Cuban spy Ana Montes was released on January 6 2022 after serving 20 years of a 25-year sentence. Ana Montes had flown under the radar for many years. Her father was an Army doctor, and she was born in Germany while he was stationed there in 1957. Although she joined the Defense Intelligence Agency (DIA), she detested U.S. policies in Latin America and elsewhere. She spied for the Cubans for 17 years until she was caught and arrested just a few days after 9/11.
Montes grew up in Topeka, Kansas, where her father was transferred to. He was a strict disciplinarian who would beat his children with a belt, which goes contrary to his profession as a mental health professional. CIA investigators later stated that abuse may have led his daughter to become “anti-authoritarian” and been a reason she began spying against her country.
As a teen, she already had leftist leanings and was enthralled by the Cuban Revolution; she hung a picture of Che Guevarra in her bedroom. As a student, she stood out with her criticism of the U.S. and its support of the Contra against the Sandinista government in Nicaragua.
At one point, an Argentine boyfriend suggested she meet “his friend” at the Cuban embassy. Thus she became a spy for Cuba.
She first worked at the Department of Justice, but later, at the suggestion of her Cuban handlers, she applied for a job with the DIA. The background check conducted by the FBI didn’t come up with anything suspicious and she joined the agency in 1985.
The Queen of Cuba undermined US interests for decades
Ana Montes was smart and worked hard, and although she was hired as an entry-level research specialist, she quickly rose up the ranks. Montes would become the DIA’s principal analyst for El Salvador and Nicaragua, where she put American lives in danger as due to her position by relaying the locations of Green Berets in El Salvador to her Cuban handlers. Ana Montes also relayed the names of four agents the U.S. had in Cuba.
During that time, only 55 Green Berets advisors were permanently allowed in El Salvador. While other teams would come in for training missions, most El Salvadoran Army Brigades had only two Special Forces advisors, which made these men prime targets for attacks.
In 1987, just weeks after Montes was allowed to visit the El Paraiso cuartel of the 4th Brigade, an attack by the FMLN (Farabundo Marti National Liberation Front). A total of 69 El Salvadoran soldiers were killed and 79 more wounded in the attack; SFC Greg Fronius, a Green Beret from the 7th SFG was also killed. Between 1982 and 1993, 21 Americans lost their lives in El Salvador.
Montes was later named the DIA’s top political and military analyst for Cuba. In the DIA headquarters, she was a rockstar and became known as the Queen of Cuba. However, leading a double life was made even more stressful when her brother and sister both joined the FBI.
Montes never took home classified documents or electronic files. Instead, she would memorize them and, when she got home, type them into her computer onto encrypted disks. She would then receive instructions on shortwave radio to where to pass them to her Cuban handler.
Ana Montes is discovered and exposed
When her sister Lucy helped the FBI break up a Cuban spy ring in South Florida, she learned Cuba had a mole inside a Washington intelligence agency. The double agent was known to have had a student loan paid off by the Cubans, owned a particular type of Toshiba computer, and traveled to Guantanamo Bay at a specific time during the summer of 1996.
Investigators immediately knew that Montes was the culprit. They tracked down a store in Alexandria, VA, where Montes had bought the computer. They tracked her movements, put taps on her phone, and learned that she’d use several different public phones in Washington. They traced the numbers and it was traced to pagers in New York that the FBI confirmed were used by Cuban intelligence agents.
FBI agents searched her home when she was away and found the shortwave radio that Cuban intelligence had supplied. At her work, her purse was searched when she was out of the office, and the agents found the codes she used to communicate with her Cuban handlers.
But 9/11 put an end to all that. Montes was assigned to a DIA team that would analyze American bombing raids in Afghanistan, which would give her access to U.S. war plans so she was arrested on September 21, 2001.
Unlike other Americans who spied for money, Montes was a “true believer” in counterintelligence terms. Other than expenses, she was never paid a dime for her spying.
Montes agreed to a plea deal that would put her in prison for a 25-year sentence. After her January 2023 release she moved to Puerto Rico. A book by Jim Popkin about her spying came out just prior to her release.