The article below was published in the Spring 2019 edition of Active Measures, IWP’s student journal.
This paper discusses the unique motivations of spy Ana Belen Montes, former military analyst for the DIA who spied on behalf of the Cuban government for over 16 years. The paper highlights the differences between Montes and other notable American spies such as Aldrich Ames or Robert Hanssen. Montes was a leading and well-respected expert on U.S. policy towards Cuba, and was a true ideologue in the sense that she sold secrets not for money or disgruntlement towards her career, but because she was fighting the good fight against unfair perceived U.S. policy towards Cuba.
When seeking to understand why a person entrusted with secrets betrays those secrets to an adversary, the four distinct driving factors the U.S. Intelligence Community (USIC) turns to are represented in the acronym M.I.C.E.: money, ideology, compromise (coercion), and ego. America’s most notorious traitors, the likes of Aldrich Ames at the CIA and Robert Hanssen at the FBI, encapsulate a trend over the last three decades of mostly middle-aged, cash-strapped, disgruntled white men who were passed over for promotion one too many times and betrayed their country. In recent history, their falls from grace enveloped various elements of M.I.C.E. As New York Times writer Scott Shane describes, “in the complex human equation that produces a turncoat, rarely is only one motive at play,” and the act of spying for Ames and Hanssen became engrossed in the pettiness of money and anger towards a lack of recognition.
Ana Belen Montes, former military analyst for the Defense Intelligence Agency (DIA) and sixteen-year spy for the Cuban intelligence service, Dirección General de Inteligencia (DGI), was driven by one predominate factor: ideology. Unlike American spies before her, Ana Montes represents a new era of betrayal and differs from these previous traitors in three significant ways: the reasons why Montes spied, the tradecraft she employed to pass sensitive classified information to her DGI handlers, and her uniqueness represents the ardent danger true ideologues like Montes pose to U.S. national security for years to come.
If the framework of ideology is based on a person’s systems and values which suit their own self-image, then Montes’ reason for spying is centered around the belief that she saw herself as a heroine serving those who could not help themselves. John Irvin, in a 2015 article about Ana Montes, described the psychological elements of ideology as such, “ideology is not the driver, but rather the vehicle which we express our own self-concept and confirm our established world view,” and concludes, “ideology is more about affirmation than enlightenment.” For Montes, this was not entirely true, as she saw herself more as a pure champion for her perceived injustice of the Reagan’s administration policies towards Latin America. This core belief was engrained during her graduate career at John’s Hopkins School of Advanced Studies, where her outspoken rhetoric got her the attention of the DGI, and she decided to accept recruitment as an agent of the Cuban government.
Montes worked her way up at the DIA, becoming known as the “queen of Cuba” around the USIC. The preeminent expert on Cuban policy, she was also developing a deepened disgust of U.S. policy toward Cuba. If her motivation as a spy for the DGI was not cemented before, it became more so during her career. Retired CIA operations officer Michael Sulick highlighted her strongly held justification for spying in his novel, American Spies, by using her own words: “I believe our government’s policy towards Cuba is cruel and unfair, profoundly unneighborly, and I felt morally obligated to help defend the island itself from our efforts to impose our values and political system on it.” Her motivation turned to action and the act of spying ultimately became the crux of her mission as justifiable means to an end.
This mindset led Montes to use her seat at the head of the table of Latin American intelligence specialists in the USIC to help shape perception and U.S. policy toward Cuba from the inside, as she herself contributed to countless intelligence estimates which served her motivations as a spy for the DGI. Montes was a foot soldier for Fidel Castro. “She spied out of conviction that Fidel Castro was both the savior of the Cuban people and champion of oppressed masses across the world, particularly in Latin America.” Montes was the embodiment of her ideological belief as she carried out her duties as a Cuban spy diligently and effectively.
The DGI’s recruitment of Montes was both dangerous and critical in the sense that they recruited an asset driven by a deep-seeded ideology and developed an asset who took it upon herself to find placement in an agency which gave her unparalleled access to sensitive information. Not only was Montes close to U.S. secrets—she helped to develop them. Furthermore, her access wasn’t just limited to that of the DIA. Montes was also privy to intelligence sharing that occurred daily throughout the entire USIC because of her position and status at the DIA.
This influential position provided Montes with valuable access from which she employed unique tradecraft to deliver stolen information to the DGI. First, Montes never actually took any documents from DIA headquarters, as described in an FBI report on Montes: “To escape detection, Montes never removed documents from work, electronically or hard copy. She kept the details in her head and went home and typed them up on her laptop.” Once she placed these typed up notes on an encrypted disk, the DGI would then send her instructions via short-wave radio to set meeting to acquire the disks. Second, Montes never took any significant money over the course of her espionage, except for small reimbursements for operational expenses. Montes never lived beyond her means, never made flashy purchases, or drew attention to herself.
Montes’ ideological motivations kept her free from the weaknesses of ideology-driven tradecraft exhibited by past agents, such as Ames and Hanssen, whose greed, arrogance, and inept sloppiness brought about their demise. Conversely, Montes employed tradecraft that kept a low-profile, while maintaining her influential standing in the USIC throughout the course of her tenure with the DIA.
Montes’ ability to contribute intelligence to the DGI without detection makes her former-lauded position in the USIC most alarming. This information was not just strictly in the possession of the Cuban government after her unauthorized disclosures. It is likely to have made its way into the hands of countries hostile to the U.S. that maintain close or friendly relations with Cuba: Russia, China, Iran, Libya, and even North Korea. Carmichael, in a 2007 Spy Cast interview at the Spy Museum with Peter Ernest, a former career operations officer for the CIA, briefly highlighted the possibility and altogether likelihood of extensive damage done by Montes not just related to what she gave to Cuba: “The issue was not just her spying for Cuba, but also who the Cubans gave the information to.” The damage done was not just solely where the information ended up, but it also revealed the identities of undercover intelligence officers, various critical intelligence projects, and U.S. strategic planning in Cuba.
What set apart Montes from others on the long list of American spies is that she had a distinguished privilege of access, ideological motivation not susceptible to a finite reward system such as money, and most importantly, was able to directly influence U.S. policy toward Cuba as the leading expert in the USIC. Carmichael remarks upon this point in True Believer: “What makes Ana Montes so extraordinary is that she not only had access to the United States’ innermost secrets but also actually created many of the secrets—the highly classified assessments we thought we knew about Cuba.” Every decision she had ever made, every assessment she contributed too, and every time she imposed her influence as a leading expert on Cuba was questioned after her arrest and eventual incarceration. Ames and Hanssen also had privileged access that made them valuable assets, but what made Montes unique is that she was a spy from day one.
From the moment she first was recruited while at John’s Hopkins, she was both an agent of the DGI and an agent of her convictions. Montes broke the Cold War era trend of middle-aged disgruntled men needing money and appreciation due to unfulfilling work dynamics. She was a woman, accepted only a small a money, had an ideological code, and for a time was at the top of her field within the USIC. Carmichael summed up Montes as a spy set apart from the rest: “Ana was not a foolish innocent who helplessly fell into someone’s trap. She did not enter the business of espionage without realizing what she was doing. Once she began spying, she was truly a master spy.”
Montes represents the dire reality of penetration into the U.S. government at its highest levels. Ideologues who penetrate the U.S. government or the USIC may pose an even greater threat than those who spy for money, for feeling slighted at work, or for what they see as the thrill of spying. The Ames and Hanssen cases show two individuals who knew at some point that they would eventually get caught and were willing to risk getting caught to accept monetary rewards from their handlers. Ana Montes was an anomaly in the sense that she did not fit the mold of the standard American spy. Armed with a misguided sense of idealism and a conviction to serve those ideals she was beholden too; she became one of the most infamous espionage cases in modern times. She was the best at her craft, and she knew it. The question is: will there be another Ana Montes… and are we ready?
 Scott Shane. “A Spy’s Motivation: For Love of Another Country. The New York Times. April 20th, 2008
 John Irvine. The Ideological Spy: Ana Montes and the Havana Starbucks. National Office For Intelligence Reconciliation. https://noir4usa.org/the-ideological-spy-ana-montes-and-the-havana-starbucks/. January 6th, 2015.
 Michael J. Sulick. American Spies: Espionage Against the United States from the Cold War to Present. Chapter 24. Washington, DC. Georgetown University Press, 2013.
 Scott W. Carmichael. True Believer. Chapter 19. Naval Institute Press. Annapolis MD. 2007.
 FBI Famouse Cases and Criminals. Ana Montes: Cuban Spy. https://www.fbi.gov/history/famous-cases/ana-montes-cuba-spy.
 Spycast- Spy Museum. Cuban Intelligence and the Ana Montes Spy Case- Interview with Scott Carmichael. https://www.spymuseum.org/exhibition-experiences/online-exhibits/agent-storm/listen-to-the-audio/episode/cuban-intelligence-and-the-ana-montes-spy-case/. August 1st, 2007.
 Scott W. Carmichael, True Believer