REDACTED: Declassified Mysteries with Luke Lamana - Code Name Blue Wren

Episode Date: January 7, 2025

Ana Montes was a trusted analyst at the Defense Intelligence Agency, a rising star with access to America’s most sensitive secrets. But beneath her composed exterior she lived a double life. For nearly twenty years, she betrayed her country, feeding classified intelligence to Cuba—not for money, but out of conviction. Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterFollow Redacted: Declassified Mysteries with Luke Lamana on the Wondery App or wherever you get your podcasts. You can listen to new episodes early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting https://wondery.com/links/redacted/ now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can listen to redacted, declassified mysteries early and ad free right now. Join Wondery Plus in the Wondery app or on Apple podcasts. On the morning of September 21, 2001, Ana Montes got up early and stepped into her shower. She turned on the hot water and then started using her many bars of soap, one after another, as she meticulously cleaned every inch of her body. Ana had a secret she was trying to scrub off. She stepped out of the shower and got dressed quickly. Her apartment in the upscale Washington, D.C. neighborhood of Cleveland Park was clean and

organized with not a thing out of place, or so she thought. She sped off to work in her red Toyota Echo. As she breezed along the highway, Anna steeled herself for a busy day. She worked at the Defense Intelligence Agency. Things had been hectic in the 10 days since Middle Eastern terrorists had hijacked planes and flown them into the World Trade Center and the Pentagon. Anna was the chief analyst of Cuban intelligence, but now, with the country preparing for war, it was all hands on deck, even for people like Anna,

whose jobs seemed far removed from the Middle East. Under different circumstances, Anna might have noticed there was a car tailing her. But today, she was too focused on getting to work to pay any attention. Anna arrived and settled into her desk. But just as she began work, her phone rang. It was Dave Curtin, a high-ranking intelligence official. She noticed his usual friendly tone with her had become curt and impatient, but she chalked it up to the stress of a national emergency. Curtin said there was a problem with one of her employee's

time cards, and he didn't have time to deal with it. Could she please go to the Inspector General's office and fix the problem? Anna didn't hesitate. Dealing with administrative issues was commonplace since she'd become Acting Division Chief. She marched down to the fourth floor, where a receptionist directed her to a conference room. Anna opened the door, but there was no employee having time card issues. Instead, she found two FBI agents waiting for her. Instead, she found two FBI agents waiting for her. Then, one of the agents looked directly at Anna and said, I'm sorry to tell you, but you're under arrest for conspiracy to commit espionage.

From Ballen Studios in Wondery, I'm Luke Lamanna, and this is Redacted – Declassified Mysteries, where each week we shine a light on the shadowy corners of espionage, covert operations, and misinformation to reveal the dark secrets our governments try to hide. This week's episode is called Code Name Blue Wren. The United States and Cuba have been feverishly spying on each other ever since communist revolutionary Fidel Castro overthrew a U.S.-backed dictatorship in Havana in 1959. Suddenly, America had an enemy less than 100 miles from Key West, Florida, and both sides were desperate for dirt on the other. Cuba's close ties with the Soviet Union gave American officials heartburn and brought the adversaries perilously close to nuclear war in the early 1960s.

But even when the Soviet Union collapsed and the Cold War thawed in 1989, Cuba and the United States continued to be sworn foes. Each country worked tirelessly to recruit and implant their agents at the highest levels of government, sometimes with startling results. Take Ana Montes, a most unlikely turncoat. By all accounts, she was very good at her job, which involved gathering damaging information to use against the Cuban government. At the time of her arrest, Ana was trusted with America's best-kept secrets.

Plus, she was the sister of not one, but two FBI agents, and she was related to two more, all of whom had sworn to serve this country, no matter the cost. So what drove Ana to turn on her country? How could she betray her deeply patriotic family too? And how did she get away with it for so long while working in the heart of the U.S. intelligence establishment? It was a bizarre story, a lifetime in the making, and one that raises alarming questions about America's vulnerability to traitors hiding in plain sight. Anna Montez was 15 years old the day her father moved out of the house.

It was 1972. Anna waited nervously in the bedroom she shared with her sister Lucy in the suburbs of Baltimore. Her father Alberto already had taken her three siblings, one by one, into his office. Anna, the oldest, was last. Lucy returned to their bedroom, stone-faced. Anna watched her sister carefully, but Lucy said nothing. The two of them had once been inseparable, but as they entered into young adulthood, they were growing further apart. Lucy told Anna that their father wanted to speak with her. Anna thought about hugging her sister, but she didn't know if it would be welcome,

especially now. Instead, she stood up and walked out of the room without saying a word. Anna's heart raced as she walked into her father's office. He asked her to take a seat. As she stared into his dark eyes, memories of the way he abused his family flashed through her mind. Alberto Montes had moved to the mainland United States from Puerto Rico to serve as a doctor for the U.S. Army.

After a few years, he moved his burgeoning family to Kansas to study psychotherapy at the acclaimed Meninger Psychiatric Hospital. In his time there, he researched the way that domineering parents can do lasting damage to their children. But whatever lessons Alberto learned in his research, he clearly didn't bring them home with him. His temperament was a dangerous combination of violent and unpredictable, and he lashed out at his children for any perceived slight, especially Ana.

Sitting in the same chair where Ana once feared she would suffocate, she wanted to cry. But she'd gotten enough bruises from her father's fury to know to hold back her tears. Alberto cleared his throat and calmly explained that their mother, Emilia, was divorcing him and wanted him out of the house. He asked if Anna wanted to come live with him in his new apartment. Like all of her siblings, Anna declined. As soon as Alberto left the house, it felt like Anna and her family could finally relax. Without her father looming over her,

Anna flourished. She earned a near-perfect 3.9 GPA in high school and began joining in on the marches for Hispanic Unity her mother Emilia helped organize. But all the while, she and her sister Lucy kept drifting apart. Anna harbored no resentment toward her sister, but she was determined to exercise her independence as often as possible. For instance, she would often leave their shared bedroom and sleep in the basement, where she had hung up a poster of South American revolutionary Che Guevara. She felt a sense of kinship with communist revolutionaries, people who fought back against violent repression in the way she wanted to fight back against her father.

By the time Anna graduated high school and left for the University of Virginia, her relationship with Lucy was amicable, but distant. Without their father's abuse to unite them, the Montez sisters became set on different paths in life, paths that would ultimately lead them to opposing sides of American intelligence. In the fall of 1977, Anna hurried down a street in Madrid, laughing as she ran. She called back to her friend Mimi Colon, telling her to keep up. In the months they'd spent studying abroad, Ana and Mimi had become inseparable. They were both Puerto Rican, fiercely independent and ready to change a world they saw as unjust.

Together, they had marched the streets of Madrid against U.S. support of Spanish dictator Francisco Franco's regime and discussed the negative impact of American policies on other countries. In a way, Ana felt like she'd found a new sister. The two carried bottles of wine up the stairs and knocked on the door of a small flat. Ricardo Fernando Aires opened the door and Ana threw her arms around him. She ran her fingers through his dark curls and kissed him hard. Ana and Ricardo had met on the train from Barcelona back to Madrid.

She was captivated by the Argentinian boy with sensitive eyes, who'd come to Spain to escape the authoritarian dictatorship of his home country. In Ricardo, she found both a boyfriend and a comrade. Ricardo let Ana and Mimi into his flat, where his other friends greeted them warmly. Ana poured everyone some wine and they settled into the living room, where they were harshly criticizing the United States and its government's support of violent regimes. Mimi thought her native Puerto Rico should be independent and free from the control of the American government. Even though Anna agreed with her, her feelings were more complicated.

Her parents had come from Puerto Rico, but she thought of herself as fully American, though she was embarrassed to admit it in this group. Anna's romance with Ricardo fizzled out by the end of her year in Madrid. She respected his revolutionary passion, but maintaining a long-distance relationship would have required work that neither of them was willing to put in. relationship would have required work that neither of them was willing to put in. They parted on good terms, and when she got back to the states, Ricardo continued writing to her and passing along books on Argentinian revolutionaries. Ana graduated from the University of Virginia with a degree in foreign affairs a year later, eager to forge a new path for herself.

One of her friends told her about a low-level clerical job at the Justice Department's Office of Privacy and Information Appeals in Washington, D.C. Being a clerk typist wasn't exactly an opportunity to change the world, Anna thought, but it was stable and secure and close to home in Baltimore. and close to home in Baltimore. Just four months after she started working at the Justice Department, Anna's boss called her into his office. She reassured herself that she had nothing to worry about. She'd done her best to keep her head down and do the job well.

Still, she couldn't shake the feeling that she'd done something wrong. Could they have discovered her relationship with Ricardo or the revolutionary books he'd been sending her? Anna had passed her FBI background check despite her growing contempt of the U.S. government, but she was worried they knew about her politics and had flagged her for additional review. Anna walked into the office mustering her best poker face. Her boss asked her to take a seat and she fidgeted anxiously with the hem of her skirt.

She'd only just moved into her new apartment in Northwest DC. If she got fired, she'd probably have to move back in with her mother. That's when her boss began explaining to her that she'd been granted a top-secret security clearance. Her boss acknowledged that they rarely promoted a new employee so quickly, but they were short-staffed

and needed more clerks to process Freedom of Information Act requests. Suddenly, Anna found herself reviewing some of the most sensitive national security files, determining which information could be released to the media and public. Anna relished the extra responsibility. Her attention to detail and analytical skills impressed her bosses, and she was promoted again to a legal technician.

Anna had gone from an unemployed communist sympathizer fresh out of college to the inner circle of federal government intelligence. Anna picked over her food with her fork, trying to gather her thoughts about her friend Marta's question. She'd asked Anna if she would be willing to aid Cuba in their support of the Sandinistas, the Nicaraguan revolutionaries battling the American-backed Contras in the early 1980s. Marta explained that by using Ana's access to top-secret intelligence, the Cuban government could turn the tide in Nicaragua. With her help, they could better prepare against the Contras and their ruthless tactics.

It sounded easy enough, but what Marta was asking was for Anna to commit treason, to be a spy for the Cubans. It was December 1984, five years since she began at the Department of Justice. Anna, eager to advance her career, had entered the graduate school program at the Johns Hopkins School of Advanced International Studies. As she absorbed the finer details of international relations, Anna's socialist worldview continued to crystallize. Her friendship with Marta, one of her classmates, had started innocently enough.

They shared a passion for world affairs and outrage at the U.S. government's actions in Nicaragua. Marta, who seemed almost effortlessly outgoing, got Anna to come out of her shell a bit more, to speak out for what they both believed in. What Anna didn't know was that Marta was an intelligence operative for the Cubans. Her enrollment at Johns Hopkins was a ploy to recruit students on their way to high-ranking careers in government who were disillusioned with U.S. foreign policy. Students like Anna.

Marta invited Anna on a trip to New York City to spend some time together before the holidays, cavort around Manhattan, see the sights, and discuss helping the Nicaraguans as they battled the Contras. Marta had made a reservation for three at a busy restaurant, so Anna could meet her friend. Marta introduced their dinner date as someone concerned about the plight of the Sandinistas, just like her and Ana. The three of them sat down for dinner, and it wasn't long before Marta popped the question. Ana didn't take more than a few moments before agreeing to help. In fact, she felt almost like it was her destiny to help the Sandinistas while at the same time aiding Cuba's fight against the US. same time aiding Cuba's fight against the US. Ana felt betrayed by American support for violent regimes, so betraying her country in turn felt very appropriate.

Marta congratulated her on such a monumental decision. Their dinner guest predicted Ana would be one of the best agents to ever assist Cuba. The three of them drank a toast to the future. When they got home, Marta lent Anna a typewriter, asked her to write a detailed biography for her new bosses. She reminded Anna to describe her top secret job at the Justice Department for good measure. Anna did as she was asked. Little did she know, she was typing up a list of her psychological vulnerabilities for the Cubans to use as blackmail. Shortly after Anna agreed to be a Cuban spy, she got a call from her sister Lucy. Lucy told Anna how much she inspired her.

Lucy was so proud to see her older sister dedicating her career to the Justice Department and serving her country faithfully. Lucy said she was so inspired, in fact, that she'd applied to become an agent with the FBI, and she'd just been accepted. Anna was stunned. All at once, her sister had become the enemy, an agent of the state she decided to betray just months earlier. Lucy expected her to be overjoyed, but Anna didn't take the news well.

She weakly tried to dissuade her sister before hanging up. The prospect of being a spy suddenly seemed a lot more difficult and risky. Lucy's decision to join the FBI now loomed over Anna as she prepared to take a covert trip to Cuba with Marta. They had been scheduled to participate in a two-week crash course in the art of spying, courtesy of some former Soviet agents. Pushing her fears aside, she and Marta traveled first to Spain on a fake spring break trip, where they met with a Cuban agent who gave them fake passports to get them to Havana. Once there, they learned how to receive encrypted radio messages, how to shake a tail, and how to utilize their anal sphincter muscles to control their blood pressure, a tactic for manipulating

polygraph tests. After their two weeks of spy school, Anna and Marta hopscotch back across Europe to Madrid, where they took a few tourist photos to legitimize their trip. When Anna arrived back at home, she was energized by the experience. She struggled to keep it all a secret. She really, really wanted to tell someone. She called up Mimi Colon, her old friend from her year studying in Spain. She raved to Mimi about her amazing trip to Cuba, where she got to attend all sorts of

fascinating lectures on Cuban military bases. At the time, most Americans were banned from traveling to Cuba at all, so Ana's travel stories were highly suspicious. She wasn't exactly putting what she learned in spy school into practice. It wasn't long before Ana realized it had been a mistake to tell Mimi the truth. Not long after, she stopped taking her calls and closed the door on their friendship. It wouldn't be the last time she abandoned someone she loved. Eight years later, in 1993,

Anna had more than mastered the skills the Soviet agents had taught her in Cuba, and she was doing it right under the nose of her American employers. Once a week, she left her office at the Defense Intelligence Agency, went back to her apartment, then left again, always making sure she wasn't followed. She drove to one of the nicer neighborhoods in Washington, D.C., a spot she had insisted on. Even top secret spies worry about getting mugged. Anna walked into a Chinese restaurant and took a seat at a table for two. She asked

for some water and took the liberty of ordering egg rolls, the kind her handler liked. Then she waited. About ten minutes later, her handler walked casually into the restaurant and sat down at the table. They exchanged pleasantries and spoke idly about the news. To anyone watching, they were nothing more than old friends catching up. No one seemed to notice when Anna slid a floppy disk across the table while she picked up an egg roll. By this time, Ana had established herself as the foremost analyst on Cuban intelligence

in the entire federal government. She received multiple commendations from her superiors for her work evaluating information gathered about the Cuban government and its actions. The two countries' simmering hostility didn't cool even for a moment into the 1990s, and Ana was often called into brief high-ranking officials about Cuba's strategies, politics, and most importantly, spycraft. To keep her cover airtight, Ana's work was thorough and damaging to the Cuban government. It was a compromise they were willing to make to keep one of their finest agents undetected.

Ana saw herself as the dominant voice in the agency on Cuban affairs, and she didn't take kindly when others disagreed with her analysis. If any other employees dared to have a difference of opinion, Anna would make an example of them. Half respectfully, half derisively, Anna's co-workers at the DIA called her the Queen of Cuba. To her colleagues, she was an enigma, introverted, intense, and incredibly private. They assumed whatever secrets she was keeping, she had good reason to. And they were right. While she climbed up the ladder of US intelligence, Anna fed mountains of information to the Cubans.

Three nights a week, she would turn on her shortwave radio, and receive directives from Havana. Then, Anna would meet for dinner with her handler and hand over an encrypted floppy disk containing intel and techniques the Americans were using against Cuba. She divulged details about a top secret satellite program and gave up the real identities of over 450 American operatives working in Cuba and Central America. But Ana's position had become too prominent for her to just steal documents for the Cubans and walk out with them. Ana had to spend time painstakingly developing her ability to memorize so that she could recall the contents of thousands of documents and pass them on to her handlers.

Over the years, she took two trips to Cuba for the Defense Intelligence Agency, ostensibly as fact-finding missions. During each trip, she would slip away at night to meet with important members of Cuban intelligence. Just like their American counterparts, Ana's Cuban higher-ups gave her commendations and medals for her work, some of which had caused the death or disappearance of American agents. The strain of maintaining this double life took a toll on Ana. She barely had any friends and rarely dated. The Cuban government even went so far as to set her up on a blind date with a fellow agent

to help her mood, but she didn't feel a connection. More often than not, Ana sat alone in her apartment and stood in her isolation, developing a few nervous tics along the way. But the stress was worst of all with her family. Lucy, her sister, had become something of a rising star within the FBI, carrying out national security investigations out of their Miami office no less. And she had even married one of her fellow agents. Anna could barely force a smile in the lead up to Lucy's wedding. Her sister kept asking what was wrong, but Ana couldn't tell her sister that the problem

was the growing number of FBI agents in her family. To make matters worse, Lucy encouraged their brother Tito and his wife to become FBI agents as well. By the time Ana became the queen of Cuba, four members of her family had taken oaths to uphold the Constitution as FBI agents. Every family event suddenly became a minefield for Anna. All she could do was stay quiet, just like she did at her bi-weekly Chinese dinners with her Cuban handler. On the morning of February 24, 1996, Anna's cell phone rang.

Lucy was on the other line, sounding worried. She seemed surprised to hear that Anna wasn't at the office. It was a Saturday, the only day Anna could actually relax. Why would she be at work? Lucy cleared her throat. She explained that she'd just seen on TV that the Cuban government had shot down a Brothers to the Rescue plane. Anna felt like she'd got the wind knocked out of her.

Brothers to the Rescue was a Miami-based group of Cuban expatriates who flew planes to rescue defectors and dropped anti-communist pamphlets over the island. Two of their planes had flown into Cuban airspace and Cuban authorities shot them down, killing four people. Lucy had called Anna to ask what was going to happen, but Anna could barely speak. The conflict between the two countries she served had come to a boiling point. She was going to be expected to guide the US's response to the crisis while somehow trying to help Cuba, too. Anna communicated with her bosses who asked her to come into the office early the next day.

She arrived at the DIA at 6 a.m. on Sunday, and it wasn't long before she received word that the Joint Chiefs of Staff had formed a task force. Anna was being called in. The United States hadn't used military action against Cuba since the Bay of Pigs invasion, but suddenly a show of force seemed like a certainty. Anna was meant to brief the Joint Chiefs on Cuba's military preparedness and help them evaluate the best options for retaliation. Anna crossed the Potomac and arrived at the Pentagon around 11 am. She spent the rest of the day there, filling in the Joint Chiefs and keeping tabs on new intelligence.

All day, Anna stewed in anxiety. She was trapped in the walls of the Pentagon, unable to contact her Cuban handlers and inform them of the U.S.'s counterattack plans. Around 8 p.m., Ana decided it was time to get out. She told her team that she was exhausted from the events of the day and needed to go home. But Anna's decision immediately raised eyebrows. Intelligence officials working on a Joint Chiefs Task Force are supposed to stay at their post until dismissed.

More than a few analysts were surprised, even suspicious, when the so-called Queen of Cuba left the Pentagon early amidst the most significant U.S.-Cuba conflict for over 30 years. But Anna needed to meet with her handlers. Over the next three days, Anna would continue to update them as often as she could. One Cuban agent even stopped her on the street before her morning commute, taking the massive risk of being seen out in the open together. They were deathly afraid that the United States was about to attack the island. Despite her suspicious exit, Anna did manage to influence the task force's response, arguing

strongly against taking military action. In the end, the American government strongly condemned the shoot-down and issued sanctions against Cuba, but issued no military response. Anna had served her masters in Havana well, but she had drawn unwanted attention from her colleagues. Leaving the Pentagon early that day would be the first domino that would ultimately bring her down. In 1998, while the FBI was investigating a ring of Cuban agents in Miami,

they discovered that the Cubans had placed a mole in a high-ranking position in the federal government. mole in a high-ranking position in the federal government. The FBI called the mole Agent S, but they only had limited information on the mole's identity. All they knew was that this person had met with someone with the initials WD and bought a Toshiba laptop to use for spy work. In addition, this mole had visited Guantanamo Bay, a U.S. controlled section of Cuba, in 1996. Beyond that, they had no idea who Agent S was. The FBI's investigation into Agent S stalled for two years until it finally came to the attention of Scott Carmichael,

the Defense Intelligence Agency's senior counterintelligence investigator. It was Scott's job to find enemy spies within their ranks. Scott didn't exactly fit the image of a spy hunter. People often told him he looked like the comedian Chris Farley, and because of this, most people underestimated him. But Scott was hard-nosed, ambitious, and thorough, and willing to do whatever he needed to root out moles. As he began digging into the information, Scott increasingly suspected that Agent S might be working in the Defense Intelligence Agency.

Scott reviewed the records for government officials who visited Guantanamo Bay between July 4th and July 18th, 1996, the dates the Miami evidence indicated the spy had been present. When he saw Anna Montez's name flash on his screen, a chill ran down his spine. Anna had visited Guantanamo Bay in that window exactly, and it was just five months before she left work early during the Brothers to the Rescue incident. Scott began to dig deeper. Knowing that Agent S had met someone with the initials W.D., he recalled that Anna had met her own W.D. after the brothers to the rescue planes were shot down.

When he'd interviewed her, she'd boasted about closely working with William Doherty, the chief of the FBI's counterintelligence section. The initials matched perfectly. Scott was certain Anna was the mole. He went to the FBI with his findings, but Stephen McCoy, the FBI agent in charge of the investigation, was skeptical. He told Scott he was certain the mole was a man, like approximately 95%

of spies. For the next year, Scott fought to convince McCoy that Agent S was in the other 5%. Eventually, Special Agent McCoy relented. He and his partner began investigating Anna, and it soon became clear how right Scott Carmichael had been. As they began looking into Anna's activities, they gave her the code name Blue Ren to keep her identity a secret throughout the investigation. The FBI started watching Anna's every movement, every keystroke, every call, even going through her trash, her apartment, and her pocketbook. They discovered Anna's shortwave radio, along with the unencrypted data on her computer hard drive

and a sales receipt for a Toshiba laptop, the same kind that Cuba had directed Agent S to buy. Indisputable evidence was piling up against Anna, and she had no idea she was even under investigation. Anna's niece and nephew came bounding into the guest room at her sister Lucy's house at six in the morning. It was Christmas 2000. Anna had come down to spend the holidays in Miami with Lucy, who had just split with her husband and Lucy felt it would be nice for the kids to get some extra time with their aunt. Lucy and Anna joined the kids in the living room, then watched as the kids tore open the wrapping paper on their presence with delight. Lucy leaned back on the couch, relaxed and happy,

but Anna remained tense, watching the kids like a hawk. Anna got up and began obsessively cleaning up every last shred of wrapping paper almost as soon as it hit the floor. Lucy pulled her aside, a little alarmed at her sister's sudden compulsive need to tidy up. She asked Anna to just relax and enjoy the day with them. There was no reason to be so stressed out. Lucy was wrong.

Anna had a lot to be stressed about. After the FBI took down the Miami-based group of Cuban spies called the Wasp Network, Anna's handlers went dark. She was completely out in the cold with no one to talk to. Even her one-time colleague Marta had long since cut off contact to prevent suspicion about their activities. Anna was entirely alone. Unbeknownst to Anna, the root of her troubles was sitting right next to her by the Christmas

tree. Lucy had been one of the agents in the FBI task force that took down the WASP network. Of course, Lucy had no idea she was endangering her sister's safety. How could she? Anna desperately wanted out of being a spy. She was over 40 now and she had had a long-distance boyfriend that she wanted to build a life with. She couldn't exactly intercept shortwave radio transmissions with him around, especially

since he was also a US analyst of Cuban intelligence. Her betrayals were eating away at her, making her feel like her whole life was a lie. Anna had told her handlers she was ready to retire from spying, hoping they would just thank her for her help and let her go on her way. They declined, reminding her about all of the information they had just thank her for her help and let her go on her way. They declined, reminding her about all of the information they had accumulated on her over the years. They implied that information might fall into the hands of her employer if she were to ever betray their confidence. By this point, Anna's obsessive-compulsive behaviors were getting downright scary.

Impressive compulsive behaviors were getting downright scary. She would shower for hours, meticulously cleaning herself. Boiled potatoes with no condiments became the bulk of her diet. She wore sun-protective gloves while she drove. She couldn't bear even the smallest mess. That's why she cleaned up the Christmas wrapping paper as soon as it hit the floor. Lucy was beginning to notice how much her sister was changing, and not for the better. Lucy wanted to do anything she could to help her sister. So when Anna's boyfriend called, asking Anna to spend a few days with him after Christmas,

Lucy encouraged her to join him even though it meant cutting their visit short. Anna told him she didn't want to. There was nothing Lucy could do. Anna's time as a spy had done its damage. And soon enough, it was going to come to an end. In October 2001, Lucy drove from her mother Emilia's house in Maryland, along with her mother, her brother Tito, and her sister-in-law. The mood in the car was grim, almost like they were going to a funeral, but in fact, they were heading for a federal prison.

Three weeks earlier, Lucy was working in the FBI office in Miami when her boss asked to see her. As she walked down the hallway, she assumed it had something to do with a post-9-11 threat. But then her boss began to explain that her sister, Anna, had been arrested for espionage. At first Lucy could only ask, is it true, and stare in disbelief. But she suddenly realized that she could finally understand her sister's decades of distant, sometimes hostile behavior. She cried for a minute, then stopped herself.

Her sister, Anna, was a spy. A few agents drove Lucy home, then spent a few hours interviewing her about Anna's activities. But they weren't suspicious Lucy had helped Anna, especially with how important she was to the Wasp Network investigation. Tito and his wife were interviewed as well. They were in more disbelief at first, but trusted that if the Bureau had arrested and charged Anna, they had done their due diligence. Tito was the one to call their mother and give her the news. She was inconsolable. It was almost

impossible for her to see her smart, overachieving daughter as a spy. As soon as her FBI interview was over, Lucy drove all the way from Miami to Baltimore to be with her mother. Lucy was heartbroken to see her mother so wounded. Three weeks later, the family arrived at the Central Virginia Regional Jail after a three-hour drive. They went through security and went to the visitation room, where they could only speak with Anna through a jail telephone. After a few minutes of waiting, Anna came shuffling out in a black and white striped jumpsuit. Anna gave them a slight smile as she sat down on the other side of the glass.

Lucy couldn't help but notice how relieved Anna looked, like a great weight had been lifted off of her shoulders. Emilia spoke to Anna between sobs, asking how could she have done such a thing? Tito offered angry remarks, telling Anna how badly she'd let down the family and their country. When Lucy came up to the phone, she looked her sister in the eye. Even though Anna was only a year older, she had once been like a mother to Lucy. In the midst of their father's abuse, Anna was often the one to bathe Lucy, to take her to school, and meet her teachers. Even as Anna pulled away from her, Lucy had always looked up to her sister.

There was so much she could have said. She could have cried like her mother, or been angry, like her brother. Ultimately, Lucy could only think of one thing to say. What made you think you wouldn't get caught? Anna stared back at her. After a moment, she looked away. She refused to engage with Lucy at all. to engage with Lucy at all. When Ana Montes was arrested, it barely registered in the public consciousness. In the wake of September 11th, it seemed the American people had far more to worry about than a spy feeding state secrets to Cuba.

But Ana's work was undoubtedly a threat to American lives. At least one green moray was killed in Nicaragua because of the intelligence she passed along to her Cuban handlers. And the fates of the American operatives in Cuba that Ana outed are unknown. Ultimately, Ana's actions represent a difficult quandary for the American intelligence community. Unfortunately, Anna's actions represent a difficult quandary for the American intelligence community. What to do with so-called true-believer spies? Most turncoat government analysts who spy for foreign governments do it for money. But Anna did her spying because of what she believed in.

Anna turned on her country and her family because she had absolute faith that her actions were morally right. She was never directly paid for her work, and the Cubans only gave her a few thousand dollars to settle her diploma and buy her Toshiba laptop. For counterintelligence operatives like Scott Carmichael, catching spies is an arduous business. But it's made all the more difficult when a person begins spying out of personal belief because there is no money trail to follow, and true believer spies offer fewer clues to their actions and are often more empowered to keep

their actions a secret. While Anna did a very good job of concealing her double life, Federal Intelligence officials often repeatedly cut corners or skipped precautions entirely as she climbed the ladder of the Federal Intelligence community. When Anna began working at the DIA in 1984, the Personal Security Division accepted the FBI's background check from five years earlier when she'd been hired at the Justice Department. This background check hadn't been updated and therefore overlooked her relationship with Marta, her secret trip to Cuba, and her use of drugs in graduate school.

The DIA granted Anna an interim top-secret clearance just two days after she was hired. She was never required to take a polygraph or undergo psychological testing, as she would have at the CIA or NSA. Four months after her hiring, she was granted a top-secret SCI clearance. Suddenly, she had access to sensitive compartmentalized intelligence documents concerning U.S. military operations in Nicaragua and El Salvador off the back of an inadequate background check. After the Brothers to the Rescue incident, when Anna left her shift at the Pentagon early,

some of her co-workers raised concerns about her actions. Even after she was flagged as a potential spy, ANA supervisors recommended her for the Exceptional Impact Promotion Program, where she was given GG-14 status, a coveted rank that came with a significant raise and more responsibility. The DIA, which was clearly far less rigorous in its safeguards than other intelligence agencies, finally updated its security measures after Anna's arrest to hopefully avoid similar circumstances in future. At her trial, Anna argued that the United States was too harsh toward Cuba.

She said that she hoped her actions would ultimately result in the two countries moving closer together. Anna was sentenced to a 25-year maximum security prison sentence, but she did manage to avoid the death penalty. The legacy of her father's abuse and the influence of her boyfriend and friends may have pushed Anna to become disillusioned with the United States policies. But becoming a spy was entirely a decision of her own making. If Anna really wanted to bring Cuba and the United States closer together, could she have

been more effective as a diplomat rather than a traitor to her country? The effort required to lead two lives at once nearly gave Anna a mental breakdown. She had to lie to every single person she knew for almost 20 years. To this day, her family struggles to comprehend how she could betray them so deeply. Anna was released from prison on January 6th, 2023. After that, she moved to Puerto Rico, saying she hoped to live a quiet and private life. It goes without saying that her family is barely a part of it. Follow Redacted, declassified mysteries on the Wondery app, Amazon Music, or wherever you get your podcasts.

You can listen to every episode of Redacted early and ad free right now by joining Wondery Plus in the Wondery app or on Apple podcasts. Before you go, tell us about yourself by completing a short survey at Wondery.com slash survey. From Ballin Studios and Wondery, this is Redacted, Declassified Mysteries, hosted by me, Luke Lamanna. A quick note about our stories. We do a lot of research, but some details and scenes are dramatized. We used many different sources for our show, but we especially recommend Code Name Blue

Wren, the true story of America's most dangerous female spy and the sister she betrayed by Jim Popkin and True Believer, Inside the Investigation and Capture of Anna Montes, Cuba's master spy by Scott Carmichael. This episode was written by Jake Natureman. Sound Design by Ryan Patesta. Our Producer is Christopher B. Dunn. Our Associate Producers and Researchers are Sara Vytak, Teja Palacanda and Rafa Feria. Fact Checking by Sheila Patterson.

For Ballin Studios our Head of Production is Zach Levitt. Script Editing by Scott Allen. Our Coordinating Producer is Samantha Collins. Production Support by Avery Siegel. Produced by me, Luke Lamanna. Executive Producers are Mr. Ballen and Nick Witters. For Wondery, our Head of Sound is Marcelino Villapando. Senior Producers are Loredana Palavota, Dave Schilling,

and Rachel Engelman. Senior managing producer is Nick Ryan. Managing producer is Olivia Fonte. Our executive producers are Aaron O'Flaherty and Marshall Louie. For Wondery.