Ana Montes is the most damaging spy in US history

Ana Montes is the most damaging spy in US history

When Ana Belén Montes was arrested as a Cuban spy 10 days after Sept. 11, 2001, the people who knew her best couldn’t believe it. One college friend said such treachery didn’t seem true to Ana’s character. During their time at the University of Virginia, the pal wrote in a newspaper op-ed, “The only secret she ever gave us was her mother’s luscious flan recipe.” But not only was Montes a Cuban spy, she was “one of the most damaging spies in US history,” author Jim Popkin writes in “Code Name Blue Wren: The True Story of America’s Most Famous Female Spy — and the Sister She Betrayed” (Hanover Square Press). (The book title refers to the FBI’s randomly generated code name for Ana.)

During her illustrious two-decade Washington career, Ana Montes shined at both her real job and her shadowy side hustle. 

As an analyst for the Defense Intelligence Agency (DIA), she won citations and cash awards for her impeccable work in charge of the agency’s Cuba desk — colleagues even called her the “Queen of Cuba.” 

The FBI arrested Ana ten days after the 9/11 terror attacks.
The FBI arrested Ana ten days after the 9/11 terror attacks.

But outside office hours, Montes shared her knowledge about American plans for Cuba — gleaned from classified US government documents — with the DGI, Castro’s intelligence agency. From 1984 to 2001, Ana would memorize secret documents on American policy before sharing the information over casual dinners with her Cuban handlers. Montes was literally given medals by the Cuban government for her undercover work (which they would take back for “safekeeping”), but as Montes regularly “dazzled” her US superiors with the quality of her work, no one was the wiser. 

The Montes family had Puerto Rican roots, but Ana was born an American citizen in 1957 in Nuremberg, Germany, where her Army father was stationed. She was raised in Topeka, Kan., after her father was transferred there. Ana’s father worked in mental health and understood the value of a loving home, but the senior Montes often beat his children with a belt. CIA investigators later stated that abuse might have made Ana “anti-authoritarian” and been a reason she turned against her country. 

Another motive was Ana’s disdain for US foreign policy. She’d hung a poster of Che Guevara in her girlhood bedroom because she truly believed in the principles of the Cuban revolution. Then, on a college year abroad in Spain, an Argentine boyfriend convinced Ana the US military regularly interfered in his homeland as well as in places like Nicaragua, El Salvador and Chile — where, he said, the United States supported a coup led by the murderous right-winger Augusto Pinochet. 

The FBI found secret codes and a crypto key in Ana's apartment after her arrest.
Pages of secret codes were found in Ana’s apartment after her 2001 arrest.

In Spain she was attracted to “social Communist parties,” the CIA would say. “Her early sympathies may have enhanced her later desire to assist a Communist government, such as Cuba.” 

In 1980, Ana was hired as a clerk/typist by the US Department of Justice in Washington, DC, but between her intelligence and work ethic she was promoted to the job of analyst at the DIA. An FBI background check failed to find her socialist sympathies or her “growing contempt” of U.S. foreign policy, so Ana was granted top-secret security clearance.   

“Ana had access to an almost unlimited smorgasbord of secrets prepared by the US intelligence community,” Popkin writes.  

It was an all-you-can-eat buffet the DGI would also soon enjoy.  

In the early 1980s, Montes was fascinated by the Sandinistas, “the Cuban-backed revolutionary Socialist political party” battling for control of the Nicaraguan government. Ana was aghast that President Ronald Reagan’s government supported the Contras, the “CIA-backed counterrevolutionaries trying to topple the Sandinistas.”   

Ana graduated from Loch Raven High School in Towson, Maryland, with a 3.9 GPA and headed to UVa for college.
Montes Family

When a friend told Ana she could “help the Sandinistas” by translating documents, Montes “unhesitatingly” agreed — and fully understood what the assignment would really entail. After a quick trip to New York to meet her friend’s Cuban contact, “in a popular Manhattan restaurant on Sunday, Dec. 16, 1984, Ana Montes became Fidel Castro’s greatest recruit.”  

The US analyst turned turncoat took a clandestine trip to Cuba, using fake passports while wearing different disguises and traveling through Spain and Czechoslovakia first. In Havana, the DGI taught their newest recruit the tradecraft the Soviets had previously taught them:  how to send secret communications, how to lose a tail, even how to beat a polygraph (by managing blood pressure through the controlled clenching of the sphincter muscle).   

A socialist true believer, Montes ignored the poverty she saw in Cuba and gladly helped the country defend itself against an “evil” Uncle Sam. The fact Ana was escorted around the island by a “gorgeous” Cuban agent who was likely a “hunk-for-hire” didn’t hurt her enthusiasm for the job.

DIA colleagues surprised Ana on her birthday. A rare moment of levity for the Queen of Cuba.
DIA Colleagues surprised Ana with cake on her birthday — and they, in turn, would be plenty surprised when she was later revealed to be a spy.

That trip to Havana was Montes’ only real cloak-and-dagger spying — the rest of her espionage career was as a glorified paper-pusher, delivering her memories of classified documents to a foreign power eager to get them. It was a lonely existence for Montes though, who couldn’t talk to anyone other than her Cuban handlers about her double life.   

Worse, her immediate family had unwittingly become Ana’s enemy: Her brother Tito and his wife became agents in the FBI’s Atlanta office, while her closest sibling, Lucy, worked for the FBI’s Miami field office — on a task force rooting Cuban spies out of South Florida. 

“Ana was surrounded,” Popkin writes. 

The isolation Montes felt from her deceit nearly broke her, leading her to visit a psychiatrist, take anti-depressants, and become obsessed with cleanliness, including spending hours every day in the shower — a calm, cool and collected James Bond of a spy Ana Montes was not.

Ana Montes in prison in 2002, as seen in the DIA internal training film The Two Faces of Ana Montes.
Ana Montes is seen in prison in 2002. She was ultimately released in January 2023, 21 years into a 25 year sentence.

But she kept up her double-dealing espionage for years, including revealing to the Cubans the true names of at least 4 covert U.S. agents operating in Havana.  

“We were waiting for him here with open arms,” the DGI ominously told Ana about one. 

And just weeks after her DIA-sponsored trip to a Salvadoran military camp in early 1987 (where US soldiers were training Contra rebels), the outpost was attacked, killing one American Green Beret and the 43 Nicaraguans who’d been fighting beside him. Military experts long believed that attack was aided by an “inside source,” which of course had been Montes. 

After her arrest, Montes showed no remorse for the lives she likely ended, saying “Espionage always hurts someone.” 

The first suspicions raised against Ana occurred in early 1996, when the Cuban air force shot down two humanitarian planes that had entered its airspace — “We blew his balls off!” the Cuban pilot could be heard crowing over radio transmissions. Three Americans were killed, and President Bill Clinton was “publicly fuming.” But the next day at the office, which should have been the apex of the “Queen of Cuba’s” intelligence career, Ana went missing after taking a personal phone call and becoming “visibly agitated.” 

‘Espionage always hurts someone.’

Ana Montes, unrepentant after her 2001 arrest

Seeing that, yellow flags went up for Reg Brown, a DIA counterintelligence analyst for Latin America. He asked a colleague to investigate Montes, and while that agent thought Ana might be “hiding something” he also cleared her — Ana’s stellar work reputation and the fact she’d recently passed a regularly-scheduled DIA polygraph (through sphincter-muscle-clenching?) got her off the hook. 

Ironically it was partly the work of Montes’ sister Lucy that ultimately did Ana in. Lucy’s involvement in the FBI, NSA, and Navy’s Royal Flush Task Force broke up a Cuban spy ring in South Florida, and part of the information uncovered revealed a mole working in an unknown Washington, DC intelligence agency. The double agent was known to have had a student loan paid off by the Cubans, owned a particular type of Toshiba computer, and traveled to Guantanamo Bay in the summer of 1996.   

That ended up being strikes one, two and three against Montes. After the earlier accusation against her, those new disclosures were enough for DIA investigators to point the finger at their very own “Queen of Cuba.” 

Code name blue wren
After her arrest, Montes showed no remorse for the lives she likely ended, saying “Espionage always hurts someone.” 

The FBI broke into Ana’s Washington apartment under a FISA court order — “we snuck in like ninjas” the agent in charge boasted — to plant cameras and recording devices and soon found the very model of Toshiba computer used by the mole. There was a short-wave radio that could be used to communicate with Cuba and, most damningly, unencrypted messages on a typewriter cartridge that unequivocally proved Ana Montes betrayed her country. 

After she was arrested, Montes denied nothing. She pled guilty in open court, even confessing she hadn’t committed treason for the money. Other than the $2,000 student loan the Cubans had paid off at the beginning of Ana’s second career, she’d continued undermining US national security for the next 15 years as a matter of principle. 

She did what she did, Ana Montes told the judge at her sentencing hearing, because she “followed my conscience rather than the law.” 

Many hard-liners wanted Montes put to death for her treason, but she was given just a 25-prison term. After serving 21 years of that sentence, Montes was released little more than a week ago, on Jan. 6, for her “good behavior” behind bars. The “Blue Wren” is now flying free. 

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