CubaBrief: Spy tales: the patriot Juanita Castro, the traitor Ana Belen Montes, and the alleged traitor Ambassador Manuel Rocha.

On Monday, December 4th three historic events took place: Miguel Diaz-Canel arrived in Iran to meet with the Ayatollah, and the president of Iran pledging an alliance against Western democracies, Fidel Castro’s younger sister Juanita Castro, an anti-communist who worked for the CIA died in Miami at age 90, and Ambassador Victor Manuel Rocha was arrested for having spied for the Castro regime since 1981. It is a moment for moral clarity.


Juanita Castro on Meet the Press in 1964.

Juanita Castro, Fidel Castro’s younger sister who passed away on December 4th in the 2009 RTVE Channel 2 documentaryMy brothers and I” said,”Fidel himself said that I had betrayed him. I never betrayed Fidel. I have not betrayed anyone. Fidel, unfortunately and with pain that I feel very deeply, betrayed us all, including his own family.”   Juana de la Caridad Castro Ruz was born in Birán, Cuba, on May 6 1933 and passed away at 90 years of age in Miami on Monday, December 4, 2023. Both she and her older brother Fidel died at age 90, but their lives could not have been more different..

Juana de la Caridad, better known as Juanita, had backed her brothers in their struggle against Fulgencio Batista, but when she saw the Cuban revolution turn to communism, summary executions, and much injustice she began helping its victims. Her home became a place of refuge for those pursued and persecuted by the Castro dictatorship. She was approached in 1961, and took the code name “Donna” when she began working against the new dictatorship for the Central Intelligence Agency (CIA) .

Juanita went into exile in 1964, and publicly broke with the Cuban revolution, denouncing communism. She broke with the CIA during the Nixon Administration she says, because the White House’s detente with the Soviet Union led her agency contacts to  downplay her criticism of the Castro dictatorship, and she sent them packing.  The rest of her life she spoke plainly about the evils of the Castro regime, and repeatedly called on her brothers to surrender power, and let Cubans live in freedom.


Ana Belen Montes, Traitor and spy for the Castro dictatorship.

Ana Belen Montes, the Pentagon’s top analyst for Cuba who was arrested on September 21, 2001 for spying for the Castro regime for 17 years was released on January 6, 2023 from the Federal Medical Center (FMC) – Carswell, in Forth Worth, Texas where she was being held. Montes was in federal prison for over 21 years, and now resides in Puerto Rico.

Information she passed to Havana, in 1987 it is believed got 65 U.S. allied Salvadoran soldiers in Central America killed, and at least one American. Montes regularly briefed the Joint Chiefs of Staff, the National Security Council, and the State Department downplaying Cuban military capabilities, and providing their feedback to the Castro regime’s Intelligence Directorate (DI).  Her actions during the February 24, 1996 Brothers to the Rescue shootdown, and the influence operation she conducted to direct blame away from Castro, and onto the victims, first drew the attention of investigators. She also drafted a Pentagon report in 1997 stating Cuba had a “limited capacity” to harm the United States that Fidel Castro described as “an objective report by serious people.”

Mark Kelton, a former member of the CIA, reviewed Peter Lapp’s book “Queen of Cuba: An FBI Agent’s Insider Account of the Spy Who Evaded Detection for 17 Years” for The Cipher Brief in a article titled “The Last Analog Spy” in which he reveals why investigators were quick to arrest Montes in September 2001.

“Concern that Montes might share US military plans for responding to 9/11 terror attack with the Cubans, was the determining factor in the decision by the Department of Justice and FBI to arrest her.  During her debriefing, Lapp asked Montes whether she would have passed the DI the US war plans if she’d had an opportunity to do so.  Her reply; that she would have as “she believed she had a moral right to tell the Cubans how we fought a modern war in case we attacked Cuba;” was not surprising.  But her follow-up remark that if Cuba gave the plans to Al-Qa’ida or the Taliban and it resulted in the deaths of more Americans, “Then that’s the risk they took” was jarring for what it said about her cold-bloodedness.”

Alleged traitor

Ambassador Manuel Rocha

Ambassador Manuel Rocha has been charged “with committing multiple federal crimes by secretly acting for decades as an agent of the government of the Republic of Cuba.,” but still has not had his day in court, and thus the prefix “alleged”. The U.S. system of jurisprudence finds that one is innocent until proven guilty, The evidence presented in the charging document is damning.

The Washington Post led with the following description of what the former Ambassador is charged with by the Justice Department.

The Justice Department unsealed charges Monday against a retired ambassador, accusing him of being a “clandestine agent” for decades — allegedly betraying his country by acting on behalf of Cuba’s spy agency. The arrest of Manuel Rocha, 73, capped a year-long undercover sting operation in which an FBI agent pretending to be a Cuban intelligence operative secretly recorded Rocha making incriminating statements about his life of diplomatic deception.

It is early days yet, but some are already saying that Ambassador Rocha could have done more harm to the United States than Ana Belen Montes. CIA official Robert Baer in an interview with NPR’s Mary Louise Kelly observed, “So I would say offhand, until we hear about what the damage was – and I’m waiting from the Department of Justice and FBI to say – and this will take a couple years – is this is probably the most damaging spy scandal or penetration of the U.S. government, you know, going way back to Roosevelt. And I don’t say that lightly.”

“This action exposes one of the highest-reaching and longest-lasting infiltrations of the United States government by a foreign agent,” said Attorney General Merrick B. Garland.

There is a huge difference from someone spying against a totalitarian communist dictatorship, and someone spying for that kind of regime to advance its objectives, especially a state sponsor of terrorism like Cuba.

The Telegraph, December 5, 2023

Juanita Castro, sister of Fidel and fervent anti-communist who informed for the CIA and fled Cuba – obituary

She was a CIA informer, codename Donna, who concealed documents in cans of food and sent out codes via tunes from a clandestine radio

Telegraph Obituaries 5 December 2023 • 12:43pm

Juanita Castro, who has died aged 90, was the younger sister of Fidel and Raúl Castro; but while they established Cuba’s communist regime, she defected in the early 1960s and became a CIA informant, smuggling documents out of the country and transmitting messages via a clandestine radio.

It was in late June 1964 that Juanita Castro, then 31, called a press conference in Mexico City and, teary-eyed, declared that she could no longer remain indifferent to what was happening in Cuba: “My brothers Fidel and Raúl have made it an enormous prison surrounded by water. The people are nailed to a cross of torment imposed by international communism.” She had left Havana 10 days earlier, supposedly on a short visit to see her sister Emma.

It is unlikely that this ruse fooled anyone. Rumours about her opposition to the regime had been rife, and she was suspected of facilitating the escape of more than 200 government critics. When she decided to flee even her chauffeur remarked on her hardly inconspicuous luggage of 11 – some say 21 – bags. Most likely it was Raúl, with whom she had always been close, who turned a blind eye to her subterfuge, and assisted in securing her a visa.

For by 1963 Juanita and Fidel Castro had severed ties. Though he was loath to arrest her, Fidel clearly did not anticipate the lengths that Juanita would go to in her anti-communist mission, during which she denounced her brothers as despots on the radio. 

“The incident for me is personally very bitter,” Fidel told reporters, ordering the press never to bring up the matter again. Juanita’s defection severely tarnished the regime’s image in Latin America, where families are traditionally seen as tight-knit and remain, at least in public, fiercely loyal.

Juanita had not, however, always been opposed to the revolutionary cause. In 1958 she had even travelled to America to solicit funds in a bid to oust the dictator Fulgencio Batista. When her brothers’ revolution triumphed the following year, she went to the countryside to instal health clinics and manage social programmes. 

But as executions of opponents became commonplace, the media was censored and anti-religious measures were put in place, she grew disillusioned. The imposition of “agrarian reform” on the Castro family estates proved the last straw. 

When Fidel decided to further expropriate the land, Juanita set about selling the cattle. Fidel flew into a rage and denounced her as a “counter-revolutionary worm”.

For her part, she never believed in Fidel’s “radical conversion” to Marxism-Leninism, painting a picture of a man driven far more by power than by concern for the lives of the Cuban peasants. “Nobody thought for a second that he was going to be a communist,” she said.

She was always more forgiving of Raúl, who continued to act as her protector despite her political views. Tensions within the Castro family are captured in Andy Warhol’s 1965 film, The Life of Juanita Castro, based on a Life article from the previous year.

In this farcical set-up Juanita, Fidel, Raúl and revolutionary cohorts (all played by female actresses) sit on a stage as they are fed lines by the screenwriter Ronald Tavel. 

During the improvisations Juanita, who sits in a queenly chair fanning herself, delivers impassioned speeches that mock the revolutionaries’ machismo and flawed totalitarian ideals. As for Che Guevara: “I would let him know that he was meddling in a place where he didn’t belong.”

Juana de la Caridad Castro Ruz was born in Birán, Cuba, on May 6 1933, the fifth of seven children of Angel Castro and his cook, Lina Ruz, who in 1943 would become his second wife. Angel had gone to Cuba as a conscript to fight for Spain during the 1895-98 War of Independence. 

After selling railroad ties to the United Fruit Company, he moved into sugar cane, expanded into cattle, opened a general store, and through various occasionally underhand deals became one of the largest landowners in the Holguín province. In spite of Angel’s infidelities, the couple remained inseparable, and Juanita had, for the most part, a happy childhood.

Ever devoted to her parents, in 1998 Juanita Castro filed a libel suit against her niece, Alina Fernández, over passages about Angel and Lina in her autobiography, Castro’s Daughter: An Exile’s Memoir of Cuba. 

“People who were eating off Fidel’s plate yesterday come here and want money and power, so they say whatever they want, even if it’s not true. Part of my family were responsible for a lot of suffering in Cuba – you can’t change that,” she said. “But nobody has the right to offend Fidel’s family. Insult Fidel – there’s plenty to say.”

For decades Juanita was suspected of having been recruited by the CIA. In 2009 the publication of her memoir, Fidel and Raúl: My Brothers: The Secret History, confirmed that she was indeed a CIA informer who went by the codename Donna. 

It turned out that before she left Havana, where her home had become a refuge for opponents of the regime, she had been asked by the Brazilian ambassador, Virginia Leitão da Cunha, to meet a CIA agent, Tony Sforza.

The rendezvous was arranged for Mexico City in 1961. There she agreed to become “Donna”, learning to conceal documents in cans of food, and set up a code system using a clandestine radio and two tunes – Marchetti’s Fascination Waltz and the opening of Madame Butterfly.

As Juanita did not hold a government post it was unlikely that she would have been privy to official secrets, relying instead on anecdotes Fidel shared with his “bosom pals”. She also specified that she would not be involved in any violent attacks on her family. But the recruitment of a mole at the heart of the Americas’ communist stronghold was a rare Cold War success for the CIA, which is thought to have drawn up hundreds of assassination attempts on Fidel.

After her mother’s death, Juanita’s fate became increasingly uncertain and exile seemed the only plausible way out. From 1964 she made Miami her home and remained there for the rest of her life. 

Initially she continued working for the CIA, reporting on Latin American political hot spots throughout the Sixties. She was seen as a critical player in determining the outcome of Chile’s 1964 election, broadcasting messages to the country about the ills of communism.

American policy on Cuba shifted radically in the Nixon era, however, as it became apparent that the underground fight against Castro was having a negative impact on US-Soviet relations. The CIA asked Juanita to start issuing statements that communism was no longer a threat in Latin America. She felt betrayed and, refusing to compromise, cut ties with the agency.

Having always refused compensation for her intelligence services, she had little disposable income. To make a living she opened a pharmacy, Mini Price, in Little Havana, with a $5,000 loan from a friend. She worked there until 2007.

Juanita continued to support the new waves of Cuban exiles who arrived in Miami in the 1970s and 1980s. She provided free medical supplies to priests who looked after the community, and donated a house to the International Rescue Committee for refugees.

Though she worked a six-day week, she got much pleasure out of spending time in the garden of her small home and the flowers she grew there. When time allowed, she would go fishing and take long walks on Sanibel Island, on Florida’s west coast. Although she remained a quiet figure in Miami, shunning the spotlight of the more vociferous anti-Castro organisations, she was a well-respected member of the Cuban community.

She remained estranged from Fidel and Raúl, though she kept close ties with her other siblings, especially Emma. Her sister Angela died in 2012 and her brother Ramón in 2016. 

When Fidel died in November that year, Juanita Castro announced from her home in Miami, where the Cuban expat community was celebrating, that she would not be attending his funeral: “I want to clarify that I have never returned to [Cuba], nor do I have plans to do so…

“I’ve been in exile in Miami for 51 years. Like all the Cubans who left to find a space to fight for the freedom of their country, I have never changed my position, even though I had to pay a high price for the pain and isolation.”

Carmita and Hilda Morgade and Ana Ely Esteva, friends whose escape to Miami she had facilitated, were her closest companions. She called them the “sisters that life gave me”.

Juanita Castro, born May 6 1933, died December 4 2023

Newsweek, December 5, 2023

Juanita Castro, Fidel’s Sister Recruited by CIA, Dies in US

By Chloe Mayer

Dec 05, 2023 at 4:49 AM EST

Former Cuban leader Fidel Castro’s younger sister—and one of his fiercest critics— has died in Miami aged 90.

Juanita Castro, who was the fourth child of seven siblings, fled Cuba for Florida in 1964 after accusing her brother of turning the island into “an enormous prison surrounded by water.” She went on to work with the CIA, using the codename “Donna,” to try to bring about his downfall.

Fidel Castro, who was also 90 when he died in November 2016, was a towering figure of the 20th century who helped shaped American politics after the Cuban revolutionary built a communist state on the doorstep of the U.S.

His alliance with Moscow fueled the Cuban Missile Crisis in 1962, a 13-day showdown with the U.S. that brought the world the closest it has ever been to nuclear war. He went on to rule the country for decades, but ceded power to his brother Raul Castro in 2006 due to his ailing health. Raul Castro was later succeeded by Miguel Díaz-Canel in 2018.

Juanita Castro broke ranks with her powerful family by opposing Fidel Castro and she often spoke out publicly against his rule. Although she did express some sadness upon hearing of her brother’s death, she insisted she would never return to her homeland.

Journalist María Antonieta Collins, co-author of Juanita Castro’s memoir, announced news of her subject’s death on Instagram on Monday.

A translation of her post, which was written in Spanish, reads: “This is the news that I never wanted to give, but that, as her spokesperson in the last three decades of her life, I have to communicate.

“Today, at 90 years of age, Juanita Castro went ahead of us on the path of life and death, an exceptional woman, a tireless fighter for the cause of her Cuba.”

The family requested privacy, and would not be giving interviews, she added. The funeral would be private.

We ask for your prayers for the eternal rest of her soul,” the post ended.

Her cause of death has not been made public.

Juanita Castro obtained U.S. citizenship in 1984 and opened a pharmacy in Miami. She worked at the store for years before selling it to CVS in 2006.

In her memoir, My Brothers Fidel and Raul, the Secret History, she wrote that she found her life as a Cuban exile in Florida particularly challenging given her links to the country’s rulers.

“Undoubtedly, I have suffered more than the rest of the exiles, because nowhere along the Straits of Florida do they give me respite and few are those who understand the paradox of my life,” she wrote.

“For those in Cuba, I am a deserter because I left and denounced the regime in place. For many in Miami, I am ‘persona non grata’ because I am the sister of Fidel and Raul.”

The Washington Post, December 4, 2023

Ex-U.S. ambassador accused of being Cuba’s secret agent since 1981

Manuel Rocha is charged with acting on Cuba’s behalf for decades

By Devlin Barrett, Mary Beth Sheridan and Karen DeYoung

Updated December 4, 2023 at 6:30 p.m. EST| Published December 4, 2023 at 12:43 p.m. EST

The Justice Department unsealed charges Monday against a retired ambassador, accusing him of being a “clandestine agent” for decades — allegedly betraying his country by acting on behalf of Cuba’s spy agency.

The arrest of Manuel Rocha, 73, capped a year-long undercover sting operation in which an FBI agent pretending to be a Cuban intelligence operative secretly recorded Rocha making incriminating statements about his life of diplomatic deception.

Attorney General Merrick Garland called the Rocha case “one of the highest-reaching and longest-lasting infiltrations of the United States government by a foreign agent,” adding that in those secretly recorded conversations, Rocha repeatedly referred to the United States as “the enemy.”

The news of Rocha’s alleged duplicity stunned his friends and colleagues in U.S. diplomatic and intelligence circles.

“I never suspected, never had the slightest suspicion that he might be living a double life like the charging document describes,” said Brian Latell, a former senior CIA intelligence official who met Rocha in the early 1980s.

“I think I knew him as well as anyone else, and I never thought it was possible. I think Manuel was someone with many more talents, and many more facets, than frankly I had ever imagined, even as close as we were for so many years,” Latell said. “He was obviously doing very useful work for the Cubans.”

Former FBI agent Peter Lapp said the Rocha case is “very disturbing and concerning” because of the amount and types of intelligence Rocha could access. Lapp — whose book “Queen of Cuba” recounts a case he investigated against a different Cuban spy, U.S. defense analyst Ana Montes — said the court papers in Rocha’s case suggest that the FBI used the undercover agent to get Rocha talking, and that he apparently talked himself into criminal charges.

“That is what the bureau seems to be trying to do with the Rocha case, and he just didn’t bite fully,” Lapp said.

That technique was comparable to the FBI’s successful work against Kendall Myers, another former State Department employee who was coaxed into admitting at least some of his crimes during an undercover FBI operation, Lapp said. Without such admissions, it is doubtful prosecutors could bring charges over suspicious conduct that happened so many years ago, he said.

Myers, who admitted to dead drops and transferring information, was charged with espionage and sentenced to life in prison. Rocha, in contrast, is charged with conspiring to act as an agent of a foreign government without notifying the Justice Department, acting as an agent of a foreign government without such notification; and lying to obtain a passport.

The criminal complaint does not accuse him of specific acts of espionage. He faces up to 10 years in prison if convicted of the most serious charge.

At a brief court appearance in Miami on Monday, Rocha was ordered to remain in custody pending further hearings. His lawyer did not immediately respond to a request for comment.

Though a small country, Cuba has racked up some intelligence victories against the United States by finding people motivated to support the communist government against its capitalist and much larger adversary to the north.

“Cuba is so good at finding individuals who aren’t motivated by money,” said Lapp. “They find people who have a visceral empathy for what Cuba is trying to do in Latin America and Central America, and those people are morally aligned with them.”

Court papers filed in Miami describe meetings in which Rocha discussed his secret work for Cuba, including one where he said that the “Direccion” — a reference to that country’s General Directorate of Intelligence — “asked me … to lead a normal life.”

Rocha allegedly said he followed that instruction by creating a public reputation as “a right wing person,” when he in fact was committed to the cause of communist Cuba. He also allegedly spoke with pride of how much he was able to hurt the United States on Cuba’s behalf, saying “What we have done … it’s enormous … More than a grand slam.”

At one secretly recorded meeting between Rocha and the undercover agent, the diplomat allegedly described how he became a State Department employee: “I went little by little. … It was a very meticulous process. … I knew exactly how to do it and obviously the Direccion accompanied me. … They knew that I knew how to do it.”

Rocha was born in Colombia and became a U.S. citizen in 1978. He joined the State Department in 1981. The criminal complaint against him says that at least as early as that year, he “secretly supported the Republic of Cuba and its clandestine intelligence-gathering mission against the United States by serving as a covert agent of Cuba’s intelligence services.”

Authorities say Rocha pushed false and misleading information within the U.S. government and met with Cuban intelligence operatives. In the secretly recorded conversations with the undercover FBI agent, Rocha allegedly insisted he was still committed to the revolutionary cause of communist Cuba, according to the court papers unsealed Monday. Rocha’s arrest late last week was first reported by the Associated Press.

Over the years, Rocha rose through the ranks of the State Department to serve in positions at the U.S. embassies in the Dominican Republic, Honduras, Mexico and Argentina before ascending to more sensitive government posts. From mid-1994 to mid-1995, Rocha served on the National Security Council, with a portfolio that included Cuba. From there he worked for the State Department in Cuba.

Rocha was sworn in as the U.S. ambassador to Bolivia in July 2000, according to his State Department biography. He served in that role for about two years. That job and others gave him access to U.S. government secrets, including classified information. Authorities say Rocha repeatedly lied when answering security questions that determined whether he could keep those jobs.

“Those who have the privilege of serving in the government of the United States are given an enormous amount of trust by the public we serve,” Garland told reporters. “To betray that trust by falsely pledging loyalty to the United States while serving a foreign power is a crime that will be met with the full force of the Justice Department.”

From 2006 to 2012, Rocha served as an adviser to military officials at U.S. Southern Command — a part of the military whose area of responsibility includes Cuba.

John Feeley, a former U.S. ambassador to Panama who earlier had worked under Rocha at the embassy in the Dominican Republic, described him as a charming, confident and successful Latin America expert — known as a “ladies man … somebody who was going places.” Rocha’s arrest and charges are “a real John le Carré story,” Feeley said, referring to the late spy novelist.

Rocha and Feeley met again in 2018, when they were both retired, Feeley said. “He had gone full-on Donald Trump,” said Feeley. “He was a MAGA Republican.” In hindsight, Feeley added, “it was a perfect cover.”

Judith Bryan, who worked at the U.S. Interest Section of the Swiss Embassy in Havana when Rocha was a senior diplomat there in the late 1990s, said she “never would have imagined in my wildest dreams this was going on.”

At the time, staff members at the U.S. mission were trying to create bridges between civil society groups in Cuba and the United States, said Bryan, who served as a deputy public affairs officer at the mission. She said Rocha was “very supportive of that official policy” but did not seem sympathetic to Fidel Castro’s government.

The charging documents don’t describe how the FBI came to suspect Rocha — only that the agency received a tip about him before November 2022.

Espionage and intrigue, much of it centered in Miami, have roiled the U.S.-Cuba relationship since Cuba became a communist state after Castro’s 1959 takeover. Rocha’s arrest is unlikely to significantly affect relations between Washington and Havana, which have been at a low point since the Trump administration.

President Barack Obama reestablished diplomatic ties with the country after a break of more than a half-century and used executive power to circumvent many economic restrictions and lift a long-standing designation of Cuba as a state sponsor of terrorism.

Many of the lifted sanctions were reimposed by President Donald Trump, who also reinstated the terrorism sponsor designation several days before leaving office on grounds that Cuba had refused to extradite several Colombian guerrilla leaders sought by Bogota’s then-right-wing government. Colombia’s current leftist leader, President Gustavo Petro, rescinded the extradition requests last year and has reopened Cuban-sponsored peace negotiations with the group, the National Liberation Army.

President Biden as a candidate pledged to return to the Obama-era policies but has made few moves to do so. Although some restrictions have been eased, allowing more Americans to visit Cuba and permitting more trade, Biden has retained the terrorism designation and criticized the government in Havana for imprisoning political activists.

The Cuban government made no immediate comment on Rocha’s arrest.

Rocha had barely any involvement in electoral politics in the United States, public records show. He contributed to just one federal candidate last year, sending $750 to Rep. María Elvira Salazar (R-Fla.), according to filings with the Federal Election Commission.

Salazar seized on his arrest to portray Cuba as “a danger to our national security,” while also taking a swipe at Democrats in a post on X, formerly known as Twitter, writing, “Biden administration, wake up!” A spokesperson for Salazar said the congresswoman had no relationship with Rocha and had instructed her campaign to return the money.

Sheridan reported from Mexico City. Isaac Stanley-Becker contributed to this report.

Office of Public Affairs, U.S. Department of Justice, December 4, 2023

Former U.S. Ambassador and National Security Council Official Charged with Secretly Acting as an Agent of the Cuban Government

Federal prosecutors have charged Victor Manuel Rocha, 73, of Miami, Florida, a former U.S. Department of State employee who served on the National Security Council from 1994 to 1995 and ultimately as U.S. Ambassador to Bolivia from 2000 to 2002, with committing multiple federal crimes by secretly acting for decades as an agent of the government of the Republic of Cuba.

“This action exposes one of the highest-reaching and longest-lasting infiltrations of the United States government by a foreign agent,” said Attorney General Merrick B. Garland. “We allege that for over 40 years, Victor Manuel Rocha served as an agent of the Cuban government and sought out and obtained positions within the United States government that would provide him with access to non-public information and the ability to affect U.S. foreign policy. Those who have the privilege of serving in the government of the United States are given an enormous amount of trust by the public we serve. To betray that trust by falsely pledging loyalty to the United States while serving a foreign power is a crime that will be met with the full force of the Justice Department.”

“Like all federal officials, U.S. diplomats swear an oath to support and defend the Constitution of the United States. Acting as an agent for Cuba – a hostile foreign power – is a blatant violation of that oath and betrays the trust of the American people,” said FBI Director Christopher Wray. “The FBI will continue to rigorously defend against foreign governments targeting America, and we will find and hold accountable anyone who violates their oath to the United States, no matter how long it takes.”

“For decades, Rocha allegedly worked as a covert agent for Cuba and abused his position of trust in the U.S. government to advance the interests of a foreign power,” said Assistant Attorney General Matthew G. Olsen of the Justice Department’s National Security Division. “However long it might take, we will deliver justice to those who betray their solemn oaths to the American people.”

“The Southern District and our law enforcement partners stand ready to protect the United States from individuals who act unlawfully as agents of foreign governments,” said U.S. Attorney Markenzy Lapointe for the Southern District of Florida. “Individuals who violate federal law by engaging in clandestine activity for hostile foreign states, and by providing false information about those activities to the U.S. government, endanger American democracy. That is especially so for past or present employees of the United States who took an oath to uphold the U.S. Constitution, and for U.S. citizens who benefit from the freedoms and opportunities of this country. The U.S. Attorney’s Office and our law enforcement partners in South Florida, and elsewhere, will continue to vigorously enforce all federal laws.”

According to the complaint, beginning no later than approximately 1981, and continuing to the present, Rocha, a naturalized U.S. citizen originally from Colombia, secretly supported the Republic of Cuba and its clandestine intelligence-gathering mission against the United States by serving as a covert agent of Cuba’s General Directorate of Intelligence.

To further that role, according to the complaint, Rocha obtained employment in the U.S. Department of State between 1981 and 2002, in positions that provided him access to nonpublic information, including classified information, and the ability to affect U.S. foreign policy. After his State Department employment ended, Rocha engaged in other acts intended to support Cuba’s intelligence services. From in or around 2006 until in or around 2012, Rocha was an advisor to the Commander of the U.S. Southern Command, a joint command of the United States military whose area of responsibility includes Cuba.

The complaint alleges that Rocha kept his status as a Cuban agent secret in order to protect himself and others and to allow himself the opportunity to engage in additional clandestine activity. Rocha provided false and misleading information to the United States to maintain his secret mission; traveled outside the United States to meet with Cuban intelligence operatives; and made false and misleading statements to obtain travel documents.

According to the complaint, Rocha began his State Department career in 1981, rising through the ranks to serve in a variety of roles, including (1) from in or around February 1989 until in or around November 1991, as the First Secretary at the U.S. Embassy in Mexico City, Mexico; (2) from in or around November 1991 until in or around July 1994, as the Deputy Chief of Mission at the U.S. Embassy in Santo Domingo, Dominican Republic; (3) from in or around July 1994 until in or around July 1995, as a Department of State employee, as the Director of Inter-American Affairs on the U.S. National Security Council, with special responsibility for, among other things, Cuba; (4) from in or around July 1995 until in or around July 1997, as Deputy Principal Officer at the U.S. Interests Section in Havana, Cuba; (5) from in or around July 1997 until in or around November 1999, as Deputy Chief of Mission at the U.S. Embassy in Buenos Aires, Argentina; and (6) from in or around November 1999 until in or around August 2002, as Ambassador to Bolivia at the U.S. Embassy in La Paz, Bolivia.

The complaint alleges that, in a series of meetings during 2022 and 2023, with an undercover agent from the FBI posing as a covert Cuban General Directorate of Intelligence representative, Rocha made repeated statements admitting his “decades” of work for Cuba, spanning “40 years.” When the undercover told Rocha he was “a covert representative here in Miami” whose mission was “to contact you, introduce myself as your new contact, and establish a new communication plan,” Rocha answered “Yes,” and proceeded to engage in a lengthy conversation during which he described and celebrated his activity as a Cuban intelligence agent. Throughout the meetings, Rocha behaved as a Cuban agent, consistently referring to the United States as “the enemy,” and using the term “we” to describe himself and Cuba. Rocha additionally praised Fidel Castro as the “Comandante,” and referred to his contacts in Cuban intelligence as his “Compañeros” (comrades) and to the Cuban intelligence services as the “Dirección.” Rocha described his work as a Cuban agent as “a grand slam.”

Rocha is charged with conspiring to act as an agent of a foreign government without prior notification to the Attorney General; acting as an agent of a foreign government without prior notification to the Attorney General; and with using a passport obtained by false statement. He is expected to make an initial appearance before a U.S. Magistrate Judge in Miami today, Dec. 4.

The FBI Miami Field Office is investigating the case, with valuable contributions by the Department of State’s Diplomatic Security Service and the FBI’s Washington Field Office.

Assistant U.S. Attorneys Jonathan D. Stratton and John C. Shipley of the Southern District of Florida, along with Trial Attorneys Heather M. Schmidt and Christine A. Bonomo of the National Security Division’s Counterintelligence and Export Control Section are prosecuting the case. 

Anyone with tips can call 1-800-CALL-FBI (800-225-5324) or visit

A criminal complaint is merely an allegation. All defendants are presumed innocent until proven guilty beyond a reasonable doubt in a court of law.

Rocha complaint

Updated December 4, 2023

The Cipher Brief, November 21, 2023

The Last Analog Spy

BOOK REVIEW: Queen of Cuba: An FBI Agent’s Insider Account of the Spy Who Evaded Detection for 17 Years

By Peter J. Lapp with Kelly Kennedy / Post Hill Press

Reviewed by Cipher Brief Expert Mark Kelton

The Reviewer — Mark Kelton retired from CIA as a senior executive with 34 years of experience in intelligence operations including serving as CIA’s Deputy Director for Counterintelligence. He is currently a partner at the FiveEyes Group; a member of the Board of Trustees of Valley Forge Military Academy and College; member of the National Security Advisory Board of the MITRE Corp.; member of the Day & Zimmermann Government Services Advisory Board; member of the Siemens Federal Advisory Board; and a member of the Board of BigMediaTV.

REVIEW — Although we are only a little over two decades into it, the 21st century has already seen a lengthy list of betrayals of country and oath that have done great harm to US national security.  Bradley Manning, Edward Snowden, Harold Martin, Jerry Lee, Joshua Schulte and others of their ilk have all made headlines. Against such a malodorous backdrop, it is easy to forget this epoch began with the roll-up of one of the longest running espionage cases in American history. 

In his book, Queen of Cuba: An FBI Agent’s Insider Account of the Spy Who Evaded Detection for 17 Years, former FBI Special Agent Peter J. Lapp tells the story of Ana Belen Montes, a senior Defense Intelligence Agency (DIA) Cuba analyst who spied for 17 years for the Cuban intelligence service (DI).  It is a compelling insider view of Montes’s spying and the investigation that led to her 2001 arrest. 

Mr. Lapp’s casual writing style could be off-putting to those who like their espionage history presented in a ‘just the facts’ manner.  But I found it appropriate for a book that is at once a telling of the Montes story and a memoir of his FBI career.  On the face of it, this duality might seem a distraction.  But Lapp makes it work by juxtaposing his own background and service to our country with Montes’s upbringing and betrayal of that same nation.  His examination of the converging paths that brought investigative target and investigator together is particularly poignant given Montes’s family ties: her brother was an FBI Special Agent and her sister a translator on the Bureau investigation of the Cuban Directorate of Intelligence (DI) ’s “Wasp” network.

Montes has been called the last ideological spy.  What is meant by that, is that she is seen as the last in a long line of American traitors motivated by fealty to Marxist-Leninist ideology; in her case, the Cuban strain of that deadly virus.  Montes herself, Lapp tells us, “didn’t see herself as a communist…(she) sympathized with the goals of Cuban and Nicaraguan revolutions.”  Given the seeming fascination these days of many young people with disguised versions of the same dogma – likely a result of having been imbued on college campuses with a sanitized version of the actual brutal history of a creed responsible for the deaths of tens of millions – that judgement of being “last” is surely premature. 

Though he doesn’t use these words, Lapp frames Montes as driven by a form of romanticism.  Like many on the left in an earlier era, her path to serving a revolutionary cause went through Spain.  Montes travelled there in 1977 on a college year abroad at a time when the country was moving from the Franco era towards democracy.  She and her Puerto Rican friend “Mimi” moved in revolutionary circles.  Their friends in Spain, as Lapp notes, were all anti-American.  And it was there that Montes fell in love.  Twice.  First with a young Argentine singer who sang of revolution.  He spoke with Montes of US support for authoritarian governments in Latin America.  Their romance didn’t last.  But her love affair has another ending.  In her letters home, her sister noted, Montes called herself a “leftist” and wrote of “her newfound interest in Cuba.”

Someone other than her sister also took note because shortly after Montes enrolled at Johns Hopkins School of Advanced International Studies (SAIS) in 1982 she found a soulmate.  Or, more likely, the soulmate found her.  Montes and fellow-student Marta Velazquez quickly developed a friendship based on Montes’s growing anger over the Reagan Administration’s policies in Central America and her opposition to the invasion of Grenada.  In 1984, Marta introduced Montes to a ‘diplomat’ accredited to the Cuban UN Mission.  Over dinner in New York, DI officer Millan Chang-German soft-pitched Montes – who was then working at the Justice Department – to moonlight translating newspaper articles.

Millan need not have been so elliptical.  Montes, Lapp writes, immediately pushed back, describing the work as menial and indicating she could do more.  She readily agreed to Millan’s suggestion that she provide her “analysis of US government actions.”  On the train back to Washington, Montes announced to Marta that if she was really going to help the Cubans she had to join the US intelligence community (IC).  The Cuban DI seemingly knew early on what a golden opportunity they had in Montes.  Marta told Montes the DI thought she “could be one of the best”.  The best what went unsaid but was well understood.  As requested, Montes typed out her biography on a DI-provided typewriter (thereby relieving her recruiter of what, in my own experience, can be an onerous requirement).  The DI’s bet paid off when, in early 1985, Montes got an offer to join DIA as a Latin America analyst.  (Interestingly, the Cubans did not press Montes to try to get a job at CIA, an organization she hated.)

In March 1985, Montes and Marta travelled together to Cuba via Madrid – where falsified passports were passed to them – and Prague.  By the time Montes left the island, she and Marta had been trained on receiving encrypted radio traffic and how to beat the polygraph.  Montes – who was given the work-name “Sonia” – left Cuba a fully recruited and trained agent of the DI.  Montes’s sister rightly observed that by the time Montes walked into DIA for the first time in fall 1985, she had become “a full-fledged spy for Fidel Castro”. 

Lapp details Montes’s climb within the fraternity of Latin American analysts to the point where she earned the moniker the “Queen of Cuba.”  Her ruthless insistence on being right, underhanded tactics in securing plumb assignment and cold demeanor earned her no friends in the office.  But her knowledge and work ethic were unquestioned.  Montes cut a wide swath through the IC, attended conferences and established contacts she could leverage to the benefit of both DIA and the DI – the organization to which she owed her true allegiance.  There were, however, times when she was unable to restrain herself from injecting her hidden convictions into her analytical work.  Colleagues would later recall that her judgements regarding events in Cuba and Latin America sometimes revealed a bias in favor of the Castro regime.  Such instances were apparently written off as legitimate differences of opinion.  In retrospect, however, they should have revealed much about who and what Montes really was.

Montes might also be called the last analogue spy.  Montes’s use of old-school methodology to defeat modern insider threat detection tools serves as a lesson-learned for those charged with protecting sensitive information from anyone seeking to emulate her.  Montes, Lapp stresses, “never took anything home – no discs, no documents, no notes…She didn’t take pictures with a miniature camera or scan documents”.  Instead, Lapp emphasizes, “every day she memorized three things she learned she thought the Cubans needed to know.”  To paraphrase the author, ‘no technology (yet available) can detect evidence inside someone’s mind.’  

That is not to say Montes and the DI didn’t make mistakes that, if detected and pursued, might have resulted in her exposure.  Complacency and operational friction can, especially in an operation lasting so long, mitigate against discipline and sound tradecraft.  For instance, although she returned from Cuba in 1985 a recruited agent, that did not mean Montes had fully acclimated herself to the demands a secret life exacted.  Shortly thereafter, she erred in telling Mimi she had visited the island.  Realizing what she had done, Montes subsequently broke all contact with her old friend who, it turned out, had assumed Montes had travelled there on behalf of DIA.  This was, as Lapp recounts, not the only alerting behavior Montes and the DI engaged in over the course of her time as a spy. 

Others included:

  • Montes’s refusal of jobs offering increased responsibility for fear of losing access to information of interest to Cuba.

  • Her weekly meetings with her handler for lengthy lunches in the same Chinese restaurant in Washington.  Per Lapp, the Bureau – which thought such direct personal contact too dangerous to risk – did not consider the possibility the DI might be hiding in plain sight.  The DI, conversely, likely calculated that casual observers would write off a Hispanic male and female seen dining together as what it appeared to be.

  • Her handler waving Montes down on the street to make emergency contact with her in the wake of the 1996 Cuban shoot-down of an aircraft flown by the exile group ‘Brothers to the Rescue’.  Montes met with her handler every night during the crisis, providing him with read-outs on the US response to it.  This extensive contact with the DI increased the potential risk of detection.

  • A phone call – probably by the DI – to Montes during a Pentagon meeting on the shoot-down crisis.  That call, and Montes’s consequent precipitous departure from the session, drew the attention of DIA colleagues including a counterintelligence (CI) officer who presciently concluded: “She’s no good.  If I’m right, it’s bad, real bad.”

  • Montes’s denial, in a resulting interview, that the phone call had even occurred.  In that interview, conducted by the author of another book on the case, Montes handled other probing questions well, leading the interviewer to conclude she had, perhaps, denied the call occurred because she was embarrassed to speak of it as it involved a private matter.

  • The soft-pedaling by Montes of the threat posed by the Cubans and her down-playing of the malevolence of the Havana regime raised concerns among some of her DIA colleagues.  But this was ultimately ascribed to legitimate analytical disagreement.

  • The 1998 recall of her handler to Cuba because he was “too close to the Wasp Network.”  This was, as Lapp writes, bad tradecraft as it linked different operations, potentially jeopardizing both should one or the other be compromised.

  • Trips by Montes to the Caribbean every six months after her handler’s recall to meet her new Cuban contacts.  This pattern of ostensible “vacation” travel should have been alerting to CI personnel.

  • And the fact, as Lapp establishes, that compartmentation of information regarding “Sonia” within the DI was poor; too many people knew her real name and about her activities.

Investigation of some of these oddities might, Lapp concludes, have put Montes at risk of detection.  But they were largely ignored or discounted because, Lapp concludes, she herself was viewed as odd.   A “vicious bureaucratic infighter”, Montes “was intellectually arrogant…(and)…a bully during meetings”. Her expertise, Lapp writes, made Montes “cocky to the point that her coworkers hated her”.  Co-workers called her “la ostra” (the outsider).  The views of her co-workers notwithstanding, Lapp observes that, on paper, Montes was “the model” employee.  She worked long hours, writing on the Cuban “political environment, the stability of the regime, the accumulation of new weaponry”, etc. “Highly respected and…(having)…moved on up quickly,” Montes was seen by her superiors as being good at her job and was given broad access to the full range of intelligence on Cuba to do it.  Moreover, she had passed a polygraph exam.  Finally, the fact that female spies are a relatively rarity also mitigated against Montes coming under CI scrutiny.

Lapp describes the loneliness, stress and anxiety that plagued Montes.  She could not, Lapp judges, maintain friendships at work, because “she saw the US government as an enemy…(and)…disagreed with what they did for a living.”  Consequently, “instead of hanging out with her co-workers,” Lapp deduces, “she socialized with her handlers; she saw them as friends”.  Attempts by Montes to find companionship in the form of a “Mr. X” provided by the DI at her request and a relationship with DIA colleague – “Roger” – whom she may have seen as an escape route from her in stressful life as a spy – are well documented by Lapp.  Both of those quests for love went unrequited.  “Mr. X” evoked “no spark”, and Roger – her ultimate deception of him aside – grew increasingly estranged from a woman whose attention and emotional attachment were directed elsewhere.

Lapp’s explication of his involvement in the counterespionage investigation that led to Montes will be the most illuminating part of the book for general readers. That investigation was – as virtually all successful counterespionage investigations are – facilitated by information delivered to the US from the heart of the adversary service.  In Lapp’s words: “spies catch spies.”  Even with such assistance, hunting a spy involves knitting often seemingly disparate, sometimes partial and all too often false pieces of information together into first a plausible; and later – as leads and theories are run to ground – verifiable; and, finally, a provable narrative.  As Lapp explains, there were several indicators that spurred the Montes investigation.  These included: information from a Cuban intelligence officer who defected in 1989 that a colleague told him he was handling two American agents, both women; and – in a coup reminiscent of the VENONA project – information from other Cuban defectors that granted the FBI the ability to read encrypted high frequency radio traffic sent by the DI to it agents in the US for what Lapp describes as a “brief period in 1996-1997”.

With the assistance of NSA, the FBI could read “a couple-dozen” messages the Cubans sent to a designated person, who the FBI would later learn was Montes’s handler.  Those messages contained clues regarding an agent the DI called “Agent S” or “Sergio”.  Among those hints was information indicating that Agent S had purchased a “Tandy” laptop computer at a store in “Alexandria” (presumed to be the Virginia city by that name based upon the range of the DI radio broadcast); reference to the agent’s travel to Guantanamo in the mid-1990’s; a report that the agent was in touch with a certain “WD”; mention of the agent using a SAFE system (a computer system the FBI would learn was used by DIA); indication that the agent passing information to the DI on floppy discs; information on the agent having had access to a specific CIA document and having travelled to Cuba at a certain time; and the password for the agent’s laptop: “NELEBAINOS”. 

As Lapp makes clear, espionage investigations never proceed as envisioned.  In this instance, investigators pursued false leads (e.g. the assumption that “Sergio” was male when, in fact, the Cubans had used a male name for their agent “Sonia” in an effort to mislead any hostile person gaining access to messages on the case), suffered from the inevitable “humbling” errors inherent in any such endeavor (e.g. when they realized the computer password contained part of Montes’s full true name and her work name spelled backwards), and were plagued at key moments by the proverbial “Murphy” (notably in the course of their initial attempt to covertly enter Montes’s apartment).  I won’t spoil Lapp’s telling of how the investigation eventually identified Montes as a spy here.  Suffice it to say it is both informative and entertaining. 

One aspect of Lapp’s description of the conduct of the investigation bears mentioning.  Lapp’s rightful pride in the FBI and in the people he worked with, his frankness in addressing past mistakes the Bureau has made (to include such episodes as the wrongful focus on CIA officer Brian Kelley as a suspected Russian spy and the abuse to the FISA process in the Carter Page case), and his determination not to repeat them in the course of this investigation make his narrative even more compelling.

The denouement of the story – Lapp’s debriefing as part of Montes’s sentencing agreement – is a particularly gripping read.  Addressing the “what, when, where and how” of her spying with Montes was a relatively straightforward task for Lapp and his colleagues.  As is always the case in such circumstances, the biggest challenge was determining why Montes betrayed her country.  Born into a military family, her parents were both of Puerto Rican heritage, but not political.  Much has been made of Montes’s resentment of her US Army doctor father, whom she has portrayed as authoritarian and abusive as a factor in her spying.  Lapp cites an IC psychological assessment’s conclusion that “Montes’s childhood made her intolerant to power differentials, led her to identify with the less powerful and solidified her desire to retaliate against authoritarian figures.”  That may well be true.  But, as Lapp makes clear by citing his own background, not everyone with a difficult upbringing becomes a spy.  Lapp’s own conclusion – that Montes was a narcissist; coldly indifferent to the impact her actions had on those around her and all too ready to blame others – makes sense.  It also helps explain why Lapp came to hate her as their time together went on.

I found two aspects of Lapp’s recounting of his debriefing of Montes especially interesting for what it said about her true nature.  The first concerns a trip Montes took to Central America at the behest of DIA in early 1987.  Lapp makes a good case that the trip gave Montes access to information she passed to the DI that ultimately resulted in the death of Green Beret S/SGT Gregory Fronius in a rebel attack in El Salvador late that same year.  Lapp found her answer of “I don’t remember” to his question of whether she met Fronius during that trip unconvincing.  But her comment “that if she had, in fact, been responsible for his death, it was his own fault” because he had joined the US military and understood the risk was particularly damning. 

Concern that Montes might share US military plans for responding to 9/11 terror attack with the Cubans, was the determining factor in the decision by the Department of Justice and FBI to arrest her.  During her debriefing, Lapp asked Montes whether she would have passed the DI the US war plans if she’d had an opportunity to do so.  Her reply; that she would have as “she believed she had a moral right to tell the Cubans how we fought a modern war in case we attacked Cuba;” was not surprising.  But her follow-up remark that if Cuba gave the plans to Al-Qa’ida or the Taliban and it resulted in the deaths of more Americans, “Then that’s the risk they took” was jarring for what it said about her cold-bloodedness.

As is always the case in such instances – one need only think of John Walker’s exploitation of children, Harold Nicholson’s attempt to use his son to re-contact the Russians, and Robert Hanssen’s reprehensible treatment of his wife, Bonnie – Montes’s deceit resulted in family tragedy.  Accordingly, Lapp conveys the damage Montes’s deception and betrayal did to her siblings and her mother.  As Lapp relates, the former released a statement disavowing their sister’s “treason against this country and the people of our nation” while the latter – at first reluctant to acknowledge the truth – later sent a heartrending letter to her daughter detailing the disappointment and grief she felt on learning the allegations were true.  As for Montes herself, her devotion to the Cuban cause would prove abiding.  Even after a lengthy prison term, Lapp writes, she showed no remorse.

Lapp’s book gives the reader unique insight into the Montes case and will be of great interest to intelligence professionals and amateurs alike.  The story he tells serves as a reminder that, even in the cyber age, a disciplined agent being run by a professional intelligence service using basic tradecraft can wreak great havoc.  I hope today’s CI professional are paying attention.

Queen of Cuba earns a solid three out of four trench coats.