WASHINGTON (TIP): He was, in many ways, a perfect spy — a man so important to Cuba’s intelligence apparatus that the information he gave to the Central Intelligence Agency 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 the swap for three Cuban spies imprisoned in the United States that President Obama announced Wednesday.

Mr Obama did not give Mr Sarraff’s name, but several current and former American officials identified him and discussed some of the information he gave to the CIA while burrowed deep inside Cuba’s Directorate of Intelligence.

Mr 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 and years after Cuba ceased to be a serious threat to the United States. The story — at this point — remains just a sketchy outline, with Mr Sarraff hidden from public view and his work for the CIA still classified.
The spy games between the two countries lost their urgency after the fall of the Soviet Union, but the spies have stuck to their roles for more than two decades: pilfering documents, breaking codes and enticing government officials to betray their countries. “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,” said Jerry Komisar, who ran C.I.A. clandestine operations in Cuba during the 1990s.

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.

In retrospect, Mr Komisar said, there was little need for American intelligence services to devote so much attention to Cuba — 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.

After decades of cloak-and-dagger activities between the two countries, he said, it turned out to be “a draw.”

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

Before he was arrested in November 1995, Mr Sarraff 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. According to members of his family, he had studied journalism at the University of Havana and had the rank of first lieutenant at the intelligence directorate.

It is not clear when Mr Sarraff, now 51, began working for the CIA Chris Simmons, who was the chief of a Cuban counterintelligence unit for the

Defense Intelligence Agency from 1996 to 2004, said that he worked with another man — Jose Cohen, one of Mr Sarraff’s childhood friends — to pass encryption information to the C.I.A. that led to the arrest of a number of Cuban agents operating in the United States.

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

Cuban authorities arrested Mr Sarraff in November 1995 and put him on trial for espionage, revealing state secrets and other acts against state security. According to one senior American official, the Cuban government learned of his plans to defect when he was on assignment in a third country and recalled him to Cuba and put him in jail.

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

He was sentenced to 25 years in prison. Mr Simmons, the former D.I.A. officer, said he believed that the reason Mr Sarraff was not executed was because his parents were officials in the Cuban government. “He has always maintained his innocence” his sister, Vilma Sarraff, said by telephone from Spain. She said that Mr Sarraff’s daughter was 7 when he was arrested.