Cold War Cuban Spies in the USA in the 1980s – The Case of Ana Montes

From the 1980s American Ana Montes supplied the Communist Cuban government with very valuable information. During the 1980s she helped Cuba support communist insurgencies in El Salvador and Nicaragua, and she continued to help Fidel Castro’s Cuba even after the end of the Cold War. Scott Rose explains.

You can read past articles in the series about spies who shared American atomic secrets with the Soviet Union (read more here), the 1950s “Red Scare” (read more here), and the American who supplied the Soviets with secrets in the 1980s (read more here).

The mugshot of Ana Montes after her arrest.

Throughout the Cold War and in the years afterward, the United States has had to combat spies who were either giving or selling information to America’s enemies. The majority of the cases involved individuals who were aiding the Soviet Union, as the Soviets had a powerful and proven espionage network around the world. Most observers probably wouldn’t think of the small Caribbean nation of Cuba as a country capable of carrying out successful spying operations against the U.S. However, the Cuban intelligence services were vastly underestimated, and they were able to acquire top-secret information from an American mole named Ana Montes for nearly two decades. 

The Makings of a Spy

Ana Montes was one of four children born to U.S. Army doctor Alberto Montes and his wife, Emilia. The family moved several times during Ana’s early years before settling in Maryland, where Alberto became a well-regarded psychiatrist. While Dr. Montes undoubtedly helped many people, he was at times cruel to his children, losing his temper and beating them with a belt. This abuse had emotional effects on Ana, as she became distant and aloof at a young age. Years later, her sister, who was only a year older, would remark that she never really knew or felt very close to Ana. One of the effects of having an authoritarian father was that she seemed to gravitate toward those who were less powerful, or “underdogs.” The parents would divorce while Ana was in her teens.

In spite of her turbulent home life, Montes was an excellent student. During her high school years, she was viewed by her peers as extremely intelligent and perpetually serious, but this paid off as she graduated near the top of her class, with a 3.9 grade point average. She would move on to the University of Virginia, where her academic success continued. While at Virginia, she got to participate in a study-abroad program in Spain for a year.

It was during her time in Spain that Montes began to harbor anti-U.S. sentiments. She began a relationship with a fellow student in Spain, a young Marxist from Argentina. This was her first real boyfriend, and to a certain extent, she fell under his leftist spell. He often told her of American support for authoritarian governments in Latin America, such as those of Somoza in Nicaragua and Pinochet in Chile. Together they attended anti-American rallies, and in time she came to genuinely buy into her boyfriend’s theories and adopt them as her own. Eventually she returned to Virginia, earning a degree in foreign affairs in 1979.

Montes’ brother and older sister both worked for the FBI, and after graduating, she took a job as a typist at the Department of Justice. At night, she attended graduate school at Johns Hopkins University, and eventually she obtained her masters’ degree in Advanced Foreign Studies. During her time at Johns Hopkins, one of the main topics of discussion was the civil war in Nicaragua. Montes detested the fact the United States was sending aid to the Contra forces that were fighting against Nicaragua’s socialist Sandinista government. She performed well at the Department of Justice, and in 1984 she received a high-level security clearance, passing an FBI background check in the process.

While at Johns Hopkins, Cuban intelligence services identified Ana Montes as a potential spy. A former Cuban agent later stated that the Cubans have often looked to find American students with strong political leanings who appear destined for government jobs. Reportedly, one of Montes’ schoolmates at Hopkins was already in contact with the Cubans, and set up a dialogue with Ana. At first, Montes was asked to help the Cubans with small tasks, such as translations. However, the Cubans knew the passion Montes had for the Sandinistas, and when they asked her for American information about Nicaragua, they had pressed the right button. She dove in headfirst, and by the end of 1984, she had become a major Cuban asset.

No Turning Back

In early 1985, Montes made a secret trip to Cuba to receive intelligence training, and disguised herself by wearing a wig. The Cubans knew that they had an agent with star potential in Montes, and they went out of their way to make sure she got a favorable impression of Cuba and its government while she was there. They even introduced her to a young Cuban gentleman who showed her around the country’s cities, beaches, and countryside. During her training in Cuba she learned how to decipher coding and make information drops. They taught her how to pass a lie detector test if she came under any suspicion.

Ana’s Cuban handlers urged her to begin applying for government jobs that would give her more access to the most highly sensitive American intelligence. Not long after returning to Washington, she was hired by the Defense Intelligence Agency, and the Cubans could not have been much happier. Other than the CIA, the Defense Intelligence Agency (DIA) handles more classified data on foreign governments than any other sector of the American government. The DIA analyzes intelligence and informs American leaders, all the way up to the President, of the military capabilities and intentions of foreign governments, and most of the information is acquired from human spies. From the beginning of her time at the DIA, Montes misled her superiors and much of the government by making Cuban espionage threats seem minimal when they were actually very serious. She also downplayed Cuba’s role in the civil wars taking place in Nicaragua and El Salvador. In truth, the Cubans had thousands of military advisors on the ground in both countries.

Montes seemed to be the perfect employee, for both the United States and Cuba. At her DIA job, she displayed a steely efficiency, and was known for being unapproachable by her co-workers. The intelligence community tends to be very tight, but Montes remained a virtual loner while her superiors recognized her obvious intelligence. She could turn on the charm, but only when it was helpful for serving her purposes. At night, she worked at her other job, as a Cuban spy. Using a radio, she received numeric messages from Cuban intelligence, which she then decoded with Cuban decryption software on her personal computer. She sent information back in the same way, but Montes was too smart to bring classified papers home from the DIA. Instead, she was actually able to memorize the content of highly sensitive documents at work before translating it into numeric codes for the Cubans. Sometimes she would pass information to Cuban agents at crowded restaurants in Washington. All the while, the DIA considered Montes to be the ideal employee, and she received several performance-based promotions.

In time, Montes was named chief DIA analyst for El Salvador and Nicaragua, and at that point she started doing serious damage to American operations. In El Salvador, the American-backed government was fighting a civil war against Marxist rebels who were receiving support from Cuba and the Soviet Union. The United States supplied military equipment to the Salvadoran army, and covertly sent a Special Forces unit to help advise and train the government forces. In early 1987, the DIA sent Montes to El Salvador, where she visited the hidden Special Forces base. After she left El Salvador, Montes gave the location of the base to the Cubans. Shortly thereafter, Cuban-led Salvadoran guerrilla fighters attacked the base, and an American Green Beret was killed in the ensuing firefight. Amazingly, Montes eluded suspicion even though she was one of only a handful of people who had even known the base had existed.

Eventually, the civil wars in El Salvador and Nicaragua ended, and American intelligence efforts in those countries were scaled back. Ana Montes was put in charge of political and military intelligence on Cuba, and her Cuban handlers couldn’t believe their luck. A Cuban spy actually being put in charge of analyzing the Pentagon’s intelligence on Cuba seemed almost too good to be true. She promptly gave the Cubans the names of four American spies in Cuba, and all four were arrested. Still, Montes was not considered as a source for the intelligence leaks. Her bosses at the DIA were dazzled by her knowledge of Cuban affairs, chalking it up to her tireless work ethic. They even nicknamed her “The Queen of Cuba,” never knowing just how fitting the moniker was. During the early years of the Bill Clinton Administration, Montes fed misinformation about Cuba all the way to the White House. She led the American government into believing Cuba’s posture toward the U.S. was purely defensive, and that the Castro regime was nothing more than a harmless annoyance.

In 1996, a DIA co-worker became suspicious of Montes, and reported concerns about her. However, these concerns couldn’t be substantiated, as they were based entirely on the co-worker’s “gut feeling.” Montes was questioned, but in short time, the situation blew over. The next year, she even received a Certificate of Distinction for her performance from George Tenet, the director of the Central Intelligence Agency. However, Ana was approaching mid-life and having thoughts of settling down to have a family. Her role as a spy had made it difficult for her to have relationships, but the Cubans had no intention of letting her retire. They sent her a Cuban lover, but after a few days Montes lost interest in the gentleman.

The Price of Spying

The FBI busted a Cuban spy ring called “Wasp” in Miami in 1998, and one of the arresting agents was Montes’ sister Lucy. Both Ana and the Cubans were horrified, and for several months, she heard nothing from her handlers. Worse, she became paranoid about getting caught, suffering through bouts of depression and panic. She started seeing a psychiatrist, although she couldn’t tell her doctor the true reason for her mental and emotional state. By the end of the year, the situation had died down and she was contacted by the Cubans once again. She even managed to receive a fellowship to the National Intelligence Council, and she was moved to CIA headquarters.

The FBI suspected there was an American government employee helping the Cubans, but the Bureau had little information to go on, other than suspecting the spy was using a Toshiba laptop. Eventually the FBI asked the DIA to look into the files of current and former employees. A DIA agent named Scott Carmichael led the investigation, and became convinced Montes was the spy. At first, the FBI rejected Carmichael’s theory, but in time it was decided to put Montes under surveillance, and she was observed making suspicious phone calls from pay phones. While examining her financial records, it was seen that she had bought a Toshiba laptop at a computer store in Virginia. The FBI obtained search authorization, and went inside Ana’s apartment one weekend while she was out of town. They found the laptop, and copied the hard drive. Later, they were able to sort through her purse while she was in a meeting at work. They found codes and a New York phone number that was traced to Cuban operatives.

After the attacks of September 11, 2001, the FBI decided it was time to act. It was feared that Montes would supply information that the Cubans could in turn relay to the Taliban. She had completed her fellowship and was back at the DIA, and she was called to a meeting at the DIA Inspector General’s office. When she got there, two FBI agents were waiting for her. When they told her they were investigating a potential Cuban spy, her nerves betrayed her. She began sweating profusely, and her neck broke out in red patches. The agents had expected Montes to try to explain away any suspicions they had, but instead she asked for a lawyer. At that point, they placed her under arrest, charging her with conspiracy to commit espionage.

Ana Montes could have been given the death penalty for her actions, but she accepted a plea agreement and was sentenced to 25 years in prison. She remained defiant, insisting that her actions came as a result of America’s “unfair treatment” of Cuba, and remarking, “ Some things are worth going to prison for.”

The Cubans tried to free Montes by offering an exchange. Years earlier, an American named Assata Shakur had been convicted of killing a New Jersey State Trooper, but Shakur escaped from prison and somehow made it to Cuba. Fidel Castro’s government gave asylum to Shakur, and she still lives there. However, the Cubans offered to return Shakur to the United States in exchange for Montes, an offer that was rejected by the U.S. State Department. Montes is still serving her sentence at a maximum security prison in Fort Worth, Texas. The prison is the home of some of the most notorious female criminals in the United States, and Montes serves her time in solitary confinement.

What do you think of Ana Montes’ actions? Let us know below.

References

Pablo De Llano, “No Sign of Release for the Last Cuban Spy in a U.S. Jail” El Pais, March 8, 2017

Jim Popkin, “Ana Montes Did Much Harm Spying for Cuba. Chances Are, You Haven’t Heard of Her” The Washington Post, April 18, 2013

Scott W. Carmichael, True Believer: Inside the Investigation and Capture of Ana Montes, Cuba’s Master Spy, Naval Institute Press, Annapolis, 2007

Brian Latell, “New Revelations about Cuban Spy Ana Montes” The Miami Herald, August 2, 2014

Cold War Soviet Spies in the USA in the 1980s - CIA Mole Aldrich Ames

In the 1980s Aldrich Ames, a CIA agent, supplied the Soviets with significant numbers of classified American intelligence files – and it was not until after the Cold War finished that he was caught. But Ames was not influenced by ideology – it was something else. Scott Rose explains this Cold War spy scandal.

You can read past articles in the series about spies who shared American atomic secrets with the Soviet Union (read more here), and the 1950s “Red Scare” (read more here).

Aldrich Ames on the day of his arrest.

During the waning years of the Cold War, the Soviet Union received and paid for intelligence from one of the most notorious traitors in American history. Unlike previous American spies who betrayed their country because of communist ideologies, Aldrich Ames did so for another reason: he needed the money. 

The most ironic component of this case was that Ames was a 25-year veteran of the CIA, working in counterintelligence. His activities led to the executions of several Soviets who were working for the United States, and the resignation of a CIA Director. The effect Aldrich Ames had on the American intelligence community was nothing short of devastating.

The Agent’s Son

Born in Wisconsin in 1941, Aldrich “Rick” Ames was the son of Carleton Ames, a college professor, and Rachel Ames, an English teacher at the local high school. In 1952, Carleton went to work for the CIA, and was stationed in Southeast Asia. At that time, the region was a Cold War hotspot, as the communists had taken power in mainland China and Ho Chi Minh’s communist rebels were fighting the French for control of Vietnam. Not far away, American forces were engaged in the bloody conflict in Korea.

Carleton Ames had brought his wife and children to Asia along with him, but the family would not live abroad for very long. Carleton was an alcoholic, and his performance was negatively affected. The CIA called him back to the United States, and the elder Ames would spend the rest of his career at the Agency headquarters at Langley, Virginia, in the suburbs of Washington.

Aldrich Ames used his father’s connections to land a summer job at the CIA in 1957, and returned the next two summers. He worked as a records analyst, filing documents and performing various office tasks. Ames graduated from high school in 1959, and was accepted to the prestigious University of Chicago. However, he didn’t adjust well to life away from home, and his grades were poor. By the middle of his sophomore year, he was in danger of flunking out of school, so he dropped out and returned to his family. He regained employment at the CIA, working at office duties once again. While working at the Agency, Ames resumed his education, this time at George Washington University. At the age of 26, Ames graduated with a degree in history, and was accepted into the Career Trainee Program at the CIA. He received positive appraisals in the program, and had a blossoming romance with another agent-in-training named Nancy Segebarth. In 1969, Aldrich and Nancy were married, and he received his first assignment, in Turkey. At the age of 28, he was one of the CIA’s youngest agents; in all respects, his future seemed bright.

Assignments Around the World

Once Ames and his new wife settled in Ankara, Nancy resigned from the Agency, as the CIA had a rule that married couples weren’t allowed to work from the same office. Ames was given the task of recruiting agents to spy on the Revolutionary Youth Federation, a Marxist group in Turkey. While he was moderately successful, the CIA rated Ames’ job performance as “satisfactory,” and he was so dismayed by the evaluation that he nearly quit the CIA. After three years in Turkey, Ames was recalled to Washington and assigned to the Soviet-East European division. His new task was to recruit informants among workers at the Soviet embassy.

Ames was not very effective at recruiting Soviet spies in Washington, but was praised by his superiors for his management and planning skills. The CIA was concerned that Ames was drinking excessively, and noted this on his file in the mid-1970s. However, the Agency felt that given the right situation, Ames would flourish. He was sent to New York in 1976 to manage two established Soviet informants, and did the job well. Ames received promotions in rank and pay increases, but at times, he made careless mistakes that could have become disasters. Once he even forgot his briefcase, which was carrying classified documents, while traveling on the New York subway. Instead of firing or demoting him, the CIA merely gave Ames a verbal warning.

He was transferred again in 1981, this time to Mexico City. His wife remained in New York, and Ames had several affairs with women in Mexico. He met a lady named Maria del Rosario Casas Dupuy in 1982. Maria, a Colombian national, worked as an attaché at the Colombian Embassy, and Ames managed to recruit her as a confidential informant for the CIA. Ames was supposed to report any romantic relationships with foreign nationals to his superiors, but declined to do so. His coworkers at the CIA station in Mexico were aware of his relationship with Maria, but did not report it either. In September of 1983, Ames was recalled to Washington once more, and he brought his Colombian lover with him. Unsurprisingly, his wife served him with divorce papers the next month. 

Ames was now back at the Soviet and East European division of the CIA, and at the end of 1983, he finally reported his affair with Maria to his CIA superiors. His divorce was costly, as he was forced to pay off his and Nancy’s debts. In addition, he was required to pay alimony for the next three years. To make matters worse, Maria was from a wealthy Colombian family, and she expected to live in luxury. Ames, nearly bankrupted by his divorce, was feeling the financial heat. 

Seeking out the Soviets

Working in a division that dealt with Soviet counterintelligence, Ames was expected to make contacts at the Soviet Embassy in Washington, just as he did in the 1970s. He knew the names of important officials at the embassy, and decided he would use these contacts to remedy his financial problems. In early 1985, he sold his first trove of information to the Soviet KGB for a price of $50,000. Ames would later state that this information was not of particular importance, but that it established him as a credible source of CIA intelligence. He had entered into an alliance that he could not turn away from; the Soviets expected more information, and Ames wanted more money. In August of 1985, he and Maria were married. Ames’ motivation for betraying the United States began to evolve, from financial need into pure greed.

Over the years, the Soviets often targeted Americans who were in over their heads financially as potential sources of information. However, in the case of Ames, he saw espionage for pay as a way to do more than merely keep his head above water; he started living the good life and became addicted to it. For years, Ames had been wearing suits off the bargain rack; now he was wearing custom tailored suits that were more expensive than the ones worn by the top officials at the CIA. He and his new bride developed expensive tastes, with Ames explaining to his coworkers that this was a result of his wife’s family fortune.

By the latter part of 1985, the CIA knew something was badly wrong. Soviets who were spying for the United States were starting to disappear, and word began to trickle in later that these individuals had been arrested and executed. During 1986, Ames told his Soviet handlers that in light of these CIA losses, he was worried that he might become a suspect. The KGB by this time considered Ames too valuable to lose, and took steps to protect him. A carefully planned campaign of misinformation was carried out by the Soviets, leading the CIA to believe the mole was at the Warrenton Training Center in Virginia. The United States spent a year investigating nearly 100 people at the facility.

Later in 1986, the CIA created a mole-hunt team whose sole purpose was to find the source of the leaks. About the same time, Ames was transferred to Rome, which helped him stay under the radar of suspicion. His drinking increased, and his CIA work in Rome was less than stellar, while he continued to sell information to the Soviets. He was once again recalled to Washington in 1990, being assigned this time to the Counterintelligence Center Analysis Group within the CIA.

The CIA mole-hunt team, around 1990.

To Catch a Mole

The clues finally began to point toward Ames, as the members of the CIA mole-hunt team started to closely examine his finances. He had passed a polygraph test in 1986, which had bought him time. However, by 1990, his lifestyle, when compared to his salary, made no sense. When the CIA team examined this, it found that Ames had bought a $540,000 House in Virginia, as well as a $50,000 Jaguar. The minimum monthly payment on his credit card was more than his salary paid him in a month.

Still, Ames was hard to catch. He passed another polygraph in 1991, while a CIA operator incorrectly reported that the mole was a Russian-born agent who had infiltrated the Agency. However, by 1993, all signs pointed to Ames as the culprit. The FBI bugged Ames’ home and installed a device in his car that was used to track his movements. He was kept under constant surveillance as the case was built against him.

The Soviet Union had fallen in 1991, but Ames had continued to spy for the Russian Federation, the country that had formed out of much of the U.S.S.R. He was scheduled to attend a conference in Moscow in the spring of 1994, and American authorities decided it was time to arrest him, fearing he might defect if allowed to attend. On the morning of February 22, he was arrested in Washington and charged with spying. The same morning, FBI agents came to his home, arresting and charging his wife also.

Aldrich Ames pled guilty and was sentenced to life in prison, with no possibility of parole. His wife had been heard on surveillance tapes discussing Ames’ activities, as he had told her about his role with the Soviets. He had previously told her that he was making large amounts of money on various investments. Maria ended up being sentenced to five years in prison. CIA Director James Woolsey came under heavy fire in the wake of Ames’ capture. Woolsey had only become Director in 1993, but he was criticized for not cleaning house at the Agency after such a fiasco. The CIA as a whole endured heavy criticism for not catching Ames sooner.

The movieAldrich Ames: Traitor Within was made in 1998, and the ABC mini-series The Assets, produced in 2014, was based on Ames. Two members of the CIA mole-hunt team, Sandra Grimes and Jeanne Vertefeuille, wrote a book about the experience.

Aldrich Ames remains in prison at the Federal Detention Center in Terre Haute, Indiana. He pocketed nearly 3 million dollars from the KGB during his years of espionage. While his CIA career was merely mediocre, he was without a doubt one of most valuable Cold War spies for the Soviet Union.

What do you think about Aldrich Ames’ actions?

References

Sandra Grimes and Jeanne Vertefuille, Circle of Treason: A CIA Account of Traitor Aldrich Ames and the Men He Betrayed, Naval Institute Press, Annapolis, 2012

Chester B. Hearn, Spies & Espionage: A Directory,Thunder Bay Press, San Diego, 2006

Slava Katamidze, Loyal Spies & Ruthless Killers: The Secret Services of the USSR, 1917-1991, Barnes & Noble, New York, 2007

Peter Maas, Killer Spy: The Inside Story of the FBI’s Pursuit and Capture of Aldrich Ames, America’s Deadliest Spy, Warner Books, New York, 1995

Tim Weiner, David Johnston, and Neil A. Lewis, Betrayal: The Story of Aldrich Ames, an American Spy, Random House, New York, 1995