The curious case of Ana Montes: The 'most damaging' double agent freed after 20 years

Ana Montes, a former US defence intelligence analyst, who turned out to be one of the most “damaging Cold War spies”, has been freed from US Prison after spending 20 years of her life behind bars. The 65-year-old was found guilty of spying for Cuba while she was working at the American Defense Intelligence Agency (DIA). According to the US Federal Bureau of Investigation (FBI), one of the most infamous and dangerous, Cold War-era double agents was arrested just 10 days after the 2001, 9/11 attack which jolted the people of the United States along with people all around the world.  

Popularly known as the “Queen of Cuba”, the American agent recruited by Cuba, operated between 1985 to 2001 and managed to provide Havana with highly confidential US military secrets. While many wondered what possible threat an island nation could pose to a superpower, the sensitive information was then sold by Cuba to nations like China, Russia, North Korea, etc, making the United States military vulnerable to its adversaries. Montes was sentenced to 25 years of prison after she pleaded guilty in 2002.

Commenting on the damage the Cuban spy has managed to do, Michelle Van Cleave, the Head of Counterintelligence under the then-US President Geroge W Bush, told the US Congress in 2012 that she had "compromised everything - virtually everything - that we knew about Cuba and how we operated in Cuba". Born in a large middle-class Puerto Rican family, Montes’s journey is one for the books. 

The Origin of Ana: Her dissent against the US Government

Ana Montes was born to Puerto Rican parents in 1957 when the Cold War was at its peak. Anna’s father was an American army doctor, who was serving at the US Army base in Germany at the time of her birth. She attended the University of Virginia and remained politically active throughout her academic pursuit.  According to CNN, in 1984, Montes was working a clerical job at the Justice Department in Washington. As per the FBI, Montes had a very aggressive opinion against the US government and frequently criticised Washington’s policies towards Central America. 

The infamous spy was against the Reagan administration’s decision to support rebel groups fighting pro-communist regimes in Central America. Speaking on his outlook towards the US administration, FBI Special Agent Pete Lapp asserted, “She felt that the U.S. didn’t have the right to impose its will on other countries”. As per CNN, Lapp was the man who later led the investigation against Montes which ultimately led to her arrest. 

Her dissent attracted Cuban attention: Her recruitment as a spy 

Montes’s aggressive stance against the US administration soon attracted attention from people with malicious intent. During her academic pursuit at John Hopkins University, Monte’s passionate views against Washington got noticed and she was introduced to the recruiters of the Cuban cause. After she agreed to help the “Cuban officials”, in 1985, she applied at DIA, which is a key producer of intelligence for the Pentagon. According to the FBI, after being fully recruited as a Cuban spy, Montes never removed important documents electronically, she memorised the details and started blurting them out on her laptop at home. She used to communicate with the Cuban officials in code via short-wave radio. 

The Federal Agency also stated that during her time at the intelligence agency, people started getting suspicious of her, due to her aggressive political views. However, the shrewd American spy managed to pass a polygraph test. The DIA, therefore, had no reason to believe that Montes was involved in something malicious due to a lack of evidence against her.

The Downfall of Ana

According to the FBI, her downfall started in 1996, when one of her DIA colleagues suspected her involvement with Cuban intelligence. The DIA official reported his suspicion to the security officials, however, Montes vehemently denied the accusation. The matter was brushed under the carpet until four years later when the FBI started working to uncover a Cuban spy. The DIA official informed the FBI about his suspicion and after reviewing the facts surrounding the case the American Bureau opened an investigation against Montes. 

Through heavy surveillance, the FBI already had a solid case against Montes. However, they wanted to delay her arrest, since they also wanted to track her Cuban handlers. The FBI plot changed completely after America witnessed the most devastating terrorist attack on September 11, 2001. According to the Federal agency,  Montes was about to be assigned with work related to US warplanes amid the 9/11 crisis, as a result, both the FBI and DIA decided to arrest the double agent to avoid any further leaks. Montes later acknowledged her wrongdoings as she pleaded guilty in 2002. Not only this but America’s “most damaging” double agent also revealed four other American undercover intelligence officers who were working in Cuba. 

According to the Federal Bureau of Prisons, Montes was released from Federal Prison located in Fort Worth, Texas on Friday. For the next five years, she will be placed under court-order supervision and her internet usage will also be monitored. The 65-year-old is also barred from working for the government or contacting any foreign actors without permission. While the US has prevented any further leak of confidential information with the arrest of Montes, the repercussions of the damage inflicted by Montes are still quite prevalent for the Pentagon.