Ana Montes, who spied for Cuba in “one of the most damaging espionage cases” in US history, has been released.

Ana Montes, a former analyst with the Defense Intelligence Agency, the spying arm of the US military, broke out of a federal prison in Fort Worth, Texas, on Friday after more than 20 years behind bars.

Montes spied for Cuba for 17 years, exposing the identities of U.S. secret intelligence officers and her highly sensitive intelligence-gathering capabilities, until her arrest in 2001. By day, she was the chief Cuba analyst for the Defense Intelligence Agency. At night, she would type out pages and pages of government secrets she had kept, and pass them on to Cuban intelligence.

Michelle Van Cleef, who was the head of US counterintelligence under President George W. Bush, Tell Congress in 2012 declared Montes “one of the most damaging spies the United States has ever had”.

“It discredited everything – almost everything – we know about Cuba and how we acted in Cuba and against Cuba,” Van Cleef said. “So the Cubans were well aware of everything we know about them and could use that to their advantage. In addition, she was able to influence estimates about Cuba in her conversations with her colleagues and also found an opportunity to present the information she obtained to other powers.”

Her espionage occurred around the same time that Robert Hanssen and Aldrich Ames spied for the KGB and the KGB while working for the FBI and CIA respectively. (Both are serving life sentences.) But Montes’ case was a little different. Hanssen and Ames took large sums of money for espionage and removed classified material from their agency.

Instead, Montes was motivated by ideology. Her decision to spy was based in part on her hostility to President Ronald Reagan’s policies on Latin America, particularly US support for the Nicaraguan Contras, according to Heavily redacted report From the Inspector General of the Department of Defense.

Montes was recruited by Cuban intelligence in 1984, when a colleague at Johns Hopkins University’s School of Advanced International Studies contacted her after she expressed outrage at US actions in Nicaragua. The student was an access agent—someone who recruits spies—and he introduced her to a Cuban intelligence official under the guise that they needed Spanish-language news articles on Nicaragua translated into English. The inspector general’s report stated that Montes, while having dinner in New York City, “unhesitatingly agreed to work through the Cubans” to help “Nicaraguans.”

She then began her espionage career with a secret trip to Cuba, where she received training from Cuban intelligence. By the end of 1985 she was working for the US Defense Intelligence Agency – possibly at the direction of the Cubans – where she had access to top secret information.

In the following years, Montes met with her Cuban handlers every few weeks at restaurants around Washington, D.C. It visited pay phones to send encrypted messages to pagers used by Cubans. It received its commands from digital messages sent over shortwave radio. She also took the risk of traveling to Cuba to meet people there.

As Montes moved up the career ladder and received a number of accolades for her work, the FBI obtained information about a US government employee who appeared to be spying for the Cubans, prompting the bureau to eventually begin investigating Montes, according to a 2013 filing. Washington Post story.

She was arrested days after the September 11, 2001, terrorist attacks as the Defense Intelligence Agency shifted its focus to Afghanistan and the director didn’t want to risk Montes passing on the Pentagon’s war plans.

Pete Lab, one of the FBI agents who investigated and arrested Montes, said she was sober during her arrest.

“I think she’s been planning that day, if it ever happened, for 17 years,” Lapp told CBS News.

The arrest was humiliating for the Montes family, some of whom worked for the FBI. They said in a statement that she had “committed treason” to the United States and that none of them knew of her spying at the time nor endorsed her position.

Prior to her release, the family said: “We continue to disavow what she did and any statements she made or might make.”

Lap, who writes book In Montes, she refused to say where she was going after her release “out of respect for the family.” But he does not expect her to jeopardize her newfound freedom by trying to contact the Cubans.

“That part of her life is over,” said Lapp. “I did what I did for them. I can’t imagine her risking her freedom.”



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