The CIA’s Latin America Division has run many spies in Cuba, but Rolando Sarraff Trujillo was in a class all his own. (Family photo)

The CIA’s Latin America Division has run many spies in Cuba, but Rolando Sarraff Trujillo was in a class all his own.

From his perch as a cryptographer in Cuba’s Directorate of Intelligence, Sarraff was able to provide information that repeatedly helped the U.S. intelligence community crack encoded messages the Communist government was sending via shortwave radio.

This week, American officials said Sarraff’s information contributed to the FBI’s dismantling of three major spy networks in the United States. The last of them included a group of operatives known as the “Cuban Five,” who were convicted of espionage and made headlines again Wednesday when the three who were still in prison were freed as part of a dramatic spy swap that included Sarraff.

Former U.S. officials, while not speaking about Sarraff’s case directly, suggested his position in the Cuban intelligence apparatus would have made him an exceptional asset.

“You want the man who handles the communications,” said Gerald Komisar, a former CIA officer who was involved in Cuba operations in the 1990s and ran the Latin America Division. “He’s goning to have most of the secrets you want.”

Sarraff’s whereabouts remained a mystery Thursday. Vilma Sarraff, his sister, said that her parents, who live in Cuba, went to see their son Monday but that the family had not been informed about his release.

“We don’t know where he is,” she said in a phone interview from Spain, where she lives. “We don’t know if he’s in Cuba, if he’s in the United States. Our parents are looking everywhere.”

Rolando Sarraff was arrested in 1995 on espionage and other charges in Cuba and later was sentenced to 25 years in prison. In a blog they kept to draw attention to his case, his family recounted the sentencing.

“How is it possible that you sanctioned my son without showing one single piece of evidence?” Sarraff’s father asked.

The judge replied: “In Cuba you’re either with Fidel [Castro], or against. Your son said he is against.”

Although the family said there was no evidence to support a conviction, Sarraff had betrayed his native Cuba to help the United States, officials said. In addition to helping U.S. authorities identify the Cuban Five, Sarraff’s information allowed the FBI to arrest long-running spies at the State Department and Defense Intelligence Agency.

Robert Booth, a former diplomatic security agent with an extensive counterintelligence background, was deeply involved in flushing out the moles Sarraff helped identify at the State Department: Walter Kendall Myers and his wife, Gwendolyn Steingraber Myers.

Where U.S.-Cuba relations stand and what may change

In 2007, the FBI revealed to Booth that the National Security Agency had decrypted numerous Cuban shortwave radio transmissions. It appeared to him, he said in an interview, that the FBI had had the decrypted messages for years.

Though he said he never knew Sarraff had provided the crucial information, Booth became a beneficiary.

Based on the intercepts, Booth and FBI counterintelligence agents put together a matrix of personal characteristics of the mole. They assumed the spy was male, married, had a familiarity with Morse code, worked in the State Department and didn’t speak Spanish. He also was a civil servant employee, not a Foreign Service officer, which was crucial to narrowing the pool of suspects.

Within 30 days, Booth identified Walter Myers, who was arrested two years later by the FBI in a sophisticated counterintelligence operation. He was sentenced to life in prison in 2010; his wife received nearly seven years.

During the course of his two decades in captivity, Sarraff
was held in various prisons, including the Cuban government’s ­highest-security facility, Villa Marista, where he was at the time of his release.

Middle-of-the-night interrogations at the prison were common. “While being interrogated, the main technique was to morally crush you completely,” his family wrote in their blog.

They also posted letters they said Sarraff wrote from prison.

“My spirit is still strong, full of hope, and my honor intact,” Sarraff, now 51, wrote in 2012. “I confront this brutality and severe punishment with the utmost dignity, but without losing my tenderness, the sense of justice and my limited capacity to offer love.”

In the interview Thursday, Vilma Sarraff said her brother was a painter and a poet. Some of his work is featured on the blog. He is a “sweet person,” she said, adding, “He gives us strength.”

Komisar, the former CIA officer, said neither the United States nor Cuba can claim victory in their spy war. In the end, he said, it has been a draw.

“We had some successes,” he said. “They had some successes. We had some failures, and they had some failures.”

Julie Tate and Marlon Correa contributed to this report.