The true story behind one of the most damaging spies in American history

Transcript

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Amna Nawaz: She's been called one of the most damaging spies in U.S. history.

Ana Montes passed secrets and information to the Cuban government for almost 17 years, until her arrest just days after the 9/11 attacks. After nearly two decades behind bars, she was released from prison on Friday.

I recently spoke with Jim Popkin, who chronicles Montes' fascinating story in his new book, "Code Name Blue Wren."

Jim Popkin, welcome to the "NewsHour." Thanks for being here.

Jim Popkin, Author, "Code Name Blue Wren: The True Story Of America's Most Dangerous Female Spy and the Sister She Betrayed": Thank you so much.

Amna Nawaz: So, the book is "Code Name Blue Wren." Ana Montes is the center of this story.

You have called her the most dangerous spy that most people have probably never heard of. How did you first hear about her? What made you want to tell her story?

Jim Popkin: So, I heard about Ana Montes right when she was arrested, which was 10 days after 9/11.

I was covering the FBI and Justice Department and 9/11 for NBC News at the time. I couldn't get to this story, but it really stayed with me. And I think a lot of people have never heard about her because of 9/11. It was obviously such a big distraction.

But she's a very important spy in American history.

Amna Nawaz: She led an impressive double life, right? So, by day, she was actually a senior analyst for U.S. intelligence, a Cuba expert. And, by night, she's passing secrets to the Cuban government. How did she do that?

Jim Popkin: She had two jobs. She had her real day job. She was a brilliant analyst for the Defense Intelligence Agency, or DIA, which is kind of like the CIA equivalent for the U.S. military. She would keep her head down and memorize documents all day long, classified documents. And then her night job began in Washington, D.C., in her apartment.

And she would basically upload what she had learned that day into an old Toshiba laptop, encrypt it and then, a couple of weeks later, pass that information along to her Cuban handlers, who she would meet at restaurants in Washington, D.C.

Amna Nawaz: This is a fascinating detail to me about her family, because she had four family members who worked for the FBI, including her sister Lucy, who among her many specialties was rooting out Cuban spies for the U.S. government, and no one knew anything.

Jim Popkin: It's amazing. It is absolutely amazing, four family members, her — including her sister, her brother, who was an FBI special agent in Atlanta, sister-in-law, another special agent as well.

And, as you mentioned, Lucy was a translator in Miami. Most of her job pertained to drug cases in Miami in the '80s and '90s. But she got assigned to a special unit that was looking for Cuban spies. They were very successful. She had no idea. She was a very loyal, patriotic American. She had no idea that her sister was secretly the greatest spy of — in Cuban history.

Amna Nawaz: You report that the FBI did know there was someone inside the U.S. government spying for Cuba at a very high level, right?

How did Ana Montes eventually get caught?

Jim Popkin: It was actually first the National Security Agency that figured this out by decrypting communications between Cuba and the U.S.

It ultimately lands with the FBI. They opened a full-field investigation in late 2000. They got court authority to break into her apartment in 2001. And, in her apartment, they go through her laptop, and she had very carelessly left communications, messages with the Cubans. And it was clear that she was a spy.

One of the messages said, "Thank you for providing" the true identity of an American who was based in Havana. This is someone presumably working for the CIA. "We were waiting for him with open arms."

As soon as the FBI saw that, they knew there was no doubt this is a Cuban spy.

Amna Nawaz: You also document in some detail for the first time exactly how much damage she did with that spying.

Jim Popkin: Yes.

Amna Nawaz: What did she hand over?

Jim Popkin: Well, 17 years of providing documents, classified documents, the true identities of Americans operating overseas in Havana, the names of hundreds of people who worked on the Cuba account throughout the U.S. intelligence community, and then also secrets about a super-secretive stealth satellite that the U.S. government operated and was working to spy on Russia, China, Cuba, and other adversaries.

She learned — Amna, learned about it, turned it over to the Cubans. And the Cubans have quite a track record of sharing that kind of information with Russia and other enemies. So it was a major national security disaster.

Amna Nawaz: She is now being released after nearly two decades, right?

Jim Popkin: Correct.

Amna Nawaz: Maximum security prison.

Jim Popkin: Right.

Amna Nawaz: What does life look like for her now?

Jim Popkin: She will be on probation for five years. But, as she gets out, I just have to imagine she is going to keep her head low for a long time.

She does not want to go back to this very tough prison where she has been held, as you said, Amna, for two decades. She is thought to be likely going to Puerto Rico, which is where her family is from, and she has some sympathetic relatives, and try to rebuild her life.

But she's fortunate in this sense. She's only 65 years old. Most spies in this context go away for life. They're sent to Supermax, and you never see them again. She's getting out at 65. She has a chance to maybe rebuild her life.

Amna Nawaz: Do you think she might talk to you now that she's out?

Jim Popkin: I'm probably not top of her list, but I'm going to try.

(LAUGHTER)

Amna Nawaz: I'm sure you will.

The book is "Code Name Blue Wren." The author is Jim Popkin.

Thanks for being here.

Jim Popkin: Thank you so much.