Agent at Center of Spy Swap Was Cuban Crypto Expert

The mysterious Cuban spy at the center of the rapprochement between Havana and Washington now has a name: Rolando Sarraff Trujillo.

A first lieutenant in the Cuban Directorate of Intelligence and an expert in cryptography, Sarraff spent nearly 20 years behind bars in Cuba for his espionage activity on behalf of the United States. He was included in the swap between Washington and Havana that brought imprisoned American contractor Alan Gross back to the United States in exchange for the remaining three members of the so-called “Cuban Five” spy ring, which attempted to infiltrate the Cuban expat community in Florida. The trade helped seal a broader agreement between Washington and Havana to normalize diplomatic relations.

His identity was first reported by Newsweek and confirmed by the New York Times.

In announcing the spy swap, American officials said that Sarraff — who in official statements has remained anonymous — helped capture several Cuban agents operating on American soil, including the Defense Intelligence Agency official Ana Montes and the State Department official Walter Kendall Myers and his wife, Gwendolyn.

The revelation of Sarraff’s identity has now shed some light on his possible role in bringing down Montes and Myers, both of whom were major Cuban intelligence assets in the U.S. government with wide-ranging access to classified material that they fed to Havana. Both agents used shortwave radios to receive encrypted messages from their handlers, and it has long been speculated that the interception of such messages may have helped bring the agents to the attention of U.S. authorities.

By virtue of his access to Cuban cryptologic systems, Sarraff was positioned to help the United States bring down Havana’s networks inside the United States. “When Roly was providing information, he was giving us insights about where there were weaknesses in the Cuban encryption system,” Chris Simmons, the former head of a Cuban counterintelligence unit at the DIA, told the Times.

Montes, for example, would tune a Sony shortwave radio hidden in her Cleveland Park apartment to AM frequency 7887 to receive messages from her handlers. A female voice would bark “Atencion! Atencion!” and a string of numbers would follow that comprised the raw material of an encrypted message. Myers used similar techniques, and they helped the spies evade U.S. authorities for years.

Though his exact role in the operations to bring down Montes and Myers remains unknown, his work on cryptologic systems and statements by U.S. officials that he helped bring down these agents, appears to lend credence that the interception of encrypted shortwave communications contributed to the arrest of Havana’s spies.

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