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.”

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 “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.” ” her US superiors with the quality of her work, no one was the wiser. //

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. //

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.” //

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.