Wilderness of Mirrors: Cuban Edition

As an old counterintelligence hand, I can attest that trying to explain the nuts and bolts of CI operations to normals, especially when Russians and their friends are involved, can prove an insurmountable chore. When you get deeply involved in a complex CI operation, compass points become distorted and “ground truth” may get murky indeed, as I elaborated in Wilderness of Mirrors, about a knotty and mysterious Russian op against a NATO country. That is a loaded phrase among counterspies, as I explained at the time:

One of the best things about working in counterintelligence, if you’re comfy with imprecision, is that it’s all about mysteries (one of the worst things is that it can make you crazy), some so vexing and intellectually challenging that they elude agreed-upon solutions for decades, in some cases in perpetuity. James Angleton, the poet-turned-counterspy who became CIA’s genius/flake chief of CI for much of the Cold War, referred to this experience as “the wilderness of mirrors,” which captures the enduring mystery of never quite grasping up from down in a case, or knowing who’s really running the show, no matter how closely you look at it (the memorable phrase also happens to be the title of the best book about the CIA’s Angleton experience).

This has come to the fore again in light of President Obama’s recent opening to Cuba, part of which was a spy-trade between DC and Havana. For all their problems, the Cuban regime remains a heavy hitter in the global espionage game, having run rings around U.S. intelligence for decades, as I’ve explained in detail. Although most of the CI wins over the decades have been in Havana’s column, an exception was Rolando Sarraf Trujillo, a Cuban intelligence officer who was jailed by Cuba in 1995 for passing important secrets to the United States. Despite the fact that his release was part of Obama’s deal with Havana, Sarraf’s family says they have not heard from him, his supposed release from Castro’s jails notwithstanding, leading to all kinds of questions.

To add to the mystery, a notorious Cuban agent has thrown fuel on the fire by suggesting that Sarraf was bogus from the start, a controlled source under Havana control. If you like counterspy mysteries, this one has it all: implausible cover stories, legends worse than pulp fiction, and competing moles. According to Bill Gaede, an Argentinian mystery man who has at times worked for the intelligence services of not just Castro’s Cuba but the Soviet Union, East Germany, Communist China and revolutionary Iran — as well as, maybe, the United States — Sarraf was a controlled source the entire time and therefore merits none of this American concern.

I trust Gaede as far as I can throw him, as they say, but Havana’s skilled intelligence apparatus retains an impressive ability to influence politics in the United States, their Main Enemy, so anything is possible. Was Sarraf the jewel in the crown who gave CIA several Cuban agents on a platter — most importantly DIA’s Ana Belen Montes, an epic traitor — or was he yet another in a long line of Havana dangles who played los gringos for a fool?

Perhaps this is what Sarraf is currently being debriefed about at such length by U.S. officials that his family has not had a single word from him, some three weeks after he was sprung from a Cuban jail cell. Time will tell, as it always does. If Sarraf passed Cuban crypto — to any journalists reading this, take this as a hint — to the U.S. then he was no dangle, rather a bona fide source: the exception who proved the rule. If not, assume this was under Havana’s control from the start.

Welcome to the Wilderness of Mirrors ….

 

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Counterintelligence Espionage USG