A Cause of Concern – Understanding the Counterintelligence Threat Through A Case Study of Ana Belen Montes

by Hilary Minkler
Published with Permission

In January of 1961 the United States officially severed the political, economic and monetary relationship with Cuba, due to flourishing relationship with Russia and consistent dissatisfaction with Cuban leader, Fidel Castro. One of the effects of this relationship is the decided requirement from Cuba to increase covert operations in order to receive information and understanding of the social climate within the U.S. Government concerning U.S./Cuba and Cuba/Russia ties.[1] This concept led to the recruitment of Ana Belen Montes, one of the most successful spies of her time, in the league of Aldrich Ames and the Cambridge Five concerning effectiveness and longevity.

Ana Montes was born in 1957 at a U.S. Army installation in Germany, to Alberto and Emilia Montes. Her parents, of Puerto Rican decent were successful in their own right, Alberto worked as a U.S. Army doctor until starting his own practice in Baltimore after exiting the service; her mother worked as an activist and eventually a leader in the Puerto Rican community in Baltimore.[2] Ana had two siblings, Tito and Lucy, Lucy has continued to make public statements following Ana’s arrest, stating that she believes her parents divorce and the following had a lot to do with the mental state of Ana and the easy recruitment.

Ana attended college at the University of Virginia, with one year spent studying abroad in Spain, and then following on to attain a masters at John Hopkins University. She graduated University of Virginia with a degree in Foreign Affairs in 1979 and in 1988 obtained her masters in Advanced International Studies.[3] Colleagues and peers that have since come forward stating that during her time at John Hopkins her anti U.S. sentiment was apparent as well as her incredible distain for President Ronald Reagan.

She was recruited in 1984, a peer attending John Hopkins befriended her, she would soon find out he was actually a Cuban intelligence officer.[4] Apparently minimal convincing was needed for Montes to agree, Ana identified with the cause and believed the U.S. should stay out of foreign affairs.[5] When discussing the numerous reasons for someone to spy, monetary gain, to ideological gain is the main dividend or gain from their transgressions, in this case it was ideological. Depicted in recent quotes from Ana behind bars, “Prison is one of the last places I would have ever chosen to be in, but some things in life are worth going to prison for, or worth doing and then killing yourself before you have to spend too much time in prison.”[6]

Ana quickly attained a job within the Defense Intelligence Agency (DIA), and ascended a throne to being crowned the Queen of Cuba.[7] During this time, she was awarded over 10 prestigious appurtenances from the DIA and even taken on fact finding trips to Cuba. Her position not only allowed her placement and access but the ability to soften U.S. policy against Cuba or perception within the intelligence community through production, agreeing with her viewpoints. Additionally, her grade was that of a GS-16, she had access to hundreds of thousands of documents and would typically sit at her desk even through lunch in hopes to memorize the document in order to later transcribe it.[8] Her abilities gave her notoriety within the DIA and led to minimal thoughts of her allegiances, in retrospect, DIA analysts usually shift within their Area of Responsibility and take on different problems sets, Ana was a Cuban analyst for an excessive amount of time comparatively.

Obviously, her tradecraft was not flawless, because she eventually was caught, however Ana spied and relied information successfully for sixteen years.[9] Ana was taught directly from Cuban handlers how to use a code to communicate with them directly or in case of emergency, how to successfully do dead drops/hand offs, and even how to successfully evade a polygraph test. Most intriguing is the one pad system that was relayed over radio frequency. Cuban’s acknowledge that to run a source for so long they would need to repeatedly change their one pad system and would broadcast a new set of 150 numbers to Ana on AM frequency 7887 kHz, minding you that the code would remain in Spanish.[10] Significantly different from other high-level spies, Ana actually met her handlers every few weeks face to face and handed off information directly over a meal, typically Chinese food.

In 1996 Ana tipped off her superior by failing to follow typical protocol, and while this had no ramifications at the time, four years later it drew attention to her when the DIA believed they had a mole.[11] After tracing encryption disks back to her laptop the FBI began surveillance on Ana in hopes to catch her in the act. They started with simply following her, this is where they saw her using random payphones to message her handlers, then they found her shortwave radio used for messaging from her handlers. Finally, the FBI searched her purse and found her one pad system, confirming the transcription of messages.

The DIA and FBI’s message following her arrest depicts that they basically got lucky when catching Ana, she had provided the Cuban’s with an arsenal of information. She also tipped information about U.S. Special Forces in Latin America in hopes of the information being pushed to successfully target them. Her intelligence efforts strategically impacted and shaped Cuba’s perceptions of the United States while providing them insight into our additional foreign affairs concerning their nation. Within the intelligence community, Ana’s polygraph trick directly impacted polygraph protocol, now there is a gauge on the seating to check for sphincter tightening (the method she was taught) to deceive the machine. Her intelligence sharing have directly led to deaths and casualties that would have forced her to be charged with murder however she received twenty-five years in a brokered deal.

Ideology is one of the hardest things to impact in war and peace, Ana’s ideology could never be shaken, as most had no idea how rooted her life was in the Latin American cause. Ana’s ability two work for almost two decades as an analyst with the ability to retain new information and access high level documents with no one thinking twice about her additional activities. Ana will continue to provide debriefings until 2023, on tradecraft and Cuban affairs, regardless of U.S. and Cuban relations


[1] Office of the Historian. n.d. A Guide to the United States’ History of Recognition, Diplomatic, and Consular Relations, by Country, since 1776: Cuba. Accessed December 28, 2017. https://history.state.gov/countries/cuba.

[2] McCoy, Terrence. 2014. Cuba deal reveals new clues in case of Ana Montes, ‘the most important spy you’ve never heard of’. December 18. Accessed December 28, 2017. https://www.washingtonpost.com/news/morning-mix/wp/2014/12/18/cuba-deal-reveals-new-clues-in-case-of-ana-montes-the-most-important-spy-youve-never-heard-of/?utm_term=.359e7ccfcb8b.

[3] Patterson, Thomas. 2016. The most dangerous U.S. spy you’ve never heard of. July 11. Accessed December 28, 2017. http://www.cnn.com/2016/07/06/us/declassified-ana-montes-american-spy-profile/index.html.

[4] Ibid.

[5] Howlett, Charles. 2011. Spies, wiretaps, and secret operations: An Encyclopedia of American Espionage. Santa Barbra, CA: ABC-CLIO .

[6] Popkin, Jim. n.d. Ana Montes did much harm spying for Cuba. Chances are, you haven’t heard of her. Accessed December 28, 2017. http://www.washingtonpost.com/sf/feature/wp/2013/04/18/ana-montes-did-much-harm-spying-for-cuba-chances-are-you-havent-heard-of-her/?utm_term=.ccb3274cdffa.

[7] Intel Diary Today Staff. 2017. The Queen of Cuba: The two stories of Ana Montes. July 7. Accessed December 28, 2017. https://gosint.wordpress.com/2017/07/02/the-queen-of-cuba-the-two-stories-of-ana-montes/.

[8] Popkin, Jim. n.d. Ana Montes did much harm spying for Cuba. Chances are, you haven’t heard of her. Accessed December 28, 2017. http://www.washingtonpost.com/sf/feature/wp/2013/04/18/ana-montes-did-much-harm-spying-for-cuba-chances-are-you-havent-heard-of-her/?utm_term=.ccb3274cdffa.

[9] Latell, Brian. 2014. New revelations about Cuban spy Ana Montes. August 2. Accessed December 28, 2017. http://www.miamiherald.com/opinion/issues-ideas/article1978099.html.

[10] Groll, Elias. 2014. The Mysterious Cuban Spy at the Center of Obama’s Havana Rapprochement. December 18. Accessed December 28, 2017. http://foreignpolicy.com/2014/12/17/the_mysterious_cuban_spy_at_the_center_of_obamas_havana_rapprochement/.

[11] Patterson, Thomas. 2016. The most dangerous U.S. spy you’ve never heard of. July 11. Accessed December 28, 2017. http://www.cnn.com/2016/07/06/us/declassified-ana-montes-american-spy-profile/index.html.


Bibliography

Cereijo, Manuel. n.d. Ana Belen Montes: The chronicle of an American Spy for the Cuban Government. Newspaper Article, Latin American Studies. Accessed December 28, 2017. http://www.latinamericanstudies.org/espionage/montes-chronicle.htm.

FBI Staff. n.d. FBI History: Ana Montes: Cuban Spy. Accessed December 28, 2017. https://www.fbi.gov/history/famous-cases/ana-montes-cuba-spy.

Groll, Elias. 2014. The Mysterious Cuban Spy at the Center of Obama’s Havana Rapprochement. December 18. Accessed December 28, 2017. http://foreignpolicy.com/2014/12/17/the_mysterious_cuban_spy_at_the_center_of_obamas_havana_rapprochement/.

Howlett, Charles. 2011. Spies, wiretaps, and secret operations: An Encyclopedia of American Espionage. Santa Barbra, CA: ABC-CLIO .

Intel Diary Today Staff. 2017. The Queen of Cuba: The two stories of Ana Montes. July 7. Accessed December 28, 2017. https://gosint.wordpress.com/2017/07/02/the-queen-of-cuba-the-two-stories-of-ana-montes/.

Latell, Brian. 2014. New revelations about Cuban spy Ana Montes. August 2. Accessed December 28, 2017. http://www.miamiherald.com/opinion/issues-ideas/article1978099.html.

McCoy, Terrence. 2014. Cuba deal reveals new clues in case of Ana Montes, ‘the most important spy you’ve never heard of’. December 18. Accessed December 28, 2017. https://www.washingtonpost.com/news/morning-mix/wp/2014/12/18/cuba-deal-reveals-new-clues-in-case-of-ana-montes-the-most-important-spy-youve-never-heard-of/?utm_term=.359e7ccfcb8b.

Office of the Historian. n.d. A Guide to the United States’ History of Recognition, Diplomatic, and Consular Relations, by Country, since 1776: Cuba. Accessed December 28, 2017. https://history.state.gov/countries/cuba.

Patterson, Thomas. 2016. The most dangerous U.S. spy you’ve never heard of. July 11. Accessed December 28, 2017. http://www.cnn.com/2016/07/06/us/declassified-ana-montes-american-spy-profile/index.html.

Popkin, Jim. n.d. Ana Montes did much harm spying for Cuba. Chances are, you haven’t heard of her. Accessed December 28, 2017. http://www.washingtonpost.com/sf/feature/wp/2013/04/18/ana-montes-did-much-harm-spying-for-cuba-chances-are-you-havent-heard-of-her/?utm_term=.ccb3274cdffa.

Whitney, W. T. 2017. Defending Ana Belen Montes and Other Prisoners of Empire. September 8. Accessed December 28, 2017. https://www.counterpunch.org/2017/09/08/defending-ana-belen-montes-and-other-prisoners-of-empire/.