Last month a career American ambassador pleaded guilty to spying for the intelligence service of Cuba. Victor Manuel Rocha served his country in positions that required the highest levels of security clearance. For 40 years, he was a covert agent. Before Ambassador Rocha was exposed, there was another prolific Cuban spy named Ana Montes, a Pentagon official, who was the lead analyst on Cuba policy. She spied for 17 years. But, Cuban spy craft isn’t just a relic of the Cold War. It’s a real and present danger to U.S. national security. It turns out, Cuba’s main export isn’t cigars or rum, it’s American secrets—which they barter and sell to America’s enemies around the world. 

It was 1999 and then first lady Hillary Clinton danced with the president of Argentina at a state dinner. President Clinton also danced the tango across the White House ballroom.

There in front wearing glasses and the airs of an aristocrat… stood Victor Manuel Rocha. He was the number two diplomat at the U.S. embassy in Buenos Aires with an impeccable reputation as a senior statesman on Latin America. He served on the National Security Council and became the ambassador to Bolivia—seen here alongside that country’s president—all that time while having the highest top secret security clearance, with access to the most sensitive U.S. intelligence.

But last December, Attorney General Merrick Garland announced Rocha’s arrest. He was charged with spying for Cuba for his entire career. 

Merrick Garland: This action exposes one of the highest reaching and longest lasting infiltrations of the U.S. government by a foreign agent.

In 2022, a man claiming to be a Cuban intelligence officer contacted Rocha and asked to meet. Rocha agreed—he had no idea the man was an undercover FBI agent. Over three meetings in Miami, the FBI recorded Rocha with a hidden camera. And according to the complaint, Rocha bragged that he got away with decades of spying by memorizing the secrets he stole… Rocha told the agent,  “what we have done…it’s enormous…more than a grand slam.” He called the U.S. quote “the enemy” 

Cecilia Vega: What do you think is the extent of damage that he did to national security?

Brian Latell: Manuel Rocha did enormous damage to– to American security. 

Brian Latell was the CIA’s top Cuba analyst at the height of the Cold War. He says in the 1980s, Rocha cold called  and struck up a professional relationship. They remained friends for decades.

Cecilia Vega: You think he approached you to get information out of you, ultimately.

Brian Latell: Yes. He never got any.

Cecilia Vega: Did you see any signs that he was leading a double life?

Brian Latell: None.

Cecilia Vega: None?

Brian Latell: None.

Cecilia Vega: What can you tell me about the trade craft that Cuba uses?

Brian Latell: They do it very, very well, in– mostly rudimentary fashions. The Cubans are not flying satellites anywhere in the world. Nearly all of their ability and– and success has been in the dimension of human intelligence. Their officers, their intelligence agents and officers are very, very good.

Brian Latell: They know their tradecraft. They practice it with great skill and with discipline. And when they recruit, they’re very careful about how they recruit and how they communicate.

Cecilia Vega: And what does Cuba do with the information it gets from all these spies?

Cecilia Vega: They have no scruples about sharing the information or perhaps marketing it, selling it to– to other countries, the Russians, maybe the Chinese

Brian Latell: If they collect information about U.S. intentions, policy intentions toward Moscow or Beijing or Tehran, it would be of interest to those countries.

That was this man’s job when he was a Cuban intelligence officer, decoding messages intercepted from the us. Jose Cohen defected in 1994.  

Jose Cohen (English translation):  Cuba shared that information with enemies of the United States, he told us. Countries like the Soviet Union for years, countries like North Korea, countries like Iran, had information about the operation of the Defense Department.

Cecilia Vega: You say Cuba may not have the weapons, Cuba may not have the arms, but they sell these secrets to the enemies of the United States?

Jose Cohen (English translation): The strongest enemies of the United States. All of that was what made me realize this is a battle between good and evil. Cuba was at the service of all the enemies of the United States.

After Jose Cohen set foot on U.S. soil he shared a vital piece of information with the FBI. That led to the investigation of more than 100 suspected Cuban agents and illegal officers and ultimately one very important spy. Cohen handed over an encryption key- like this one, used by Cuban spies to send and receive secret messages with Havana.

Three nights a week at 9 p.m. and then again at 10, a series of numbered codes was broadcast out of Havana. 

The signal could be heard for most of the 1990s up the East Coast as far north as Maine. But the coded messages were only meant to be decoded by their agents—including a Pentagon analyst named Ana Montes—who lived in this quiet Washington neighborhood.

Cecilia Vega: This is where she did all of the business, all of the spy business?

Peter Lapp: Exactly. I mean, she would listen to the high frequency messages upstairs. Tuesday, Thursday, Saturday nights, she would type up her messages on her computer in her bedroom, right up here. This is the area that she– lived in, camouflaged. The fact that she was committing espionage right here–

Peter Lapp is a retired FBI special agent who was on the team that led the Montes investigation.   

Cecilia Vega: How’d she do it?

Peter Lapp: She went to work, memorized three things every day, went home and– all classified, and then would write them up or type them up. And then every two or three weeks, she would meet in person at lunch, broad daylight, two to three hours over lunch

Cecilia Vega: Maybe I’ve seen too many movies. When I think “spies,” I’m thinking dark of night, park bench, secret cameras, fancy gadgets. That wasn’t her.

Peter Lapp: Everyone who works for the intelligence community goes home with classified information in their head. And you can’t stop that with guards and technology. It’s just– it’s– it’s undefeatable.

Lapp wrote a book on the FBI investigation into Montes. He told us Havana doesn’t pay its spies, so Americans who spy for Cuba don’t do it for money, but rather are driven by ideology. Ambassador Rocha was recruited  in the late 1970s, influenced, he now says, by the radical politics of the day. Montes was a student at the Johns Hopkins School of Advanced International Studies in the 1980s and was outspoken about her anger toward U.S. policy in Latin America when she was recruited by a Cuban intelligence officer.

Montes’ father was a U.S. Army doctor and her siblings worked for the FBI. One of her first jobs out of graduate school was as an analyst at the Defense Intelligence Agency.

Cecilia Vega: So Ana Montes was already a full-fledged Cuban spy from the moment that she set foot inside the Defense Intelligence Agency.

Peter Lapp: She walked in fully recruited, day one. Only went to DIA for the purpose of spying for the Cubans. And when you think about the other folks that have been arrested for espionage, most start loyal. They take the oath. They intend to abide by that oath. But then something happens and they flip. And Ana’s unique in the sense that she walked in from day one, and was an insider threat, and– and only went for the purpose of spying for the Cubans.

Cecilia Vega: How does a Cuban spy walk through the doors of the DIA and get a job? She didn’t have to take a polygraph?

Peter Lapp: They did not have a polygraph program at the time.

Over the course of her career, she became such an expert that she was known in the intelligence community as the Queen of Cuba. All the while she was exposing national secrets to Havana- the FBI surveilled her for a year before her arrest as she walked to work and called her Cuban handler. By that time she had revealed the existence of a top secret satellite program used by the U.S. to spy on other countries. She also gave Havana the names of 450 American intelligence officials working on Latin American issues– including four undercover officers stationed in Cuba.

And she got away with it for 17 years– until she was arrested in 2001 at her office by FBI Special Agent Peter Lapp and his partner Stephen McCoy.

Cecilia Vega: She didn’t fit the profile of a typical spy.

Peter Lapp: No. Being a woman is incredibly unique, so it doesn’t fit that typical what we would look for in a spy, which is mostly men.

Montes pleaded guilty to espionage and in exchange for not spending the rest of her life in prison, she agreed to tell the FBI everything she had done.

Through a public records request, we obtained this footage, seen here for the first time, of Montes wearing prison stripes– speaking with FBI investigators. Citing Montes’ right to privacy, the FBI denied our request for the recorded audio of their interviews. But we obtained a declassified transcript of the first day where Montes described how deep in she was. She said:

Ana Montes (Cecilia Vega reads from transcript): Ever since I started helping the Cubans, there’s been no half-way…I don’t really know how a person does it without feeling morally bound…It’s a full commitment, mentally, physically, emotionally.

I feel that what I did was morally right. That I was faithful to principles that were right.

Montes told the agents her only regret was that she was forced to cooperate with the FBI as part of her plea deal.

Ana Montes (Cecilia Vega reads from transcript): It’s tearing me up….But if the only way I’m going to see my family again… It’s the only way.  

Agent Lapp sat across from Ana Montes in the interrogation room for seven months. He said one of the most sobering moments was when she said how far she would have been willing to go for the Cubans in the week after 9/11. 

Peter Lapp: She said “if the Cubans asked me to provide them with intelligence about what we were doing in Afghanistan, I absolutely would have done that. And if men and women were killed as a result of my intelligence in Afghanistan,” she told us,”that’s the risk that they took.”

Cecilia Vega: What was the extent of the damage that she did? 

Peter Lapp: I do think she’s in that tier of some of the most notorious spies in American history and I think the damage that she did was incredibly significant.

After serving 20 years in federal prison, Ana Montes was released in January 2023. She’s now living in Puerto Rico where she has family and  has been celebrated by some as a hero…seen  here recently receiving an award from supporters. Through a lawyer, Montes declined our request for an interview. 

Last month, former ambassador Victor Manuel Rocha told a judge he was deeply sorry and pleaded guilty to acting as an agent of the Cuban government. At age 73, he was sentenced to 15 years in prison and is currently cooperating with investigators.  Just how many state secrets he gave to Cuba, we may never know. Nearly all the details of his spy craft remain classified.

Ana Montes has yet to publicly express any remorse. 

Cecilia Vega: Do you think there are other Ana Monteses in the government right now?

Peter Lapp: Oh, absolutely. Absolutely. 

Cecilia Vega: That’s chilling.

Peter Lapp: There’s no doubt that the Cubans and the Russians and others– are still penetrating our government with individuals who are loyal to them and not to us. 

Produced by Michael Rey. Associate producers, Jaime Woods and Kit Ramgopal. Broadcast associate, Katie Jahns. Edited by Joe Schanzer.

Cecilia Vega

Cecilia Vega is an Emmy Award-winning journalist and “60 Minutes” correspondent who joined the CBS newsmagazine in 2023.