Ana Belen Montes: The American intelligence official who spied for Cuba but no one noticed until it was too late

Not only does the Castro dictatorship have countless Cuban spies crawling all over the U.S., they also have Americans who are willing to betray the U.S. to help the Cuban-communist regime.

Ana Belen Montes was one of those Americans. She was the one person behind one of the most devastating espionage operations in American history, but no one noticed her until it was too late.

J.J. Greene at WTOP:

City of Secrets: A real spy is never who you think they are

Nothing stood out about her.

She lived in a modest two-bedroom cooperative apartment on a quiet tree-lined street in D.C.’s Cleveland Park neighborhood. She drove a red 2000 Toyota Echo. She banked at Riggs Bank in the District’s Friendship Heights section. She was bright, engaging, trusted and well-adjusted at work.

But she was also something else.

Ana Belen Montes, 44, was a spy — engaged in one of the most devastating espionage operations in the history of the United States.

She was arrested on Sept. 21, 2001, and charged with conspiracy to deliver U.S. national defense information to Cuba.

Her arrest dealt a blow to the U.S. government, because she was a senior-level analyst at the Defense Intelligence Agency (DIA).

Her cover worked perfectly until, according to FBI documents, “an astute DIA colleague — acting on a gut feeling — reported to a security official that he felt Montes might be under the influence of Cuban intelligence.”

Scott Carmichael, now a former senior security and counterintelligence investigator for the Defense Intelligence Agency, was that “astute colleague.”

Another colleague who had suspicions was Chris Simmons, former chief of the Americas team with DIA’s counterintelligence research unit.

“There were gatherings in D.C. at various academic forums where Cuban intelligence officers would show up to do presentations, and she and other DIA employees went there. But they were warned by security to stop attending because ‘you’re at risk,’” Simmons said.

All the others stopped attending, he said, “but she refused.”

It wasn’t until she received an ultimatum, according to Simmons — “stop attending or get fired” — that she ceased going to the events.

Montes was so skilled at spying that during her years at DIA, even though security officials learned about her foreign policy views and were concerned about her access to sensitive information, they had no concrete reason to believe she was sharing secrets. Besides, she had passed a polygraph.I

n her 15-year career at DIA, she had acquired a top-level security clearance and become DIA’s top Cuban analyst. And she was known throughout the U.S. intelligence community for her expertise.

Montes was in possession of extremely sensitive information — which it turned out she was giving to her Cuban handlers when they’d meet at various restaurants near D.C. Metro stops.

After a long investigation, authorities determined she was a spy and figured out how she’d been turned.

“A classic tale of recruitment” is how official court documents in 2001 describe what happened.

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