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 Fort Worth, Texas where she was being held. Montes was in federal prison for over 20 years.
Montes freed January6, 2023, despite the date of release on the inmate aide website being January 8, 2023.
It is important to recall the damage that she did to U.S. national security, and her successful campaign as an agent of influence to downplay the threat Cuba poses to the United States, and other democracies in the region.
For example the 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 Brothers to the Rescue shootdown on February 24, 1996, and the influence operation she conducted to direct blame away from Castro, and onto the victims, first drew the attention of investigators.
Another example, she 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.”
Montes managed to be selected as a team leader to analyze the effectiveness of U.S. air force bombing in Afghanistan after the September 11th attacks in 2001. Officials, rightly feared, that with Havana’s long history of selling secrets to enemies of the United States that if Montes obtained the Pentagon’s war plans for Afghanistan, that the Castro regime would pass it on to the Taliban, and this sped up her arrest.
The full extent of the damage that she did to the United States remains mostly classified as can be seen in the highly redacted damage assessment prepared by the Office of the Inspector General of the Department of Defense published on June 16, 2005.
At a congressional hearing in 2012, the woman charged with the damage assessment testified Montes was “one of the most damaging spies in U.S. history.” “Former National Counterintelligence Executive Michelle Van Cleave told Congress that Montes ‘compromised all Cuban-focused collection programs’ used to eavesdrop on high-ranking Cubans, and it ‘is also likely that the information she passed contributed to the death and injury of American and pro-American forces in Latin America,’” reported Jim Popkin in The Washington Post in 2013.
Retired FBI agent Peter Lapp, who led the covert operation against Montes, found the “most damaging non-human intelligence she provided to the Cubans” was information about “a U.S. secret satellite program” that was so sensitive “that prosecutors were banned from using it had the case gone to trial.” Information was not related to Cuba, but investigators believe that Fidel Castro passed it on to other regime’s hostile to the United States.
Montes with her Cuban handlers conducted an influence operation so effective that even after her arrest, the misleading analysis she provided continued to be repeated by policymakers. Her claim that Cuba posed no threat to the United States continued to circulate in government a decade after her arrest, and was used as the basis to request that President Obama remove Cuba from the list of state terror sponsors in 2013.
“The damage done by Ana Belen Montes to both U.S. National Security and in the formulation of U.S. Foreign policy cannot be underestimated, nor the reality that she was not alone in infiltrating the U.S. government to work for a foreign power. American allies and friends and at least one American soldier were killed by the treachery committed by this foreign agent. Furthermore, the disinformation provided by her DI handlers that she inserted in U.S. government reports continued to have an impact on policy long after she went to prison,” observed Ambassador Otto J. Reich, currently a member of the board of the Center for a Free Cuba and former Assistant Secretary of State and member of the National Security Council staff.
She was not the only one to penetrate the highest levels of the United States national security apparatus.
Ambassador Victor Manuel Rocha was indicted on December 5, 2023 on charges of conspiring to act as a spy for the Cuban dictatorship, and a traitor against the United States over 40 years. He began his career at the State Department, holding important postings in Bolivia, Argentina, Honduras, Mexico, the Dominican Republic, and Cuba. Later, he worked as a private consultant for the US Southern Command, which oversees Cuba. The Associated Press reports that “Federal authorities have been conducting a confidential damage assessment that could take years to complete,” and when discovered, much of it will remain classified, and unavailable to the public. Rocha pleaded guilty, and was sentenced on April 12, 2024 to 15 years in federal prison and fined $500,000. Prosecutors dropped over a dozen other offenses, including making false statements and wire fraud, in return.
Notes from the Cuban Exile Quarter, September 21, 2026
Ana Belen Montes was arrested 25 years ago for spying for the Castro dictatorship at the highest levels of the Pentagon. She got Americans killed.
She was not the only one recruited by Cuban intelligence.
The Cuban dictatorship, primarily through its intelligence services such as the General Directorate of Intelligence (DGI, now known as the Cuban Intelligence Services or CuIS), has engaged in targeted efforts to influence and infiltrate U.S. higher education institutions for over six decades.
These activities have focused on espionage, recruitment of agents of influence, and the acquisition of sensitive information or expertise. This has been a long-standing strategy, dating back to the Cold War era, with operations continuing to the present day.
Key Methods of Influence and Recruitment
Cuban intelligence prioritizes universities for their access to emerging leaders, researchers, and unclassified but valuable data (e.g., in science, policy, or technology).
Common tactics include:
- Ideological grooming and mentorship: Approaching idealistic or vulnerable students (often via cultural events, study abroad, or leftist student groups) with promises of revolutionary ideals, economic incentives post-embargo, or blackmail. Professors or academic mentors are recruited to “spot and assess” promising individuals.
- Clandestine operations: Using encrypted communications, dead drops, or intermediaries (e.g., via the Cuban Mission to the UN or cultural centers) to avoid detection. Recruits may be tasked with sharing research, influencing peers, or accessing classified info later in their careers.
- Exploiting exchanges: Leveraging academic programs or delegations to embed officers or identify targets during visits.
These efforts are low-cost and ideology-driven rather than financially motivated, appealing to anti-imperialist sentiments.
Reuters, January 6, 2023
Cuba spy Ana Belen Montes released after 20 years behind bars
(Reuters) – Ana Belen Montes, one of the highest-ranking U.S. officials ever proven to have spied for Cuba, has been released from prison early, the U.S. Bureau of Prisons confirmed Friday, after she spent more than two decades behind bars.
Montes, 65, had in 2002 pleaded guilty to conspiracy to commit espionage after she was accused of using her leading position as a Defense Intelligence Agency (DIA) official to leak information, including identities of some U.S. spies, to Havana.
Aged 45, she was sentenced to 25 years in prison.
A U.S. citizen of Puerto Rican descent, Montes began working for the DIA in 1985 and rapidly climbed its ranks to become the agency’s top Cuba analyst.
Prosecutors said during this time Montes received coded messages from Havana over a short-wave radio as strings of numbers, which she would type onto a decryption-equipped laptop to translate to text.
She was accused of supplying the identity of four U.S. spies to Cuba, as well as other classified information.
Montes was arrested on Sept. 21, 2001, shortly before the United States invaded Afghanistan. Her lawyer, a leading espionage specialist, had argued she had cooperated without reservation.
At her sentencing a year later, Montes argued that she had obeyed her conscience and that U.S. policy to Cuba was cruel and unfair. “I felt morally obligated to help the island defend itself from our efforts to impose our values and our political system on it,” she said.
Ricardo Urbina, the sentencing judge, ruled she put fellow U.S. citizens and the “nation as a whole” at risk.
On her release from prison, Urbino had ordered Montes should be placed under supervision for five years, with her internet access monitored and a ban from working for governments and contacting foreign agents without permission.
Under President Joe Biden, the United States has eased some sanctions on Cuba but maintained its Cold War-era embargo on the island and stepped up restrictions on illegal migrants, arriving in record levels amid raging inflation and medicine shortages.
(Reporting by Sarah Morland and Eric Beech; Editing by Simon Cameron-Moore)
https://news.yahoo.com/cuba-spy-ana-belen-montes-024336738.html?ref=upstract.com