tv Declassified CNN August 13, 2016 9:00pm-10:01pm PDT
because of the trigon operation, i continued to work very successfully for 32 years as a covert cia officer. -- captions by vitac -- www.vitac.com as a former fbi agent and chairman of the house intelligence committee, i had oversight of all 16 of our nation's intelligence agencies. my name is mike rogers. i had access to classified information gathered by our operatives. people who risked everything for the united states and our families. you don't know their faces or their names. you don't know the real stories from the people who lived the fear and the pressure, until now. there was a cuban agent with access to classified information, placing our entire nation's future at risk. >> the spy was almost certainly in our building. >> i think it's the betrayal that gets me.
almost every nation in the world spies. most nations in the world spy against the united states. we are the number one target. there are at least 70, give or take 10, nations spying on the u.s. if you were to believe there are probably in excess of 100,000 foreign agents working in this country, that's not paranoia. that's a good guess. my name is chris simmons. i was a career intelligence officer with the defense intelligence agency where i headed counterintelligence analysis for the america's team. the defense intelligence agency is the pentagon's intelligence apparatus. dia's focus on the national security structure of every nation in the world.
the way we became engaged with this case, a woman who led part of the fbi investigation, took the initiative to set up the meeting. the fbi explained we've heard you and your team are the best there are on cuban intelligence, and we are part of an fbi spy case that involved cuba, which had been dragging on for three years. we're frustrated. can you help us? i was so concerned about the damage that this mole could have already inflicted and would continue to inflict that i immediately called scott carmichael. scott carmichael was head of our investigations side. >> i loved being a spy hunter. i love the chase. nothing would make me happier than for somebody to say, well, scott, we know espionage is occurring. we've got these few tidbits of information. can you help us out? you bet. i especially love what i term unsub investigations, unknown subject investigations. and those are investigations where you have good reason to believe that espionage is occurring. you have absolutely no idea who
might be doing it. fbi was trying to identify a cuban spy who was possibly in the d.c. area, and they knew a few tidbits of information about the spy. but they had no idea who this person was, where this person worked. well, that's the problem. what they were talking about is a possibility that there was a cuban agent with access to classified information. cuba does not pose a credible military threat to the united states. the real danger of cuban intelligence operations is that the intelligence take is shared by cuba with other countries. he shares information with iran, china, russia, even venezuela, north korea. >> what makes cuba important is that it's the world's biggest intelligence trafficker. and i say that in the context of the sale or barter of u.s.
secrets is now one of the central engines of the cuban economy. whether that's political secrets, economic secrets, military secrets, every country has interest in the united states. and cuba, their ability to steal secrets, they outperform almost every nation in the world. the cubans are so good for several reasons. at the start of the cold war, the russians and all the warsaw pact allies saw the cubans as useful partners that would not draw attention like they would. the russians, the poles, every service in the world trained the cubans. cuba exploited the perception that they're not a threat because it lowers their cost of espionage, and it gets them more clients because situations that would be hard for the chinese or russians to do, cuban agents can do easily.
building an unsub case is like putting a puzzle together. the challenge is you don't know what the puzzle looks like and you don't know how many pieces there are. the fbi's case, they had three very distinct pieces of the puzzle as they share their puzzle pieces. it turns out, i had the fourth puzzle piece. that one piece of information fit perfectly into what they had just shared, and when we put it all together, i told them that the fbi is looking in the wrong place. because the unsub doing the three things you just shared, coupled with the fourth piece of the puzzle, there are probably 40 or 50 people that could do what your unsub can do. and in all likelihood is working within the confines of the defense intelligence agency. even more narrowly, the spy was
almost certainly in our building. >> what was the information that the fbi had? what did it show you? >> the information that our colleagues shared with us remains classified to this day because it would reveal some of our methods that the cubans aren't yet aware of. >> some of the methods and systems that the dia employs to collect information about other countries' activities are so sophisticated, and that's why espionage is so dangerous. because if you tell other countries, hey, the united states is able to do this, they will then guard against that. and, of course, that degrades our ability to collect information that our war fighters need in the event they
go to war with some country. that's the problem. for most of the years that i worked for dia, i was a senior counterintelligence investigator. so if anybody was engaging in espionage in the agency, on my watch, that was an affront to me. i hate that. i think it's the betrayal that gets me. like, how dare you. one investigative lead that the fbi had was that the spy in question had traveled to the naval station at guantanamo, cuba. during a specific time frame. that was the best investigative lead. i knew people that travel to gitmo require permission to do so. and they submit the request for information by message. and it's searchable by keyword. it only took me moments to submit my query. and the system produced a hit file. a list of messages, about 100 of them, that matched parameters of my search. so i started hitting my function
key very quickly just to see if i would recognize names. and the 20th one -- it was very, very emotional. the moment i saw her name, i knew. and nothing is more effective at relieving your sneezing, runny nose and nasal congestion. return to the world. try clarispray today. (vo) nutritional needs...og's all in one. purina one. healthy energy, all in one. strong muscles, all in one. highly digestible, and a taste he loves, all in one.
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the second i saw her name, ana montes, i said, oh -- i knew that ana at that time was the queen of cuba. she was the senior cuba analyst in the entire intelligence community. ana montes had probably more time invested in the study of political military affairs regarding cuba than anybody else. security clearance was top secret with access to special intelligence. this stuff is so extraordinarily sensitive that only a handful of people would be given access to it. someone in ana's position could cause exceptionally grave damage to our collective security, and she could do that in a moment, which means a greater possibility that our war fighters, who are our boys and girls, will die. that's why this is not a game. i actually went into shock.
and at that moment, i realized i'm the only guy outside of havana who knew that ana montes was a major spy. now, this was not the first time i'd seen ana montes' name. i had other interactions with ana. and during the course of those interactions with her, i developed a gut feeling that there was something wrong and suspicious about this woman. and so when i saw her name again, i knew that she was the spy that they were looking for. >> four years earlier, in april of 1996, one of our employees, rich brown, came to me expressing concerns about ana. he said her actions during a specific incident caused me great concern. >> 3, 2, 1. >> okay. >> ladies and gentlemen, i've
just been briefed by the national security adviser on the shooting down today of two american civilian airplanes by cuban military aircraft. >> on the 24th of february, 1996, the cuban military shot down two aircraft operated by a cuban immigrant group called brothers to the rescue. two civilian aircraft piloted by a total of three american citizens were shot down in international air space by cuban migs. >> do you have relatives? >> my son. our son was in one of the airplanes. >> that was the murder of three american citizens. now in response to the shoot-down, the united states government scrambled to figure out what had happened and how we might respond. one of the first people that the pentagon called in as an expert
to advise was ana montes. >> in that circumstance, when the pentagon calls you in, you must stay in place until you're dismissed. doesn't matter how long. if you're in there for two months, you stay there until our senior military leaders no longer have a need for your expertise. rich brown called the pentagon shortly after 8:00 p.m. that night just to ask ana a question, but she left. and he thought, well, that's odd. rich thought that her actions in leaving the pentagon early was suspicious. so the first thing i did was take a look at our own records. everybody at dia has a personnel file. everybody has a security file. i reviewed our files on ana montes, and what i found was an absolutely model employee. ana had been working at dia since 1985, and she'd never committed a security violation.
she rose through the ranks. lived modestly. the kind of employee that supervisors hold up for others to emulate. so, the assessment that ana might be a spy just didn't make a lot of sense. nevertheless, i decided to interview her. and ana gave me great answers to most of my questions. but then when i started questioning her about just going home and did anybody see you, her entire demeanor changed. one minute we're joking and laughing, having a good time, and the next minute, she is scared to death that i know something that she did. and i had no idea what it was. i didn't know what was going on. but i walked away from that situation with a gut feeling that she was hiding something from me that was very important to her. and that gut feeling played a
major role four years later. in september of 2000 when her name popped up on that screen. and so i contacted the fbi. i met with them. i told them, look. i've got an employee who i think is your suspect. the fbi had yet additional data that they were employing to measure suspects. new information which i had not previously possessed. and i refer to it as a template. ana montes did not match up against that template at all. the fbi told me that, well, on the basis of this information alone, i can eliminate your employee as a suspect in this case. and they, obviously, had a lot of confidence in the validity of this new information. they used it as a trump card on me. from the time i left the meeting until the time i took the elevator ride downstairs and i found myself literally out on the curb, i knew that ana was at work three miles south in our
headquarters building. i could just picture her in my mind's eye. that woman who is in my building pulling this crap on my watch, placing our entire nation's future at risk. she was going to get the hell out of there. now i needed the fbi to help make that happen. i said we're going to persuade the fbi that ana montes was the spy that they were looking for. and i realized i had to attack the trump card. if you have a typical airline credit card, you only earn double miles when you buy stuff from that airline. wait...is this where you typically shop? you should be getting double miles on every purchase! switch...to the capital one venture card. with venture, you earn unlimited double miles on every purchase, everywhere, every day. not just ...(dismissively) airline purchases. seriously... double miles... everywhere.
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the next morning on a saturday, the 14th of october of 2000, i got up. i couldn't sleep very well. i was so upset about the trump card because what i knew about ana did not match up against that new information at all. but i knew that she was the agent they were looking for. it was her. i never doubted my intuition. the next day, i spent most of the day examining the trump card, and i discovered something. i discovered a pattern that i recognized from something that i learned in an eighth grade
statistics math class. and my math instructor told us, if you ever see this pattern, you need to understand that the fix is in. somebody is manipulating the data in order to get the outcome that you're looking at. and i saw a pattern which i knew could never occur in a random world. can't happen. it had to be the cubans. the fbi was using the trump card that was being manipulated. they didn't know it. and so at that moment, i realized that i had cracked the trump card. i wrote up an eight-page memo, and the next morning, i faxed that eight-page memo to the fbi. about an hour later, the fbi case agent steve mccoy called me. and the first thing he said was, scott, i think we've gotten off on the wrong foot.
i think we're going to be working together for a while. i was relieved. the only way we were going to be successful is to work together. and it was at that moment, i knew we were going to be okay. one of the things that the fbi did was to assign a co-case agent by the name of pete lapp. >> so the first time i heard the name ana montes was at our christmas party in 2000. i knew the fbi had gotten the name of a suspect, someone who may have matched one of these unsub cases as we call them. i talked to steve mccoy the senior case agent and said, hey, i hear you're working this case. you have a name. i'd love to work with you on this. so he said, yeah, sure. i'd really appreciate your help. and from there, we worked the entire case together with scott. it's important to keep in mind
the fbi has to prove these cases. we're the lead counterintelligence agency for the united states. the bureau is going to be the organization that brings charges against someone for espionage. there's a lot of pressure on us to get it right. knowing someone is guilty of espionage is fundamentally different than proving that someone is guilty of espionage. so let's validate scott's claim that she's an agent of a foreign power. in fact, who we're looking for. and then let's try to catch her in the act of committing espionage. national security letters are hugely important tools for the fbi. so a national security letter is a letter that's issued by the fbi that compels financial institutions, credit institutions, telephone companies to relinquish critical information. and once montes is identified as a suspect, we opened a full investigation on her. it allowed us to use national security limits.
we had very sensitive intelligence that told us that the unknown subject had purchased a specific brand, make and model computer at a specific period of time in 1996 from a store in alexandria. no further information. through national security letters, i identified ana's line of credit. and from that, we knew that ana had made a purchase at comp usa back in october of 1996. in april 2001, we served a national security letter at comp usa and asked them, could we identify a specific purchase made here in october of 1996? and they said we keep records that far back behind the store and we only keep them for about five years. this was april 2001. the records were almost destroyed. so we pulled out boxes. and about 20 minutes after we started, the assistant manager for comp usa said, is this what you're looking for?
and, in fact, it was the purchase that ana made in her name for the computer that we could prove the cubans tasked her to purchase back in october of 1996. the sales receipt for this computer purchase proved that she was, in fact, the spy. so from april of 2001, i had no doubts that she was a cuban spy. the question was, was she currently spying, and could we catch her in the act of committing espionage?
the sales receipt for this computer purchase proved that she was, in fact, the spy. ana montes officially became the prime suspect of the unknown subject investigation. now it was just a matter of proving her, catching her in the act of committing espionage. >> we needed to get her on film meeting someone, uploading intelligence secrets, passing an encrypted thumb drive. that's the ultimate threshold. court-worthy evidence that will convict a spy. >> so one of the first things we did was request physical surveillance resources on her. >> we had a lot to do. the fbi put cameras in her cubicle and microphones and tap her phones and all that sort of
thing. >> we started doing significant physical surveillance on montes, identifying her patterns of behavior. what was her routine. >> in watching ana montes, we saw that, for example, she'd leave her home on sundays at a precise time, go to the local metro, get on, go several stops, get off, walk, stop at locations, wait 60 seconds, go somewhere else, wait 90 seconds. very methodical. things a normal person doesn't. so from a trade craft standpoint, you knew something was afoot. her shoe seemingly came untied and she stopped to tie it. was she really tying her shoe or doing countersurveillance or signaling someone? over the next several months, the surveillance team told us we have a pattern now. she's leaving work at particular times, following a route. here's the route. she's going into drug stores, but she doesn't come out with a
bag. so what is she doing in the stores? turns out she was using the pay phones. >> not too long ago we had pay phones everywhere. and using pay phones was not in and of itself suspicious, but when you have a cell phone, a home phone and phones at your office, the fact that you go a couple of blocks off your normal route to and from home to use a pay phone, that is suspicious. >> once we did the legal paperwork to get the records from the pay phone and we saw that she was calling pagers in new york city. and those particular numbers we knew were associated with cuban espionage. and our suspicions were that she was punching in codes, three or four digits. we knew she was communicating with a pager, sending signals. that told us she was still active.
>> so we saw her making all these pay phone calls. the timing of which corresponded with encrypted high-frequency messages being transmitted to the d.c. area from cuba. even before montes was identified as a suspect, we knew the cubans were communicating to their agents via high frequency messages that would have been picked up using a short wave radio. >> the cubans would send a message on a tuesday. repeat it again twice on thursday. twice on saturday. we knew that communicating to the cubans via the high frequency messages required encryption and decryption disks. it's not like they were sending the messages out in the open air. they were encrypted messages that no one else could read unless you had the matching
decryption software that the cubans gave to their agents. in order to catch her in the act, we knew we needed to get into her home. because we knew we were trying to find these disks. she lived in a 30-tenant ownership building. so a huge challenge to try to get into her apartment without getting detected. our surveillance of her taught us that she had a boyfriend, and her boyfriend lived out of town in florida. and her traveling to visit her boyfriend memorial day weekend 2001 gave us a long opportunity to get into her apartment covertly to do a physical search. so when we went into her apartment, i was absolutely nervous. it was hot. there was no air conditioning, and although it was a small two-bedroom apartment, there was a lot to look through. the risk of getting caught doing this is tremendous.
and that's the last thing you want to do is compromise the investigation by someone coming home too early or someone, you know, watering the plants when you didn't plan on them doing that. we started searching her apartment. and first thing we found was the sony short wave radio in its box out in the open underneath an open window. and then we found the toshiba laptop computer that the cubans had tasked her to purchase. so our computer experts made a copy of the computer hard drive so that we could forensically analyze it and see what was on it. so ana montes, as she had received and sent reports out to the cubans had tried to delete what was on her computer. but in the deleted space of her computer, we found almost 11
pages of single spaced text in english and spanish. and in that text, we found national defense information that montes gave to the cubans that was classified. that was a hugely successful covert search. but we had not found the disks. if we could find the disks the cubans had given her, we'd be able to read her encrypted messages while she was getting them and hopefully then know what the messages were between her and the cubans. i asked my dentist if an electric toothbrush was going to clean better than a manual. he said sure...but don't get just any one. get one inspired by dentists, with a round brush head. go pro with oral-b. oral-b's rounded brush head cups your teeth to break up plaque and rotates to sweep it away. and oral-b delivers a clinically proven superior clean versus sonicare diamondclean. my mouth feels super clean! oral-b. know you're getting a superior clean. i'm never going back to a manual brush.
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we had made a copy and found the communication between her and the cubans on the computer. we found the short wave radio. we saw her making all these pay phone calls. and we knew we had a strong case, but we felt we had to find these disks. we really needed that concrete proof that took away any shadow of a doubt from anybody that montes is guilty of espionage. >> the fbi speculated that perhaps she was keeping this data on her person. the reason they couldn't find it is because she was carrying it around with her all the time,
perhaps in her purse. the objective was to get to her purse, search it and get that purse back without either ana or any of her co-workers having even a suspicion that anything had occurred. >> we came up with a plan to separate her from the purse. we had insider access to ana montes' daily life. what occurred to us is, we could create a fake meeting that she would have to attend. >> we gave her a major speaking assignment, which meant she'd be visible to everybody, and psychologically, it just wouldn't look good for her to have a purse sitting on top of her materials. we scheduled that briefing for 9:00 in the morning because we wanted to make sure ana had time to settle in at work by 8:00 to put her purse into a drawer so she'd just secure it. and she did. >> all the attendees were at the
meeting prepared to do a good hour, hour and a half discussion of this very important issue. once the door was closed, the fbi technical team, under the guise of being a maintenance crew, went into her cubicle and the surrounding area to do routine maintenance on the facilities and had access to her purse. >> so while she was at the meeting, we had a very short period of time to go through her purse looking for the disks. >> it was a typical woman's purse. had cosmetics and wallets and just had a lot of purse type stuff in there. so we looked and searched in and couldn't find the disks there. >> so we couldn't find exactly what we were looking for, but we did find something. inside ana's purse, the fbi
found a sheet with a matrix, which was crypto material which ana employed when she communicated with the cubans via pagers. that's what we were looking for to determine what the message was between her and cuban intelligence. >> once we had her brevity codes, it was simply a matter of going to a phone, punching in the exact same codes, and we'd match it against the messages that had been sent and would be sent in the future and know exactly what she was telling new york. it told us at the time that she did not perceive herself in danger and was setting up a future meeting to meet with her case handler or spy handler, which was every other week. if we could get her meeting with her spy handler, we knew we'd get her convicted and put her in prison. she had the potential to be one of america's most dangerous spies. >> [ bleep ].
[ sirens ] >> i was sitting in my boss' office, i think, in a commercial office building in northern virginia about a mile from the pentagon when 9/11 occurred. >> oh, my god! >> and we were riveted to the television screen. we understood this was a terrorist attack and that it was significant. i sat in there for another 20 minutes or so, and i saw a puff of smoke to my right. and the puff of smoke persisted and turned gray and began to billow, and then news coverage came out about an aircraft hitting the pentagon. i didn't see the impact but knew what was happening. we had just crossed a threshold. the united states of america was going to formulate some sort of
a response that would require the assistance and support of the defense intelligence agency. >> in the aftermath of 9/11, dia assembled a task force to support the pentagon's forthcoming operations in afghanistan. ana montes was among those to be chosen for the task force. >> on saturday the 22nd of september, ana was going to be briefed on the war plan for "operation enduring freedom," the effort to remove the taliban from afghanistan. if ana montes gained access to information about our war plans, she could give it to the cubans who, in turn, would be happy to trade that information or to simply share that information with our adversaries, possibly including the taliban. in that event, all of our plans we executed during "operation enduring freedom" would have been known to the enemy. i knew that our investigation with ana was coming to an end.
>> we really wanted to catch her in the act of committing espionage with her handler who was handling and receiving the classified information. but we knew that it was just too much risk and potential damage to keep her at dia at such a sensitive time when we were launching a war. it was time to arrest montes for conspiracy to commit espionage. (vo) maybe it was here, when you hit 300,000 miles. or here, when you walked away without a scratch. maybe it was the day you realized your baby was not a baby anymore. every subaru is built to earn your trust. because we know what you're trusting us with. subaru. kelley blue book's most trusted brand. and best overall brand. (avo) love. it's what makes a subaru, a subaru. get zero percent on select subaru models during the subaru a lot to love event, now through august thirty-first. this car is traveling over 200 miles per hour.
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when 9/11 happened, we knew we had days left in the investigation. >> we really wanted to catch her in the act of committing espionage, but it was just too much risk to keep her at dia at such a sensitive time when we were launching a war. it was time to arrest montes for conspiracy to commit espionage. >> the fbi decided they'd like to effect the arrest over in our building. we decided to bring her down into the offices of the inspector general. >> so, we were going to arrest her at work, but we still wanted to try and get her to make some incriminating statements. if we could get her to say things about her espionage in an interview before she's arrested,
that would be a good thing for the prosecution. >> we started our interview. talked to her about this scenario that wasn't true, that there was a defector that came out from the cuban intelligence service and he talked about a penetration of the u.s. government. and quickly into this pretext, ana had this interesting physiological reaction. there was a rash that immediately broke out. they were on the side of her neck facing me. i could only see them. i had to kind of control myself and not go, look at that. she has this rash breaking out. so, she got them under control, and she was very focused and very firm. getting through this story, montes wised up to it and asked if she was under investigation. and at that point in time, we
told her she was under arrest for conspiracy to commit espionage, handcuffed her, and her life changed from that moment on. >> pete came out of the conference room with ana. she was in handcuffs, and i saw them walking down the corridor, if you will, towards me. she was almost standing in front of me, and she never looked at me. i doubt that she had any real idea as to what role i might have played in her capture. >> we're pleased to announce this morning that 45-year-old ana belen montes pled guilty, charged with espionage. it is a result between miss montes and the united states that will require her to fully cooperate with law enforcement by providing information
relating to all criminal and/or intelligence activities of which she has knowledge. >> as part of the plea agreement, she got 25 years for espionage. and in exchange for that, she agreed to be fully debriefed by the fbi and the rest of the intelligence community. she was debriefed for about seven months, exhaustively, probably three times a week, five or six hours a day. >> during ana's debriefing, they took her from the earliest days in 1985, when she started, all the way up to the day of arrest. >> what did you learn? >> she betrayed us in el salvador, compromised all of our military operations in central america throughout five years of the secret war during the 1980s. >> and to think, here was a woman that would literally sit across the table from special forces teams going down range and pretend to be their friend,
and then as soon as the meeting is over, contact her cuban handlers and say, you have another special forces team going on to el salvador. they'll be at this location on these dates. good luck. happy hunting. i'm convinced she willfully and intentionally took every action she could to kill americans in combat. it should make us all enraged. >> people from the intelligence community, every individual that she met from the u.s. government, if they were going to cuban covertly, she identified who they were and what their true mission was versus what their stated mission was. >> a lot of the information she shared will remain classified to the american public. isn't that ironic that information that you cannot read was read in beijing, moscow, tehran, cuba. there is no way, even in six months of daily, all-day interrogations, you're not going
to get everything that a career spy did in 16 years. we will never fully know the damage that she did to the united states. during the time we were debriefing her, we learned a lot about her motivation for being a cuban spy. >> so, in 1984, 1985, montes was working on her masters degree in international relations at johns hopkins university, and her mutual friend saw her in class, knew her opinions, and knew that she was diametrically opposed to u.s. foreign policy and what we were doing in that time period which was 1984, 1985. ana felt that the united states did not have a right to impose their will on other countries, especially in central and south america, and really disagreed with u.s. foreign policy at the time. her friend sensed that she had this passion that the cubans would be interested in.
she was introduced to the cubans via a diplomat, their undercover. he recognized she had a visceral empathy for the cuban plight for the cuban cause. and that's folks who they really reach out to and ultimately trust to be their agents. >> ana's cubicle was devoid of anything personal. it was all devoted to business. but ana's cubicle wall posted next to her computer monitor was a piece of paper, that was lined and written in script, the king hath note of all they attempt, by interceptions which they dream not of. >> fidel castro is aware of all of their plans by some secret means they can't even imagine. this was an inspirational quote she posted to her wall so that every time she saw it, she could see it and motivate herself as a
spy. you know, people commit espionage are a place in our collected security at risk. our boys and girls in uniform who are fighting battles for us are going to die because somebody stabbed them in the back. that's what espionage is, death. and that's why guys like me work so hard to find these people. i have told people that hunting for spies is like trying to find a ghost in the fog. and you've got to believe, first of all, that they're there. and then you have to have enough drive to keep looking. -- captions by vitac -- www.vitac.com
this is cnn breaking news. hello, everyone, i'm zane asher. this is cnn news now. we begin with breaking news. violence has erupted in the u.s. city of milwaukee, wisconsin, after police shot and killed a man they were in pursuit of. crowds filled the streets, but the situation did get out of control within the last two hours. police are calling this a disturbance. police say an officer was injured after someone threw a brick through the window of his police car. protesters also set a gas station on fire.