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).
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.
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