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Ana Montes, who spied for Cuba in 'one of the most damaging spy cases' in US history, has been released from prison

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Ana Montes, a former analyst with the Defense Intelligence Agency, the spy arm of the US military, was released Friday from federal prison in Fort Worth, Texas, after more than 20 years behind bars.

Montes spied for Cuba for 17 years, exposing the identities of undercover U.S. intelligence agents and her highly sensitive collection capabilities, until her arrest in 2001. By day, she was Cuba’s senior analyst for the Defense Intelligence Agency. At night, she typed pages and pages of government secrets she had memorized, passing them on to the Cuban secret service.

Michelle Van Cleave, who served as head of US counterintelligence under President George W. Bush, told Congress in 2012 that Montes was “one of the most harmful spies the United States has ever found.”

“She compromised everything – virtually everything – that we knew about Cuba and how we act in Cuba and against Cuba,” Van Cleave said. “So the Cubans were well aware of everything we knew about them and could use that to their advantage. In addition, she was able to influence the estimates about Cuba in her conversations with her colleagues and she also found the opportunity to provide information it has acquired to other powers.”

His espionage took place around the same time that Robert Hanssen and Aldrich Ames spied for Soviet and Russian intelligence while working for the FBI and CIA respectively. (Both are serving life sentences.) But Montes’ case was somewhat different. Hanssen and Ames took large sums of money for their espionage and physically removed classified documents from their agencies.

Rather, Montes was driven by ideology. His decision to spy was based in part on his hostility to President Ronald Reagan’s policies in Latin America, particularly US support for the Nicaraguan Contras, according to a heavily redacted report by the Department of Defense’s inspector general.

Montes was recruited by Cuban intelligence in 1984, when she was approached by a fellow student at Johns Hopkins University’s School of Advanced International Studies after expressing outrage at US actions in Nicaragua. The student was an access agent – someone who recruits spies – and introduced her to a Cuban intelligence official on the pretext that they needed Spanish news articles about Nicaragua translated into English. During a dinner in New York, Montes “agreed without hesitation to work through the Cubans to ‘help’ Nicaragua,” the inspector general’s report said.

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

Over the next few years, Montes met with his Cuban handlers every few weeks at restaurants around Washington, DC. She visited phone booths to send coded messages to the pagers used by the Cubans. She received her orders from digital messages transmitted by shortwave radio. She also took the risk of traveling to Cuba to meet people there.

As Montes rose through the career ladder and received a number of accolades for his work, the FBI received a tip about a US government employee who appeared to be spying for the Cubans, leading the bureau to begin investigating Montes, according to a 2013 Washington Post story.

She was arrested days after the September 11, 2001 terrorist attacks when the Defense Intelligence Agency was focused on Afghanistan and the director did not want to risk Montes passing on the Pentagon’s war plans.

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

“I believe she had been planning for this day, if it happened, for 17 years,” Lapp told CBS News.

The arrest was humiliating for Montes’ family, some of whom worked for the FBI. In a statement, they said she had “committed treason” against the United States and none of them knew of her spying at the time or supported her position.

“We continue to disavow what she has done and any statements she has made or may make,” the family said before her release.

Lapp, who is writing a book about Montes, declined to say where she was going after her release “out of respect for the family.” But he doesn’t expect her to jeopardize her newfound freedom by trying to connect with Cubans.

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

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