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How the Cubans Put a Spy Within the American Government

The fictional world of espionage will often depict James Bond or Jason Bourne fighting off a gang of hulking goons before scaling a skyscraper and then driving a sports car off a bridge – their downtime will consist of lavish drinks and beautiful women. 

The reality is something far more subversive and far more mundane. Real-life spying requires a patience and slow exacting nature that is far removed from explosions and fist fights.  Spying after all is a dirty trade of dirty lies and dirty secrets, Bond creator Ian Fleming said so himself. 

This is the story of Ana Montes; a mild-mannered, shy and retiring intelligence analyst working tirelessly for the American government. It would take a long time before anybody cottoned on to the fact that Ana lived a secret life as a Cuban double agent. Ana had access to the most sensitive of data in American military and shared them with her Cuban cohorts. 

Ana seemed like the perfect American on paper – she was even an army brat. She was born in West Germany to a United States Army doctor. She was educated at the University of Virginia and then obtained her masters at John Hopkins. Ana was a bright, intelligent and seemingly patriotic American, the mind boggles at how somebody so ordinary could even become a double agent for a hostile foreign nation and how a top intelligence analyst within the American government managed to live on a pyramid of lies. Beyond the lies and secrets that Ana kept while in the office; Ana also had a quiet private life that her colleagues barely knew about. She was totally conspicuous, the way a double agent should be. 

The damage that Ana did to her home nation wasn’t just in telling harmless office tales. Things are never that easy… 

Ana knowingly put American troops and civilians into harm’s way until her arrest in 2001 and it is impossible to know the full extent of how much damage she caused but lives were lost from Ana’s dirty work. 

Cuba are not a great military threat to the United States (in terms of sheer military force) and it is hard to really imagine the potential physical damage that Cuba could do to their giant neighbours. Instead; Cuba are the best in the world at selling secrets. They’ve made a niche out of selling US military secrets to other nations such as China, Russia, Iran and North Korea. And this is how the Cuban government try to combat their enemy. While Cuba often look like the smaller beguiled nation living just outside of America’s shadow. They operate with their own cunning and ingenuity. Fidel Castro was after all a genius at politics.  

The Cuban Intelligence Directorate, commonly known as G2, were initially trained by the KGB upon their foundation and throughout their 40-year history they have operated in Chile, Grenada, Nicaragua and Vietnam but surely their greatest ever coup was putting an agent deep in the American DIA (Defense Intelligence Agency). 

Montes’ recruitment into the G2 and her relationship with Cuba evolved out of Montes’ anger at US foreign policy while still a student earning her degree in foreign relations. Her ire at American foreign policy drew the attention of talent-spotting Cubans and they sought to recruit Ana, this was all the way back in the mid-1980s before she even got a job in government. Montes’ anger was likely a result of her Puerto Rican ancestry and the feelings against America’s constant intervention in Latin America. 

Just after her recruitment Ana applied for a job within the DIA in a clerical functions. This meant that Ana would handle matters of defense and the most classified military secrets.

Ana was an award-winning member of the DIA; one of the core reasons Ana was never caught for so long was the fact that she never took any documents to her home and worked with a tenacity and ambition within the office that sought admirers instead of enemies. Ana memorised all of the information she got her hands on and would later type them up on her personal laptop. She would then transfer the information onto encrypted messages for her Cuban handlers. Ana received all of her own instructions by the Cuban handlers on a short-wave radio. Montes tenaciously managed her double life. A rising start in both Washington and Havana – with Fidel himself having been aware of Montes – she was a prefect analyst by day and at night she was frantically typing up the memorised messages to Havana.

During this period of intense spying, the quiet, resolute and ambitious Ana managed to rise through the ranks of the DIA.

Ana was considered a model employee and would often be given as an example to follow for new starters at the agency; Ana eventually became the Cuban-expert (nicknamed the Queen of Cuba) within the DIA and dealt intensely with Cuban affairs. The only suspicion that her colleagues had on her were the potentially more ‘left leaning’ political beliefs that Ana held, however even with this, Ana managed to pass a polygraph during a round of questioning and keep under the radar for almost twenty years. 

The most incredible thing about Ana’s activity was that she was not even paid for taking such risks, the motives being solely politically motivated. This is in contrast to other agents that were paid in the millions for selling secrets – greedy double agents such as Aldrich Ames, that took home sacks of cash. 

How Was the Spy Caught?

The DIA had strong beliefs that there was a Cuban mole in their midst. In 1996 the Cuban military shot down a plane piloted by BROTHERS TO THE RESCUE, a Cuban resistance organisation based in America. The Americans claimed that this was an act of aggression against a civilian plane with the Cubans stating the opposite. This incident alerted suspicions into how the Cuban government were so prepared for the plane before the shooting and if they had been tipped-off. Questions were raised into the possibility of a double agent. 

While called to consult at an internal meeting at the Pentagon after this incident, Montes broke protocol by failing to remain on duty until dismissed. This raised suspicion within the agency. Scott Carmichael was an investigator that took an immediate reaction to Ana and soon others were alerted. 

Was her sparkling record just too good to be true? What about the trips Ana made to Guantanamo Bay? Why was Ana always so willing to go to Cuba?  

Counterintelligence officer Scott Carmichael said, after meeting Ana and carrying out a search for all DIA employees and potential moles:

“The moment I saw her name, I knew.” 

The gut-reaction that any intelligence agent will tell you overwhelms the facts and evidence and proof they may have at the time; the instincts you hone over years and years of talking to people – you just know. Carmichael was positive he had his woman after profiling Ana. 

The FBI soon joined forces with the DIA to actually catch Montes in the act of spying. The two agencies tapped her phones, staked her out, they followed Ana intensely and they noticed her patterns… for four years.

They found the payphones around Washington D.C where Ana was stopping to make calls and traced the numbers to pagers in New York which were linked to suspected Cuban agents. 

The most ingenious sting of all was to set up an urgent meeting at work with Ana during which they could access and search her purse (which she left at her desk). It was inside her purse that they found encrypted notes that Montes was passing to her handlers. From 1985 until 2001 Ana Montes had managed to live a double life of working in the higher echelons of national defense and for the Cuban government at the same time. Ana Montes was arrested just ten days after 9/11.

So how much damage did Ana cause?  

It is impossible to really know the full extent of Ana’s spying and in sixteen years you can never find out all of the state secrets that she managed to sell. Perhaps Ana doesn’t even know herself. 

Ana made a plea bargain in avoidance of the death penalty in a plea agreement with the prosecutors and was then debriefed by the US Government, but despite this it is impossible to know just how much she gave away to an enemy state. Carmichael believes that Montes’ secret sharing lead directly to the death of an American soldier operating in El Salvador in March of 1987. Montes had only recently visited El Salvador that year and knew the precise location of the camp where Special Forces were operating before being attacked by rebel forces.  

Once the gig was up, the Cuban government washed their hands of the agent and left her out to dry. Ana was subsequently sentenced to 25 years in prison, a lenient sentence for high treason. Ana may very well be a free woman by 2027. This is subject to five years-probation.  

Ana’s own lawyer Plato Cacheris said the espionage was a moral crusade against the evils of American imperialism. Ana felt so strongly that the Cubans were subject to American strong-arming for too long. Being a Puerto Rican it is arguable that the imperialism against her own nation may have lit the fuse of revolt. 

The fact that somebody who was working completely under the radar of any investigators for such a long time and can climb to the highest ranks of the US defense is an eye opener for anybody that works in state security. 

Ana maintained a double-life and worked with a Joan of Arc-like commitment that went far beyond money and greed. The mystery remains as to how many other operatives are now (as of the time of writing) selling the secrets that keep Americans (or any other nation) safe…

After all Ana Montes wasn’t even the most famous Ana to be caught spying against America. There would later be the Russian spy Anna Chapman, caught nearly 10-years later in a major Russian spy ring. 

It is often the case in geopolitics - the enemies walk amongst us.


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