Two double agents, a prison swap and code from outer space: did these spies save US-Cuba relations?

The Guardian

Jim Popkin 

“It’s like a time-lapse photo,” one US intelligence official says of Rolando Sarraff Trujillo’s guidance in helping multiple agencies unravel Cuban cryptography. Ana Montes will live behind bars until 2023. Illustration: Nate Kitch for Guardian US Opinion

From a maximum-security prison in Texas, former United States military analyst Ana Montes has been offering up bumper-sticker justifications for why she betrayed her country and spied on behalf of the Cuban government over the course of 17 years. “I believe that the morality of espionage is relative,” Montes wrote in a private letter to a friend last year. “The activity always betrays someone, and some observers will think that it is justified and others not, in every case.”

Montes had no idea how prophetic her words would be. While the 57-year-old American citizen remains locked up as one of the most damaging spies in US history, the Cuban-born spy who led American investigators to Montes was set free to worldwide applause last week, during a landmark thaw in US-Cuban relations. Several news outlets have since identified the Cuban double-agent as Rolando Sarraff Trujillo, and multiple US officials I’ve interviewed this past week have described him as a cryptographer whose code-breaking secrets have been the gift that keeps on giving to the CIA, NSA and FBI.

I have been following the Montes case for more than a decade, and profiled Montes and her family for the Washington Post Magazine last year. Despite extensive interviews with the officials who pursued her – and even access to a secret CIA profile of Montes – I never learned of the existence of the Cuban code geek who helped bring her down. On Wednesday, President Obama broke the news, hailing the Cuban double-agent as “one of the most important intelligence agents that the United States has ever had in Cuba”.

As I retraced the colliding paths of these dueling spies, a senior Obama administration official revealed to me on Friday that the Cubans had never requested the release of Ana Montes – not a single time over 18 months of secret prisoner-swap negotiations. The once-revered Pentagon analyst known as the “Queen of Cuba” had been left behind, a fitting betrayal for a woman who made a career out of duplicity and deceit.

Then-CIA director George Tenet presented Montes with a certificate of distinction in 1997.

By the time Montes attended graduate school at the Johns Hopkins University in the early 1980s, her anti-authoritarian worldview was fully baked. It didn’t take long for her to meet a like-minded student who seemed eager for a friend. The gregarious grad student was, in fact, a Cuban talent scout who wanted “to facilitate the recruitment of Montes to serve as an agent of the Cuban Intelligence Service,” prosecutors divulged last year.

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In 1985, Montes would find herself on a clandestine trip to Cuba for operational training, and before long she had found work with the Defense Intelligence Agency (DIA), the Pentagon’s major producer of foreign military intelligence. The Cubans “tried to appeal to my conviction that what I was doing was right,” Montes would later admit to investigators, in the first of many naïve assumptions that would come back to haunt her.

For the next 16 years, Montes feverishly worked two jobs, her star rising in Washington and Havana. By day she was a whip-smart analyst for the DIA. At night, she re-typed every top-secret document she could remember onto a Toshiba laptop provided by the Cuban intelligence service. Soon she was briefing the Joint Chiefs of Staff and the National Security Council, and won a certificate of distinction from then-CIA Director George Tenet.

All the while, Montes was meeting handlers in Washington-area Chinese restaurants, and artfully slipping in and out of Cuba to debrief the island’s intelligence officers. As Cuban-American relations stalled, the Soviet-trained masters of deception taught Montes how to pass packages to agents innocuously, beat the lie detector and, importantly, retrieve coded messages in the privacy of her DC apartment.

Montes got her orders the Cold War way: through numeric messages transmitted anonymously over shortwave radio. Tres-cero-uno-cero-siete, dos-cuatro-seis-dos-cuatro, a haunting female voice would drone on into the night, cutting through the otherworldly static. Montes would key the digits into her laptop, and a Cuban-installed decryption program would convert the numbers into Spanish-language text.

It was a code almost from another universe, practically begging to be broken by an enemy not that far away.

When asked by the Guardian, spokespeople for the CIA, DNI and NSC would not confirm or deny if Roly Sarraff Trujillo is the unnamed Cuban released last week as part of one of the prisoner swaps that led to improved US-Cuban relations. Illustration: Nate Kitch for Guardian US Opinion

More than 1,000 miles south in Cuba, Rolando Sarraff Trujillo was making a name for himself, too. After graduating in 1990 from the University of Havana, the handsome father of one – known to friends as “Roly” – began work for Cuba’s Directorate of Intelligence (DI). According to an online biography posted by his family, Sarraff Trujillo was employed as a lowly journalist assisting the intelligence directorate. In reality, he was a skilled cryptographer helping to encrypt messages to and from Cuba’s far-flung network of spies, said Chris Simmons, a former chief of a Cuban counterintelligence unit in the DIA who helped investigate Montes. “He worked on agent communications,” Simmons told me.

But Roly Sarraff Trujillo did more than that – he was a one-man intelligence goldmine. As a cryptographer, Sarraff Trujillo understood precisely how Cuba communicated with agents in the field, chiefly through the same “numbers station” broadcasts that Montes picked up night after night on her store-bought Sony radio. “He gave up how the Cubans transmitted HF [high frequency] broadcasts,” Simmons said. “He revealed communications shortfalls” that the CIA could take advantage of.

As a backroom comms guy, Sarraff Trujillo likely did not know the true identities of the Americans working on Havana’s behalf, Montes included. But the technical data and mastery of Cuban cryptography keys that Sarraff Trujillo imparted to the CIA would guide and even supercharge Americans investigators’ efforts for more than a decade – inextricably linking him with his polar opposite in espionage, even as he helped to out her.

“It’s like a time-lapse photo ... a gradual process,” said one current US intelligence official of Sarraff Trujillo’s codebreaking breakthroughs.

Another US official with knowledge of the case told me that Sarraff Trujillo and two Cuban defectors working for the CIA provided computer records straight from Cuba’s Directorate of Intelligence. “That data is a treasure trove of information about Cuban intelligence,” the second official told me.

That data is a treasure trove of information about Cuban intelligence.

From the records, the CIA was able to deduce how many agents the Cubans were running, their rough geographical locations and the command structure of the DI. Now American investigators knew where to look, and how to decipher encrypted messages sent to illegal agents hiding in the US.

US intelligence officials refuse to confirm or deny if Sarraff Trujillo is, in fact, the mystery Cuban released last week in exchange for three Cuban spies held in the United States along with, in a separate deal announced on the same morning as the expanded diplomatic relations, the imprisoned American contractor Alan Gross. Sarraff Trujillo’s sister, Vilma, declined comment in an email, as did spokespeople for the CIA, National Security Council and Director of National Intelligence (DNI).

But the DNI gave clues to Sarraff Trujillo’s identity by revealing on Wednesday that the man “has spent nearly 20 years in a Cuban prison due to his efforts on behalf of the United States”. The Cubans arrested Trujillo in November 1995, on espionage charges, meaning he’s been imprisoned for the last 19 years. US officials have told the New York Times, the Associated Press and other media outlets that Sarraff Trujillo was indeed the CIA’s man in Havana. “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 in question, Simmons told Newsweek on Wednesday. “I am 99.9% sure that Roly is the guy.”

Ana Montes would tune this radio to a short-wave frequency and wait for a spy broadcast full of seemingly random numbers to begin. Roly Sarraff Trujillo helped US investigators crack the code.

In the years following Sarraff Trujillo’s arrest, American investigators began to methodically work their way towards Montes. Ironically, it was Ana’s own sister, Lucy, who would play a key role in helping the FBI identify and capture the Queen of Cuba.

It began with a Cuban spy ring based in Florida. More than a dozen members strong, the so-called Wasp Network was infiltrating Cuban exile organizations and US military sites in Florida. Armed with Sarraff Trujillo’s intelligence and aided by other tipsters, American officials were able to pinpoint key Wasp conspirators. The FBI’s Miami field office began searching their homes surreptitiously and uncovered secret “crypto keys” on their laptops that deciphered ongoing communications with Havana, a US official familiar with the case told me.

The Cubans fucked up. They used the crypto keys more than once.

The Cubans were supposed to change the crypto codes every six months, the official said, to minimize security risks. But they got careless. “The Cubans fucked up. They occasionally used the crypto keys more than once,” the official said.

By applying the crypto keys to older coded shortwave transmissions that the NSA routinely recorded, the FBI began to build a profile of a senior US official who was aiding the Cubans. FBI special agents now knew that their “UNSUB” – or unidentified subject – had high-level access to US intelligence on Cuba and had purchased a specific type of Toshiba laptop to communicate with Havana.

It was 1998, and Lucy Montes was working in Miami as an FBI language analyst who translated wiretaps and other sensitive communications. The FBI called on her to translate hours of wiretapped conversations of the Wasp spies. Although Ana presumably would have been proud to learn that her sister had helped expose a Cuban spy ring, Lucy knew from years of frustrating trial and error that Ana refused to discuss her career. Ever. Lucy never even brought it up.

With the Wasp arrests, Ana’s handlers pulled back and assessed the fallout. Ana was alone, and she was scared – with good reason.

By September 2000, Chris Simmons learned from a fellow intelligence officer that the FBI was having difficulty identifying an UNSUB spying for the Cubans. Simmons shared the tip with Scott Carmichael, a “mole hunter” whose job it was to ferret our spies and other security risks within the DIA. Carmichael and a colleague began inputting some of the FBI’s closely held clues into their employee databases. After scanning through a hundred possible employee matches, a name popped up. Except this name came from deep within the bureaucracy: ANA BELEN MONTES.

Following months of investigative scrutiny, the FBI put a tail on Montes. They videotaped her making suspicious calls on pay phones, even though she carried a cellphone. They gained access to her banking accounts, through the use of a national security letter, and learned that Montes had applied for a line of credit in 1996 at CompUSA. Her purchase? The same model of Toshiba laptop that had been referenced in the coded Cuban communications that Sarraff Trujillo knew so much about.

Once FBI black-bag operatives searched Montes’s apartment and discovered a Sony shortwave radio and Toshiba laptop, it was all over. The hard drive, which Montes had tried to wipe clean, included instructions on how to translate Cuban high-frequency broadcasts. One file mentioned the true last name of a US intelligence officer operating undercover in Cuba. Montes had revealed the agent’s identity, and her Cuban intelligence officer thanked her in writing: “We were waiting here for him with open arms.”

The Cubans “tried to appeal to my conviction that what I was doing was right,” Montes would admit to investigators. “There’s nothing to be admired,” her sister says. Illustration: Nate Kitch for Guardian US Opinion

After pleading guilty to espionage, Montes told her CIA debriefers she felt she had a duty to protect Cuba from its neighbor up north. “All the world is one country,” she said. “In such a world-country, the principle of loving one’s neighbor as much as oneself seems to me to be the essential guide to harmonious relations.”

But despite last week’s détente between the United States and Cuba, it’s hard to imagine that the events Montes and Sarraff Trujillo set into motion more than two decades ago will amount to any kind of lasting harmony. One current US intelligence official predicted last week, as the White House was declaring a man who sounded a lot like Roly Sarraff Trujillo “a legitimate hero”, that the opening of embassies in Havana and Washington will simply make spying more convenient – with each nation’s spies more abundant and easier to follow.

“You still have an intelligence service, and we still have an intelligence service,” he told me. “It won’t be a sudden change of heart for either side.”