In late September 2001, while most of the nation’s law enforcement and was focused on Al Qaeda and the beginning of the “Global War on Terrorism”, one Federal Bureau of Investigation (FBI) counterintelligence investigation was closing in on a more traditional threat, namely a “mole” deep in the heart of the intelligence community working for a long-time enemy.
Ana Belen Montes was born on February 28, 1957 in West Germany to Alberto and Emilia Montes. At the time Alberto was an Army physician stationed in Germany. After a number of further deployments, the Montes’ eventually settled in Towson, Maryland where Ana most of her childhood. Ana was an extremely bright child; graduating with a 3.9 GPA from high school (Popkin, 2013) before attending the University of Virginia where she studied international affairs. During college, Ana developed the political ideology that would later lead to her decision to become a spy. To be sure, as a college student Ana began to doubt America’s foreign policy stance. Under Ana’s analysis, the United States’ foreign policy actions did more harm than good especially in how it bullied nations that were smaller and less weak than itself.
After graduating college, and despite her political stance, Ana got a clerical job in the Department of Justice’s (DOJ) Office of Privacy and Information Appeals. Based on her hard work and talent, she was soon given top secret clearance. It was also at this time that Ana began taking classes for a master’s degree in international affairs at Johns Hopkins University’s School of Advanced International Studies (SAIS). It was at SAIS that Ana was recruited to spy for the Cuban Intelligence Service (CIS). CIS was attracted to Ana because of her open opposition to U.S. foreign policy actions, as well as her position in the DOJ.
When Ana graduated from SAIS in 1988, she had already agreed to help CIS. According to Ana, international relations should be guided by tolerance, understanding, and respect, however the U.S. “never did this” as illustrated in the “cruel and unfair” laws it had against Cuba, which disrespected “Cuba’s right to develop in its own way” (CCSS, 2002). As a newly recruited Cuban spy, CIS decided that Ana’s position at DOJ, although it included a top secret clearance, would not provide much assistance in obtaining actionable intelligence. Consequently, she began looking for work in the intelligence community. As luck would have it she was able to obtain a position in the Defense Intelligence Agency (DIA) as an analyst focused in Central America the same year that she graduated. Ana’s CIS spy career, for all intents and purposes began her first day of work at the DIA.
In the beginning, Ana most likely achieved little as a spy since her access and focus did not necessarily cover what might be of interest to CIS. However, just as with her time in the DOJ, Ana soon separated herself from others, receiving a continuing stream of promotions and accommodations. Indeed, within a short time she was appointed to be the DIA top “political and military analyst for Cuba” (Popkin, 2013). Practically speaking, this meant that Ana was one of the few people that the intelligence community would go to on any information or analysis about Cuba. In essence, when it came to Cuba, she had the intelligence community’s ear. Ana promotion’s reached the peak of providing briefings to the president, the Joint Chiefs of Staff, and the National Security Council.
Her position also gave her access to an uncountable amount of information that the U.S. had on Cuba including U.S. spies in Cuba, data on Cuba’s leadership, and plans that the U.S. had on a range of Cuba related issues. She passed the majority of this information to her contacts and handlers in CIS. Like other spies, Ana’s primary weapon was her brain. Ana’ brain, however, was not average. Rather than risk detection by taking or copying documents; Ana simply memorized the documents at her desk in DIA offices at the Pentagon. She would then go home and transcribe what was in her memory to computer disks which she then encrypted and passed on to her handlers either by face-to-face meetings.
While her methods were undetectable, her attitudes were not. First, despite her position, Ana never really gave up her opinions about U.S. foreign policy. Additionally, she was often extremely aggressive in her attempts to access classified information. Consequently, she drew the attention of one of the DIA’s security officials. Although the official was not able to find much exculpatory information on Ana he remained suspicious enough to contact colleagues in the FBI counterintelligence program. Eventually, with the help of information supplied by the DIA security official, the FBI decided to open an investigation on Ana. The investigation included covert surveillance of Ana that had been authorized by the Foreign Intelligence Surveillance Court (FISC) and a team of over 50 agents (Popkin, 2013).
In early 2001, as Ana was awaiting a temporary transfer to the CIA, the FBI was able to get inside Ana’s apartment where they found the computer she used to transcribe the disks she gave to the CIS (Johnson, 2002). After copying the hard drive and analyzing it, the FBI was able to obtain the evidence necessary to prove Ana was a spy (Johnson, 2002). However, still wanting more information, the FBI delayed arrest for several months. Then in after the terrorist attacks of September 11, 2001, the FBI felt that I had no choice but immediately apprehend Ana, the decision was made all the more necessary because the DIA, unknowledgeable about the investigation, was planning on promoting Ana’s promotion to division chief, were she would most likely have or gain access to top level plans on the nation’s new war against global terrorism (Popkin, 2013). Consequently, Ana Montes was arrested by FBI agents at her office in the Pentagon on September 21, 2001. When she was captured, Ana had been spying for the CIS for nearly 16 years. The U.S. intelligence community is still unsure of the extent to which Ana’s spying hurt the nation’s national security. Ultimately, Ana was sentenced to 25 years in federal prison. Her release date is not until 2023.
One of the key lesson from the case is that when a person’s spying is motivated purely by personally choice rather than for greed, power or as a result of blackmail; they are nearly impossible to catch. Ana’s only true mistake was not taking better care of her laptop. Another lesson is the importance of social monitoring of personnel as opposed to finding “a smoking gun.” Here Ana’s office behavior, more than anything, was what led to her eventual arrest.
References
Center for Counterintelligence and Security Studies (CCSS). (2002). An unrepentant Montes sentenced to 25 years: All the world is one country. Retrieved from http://www.latinamericanstudies.org/espionage/montes-articles.pdf
Johnson, T. (2002, Jun. 16). She led two lives; dutiful analyst, and spy for Cuba. Retrieved from http://www.latinamericanstudies.org/espionage/montes-articles.pdf
Popkin, J. (2013). Ana Montes did much harm spying for Cuba – Chances are; you haven’t heard from her. Retrieved from 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/
