CIA mole, now out of prison, helped U.S. identify Cuban spies

He was, in many ways, a perfect spy – a man so important to Cuba’s intelligence apparatus that the information he gave to the CIA paid dividends long after Cuban authorities arrested him and threw him in prison for nearly two decades.

Rolando Sarraff Trujillo has now been released from prison and flown out of Cuba as part of a swap for three Cuban spies imprisoned in the United States that President Barack Obama announced Wednesday in a televised speech. Obama did not give Sarraff’s name, but several current U.S. officials identified him and a former official discussed some of the information he gave to the CIA while burrowed deep inside Cuba’s Directorate of Intelligence.

Sarraff’s story is a chapter in a spy vs. spy drama between the United States and Cuba that played on long after the end of the Cold War, decades after Cuba ceased to be a serious threat to the United States. The story – at this point – remains just a sketchy outline, with Sarraff hidden from public view and his work for the CIA still classified.

Chris Simmons, who was the chief of a Cuban counterintelligence unit for the Defense Intelligence Agency from 1996 to 2004, said that Sarraff had worked in the cryptology section of Cuba’s Directorate of Intelligence and was an expert on the codes used by Cuban spies in the United States to communicate with Havana. Sarraff’s family said that he studied journalism at the University of Havana and had the rank of first lieutenant at the intelligence directorate.

It is not clear when Sarraff, now 51, began working for the CIA. But, according to Simmons, once he did he passed encryption information to the CIA that led to the arrest of a number of Cuban agents operating in the United States.

In his speech Wednesday, Obama referred to Sarraff as “one of the most important intelligence agents that the United States has ever had in Cuba,” someone who “provided America with the information that allowed us to arrest the network of Cuban agents that included the men transferred to Cuba today, as well as other spies in the United States.”

Hours later, the director of National Intelligence, the head of the U.S. intelligence community, issued a statement saying the information from Sarraff - the statement did not name him - had helped the government arrest and convict several Cuban spies inside the United States. The convictions included a senior analyst at the Defense Intelligence Agency named Ana Belén Montes; a former Department of State official, Walter Kendall Myers, and his wife, Gwendolyn Myers; and members of the Red Avispa network, or Wasp Network, in Florida.

Jerry Komisar, who ran CIA clandestine operations in Cuba during the 1990s, said that “there were a number of people in the Cuban government who were valuable to the U.S., just as there were a number of people in the U.S. government who were helpful to the Cubans.”

Simmons said that Cuba’s spy service regularly communicated with its agents in America using encrypted messages sent over shortwave radio. After Sarraff helped the United States crack the codes, he said, the FBI was able to arrest Cuban spies years after Sarraff was discovered and put in prison in Cuba.

“When Roly was providing information, he was giving us insights about where there were weaknesses in the Cuban encryption system,” Simmons said.

Cuban authorities arrested Sarraff in November 1995. According to members of his family, he went to work one day and never came home. Cuban officials told the family for more than a week that Sarraff was on a job in the country’s interior and would be back soon.

According to Simmons, “had it not been for his parents being senior officials in the Cuban government, they would have executed him.”

He was tried in 1996 for espionage, revealing state secrets and other acts against state security. He was sentenced to 25 years in prison.

“He is always maintained his innocence” his sister, Vilma Sarraff, said by telephone from Spain.

She said that Sarraff’s daughter was 7 years old when he was arrested.

Multiple news accounts in recent years have identified Sarraff as a former Cuban intelligence officer who had been imprisoned. The accounts named him as a possible candidate to be released if the United States and Cuba were ever to agree to a spy swap.

He was mentioned briefly in a January 2008 State Department cable sent from a U.S. official in Cuba to various agencies in Washington, including the CIA. In the cable, part of the trove of documents made public by WikiLeaks, his name is on a list of political prisoners put together by a human rights group in Cuba.

In 2011, a man identifying himself as Sarraff’s brother wrote a blog post saying that Sarraff had been in prison for 16 years. In the post, he recalled when his brother was arrested and that his parents were told that Sarraff was “accused of being a confessed CIA agent.”

But if Sarraff had in fact collaborated with U.S. intelligence agencies to help snare Cuban agents living in the United States, as the presidents of both countries suggested Wednesday, it was certainly not something he ever discussed with his family, Vilma Sarraff said.

“If what they are saying is true, fine, he paid that debt with 20 years in prison,” she said.

Vilma Sarraff said her brother was in solitary confinement for 18 years. An avid painter and poet, he was not permitted any painting supplies or other distractions. He was also denied parole, Vilma Sarraff said.

She said her brother had been calling his family regularly from prison, but that they had not heard from him in several days. She said her family had been told Sarraff had been released from prison but had not heard directly that he was part of a prisoner exchange.

She said she had no idea where he was.

“They did not say where they had taken him,” she said, becoming irate. “How is it possible that they take my brother out of the country without telling his parents? My parents are at the point where my father is likely to have a heart attack!”

With Wednesday’s exchange of imprisoned spies and the leaders of the United States and Cuba talking in a substantive way for the first time in more than 50 years, some people who were part of the spy games between the two countries now wonder just how much it was worth it.

Komisar, the former CIA officer, said that in retrospect there was little need for U.S. intelligence services to devote so much attention to Cuba. He said it was a country with a decrepit military that he said posed no strategic threat to the United States since the Soviet Union pulled its missiles off the island in 1962.

He also said that after decades of cloak-and-dagger activities between the two countries, “at the end of the day I would call it a draw.”

“You have to ask yourself, ‘to what end?'” he said.