The Mysterious Cuban Spy at the Center of Obama’s Havana Rapprochement

Sitting alone in her Cleveland Park apartment, Ana Montes, the Defense Intelligence Agency’s top Cuban analyst in the 1990s and a spy for the communist island, tuned her Sony radio to AM frequency 7887 kHz and received her instructions from Havana. “Atencion! Atencion!” a female voice would announce, followed by streams of numbers that were the raw materials of an encrypted message, according to a Washington Post profile of the spy. It took a fanatic investigator tipped off by the vaguest of information — that the Cuban government had an unnamed, centrally placed spy that stored her secrets on a Toshiba laptop — to finally bring her down.

The downfall of Montes — one of the most productive spies to have ever betrayed the United States — now has a new historical wrinkle: It turns out the United States secretly had a man of its own in Havana, the likely source of the Toshiba tip that brought her down.

In announcing Wednesday a normalization of relations between their two countries, President Barack Obama and his Cuban counterpart, Raul Castro, sealed the deal with an exchange of spies. Under the terms of the burgeoning rapprochement, Cuba will release that spy, a traitor who has languished in his country’s jails for nearly 20 years. In exchange, the United States will release the remaining three members of the so-called Cuban Five spy ring.

Little is known about the Cuban who is now headed toward what will likely be a comfortable retirement in the United States. But what little U.S. officials disclosed on Wednesday make him one of the United States’ most important Cold War spies. “Information provided by this person was instrumental in the identification and disruption of several Cuban intelligence operatives in the United States and ultimately led to a series of successful federal espionage prosecutions,” Brian P. Hale, a spokesman for the Office of the Director of National Intelligence, said in a statement, a highly unusual acknowledgement of a U.S. intelligence asset’s contributions.

Among the Cuban spies he helped take down were Montes; the former Department of State official Walter Kendall Myers and his wife, Gwendolyn, and members of the so-called “Wasp Network,” which infiltrated the Cuban exile community. Taken together, Montes and Myers are probably the most damaging turncoats in the history of the U.S. intelligence community, rivaled only by Navy Warrant Officer John A. Walker, who compromised an immense portion of American encryption systems.

Before being exposed as a spy, Myers was a full-fledged member of the American aristocracy, as portrayed in Toby Harnden’s wonderful profile of the man for Washingtonian. His great-grandfather was Alexander Graham Bell, the inventor of the telephone, and he learned how to sail at his family’s estate in Newfoundland. His grandfather was Gilbert Grosvenor, who edited National Geographic for 55 years.

Recruited as a Cuban spy in the late 1970s, Myers eventually rose to become a senior analyst at the State Department’s Bureau of Intelligence and Research, with a focus on Western Europe. With a top secret clearance, he is believed, together with his wife, to have fed the Cuban a huge trove of classified intelligence reports covering all corners of the globe.

Myers is currently serving life in prison, and if it weren’t for the Cuban the White House traded for, the former State Department official might still be sailing aboard his beloved yacht with his wife. Indeed, it has been suggested in FBI affidavits that the Myers used a similar radio system to Montes and that their arrest came as a result of American spies breaking Cuban codes, which may point toward the involvement of the spy in Havana.

But Montes was arguably the bigger prize for the anonymous Cuban. As a GS-14, the civilian equivalent of a lieutenant colonel, at the Defense Intelligence Agency — the principal U.S. agency responsible for producing military intelligence — Montes would memorize reams of highly classified reports and return to her apartment and transcribe them on a Toshiba laptop. She then passed the information to her Cuban handlers through a combination of dead drops and clandestine meetings.

But previous accounts of how Montes landed on the FBI’s radar as a possible source have so far been maddeningly vague and have centered on her purchase of a Toshiba laptop. We now know where that information probably came from: the anonymous man en route or already back in the United States from a Cuban jail.

Official White House Photo by Pete Souza