Red flags, missed clues: How accused U.S. diplomat-turned-Cuban spy avoided scrutiny for decades

Manuel Rocha was well known in Miami’s elite circles for an aristocratic, almost regal, bearing that seemed fitting for an Ivy League-educated career U.S. diplomat who held top posts in Argentina, Bolivia, Cuba and the White House. “Ambassador Rocha,” as he preferred to be called, demanded and got respect.

So former CIA operative Félix Rodríguez was dubious in 2006 when a defected Cuban Army lieutenant colonel showed up at his Miami home with a startling tip: “Rocha,” he quoted the man as saying, “is spying for Cuba.”

Rodriguez, who participated in the 1961 Bay of Pigs invasion in Cuba and the execution of revolutionary “Che” Guevara, believed at the time that the Rocha tip was an attempt to discredit a fellow anti-communist crusader. He said he nonetheless passed the defector’s message along to the CIA, which was similarly skeptical.

“No one believed him,” Rodriguez said in an interview with The Associated Press. “We all thought it was a smear.”

That long-ago tip came rushing back in devastating clarity in December when the now-73-year-old Rocha was arrested and charged with serving as a secret agent of Cuba stretching back to the 1970s — what prosecutors called one of the most brazen and long-running betrayals in the history of the U.S. State Department.

Rocha was secretly recorded by an undercover FBI agent praising Fidel Castro as “El Comandante” and bragging about his work for Cuba’s communist government, calling it “more than a grand slam” against the U.S. “enemy.” And to hide his true allegiances, prosecutors and friends say, Rocha in recent years adopted the fake persona of an avid Donald Trump supporter who talked tough against the island nation.

“I really admired this son of a bitch,” an angry Rodríguez said. “I want to look him in the eye and ask him why he did it. He had access to everything.”

As Rocha pleaded not guilty from jail this week to 15 federal counts, FBI and State Department investigators have been working to decipher the case’s biggest missing piece: exactly what the longtime diplomat may have given up to Cuba. It’s a confidential damage assessment, complicated by the often-murky intelligence world, that’s expected to take years.

The AP spoke with two dozen former senior U.S. counterintelligence officials, Cuban intelligence defectors, and friends and colleagues of Rocha to piece together what is known so far of his alleged betrayal, and the missed clues and red flags that could have helped him avoid scrutiny for decades.

It wasn’t just Rodríguez’s tipster — whom he refused to identify to the AP but says was recently interviewed by the FBI. Officials told the AP that as early as 1987, the CIA was aware Castro had a “super mole” burrowed deep inside the U.S. government. Some now suspect it could have been Rocha and that since at least 2010 he may have been on a short list given to the FBI of possible Cuban spies high up in foreign policy circles.

Rocha’s attorney did not respond to messages seeking comment. The FBI and CIA declined to comment. The State Department said in a statement it will continue to work with relevant agencies to “fully assess the foreign policy and national security implications of these charges.”

“This is a monumental screw-up,” said Peter Romero, a former Assistant Secretary of State for Latin America who worked with Rocha. “All of us are doing a lot of soul searching and nobody can come up with anything. He did an amazing job covering his tracks.”

Humble beginnings

Before he was charged with being a Cuban agent, Rocha’s life embodied the American dream.

He was born in Colombia and at age 10 moved with his widowed mother and two siblings to New York City. They lived for a while in Harlem while his mother worked in a sweatshop and got by with the help of food stamps.

A talented soccer player with a sharp intellect, he won a scholarship for minorities in 1965 to attend The Taft School, an elite boarding school in Connecticut. Overnight he was catapulted from what he called a “ghetto” engulfed in race riots to a refined world of American wealth.

“Taft was the best thing that happened to my life,” he told the school’s alumni magazine in 2004.

But as one of only a few minorities at the school, Rocha says he suffered discrimination — including a classmate who refused to room with him — something that fueled a grudge that friends suspect may have led him to admire Castro’s revolution.

“I was devastated and considered suicide,” he told the alumni magazine.

From Taft, he went to Yale, where he graduated with honors with a degree in Latin American studies, and then on to graduate work at Harvard and Georgetown.

It’s not clear exactly how Rocha may have been recruited by Cuba but prosecutors say it happened sometime in the 1970s when he was still racking up degrees and American college campuses were teeming with students sympathetic to leftist causes.

In 1973, the year he graduated from Yale, Rocha traveled to Chile, where prosecutors say he became a “great friend” of Cuba’s intelligence agency, the General Directorate of Intelligence, or DGI. That same year, the CIA helped topple the Castro-backed socialist government of Salvador Allende, replacing it with a brutal military dictatorship.

Around the same time, Rocha entered the first of his three marriages, to an older Colombian woman he barely spoke about to friends, and who is now under scrutiny for possible ties to Cuba, according to those who have been questioned by the FBI. The AP was unable to reach the woman or locate any record of their marriage.

‘All part of a plan’

After joining the foreign service in 1981, one of Rocha’s first overseas postings was as a political-military affairs officer in Honduras, where he advised the Contras in their fight against Cuba-backed leftist rebels in neighboring Nicaragua.

In 1994, he went to the White House to work as Director of Inter-American Affairs on the National Security Council, with responsibility for Cuba. That same year, he wrote a memo, “A Calibrated Response to Cuban Reforms,” urging the Clinton administration to begin dismantling U.S. trade restrictions, according to Peter Kornbluh, a national security expert who interviewed Rocha for a 2014 book.

The secretary of state planned to announce the policy overhaul following the U.S. midterm elections, according to Kornbluh. But that speech was never delivered. Republican hardliners who took control of Congress enacted legislation in 1996 hardening the embargo and blocking any effort to improve relations with Havana.

From Washington, Rocha was dispatched to Havana, where he served for two years as the principal deputy of the U.S. Interests Section. It was a perilous time — in the wake of the 1996 aerial shootdown of a “Brothers to the Rescue” propaganda plane over Cuba that killed four Castro opponents — and the DGI would have had almost unfettered access to the diplomat.

Rocha’s biggest known favor to Cuba, intentional or not, came during his final and most important diplomatic post, as U.S. Ambassador to Bolivia, when he intervened in the country’s presidential election to help a Castro protégé.

At an embassy event in 2002, Rocha inserted into his carefully scripted remarks a warning to Bolivians that voting for a narcotrafficker — a not-so veiled reference to coca grower-turned-presidential candidate Evo Morales — would lead the U.S. to cut off all foreign assistance.

“I remember it vividly. I was so uncomfortable,” said Liliana Ayalde, a fellow foreign service officer who later served as U.S. Ambassador to Paraguay and Brazil. “I told him it wasn’t appropriate for the Ambassador to say these remarks with elections just around the corner.”

The backlash was immediate. Bolivians deeply resented the idea of the U.S. interfering in their elections, and Morales, until then a long shot, surged in the polls and almost won. Three years later when he did prevail, he credited Rocha with being his “best campaign chief.”

Today, Ayalde wonders whether Rocha’s last hurrah as a foreign service officer was an act of self-sabotage, done at the direction of a foreign power to further damage the U.S.’ standing in Latin America, traditionally referred to as “Washington’s backyard.”

“Now that I look back,” she said, “it was all part of a plan.”

Super mole?

As early as 1987, when Rocha was a few years into his ascendant career, the U.S. was made aware of a Cuban “super mole” burrowed into the Washington establishment, according to Brian Latell, a former CIA analyst.

The information was provided by Florentino Aspillaga, who defected while heading the DGI’s office in Bratislava, now the capital of Slovakia.

Before Aspillaga died in 2018, he told the CIA that four dozen Cubans it recruited were actually double agents — or “dangles” in spy parlance— carefully selected by the DGI to penetrate the U.S. government. Latell said Aspillaga also spoke of two highly productive spies inside the State Department.

While Aspillaga didn’t know any of their names, the revelation sent shockwaves through the CIA.

“One of Aspillaga’s major revelations was that Fidel Castro himself was serving to a large degree as Cuba’s spymaster,” Latell said.

Enrique Garcia, who defected to the U.S. in the 1990s, also caught wind of the clandestine spy ring while running Cuban agents in Latin America. He said the documents he saw, which carried “Top Secret” and State Department markings, were so valuable that they were sent directly to Castro’s residence, bypassing the interior minister who oversaw the DGI.

“I have no doubt Rocha was part of that ring,” said Garcia, who told the FBI about the spy ring years ago.

Jim Popkin, author of “Code Name Blue Wren,” a book about Ana Montes, the highest-level U.S. official ever convicted of spying for Cuba, said his intelligence sources recently told him that Rocha’s name was on a short list of at least four possible Cuban spies that had been in the FBI’s hands since at least 2010. AP was not able to independently confirm that.

“The FBI has been aware of Rocha for a dozen years,” Popkin said. “That’s likely what stirred interest that led to his arrest years later.”

Peter Lapp, who oversaw FBI counterintelligence against Cuba between 1998 and 2005, and wrote a book on Montes, “Queen of Cuba,” said he was unaware whether Rocha had been on the bureau’s radar. But he acknowledged that in the national security hierarchy, Cuba is often an afterthought to Russia, China and more dangerous threats.

At the time of Rodríguez’s 2006 tip about Rocha spying for Cuba, for instance, U.S. counterintelligence investigators were occupied with the U.S. war in Iraq, the airstrike that killed al-Qaida leader Abu Musab al-Zarqawi, and controversial detention and interrogation programs overseas.

“You don’t get promoted to the senior ranks of the FBI counterintelligence division by focusing on Cuba,” Lapp said. “But it’s a country we ignore at our peril. Not only are the Cubans really good at human intelligence but they are experts at brokering information to some of our biggest adversaries.”

‘I have access’

Following his retirement from the foreign service in 2002, Rocha embarked on a lucrative career in business, racking up a number of senior positions and consulting jobs at private equity firms, a public relations agency, a Chinese automaker and even a company in the cannabis industry.

“I have access to just about every country in the region or know how to get it,” he bragged to the Miami Herald in 2006.

From 2012 to 2018, he served as President of Barrick Gold’s subsidiary in the Dominican Republic, overseeing production at the world’s sixth-largest gold mine. Rodríguez’s mementos of his one-time friendship with Rocha include a photo of the former diplomat in a hard hat lugging around a freshly extracted chunk of gold.

John Feeley, who worked under Rocha when he joined the State Department and eventually became Ambassador to Panama, remembers his former mentor urging him to reject pro bono work in retirement and instead chase a paycheck.

“He was openly and vocally motivated by making money in his post-foreign service career,” Feeley said, “which wasn’t typical among former diplomats.”

One business that has received new scrutiny in the wake of Rocha’s arrest was a venture he headed with a group of offshore investors to buy up at a steep discount billions of dollars in claims against Cuba’s government for farmland, factories and other properties confiscated during the communist revolution.

Rocha and his partner said that there was no way the Cuban government would ever pay up and that the U.S. government was unlikely to help, recalled claim holder Carolyn Chester, whose father was a former AP journalist and later close to deposed Cuban dictator Fulgencio Batista.

Chester remembered how the pair rolled up to meet her in Omaha, Nebraska, in a limousine and delivered a polished presentation in which they played off one another “like a tag team.”

While his partner presented the facts of their offer for a claim to a farm and other seized property, “Rocha would tug on our heartstrings,” recounting a supposed meeting they had with Chester’s parents years before in Washington.

Chester, who ultimately decided not to sell, said the meeting left her with doubts about Rocha, in part because she was all but certain her father’s poor health would have kept her parents from making such a trip to Washington. And she found it strange that Rocha and his partner spoke as if “they knew for sure” of the intentions of Cuban officials.

The idea, according to Rocha’s former business partner, Tim Ashby, was to “kill communism with capitalism” by swapping the claims for land concessions, leases and joint ventures in Cuba at a time when the communist island was desperate for foreign investment.

“For Cuba, there was a lot more at play,” said Ashby, a lawyer and former senior official in the U.S. Commerce Department. “This was crucial to normalizing relations with the U.S.”

The investment group would eventually spend around $5 million buying up nine claims valued at over $55 million, Ashby said. But the venture collapsed after some claim holders complained to the George W. Bush administration that they thought they were being bamboozled. In 2009, the Treasury Department moved to bar the transfer of any certified claims against Cuba.

That didn’t stop Rocha from continuing to make money. Records show that since 2016 alone, Rocha and his current wife spent more than $5.2 million to buy a half-dozen apartments in high-rise buildings in Miami’s financial district. This month, four of those properties were transferred entirely into his wife’s name, a move former law enforcement officials said could potentially shield them from government seizure.

In hindsight, Ashby acknowledged he was taken in by the image his former partner wanted the world to see.

“He was fiercely anti-communist and a staunch, early, Trump supporter,” he said. “Rocha was the last person I would have suspected of being a Cuban spy.”

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Republished with permission of The Associated Press.