Cuba’s Vested Interest in Discrediting CIA Spy Rolando Sarraf Trujillo

Raul Castro

By Chris Simmons

In December, Rolando “Roly” Sarraf Trujillo was identified as the high-value American spy traded for three Cuba spies. In the weeks since, some Republicans, a self-serving former Cuban spy named Bill Gaede, and the Castro regime have joined forces to diminish the importance of Roly’s service to America.

The Republicans are motivated by their mistrust of President Obama. In contrast, Havana’s attacks are driven by the fear its global spy networks will realize they have been betrayed – not by Sarraf Trujillo — but rather by their Cuban masters. Over the last 20 years, a “perfect storm” of events came together to make Havana’s agent communications extremely vulnerable. This fact is well-known to the regime’s leadership, which has inexplicably done little to protect its spies in the field.

I – as well as anonymous intelligence sources in Washington – identified Roly as a Directorate of Intelligence officer assigned to an element known as Department M-XV (Agent Communications). With this placement and access, he would have been able to identify strengths and weaknesses in the High Frequency broadcasts (i.e., shortwave or “ham” radio) that Cuba has transmitted to its spies every day for decades. Sadly, the three-man CIA ring in which Roly served was compromised in 1994. Unable to escape the island like his colleagues, he was arrested and sentenced to 25 years in jail in 1995.

Thus, it’s no coincidence that in 1996, the FBI was able to start reading parts of the HF broadcasts from Havana to its largest spy ring in America. Known as the Wasp Network, this group of 43+ spies stretched from the Florida Keys to New York City and as far west as Louisiana. The Bureau’s code-breaking, while slow and imperfect, proved good enough to arrest 10 Wasp members in September 1998. During these arrests, the FBI acquired physical copies of the encryption and decryption software used by Cuba. It also seized nearly 1,000 encrypted computer disks with roughly 15,000 pages of material.

In August 2001, two more Wasps were arrested and their encryption seized. A month later, Cuban master-spy Ana Belen Montes was arrested at the Defense Intelligence Agency. A covert search of her apartment months earlier had discovered her encryption/decryption software program as well as numerous messages she failed to destroy. The Montes investigation originally began in 1998 as an “unidentified subject” (UNSUB) case. However, sufficient evidence didn’t come together to pinpoint a specific person until September 2000.

In May 2002, another Wasp was arrested and his cipher program recovered. Finally, in June 2009, Cuban spies Kendall and Gwen Myers were arrested. Technology dinosaurs, the couple were part of a handful of Cuban spies who stayed with Morse Code for roughly 30 years, long after almost everyone else had switched to encrypted voice messages.

Rolando Sarraf Trujillo allowed Washington to first gain insights into Havana’s spy networks two decades ago. This knowledge was then amplified by the practical experience the Bureau gained reading Wasp Network communications for over two years. This was followed, in turn, by another huge breakthrough — the subsequent arrests of more than 16 Cuban spies (most of whom took plea agreements and cooperated with the US). In these arrests, the US likely acquired over a dozen working copies of Cuba’s cipher software. Now, with Rolando Sarraf Trujillo presumably being debriefed somewhere in the United States, the US government is adding additional depth to its understanding of Havana’s spy communications.

These events, taken together, should strike terror in the heart of every Cuban spy. If we assume NSA recorded every HF broadcast Cuba sent over the last several decades, then the possibility exists that (at least theoretically), with enough time, people, and funding, Washington could eventually break every message Havana sent.

Even with its communications security in a 20-year freefall, Cuba continues transmitting daily HF broadcasts. So for all those disposable Cuban spies serving secretly throughout the US, I’d recommend you start sleeping with one eye open. Washington is closer to finding you than you ever imagined.