As Normalization Effort Continues, Cuban Spy Broadcasts Continue…… 3

numbers stationsAs expelled spy-diplomats Josefina Vidal and Gustavo Machin push for greater US concessions, their spy colleagues continue to go “old school” in targeting the US…..

Recent Cuban “Numbers Stations” broadcasts from Havana to the regime’s spies abroad:

February 9th

February 8th

February 6th

January 20th

January 16th

 

Cuban National Released in White House Deal with Havana Now Back in the U.S. 3

Rolando Sarraff in 1996, the year he was imprisoned by the Cuban government (L)and more recently (R). Sarraff was sentenced to jail by the Cuban government for spying for the United States. He was freed in a prisoner exchange with the United States last month. (Family photo)

Rolando Sarraff in 1996, the year he was imprisoned by the Cuban government (L) and more recently (R). Sarraff was sentenced to jail by the Cuban government for spying for the United States. He was freed in a prisoner exchange with the United States last month. (Family photo)

By Missy Ryan, Washington Post

A Cuban national imprisoned for nearly two decades as an American spy is now in the United States, his family said Tuesday, the first confirmation of the former U.S. agent’s whereabouts since he was released in last month’s deal to overhaul ties with Cuba.

Rolando Sarraff, a cryptographer with Cuba’s Directorate of Intelligence, was imprisoned in 1995 on suspicion that he was passing secrets to the United States. Information provided by Sarraff helped U.S. officials dismantle networks of Cuban spies in the United States, one illustration of the mutual hostility that characterized U.S. dealings with Communist Cuba for more than 50 years.

The White House secured Sarraff’s release last month as part of President Obama’s sweeping agreement to thaw U.S. ties with the island nation. The deal also included the return of an American aid contractor held by Havana and the release of three Cuban intelligence agents imprisoned in the United States.

But since the deal was announced Dec. 17, Obama administration officials have declined to confirm whether Sarraff was taken to the United States, or whether he was in U.S. government custody somewhere else. For weeks, family members in Cuba, Spain and the United States said they had not been informed by either the U.S. or the Cuban government about his whereabouts.

This week, his sister, who lives in Spain, said she finally heard from her brother. “He’s well, and he’s in the U.S.,” Vilma Sarraff told The Washington Post. She declined to give details.

The Sarraff family’s confirmation of the former agent’s whereabouts were first reported Tuesday by the Associated Press

Missy Ryan writes about the Pentagon, military issues, and national security for The Washington Post.

 

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.

Cuban Relatives of U.S. Spy in Dark After News of Release 3

Vilma Sarraff Trujillo

Vilma Sarraff Trujillo

By Phil Stewart and David Adams

(Reuters) – His release from a Cuban prison has been as cloak-and-dagger as his spying career ever was.

Not even the family of Rolando Sarraff Trujillo appears to know what has happened to the Cuban man believed by some to be the U.S. informant secretly freed in a prisoner swap between Cuba and the United States that was announced on Wednesday.

“All I can say is that … my brother has disappeared,” his sister, Vilma Sarraff Trujillo, said by telephone from Spain on Friday, noting that Sarraff’s family in Cuba has not heard from him in days and has not been able to pry any information from Cuban officials. “We don’t know anything.”

Unlike the televised homecoming of Alan Gross, the former U.S. aid worker who became a household name in diplomatic circles, the United States and Cuba have declined to publicly disclose the identity of the freed spy.

The White House and U.S. intelligence agencies on Friday declined to confirm or deny media reports that Sarraff, who had been in a Cuban prison since 1995, was indeed the freed spy.

There’s good reason why he might be out of sight.

“He’s probably in some very quiet place being debriefed. They want to know exactly what happened,” a former senior U.S. intelligence official said. “It would be a standard thing.”

The U.S. Director of National Intelligence’s office credited the unnamed freed spy as having been “instrumental in the identification and disruption of several Cuban intelligence operatives in the United States.”

Chris Simmons, a former senior counter-intelligence official at the Defense Intelligence Agency, described Sarraff – familiarly known as “Roly” – as a cryptographer who worked for Cuba’s director of intelligence, citing accounts from Cuban defectors.

He said Cuba communicated with its spies through short-wave radio, using groups of numbers to send coded messages. Sarraff would have been able to help the United States break that code.

“Roly was arrested in 1995. Almost immediately the FBI can read Cuban communications,” Simmons said, saying he believed Sarraff was the one released based on the U.S. government’s description of the spy’s work.

Feature continues here:  Cuban Relatives

U.S. Spy in Havana Exposed American Moles 4

An image provided by Cuba shows President Castro, right, Wednesday with members of the ‘Cuban Five’ who were released in a U.S. prisoner swap.  European Pressphoto Agency

An image provided by Cuba shows President Castro, right, Wednesday with members of the ‘Cuban Five’ who were released in a U.S. prisoner swap. European Pressphoto Agency

Intelligence Officer Whom Obama Singled Out for Prisoner Exchange Helped Convict Agents for Cuba in Washington

By Felicia Schwartz , The Wall Street Journal, felicia.schwartz@wsj.com

WASHINGTON—In announcing the prisoner exchange that set up a momentous shift in U.S.-Cuba relations, the Obama administration this week made an unusual disclosure, revealing the existence of a key intelligence agent, and detailing specific cases he helped to crack.

The U.S. informant, identified on Thursday as Rolando Sarraff Trujillo by those familiar with his role, had been convicted and imprisoned in Cuba for nearly 20 years for helping Washington. He was recently freed and flown to the U.S.

Undisclosed before this week was Mr. Sarraff’s secret role as an American operative in Cuba who provided critical information that prompted the 1998 arrests of a group of spies known as the “Cuban Five,” intelligence operatives sent to infiltrate U.S. groups opposed to the regime in Havana.

In remarks at the White House, Mr. Obama, without naming Mr. Sarraff, said that he was “one of the most important intelligence agents the United States has ever had in Cuba.”

In a separate set of prominent U.S. espionage cases, Mr. Sarraff also provided information leading to the detection and conviction between 2001 and 2009 of a group of American government officials for funneling information to Havana, the officials said.

The Americans included the Defense Intelligence Agency’s top Cuba analyst at the time, Ana Belén Montes, and former State Department official Walter Kendall Myers and his wife, Gwendolyn Myers, officials said.

All are still serving prison sentences.

In a speech Wednesday, Cuban President Raúl Castro didn’t name Mr. Sarraff but said he was “a spy of Cuban origin.” He has been widely identified as a former Cuban intelligence officer imprisoned in Cuba on espionage charges since 1995.

Mr. Sarraff was a cryptographer in Cuba’s intelligence service, said Chris Simmons, who headed a unit on Cuba for the Defense Intelligence Agency from 1997 to 2004.

Mr. Sarraff was arrested in Cuba in 1995, was convicted and sentenced to 25 years in prison in 1996. He had provided information about the codes used by Cuban spies in the U.S. to communicate with Havana, Mr. Simmons said. Cuba typically used shortwave radio to communicate with agents in the U.S., he said.

U.S. officials used the information to decipher communications and identify spies, even long after he was arrested. “Once you have the insight, if you’ve got enough time, money and resources, you can go back and look at everyone,” Mr. Simmons said.

Feature continues here: Roly

 

Crucial Spy in Cuba Paid a Heavy Cold War Price 1

Rolando Sarraff Trujillo, in a photo released by his family.

Rolando Sarraff Trujillo, in a photo released by his family.

By Mark Mazzetti, Michael S. Schmidt and Frances Robles, New York Times

WASHINGTON — He was, in many ways, a perfect spy — a man so important to Cuba’s intelligence apparatus that the information he gave to the Central Intelligence Agency paid dividends long after Cuban authorities arrested him and threw him in prison for nearly two decades.

Rolando Sarraff Trujillo has now been released from prison and flown out of Cuba as part of the swap for three Cuban spies imprisoned in the United States that President Obama announced Wednesday.

Mr. Obama did not give Mr. Sarraff’s name, but several current and former American officials identified him and discussed some of the information he gave to the C.I.A. while burrowed deep inside Cuba’s Directorate of Intelligence.

Mr. Sarraff’s story is a chapter in a spy vs. spy drama between theUnited States andCuba that played on long after the end of the Cold War and years afterCuba ceased to be a serious threat to theUnited States. The story — at this point — remains just a sketchy outline, with Mr. Sarraff hidden from public view and his work for the C.I.A. still classified.

The spy games between the two countries lost their urgency after the fall of the Soviet Union, but the spies have stuck to their roles for more than two decades: pilfering documents, breaking codes and enticing government officials to betray their countries. “There were a number of people in the Cuban government who were valuable to the U.S., just as there were a number of people in the U.S. government who were helpful to the Cubans,” said Jerry Komisar, who ran C.I.A. clandestine operations in Cuba during the 1990s.

With Wednesday’s exchange of imprisoned spies and the leaders of the United States and Cuba talking in a substantive way for the first time in more than 50 years, some people who were part of the spy games between the two countries now wonder just how much it was worth it.

In retrospect, Mr. Komisar said, there was little need for American intelligence services to devote so much attention to Cuba — a country with a decrepit military that he said posed no strategic threat to the United States since the Soviet Union pulled its missiles off the island in 1962.

Continue reading the main story

 

The American Spy Traded in the U.S.-Cuba Diplomatic Breakthrough 5

People cheer for the "Cuban Five" while holding a poster of the five Cuban intelligent agents, in Havana December 17, 2014. After 18 months of secret talks facilitated by the Vatican and Canada, Obama and Cuban President Raul Castro agreed by phone on Tuesday on a prisoner exchange and the opening of embassies in each other's countries. Obama said the moves were made possible by Havana's release of American Alan Gross, 65, who had been imprisoned in Cuba for five years. Cuba is also releasing an intelligence agent who spied for the United States and was held for nearly 20 years, and the United States in return freed three Cuban intelligence agents held in the United States. The poster reads "Freedom now !". REUTERS

People cheer for the “Cuban Five” while holding a poster of the five Cuban intelligent agents, in Havana December 17, 2014. After 18 months of secret talks facilitated by the Vatican and Canada, Obama and Cuban President Raul Castro agreed by phone on Tuesday on a prisoner exchange and the opening of embassies in each other’s countries. Obama said the moves were made possible by Havana’s release of American Alan Gross, 65, who had been imprisoned in Cuba for five years. Cuba is also releasing an intelligence agent who spied for the United States and was held for nearly 20 years, and the United States in return freed three Cuban intelligence agents held in the United States. The poster reads “Freedom now !”. REUTERS

By Jeff Stein, Newsweek

The unidentified United States spy being swapped as part of a diplomatic breakthrough between the U.S. and Cuba is almost certainly a former cryptographer in Cuba’s Directorate of Intelligence who worked secretly for the CIA until he was arrested on espionage charges in the mid-1990s, according to a former U.S. intelligence officer and other sources.

Rolando “Roly” Sarraf Trujillo was “an expert on cryptography for the Cuban Ministry of Interior who was arrested in 1995 and sentenced to 25 years in jail,” says Chris Simmons, a former Defense Intelligence Agency specialist on Cuba.

“I know of all the Cubans on the list of people in jail and he is the only one who fits the description” of the unnamed asset who U.S. officials said was part of the deal to reestablish diplomatic relations between the two former Cold War adversaries.  The agent, U.S. officials said, was swapped for the remaining three members of the so-called “Cuban Five” spy ring, a group of operatives arrested in Florida on espionage charges in 1998. Another element of the agreement, which ended a decades-long feud, was Cuba’s decision to free Alan Gross, a U.S. Agency for International Development contractor imprisoned on the island since 2009, on charges of trying to subvert the state.

“I am 99.9 percent sure that Roly is the guy…” Simmons said in a telephone interview  “He’s the only one who fits the description” of the unidentified U.S. intelligence asset being released by Cuba, he added.

In a speech on Wednesday, Cuban President Raul Castro said that a spy of “Cuban origin” was being released. And the Miami Herald’s Spanish-language edition also reported that its sources believe that Sarraff Trujillo was that man.

Neither Cuba nor the Obama administration’s Director of National Intelligence (DNI) would identify the spy in question or comment on Sarraf Trujillo.

DNI spokesman Brian P. Hale said in a prepared statement that the asset being released spent 20 years in a Cuban prison for his work for the United States. Many of the details of his cooperation are classified, but Hale said he 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.”

Indeed, according to Hale, the spy “provided the information that led to the identification and conviction of Defense Intelligence Agency (DIA) senior analyst Ana Belen Montes; former Department of State official Walter Kendall Myers and his spouse Gwendolyn Myers; and members of the Red Avispa network, or ‘Wasp Network,’ in Florida, which included members of the so-called Cuban Five.”

Simmons said that, “just as a matter of elimination,” it’s Sarraf Trujillo.

Feature continues here:  Spy Swap

 

Numbers Stations: A Bad Day to be a Cuban Spy 1

SWLingPost-Spy-Numbers-Station

 

 

 

 

 

 

 

 

 

By Thomas, The SWLing Post

While band scanning last Sunday (September 8, 2014) I stumbled upon the Cuban numbers station HM01 on 11,530 kHz at 17:30 UTC.

It’s always intriguing to hear shortwave numbers stations, but I prefer those that stick to pure vocal number strings; HM01 has numbers with digital bursts between number sets, which is a more fatiguing listening experience.  Nonetheless, I kept it playing in the background as I tooled around the radio room Sunday afternoon, putting away supplies from my recent three week road trip.

Several times during the HM01 broadcast, I heard the audio (not the AM carrier) drop in the middle of numbers sets and digital bursts. This isn’t the first time I’ve heard hiccups on HM01 (see this post from last year, for example), so I wasn’t terribly surprised. Then, close to the top of the hour, HM01 audio dropped for a minute or so, then switched back to five-number sets with no digital bursts between; though I wasn’t copying the message, I suspected that someone in the studio intentionally, perhaps in frustration–or else accidentally–started the broadcast from the beginning again.

At this point, I started recording. The five-number sets continue for about a minute, then the carrier unexpectedly drops:

Feature continues here with audio: Cuban Numbers Station

 

Obscure Group Honors Cuban Spy-Trainee Adriana Pérez 3

The husband-wife spy team of Adriana Perez and Gerardo Hernandez

The husband-wife spy team of Adriana Perez and Gerardo Hernandez

Prensa Latina (PRELA) announced that Adriana Perez, wife of imprisoned spy Gerardo Hernandez, “was awarded the Silver Dove international prize” for her efforts in support of the Cuban Five. The honor appears to have been bestowed by a little-known group called the Central Council of the International Union of World Leaders.

The award ceremony was held in Moscow at the headquarters of the Russian presidency. According to PRELA, other honorees included citizens from Russia, Japan, the United Arab Emirates, India,  Ukraine, Poland and Macedonia. PRELA reported that the awards recognize contributions to “social, cultural, moral and spiritual traditions.”

Editor’s Note:  PRELA failed to report was that Adriana Pérez O’Connor was in training as a Directorate of Intelligence (DI) asset when the Wasp Network (La Red Avispa) was brought down in September 1998. She and her children were deported and permanently banned re-entry visas. Her mission had been to courier messages and material between Havana and Miami.