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A most dangerous spy

by Jim Popkin

The Washington Post

Ana Montes has been locked up for a decade with some of the most frightening women in America. Once a highly decorated U.S. intelligence analyst with a two-bedroom co-op in Washington, Montes today lives in a two-bunk cell in the highest-security women’s prison in the nation.

Her neighbors have included a former homemaker who strangled a pregnant woman to get her baby, a longtime nurse who killed four patients with massive injections of adrenaline, and Lynette “Squeaky” Fromme, the Charles Manson groupie who tried to assassinate President Gerald Ford.

But hard time in the Lizzie Borden ward of a Texas prison hasn’t softened the former Defense Department wunderkind. Years after she was caught spying for Cuba, Montes remains defiant. “Prison is one of the last places I would have ever chosen to be in, but some things in life are worth going to prison for,” Montes writes in a 14-page handwritten letter to a relative. “Or worth doing and then killing yourself before you have to spend too much time in prison.”

Like Aldrich Ames and Robert Hanssen before her, Ana Montes blindsided the intelligence community with brazen acts of treason. By day, she was a buttoned-down GS-14 in a Defense Intelligence Agency cubicle. By night, she was on the clock for Fidel Castro, listening to coded messages over shortwave radio, passing encrypted files to handlers in crowded restaurants and slipping undetected into Cuba wearing a wig and clutching a phony passport.

Montes spied for 17 years, patiently, methodically. She passed along so many secrets about her colleagues — and the advanced eavesdropping platforms that American spooks had covertly installed in Cuba — that intelligence experts consider her among the most harmful spies in recent memory. But Montes, now 56, did not deceive just her nation and her colleagues. She also betrayed her brother Tito, an FBI special agent; her former boyfriend Roger Corneretto, a Cuban-intelligence officer for the Pentagon; and her sister, Lucy, a 28-year veteran of the FBI who has won awards for helping to unmask Cuban spies.

In the days after the Sept. 11, 2001, terrorist attacks, the FBI’s Miami field office was on high alert. Most of the hijackers had spent time in South Florida, and FBI personnel there were desperate to learn whether any more had stayed behind. So when a supervisor asked Lucy Montes to come to his office, she didn’t blink. Lucy was a veteran FBI language analyst who translated wiretaps and other sensitive communications.

But this impromptu meeting had nothing to do with Sept. 11. An FBI squad leader sat Lucy down. Your sister, Ana, has been arrested for espionage, he informed her, and she could face the death penalty. Your sister, Ana, is a Cuban spy.

Lucy didn’t scream, didn’t storm out in disbelief. Instead, she found the news strangely reassuring. “I believed it right away,” she recalled in a recent interview. “It explained a lot of things.”

Major news organizations reported on the arrest, of course, but it was overshadowed by nonstop coverage of the terrorist attacks. Today, Ana Montes remains the most important spy you’ve never heard of.

Born on a U.S. Army base in 1957, Ana Montes is the eldest child of Emilia and Alberto Montes. Puerto Rico-born Alberto was a respected army doctor, and the family moved frequently, from Germany to Kansas to Iowa. They settled in Towson, Maryland, outside Baltimore, where Alberto developed a successful private psychiatric practice and Emilia became a leader in the local Puerto Rican community.

Ana thrived in Maryland. Slender, bookish and witty, she graduated with a 3.9 GPA from Loch Raven High School, where she noted in her senior yearbook that her favorite things included “summer, beaches … chocolate chip cookies, having a good time with fun people.” But the bubblegum sentimentality masked a growing emotional distance, grandiose feelings of superiority and a troubling family secret.

To outsiders, Alberto was a caring and well-educated father of four. But behind closed doors, he was short-tempered and bullied his children. Alberto “happened to believe that he had the right to beat his kids,” Ana would later tell CIA psychologists. “He was the king of the castle and demanded complete and total obedience.” The beatings started at 5, Lucy said. “My father had a violent temper,” she said. “We got it with the belt. When he got angry. Sure.”

Ana’s mother feared taking on her mercurial husband, but as the verbal and physical abuse persisted, she divorced him and gained custody of their children.

Ana was 15 when her parents separated, but the damage had been done. “Montes’ childhood made her intolerant of power differentials, led her to identify with the less powerful, and solidified her desire to retaliate against authoritarian figures,” the CIA wrote in a psychological profile of Montes labeled “Secret.”

Her “arrested psychological development” and the abuse she suffered at the hands of a temperamental man she associated with the U.S. military “increased her vulnerability to recruitment by a foreign intelligence service,” adds the 10-page report. Lucy recalls that even as a teenager, Ana was distant and judgmental. “We were only a year apart, but I have to tell you that I never really felt close to her,” Lucy said. “She wasn’t one that wanted to share things or talk about things.”

Ana Montes was a junior at the University of Virginia when she met a handsome student during a study-abroad program in Spain. He was from Argentina and a leftist, friends recall, and helped open Montes’ eyes to the U.S. government’s support of authoritarian regimes. Spain had become a hotbed of political radicalism, and the frequent anti-American protests offered a welcome diversion from schoolwork. “After every protest, Ana used to explain to me the ‘atrocities’ that the U.S. government used to do to other countries,” recalls Ana Coln, a fellow college student who befriended Montes in Spain in 1977 and now lives near Gaithersburg, Maryland. “She was already so torn. She did not want to be American but was.”

After college, Montes moved briefly to Puerto Rico but could not find suitable work. When a friend told her about an opening as a clerk typist at the Department of Justice in Washington, she put her political considerations aside. A job was a job.

Montes excelled at the DOJ’s Office of Privacy and Information Appeals. Less than a year later, after an FBI background check, the Department of Justice granted Montes top-secret security clearance. She could now review some of the DOJ’s most sensitive files.

While holding down her day job, Montes began pursuing a master’s degree at the School of Advanced International Studies at Johns Hopkins University. Her political views hardened. Montes developed a hatred for the Reagan administration’s policies in Latin America and especially for U.S. support of the contras, the rebels fighting the communist Sandinista government in Nicaragua.

Montes was now a budding Washington bureaucrat and a full-time student at one of the country’s premier universities. But she was about to take on another demanding assignment: spy in training. In 1984, the Cuban intelligence service recruited her as a full-blown agent.

Sources close to the case think that a friend at SAIS served as a facilitator for the Cubans, helping to identify potential spies. Cuba considers recruiting at American universities a “top priority,” according to former Cuban intelligence agent Jose Cohen, who wrote in an academic paper that the Cuban intelligence service identifies politically driven students at leading U.S. colleges who will “occupy positions of importance in the private sector and in the government.”

Montes must have seemed a godsend. She was a leftist with a soft spot for bullied nations. She was bilingual and had dazzled her DOJ supervisors with her ambition and smarts. But most important, she had top-secret security clearance and was on the inside. “I hadn’t thought about actually doing anything until I was propositioned,” Montes would later admit to investigators. The Cubans, she revealed, “tried to appeal to my conviction that what I was doing was right.”

CIA analysts interpret the recruitment a bit more darkly. Montes was manipulated into believing that Cuba desperately needed her help, “empowering her and stroking her narcissism,” the CIA wrote. The Cubans started slowly, asking for translations and bits of harmless intel that might assist the Sandinistas, her pet cause. “Her handlers, with her unwitting assistance, assessed her vulnerabilities and exploited her psychological needs, ideology, and personality pathology to recruit her and keep her motivated to work for Havana,” the CIA concluded.

Montes secretly visited Cuba in 1985 and then, as instructed, began applying for government positions that would grant her greater access to classified information. She accepted a job at the Defense Intelligence Agency, the Pentagon’s major producer of foreign military intelligence.

In an early mistake, Montes had confided to her old friend from Spain, Ana Coln, that she had visited Cuba and had had a fling with the cute guy who toured her around the island. Montes also revealed that she was about to take a DIA job. “I was dumbfounded,” Coln recalled. “I couldn’t understand why somebody with her leftist beliefs would be willing to work for the U.S.A. government and for the military.” Montes said she wanted to be part of the political action and was “an American girl, after all.” But days after the confession, Montes cut her girlfriend off. Coln called and wrote letter after letter for 2½ years, to no avail. Montes wouldn’t engage. Coln never heard from Montes again.

Back in Miami, Lucy Montes also was puzzled by her sister’s decision to work for the Defense Department. But she loved her sister and was so eager to make a connection that she didn’t press the point. Ana had become more introverted and rigid in her views since joining DIA. “She would talk to me less and less about things that were going on with her,” Lucy said.

Ironically, Ana now had much in common with her siblings. Although Juan Carlos, the baby of the family, had become a deli owner in Miami, Lucy and her other brother, Alberto “Tito” Montes, had chosen careers helping to protect the United States. Tito had become an FBI special agent in Atlanta, where he still works, and his wife was an FBI agent. Lucy had become an FBI Spanish-language analyst in Miami, a job she still holds, frequently working on cases involving Cubans. Her husband at the time worked for the FBI, too.

Of her family members, only Lucy would be interviewed. She agreed to talk for the first time — more than a decade after her sister’s arrest — to make her views on Ana clear. “I don’t feel the way that a lot of her friends seem to feel, like there’s a good excuse for what she did, or I can understand why she did it, or, you know, what this country did is wrong. There’s nothing to be admired,” Lucy said.

For the next 16 years, Ana Montes excelled — in both Washington and Havana. Hired by the DIA as an entry-level research specialist, she was promoted again and again. Montes quickly became DIA’s principal analyst for El Salvador and Nicaragua, and later was named the DIA’s top political and military analyst for Cuba. In the intelligence community and at DIA headquarters, Montes became known as “the Queen of Cuba.” Not only was she one of the U.S. government’s shrewdest interpreters of Cuban military affairs — hardly surprising, given her inside knowledge — but she also proved adept at shaping (and often softening) U.S. policy toward the island nation.

Over her meteoric career, Montes received cash bonuses and 10 special recognitions for her work, including a certificate of distinction that George Tenet, then the CIA director, presented her in 1997. The Cubans also awarded their star student with a medal, a private token of appreciation that Montes could never take home.

She became a model of efficiency, a warrior monk embedded deep within the bureaucracy. From cubicle C6-146A at DIA headquarters at Joint Base Anacostia-Bolling in Washington, she gained access to hundreds of thousands of classified documents, typically taking lunch at her desk absorbed in quiet memorization of page after page of the latest briefings. Colleagues recall that she could be playful and charming, especially with bosses or when trying to talk her way into a classified briefing. But she also could be arrogant and declined most social invitations.

Montes would clock out at DIA, then start her second job at her Macomb Street apartment. She never risked taking a document home. Instead, she fastidiously memorized by day and typed in the evenings, spewing whole documents into a Toshiba laptop. Night after night, she poured years’ worth of highly classified secrets onto cheap floppy disks bought at Radio Shack.

Her tradecraft was classic. In Havana, agents with the Cuban intelligence service taught Montes how to slip packages to agents innocuously, how to communicate safely in code and how to disappear if needed. They even taught Montes how to fake her way through a polygraph test. She later told investigators it involves the strategic tensing of the sphincter muscles. It’s unknown if the ploy worked, but Montes did pass a DIA-administered polygraph in 1994, after a decade of spying.

Montes got most of her orders the same way spies have since the Cold War: through numeric messages transmitted anonymously over shortwave radio. She would tune a Sony radio to AM frequency 7887 kHz, then wait for the “numbers station” broadcast to begin. A female voice would cut through the otherworldly static, declaring, “Atencin! Atencin!” then spew out 150 numbers into the night. “Tres-cero-uno-cero-siete, dos-cuatro-seis-dos-cuatro,” the voice would drone. Montes would key the digits into her computer, and a Cuban-installed decryption program would convert the numbers into Spanish-language text.

Montes also took the unusual risk of meeting the Cubans face-to-face. Every few weeks, she would dine with her handlers in Washington-area Chinese restaurants, where Montes would slide a fresh batch of encrypted diskettes past tiny dishes of delicacies. The clandestine handoffs also took place during Montes’ vacations, on sunny Caribbean islands.

Montes even traveled to Cuba four times for sessions with Cuba’s top intelligence officers. Twice, she used a phony Cuban passport and disguised herself in a wig, hop-scotching first to Europe to cover her tracks. Two other times she got Pentagon approval to visit Cuba on U.S. fact-finding missions. She would meet at the U.S. Interests Section in Havana during the day but slip away to brief her Cuban superiors.

Back in the U.S., when Montes needed to convey an urgent message, she reached for a pager. Montes would seek out pay phones at the National Zoo, a Metro station or by an old department store to call pager numbers controlled by the Cubans. One beeper code would mean “I’m in extreme danger”; another, “We have to meet.” Schooled in spycraft by the KGB, the Cubans relied on the storied tools of the trade.

Montes’ pager codes and shortwave-radio notes, for example, were written on specially treated paper. “The frequencies and the cheat sheet for the numbers, that was all on water-soluble paper,” explained the FBI’s Pete Lapp, one of two top agents on the case. “You throw it in the toilet, and it evaporates.”

Spying was lonely. Montes could confide only in her handlers. Family gatherings and holidays with her two FBI siblings and their FBI-employed spouses became tense affairs. At the beginning, the Cubans provided enough of a social life. “They were emotionally supportive. They understood my loneliness,” Montes told investigators. But as she turned 40, Montes became despondent. “I was finally ready to share my life with someone but was leading a double life, so I did not feel I could live happily,” she revealed. The Cubans set her up with a lover, but after a couple of days of fun, she realized she would not find happiness with a “mail order” groom.

Ana’s alienation only grew when, by strange coincidence, Lucy began working on the biggest case of her career: a massive crackdown on Cuban spies operating in the United States. It was 1998, and the Miami field office had uncovered a Cuban spy ring based in Florida, the so-called Wasp Network. More than a dozen members strong, the Wasp Network was infiltrating Cuban exile organizations and making inroads into U.S. military sites in Florida upon its capture. For Lucy, the Wasp case marked the crowning achievement of her career. The FBI had called on her to translate hours of wiretapped conversations of Cuban spies who were trying to penetrate the U.S. Southern Command base in Doral, Florida. Lucy earned praise from the FBI brass and an award from a local Latin chamber of commerce. But she never shared the news with Ana. Although Ana was one of the preeminent Cuba experts in the world and should have been ecstatic that her sister had helped expose a Cuban spy ring, Lucy was convinced Ana would just change the subject. “I knew she would have no interest in hearing about it or talking about it,” Lucy said.

But Lucy’s triumph became Ana’s despair. Ana’s handlers suddenly went dark. They refused to contact her for months as they assessed the fallout from the investigation. “Something that gave me fulfillment disappeared,” she later told investigators. Ana bottomed out. She experienced crying spells, panic attacks and insomnia. She sought psychiatric treatment and started taking antidepressants. CIA-led psychologists would later conclude that the isolation, lies and fear of capture had triggered borderline obsessive-compulsive traits. Montes began showering for long stretches with different soaps and wearing gloves when she drove her car. She strictly controlled her diet, at times eating only unseasoned boiled potatoes.

At a birthday party at Lucy’s home in 1998, Ana sat stone-faced and barely spoke. “Some of my friends thought she was very rude, that there was something seriously odd with her. And there was. She was cut off from her handler,” Lucy said.

Inside the DIA, the star analyst remained above suspicion. Montes had succeeded beyond the Cubans’ wildest dreams. She was now briefing the Joint Chiefs of Staff, the National Security Council and even the president of Nicaragua about Cuban military capabilities. She helped draft a controversial Pentagon report stating that Cuba had a “limited capacity” to harm the United States and could pose a danger to U.S. citizens only “under some circumstances.” And she was about to earn yet another promotion, this time a prestigious fellowship with the National Intelligence Council. An advisory body to the director of central intelligence, the NIC was then at CIA headquarters. Montes was about to gain access to even more treasured information. Her spy career would have reached unfathomable heights had she not been caught.

Ana Montes lives today at the Federal Medical Center Carswell in Fort Worth, in a 20-inmate unit reserved for the nation’s most dangerous female offenders. She could have been charged with treason, a capital offense, but pleaded guilty to espionage in exchange for a 25-year sentence. She still has another decade to go.

“Apparently it’s pretty horrific in there for her,” Lucy says. “She says it’s like being in an insane asylum.”

U.S. military and intelligence agencies spent years assessing the fallout from Montes’ crimes. At a congressional hearing last year, the woman in charge of the damage assessment testified that 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.”

Strict prison rules bar Montes from talking to the media and all but a few friends and relatives. But in her private correspondence, she refuses to apologize. Spying was justified, she says, because the United States “has done some things that are terribly cruel and unfair” to the Cuban government. “I owe allegiance to principles and not to any one country or government or person,” Montes writes in one letter to a teenage nephew. “I don’t owe allegiance to the U.S. or to Cuba or to Obama or to the Castro brothers or even to God.”

Lucy Montes knows all about allegiance. When Ana walks out of prison on July 1, 2023, Lucy will be waiting. She has offered to let Ana live in her home for a few months, to get settled. “There’s nothing acceptable about what she did. On the other hand I don’t feel like I can turn my back on her, because she’s my sister.”