THE QUEEN OF CUBA, PART 2: THE KNOWN UNKNOWN

True Spies, Episode 159 - The Queen of Cuba, Part 2: The Known Unknown

NARRATOR: This is True Spies, the podcast that takes you deep inside the greatest secret missions of all time. Week by week, you’ll hear the true stories behind the operations that have shaped the world we live in. You’ll meet the people who live life undercover. What do they know? What are their skills? And what would you do in their position? I’m Sophia Di Martino and this is True Spies, from SPYSCAPE Studios.

PETER LAPP: Her career in espionage is a counterintelligence failure. You have to look at this from a failure perspective. I mean, how did someone do this for 17 years?

NARRATOR: The Queen of Cuba, Part 2: The Known Unknown. In a drab government office, scoured by the light of a halogen bulb, a stern-looking woman in her 40s sits across from two clean-cut men in suits. 

PETER LAPP: So the interview lasted about four minutes.

NARRATOR: It’s the 21st of September, 2001, and Ana Belén Montes, star analyst at the Defense Intelligence Agency, has run out of road.

PETER LAPP: And she asked us if she was under investigation. And we told her yes. 

NARRATOR: Since 1985, Ana Belén Montes has been an asset of the Cuban intelligence service - the DGI. In that time, she’s risen through the ranks to become one of the Pentagon’s most respected voices on Cuban affairs.

PETER LAPP: Once she started working at DIA, she became laser focused on building her career to the point where she could get access to as much information, having that seat at the table. 

NARRATOR: Until recently, she’s been able to pass top-secret intelligence back to Havana undetected. Her stellar reputation within the DIA has shielded her from any serious scrutiny. If you haven’t already, go back and listen to Part One of The Queen Of Cuba for the story so far. As Ana is led from the government building in cuffs, she’s probably wondering: what gave the game away after all these years? How could this happen? You might be wondering the same thing. And that’s where Pete Lapp comes in. He’s one of the men in that featureless room and he’s just closed the investigation of a lifetime. But we’re getting ahead of ourselves. Let’s start at the beginning - Pete’s beginning.

PETER LAPP: So I had the ambition to go to the FBI for about 10 years before I actually made it. It was my goal when I was in college and studied criminal justice and wanted to go to what I believe is the greatest law enforcement agency in the world, and that's the FBI. 

NARRATOR: In 1998, Pete’s dream came true. To an extent.

PETER LAPP: And given my law enforcement background, I thought the FBI would send me in its infinite wisdom to work the cool stuff - gangs and drugs and homicides, and organized crime - kicking in doors and arresting people. And I got a call from my supervisor at Quantico introducing herself, and she said, “Congratulations, you're coming to the Cuban Counterintelligence squad.” And I literally responded, “What the hell is that?” And she told me, “I can't tell you over the phone.”

NARRATOR: As he’ll be the first to admit, Pete was a little disgruntled at his first assignment. 

PETER LAPP: And then the Montes case came around and the rest is history. I had no desire to work anything else in the FBI but counterintelligence and espionage. 

NARRATOR: In the 1990s, Cuba, led by Fidel Castro, was at a vulnerable point in its history. The collapse of the communist USSR, Cuba’s main benefactor, had left the country exposed. For decades, the US had regarded the island as a hostile interloper in its backyard. Now more than ever, the Cubans needed to know what was going on behind the scenes in Washington D.C. They had stepped up their espionage efforts on American soil accordingly. But everything had not gone quite as planned.

PETER LAPP: So in South Florida in September of 1998, La Red Avispa network, the Wasp Network, was investigated and ultimately arrested by the FBI for espionage-related charges. 

NARRATOR: In the same year that Pete first donned his badge, the FBI had arrested 10 Cuban spies active in Miami, Florida. The investigation into these illegal officers, known collectively as The Wasp Network, had come about after a tip-off from three disillusioned Cuban intelligence officers all the way back to ‘94. Those same defectors also informed the US government that a Cuban spy had penetrated the Department of Defense. An UNSUB.

PETER LAPP: It's an acronym for Unknown Subject. 

NARRATOR: The Bureau mounted a parallel investigation into this mysterious foreign asset but it proved to be an arduous search.

PETER LAPP: We knew we had a penetration within the US government - that the UNSUB was either at the FBI, at the CIA, or at the Department of Defense.

NARRATOR: That’s a potential pool of 2.5m Americans.

PETER LAPP: It's an absolute needle in a haystack. And the difficulty with the original source information is the classification level was Top Secret. 

NARRATOR: The lead on the FBI’s Cuban UNSUB case was Steve McCoy, an experienced agent with almost 20 years on the job. So far, he’d come up empty. Part of Steve’s problem was that, due to the secretive nature of the case, his access to manpower was extremely limited.

PETER LAPP: We couldn't just put out an all-points bulletin and say, “Hey, the FBI's looking for a Cuban spy who blah, blah, blah, blah, blah.” We would alert the suspect before we even would identify the suspect. And therefore, Steve, and a predecessor he had, had to work very carefully and very methodically.

NARRATOR: But Steve’s fortune was about to change.

PETER LAPP: Frankly, we got very lucky when the right person heard the right information, who knew Ana. 

NARRATOR: You see, the FBI wasn’t the only organization that was clued into the existence of the UNSUB.

PETER LAPP: So we had a very loose interagency group, task force, if you will, didn't have an official name, didn't have an off-site. Three particular agencies were working on this, the FBI and two others. And information from one of those others was shared with people at DIA by Elena. 

NARRATOR: When we spoke to him, Pete wasn’t at liberty to name the other two agencies who were loosely collaborating on the case. Elena was an officer at one of these nameless agencies. It should go without saying that ‘Elena’ isn’t her real name, either. 

PETER LAPP: She's kind of a Nancy Drew-type character where she was really trying to figure out this mystery. 

NARRATOR: In the course of her agency’s investigation, Elena had come across an interesting nugget of information that significantly narrowed the field of suspects. Unfortunately, for now, exactly what that information was is classified too. All you need to know is that Elena was determined to get this evidence in front of the right people.

PETER LAPP: I understand in talking to her, she was pretty frustrated with the pace of the investigation. However, she decided to take matters into her own hands and bring in another component of the Department of Defense.

NARRATOR: That other component? The DIA, the agency where Ana Montes presided over all things Cuban.

PETER LAPP: So, Elena makes friends with DIA. 

NARRATOR: Operating without oversight from her superiors - and at great risk to her own career - Elena called a meeting with Scott Carmichael, a DIA spycatcher. If you tuned into Part One of this story, you might remember that Carmichael had a previous [relationship] with Ana Montes. In 1996, in the aftermath of Cuba’s shoot-down of two civilian planes, a fellow analyst had noticed Ana behaving strangely. Carmichael had interviewed Ana, but he’d found no evidence of anything untoward. Carmichael and a colleague looked over Elena’s evidence. Almost immediately, alarm bells began to ring.

PETER LAPP: And both of them said, “This sounds like Ana Montes and this sounds like us.” And then they did some checking. And lo and behold, it did match something that we were looking for, a tidbit, a specific tidbit.

NARRATOR: But the DIA does not have the power to arrest spies. That privilege is reserved for the FBI, working under the jurisdiction of the Department of Justice. If Carmichael wanted Ana Montes to go down, then he would have to convince Steve McCoy - the lead agent on the FBI’s UNSUB case.

PETER LAPP: So DIA came to the FBI and said, “We have a match for your UNSUB.”

NARRATOR: Finally, a lead - a single name out of a potential 2.5m. Cue slapped backs, effusive thanks, and beers all around. Right?

PETER LAPP: And the FBI basically said, “Who are you and how did you find out about our case?”

NARRATOR: There’s a reason that the agencies investigating the UNSUB were less collaborative than you might expect.

PETER LAPP: These cases are very tightly held. Need to know. 

NARRATOR: And if too many tongues began wagging...

PETER LAPP: It could have gone really bad and Montes could have found out about our investigation. 

NARRATOR: Potentially disastrous break in protocol aside, Carmichael’s information also met with a heavy dose of skepticism from the Bureau.

PETER LAPP: We thought we were looking for a man. And he brings us the name Ana Montes which is obviously a woman. 

NARRATOR: Before we chalk this up to plain old sexism, you should know that there’s a good reason for the FBI’s male focus.

PETER LAPP: The Cubans went to great lengths to disguise her gender. And they weren't putting on beards and making her look like a man. But in conversations, they were very discreet about her gender for obvious reasons. Well, maybe not so obvious. That would have allowed us to identify her more quickly and focus on just women at work for that 2.5m suspect pool. 

NARRATOR: The FBI sent Scott Carmichael on his way. But the DIA spycatcher refused to be fobbed off. In the coming weeks, he would press his case to the FBI again and again.

PETER LAPP: And from there, it took about two months at most for us to be convinced to open an investigation. When DIA came to us and said, “Here's your suspect,” they had her fitted already for an orange jumpsuit. They knew what size she would fit into. They were 100% convinced that she was the agent of a foreign power we were looking for, that she was the UNSUB. Knowing that and proving that are two entirely different things. And we had to prove that we had the right person. And by mid-October of 2000, Steve had opened a preliminary investigation on Ana Montes and she became our prime suspect.

NARRATOR: The chase was officially on.

NARRATOR: It’s the fall of 2000, and Cuban spy Ana Montes is finally on the radar of the FBI after 16 years as an active foreign agent. A preliminary investigation is put underway - and after six weeks, the Bureau is given the go-ahead to bring its full investigative powers down on her head.

PETER LAPP: With a full investigation, it allows us to use the most intrusive investigative techniques we have. We can do physical surveillance against someone that is under full investigation. And most importantly, we can ask for what's called a FISA - Foreign Intelligence Surveillance Act. It allows the FBI to conduct electronic surveillance and covert physical search authority against our subject. 

NARRATOR: But even with these resources at their disposal, catching Montes in the act is going to prove challenging. Unbeknownst to the Bureau, the treacherous analyst has changed her MO.

PETER LAPP: Her illegal officer handler, who was here in 1998, was recalled by the Cubans as a result of the arrests in Miami.

NARRATOR: Before the FBI had moved to take down the Miami Wasp Network, Ana had enjoyed semi-regular debriefs with her Cuban handler in Washington D.C. Over dinner, she passed on reams of classified intelligence that she’d read and memorized before transcribing and encrypting to disk at home. Intelligence officers in Havana would use high-frequency radio signals to contact Ana, asking for clarification or further information to the data she’d provided during these meetings. But now, she would have to change tack.

PETER LAPP: The high-frequency messages continued. But to get the intelligence back to the Cubans, Ana would go on vacation every six to eight months to a Caribbean island. And there she would meet with the Cubans on vacation and do a high-level dump of what she was able to memorize over the course of six or eight months.

NARRATOR: You might remember that Ana had trained herself to store vast amounts of information in her head. But this change of protocol meant that Ana was unable to sneak quite as much information out of the DIA as before. But this also meant that she had prioritized higher-level information. Information that could prove even more damaging to the US government.

PETER LAPP: As bright as Ana is, her memorizing that much information and then doing a ‘mind dump’ every six months, you're really only getting top-level, more strategic intelligence versus the kind of quality tactical intelligence that she could provide when you're only memorizing three things every day and coming home and writing it up.

NARRATOR: And the quality of Ana’s information was about to change for the better. In November 2000, the same month as the full investigation was opened, she was accepted as a research fellow on the National Intelligence Council - a body that draws on the whole intelligence community, and especially the CIA, to inform policy.

PETER LAPP: Had she gone to the National Intelligence Council, the NIC at the CIA, her network would have increased dramatically. It's a very prestigious position. It would have brought her inside the building of the CIA day in and day out.

NARRATOR: George Tenet, the CIA’s director at the time, was understandably adamant that Ana Montes would never set foot inside Agency headquarters. The DIA was instructed to find a way to quash Ana’s move to the NIC. 

PETER LAPP: We had to put the kibosh on that in a way that didn't cause her to be suspicious. Like, “Wait a minute, why? Why can't I go but this person can go? Are they thinking that I'm who I am? Am I committing espionage? Maybe they think that?” 

NARRATOR: Working behind the scenes, those in the know at the DIA came up with a plan. Admiral Wilson, the head of Ana’s agency, staged a very public show of frustration about the fact that his top officers were being siphoned off into other parts of the intelligence community.

PETER LAPP: Everyone's TDYs - their temporary assignments - were quashed and [that] allowed us to keep her at DIA and allow us to keep investigating her at DIA but without causing her suspicion.

NARRATOR: In one canny move, Ana Montes had been stopped in her tracks and she didn’t have the faintest idea that the Admiral’s fit of pique had been for her benefit alone. It’s now December of 2000, and the FBI’s annual Christmas party is in full swing. Rookie agent Pete Lapp is enjoying the festivities. Steve McCoy, the lead agent on the Montes case, strikes up a conversation. Pete doesn’t know that it’s about to change his life forever.

PETER LAPP: Steve and I were talking at the Christmas party and he said, “Hey, we got a name.” And we all knew about the cases because we were on the same squad. We were all in the ‘need to know’. But Steve had been working this solo for several years. 

NARRATOR: Pete’s well aware that the Montes case has been approved for a full investigation and he’s eager for a piece of the action.

PETER LAPP: The amount of work that was going to need to be done at that point, we generally would assign a second case agent, a co-case agent.

NARRATOR: Pete intends to be that second agent. But, like anyone seeking a promotion, he’ll have to sell himself.

PETER LAPP: And I said to him, “You know, the high-frequency aspect to this, I have a little bit of a background in this.” My dad begrudgingly made me get a ham radio license when I was 10 years old. This is not something most average 10-year-olds aspire to get. And I had to sit for hours and hours and hours and learn Morse code, but also learn the theory of the high frequencies, which is the part that I had a little bit of a background in. And I was able to sell him, Steve, on the fact that I had Morse code, a ham radio license, and I knew this stuff, which was a little bit of an embellishment.

NARRATOR: Well, we’ve all embellished a résumé. But Pete needn’t have worried. Steve McCoy liked the cut of his jib.

PETER LAPP: Steve and I got along pretty well on the squad already. And I said, “Can I help you with this?” And he said, “Yeah, absolutely. I'm looking for someone on the squad. And I think you and I would work really well together.”

NARRATOR: From that moment on, the two men were partners. And the net that hovered over Ana Montes could begin its inevitable descent.

PETER LAPP: We had the legal authority to follow her and do physical surveillance. So we had teams of people, we call them the G's, the surveillance specialty group. 

NARRATOR: If a member of the Surveillance Specialty Group is on your tail, chances are you won’t know about it until it’s too late.

PETER LAPP: Every FBI agent can do a little bit of surveillance work, but we're not very good at it, to be honest with you, because we don't do it every day as FBI agents. Our surveillance specialists, that's all they do. They live in their cars and they follow people around and they take notes and they're just experts in it because that's what they do.

NARRATOR: From late 2000, the G’s were all over Ana Montes.

PETER LAPP: Getting a sense of what's normal for her, her normal behavior, and then obviously trying to identify if she's meeting with a Cuban or if she's communicating and transmitting classified information, which would have been the ultimate goal of the physical surveillance and the investigation. 

NARRATOR: But in terms of actionable evidence, Ana doesn’t give much away. The FBI doesn’t know this yet, but the Cubans have pulled most of their illegals, including Ana’s handler, in the aftermath of the Wasp Network takedown.

PETER LAPP: So they identify her making these suspicious pay phone calls. And it was timed with the high-frequency messages that she was receiving that we knew were messages of content. And then after the message came through, let's say it was Tuesday night, our surveillance experts followed her on a Wednesday or a Thursday, making these odd pay phone calls, which aren't in and of themselves evidence of espionage. But there's certainly as part of the intelligence aspect to this, the methodology that we expected to see based on what we saw in Miami with La Red Avispa, the Wasp Network, and how they committed espionage and the methodology if you will. 

NARRATOR: But at this stage, that’s little more than conjecture. It’s not illegal to make phone calls from a pay phone. If Pete and Steve wanted to make their collar, they’d need to dig deeper. Time for some old-fashioned detective work.

PETER LAPP: In April of 2001, we knew from our original information that the Cubans had tasked this UNSUB to purchase a Toshiba laptop computer. We had a specific brand, make, model, and dollar amount.

NARRATOR: Those of you with memories to rival Ana Montes will remember that in the last episode, the spy purchased just such a laptop after moving to the Cuban desk of the DIA. You know that. But Pete and Steve have to prove it.

PETER LAPP: Once we identified Montes as a suspect, we were able to dig into her credit history. And lo and behold, we found through national security letters that she had taken out of a line of credit at a CompUSA. And the dollar amount was really close to what we knew the Cubans had told her that she could spend or should spend on this particular computer. 

NARRATOR: CompUSA - one of those cavernous big-box stores that went the way of the shopping mall when retail went online. But in 2001, it had tens of outlets across the country. Unwilling to be drawn into another needle-in-a-haystack scenario, Pete and Steve made an educated guess. They assumed that they could narrow their search to the D.C. area.

PETER LAPP: I identified the CompUSA, the date of the computer purchase, and Steve and I went down to this CompUSA store. And within about 25 minutes, the manager found, with us, in a shoebox of old receipts, in true name, Ana B. Montes. We found the sales slip proving her purchase of the exact brand, make and model computer.

NARRATOR: Finally - something solid. And make no mistake, the FBI needed solid.

PETER LAPP: It was huge because our FISA judge, when we sent the FISA [request] to the court for the first time, said that this was the weakest case he had ever seen. 

NARRATOR: A ‘FISA’ - that’s a warrant, basically. It stands for Foreign Intelligence Surveillance Act.

PETER LAPP: So the FBI is kind of out here saying we're not sure, DIA is here saying, “Oh, it's her and this is what size jumpsuit she's wearing, and go get her.” And then we've got this judge kind of in the middle saying this is a pretty weak case. 

NARRATOR: The judge had put pressure on Steve and Pete to come up with something like the CompUSA sales slip. Now that they had it, it was only a matter of time before Ana Montes was in their grasp.

PETER LAPP: And it was kind of our O.J. Simpson moment. You know, if the glove doesn't fit, you must acquit. The sale slip was absolute proof that Montes was the right person. And now we challenged ourselves to try and catch her in the act of committing espionage. 

NARRATOR: To that end, the FBI needed eyes on the all-important laptop. Obviously, Ana Montes wasn’t going to hand it over willingly. They would need to get inside her inner sanctum.

PETER LAPP: This is where you can be a little creative… How do we get into someone's apartment - perhaps multiple times - to conduct covert entries, to do what we need to do, these black bag jobs? 

NARRATOR: Remember, Ana can’t know that she’s under investigation. So a guns-blazing, door-smashing approach isn’t going to fly. So then - how to enter Ana’s apartment without arousing suspicion? Easy. Get someone else to let you in. Preferably somebody who knew when Ana would be out, someone in the same building.

PETER LAPP: We were able to develop a source. That individual was an absolute home run because they gave us opportunities to be in her apartment multiple, multiple times. And on that Friday, in fact, she knew that people were going to be in her apartment because there had to be a specific repair made of something to get it up to code, fire code. 

NARRATOR: That way, even if Pete’s team did leave a trace, she’d put it down to careless maintenance workers. What they found inside the apartment didn’t disappoint. 

PETER LAPP: We get into her apartment the Friday of Memorial Day weekend. Ana had traveled that weekend to visit her boyfriend down in Miami. So the house was ours, so to speak. And we conducted a covert entry and went in and found the laptop computer under her bed and made an image of that computer. And I can, with absolute sincerity, say that without that laptop computer, Ana Montes would not have done one day in jail. Ninety percent of the evidence that's in her arrest warrant came from that laptop computer under her bed that it had not been used in three years. And I don't know why it was still under her bed. If it was at the bottom of the Potomac River she would not have spent one night in jail. 

NARRATOR: So what did the investigators find that was so damning?

PETER LAPP: So we find 11 pages of what we call the “recovered text”. It's 11 pages of an undeleted narrative. I call it a diary, ‘Dear Diary’. But it's conversation, communication from the Cubans to Ana, and then from Ana to the Cubans. Now, the Cubans gave her a wipe disc and software that they wrote and created that she was supposed to apply to the computer after she read. And it was supposed to delete this information. Now, whether the software didn't work or whether she didn't use the software the correct way, I don't think we'll ever know. But the end result was it didn't work. And not everything that they wrote to her and she wrote to them was deleted.

NARRATOR: Perhaps it was carelessness, or arrogance - or both. Either way, Ana Montes had gotten sloppy. Since her in-person meetings with the Cubans in D.C. had ceased in ‘98, she had no further use for the laptop. Keeping it on her person was a fatal oversight. But then again, the last few years had been hard for Ana. After the Wasp network had gone down, she’d been keenly aware that the heat was on Cuba’s agents in the US. Later, it was revealed that she’d considered cutting contact with Havana and finally settling down with her then-boyfriend. Nonetheless, she was persuaded to stay in place. The Bureau now had grounds to convict Ana on the lesser charge of conspiracy to commit espionage. But they still wanted to catch her in the act. If possible, they wanted to take down her Cuban handler, too.

PETER LAPP: We really didn't have an idea, a firm idea, as to how she was committing espionage at that point in time. But we thought that if we could get her - capture her - meeting an illegal officer, well, then if we identified him and followed him home, perhaps he could lead us to another Ana Montes.

NARRATOR: For months, the FBI tail Ana hoping to track her to a meeting with a Cuban illegal. They don’t know that it’s a fool's errand - the man from Havana having packed up and left years earlier. In the meantime, the agents of the Wasp Network are sentenced. Hidden cameras film Ana in her apartment as she watches the news, weeping over her fellow agents. And perhaps, for herself. The Bureau delay the arrest for as long as possible but ultimately, events force their hand.

PETER LAPP: So 9/11 happens and it's a Tuesday. 

NARRATOR: The attacks on 9/11 include a strike on the Pentagon - the headquarters of the Department of Defense, under which the Defence Intelligence Agency operates. With the nation on a war footing, the DIA is about to be thrust into an intense period of activity. 

PETER LAPP: September 17, Admiral Wilson, the director of the DIA, said basically, “This is it.”

NARRATOR: Wilson needed all hands on deck. Cuba had just taken a drastic dive down the priority list.

PETER LAPP: She was going to pivot to work in the 9/11 response and Operation Enduring Freedom, and rightfully so. 

NARRATOR: Admiral Wilson was adamant that a foreign agent like Ana could not be allowed to be anywhere near the highly sensitive operations that the DIA would be undertaking in the coming weeks and months.

PETER LAPP: And he called the FBI on a Monday. And said, “You've got until Friday to arrest or I'm going to fire her because she's not going to work on anything after Friday.” 

NARRATOR: This was a harsh ultimatum. If Ana was fired, she would want to know why - her work, as always, had been impeccable. She would suspect that her time was up. If she managed to evade justice, then all of the FBI’s work would have been for nothing. But it wasn’t as simple as slapping on the cuffs. Any arrest needed to have its i’s dotted and its t’s crossed.

PETER LAPP: Steve and I still had not been allowed to talk to a local prosecutor. There were rules in place frankly, based on what the FBI did in the ‘60s with Dr. King and other folks. There were very stringent rules in place so that FBI agents working counterintelligence investigations couldn't work directly with criminal prosecutors.

NARRATOR: For a taste of the FBI operations that brought these rules about, we’d suggest listening to our episodes on COINTELPRO. In the end, the urgency of Admiral Wilson’s words worked in the FBI’s favor. 

PETER LAPP: So it helped get us permission to talk to local prosecutors, which happened by the very next day. And from Tuesday night on, Steve worked hand-in-hand with the local prosecutor to put together the affidavit that we arrested her for on that Friday. 

NARRATOR: Finally, the day came. Ana was asked to report to an office in the DIA’s headquarters to resolve an issue with her timesheet. Upon walking through the door, she came face-to-face with the men who were about to end her career as a spy. It’s a moment Pete Lapp still remembers vividly.

PETER LAPP: 9/11 had happened 10 days before. On a personal level, my son, my firstborn child, was three weeks old, so I wasn't getting a whole lot of sleep myself. Steve was exhausted. We had been working intensively for 10 months. In my career at that point in time, seven years of law enforcement, almost three at the FBI, I had never known so much about someone I was about to interview. I had been in her apartment. I had gone through her most private of spaces. We followed her around. We listened to every phone call and read every email. And that gave me a huge degree of overconfidence that she would just melt and confess to us. 

NARRATOR: But Ana was not yet out of surprises.

PETER LAPP: And in fact, the reality is that I think she was more prepared to meet us that day than we were to meet her. I think she had been thinking about the possibility that she may be arrested and meet the FBI on her - on their - terms, not hers. So I think she had been preparing [for] that day for 17 years by that point. 

NARRATOR: Stone-faced, Ana Montes meets her fate.

PETER LAPP: So the interview lasted about four minutes from the time Steve and I introduced ourselves. She sat down. We kind of did our little preamble very quickly. She knew that this was bad. And she asked us if she was under investigation. And we told her yes. And then she asked for an attorney. Steve said to her, “Well, I'm sorry to tell you, but you are under arrest for conspiracy to commit espionage.” And I told her, “Stand up”, put my handcuffs out, and arrested her. And we thought that she was going to melt. And perhaps we were a little biased because of her gender and thought that she was just going to just collapse and faint. And in fact, she was incredibly stoic and composed. And I think that I could have jumped on her back and she could have carried me out. That's the kind of strength that she had and how she was able to compose herself. 

NARRATOR: Ana’s stoic nature hadn’t won her many friends during her long career at the DIA. But now, it was the only thing keeping her going.

PETER LAPP: From the time we introduced ourselves to the time that she went off to the local D.C. jail that night - where she later told us that she lost it, she melted and sobbed - but she wasn't going to show that side to us.

NARRATOR: Over the next few months, Pete, Steve, and Ana would spend a lot of time in each other's company.

PETER LAPP: We made an agreement with her to plead guilty to a 25-year prison sentence in exchange for a full debriefing. She was debriefed by the intelligence community for a full seven months, and I had the privilege of being in that room. At first, it was like, “Oh, this is cool. This is Ana Montes. Like this is a spy, this is Fidel's top spy.” 

NARRATOR: For Pete, the novelty wore off quickly.

PETER LAPP: But she also has a certain amount of intellectual arrogance. And therefore, that did bleed through in a lot of her interactions with her colleagues over the years. Many of them respected her and thought of her as being very intelligent. And she is. However, not everyone really enjoyed working with her because she could be kind of an intellectual bully, which I personally got to see for about seven months. This is not her living her best life, shall we say. So you can understand why she would not be very pleasant to deal with. However, she portrayed intellectual arrogance a lot during our debriefings. 

NARRATOR: That’s a trait shared by almost all the high-level traitors we’ve covered on True Spies. Listen back to our episodes on Robert Hanssen, Jim Nicholson, and Aldrich Ames, and you’ll see what we mean.

PETER LAPP: In general, she was very challenging to interact with personally for me. And I think she saw me as this kind of dumb cop. Steve knew the difference between a Contra and a Sandinista. I didn't care, quite frankly. It didn't really matter to me. And I get it. I mean, this is the worst time in her life. She is betraying her friends. So this was a very difficult process for her. But she had no interest in building rapport and small talk. It was, “Turn your tape recorder on. Ask your first question.” 

NARRATOR: For all her smarts, this is where Ana Montes’ story ends. She was sentenced to 25 years for conspiracy to commit espionage. The FBI never did catch her in the act.

PETER LAPP: So her arrest was a counterintelligence success. Her career in espionage is a counterintelligence failure. How did someone do this for 17 years and was only finally caught through a lot of lucky breaks? I mean, there were people that thought that she was soft on Cuba, but then she balanced that with building such a great reputation among the intelligence community as the go-to person on Cuba for the Department of Defense. So I believe she was near-perfect. 

NARRATOR: Nearly - but not quite. Nonetheless, Ana Montes ranks highly among the intelligence community’s most damaging spies.

PETER LAPP: I would say she's the most damaging woman spy in US history. I think that Hanssen has blood on his hands and we can prove that Ames has blood on his hands. I think Montes has blood on her hands. We can't prove it.

NARRATOR: Under interrogation, Ana Montes admitted to compromising four American intelligence officers active in Cuba. Scans of her laptop revealed that she’d also compromised a multi-million dollar satellite project run by the National Reconnaissance Office, a huge blow to the organization.

PETER LAPP: This was the DIA's - probably - their biggest fear as to whether she had passed this SAP, as we call it, the Special Access Program. But it wasn't until I found what I call ‘the four sentences’ on her computer, on her laptop, that we then knew that it was part of the intelligence that she had passed to the Cubans.

NARRATOR: Ana Montes was sentenced to 25 years in a federal prison in Fort Worth, Texas. Her fellow inmates have included the wife of drug lord ‘El Chapo’ Guzman, high-profile terror suspects, and Lynette ‘Squeaky’ Fromme, formerly of the Manson Family.

PETER LAPP: In the modern era. She does rank up there with the Hanssens, the Ames’, and the Snowdens.

NARRATOR: In January 2023, Ana Belen Montes walked free after serving 21 years inside. She plans to live in Puerto Rico, where her parents were born. There’s one loose thread we haven’t quite tied up. In Part One of this story, we met Marta Velasquez, the woman who recruited Ana Montes to work for the Cubans. Both women ended up working for the US government. Marta took a role in the State Department in 1989. After Ana’s arrest, Marta made a point of never returning to the US. She’s still at large, working as an educator in Sweden, a country that does not extradite suspected spies. I’m Sophia Di Martino. You can read more about this case in Pete Lapp’s book, Queen of Cuba. Next time, we’ll meet the first of two Atomic Spies - Klaus Fuchs.