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Exchange Of Spies Was Critical To U.S.-Cuba Deal


We are learning more about the Cold War-style exchange of spies this week between the U.S. and Cuba. One person freed was a Cuban man who passed along information to the United States. He had unbelievable access because he worked as a cryptographer in Cuban intelligence. He is said to have provided critical information about Cuban spies operating in the U.S. President Obama described him this way.


PRESIDENT BARACK OBAMA: In exchange for the three Cuban agents, Cuba today released one of the most important intelligence agents that the United States has ever had in Cuba.

GREENE: And let's talk more about him and what he did with NPR's Dina Temple-Raston, who's on the line with us. Dina, good morning.


GREENE: So tell us who this man is.

TEMPLE-RASTON: Well, his name is Rolando Sarraff Trujillo. And his name was first reported by Newsweek, and we confirmed it with our own sources. And as you said, he was a code breaker for the Cuban Ministry of the Interior, which is like their intelligence service. And in particular, he became an expert on the codes used by spies Havana had here in the U.S. And officials say he was the big holdup in trying to do this swap and normalize relations with Cuba. The Cuban government was really reluctant to release him. And he was arrested and jailed in 1995. He was sentenced to 25 years in prison for spying for the U.S. And the Obama administration's been careful not to identify him publicly by name. But they did say that he was the man who provided crucial information on two big Cuban spy cases - the Cuban Five case and the Ana Montes case.

GREENE: Well, let's learn more about those cases that he really provided information about for the U.S. government. Let's start with the Cuban Five. This was a group that operated in south Florida, right?

TEMPLE-RASTON: Right. They were also known as the Wasp Network. And they were operating in Florida throughout the 1990s. And they basically had two assignments. The first was to keep track of Cuban exile groups in south Florida. And the second was to try to infiltrate Southcom, the U.S. military headquarters down there. You know, Cuba has always said that the five operatives were never acting against the U.S. but instead were only keeping tabs on militant exile groups in Florida. But Havana was so focused on these groups because it claimed that they were behind terrorist attacks against the island. And at the time, in the late 1990s, there were a number of hotel bombings in Cuba.

GREENE: Which made things tense at that point. I guess - so this Cuban intelligence agent, who was working for the United States, passing information to the U.S. - he was tipping off the U.S. government to these Cuban operatives?

TEMPLE-RASTON: Well, he provided that information and more specifically encryption codes that allowed the U.S. to decode messages going back and forth between Havana and the people they had in the U.S. And it took the U.S. a couple of years to build cases against the Cuban Five. You know, one of those five, who was sent back to Cuba this week, was part of a 1996 case in which he was accused of having previous knowledge that the Castro government was going to shoot down two planes that were flying near Cuba. And those planes were being flown by anti-Castro volunteers. Those volunteers were killed when the planes were shot down. Two other members of the Cuban Five were released from prison and deported a couple years ago. So now all five are back in Cuba.

GREENE: But amazing - this guy provides information, some of the Cuban Five get put in jail. And now they're all involved in a swap. I mean, their lives intertwined earlier and intertwined again now as part of the swap this week.

TEMPLE-RASTON: That's right - full circle.

GREENE: Yeah. Well, one of the other cases that this spy helped with - you were mentioning a woman, right? Tell us about her.

TEMPLE-RASTON: Well, it involved an American who worked in the Defense Intelligence Agency. And her name was Ana Montes. And she was known as one of America's most notorious spies who you've never heard of. And you've probably never heard of her because was arrested just days after the 9/11 attacks. So her case was completely overshadowed by everything else that was going on at the time.

GREENE: What exactly did she do?

TEMPLE-RASTON: Well, she was recruited by Cuban operatives in 1984. And she had worked a number of jobs that allowed her to see classified information. The last of which was this DIA - Defense Intelligence Agency - job in which she was the most senior Cuba analyst and really highly decorated. When she was caught, she was charged with communicating with Cuban intelligence through encrypted messages. And she did this in this very old-school, spymaster kind of way. She actually got her instructions from Havana through encrypted messages on a shortwave radio. And then she wrote down these messages on special water-soluble paper that dissolved so it could be quickly destroyed. And she was accused, among other things, of giving up the names of four U.S. spies in Cuba, including a U.S. intelligence officer who was operating under cover there.

GREENE: Amazing window into espionage that we're getting this week. That's NPR's Dina Temple-Raston. She's NPR's national security correspondent. Dina, thanks.

TEMPLE-RASTON: You're welcome. Transcript provided by NPR, Copyright NPR.

Dina Temple-Raston is a correspondent on NPR's Investigations team focusing on breaking news stories and national security, technology and social justice.

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