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Spy vs. spy: Dept. of Defense analyst’s treasonous trail detailed in new book

Ana Montes (FBI/Released)

Every spy keeps secrets, but Ana Montes hid a shocking one.

She was a traitor.

For nearly 20 years, the U.S. intelligence analyst compiled information on Cuba, El Salvador, and Nicaragua. She combed through data, interviewed experts, and drew up lists of undercover agents.

Then she shared everything with her real bosses – in Havana.

“Montes leaked information that likely led to the death of an American Green Beret killed in action in El Salvador,” Jim Popkin writes in “Code Name Blue Wren: The True Story of America’s Most Dangerous Female Spy – and the Sister She Betrayed.”

“She freely shared the identities of hundreds of Americans working on Cuban intelligence matters around the globe,” Popkin writes. “She revealed the existence of a stealth satellite so costly and highly classified that U.S. government officials still won’t utter its name.”

Making the betrayal especially bitter? Her family’s devotion to the military and law enforcement. As Montes was passing secrets to Fidel Castro’s agents in Washington, her younger sister, Lucy, was an FBI translator and even working in a unit catching Cuban spies in Miami.

Ana Montes’ treason surprised everyone who knew her. Born into a conservative family, her Puerto Rican father had come to the mainland to study medicine and became a doctor in the U.S. Army and later a private psychiatrist. He and his family – wife, two girls, and two boys – settled in suburban Maryland.

He insisted on strict discipline, and enforced it with beatings.

“Nobody ever knew what was going to set him off,” his daughter, Lucy, said. “He had a bad temper and a bad marriage with my mother. He was a violent man.”

As she grew up, Montes increasingly defied him – including politically. Still, her leanings seemed more progressive than radical. After college, she joined the U.S. Justice Department’s Office of Privacy and Information Appeals. It was an entry-level government job, handling the growing deluge of Freedom Of Information requests.

Montes passed the routine background investigation and was awarded a top security clearance. “Loyal, very moral, extremely independent with a flawless reputation,” the report concluded. She rose quickly in government while pursuing a graduate degree at the Johns Hopkins School of Advanced International Studies.

At the time, the campus provided a safe space for Castro sympathizers. One leftist professor, Walter Kendall Myers, was already spying for Cuba. He was convicted in 2009 and received a life sentence. Grad student Marta Velazquez also on Castro’s payroll, was charged with recruiting other eager young Americans.

Velazquez zeroed in on Montes, who had made no secret of her government job or her disgust with American foreign policy.

“At a restaurant in Washington, (Velazquez) made a soft pitch,” Popkin writes. “‘Ana, I have friends who can help you assist the desperate Nicaraguan people…. They need someone to translate Spanish-language news articles.’”

Velazquez suggested a trip to New York, so Montes could meet her friends, who were Cuban intelligence officers.

On Dec. 16, 1984, Montes agreed to betray her country.

Of course, she told no one. But when her sister called with the news that she had just joined the Federal Bureau of Investigation, Montes was horrified.

“She got all upset,” Lucy recalled later. “I was really surprised that she would be so against it. I couldn’t understand it.”

Once government agents started looking closely, there were many things not easily understandable about Ana Montes. By now, she had a job at the Department of Defense’s Defense Intelligence Agency — and increased access to national secrets. Soon, her betrayals included a human cost.

She revealed the names of undercover agents working against the Cuban government. Alerted to one spy’s arrival, her Havana handlers coldly messaged back, “We are waiting here for him with open arms.” She also visited a military base in El Salvador, supposedly as part of her official job. A month later, rebels attacked that camp and killed 44 soldiers, including a Green Beret.

“I’m certain that she turned over information about that one particular camp to the Cubans,” one U.S. investigator declared later. “I mean, there is no doubt.” But there was no hard evidence.

There rarely was, thanks to Montes’ almost-paranoid security. She received coded instructions via short-wave radio; she replied via pay phones. Unlike other spies, Montes refused to risk removing files from her office, instead committing them to memory. Later, she would meet her Cuban bosses at local Chinese restaurants and repeat the stolen secrets word for word.

Montes remained remarkably successful. She continued to earn raises and promotions at work and even received an award from the head of the CIA. Ironically, Montes also received an award from the Cubans – a medal so secret they showed it to her, then took it back.

But her double life was taking a toll. Because there was no one she could truly trust, she kept everyone at bay. She had no close friends and few romantic possibilities. At one point, her Cuban bosses sympathetically arranged a blind date with another spy. It didn’t work out. Montes began to see a psychiatrist. She took endless showers as if trying to scrub herself clean.

Unsurprisingly, Montes began to arouse suspicions. She had started pushing her way into meetings she had no business in, accessing reams of classified information for which she could claim no legitimate use. American operatives had already received a tip that one of their colleagues had been working with the Cubans. A few details – dates of trips, certain electronics purchased – seemed to point to Montes.

Slowly, carefully, they began to spy on the spy.

FBI agents tailed her walks around Washington, sifted through her apartment building’s dumpsters, tapped her phone, and hacked her computer. They broke into her apartment when she was away and discovered a short-wave radio. Before they left, they installed hidden cameras and microphones.

The evidence they eventually assembled — including communications between Montes and her Cuban bosses — was undeniable.

On Sept. 21, 2001, Montes received a call at work saying there was a problem with a timecard. Could she come to the Inspector General’s office and clear it up? When Montes showed up, a receptionist ushered her into a conference room. Two FBI agents were waiting. Montes barely flinched, even as they snapped on the handcuffs.

And she has not wavered since.

At her trial, Montes refused to cry or even apologize. “I believe our country’s policy toward Cuba is cruel and unfair,” she stated. “I felt morally obligated to help the island defend itself.” Unlike other spies, it seemed she had not done this for money. Over almost 20 years, Montes only accepted a few thousand dollars, primarily for expenses.

Instead, her reason was deeper — she spied out of conviction and love. Montes was faithful only to Fidel.

The judge sentenced her to 25 years, and she was sent to a supermax prison in Texas, where her fellow inmates included Squeaky Fromme and Al Qaeda terrorists. Her only friend was a death-row murderer who had slit open a pregnant woman and stolen her baby.

Montes silently does her time. On Jan. 8, 2023, having served 21 years, three months, and 19 days, she is scheduled to walk out a free woman.

And if Montes regrets anything – that’s just another one of her secrets.


© 2022 New York Daily News

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