Ana Belen Montes – The “Queen of Cuba”
11 February 2014
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Montes blindsided the intelligence community with blatant acts of treachery. Montes was the pinnacle Analyst for the Defense Intelligence Agency (DIA), yet, in her secret life, her true fervor showed as she worked for Fidel Castro and the Cuban Intelligence Services, Dirección de Inteligencia, (DI), translated in English as the Intelligence Directorate of Cuba. Montes listened to coded messages over shortwave radio, passed secret files to handlers in busy public locales, and snuck into the Communist country adorned with a fake passport. “Your honor, I engaged in the activity that brought me before you because I obeyed my conscience rather than the law. I believe our government's policy towards Cuba is cruel and unfair, profoundly unneighborly, and I felt morally obligated to help the island defend itself from our efforts to impose our values and our political system on it.” (Montes, 2012) Montes gave this statement to the presiding judge who presided over Magistrate Number: 01-0568M. (United States of America versus Ana Belen Montes, Defendant., 2002) Montes showed no remorse, no contrition, and no regret for her actions through her career as an agent for the DI. The purpose of this brief is to explain the life, career working for the United States (U.S.) Government and Cuban government, the downfall which resulted, and the sentencing of DIA Analyst General Schedule (GS)-14 Ana Belen Montes.
On 28 February 1957, Montes was born in West Germany, on a U.S. Army base. Montes was the oldest child of Emilia and Alberto Montes. Alberto Montes was a respected Army doctor who moved his family often, due to the assignments he received. Montes moved from West Germany throughout the Midwest, and finally settled in Towson, Maryland (MD). After Montes’ father separated from the U.S. Army, he opened a private psychiatric practice and his wife, Emilia, became heavily involved in the Baltimore area Puerto Rican community.
Montes excelled in school and was often noted for her bubbly and outgoing personality.
The upbeat exterior was only a façade, though, as her life behind closed doors was anything but positive. Montes suffered through a violent totalitarian father who demanded unwavering obedience to every demand he had. Though Montes never spoke of it, or let it show, Alberto Montes bullied, beat, and controlled Montes from the age of 5 years old. Montes was 15 when her parents separated, and a decade of abuse cultivated a profound anti-Military sentiment in Montes. Montes projected her views of her father as a member of the government, on the organization as a whole—and hated them both. (Carmichael, 2007) Despite this, Montes graduated with a 3.9 grade point average from Loch Raven High School, in Towson, MD. Montes attended the University of Virginia after high school, and received her Bachelor’s Degree in Foreign Affairs in 1979. Montes moved briefly to Puerto Rico after college but could not find a suitable job. Upon the advice of a friend, she put aside her beliefs and took a job as a Clerk Typist at the Department of Justice (DOJ) in Washington, District of Columbia (D.C.). Montes excelled at the DOJ’s Office of Privacy and Information Appeals. Montes impressed her DOJ supervisors with her intelligence, bilingual ability, ambition, and outgoing personality. While she maintained her day job, Montes took classes toward her Masters’ Degree at the prestigious School of Advanced International Studies at Johns Hopkins University. (Montes acquired her degree in 1988. (Carmichael, 2007)) The circles of friends she maintained in school solidified her political views. Montes developed many negative sentiments for the U.S.’s policies in Latin America and especially for U.S. support of the rebels who fought the communist government in Nicaragua.
In 1984, the Cuban-intelligence service recruited her as an agent for the DI. (Carmichael, 2007) Montes secretly visited Cuba in 1985 and applied for government positions, which would grant her greater access to classified information. Montes accepted a job at the DIA as an entry-level research specialist and quickly rose through the ranks. Montes demonstrated her tenacity for her job in all she did. This was especially important to the Cubans because she now had a top-secret security clearance and the DI had an agent on the inside of the U.S. Government. Montes quickly became DIA’s principal Analyst for El Salvador and Nicaragua, and later named the DIA’s top political and military Analyst for Cuba. Montes was one of the U.S. government’s most adept Analysts of Cuban military affairs, and proved proficient at manipulating U.S. policy toward the Cuba itself. The Cubans started slowly, they asked for translations and bits of harmless intelligence that would appeal to Montes’ positions and views. Montes traveled to Cuba under the DIA’s Exceptional Analyst Program to study the Cuban military. At the conclusion of these trips, Montes was exclusively tasked to brief the Joint Chief of Staff (JCS), the National Security Council (NSC), and even the President of Nicaragua on the “limited capabilities” of the Cuban Military. (Carmichael, 2007) Montes excelled, in both Washington and Havana. From 1985 to 2001, from her cubicle at Joint Base Anacostia-Bolling in Washington D.C., she gained access to hundreds of thousands of classified documents, and took her lunch break at her desk in order to study, memorize, and later transcribe the information she took in day-after-day. (Johnson, 2001) Colleagues recall she could be playful and charming, especially with bosses or when she tried to talk her way into a classified briefing. Coworkers also stated Montes could be arrogant and declined most social invitations. Montes would clock out at DIA, and start her second job at her apartment. Montes never risked taking a document home, instead, she meticulously memorized by day and typed in the evenings; she regurgitated entire documents onto a Toshiba laptop. Night after night, she poured years’ worth of Top Secret, Secret, Sensitive Compartmentalized Information, and even Special Access Programs onto floppy disks bought at a neighborhood electronics store.
At a congressional hearing for Montes’ case, National Counterintelligence Executive Michelle Van Cleave would later tell Congress Montes “compromised all Cuban-focused collection programs” used to eavesdrop on high-ranking Cubans, and it “is also likely that the information she passed contributed to the death and injury of American and pro-American forces in Latin America.” (Cleave, 2012)
As an example of the damage Montes caused, she informed her Cuban Intelligence handlers about a clandestine U.S. Army base camp in El Paraíso, El Salvador. The Cuban-supported guerrillas attacked the base shortly after her visit. Among others, the guerillas killed Staff Sergeant Gregory Fronius, of 3rd Battalion, 7th Special Forces Group on 31 March 1987. The information she shared lead to the death and injury of several American and Pro-American Forces in Latin American in the late-1980s and 1990s. Montes divulged several highly classified programs and missions to include the specific names of four clandestine intelligence agents who worked in Latin America. Montes disclosed the use of the classified Cuban-Focused Collection Programs and Platforms, which contained considerable classified information of varied degrees.
Some of the most significant actions performed by Montes were enveloped in her conversations with JCS, NSC, and Senior U.S. and foreign leaders. Montes downplayed the potential for threats and the courses of action the Cuban government was capable of. Montes helped compile a controversial Pentagon report, which stated Cuba was a passive and insignificant concern in the 1998 report presented by Undersecretary of State John Bolton. Montes was a coauthor of the 1998 Cuba report, but also passed it to Havana, Cuba for their review. The report stated Cuba had a “limited capacity” to harm the United States and could pose a danger to U.S. citizens only “under some circumstances.” (Bolton, 2002)
Her tradecraft was archetypal. In Havana, agents with the DI taught Montes how to casually slip packages to agents, communicate safely in code (through telephone, computer, and shortwave radio), and how to blend in to her surrounds and “disappear” if needed. They even taught Montes how to fake her way through a polygraph test. The DI taught her how to strategically tense her sphincter muscles to create “false-positives” on the polygraph test. After ten years of espionage, Montes passed a DIA-administered polygraph in 1994. Montes received most of her orders the same way spies have since the Cold War: through numeric messages broadcast stealthily over shortwave radio. Montes would tune a small shortwave radio to a predetermined frequency and wait for the transmission broadcast to begin. A voice would dictate up to 150 numbers over the radio. Montes would key the digits into her computer, and a Cuban-installed decryption program would convert the numbers into text.
Every few weeks, Montes would dine with her handlers in D.C. area restaurants, where Montes would slide a fresh batch of encrypted diskettes to the eager recipients, face-to-face. The clandestine exchanges also took place on Montes’ vacations to carefully selected Caribbean islands. Montes even traveled to Cuba on four separate occasions with Cuba’s leadership. Twice, Montes used a phony Cuban passport to travel. She flew in disguise and traveled first to Europe to cover her tracks. (Carmichael, 2007) Montes received Pentagon approval to visit Cuba on two other occasions, on U.S. sanctioned missions for information. Montes conducted her official meetings at the U.S. Interests Building in Havana during the day but slipped away to brief her Cuban contacts in the evening.
When Montes needed to convey an urgent message, in the U.S. she did so via cellular pager. Montes would seek out pay phones at the zoo, the Washington Metropolitan Area Transit Authority, or the Hecht Company Warehouse in Washington, D.C. to call pager numbers controlled by the Cubans. Schooled in tradecraft by the Komitet Gosudarstvennoy Bezopasnosti, (KGB), (Wikipedia, 2014) translated in English as the Committee for State Security, the Cubans relied on the staple spy standards taught by their seasoned KGB instructors. Montes’ pager codes and shortwave-radio notes were written on special, water-soluble paper. If necessary, the paper would begin to dissolve if placed in water.
Montes was more successful than the Cubans’ had ever hoped for. Montes was on the cusp of another promotion, to a prominent fellowship with the National Intelligence Council, located at the Central Intelligence Agency (CIA) Headquarters in Langley. If not for a DIA Special Agent (SA) named Scott Carmichael, Montes would have had access to intelligence the DI could only dream of. In September 2000, a female intelligence officer informed the DIA the Federal Bureau of Investigation (FBI) had spent two years in a fruitless attempt to identify a U.S. government employee who appeared to be spying for the Cubans. The case had only discovered minimal information, and then came to a halt. The FBI was able to come up with only a few pieces of information during the investigation: the individual had access to the highest levels of classified information on Cuba and the individual used a Toshiba laptop to communicate with the Cuban DI.
Carmichael and his colleague Karl “Gator” James crossed the DIA databases with the FBI’s scant clues. The search initially left Carmichael discouraged and produced over a hundred possible employee matches. One of the names on the list, however, caught Carmichael’s attention: “Ana Belen Montes.” Carmichael interviewed Montes four years earlier, as her aggressive efforts to access classified information bothered a fellow Analyst of Montes. The Analyst reported the strange behavior to Carmichael, and despite the fact Montes passed the interview, Carmichael felt she lied to him.
The lead SA for the FBI, Steve McCoy, and his partner SA Pete Lapp, picked
Carmichael’s case apart; irresolute by the contingent shreds of evidence had supposedly tied Montes to the case. Carmichael was determined to prevent Montes from getting away again. He built a case on Montes and traveled to McCoy’s office to compare notes and question him with information. It took more than two months of harassment before McCoy acquiesced to Carmichael’s position, and convinced the FBI to open a Full-Field Investigation on Montes.
The fervor shown by Carmichael and McCoy persuaded a hesitant Foreign Intelligence Surveillance Court Judge to approve a surreptitious search of Montes’ DIA office, her apartment, and her vehicle. The FBI was able to capture Montes making several phone calls from pay phones. After the FBI was permitted to access Montes’ credit records, it showed Montes purchased the same model of Toshiba laptop the FBI discovered from its initial investigation.
Not one of the agents in the DIA or the FBI caught Montes meeting a known Cuban Intelligence Officer, removing classified from her workplace, or using any type of code or cipher at work. The FBI desperately needed evidence on Montes. Carmichael requested help from then-DIA director, Department of the Navy Vice Admiral Thomas Wilson. Wilson instantly supported Carmichael, and they came up with a plan to retain Montes at the DIA until they had enough evidence for conviction. During a staff meeting, Wilson played his assigned role. He acted as if the tasking of DIA employees to outside agencies was an issue, and in a guise needed for the case, put a halt to all assignments of DIA personnel outside DIA. Wilson received a backlash of complaints from other agencies, but it worked, Montes never realized the plan was all a performance to keep her in the DIA.
On May 25, 2001, Lapp and a small team trained for the occasion entered Montes’ apartment while she was out of town. The FBI searched her entire apartment and found two items they needed: a Sony shortwave radio and the Toshiba laptop. They copied the hard drive and anxiously awaited the contents of the laptop. The documents, Montes failed to delete, included details on how to decode radio-sent messages and other evidence of the tradecraft she was taught by the DI. Specifically, one file mentioned the real name of a clandestine U.S. intelligence agent in Cuba. Montes revealed the agent’s identity, and her Cuban intelligence officer thanked her by noting, “We were waiting here for him with open arms.” (Carmichael, 2007)
Carmichael and McCoy were not satisfied with the evidence thus far in the case; they wanted the cipher Montes used in her covert communications with the Cuban Intelligence. The agents believed she retained the code in her purse. Carmichael was tasked with creating a ruse to fool Montes again. This time, they wanted Montes to leave her purse behind somewhere. The successful hoax led Montes to believe she was needed for a meeting, and the location was close enough so Montes did not feel the need to bring her purse. Carmichael’s plan worked again, and McCoy was able to copy the contents of the pocketbook. The search provided the team with the pager warning codes and a DI officer’s phone number.
As the case was finally producing the information needed, the fateful events of 11 September 2001 occurred. The World Trade Center and the Pentagon’s attacks quickly changed the DIA’s focus to a wartime mission. Due to Montes’ seniority, the DIA named Montes an acting division chief and a team leader to process target lists for Afghanistan. (Montes supervisors were intentionally kept ignorant of the investigation per Wilson’s orders and did not realize the implications of Montes’ new assignment.) If Montes obtained the Pentagon’s war plan for Afghanistan, the Cubans would eagerly pass the information to the Taliban. The Cubans often shared intelligence with the adversaries of the U.S., and the DIA had a legitimate concern.
The team did not have as much information as they aspired to have, but there was no more time. Carmichael came up with his final deception in the Montes case. On 21 September 2001, a DIA supervisor called Montes with an urgent request to assist them in dealing with an issue with one of her subordinates. As she entered the room, Montes was escorted to McCoy and Lapp. McCoy attempted to casually mention details and ask Montes about her knowledge of certain situations. Montes displayed no emotion, and simply asked for her lawyer.
The FBI obtained four U.S. District Court search warrants: one for her residence, one for her car, one for her office, and for her safe-deposit box. (FBI National Press Office, 2001) An FBI evidence team successfully scoured Montes’ apartment for hours. Hidden in the lining of a notebook they found a handwritten cipher Montes used to encrypt and decrypt messages, scribbled shortwave radio frequencies, and the address of a museum in Puerto Vallarta, Mexico, where she was meant to run in an emergency. The codes were written on water-soluble disappearing paper. (Carmichael, 2007)
In analyzing the overall scope of the investigation and conviction of Montes, a few pertinent questions come to mind. Looking at the impact Montes had on U.S. National Defense, Michelle Van Cleave, a Former National Counterintelligence Executive, and an investigating officer for the case called Montes, “one of most damaging espionage cases in United States history.” (Cleave, 2012) Montes significantly affected the U.S. Foreign Policy and the actions the U.S. took with Cuba by shaping the reporting. In some instances, U.S. Government officials used information directly from conversations and reporting from Montes in their speeches, addresses to Congress, and Intelligence Briefs to the President. A specific instance of this is the Undersecretary of State, the Honorable John Bolton’s address, on 6 May 2002. (Bolton, 2002) The full extent of the damage Montes caused is unknown, but the death of several military advisors, assets, and personnel in El Salvador are directly attributed to the reporting Montes submitted to the DI. (Award of the Silver Star for Conspicuous Gallantry in Action in El Salvador, Central America, 1998)
Montes was an extremely intelligent Analyst, student, and spy. Montes successfully managed to elude capture from authorities throughout the case because of her intelligence. McCoy overlook overlooked Montes as a potential leak of information because of how talented and capable she was at her position. Montes became the “go-to” personality in dealing with Cuba, hence the name “Queen of Cuba.” (Johnson, 2001) Montes was the subject matter expert on anything that dealt with Cuba, and no one challenged her knowledge or authority on the subject. In addition, Montes successfully beat a polygraph test, and lied her way through an interview with Carmichael on the initial report from a coworker. Despite being identified, Montes had an answer for everything she did, everything she said, and everything she was involved with. Montes was expertly trained, and the Cuban DI provided her with an excuse if she was ever questioned on her actions or activities. (Carmichael, 2007)
Prevention of the incident is difficult to address because the inundation of the signs, signals, and indicators of her behavior was so prevalent. In rare instances, her guard came down around those close to her, and once she was convicted, they acknowledged her comments and actions existed the entire time. Several members of Montes’ family could have reported her, seemingly everyone in Montes’ life worked in and for the government. Montes’ brother is an FBI SA in Atlanta, her sister is an FBI Language-Analyst, her brother-in-law is also in the FBI, and her other sister is an FBI SA in charge of a Task Force to identify Cuban spies, and her former boyfriend was an Intelligence Officer specializing in Cuba, working for the Pentagon. All of these people, despite their day-to-day involvement with Montes, chose to ignore the indicators she exhibited. If any one of her friends or family reported what they later acknowledged they for many years. Montes may not have been able to get away with espionage for so many years.
Montes never received any money for her activities, she was not coerced via evidence of illicit behavior, and an inflated sense of self-importance was nonexistent. Montes believed her actions were vindicated and believed she supported the “underdog.” In her private correspondence, she refused to apologize. Spying was justified, Montes said, because the U.S. “has done some things that are terribly cruel and unfair” to the Cuban government. (Carmichael, 2007) Ana Belen Montes was officially charged with Conspiracy to Deliver U.S. National Defense Information to Cuba in Violation of Title 18, United States Code, Section 794(c). (FBI National Press Office, 2001) On 18 March 2002, Ana Belen Montes signed a plea agreement to avoid the death penalty, acknowledged her guilt, and accepted her fate. (United States of America versus Ana Belen Montes, Defendant., 2002)
Works Cited
Award of the Silver Star for Conspicuous Gallantry in Action in El Salvador, Central America. (1998). Retrieved January 23, 2014, from Home of Heroes: http://www.homeofheroes.com/valor/02_awards/silverstar/6_PostRVN/06_elsalvadore.html
Bolton, J. R. (2002, May 6). Beyond the Axis of Evil: Additional Threats from Weapons of Mass Destruction. Retrieved January 29, 2014, from The Heritage Foundation: http://www.heritage.org/research/lecture/beyond-the-axis-of-evil
Carmichael, S. W. (2007). True Believer. Annapolis, MD: U.S. Naval Institute Press.
Cleave, M. V. (2012). Cuba's Global Network of Terrorism, Intelligence and Warfare. Washington D.C.: U.S. House of Representatives - Committee on Foreign Affairs.
FBI National Press Office. (2001, September 21). FBI Arrests DIA Employee. Retrieved January 9, 2014, from National Press Releases: http://www.fbi.gov/news/pressrel/press-releases/fbi-arrests-dia-employee
Johnson, T. (2001, June 16). "Montes Led Two Lives - Dutiful Analyst and Spy for Cuba. Retrieved January 23, 2014, from http://coloquio.com/coloquioonline/montes.htm
Montes, A. B. (2012, October 16). Statement by Ana Belen Montes Who Received 25-Year Sentence for Spying for Cuba. Retrieved January 20, 2014, from http://www.latinamericanstudies.org/espionage/montes-statement.htm
Potts, A. A Most Dangerous Spy - Montes 'The Queen of Cuba'. Washington Post Magazine. Washington D.C.
Richards, A. (2007, January 23). Cubas Spies Sell to U.S. Foes. Retrieved January 23, 2014, from http://www.washingtontimes.com/news/2007/oct/26/cuba-spies-sell-to-us-foes/
United States of America versus Ana Belen Montes, Defendant., Magistrate Number: 01-0568M (United States District Court for the District of Columbia January 8, 2002).
Wikipedia. (2014). KGB. (V. Contributors, Editor) Retrieved January 23, 2014, from Wikipedia, The Free Encyclopedia: http://en.wikipedia.org/wiki/KGB
