Cuba’s Vested Interest in Discrediting CIA Spy Rolando Sarraf Trujillo 9

Raul Castro

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.


  1. Thanks, Chris, for this explanation. From Roly´s jail term I infer that CIS never knew exactly what he have done.

  2. Pingback: The first 2015 Carnival of Latin America and the Caribbean | Fausta's Blog

    • Dear Prida, your question is simply silly. You have written enough about the issue in other posts. If you have something new, factual or logically justified, just shoot it, but if you keep on beating about the bush, the moderator of this blog is damn right by sparing us the reading. In this game, Simmons is on the side of the good arguments.

  3. GENTLEMEN, please, let´s get the facts straight for the readers:

    1.) There was no such “Montes investigation, originally began in 1998”. There was only an UNSUB (unidentified subject) investigation and such UNSUB investigation, soon thereafter 1998 stalled for lack of any findings whatsoever. That is a fact of history.

    2.) Even the following excerpt from Chris Simmons himself, as posted, on August 2014 corroborates this: “The FBI ran what was to become the Montes investigation for three years as an “Unidentified Subject” (UNSUB) case. In August 2000, the Defense Intelligence Agency became involved. DIA investigators Scott Carmichael and Karl James partnered with Counterintelligence analysts John Kavanagh and myself for our internal query. Working as a team, we conclusively identified Montes as the UNSUB in three weeks. Over the next several months, Scott Carmichael convinced the Bureau we were right and they opened the “Montes” investigation (excerpt from Chris Simmons August 2014 post)

    3.) Now as this article here purports: “However, sufficient evidence didn´t come together to pinpoint a specific person until September 2000”. This is also—although accurate in its chronology of date—it however, cannot be attributed to anything Rolando Sarraf Trujillo did or attributed to anything the FBI did. The Montes sudden discovery to being a Cuban spy after more than a decade—instead—is attributed to the fact there was, prior to the time of September 2000 when the DIA started the investigation, a full page newspaper article written by a private citizen in the Washington Times Newspaper, in Washington DC, (DC is the home location—vicinity of Alexandria, Virginia—of the U.S. intelligence APPARATUS) published on June 28, 2000, by a private citizen´s at his sole expense. The newspaper article (even designated as an advertisement) although it alleged erroneously the all-knowing U.S. intelligence APPARATUS knew well the big risk factor Cuba represented for the United States at a time. Notwithstanding, in contrast, the top intelligence officer, Ana Belen Montes in charge of the country Cuba at the nerve center of U.S. Intelligence was making the opposite intelligence reports and recommendations to the White House by stating Cuba was not a risk factor for the United States. And of course, that became the official stance of the Intelligence APPARATUS of the U.S. It was a TOTALLY ERRONEUS position, until such newspaper article was published by this private citizen, wherein it became so obvious to this private citizen that Cuba was a risk factor that he actually opined the United States Intelligence APPARATUS knew Cuba was a big risk for this nation. Amazing, this situation put a bright spotlight on the U.S. intelligence community APPARATUS because it actually was recommending to the White House that Cuba was not a risk factor and in contrast the newspaper article assumed the U.S. intelligence APPARATUS of the United States must have known well what a big risk factor Cuba was, yet, without this private citizen actually knowing the U.S. intelligence APPARATUS was in reality in the dark by recommending Cuba was not a risk factor to this country. WHAT A TOTAL JOKE! But, now, everyone wants to take credit for Ana Belén Montes discovery and capture. Monday morning quarter-backing.

    4.) Let´s look at the chronology:

    a.) June 28, 2000: The newspaper article is published on June 28, 2000.

    b.) August 2000: All of a sudden, after more than 20 years of uninterrupted spying activity by Ana Belén Montes, someone got the idea of starting to investigate Ana Belén Montes on August 2000 right 32 days after the newspaper article got published and with July fourth holidays in between, so less days even. That´s when all the so call spy catchers came in on the command of the DIA, not their own initiative, as the private citizen had the initiative to state Cuba was risk factor to the United States. Anybody reading the private citizen´s self-funded newspaper article would have followed-up on the allegations made there. That is call pointing the entire U.S. APPARATUS, with working in it—in the right direction. How easy, right? That´s as easy as all the contentions flying around here about Ana Belén Montes when no one had any patriotic equity, except this private citizen. Fact of life.

    c.) And never forget, there was only one reason why she began to be investigated: She had recommended Cuba was no longer a risk factor to the United States and the newspaper article stated and pointed, with succinct proof, Cuba was in fact a risk for the U.S., at that time. Next morning, questions would started to pop-up, because the evidence presented by this private citizen in this newspaper article was sufficiently good to get—even a 15 year old—thinking: Why is Ana Belén Montes recommending Cuba not to be a risk, when after reading the private citizen´s, self-funded, full-page newspaper article and without such private person working for the U.S. intelligence community, it pointed very factual proof to cause anyone—with half a brain—to start thinking along the lines: Cuba is a risk. Oh! You know, maybe Montes is the UNSUB. Gotcha as they say! Most common crimes are solved from tips from strangers or persons not directly involved. This is no different so spare the readers of all these accommodating stories and newfound careers in spying as if it were all true, when it is not. Ana Belén Montes read the newspaper article and she became very nervous about it because it pointed specifically to the U.S. intelligence community to be knowing of the fact that Cuba was a risk factor to the United States, when actually she had been formulated opposite recommendations to the White House in her reports. Even Bill Clinton admitted how blind sighted they were on this issue.

    d.) The most unfortunate part of this, is, “someone”, yes, an “unknown someone” with what must be a lot of power inside the halls of U.S. government, thereafter, came after this private citizen with a vengeance and made the critical mistake of using the citizen´s modified last name, as the private citizen had purposely put in his signature of the newspaper article, thinking that in the event “a someone” came after him—as it did happen later—using that modified last name, he could quickly identify the source of potential undue aggression for writing the newspaper article. That´s exactly what happened when an “unknown someone” came after this private citizen using the modified last name in the style of a federal indictment against this private citizen, the same modified last name appearing in the signature of the newspaper article and only such modified last name had been used by this private citizen in that one instance.

    But as life has many times has it, all the related to “someone” whose personal interests intersected and came after this private citizen are today suffering one hell of a lot more, while the private citizen is fine. The others related are either in prison, some suffered massive strokes and in questionable health, some disgraced out of their legal prosecution careers accused by the FBI and federal judges of being corrupt, another dead as shot by the FBI and left to bleed (not normally the procedure when someone is already down disabled) and another, suddenly, out of circulation of major power after so many years. Go figure it out. Mind control is not for the meek or for those who play spy games. It´s game ball to right and justice. It´s Kudos for this private citizen. His newspaper article was right on the money, while the entire U.S. INTELLIGENCE APPARATUS had been out to lunch on Ana Belén Montes and not just for one year for decades. But the private citizen thought they weren’t out to lunch, giving the U.S. intelligence community more credit than to himself who actually pointed them in the right direction, without knowing.

    This is a different time, this is a different circumstance and the U.S. and Cuba should start collaborative joint intelligence efforts soon. As we say, here in the U.S., birds of a feather flock together. Intelligence sharing may have already happened a while back between Cuba and the U.S., on very specific instances. Perhaps a match of joint abilities–English and Spanish–made in heaven. There are bigger foes at this time. Anyone can figure that out. Peace and collaboration are the orders of the day. Nuff said.

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