Written by Jim Arvantes

Ana Montes had two jobs during a long and illustrious career with one of this nation’s most preeminent intelligence agencies.

In her official capacity, Montes, a former Cleveland Park resident, worked as a high-level analyst for the Defense Intelligence Agency, or DIA, the intelligence arm for the U.S. military.

In her other role, Montes secretly spied for the Cuban government for 17 years, turning over troves of secret and top-secret information to her Cuban handlers —  classified information used to thwart American intelligence efforts in Cuba and elsewhere. 

During her long career as a Cuban spy, Montes became one of the most damaging and dangerous turncoats in American history, an operative who identified undercover U.S. agents while revealing the existence of current and planned U.S. covert operations in Cuba and other countries. This included the existence of a multi-billion-dollar stealth satellite called Misty, which secretly gathered vital intelligence information from Russia, China, Iran and other U.S. adversaries. 

As a spy for the Cubans, Montes “forever destroyed all of our covert plans in Cuba,” according to Jim Popkin, author of the highly acclaimed book, Code Name Blue Wren: The True Story of American’s Most Dangerous Female Spy and the Sister She Betrayed.

Popkin, a former senior producer and correspondent for NBC News, discussed the life and times of Ana Montes during a Tuesday Talk presentation at the Cleveland Park Library on Oct. 17, a talk attended by more than 150 people in the library’s main meeting room.

Even though Montes was a highly significant spy, many people have never heard of her.

Popkin, who formerly ran the investigative unit at NBC News, pointed out that Montes was arrested 10 days after 9/11 in 2001. As a result, “her story got lost in the shuffle,” said Popkin, whose book was released on January 3, three days before Montes’ parole from prison after more than two decades behind bars.

“At the time of her arrest, I was covering the FBI and 9/11,” remembered Popkin, who has won four national Emmy Awards for outstanding journalism as well as two Edward R. Murrow awards and a George Polk award. “That was our priority so we never did a story.”

‘For The Love of Cause’

During his talk, Popkin stressed that Montes spied for ideological reasons, not for financial gain, making her different than many other spies in recent U.S. history who betrayed their country for money.

“During her 17-year career Ana probably took less than $10,000 and all of that was for expenses – her car, her laptop,” said Popkin, who has appeared on the Today Show, MSNBC and CNBC. “The Cubans paid for some (school) tuition, but that was it. Money was never her motivation. She did it for love of cause.”

Popkin noted that the Ana Montes saga was driven by cruel twists and turns that made her story truly unique. Montes, for example, lived for many years on Macomb Street in the heart of Cleveland Park, the same street that’s home to the Cleveland Park Library.

“What are the chances that here we are (at the library) on Macomb Street and Ana Montes, a convicted Cuban spy, lived right up the street at 3039 Macomb Street?” Popkin asked rhetorically.

Montes served her prison sentence at the Carswell federal prison facility in Fort Worth, Tex. As part of her sentence, Montes was not allowed to talk to the press or reporters about her case so Popkin turned for information to her former cellmate at Carswell — Lynette “Squeaky” Fromme – a member of the infamous Manson family gang. Fromme served a 34-year prison term for aiming a pistol at President Gerald Ford in a failed assassination attempt in September 1975.

“Carswell is a very, very restricted place,” explained Popkin, who has written for the Washington Post, Wired, Slate and National Public Radio. “It is kind of the super-max prison for women in the federal system.”

Fromme was released from prison in 2009, and Popkin tracked her down in New York State where she now resides.

“We were talking about Ana, and one of things she said to me was ‘Ana had a lot of rules on her – she had more restrictions on her than I did,’” recalled Popkin.

That last remark by Squeaky Fromme resonated with Popkin, prompting him to ponder the Ana Montes story even more deeply and seek out Ana’s family members and friends for in-depth interviews. Montes was, by outside appearances, an upstanding citizen.

She was the daughter of a U.S. Army Colonel, a graduate of the University of Virginia, and the School of Advanced International Studies, SAIS, at Johns Hopkins University. 

Montes also earned numerous promotions and awards while working for DIA. Yet, she ended up with “more restrictions than Squeaky Fromme,” said Popkin, his voice dripping with irony.

Popkin’s own involvement with the Ana Montes story came about as a result of some unusual circumstances. Popkin’s friend and former college roommate, John Bredar, called Popkin a few days after Montes’ arrest to tell him that Montes had bought his condo from him years earlier and lived there while she spied for the Cubans. 

Popkin had spent hours in that very condo on Macomb Street while visiting his friend John. 

“It was unit 20,” remembered Popkin, who spoke before an audience that included residents of Cleveland and Woodley Parks. “If you know that building, it is a big red brick building. Her apartment was on the second floor.” 

Popkin’s bizarre connection to Montes’ condo connected and rooted him to the story, and it eventually became his obsession. When researching and writing about Ana Montes, Popkin delved into her personal and professional life, looking for key turning points to find out why she became a spy.

But before recounting Montes’ life, Popkin described a typical work day in the existence of Ana Montes, the Cuban spy. During the work week, Montes drove from her Cleveland Park apartment to DIA headquarters at Joint Base Anacostia-Bolling in Washington, D.C. on the banks of the Potomac River, riding along in her little, red Toyota Echo.

While at work, she stayed at her desk for most of the day, writing reports while also reading and memorizing classified documents. Montes had a good, but not great memory, according to Popkin.

While working on his book, Popkin became acquainted with Montes’ sister, Lucy, who coincidentally worked for the FBI the entire time that her sister, Ana, spied for Cuba. Lucy, who didn’t realize Ana was a spy until the day of her arrest, allowed Popkin to go through Ana’s personal library post-arrest. Popkin found Ana’s book, Your Memory: How it Works and How to Improve It with certain passages underlined.

Montes typically ate lunch at her desk. Even though no one knew it at the time, Montes loathed the U.S. military and what it represents, while harboring a profound dislike for her colleagues, especially those in uniform, said Popkin.

Montes worked diligently all day before leaving at 4:30 or 5 p.m. When she returned to her condo on Macomb Street, Montes started her second job, regurgitating information she gathered that particular day.

The Cubans bought Montes a used Toshiba laptop, equipping it with special software that encrypted everything she wrote. She put the information onto CD-Roms and would later pass them to her Cuban handlers. 

Montes also listened to a shortwave radio, picking up a woman broadcasting from a sound stage in Cuba who recited a series of Spanish numbers, “cinco, cinco, uno, uno, dos, dos,” calling them out in blocks of numbers, 150 at a time.

“It is a freaky kind of a sound,” said Popkin. “It is all this static, and you just hear a woman saying, ‘cinco, cinco, dos, dos, uno, uno’ over and over.”

Montes tuned in at designated times, writing the numbers down and typing them into her laptop, which would then spit out her instructions for the next several days.

Montes met regularly with her Cuban handler, often at Chinese restaurants in Northwest, Washington, where she turned over the CD-Roms loaded with classified information.

“These meetings were incredibly important to her because she was so isolated,” said Popkin.

Hollywood often glamorizes the life of spies, but spying is a very difficult and lonely life, forcing the spy to maintain a false façade and a constant vigil, Popkin pointed out.

“If you think about it, you are lying to everyone around you all the time,” said Popkin. “There are very few people you can share your secret with.”

Montes frequently visited the National Zoo, located a few blocks from her Cleveland Park condo. She also liked to jog through the streets of Cleveland Park and to exercise in local gyms.

While living in Cleveland Park, Montes maintained a small group of friends, who still remain loyal to her despite her arrest, conviction and incarceration for spying, Popkin said. 

A Spy is Born

Ana Montes did not start out as a burgeoning spy. She was born in 1957 at an army base in what was then West Germany. Both parents were from Puerto Rico, and her father was an Army physician, who later became a psychiatrist and Freudian practitioner.

Montes’ sister Lucy was born 16 months after Ana, followed by the birth of two brothers, Tito and Carlos. 

The family moved from Germany to Topeka, Kan., before eventually settling in Towson, Md., outside of Baltimore. Montes was close to Lucy growing up, but the two sisters grew apart as adults.

Popkin described their father, Alberto, as a “Freudian psychiatrist with a twist.” He had a propensity for beating his kids and his wives – he was married twice – often for the smallest of transgressions.          

Publically, he presented impeccable credentials and was held in high regard.

“He had a private life no one knew about,” commented Popkin.

Formative Years

Montes attended UVA during the mid to late 1970s, spending her junior year in Europe. While studying overseas, she met and fell in love with an Argentine student, who espoused leftist ideals, converting her to leftist causes.

After graduating from UVA, Montes worked briefly in Puerto Rico before she landed a job with the Department of Justice, DOJ, working in their Freedom of Information Office. While working at DOJ, Montes obtained a security clearance, giving her access to classified documents and information. 

In the early 1980s, Montes, who was still working for DOJ, pursued a master’s degree at SAIS, Georgetown University’s School of Advanced International Studies.

Ronald Reagan was president then, and he vowed to stop the spread of Communist regimes in Latin America. The Reagan Administration sent money and arms to an American-backed government in El Salvador, which was battling a leftist insurgency. At the same time, the Reagan Administration funneled arms and money to the Contras, who were fighting to overthrow the Communist Sandinista government in Nicaragua.

Montes, while studying at SAIS, publically and vehemently denounced American involvement in Central America, drawing the attention of a fellow student named Marta Velazquez, who also worked covertly as a spotter for Cuban intelligence. 

“Ana is a perfect recruit,” explained Popkin. “She’s an American. She works at DOJ, and she has a security clearance.”

The two women became fast friends, and Marta started giving Montes small translations to work on, bringing her in slowly. After about a year, the two women took a train trip to New York City where Montes meets a Cuban intelligence officer working out of the United Nations. He gave Montes a formal pitch, asking her, in effect, “Do you want to work for us?”

Montes said yes, becoming a full-fledged spy. 

Evening the Score

By working for the Cubans, Montes believed she was helping a small country defend itself against an aggressive colossus to the north. It was her way of trying to “equal the odds,” Popkin explained.

The Cubans helped sneak Montes into Cuba and gave her basic training and instructions in spying 101, teaching her, for example, how to communicate with the home base and how to determine if she was being followed. 

Meanwhile, Montes’ sister, Lucy, was working at a Hecht’s department store near Baltimore when she spotted a newspaper job advertisement for Spanish translators for the FBI. She applied and was hired. 

She called her sister Ana to share the exciting news, thinking her sister would be thrilled.

“She tells Ana, ‘you are not going to believe it – you work for the Justice Department and I’m going to work for the FBI – isn’t that great?’” Popkin said, recounting the phone conversation.

There was a long pause. Anna seemed horrified, and she desperately tried to talk her sister out of working for the FBI, coming up with all kinds of reasons not to work for the agency. Lucy was confused and angry, mystified at her sister’s inexplicable behavior.

The FBI assigned Lucy to Miami, a hotbed of Cuban intelligence and counter-intelligence, a posting that further infuriated sister Ana. Lucy ended up marrying an FBI agent and her brother Tito and his wife also became agents, bringing the number of Montes family members working for the FBI to four.

Popkin asked the audience to imagine a typical Montes Thanksgiving dinner with Ana sitting at a table surrounded by Lucy, an FBI translator, and three other relatives who were FBI agents. As Popkin described this scenario, the audience laughed, appreciating the irony.  

‘Queen of Cuba’       

Montes eventually got a job with the DIA as a high-level analyst, and she became very successful at her job, working on El Salvador, Nicaragua and Cuba. In fact, she became known as the “Queen of Cuba,” in intelligence circles, winning both awards and promotions and ever greater access to American secrets.

Popkin described Montes as someone who could be “lovely and very nice.” But she could also be “very, very difficult,” he said.

During her long career at DIA, a few of her colleagues voiced concerns and suspicions about her, but nothing that serious.

“She would poke her nose into things where she didn’t belong,” said Popkin. “She would go to meetings where she didn’t have a reason to be.”

The U.S. intelligence community eventually broke the Cuban codes, including the block of Spanish numbers broadcast regularly from Cuba. By deciphering the codes, DIA agents and then the FBI were able to identify and zero in on Montes as a probable Cuban spy, starting in 2000. The FBI put her under intense surveillance in May of 2001.

The FBI also secretly broke into Montes’ apartment a few times, seizing information on Montes’ laptop computer, which confirmed that she was spying for the Cubans. The information eventually convicted her.

But the FBI waited to arrest Montes, hoping to catch her in the act.

“You can’t go blabbing around town that we have a probable spy,” said Popkin. “If the spy hears about it, he or she is going to leave. You have to keep it closely held.”

The Arrest of Ana Montes

During the 9/11 terrorist attacks, a jetliner crashed into the Pentagon, killing DIA employees and many others in the process. The DIA was responsible for developing U.S. attack plans against the Taliban and Afghanistan, and as a high-level analyst, Montes was granted access to those plans, including bombing targets in Afghanistan.

On Sept. 21, 2001, the FBI moved in, arresting Montes before she could reveal any more secrets. Before arresting Montes, the FBI and the DIA concocted an elaborate ruse to get her into an innocuous conference room at DIA headquarters.

The FBI was waiting. Montes quickly realized she was in deep trouble and requested a lawyer. 

Shortly after Montes’ arrest, Lucy was ushered into her boss’s office in Miami, and told her sister was a spy. Lucy was “angry and horrified,” said Popkin. But she was also relieved because it explained Ana’s strange and aloof behavior for many years.

Montes managed to secure the services of famed attorney Plato Cacheris, who got her off with 25 years, sparing her from a life sentence. Interestingly, Kendall Myers, a former U.S. State Department Official who taught part time at SAIS, and his wife, Gwendolyn, both spied for the Cubans at the same time Montes attended SAIS. Montes knew of Kendall Myers, but there is no evidence they colluded. 

Kendall and Gwendolyn Myers did far less damage than Montes, Popkin said. But Kendall was sentenced in 2010 to life behind bars and is still incarcerated. The late Gwendolyn Myers served 12 years before her release from prison.

Montes left prison on Jan. 6, 2023, after serving 21 years and three months. She is still on parole, meaning she is prohibited from talking to press about her case or meeting with foreign representatives for the next four years.

Montes was defiant when she left prison. She released a picture of herself smiling and issued a statement denouncing American foreign policy and the U.S. trade embargo on Cuba.

Montes now lives in Puerto Rico among a community of supporters. She is considered a martyr and a hero in some circles.

Not surprisingly, Lucy is still angry with her sister Ana, saying in an interview with Popkin that she hates what her sister did but is trying to forgive. 

As she told Popkin, “I’m her family. I’m her sister, and I can’t turn my back on her.” 

Editor’s Note: To order the book, Code Name Blue Wren: The True Story of America’s Most Dangerous Female Spy and the Sister She Betrayed, please go to the following website: https://bluewrenbook.com/