Ana Montes is probably the most damaging spy in US historical past


When Ana Belén Montes was arrested as a Cuban spy 10 days after Sept. 11, 2001, the people who knew her most interesting couldn’t think about it. One school pal talked about such treachery didn’t seem true to Ana’s character. During their time on 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 solely was Montes a Cuban spy, she was “one of the most damaging spies in US history,” creator 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 information title refers again to the FBI’s randomly generated code establish for Ana.)

During her illustrious two-decade Washington occupation, Ana Montes shined at every her precise job and her shadowy aspect hustle. 

As an analyst for the Defense Intelligence Agency (DIA), she acquired citations and cash awards for her impeccable work in command of the firm’s Cuba desk — colleagues even often 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 assaults.

But exterior office hours, Montes shared her details about American plans for Cuba — gleaned from categorised US authorities paperwork — with the DGI, Castro’s intelligence firm. From 1984 to 2001, Ana would memorize secret paperwork on American protection sooner than sharing the information over casual dinners collectively along with her Cuban handlers. Montes was truly given medals by the Cuban authorities for her undercover work (which they’d take once more for “safekeeping”), nonetheless as Montes recurrently “dazzled” her US superiors with the commonplace of her work, no person was the wiser. 

The Montes family had Puerto Rican roots, nonetheless Ana was born an American citizen in 1957 in Nuremberg, Germany, the place her Army father was stationed. She was raised in Topeka, Kan., after her father was transferred there. Ana’s father labored in psychological effectively being and understood the value of a loving dwelling, nonetheless the senior Montes normally beat his children with a belt. CIA investigators later mentioned that abuse would possibly want made Ana “anti-authoritarian” and been a goal she turned in the direction of her nation. 

Another motive was Ana’s disdain for US worldwide protection. She’d hung a poster of Che Guevara in her girlhood mattress room because of she actually believed inside the guidelines of the Cuban revolution. Then, on a college yr abroad in Spain, an Argentine boyfriend glad Ana the US navy recurrently interfered in his homeland in addition to in areas like Nicaragua, El Salvador and Chile — the place, he talked about, 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 had been current in Ana’s home after her 2001 arrest.

In Spain she was in “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 employed as a clerk/typist by the US Department of Justice in Washington, DC, nonetheless between her intelligence and work ethic she was promoted to the job of analyst on the DIA. An FBI background confirm failed to go looking out her socialist sympathies or her “growing contempt” of U.S. worldwide protection, 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 moreover shortly take pride in.  

In the early Eighties, Montes was fascinated by the Sandinistas, “the Cuban-backed revolutionary Socialist political party” battling for administration of the Nicaraguan authorities. Ana was aghast that President Ronald Reagan’s authorities 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 varsity.
Montes Family

When a pal instructed Ana she would possibly “help the Sandinistas” by translating paperwork, Montes “unhesitatingly” agreed — and completely understood what the venture would truly entail. After a quick journey to New York to fulfill her pal’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 journey to Cuba, using fake passports whereas sporting fully completely different disguises and touring via Spain and Czechoslovakia first. In Havana, the DGI taught their newest recruit the tradecraft the Soviets had beforehand taught them:  how one can ship secret communications, how one can lose a tail, even how one can beat a polygraph (by managing blood stress via the managed clenching of the sphincter muscle).   

A socialist true believer, Montes ignored the poverty she seen in Cuba and gladly helped the nation defend itself in the direction of an “evil” Uncle Sam. The fact Ana was escorted throughout the island by a “gorgeous” Cuban agent who was potential a “hunk-for-hire” didn’t injury her enthusiasm for the job.

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

That journey to Havana was Montes’ solely precise cloak-and-dagger spying — the the rest of her espionage occupation was as a glorified paper-pusher, delivering her recollections of categorised paperwork to a worldwide vitality eager to get them. It was a lonely existence for Montes though, who couldn’t converse to anyone other than her Cuban handlers about her double life.   

Worse, her speedy family had unwittingly grow to be Ana’s enemy: Her brother Tito and his partner grew to grow to be brokers inside the FBI’s Atlanta office, whereas her closest sibling, Lucy, labored for the FBI’s Miami space office — on a job stress rooting Cuban spies out of South Florida. 

“Ana was surrounded,” Popkin writes. 

The isolation Montes felt from her deceit virtually broke her, principal her to go to a psychiatrist, take anti-depressants, and grow to be obsessive about cleanliness, along with spending hours daily inside the bathe — a relaxed, cool and picked up 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 jail in 2002. She was lastly launched in January 2023, 21 years proper right into a 25 yr sentence.

But she saved up her double-dealing espionage for years, along with revealing to the Cubans the true names of at the least 4 covert U.S. brokers working in Havana.  

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

And merely weeks after her DIA-sponsored journey to a Salvadoran navy camp in early 1987 (the place US troopers had been teaching Contra rebels), the outpost was attacked, killing one American Green Beret and the 43 Nicaraguans who’d been combating beside him. Military specialists prolonged believed that assault was aided by an “inside source,” which in truth had been Montes. 

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

The first suspicions raised in the direction of Ana occurred in early 1996, when the Cuban air stress shot down two humanitarian planes that had entered its airspace — “We blew his balls off!” the Cuban pilot might very effectively be heard crowing over radio transmissions. Three Americans had been killed, and President Bill Clinton was “publicly fuming.” But the subsequent day on the office, which must have been the apex of the “Queen of Cuba’s” intelligence occupation, Ana went missing after taking a non-public cellphone identify 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 requested a colleague to analysis Montes, and whereas that agent thought Ana is more likely to be “hiding something” he moreover cleared her — Ana’s stellar work standing and the precise truth she’d currently handed a regularly-scheduled DIA polygraph (via sphincter-muscle-clenching?) purchased her off the hook. 

Ironically it was partly the work of Montes’ sister Lucy that lastly did Ana in. Lucy’s involvement inside 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 firm. The double agent was recognized to have had a scholar mortgage paid off by the Cubans, owned a selected form of Toshiba laptop computer, and traveled to Guantanamo Bay in the summertime of 1996.   

That ended up being strikes one, two and three in the direction of Montes. After the sooner accusation in the direction of her, these new disclosures had been enough for DIA investigators to degree the finger at their very private “Queen of Cuba.” 

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

The FBI broke into Ana’s Washington home beneath a FISA courtroom docket order — “we snuck in like ninjas” the agent in value boasted — to plant cameras and recording models and shortly found the very model of Toshiba laptop computer utilized by the mole. There was a short-wave radio that will very effectively be used to talk with Cuba and, most damningly, unencrypted messages on a typewriter cartridge that unequivocally proved Ana Montes betrayed her nation. 

After she was arrested, Montes denied nothing. She pled accountable in open courtroom docket, even confessing she hadn’t devoted treason for the money. Other than the $2,000 scholar mortgage the Cubans had paid off at the begin of Ana’s second occupation, she’d continued undermining US nationwide security for the subsequent 15 years as a matter of principle. 

She did what she did, Ana Montes instructed the select at her sentencing listening to, because of she “followed my conscience rather than the law.” 

Many hard-liners wished Montes put to demise for her treason, nonetheless she was given solely a 25-prison time interval. After serving 21 years of that sentence, Montes was launched little better than per week in the past, on Jan. 6, for her “good behavior” behind bars. The “Blue Wren” is now flying free. 

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