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.

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Spy Wars: A Wilderness of Mirrors in U.S.-Cuba Swap 2

Jose Cohen, pictured at Little Havana’s Versailles Restaurant in 2000 (Al Diaz, Miami Herald Staff)

Jose Cohen, pictured at Little Havana’s Versailles Restaurant in 2000 (Al Diaz, Miami Herald Staff)

By Glenn Garvin, Juan O. Tamayo and Patricia Mazzei

ggarvin@MiamiHerald.com

More than two weeks have passed since the White House announced that it had traded three imprisoned Cuban intelligence officers — including one convicted of conspiracy to murder — for a super spy held in a Havana prison whom President Barack Obama labeled “one of the most important intelligence agents that the United States has ever had in Cuba.”

But since the president’s announcement, there’s been only silence. Nothing more has been said of the spy or his accomplishments. Of the people released from prison as part of the deal between Washington and Havana, the three Cuban spies and U.S. Agency for International Development contractor Alan Gross have all appeared on television to talk exultantly about their release.

Yet Washington’s master spy has remained anonymous and incommunicado. The only man who seems to fit the handful of clues the White House provided about the spy’s identity — former Cuban Interior Ministry Lt. Rolando Sarraff, jailed since his arrest in 1995 — has disappeared from the Havana prison where he was being held, and his family members say they’ve neither heard from him nor been told his whereabouts.

The Obama administration won’t confirm Sarraff’s name, much less why he could be out of reach.

But a man who claims he is a former member of Sarraff’s spy ring speculates there’s a good reason for Sarraff’s disappearance: that Sarraff was a fake, feeding the CIA false or trivial information as part of a Cuban scheme to disrupt U.S. intelligence.

“They were acting on behalf of Fidel Castro,” insists Bill Gaede, an Argentine engineer who says he carried information to the CIA from Sarraff and other Cuban intelligence officers. “They weren’t genuine. They were full of caca.”

What’s more, Gaede contends, the CIA and FBI suspected that Sarraff was a fake — a “dangle,” in intelligence parlance — right from the start, and never believed anything the ring of putative spies passed along. U.S. officials, he says, are calling him a valuable agent now only to make the Gross-for-Cuban-spies swap more palatable to U.S. conservatives. “It’s just public relations,” sniffs Gaede.

AT CUBA’S SERVICE

But Gaede’s claim is hotly disputed by another member of the spy ring — Jose Cohen, also a former lieutenant in the Cuban Interior Ministry, who defected from Cuba in 1994. “Bill Gaede is not a [credible] source. He was an enemy of the United States. He’s at Cuba’s service,” says Cohen, now living in southwest Miami-Dade, where he’s a highly successful Amway salesman.

“I think what Bill is looking for is publicity. … He’s mocking the press, he’s mocking the government.”

Article continues here: Spy Wars

 

 

FBI: Cuban Intelligence Aggressively Recruiting Leftist American Academics as Spies, Influence Agents 10

Bill Gertz is a national security columnist for The Washington Times and senior editor at The Washington Free Beacon

Bill Gertz is a national security columnist for The Washington Times and senior editor at The Washington Free Beacon

Sexual entrapment a common tactic

By Bill Gertz, Washington Free Beacon

Cuba’s communist-led intelligence services are aggressively recruiting leftist American academics and university professors as spies and influence agents, according to an internal FBI report published this week.

Cuban intelligence services “have perfected the work of placing agents, that includes aggressively targeting U.S. universities under the assumption that a percentage of students will eventually move on to positions within the U.S. government that can provide access to information of use to the [Cuban intelligence service],” the five-page unclassified FBI report says. It notes that the Cubans “devote a significant amount of resources to targeting and exploiting U.S. academia.”

“Academia has been and remains a key target of foreign intelligence services, including the [Cuban intelligence service],” the report concludes.

One recruitment method used by the Cubans is to appeal to American leftists’ ideology. “For instance, someone who is allied with communist or leftist ideology may assist the [Cuban intelligence service] because of his/her personal beliefs,” the FBI report, dated Sept. 2, said.

Others are offered lucrative business deals in Cuba in a future post-U.S. embargo environment, and are treated to extravagant, all-expense paid visits to the island.

Coercive tactics used by the Cubans include exploiting personal weaknesses and sexual entrapment, usually during visits to Cuba.

The Cubans “will actively exploit visitors to the island” and U.S. academics are targeted by a special department of the spy agency.

“This department is supported by all of the counterintelligence resources the government of Cuba can marshal on the island,” the report said. “Intelligence officers will come into contact with the academic travelers. They will stay in the same accommodations and participate in the activities arranged for the travelers. This clearly provides an opportunity to identify targets.”

In addition to collecting information and secrets, Cuban spies employ “influence operations,” the FBI said.

“The objective of these activities can range from portraying a specific image, usually positive, to attempting to sway policymakers into particular courses of action,” the report said.

Additionally, Cuban intelligence seeks to plant disinformation or propaganda through its influence agents, and can task recruits to actively disseminate the data. Once recruited, many of the agents are directed to entering fields that will provide greater information access in the future, mainly within the U.S. government and intelligence community.

Article continues here:  Cuban Targeting 

Latell’s Latest Assessment Reveals Why Analysts Should Not Perform Counterintelligence 7

Ana Belen Montes

Ana Belen Montes

By Chris Simmons

Writing first in the Cuba Transition Project and then the Miami Herald, Dr Brian Latell recently energized readers with his feature, New revelations about Cuban spy Ana Montes

I, however, was greatly disappointed with the article. To start, he sensationalized several trivial issues and recycled old news stories (yes, she was a “true believer”  volunteer and yes, she was brought to the Cubans by talent-spotting agent Marta Rita Velazquez). None of this information is new.

However, he then misinterprets several key facts due to a lack of understanding regarding the field of counterintelligence, in layman’s terms – spy-catching.

For example, Latell claims that Montes met with her handlers “initially in New York, and later at her request in the Washington area…” Any Counterintelligence officer knows Havana would never consider running a penetration of the US government from 225 miles away. Having an agent or officer travel that distance once or twice a month for an extended period would be a huge risk to the security of the operation. Montes may have “asked” the Cubans for a DC-based spy handler, but the reality is she was going to be transferred to a local operative regardless of her wants and wishes.

More dangerous (and out of context) is his claim that during her interrogations, she was told that investigators “had information from a senior official in the Cuban intelligence service concerning a Cuban penetration agent that implicated Montes.” While that may be – in part – what the Pentagon document said, rare are the instances wherein an interrogator would truthfully tell a suspect they were betrayed by a colleague. That said, it is a common ploy to lie to a suspect and tell him/her their own people gave them up. This is what occurred with Montes.

Another major error is his wildly speculative and erroneous statement: “Did she work with other American spies? The report is ambiguous; it states that after the terrorist attacks on September 11, 2001 pressure intensified to arrest Montes. The FBI preferred to wait, however, in order “to monitor Montes’s activities with the prospect that she may have eventually led the FBI to others in the Cuban spy network.”

The FBI wasn’t the only organization that preferred to wait – those of us in the Defense Intelligence Agency wanted to continue building the case as well. The “others in the Cuban spy network” weren’t part of some mysterious massive spy ring, but rather the compañeros she’d served during her espionage career.

Dr Latell is an exceptional analyst in his field. That said, Counterintelligence is a discipline unto itself, rendering any analytic generalist a poor job fit for analyzing spy services. Counterintelligence analysis is – and will always be — best performed by badge-carrying Special Agents skilled in investigations, operations, and collections.