do you often feel this need for perfection? I think so, yeah. Do you think that might have something to do with your father? In one of our previous sessions you have mentioned that you felt he was harder on you than on your siblings. Montes stiffens in her chair, her eyes flashing. I don't just feel that, I know it. He was a bully and I had to protect them. Often when an older sibling has to step into that role of protector, it can leave them feeling hyper vigilant, like they're responsible for everything. Do you think your siblings appreciated what you did for them? Montes slumps as the weight of memory and loneliness crashes down on her. I don't know. It's sometimes like we grew up in different homes. They think we were this great family. But I see the problems, the hypocrisy, and I'm not willing to just sit there and pretend it isn't happening. It's like there's this wall between us now and they'll never see the real me. It must be lonely, never showing the real you. Have you ever tried just letting your guard down and seeing if they accept you for who you are? They may well surprise you. Montes puts her head in her hands. I can't. I just can't. They'd never understand. The therapist pauses for a moment, then checks the clock on the wall. Listen, Anna, I'm afraid we have to stop now. I think we're making progress, but I'd like to continue with the antidepressants while we continue to work through this. I'll write another prescription. A few days later, Washington, D.C. it's midnight and Montes sits in her apartment, illuminated by the glow of her Toshiba laptop. After some deliberation, she's decided to tell her Cuban contacts about Misty. The chance to help Cuba and disarm America's spy satellite advantage is just too important. She can't let this opportunity slip by. She finishes typing her report to the Cubans, recounting everything the NRO told her about Misty. Montez slams the save key, then pops the floppy disk out of the drive. She opens a new application. It's called Wipe. She got it from the Cubans, and it will erase all evidence of her recent activity from the laptop's hard drive. Montes leans back in her chair and exhales loudly in relief. Her decision is made. The next day, Montes steps inside the Chinese restaurant in downtown Washington, where every few weeks she has lunch with her Cuban handler, Ernesto. Ernesto is already there, waiting. He stands and they kiss on both cheeks in greeting. As they sit, Ernesto smiles at her. How are you? You seem happy today. I always like our meetings. Montes feels relaxed around Ernesto. He's the only person in the world who knows about and understands the double life she leads. He slides the drinks menu across the table. Perhaps you'd care for a glass of wine. Montes pretends to scan the wine list, then almost imperceptibly slips the floppy disk with the information about Misty between its faux leather covers. Actually, I'm going to stick with water today. She slides the drinks menu back across the table. She watches as Ernesto discreetly transfers the disc to the inside pocket of his blazer. She leans forward. I have to ask the computer program. It really does clean the laptop properly, right? Ernesto looks her in the eye. Of course. Absolutely. Good. Because what I just gave you is big. Really big. With multiview from Xfinity, you can watch up to four football games at once, which can lead to some tough choices. French toast nibblers or breakfast nachos. Actually, I was thinking about heading out. Only because I want to beat the traffic.
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Indra Varma
The games on Bobby Big Wheels.
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That's okay.
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Indra Varma
April 1998 Fort Meade, Maryland Elena Valdez stands in a secure conference room at the headquarters of the National Security Agency. The NSA is the US Spy agency that monitors and decrypts communications made by America's enemies and occasionally even its allies. But its activities are restricted to gathering and analyzing information. So when it finds evidence of spying on U.S. soil, it needs to call in the FBI. And that's what's happening today. Valdez is an officer with the NSA, and seated in front of her are 20 FBI counter espionage agents. She assumes an ice cold professional demeanor to match their macho energy. Okay, thanks for joining us today. We called you in because we've intercepted and decrypted significant electronic communications from Cuba. These communications indicate that the Cubans have a spy placed at a high level within a U.S. intelligence agency. We're calling this person Agent S. One of the FBI agents looks up at Valdez. All right, what do we know? We believe Agent S is a man. The intercepts refer to him as male. We also know that he purchased a Toshiba 405 CS laptop at the Cuban's direction in October 1996. This purchase was made at an unknown store in Alexandria. The FBI agent pipes up again. Wait. Which Alexandria? Valdez suppresses her irritation. Well, if they work at an intelligence agency, chances are they're based near Washington. So Alexandria, Virginia would be the obvious bet. We also know they use 3.5 inch floppy disks to pass intelligence to their Cuban handlers. Also, in July 1996, Agent S visited the U.S. base at Guantanamo and stayed there overnight. Oh, and they apparently have access to something called safe. The same FBI agent interjects. What's safe? We're not sure right now, though. From the intercepts, the Cubans thought this was a big deal. Is this all you've got? A man who works in intelligence in the D.C. area? It's pretty thin. Valdez sees some of the other agents stifle yawns. Frustration rises within her. For her, this is personal. Her family fled Cuba when she was just six years old. She despises Castro's dictatorship and has dedicated her professional life to combating it. Look, I get that this feels like a needle in a haystack, but we all know how the Cubans operate. They recruit naive students who think Che Guevara is some sexy guy on a poster, not a vicious killer. And we know that Cuban intelligence sells our secrets to serious enemies like China, Russia, and North Korea. If they have someone high up in our agencies, we need to find them. Valdez scans the faces of the agents in the room, telling herself that for all their professional skepticism, once the FBI start an investigation, they don't stop till they get their target. She feels confident that even from this modest start, they're going to root out Castro's mole. September 1998 Washington, D.C. anna Montes once again sits across from her Cuban handler, Ernesto, at their favorite Chinese restaurant. They've just executed their usual maneuver, passing a floppy disk loaded with US Defense Intelligence hidden in the Trinks menu. But now Ernesto's usual charming smile shifts to an almost pained expression. Ana, I have to tell you something. This is the last time we will meet here. I'm being pulled out. Anna feels the blood rush from her face. These meetings with Ernesto have become the highlight of her month. They are her only chance to have the true scale of her work recognized, her sole opportunity to speak to someone who understands the constant pressures she lives under. Ernesto sees her expression sag and continues with concern. You heard about the agents the FBI arrested in Miami? It's no longer safe for us. A few days ago, the FBI busted a Cuban spy ring in Florida, generating headlines across the country. Montes heart begins to race. Is it because my sister works for the FBI in Miami? Am I being punished? Ernesto places his hand on hers across the table. No. God, no. We're not cutting you off. We would never do that. You're too important. You're the best we have. That's why I must leave to protect you. If I stay, they might locate me, and that would put you in danger. Montes scrambles to pull herself together. She won't show weakness in front of Ernesto. She will present herself as a soldier dedicated to the cause. Who is going to replace you? No one. It's too dangerous. From now on, all communication will will be done remotely. He slips a folded piece of paper under the table. These are pager numbers and a cipher to use for messages. Use those to keep in touch. Always call from a payphone and never use the same payphone twice. How will I transmit detailed information? I can't do that with a pager number every six months or so you can take a vacation somewhere sunny in the Caribbean. That's where we can meet and exchange the usual floppy disks. Montes nods, still struggling to maintain her calm, determined exterior. But it is Ernesto whose expression softens. I'll miss our lunches together. Me too. Ernesto smiles and opens the menu. Well, we can still enjoy this one at least. What will you have? Montes stares blankly at the menu, feeling more alone than ever without even Ernesto to speak to. It really is now just her and her cause. Eight months later, May 1999 Montes sits at her cubicle amidst the bustling activity of the DIA's Washington headquarters. Her hand snaps out automatically, grabbing her phone from its cradle before the second ring. Montez. Montez's entire body tenses, her knuckles whitening around the phone. She is being summoned to see Dave Curtin, the chief of the DIA's regular regional military Assessments group and several ranks her superior. Okay, I'll be right up. Montes feels the panic rising within her. Why would Curtain want to see her so urgently? This is unprecedented. Images of handcuffs and prison cells flash through her mind. There's only one explanation. They must be onto her. She's about to be arrested. On arrival at Curtin's office, his secretary gestures for her to sit outside his closed door. Five minutes pass, then ten. Montez's hands clasp the arm of her chair so tight her wrists begin to ache and the tips of her fingers go numb. The pounding in her chest is excruciating. Eventually, the door swings open and Curtin motions her inside. Montes walks into the office as if she's walking towards a firing squad. But the moment she's inside, Curtin turns to her with a huge smile on his face. Anna, I've got excellent news. You're being promoted to GG14. What? GG14 is a federal government pay scale. It's a huge promotion with a big leap in both pay and prestige. Thousands of employees across America's spy agencies would have been in competition for this honour, and it's extremely rare that a DIA analyst would achieve the rank. But for Montes, it's all too much. The accumulated tension of the walk upstairs and long wait outside, the certainty that it was all over and it all now comes rushing through her body. She momentarily loses her balance and almost passes out, collapsing into a nearby chair and sending a lamp crashing to the floor. Curtin grabs hold of her upper arm. Whoa there. I know it's good news, but steady, huh? You were nominated for the Exceptional Impact Promotion Program and selected by an independent board. Please accept the agency's congratulations on your outstanding work. I. I don't know what to say. Thank you, sir. Montes manages to pull herself together enough to accept the congratulations, but inside she almost can't bridge the intellectual gap between the fact that she is an active high level spy for a so called hostile regime, but is being honored as one of America's top intelligence agents. The pressures and contradictions of her double life are growing more acute every day. A year later early 2000 Elena Valdez stares at at the phone on her desk at the NSA's headquarters in Fort Meade, Maryland. It's been two years since she briefed the FBI on the presence of a Cuban spy high up in the US Security apparatus, but as far as she can tell, nothing has happened. Every few weeks she has called FBI headquarters, but it feels like she's been given the runaround. She sighs to herself, picks up the phone and dials the FBI case officer's secure line once more. Hello? Hi, it's Elena Valdez over at the NSA calling once again about our case. Look, Ms. Valdez, I know you've been pursuing this, but we have other priorities right now. Other priorities? We have a Cuban spy high up in US Intelligence. What could be a higher priority? Hey, the NSA gathers intel, but it's the FBI that decides what to investigate. How about you do your job and let us do ours, okay? The case is closed. Damn it. A colleague sees Valdez's anger and leans over. Hey, what's up? The goddamn FBI. I've given them seriously important stuff and they're doing nothing. Yeah, you know what they're like. They all think they're God. They try to teach the Pope to be Catholic and bears to shit in the woods. Valdez's face turns steely. Yeah, well, they can say this case is closed, but like hell it is. Not while I'm around. Valdez smiles to herself. An ironclad resolution not to let this case drop. September 2000Fort Mead, Maryland Elena Valdez hangs around the coffee and snacks table at a conference room inside her NSA office. She's just sat through a roadshow presentation by several DIA officials and now hopes to talk to one of the speakers. It's been several months since the FBI told her the agent s case was considered closed, but she has not let it rest. Instead, she's been covertly hunting around for information amongst America's various intelligence agencies, and something in the DIA presentation she's just sat through has caught her attention. She approaches the speaker as he pours himself for coffee. Hi there. Elena Valdez. I'm with the NSA's Cuba desk. Did I hear correctly that you have a specific Cuban counterintelligence team at the dia? The speaker, a tall, friendly looking man, reaches out to shake her hand. Yeah, I actually work on that team. I just finished a research paper on Cuban sponsors censorship of terrorism in Latin America. Valdez smiles back. Oh yeah, I'd love to read that. You should publish it. Actually, I think the wider intelligence community would benefit. I don't think enough of our people understand how Cuban intelligence operates over here. Oh, I'd love to, but that's probably not going to happen. The DIA man's face seems to darken, peaking Valdez's curiosity. No. Why not? There's this woman, she totally outranks me. Over at dia, everyone calls her the Queen of Cuba. She basically runs everything to do with Castro and she refuses to sign off on my report. So no dice. Now Valdez's curiosity is really piqued. Huh. No kidding. What's this lady's name? Ana Montez. She's smart as hell, but honestly, between you and me, she's kind of a grade 8 bitch. Valdez nods sympathetically. She doesn't appreciate this guy's language about women, but she realizes that she has failed to really consider the dia. It's an agency that often flies under the radar, overshadowed by the profile of the CIA or FBI. But now that she's learned about its so called Queen of Cuba, she feels like it's time to pay the DIA a visit. One week later Bolling Air Force Base, Washington, D.C. valdez sits in a Sensitive Compartmented Information Facility, or SCIF, inside the DIA's headquarters. SCIFs are secure rooms totally off the grid where ultra classified conversations can be conducted safe from enemy espionage. Across from her sits Chris Simmons, an analyst on the DIA's Cuban desk. Lean with an alert military air. He regards Valdez with a businesslike attitude. Welcome to the DIA, Ms. Valdez. What can I do for you? Valdez pauses a moment, gathering her nerve before replying. Look, Mr. Simmons, I'm going to level with you. This isn't a routine grab and grip smile in a handshake meeting. We've got intercepts that show there's a Cuban spy who has infiltrated the highest levels of US intelligence and we need to find them. Simmons raises his eyebrows. Well, that sounds like a matter for the FBI. I briefed the FBI on this two years ago, but they tell me they've got other priorities Simmons gives Valdez a look that seems to mix curiosity with concern. Ms. Valdez, do you have permission from the NSA to be telling me all this? Valdez hesitates, then pushes on, ignoring the question. This is too important to get lost in a stack of other cases. Let me just run you through the bones of what we've got just to see if anything jumps out. Simmons gives the slightest nod. The two share a complicit glance, an acknowledgement that they both know this is outside of regulations and a huge risk for both of them. We're calling this guy Agent S. We know he stayed overnight at the Guantanamo Bay Naval base in 1996. We know he bought a Toshiba 405 CS laptop from a store in Alexandria. And while we don't know what it is, we know he has access to something called safe. Wait, what did you say safe? Simmons sits bolt upright, his eyes fixed on Valdez. Yeah, safe. You know what that is? You're damn right I do. That's the Secure Analyst File Environment, the DIA's internal database. Valdez and Simmons lock eyes across the table, the lightning strike of this revelation hitting them both at the same time. It's Simmons who says it first. If your Agent S has access to safe, it means. It means they're in this building right now. September 2000 A few days later, Washington, D.C. montes walks down the National Mall arm in arm with her new boyfriend, Roger. Roger is an intelligence officer for the Department of Defense who works at a major military base in Durrell, Florida. The couple met on a work trip several months ago and have been carrying on a long distance relationship. They pause in the evening sun and look up together at the Washington Monument, pointing up towards the sky. Roger turns to Montes. It's quite something, huh? Sure is. Would you ever think about moving to Washington? Hmm. I don't know. Would you ever consider moving to Florida? Hell no. That was a little quick. I'm at headquarters now, right in the middle of things. I'm not going to move to some field office. Roger looks almost hurt by Montes's straight from the gut answer. Florida does have some other attractions, you know. Nice beaches. Your family are there. I'm there. I know. I'm sorry. It's just my work is here. My life. I've worked so hard to get where I am. Montes slips her arm around Roger's waist, pulling him close. Suddenly her mind flashes to the shortwave radio stashed under the bed in her apartment. There are so many parts of herself she has kept concealed for so long, so much that her life depends on keeping hidden. If she and Roger were to ever live together, her spying for the Cubans would become simply impossible. A wave of unfamiliar emotion washes over Montes images of all she has given up over the years in pursuit of her cause. Friendship, love, intimacy, family. For perhaps the first time in her life, she begins to wonder if there might be something for her in life beyond espionage and deception. About the same time DIA Offices Clarendon, Virginia DIA counterintelligence Officer Scott Carmichael settles down in his office with his partner. Carmichael has just had an emergency briefing from Chris Simmons. At the briefing, Simmons informed him of the lightning bolt revelation he and Elena Valdez shared that there is a Cuban spy inside the dia. Now it's Carmichael's job to catch that spy. He looks over to his partner. His name is Karl James, but everyone calls him Gator. Hey, Gator, what you want to bet that I catch this spook before you do? Gator looks around the office, then peers out at the red glow of the vending machine down the hall. How about one can of Coke? All right, but it's gotta be full fat, none of that diet crap. Alright, you're on. Carmichael settles into his leather chair, staring at the computer screen glowing in front of him. He knows that one of the few facts that the NSA has about Agent S is that they visited the naval base at Guantanamo Bay in July 1996. So that's where Carmichael starts. He pulls up the lists of every DIA official who registered at the base as a visitor during that month. His eyes flick over column after column of names. Then one name leaps out at him. He freezes, catches his breath, then reads the name back to himself. Ana Montes, the analyst he himself interviewed after a colleague suspected her of spying four years earlier. Carmichael smashes his hand down on his desk in excitement. Hot damn, Gator. You better have some change for that Coke machine. Gator lifts his head from his own screen, spinning around in his chair. What? You're kidding me. Don't tell me you've got our guy already. Carmichael Fix is his partner with a triumphant smile. Oh no, buddy. This ain't no guy. Have you got a spy story you'd like us to tell? Email your ideas to the spy who@wondery.com from this is the second episode in our season, the Spy who Collaborated 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 Believer by Scott Carmichael, codename Blue Wren by Jim Popkin, and Queen of Cuba by Peter Lapp. The Spy who is hosted by me Inderavama. Our show is produced by Vespucci with writing and story editing by Yellowant for Wondery. For Yellowant, this episode was written by J.S. raffaelli 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 FrisonSync. Executive Producers for Vespucci are Johnny Galvin and Daniel Turkan. Executive Executive producer for Yellowant is Tristan Donovan. Our senior producer for Wondery is Theodora Luludis. Executive producers for Wondery are Estelle Doyle and Marshall Louie. Wondery plus subscribers can binge full seasons of the Spy who early and ad free on Apple Podcasts or the Wondery app.
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Indra Varma
Experience.
Podcast: The Spy Who
Hosts: Indira Varma, Raza Jaffrey
Date: October 7, 2025
Duration: ~45 minutes (excluding ads, intros, outros)
This mesmerizing second installment of "The Spy Who Colluded with Castro" charts the high-stakes cat-and-mouse game unfolding within the heart of U.S. intelligence. The episode dives deep into the double life of Ana Montes—a Defense Intelligence Agency (DIA) analyst covertly passing America’s most sensitive military secrets to Cuba. As suspicion steadily mounts and investigative nets tighten, the episode weaves through tense interrogations, secret intelligence briefings, and the psychological toll of treason. Key rivalries and suspicions among NSA, FBI, and DIA bureaucracies amplify the drama, showing not just how one woman outmaneuvered the U.S. security apparatus, but also how cracks within America’s own agencies enabled her deception.
(00:00 - 04:57)
“If this is the sort of evidence they're throwing at her, it's incredibly thin.”
— Indira Varma (narration), 03:57
(06:36 - 14:00)
“It would be a tremendous aid to Fidel Castro's regime, a chance to rebalance the geopolitical order.”
— Indira Varma (narration), 12:37
"Because what I just gave you is big. Really big."
— Ana Montes to Ernesto, 18:34
(20:24 - 27:00)
"We all know how the Cubans operate. They recruit naive students who think Che Guevara is some sexy guy on a poster, not a vicious killer."
— Elena Valdez, 24:48
"If they have someone high up in our agencies, we need to find them."
— Elena Valdez, 25:15
(27:00 - 31:00)
"You’re the best we have. That’s why I must leave to protect you. If I stay, they might locate me, and that would put you in danger."
— Ernesto to Ana Montes, 29:09
(31:00 - 34:45)
(34:45 - 41:00)
"If your Agent S has access to safe, it means—they’re in this building right now."
— Chris Simmons to Elena Valdez, 40:46
(41:00 - 43:50)
"Oh no, buddy. This ain't no guy."
— Scott Carmichael to 'Gator', 44:25
| Time (MM:SS) | Segment | Summary | |:--:|:------------------------------------|:-------------------------------------------| | 00:00–04:57 | Montes' Interrogation at DIA | Ana sidesteps counterintel suspicions | | 06:36–14:00 | Misty Satellite Briefing | U.S. satellite deception; Ana’s moral crisis| | 20:24–27:00 | NSA Tips FBI/Inter-Agency Clash | Valdez struggles to get the FBI engaged | | 27:00–31:00 | Ernesto’s Departure | Ana loses her Cuban handler, feels isolated| | 31:00–34:45 | Tense Promotion | Ana receives career honor while spying | | 36:00–41:00 | Valdez Investigates DIA | Inter-agency breakthrough—focus on Montes | | 41:00–44:25 | Carmichael Zeroes In | U.S. counterintel closes in on Ana |
The episode is narrated in a suspenseful, cinematic style, blending dramatic reconstructions with factual investigative prose. Characters’ emotions are artfully drawn: Ana’s nerves and rationalizations, Valdez’s indignation and persistence, Carmichael’s mix of skepticism and exhilaration, and even the understated tragedy of Montes’ personal sacrifices.
Montes’s Internal Calculation:
"This is a secret so big that if she were caught sharing it with the Cubans, she could face the death penalty."
— Indira Varma (narration), 11:43
Valdez on Cuban Recruitment:
"They recruit naive students who think Che Guevara is some sexy guy on a poster, not a vicious killer."
— Elena Valdez, 24:48
Carmichael’s Triumph:
"Hot damn, Gator. You better have some change for that Coke machine... Oh no, buddy. This ain't no guy."
— Scott Carmichael, 44:20
Ernesto’s Farewell to Montes:
"You're the best we have. That's why I must leave to protect you."
— Ernesto, 29:09
Episode 2 deepens the intrigue and emotional stakes of the Ana Montes story. It underscores the vulnerabilities of sprawling intelligence agencies, the psychological burden shouldered by covert operatives, and the critical importance of inter-agency vigilance. By episode’s end, U.S. counterintelligence is closing in—but Montes’ story is far from over. The drama’s momentum is tightly wound, promising even bigger revelations to come.
For listeners who missed this episode:
The narrative interlaces technical details of espionage, the emotional toll of betrayal, and the bureaucratic pitfalls of U.S. counterintelligence in a tightly scripted true story. Be prepared for a rich, tense exploration of trust, deception, patriotism, and personal cost—set against the battlefields of the Cold War's twilight years.