In recent weeks, news outlets have reported that the United States sent intelligence assets to Cuba and the CIA set up a Cuba task force to put more pressure on Havana. Before these developments, a former official who I spoke with had laid out the signals he was seeing, which seemed to indicate that President Donald Trump will move forward — as he said in the spring. Perhaps it depends on the war with Iran.
As Cuba faces pressure emanating from Washington, retired FBI Special Agent Peter Lapp described Cuba’s intelligence capabilities. Its Directorate of Intelligence (DI) has long been seen as a force that punches above its weight, the result of extensive training by the KGB during the Cold War.
Today, Cuba may be weak because of the Trump administration’s oil blockade and sanctions, Pete said, but that does not mean the DI has weakened. “I think that they’re probably ramped up quite a bit right now,” he told me.
At one point in the interview, he said Cuba may be leveraging some Americans’ disapproval of Trump to recruit more spies. We have previously seen their moles channel sentiment around Trump for cover, as when former U.S. Ambassador to Bolivia Manuel Rocha purported to be a big Trump supporter — while silently gathering intelligence and exerting influence for more than 40 years.
Pete was less worried about covert action than the Directorate tapping its network of illegals, “their crown jewel.” He told me that at the FBI, “the difficult part of getting to understand the Cubans was really focusing, in my opinion, not on the day-to-day activity of the intelligence officers we were following, but the ‘unsub’ investigations — the unknown subjects.”
We discussed the Wasp Network, a group of illegals who in the 1990s gathered intelligence on military bases in South Florida, areas that would be important in the event of a Cuban invasion.
In 2001, Pete helped expose the espionage of Ana Montes, a top Defense Intelligence Agency analyst. He secretly entered her home in Washington, D.C. when she was in Miami. “It was a pretty cool moment, I have to be honest with you,” he said. “When you have the key and you’re sneaking in… We had surveillance on her, so we knew she wasn’t going to come home. But what if we put a book back the wrong way?”
In the end, Pete found her laptop under her bed. It tied her to Cuba. She had been extremely careful, but the device contained 11 pages of Spanish text from her to the Cubans and vice versa, he said. Among the information she shared over the years was the existence of a Special Access Program inside the National Reconnaissance Office, which operates spy satellites. “Four sentences could have been death penalty-eligible evidence,” Pete said.
Outside of Cuba’s network of illegals, Pete said he has no doubt that Cuba is leveraging China’s and Russia’s expanding SIGINT facilities on the island. “They’ve always bartered intelligence. It’s part of what has kept the regime in power for all these years.”
He said he is also sure that Cuba shared details on that ultra-secret satellite program. “That was a chip they absolutely played and gave to other intelligence services,” he said.
I don’t know who leads the DI now and neither did Peter. “They’re very secretive about their leadership within the Cuban Intelligence Service,” he said. “Although it’s kind of funny, some of the individuals that I had seen or actually had investigations on in the past are on Facebook.”
I found an archived article from 2001 which reported that a retired FBI agent had testified that the DI’s former leader was Brig. Gen. Eduardo Delgado Rodríguez, who oversaw the fatal downing of a civilian aircraft operated by humanitarian group Brothers to the Rescue. It is notable because in May, the Trump administration issued a superseding indictment regarding the shoot down.
I asked Peter what Cuban defectors had to say about the DI. “All of them told us that the United States is their top priority. So if you flip that around, for the United States, our top priority is China, followed by Russia and then followed by pretty much everyone else.”
He also said that Fidel Castro’s photo did not hang in the DI headquarters, though this part of the chat was cut for time. “I just assumed there would be a picture of Fidel Castro on the entrance and heavily guarded. And [the defectors said], ‘No, there’s no pictures of Fidel because Fidel is everywhere. They don’t need his picture up.’” The implication was that everyone knew they were being watched.
In terms of security, the police state required less manpower at the headquarters. “Although there’s an armed guard there, it’s not as guarded as I would say the CIA is or the FBI because people just don’t stroll off the street and walk into the headquarters of the Cuban intelligence service... They just know that that's a building you don't go into.”
One of the defectors he spoke with was a man who had a chance to assassinate Castro. He had been a security officer traveling with the president on a state visit to another country. “The Cubans gave him a Smith & Wesson .45 caliber weapon to protect Fidel… Fidel had his entire bedroom shipped to this place that he was staying so that he could get a good night’s sleep. His bed, his mattress, his sheets, the whole thing. And [the defector] was just disgusted with this. Your average Cuban is living in poverty, and Fidel needed his own bed.” Ultimately, the man decided not to kill Castro because he didn’t believe anything would change for his country.
Pete believed that CIA Director John Ratcliffe’s visit to Cuba in May, to meet with his intelligence counterpart, was likely a warning to Havana. He said the Cubans are enduring hardship simply to survive and that “the more they become disgruntled, the more the possibility that they start working with U.S. intelligence.”
Episode length: 39 minutes
Listen: On Spotify | On Apple Podcasts
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