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Ana Belén Montes
Ana Belén Montes on the right. Photo: Defense Intelligence Agency

Meet Ana Belén Montes, a former spy for Cuba, now retired in Puerto Rico

After serving a 20-year sentence in federal prison, Montes will spend her retirement back home.

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Ana Belén Montes, a Puerto Rican woman perched at high FBI echelons and who was convicted for spying on behalf of Cuba, was released on Sunday, Jan. 9. 

Montes, 65,  was originally sentenced to 25 years in federal jail but only served 21.

After doing time in Fort Worth, Texas, Montes settled in Puerto Rico, where she’ll reportedly spend the rest of her retirement. 

“I am more than happy to touch Puerto Rican soil again,” Montes said through her attorney. 

“After two rather exhausting decades and faced with the need to earn a living again, I would like to dedicate myself to a quiet and private life. So, I will not participate in any media activity.” 

The story behind Montes is startling as it is arresting.

She was a clerical worker at the Department of Justice in 1984, the FBI archives say, where she apparently seized the attention of Cuban officials because she so often repudiated U.S. treatment of Cuba through their policies. 

It should be noted that after a 20-year punishment, Montes maintains her activist mindset, going so far as to “encourage those who wish to focus on me to focus instead on important issues, such as the serious problems facing the Puerto Rican people or the U.S. economic embargo against Cuba,” another part of her statement read. 

In 1985, Montes applied to work at the Defense Intelligence Agency (DIA), a studious branch of the Pentagon that, as its name suggests, combines defense and intelligence to devise strategy, response, and even policy related to national intelligence. 

Rapidly climbing ranks, Montes went on to become the agency’s top Cuba analyst for the DIA, already a “fully recruited spy,” according to archival records. 

But within the agency — despite the fact some officials trace her espionage to her clerical days — she was top-notch on Cuba. A polygraph test also helped to dispel concerns. 

Even then, colleagues and security officials had expressed concerns, given her views on the U.S.-Cuba relationship, one of the longstanding political contracts that capture American control over the Caribbean, perhaps only rivaled by Puerto Rico. 

It was a challenging proposition for Montes, who did not make a digital record or paper trail that would connect her espionage endeavor to her role at DIA. Instead, Montes made a mental note of encoded messages she received via intelligence, which she, in turn, decoded on a personal laptop. 

As instructions filtered through Montes and filtered in her home, she would meet with a “handler,” to whom she’d turn over the data.

In 1996, the veil over her scheme began to unravel. 

A colleague, acting on instinct, let an official know that Montes was working undercover for the Cubans, and although she was interrogated, she did not admit to wrongdoing. 

That initial report was shelved and largely forgotten about until the same interrogating officer — four years later — learned that an “unidentified Cuban agent” had been active in D.C., and an official probe was activated. 

Eventually, after spying on the spy, the FBI believed it had enough evidence to build a case against Montes but wanted to hold off until she and the “handler” arranged a meeting, which apparently took too long and never happened. 

It wasn’t until the tragic events of 9/11 that the FBI ordered her arrest since the agency did not want Montes involved in work related to U.S. war plans, the FBI archives say. 

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In September of 2001, Montes was arrested, and in 2002, she struck a plea deal with federal prosecutors, having admitted her crimes. 

Montes admitted to revealing the identities of four Cuba-based undercover U.S. agents to Cuban authorities, though, at the time, federal prosecutors said the agents whose identities were disclosed were not harmed. 

Federal prosecutors also accused Montes of sharing highly-classified material, and the level of sensitivity surrounding them was so high that details could not be shared with the public. 

“Your honor, I engaged in the activity that brought me before you because I obeyed my conscience rather than the law,” Montes said at trial. 

“I believe our government’s policy, towards Cuba, is cruel and unfair, profoundly unneighborly, and I felt morally obligated to help the island defend itself from our efforts to impose our values and our political system on it.”

What little is known from the court records is that Montes provided documentation that contained details about U.S. surveillance of Cuban weapons. 

Ricardo Urbina, the presiding judge over Montes’s case, in his ruling, wrote she had put U.S. citizens and the “nation as a whole” at risk. 

Years ahead of her incarceration, Montes requested parole from the Obama administration as part of prisoner exchange agreements with Cuban, but withdrew from consideration in the Trump years. 

Montes’ freedom terms include a five-year supervised release, monitored internet access, and a ban from government work and contacting foreign agents without supervision.

And what did Montes have to say about her crimes, specifically, after spending 21 years in jail?

“Who in the last 60 years has asked the Cuban people if they want the U.S. to impose a suffocating embargo that makes them suffer? The pressing need for global cooperation that will stop and reverse the destruction of our environment also deserves attention. As a person, I am irrelevant. I am not important, while there are serious problems in our global homeland that demand attention and a demonstration of brotherly love.”

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