The Investigation of Ana Montes: The Pentagon's Cuba Expert and Cuba's Favorite Spy

In September 2000, Chris Simmons sat down for a meeting with an intelligence officer with a secret to share.  Simmons was a counterintelligence analyst with the Defense Intelligence Agency (DIA) and a bona fide spy hunter.  The officer explained that the FBI had been investigating a Cuban spy case for two years, and she was going off the record to ask for his help to identify the spy.  Simmons was nervous.  Two years was a long time for a spy to inflict damage on US national security.1

Cuba does not present a military threat to the United States, so why would a Cuban spy be such a concern?  As the world’s biggest intelligence trafficker, Cuba sells intelligence to a long list of clients that would love to get their hands on US secrets, including Russia, China and North Korea.  Regarding their ability to steal secrets, “they outperform almost every nation in the world,” according to Simmons.  Cuba’s lack of a credible military threat allows it to lurk under the radar of US concern in a way that Russia or China can’t.

The intelligence officer informed Simmons that they were dealing with an unidentified subject, or UNSUB.  “Building an UNSUB case is like putting a puzzle together,” he said in a 2016 documentary.  “The challenge is, you don’t know what the puzzle looks like, and you don’t know how many pieces there are.”2

To help solve that puzzle, he called Scott Carmichael, a passionate DIA criminal investigator.  Carmichael accepted the case with glee.  He was the best in the business at rooting out UNSUB spies.  With the information that the officer leaked to Simmons, he was able to narrow down the list of UNSUBs to forty or fifty people.  Simmons knew the UNSUB was working in the Defense Intelligence Agency and could have had a high-level security clearance.  Carmichael was dismayed to learn that the spy must be one of his colleagues. 

The FBI’s strongest lead was that the spy traveled to the US naval station at Guantanamo Bay, Cuba at a certain time. Carmichael searched a list of a hundred people who traveled to Guantanamo Bay during the time in question.  He recoiled when he saw the twentieth name.3

“The moment I saw her name, I knew,” said Carmichael.  Ana Belen Montes was the “Queen of Cuba”, the Pentagon’s top analyst of Cuban military and political affairs.  “At that moment, I realized, I’m the only guy outside of Havana who knew that Ana Montes was a major spy.”4

Carmichael understood to what extent Montes presented a grave threat to the United States.  Her security clearance was top secret with access to special intelligence, a status afforded only to people in sensitive intelligence positions.  The biggest threat that Montes posed was that in the event of war, she could leak information about US military operations.5  As Carmichael said, “Our boys and girls in uniform, who are fighting battles for us, are gonna die because somebody stabbed them in the back.  That’s why this is not a game.  That’s what espionage is.  Death.”6

Carmichael knew Montes, but he always suspected something was off about her.  In February 1996, Montes left her post at the Pentagon when her expertise was needed in response to the Cuban military’s shootdown of two American aircraft.  Leaving her post when America’s senior military leaders needed her most raised a major red flag among other employees at the DIA.

However, Carmichael was thrown off her trail by her perfect track record.  When he reviewed the DIA files on Montes, he found a model employee who had never committed a single security violation since joining the DIA in 1985.  She began her federal career as a clerk typist in the Department of Justice and attained a top-secret security clearance just a year after starting her job.  She later grabbed a position in the DIA as a research specialist.  Over the next sixteen years, she worked her way to the top, earning praise from her supervisors and promotion after promotion, until she was nicknamed the “Queen of Cuba” for her analytical expertise of Cuban military and political affairs.7

A spy with an exemplary record just didn’t make much sense.  When Carmichael sat Montes down for an interview in November 1996, they began the meeting chatting and laughing.  But when he questioned her about her whereabouts after the shootdown incident, she grew visibly uncomfortable and evaded his questions.8

Carmichael shared his suspicions about Montes with the FBI in October 2000, a month after Simmons first called him.  The meeting was a setback.  Not only did Carmichael’s theory not stand up under scrutiny, but the FBI presented new evidence that seemed to clear Montes of guilt.  Even Carmichael had to agree that Montes seemed an unlikely suspect given her reputation and the circumstantial evidence, yet he stuck to his intuition.  As he walked out of the FBI headquarters, he angrily gazed in the direction of the DIA headquarters, just three miles away.  He was uncomfortably aware that Montes was at work that very hour, possibly committing espionage that very day.  He resolved to get her, no matter what.9

After a sleepless night, Carmichael reviewed the new evidence.  He recalled something he had learned about suspicious patterns in his 8th grade statistics class.  Remarkably, he identified such a pattern in the data that the FBI interpreted as clearing Montes from guilt.  But Carmichael knew the pattern had been manipulated by the Cubans to deflect attention from Montes’ activities.  He reported this to the FBI, and despite their earlier dismissal of his hunch, they saw that he was right.10

Now the FBI had a good case, but to prove that Ana Montes was a spy beyond a reasonable doubt, investigators would have to catch her in the act of committing espionage.  They assigned Special Agent Pete Lapp to the investigation. 

The FBI issued national security letters to gain access to Montes’ banking accounts, where investigators found that she had purchased a Toshiba laptop from a CompUSA store in Alexandria, Virginia in October 1996.  This wasn’t just any old computer.  One of the tidbits of information that the intelligence officer shared with Simmons was that the Cubans tasked the UNSUB to purchase this specific model that very month.11  Lapp rushed to CompUSA to find the sales receipt, but the store’s policy was to destroy records five years after purchase.  Against the odds, after twenty minutes of pulling out boxes in a backroom, the System Manager called out to Lapp, “Is this the one you were looking for?”12

It was.  Montes was named the prime suspect in the FBI’s UNSUB investigation.  But Lapp still needed evidence that would hold up in court.  If investigators could capture footage of Montes passing information to a Cuban contact, her conviction would be almost guaranteed.  The FBI followed her every move.  They tapped her phones and wired cameras and microphones into her office cubicle.  The surveillance team wanted to learn Montes’ patterns of behavior, to identify where and when she might be meeting her handler.  

Her Sundays were anything but typical.  She would leave her apartment in Cleveland Park at a certain time, hop on the Metro at the Friendship Heights station, get off after several stops, walk and wait for sixty seconds at some locations, ninety at others.  It was hard to figure out exactly what she was doing.13  “When her shoe seemingly came untied and she stopped and tied it, was she really tying her shoe, or was she doing counter surveillance or signaling someone?” pondered Simmons.14  Going home from work was even more interesting. Montes would veer a couple blocks off her route. She would dip into drug stores but leave without a bag. Turns out she was using the store’s pay phones, not in itself suspicious in 2001, unless you also have a cell phone, home phone, and office phone, which she certainly did.

The surveillance team took several months to present an identifiable pattern to the FBI.  They pulled records from the pay phones, revealing that Montes was calling numbers that were known to be associated with Cuban espionage.  The investigators suspected that Montes was punching in codes on the pay phones that sent signals to a Cuban pager in New York City.  That answered one big question.  Ana Montes wasn’t just a former spy; she was still spying at the time of the investigation.

Montes timed her calls to correspond with encrypted high frequency messages that were transmitted from D.C. to Cuba.  The FBI knew a little of Cuba’s espionage methods long before the UNSUB investigation.  Cuba communicated to its agents with encrypted messages that could be picked up by a shortwave radio but couldn’t be deciphered unless the agents had specific encryption and decryption disks that Cuba provided.15  The FBI knew where Montes would logically keep those disks.  Agent Lapp would have to break into her home. 

Montes lived on the second floor of a thirty-tenant apartment building at 3039 Macomb Street NW in the Cleveland Park neighborhood.  On Memorial Day weekend in 2001, Montes left D.C. to visit her boyfriend in Florida.  

23 years later, Lapp recalled that he had never been more nervous in his professional life.  The risk of Montes coming home early or a neighbor seeing something they shouldn’t was tremendous, especially when she had thirty of them.  But it took just seconds to find the Sony shortwave radio sitting in an open box below a window.  And then Lapp found the laptop under her bed.  

After finding the shortwave radio and the laptop, the FBI had good evidence.  But Lapp couldn’t find the disks in her apartment.  Without the disks, the FBI couldn’t read the encrypted messages that the Cubans sent to Montes.  If Montes didn’t keep the disks at home, where were they?  The FBI guessed she was probably carrying them around in her purse.16

One morning in August 2001, Montes left her purse in a drawer before showing up for a phony hour-long meeting.  An FBI technical team snuck into her office disguised as a maintenance crew. The team retrieved the purse and sorted through it.  The disks weren’t there, but what they found could have been even better.  Besides a wallet and cosmetics, there was a sheet of paper with a chart of codes.  Montes was punching these brevity codes into pay phones at the drug stores to communicate with that Cuban pager in New York.17

Once the FBI cracked the codes to the encrypted messages, investigators learned that Montes didn’t think she was in danger of being caught, and that she was setting up meetings with her Cuban handler once every two weeks.  The final piece of the puzzle started to come into focus.  If the FBI could capture footage of Montes meeting her spy handler, the prosecution would have its smoking gun.18

On the morning of September 11, 2001, just days away from arresting Montes, Scott Carmichael saw a billowing cloud of smoke rise from the Pentagon, just miles from an office building where he watched the news coming in from New York.  He understood, along with everyone else in the intelligence community, that a major terrorist attack was underway, and the US would have to respond.  But Carmichael also knew that the Defense Intelligence Agency would have to play a central role in that response.  In the aftermath of 9/11, all eyes turned to Afghanistan, where the Taliban harbored Osama bin Laden and al-Qaeda.  The DIA assembled a task force to assist the US Armed Forces’ impending operations in Afghanistan.  You can guess who was selected to be on that task force.

On September 22, Montes was scheduled to be briefed on Operation Enduring Freedom, the United States’ invasion of Afghanistan.  Everyone involved in the investigation understood the danger of allowing Montes to attend that briefing, especially Carmichael.  “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 that we executed during Operation Enduring Freedom would have been known to the enemy.”19  The FBI still wanted to catch Montes meeting with her spy handler to have the best chance of sending her to prison, but waiting for the right moment was too dangerous now that the United States was at war.  The time came to arrest Ana Montes.  

On September 21, one day before her scheduled briefing, Montes was called down from her office in the DIA to a conference room.  Two FBI agents greeted her.  Lapp wanted to get her to open up about her espionage to help the prosecution.  He told a convincing story about a defector from the Cuban government who warned of a spy in America’s midst.  As he told the story, he noticed a strange rash spreading across her neck.  Lapp did all he could to stop himself from pointing out the rash to the other agent in the room.  When she asked if she was under investigation, Agent Lapp told her that she was under arrest for conspiracy to commit espionage.20  He put her in handcuffs and marched her down the hall, past a vindicated Scott Carmichael.  She never looked at him.  “I doubt that she had any real idea of the role I played in her capture.”21

Her arrest came as a shock to her colleagues, but not so much to her sister Lucy.  In fact, when Lucy Montes was informed that her sister was arrested for being a Cuban spy, she felt that it actually explained a lot.  The two were never close to begin with, but Ana was especially reluctant to talk about her career with her siblings.  That’s because Ana Montes practically came from intelligence royalty.  Lucy Montes was an FBI language analyst who was hailed for cracking a Cuban spy ring that operated in Florida.  Ana and Lucy’s brother, Tito, was an FBI special agent, as were both Tito and Lucy’s spouses.  And remember the boyfriend who Ana left to visit in Florida when Agent Lapp broke into her home?  Roger Corneretto was a Pentagon official who ran a Cuban intelligence program at the military installation that the spy ring tried to infiltrate.  Despite what you may think, investigators are pretty certain that the doomed romance between Montes and Corneretto was legitimate. 

Ana completely withdrew into herself and shunned her sister precisely when Lucy made the highest achievement of her career.  Now, it all made sense.  Lucy and Tito didn’t lose their jobs like they feared and went on to lead successful lives, but their mother never recovered from the devastation of what her daughter did and where she ended up. 

In 2002, Ana Belen Montes pled guilty to conspiracy to commit espionage.  She made a plea agreement with the United States that required her to fully cooperate with law enforcement by providing information related to her espionage.  In October, she was sentenced to 25 years for espionage and agreed to be fully debriefed (interrogated) by the FBI and all other interested intelligence services of the US government.  Montes was debriefed six to seven hours a day, three days a week for several months.  She told her story all the way from her becoming a spy in 1985 to her 2001 arrest.  Montes was a spy from the very day she joined the DIA.  She sabotaged virtually all US military operations in Central America over five years in the 1980s.22  According to Chris Simmons, “We will never fully know the damage that she did to the United States.”23

Maybe, but some of that damage is known.  Carmichael blamed her for the death of a Green Beret in El Salvador in 1987 when he was gunned down by a rebel militia.  She exposed the identities of American intelligence officers working undercover in Cuba, including colleagues she personally met.  She also revealed the existence of a stealth satellite that the US used to spy on Russia, China and Iran.24

Perhaps more than anything else, one critical detail from her early life might explain why Ana Montes became a spy.  She was born on a US military base in West Germany to Alberto Montes, an Army colonel.  Alberto brutally beat his children and their mother.  Even though Emilia Montes divorced her husband and took custody of the kids when she was fifteen, the damage was done.  Ana Montes developed an anti-authoritarian grudge, especially directed at the US military culture she associated with her father.  When Montes worked in the DOJ while attending Johns Hopkins University, a friend at school heard her outspoken views against US intervention in Latin America.  She introduced her to a covert Cuban diplomat; in reality, a talent scout for Cuban spies.  Montes was the perfect fit for someone the Cuban government might convince to become their agent.  She never even accepted payment for her espionage.25

When Ana Belen Montes was released from prison in January 2023, she immediately spoke out against the US economic embargo on Cuba.  She now lives off the radar in Puerto Rico, and remains defiant that what she did was right.  She leaves a legacy as one of the most dangerous spies in American history.26