Ana Montes, Cold War spy who fed secrets to Cuba, is released

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Ana Montes, a U.S. military intelligence officer convicted of spying for the Cuban government, was released from prison Friday after more than 20 years, according to the Federal Bureau of Prisons.

Montes, 65, was the top military and political analyst working on Cuban affairs at the Defense Intelligence Agency (DIA) when she was arrested in 2001 as the result of an FBI investigation. She is one of the most highly decorated U.S. intelligence officers to have been convicted of spying for Cuba. She was granted early release from federal prison in Fort Worth, largely on account of good behavior.

For almost 17 years, Montes gathered secret U.S. government information and passed it on to intelligence officers in Havana. She disclosed the identities of at least four U.S. officers covertly operating in Cuba, provided classified photographs and documents, and alerted Cuban authorities that the United States was monitoring several of its military installations, The Washington Post reported in 2002.

Carol Leonnig speaks to “Code Name Blue Wren” author Jim Popkin on the damage ex-Pentagon intelligence analyst Ana Montes created for U.S. national security. (Video: Washington Post Live)

Montes accessed sensitive information in her role as a senior analyst for Cuban affairs at the DIA, the agency responsible for providing military intelligence about foreign countries, where she had worked since 1985. Within seven years, she had been promoted as the agency’s top official working on Cuba and was responsible for sharing secret U.S. government information on Havana with other federal agencies.

Unknown to her colleagues, who heralded her the “Queen of Cuba,” Montes was feeding that information directly back to Cuban officials.

“She is one of the most damaging spies the United States has ever found,” Michelle Van Cleave, national counterintelligence executive under President George W. Bush, told a House subcommittee in 2012.

“After 16 years of spying on behalf of Cuba, she compromised everything, virtually everything that we knew about Cuba and how we operated in Cuba and against Cuba. So the Cubans were well aware of everything that we knew about them and could use that to their advantage,” Van Cleave added.

Van Cleave, who oversaw the internal damage assessment of Montes’s actions, told the House panel that the former analyst also used her position to influence DIA colleagues’ estimates about Cuba.

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According to federal prosecutors, Montes was motivated by ideology and not financial incentive. She was never paid for anything but expenses, they told the court.

“I obeyed my conscience rather than the law,” Montes told the judge who sentenced her in 2002 to 25 years in prison following her conviction for conspiracy to commit espionage. “I believe our government’s policy toward 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 upon it,” she said.

“She secretly and without remorse systematically compromised classified information relating to the national defense of the entire country,” Assistant U.S. Attorney Ronald L. Walutes Jr. said at the time.

Senior Cuban officials publicly praised Montes after she was caught by the FBI, portraying her as an ideological ally.

According to the FBI, Montes communicated with her Cuban handlers via shortwave radios, computer diskettes and pagers, The Post reported in 2001.

Federal agents obtained court approval in 2001 to enter Montes’s apartment, where they discovered a shortwave radio, an earpiece and a laptop. They secretly copied the computer’s hard drive and restored deleted text, uncovering evidence that provided foundations to the allegations against Montes, according to an FBI affidavit.

Agents began following Montes and observed her making brief calls on pay phones outside the National Zoo, gas stations and other locations in Northwest Washington and Maryland, apparently sending encrypted messages to pagers, the affidavit said.

Montes was arrested on Sept. 21, 2001, at Bolling Air Force Base, the DIA’s head office in Washington, and FBI agents led her out of the building in handcuffs.

“She was just a very efficient spy, quiet, kind of unassuming and devastating to U.S. national security because of that,” Jim Popkin, author of a new book on Montes, told Washington Post Live in an interview Thursday, the day before her release.

According to Popkin, Montes kept a low profile at the DIA, rarely removing documents and preferring to commit sensitive intelligence to memory instead.

“Everything was in her head, and so day job would end approximately five o’clock. She’d go home, maybe work out, and she lived in a condo in Cleveland Park on Macomb Street and thus begins her night job, which was typing that classified information into her Toshiba laptop,” Popkin said. “Nearly 17 years of classified information she’s typing in virtually every day, and then she would take that, put it on disks, and meet, when convenient and when safe, with her handlers in Washington or Cuba.”

According to the FBI, authorities were first alerted to Montes in 1996 when one of her DIA colleagues raised suspicions “on gut feeling” that she was acting for Cuban intelligence. Montes was interviewed by a security official, but no action was taken, the FBI said.

Four years later, when the security official learned the FBI was working to identify a suspected Cuban agent believed to be operating in Washington, he contacted the FBI about Montes and prompted its agents to open their investigation into her.

U.S. District Judge Ricardo M. Urbina ruled in 2002 that upon her release, Montes should be placed under supervision for five years, during which time her internet and computer usage will be monitored and unpermitted contact with foreign governments forbidden. Any conditions attached to her release Friday were not immediately clear.

Shane Harris and Carol D. Leonnig contributed to this report.

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