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A counterintelligence awareness briefing where DIA employees were encouraged to report any security or counterintelligence concerns was the first step in Ana Montes' downfall. An astute colleague with counterintelligence experience reported a gut feeling that turned out to be correct. Investigation eventually determined that she really was a spy.

Montes Was Unrepentant

When Defense Intelligence Agency (DIA) analyst Ana Belen Montes was sentenced in October 2002 to 25 years in prison for spying for Cuba, she was unrepentant. Her statement to the judge at that time included the following statement:

"An Italian proverb perhaps best describes the fundamental truth I believe in. 'All the world is one country.' In such a 'world-country,' the principle of loving one's neighbor as much as oneself seems, to me, to be the essential guide to harmonious relations between all of our 'nation-neighborhoods.'...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.... I did what I thought right to counter a grave injustice."1

Montes accepted no money from the Cubans for her services. She claims that a "moral obligation" to help the Cuban people led her to become one of the more damaging spies in post-World War II history. Many Americans have opposed U.S. policy toward Cuba, and continue to oppose it, but they do not embark on a career of becoming a Cuban spy. Such actions are not driven by political opinions alone; they are usually driven by some underlying emotional or psychological need as discussed below.

Montes' crimes could have been punished by death; the leniency of her sentence was due to a plea bargain that she would cooperate with U.S. authorities on details of her spying career. 2

Damage Assessment

Montes had access to virtually everything the Intelligence Community knew about Cuba and was in a position to mold debate about Cuba on Capitol Hill and at the Pentagon and the State Department. She compromised four U.S. agents in Cuba, a major technical collection operation in Cuba, and is suspected of providing information that lead to the killing in 1987 by Cuba-backed guerillas of a U.S. Special Forces Sergeant on a covert mission in Nicaragua. More important, she is believed to have compromised plans for various U.S. military actions including the 1990-91 Persian Gulf War. With a top-level clearance, she had access to the highly classified reports on the Intelligence Community's Intelink network about other countries in addition to Cuba.

According to Christopher Simmons, a former DIA counterintelligence officer, Cuban intelligence sells U.S. intelligence secrets it gets to countries such as Russia, China, North Korea, and Iran. Simmons describes Cuba as "an intelligence trafficker." The intelligence information is traded for weapons from China, oil from Venezuela, or for votes in the United Nations. 3

Early Life, Education, Motivation, Recruitment

Ana Montes was born on a U.S. military base in West Germany in February 1957. Her father, of Puerto Rican origin, was a U.S. Army psychiatrist stationed in Germany. The family later moved to Topeka, Kansas, and then to Towson, Maryland, where she graduated from high school in 1975.

Montes parents cherished their Puerto Rican roots, but they spoke English at home and the children grew up in a mainland America environment. After leaving the Army, Dr. Montes earned a large income in a private practice. While Ana was in high school, they lived on a cul-de-sac in an upper middle-class neighborhood, and the children attended top-notch public schools with few Hispanic classmates. Her favorite things as expressed in her high school yearbook were "summer, beaches, soccer, Stevie W., P.R., chocolate chip cookies, having a good time with fun people."

While growing up, Ana battled frequently with her father who was a very strict disciplinarian and, like Ana, very strong-willed. He was a Freudian psychoanalyst who dealt sternly with his four children and tried to inculcate in them his very conservative values. In 1977 while Ana was in college at the University of Virginia, her parents had an acrimonious divorce, and Ana's mother gained custody of the children. Ana and her father had a very troubled relationship. At one point later in life, according to a friend of Ana, "she actually wrote him a letter trying to make peace with her past. He wrote back and was totally unapologetic." 4

According to Scott W. Carmichael, a DIA counterintelligence investigator who played a key role in the initial stages of the Montes investigation and wrote a book about it, writings found in Ana's apartment after her arrest had "references to abuse that she and her siblings had suffered at the hands of a domineering father and deep-seated guilt that Ana continued to feel for not protecting her younger and weaker siblings from his bullying. Ana was the oldest child, and she naturally felt responsible in part for their safety and well-being. As she saw it, she'd failed them. She should have done more. And she never forgave herself for failing to intervene and spare them from someone she viewed as an abusive bully."

Carmichael noted that "Guilt is a powerful motivator. It drives each of us and our behaviors, in unconscious ways, throughout our lives." Carmichael speculated that this may have motivated Ana Montes behavior. She could not protect her siblings from a powerful bully father, but she could help to protect the Cuban people from what she saw as another powerful bully, her own country. 5

It's noteworthy that a brother and sister both worked for the FBI and were taken completely by surprise by Ana's arrest. Ana remained very close to her mother and siblings with whom she spent all major national holidays. As a FBI translator in South Florida, Ana's sister helped bring down a network of Cuban spies, the so-called Wasp network, in 1998.

Montes earned an undergraduate degree in foreign affairs with an emphasis on Latin America from the University of Virginia in 1979. She spent her junior year abroad studying at the Institute of European Studies in Madrid. After graduation she spent a couple of months in the summer of 1979 in Puerto Rico working as a receptionist for a law firm. The family often visited relatives in Puerto Rico.

Montes' first full-time job, in 1979, was at the Justice Department (DOJ) in Washington, DC. She started as a clerical employee but was later trained as a paralegal and became one of three paralegals specializing in the Freedom of Information and Privacy Act (FOIA). This position required a security clearance. In 1982 she enrolled part-time in a two-year master's program at Johns Hopkins University School of Advanced International Studies (SAIS). She did not complete the program and get her degree until 1988.

While at the Justice Department and SAIS, Montes often spoke openly about her admiration for Cuba and her dislike of the U.S. Government policies towards Central America and Cuba. Her opinions apparently became known to Cuban officials (intelligence officers) at the United Nations who thought she might be sympathetic to their cause. After meeting with these officials in Washington, Montes decided to work for Cuba. To do that, she needed a job in the Intelligence Community, so she applied at DIA.


Montes started work at DIA in September 1985 as a research specialist for Nicaraqua at the Defense Intelligence Analysis Center (DIAC) at Bolling Air Force Base. By this time she was a fully recruited spy. She did well and advanced rapidly up the career ladder. She served as DIA's principal analyst for El Salvador and Nicaragua from 1986 to 1991. In 1992 she was selected for the DIA's Exceptional Analyst Program and then became DIA's primary political/military analyst on Cuba. Her job gave her access to Top Secret and other sensitive files. Holding this position for 10 years, her expertise was widely respected and she developed contacts with Cuba specialists throughout the intelligence and policy communities. She conducted briefings on Capitol Hill and met regularly with her CIA counterparts. In 1998 she was the chief drafter of a high-profile report on Cuba that concluded that Cuba posed no military threat to the United States. At the time of her arrest, she was scheduled for a career-advancing assignment to the National Intelligence Council at CIA.

Ana was unmarried, studious and frugal, and was admired as a highly knowledgeable and conscientious government employee, living modestly in a small condominium in Washington. She went to a gym for exercise a couple times a week. She was not gregarious, eschewing office social functions and tending not to indulge in light chatter. One official who knew her at work described her as "very warm and engaging on a personal level. She was kind of witty. She had a very sharp mind. But when you're discussing work or in a work environment, she could be very aloof and dogmatic."

Ana did have a boyfriend in 2001 with whom she went on vacation to Florida in the summer of that year. He was also an intelligence analyst for the Department of Defense with a specialty in Latin America but was based in Miami. He was completely unaware of her espionage activities.


The first step in Ana Montes' downfall came after a counterintelligence awareness briefing where DIA employees were encouraged to report any security or counterintelligence concerns about other employees so that they can be discretely investigated by an experience investigator. After this briefing, an experienced DIA counterintelligence analyst decided that he should tell a friend who was a counterintelligence investigator in the security office how and why he had come to wonder if Montes might be working with Cuban intelligence. He had observed several unusual actions and coincidences that might be best explained by her being a spy.

After discussion with the FBI, the investigator interviewed Montes. She responded appropriately to explain several points at issue but clearly lied about a phone call that prompted her to leave early from a meeting at the Joint Chiefs of Staff during a critical point in in Cuban-American relations. However, there were several potential explanations for such a lie, and this was not enough to make a persuasive case for a FBI investigation investigation of a widely respected analyst with no personal problems who had passed a routine polygraph examination just two years earlier. 5

No further action was taken until four years later when this same counterintelligence investigator learned that the FBI was trying to identity a Cuban spy known to be active in Washington. He told the FBI again about Montes, and a preliminary investigation showed that she fit the profile they were looking for. The FBI then received court approval to use intrusive methods such as physical and electronic surveillance and covert searches at home and office to build a case against Montes. They found incriminating information on her home laptop and a portable short-wave radio of a type known to be used by Cuban intelligence.

The investigation was prolonged by a desire to identify Montes' Cuban handler by observing her next face-to-face meeting with him. However, that plan was aborted as a result of the 9/11 terrorist attacks. She was arrested 10 days after the attacks, because she was being reassigned to a position with access to plans for military attacks on al-Qaida and the Taliban in Afghanistan. DIA did not want those plans to be compromised.

Espionage Tradecraft

Montes was smart and careful. She seldom removed documents from work, either electronically or in hard copy. Instead she memorized the key points and, at the end of the day, typed them on her laptop at home. She then encrypted this information and put it on diskettes.  She would meet with her handler in the Washington, D.C. area every 2 to 4 weeks to turn over the disks. She also provided information orally to the handler and responded to questions.

Cuban intelligence communicated with Montes by broadcasting encrypted messages at certain high frequencies. She had in her apartment a shortwave radio provided by the Cubans. Each broadcast was a series of numbers. Montes keyed the numbers into her computer and than used a diskette containing a decryption program supplied by the Cubans to convert the seemingly random series of numbers into a Spanish-language text.

She communicated to the Cubans by calling pager phone numbers in New York City. Calls were made with prepaid phone cards from public telephones in the Washington area. She punched in numeric codes that her Cuban handler could pick up from the pager and decode. Her messages consisted of numeric codes that had prearranged meanings.

1. "Statement by Ana Belen Montes Who Received 25-Year Sentence for Spying for Cuba," The Miami Herald, October 16, 2002. Accessed September 2010 at
Much information throughout this case study is from the following sources: "The Case of the Cuban Spy," FBI website, September 12, 2008. Accessed September 2010 at Bill Gertz, "DIA Fears Cuban Mole Aided Russia, China," The Washington Times, February 1, 2003. Accessed September 2010 at
3. Andrew Richards, "Cuba Spies Sell to U.S. Foes," Washington Times, October 26, 2007. Accessed September 2010 at Toby Westerman, "Murder and Spies: A Spy Catcher's Warning," Accessed September 2010 at
4. Tim Johnson, ""She Led Two Lives - Dutiful Analyst and Spy for Cuba," The Miami Herald, June 16, 2001. Accessed September 2010 at
5. Scott W. Carmichael, True Believer: Inside the Investigation and Capture of Ana Montes, Cuba's Master Spy, Annapolis, MD: Naval Institute Press.