Ana Montes
Ana Belén Montes is an American former senior analyst at the United States Defense Intelligence Agency who spied on behalf of the Cuban government for 17 years.
Montes was arrested on September 21, 2001, and she subsequently was charged with conspiracy to commit espionage for the government of Cuba. Montes pleaded guilty to spying and, in October 2002, was sentenced to a 25-year prison term to be followed by five-years' probation. She was released on January 6, 2023, after having served 20 years behind bars.
Early life
Montes's family originated from the Asturian region of Spain, and her grandparents immigrated to Puerto Rico. She was born on February 28, 1957, at the U.S. Army Hospital in Nuremberg, West Germany, where her father, Alberto Montes, was posted as a U.S. Army doctor. Sixteen months later, her younger sister Luz, nicknamed Lucy, was born at the same Army hospital. The family moved to the United States on August 26, 1958, following the completion of Alberto's three-year posting, and by the fall of that year, they were living in Topeka, Kansas, where Montes's younger brother Alberto, nicknamed Tito, was born in June 1959. In 1967, the family relocated to Towson, Maryland, where Montes graduated from Loch Raven High School in 1975. The Montes children reportedly experienced physical and emotional abuse from their father throughout their upbringing.In 1975, Montes enrolled at the University of Virginia in Charlottesville, where she initially majored in history. Two years later, she changed her major to foreign affairs and spent her junior year studying abroad in Spain through the Institute of European Studies. During her time in Spain in 1977, she met Ricardo Fernandez Eiriz, a leftist from Argentina, with whom she began a relationship. Eiriz spoke with Montes about U.S. support for authoritarian governments, conversations that played a major role in shaping her political outlook.
During her year in Spain, as the country transitioned to democracy following the death of dictator Francisco Franco, Montes participated in street rallies with friends amid widespread anti-U.S. sentiment over American support for Franco. She wrote letters to her sister Lucy expressing a growing interest in Cuba and began identifying as a leftist. Although her relationship with Eiriz ended after her time abroad, a later report by the Department of Defense Office of Inspector General stated that she had become "attracted to the social Communist parties in Europe during her junior academic year in Spain in 1978."
Career and espionage
DOJ career and first espionage activities (1979-1985)
Montes graduated in 1979 and moved to Puerto Rico, where she worked as a receptionist at a law firm before taking a temporary position at the Universidad del Sagrado Corazón in San Juan. In December 1979, she relocated to Washington, D.C., after learning of a job opening as a clerk-typist with the United States Department of Justice in its Office of Privacy and Information Appeals. This position marked the beginning of her twenty-two–year career in the U.S. government. The Federal Bureau of Investigation conducted a routine background check on Montes but did not uncover her increasing disillusionment with the U.S. government. She quickly gained a strong reputation at the Justice Department and, after three years, was promoted to paralegal.In 1982, while working at the Justice Department, Montes began a two-year master's program at Johns Hopkins University's School of Advanced International Studies, concentrating in Latin American studies, where she connected with other leftists who shared her increasingly radical views. During her time at SAIS, she met fellow graduate student Marta Velázquez, who was described by acquaintances as politically leftist. Velázquez had studied political science and Latin American studies at Princeton University beginning in 1975, during which she traveled to Cuba to conduct field research for her senior thesis. She later earned a Juris Doctor degree from Georgetown University Law Center before enrolling at SAIS in the fall of 1982. According to the U.S. Justice Department, Velázquez became a Cuban agent in 1983 after traveling from Washington to Mexico City “to clandestinely meet with Cuban Intelligence Service officers and/or agents.” It is unclear how Cuban intelligence first established contact with her, though it is believed she may have been approached during her undergraduate trip to Cuba.
According to a grand jury indictment unsealed in 2013, the Justice Department stated that Velázquez assisted Cuban intelligence “in spotting, assessing, and recruiting United States citizens who occupied sensitive national security positions or had the potential of occupying such positions in the future—including Ana Belén Montes—to serve as agents of the Cuban intelligence service.” By 1984, Montes and Velázquez were closely associated and participated in the same SAIS graduation ceremony. Although Montes took part in the ceremony, she was handed an empty diploma because she still owed $2,300 in tuition, which she refused to pay, claiming the school had treated her unfairly and reneged on some financial aid. Later that year, on December 16, Montes attended a dinner in Manhattan with Velázquez and a Cuban intelligence officer. Defense Department investigators later reported that the twenty-seven-year-old Montes “unhesitatingly agreed to work through the Cubans to ‘help’ Nicaragua,” having already expressed moral opposition to U.S. policy in Nicaragua to Velázquez and others in class.
Within weeks of agreeing to work with Cuban intelligence, Montes’s sister Lucy began a position as a language specialist with the FBI in January 1985—a development that reportedly angered Montes. On March 29, 1985, Montes and Velázquez traveled to Madrid for what appeared to be a routine spring break trip. Although they flew to Spain under their own names, they met a Cuban agent upon arrival who supplied them with false passports. From there, they flew to Prague to obscure their movements before continuing on to Cuba, where two operatives were waiting. In Cuba, Montes and Velázquez received training in espionage from Cuban agents who had themselves been instructed by the Soviets. They were taught to communicate covertly with handlers through encrypted high-frequency shortwave radio messages transmitted from Havana, to detect surveillance, and to evade pursuers. Both requested practice polygraph examinations to prepare for security screenings when seeking classified positions within U.S. government agencies. After nearly two weeks of training, they returned to the United States, retracing their route from Havana through Prague to Madrid.
Montes sought positions that would provide access to classified information, particularly concerning the civil war in Nicaragua. She applied to the Office of Naval Intelligence and the Arms Control and Disarmament Agency before, in June 1985, submitting an application to the Defense Intelligence Agency, listing Velázquez as a character reference. According to later reports, Cuban intelligence encouraged her to apply to the DIA and assisted in preparing her application. Montes began working as an entry-level analyst at the DIA on September 30, 1985. Before Montes’s appointment at the DIA, a former colleague from the Justice Department contacted FBI background investigators and “suggested that Montes was disloyal to the United States” because of her outspoken criticism of U.S. policy in Nicaragua. She was not administered a polygraph examination during the hiring process, as the DIA was experiencing a surge in recruitment and sought to fill positions quickly.
DIA career and further espionage activities (1986-1996)
Montes became the DIA’s principal analyst for El Salvador and later for Nicaragua. Her supervisors requested that she be granted Sensitive Compartmented Information clearance, a level higher than “top secret,” which provided access to some of the Department of Defense’s most closely guarded information. During her first three months at the DIA, Montes met with her handlers at restaurants in New York City. She later shifted to meetings at Chinese restaurants in Washington, D.C., near Metrorail stations, typically every two to three weeks on weekends.To minimize the risk of detection, Montes limited the number of documents she removed from DIA facilities. She once provided her handlers with a DIA phone directory and, on occasion, classified photographs or memoranda. Aware that DIA security conducted random bag searches, she increasingly relied on memorization: rather than taking documents offsite, as spies like Robert Hanssen did—who left thousands of classified documents for the Russians at dead drop locations—she committed sensitive information to memory and relayed it to her handlers to avoid creating a paper trail.
During her first few years at the DIA, Montes received consistent praise from her supervisors and, by the late 1980s, had gained widespread recognition. She produced top-secret reports that were commended by policymakers, military departments, and members of the Intelligence Community. In early 1987, Montes embarked on her first DIA-authorized trip abroad, spending one week in Guatemala and five weeks in El Salvador as part of analyst orientation. During the trip, she visited the El Paraíso military base and received detailed briefings on its security and operations—just weeks before the leftist Farabundo Martí National Liberation Front guerrillas launched a devastating attack on the base, killing 43 Salvadoran soldiers and U.S. Green Beret Staff Sergeant Gregory A. Fronius. Military experts have long speculated that the FMLN benefited from insider assistance.
Montes’s sister, Lucy, married Chris Mangiaracina, who managed the auto fleet at the FBI’s Miami Field Office and was preparing to join the Bureau as a white-collar financial crime investigator. In late 1987, Montes’s brother, Tito, and his wife, Joan, applied for and were offered positions as clerks at the Miami Field Office, and later went on to become special agents. Within a few years of beginning her espionage for Cuba, Montes had four close relatives working for the FBI.
Montes and Velázquez remained close until 1988, when Velázquez “provoked a dispute” and publicly ended their friendship. According to the Department of Justice, the staged breakup was intended to obscure their connection as they advanced in their respective government careers. In 1990, the DIA reassigned Montes to work full-time as a long-term Nicaragua analyst. Shortly after her reassignment, the Nicaraguan civil war ended. The DIA sent Montes to meet the newly elected Nicaraguan President Violeta Chamorro and provide briefings on Nicaragua’s military capabilities, which she delivered twice. For her assistance, Montes was nominated for the DIA Meritorious Civilian Service Award, which she received in a formal ceremony later that year.
In February 1993, Montes was selected to oversee the DIA’s Cuba account and became a long-term Cuba analyst. She deliberately invited herself to any briefings that might concern Cuba, seeking to expand her knowledge, and became the Intelligence Community’s leading expert on the country’s military leadership, weapons systems, and overall capabilities. She earned the nickname the “Queen of Cuba.”
That fall, Montes purchased a second-floor co-op at 3039 Macomb Street in the Cleveland Park neighborhood of Washington, D.C. From the privacy of her apartment, she used a Sony ICF-2010 shortwave radio to tune into a pre-established frequency, known as a numbers station, at precisely 9:00 p.m. or 10:00 p.m. on Tuesdays, Thursdays, and Saturdays. A female voice would announce “Atención!” before reciting hundreds of random numbers. Montes entered the digits into her computer, a Toshiba 405CS, where a Cuban-installed decryption program converted them into Spanish-language text, which contained her tasking instructions from Havana. The coded broadcasts were nearly impossible to break without a unique cryptographic key, and because they were transmitted openly for anyone to hear, it was difficult for intelligence services to determine the intended recipient.
When Montes needed to contact her Cuban handlers, she relied on pay phones to dial pager numbers they controlled, using a system of coded signals. One code signaled “I’m in extreme danger,” while another meant “We have to meet.” To safeguard her communications, Montes recorded pager codes and shortwave-radio notes on water-soluble paper that could be destroyed instantly if necessary.
In March 1994, Montes successfully passed a DIA-administered counterintelligence polygraph examination, designed to detect espionage, sabotage, or unauthorized disclosure of classified information. It was the only polygraph she ever took during her sixteen-plus-year career with the Department of Defense. Just two months later, she provided the Cubans with the true identity of a covert U.S. intelligence officer who was preparing to travel to Cuba in an undercover capacity.
In May 1995, Montes’s sister Lucy was assigned to the Royal Flush Task Force, a top-secret operation run by the FBI, NSA, and Navy to investigate Cuban espionage in Miami. On February 24, 1996, the Cuban Air Force shot down two unarmed aircraft operated by Brothers to the Rescue, an organization opposed to the Cuban government. The following day, Montes was called to the Defense Intelligence Analysis Center to assist in evaluating options. She was quickly assigned to a task force at the Pentagon, arriving around 11:00 a.m., and remained there for the rest of the day.
Customarily, personnel on a Joint Chiefs Task Force are not permitted to leave until officially dismissed. However, citing exhaustion, Montes departed around 8:00 p.m., earlier than the expected 10:00 p.m., after receiving a phone call that left her visibly agitated, according to a coworker’s secondhand account, Pentagon investigators later reported. The source of the call remains unclear, but it reportedly raised suspicion among her colleagues. On the morning of February 26, less than 48 hours after the shootdown, a Cuban handler allegedly broke protocol by waiting for Montes on the street in Cleveland Park and flagged her down as she was about to drive to work for an impromptu briefing, desperate to learn whether the U.S. was planning to launch cruise missiles at Cuba or retaliate in another potentially deadly way.