Friday, April 19, 2013

Ana Montes did much harm spying for Cuba. Chances are, you haven't heard of her.

Ana Montes did much harm spying for Cuba. Chances are, you haven't heard
of her.
Posted by Jim Popkin on April 18, 2013 at 3:03 pm
By Jim Popkin

Ana Montes has been locked up for a decade with some of the most
frightening women in America. Once a highly decorated U.S. intelligence
analyst with a two-bedroom co-op in Cleveland Park, Montes today lives
in a two-bunk cell in the highest-security women's prison in the nation.
Her neighbors have included a former homemaker who strangled a pregnant
woman to get her baby, a longtime nurse who killed four patients with
massive injections of adrenaline, and Lynette "Squeaky" Fromme, the
Charles Manson groupie who tried to assassinate President Ford.

But hard time in the Lizzie Borden ward of a Texas prison hasn't
softened the former Defense Department wunderkind. Years after she was
caught spying for Cuba, Montes remains defiant. "Prison is one of the
last places I would have ever chosen to be in, but some things in life
are worth going to prison for," Montes writes in a 14-page handwritten
letter to a relative. "Or worth doing and then killing yourself before
you have to spend too much time in prison."

Like Aldrich Ames and Robert Hanssen before her, Ana Montes blindsided
the intelligence community with brazen acts of treason. By day, she was
a buttoned-down GS-14 in a Defense Intelligence Agency cubicle. By
night, she was on the clock for Fidel Castro, listening to coded
messages over shortwave radio, passing encrypted files to handlers in
crowded restaurants and slipping undetected into Cuba wearing a wig and
clutching a phony passport.

Montes spied for 17 years, patiently, methodically. She passed along so
many secrets about her colleagues — and the advanced eavesdropping
platforms that American spooks had covertly installed in Cuba — that
intelligence experts consider her among the most harmful spies in recent
memory. But Montes, now 56, did not deceive just her nation and her
colleagues. She also betrayed her brother Tito, an FBI special agent;
her former boyfriend Roger Corneretto, a Cuban-intelligence officer for
the Pentagon; and her sister, Lucy, a 28-year veteran of the FBI who has
won awards for helping to unmask Cuban spies.


In the days after the Sept. 11, 2001, terrorist attacks, the FBI's Miami
field office was on high alert. Most of the hijackers had spent time in
South Florida, and FBI personnel there were desperate to learn whether
any more had stayed behind. So when a supervisor asked Lucy Montes to
come to his office, she didn't blink. Lucy was a veteran FBI language
analyst who translated wiretaps and other sensitive communications.

But this impromptu meeting had nothing to do with Sept. 11. An FBI squad
leader sat Lucy down. Your sister, Ana, has been arrested for espionage,
he informed her, and she could face the death penalty. Your sister, Ana,
is a Cuban spy.

Lucy didn't scream, didn't storm out in disbelief. Instead, she found
the news strangely reassuring. "I believed it right away," she recalled
in a recent interview. "It explained a lot of things."

Major news organizations reported on the arrest, of course, but it was
overshadowed by nonstop coverage of the terrorist attacks. Today, Ana
Montes remains the most important spy you've never heard of.


Ana Montes with her family at the FBI training facility at Quantico in
1989. From left, father Alberto, Ana, sister Lucy, then-sister-in-law
Joan and brother Tito. (Photograph courtesy family)

Born on a U.S. Army base in 1957, Ana Montes is the eldest child of
Emilia and Alberto Montes. Puerto Rico-born Alberto was a respected Army
doctor, and the family moved frequently, from Germany to Kansas to Iowa.
They settled in Towson, outside Baltimore, where Alberto developed a
successful private psychiatric practice and Emilia became a leader in
the local Puerto Rican community.

Ana thrived in Maryland. Slender, bookish and witty, she graduated with
a 3.9 GPA from Loch Raven High School, where she noted in her senior
yearbook that her favorite things included "summer, beaches … chocolate
chip cookies, having a good time with fun people." But the bubblegum
sentimentality masked a growing emotional distance, grandiose feelings
of superiority and a troubling family secret.

To outsiders, Alberto was a caring and well-educated father of four. But
behind closed doors, he was short-tempered and bullied his children.
Alberto "happened to believe that he had the right to beat his kids,"
Ana would later tell CIA psychologists. "He was the king of the castle
and demanded complete and total obedience." The beatings started at 5,
Lucy said. "My father had a violent temper," she said. "We got it with
the belt. When he got angry. Sure."

Ana's mother feared taking on her mercurial husband, but as the verbal
and physical abuse persisted, she divorced him and gained custody of
their children.

Ana was 15 when her parents separated, but the damage had been done.
"Montes's childhood made her intolerant of power differentials, led her
to identify with the less powerful, and solidified her desire to
retaliate against authoritarian figures," the CIA wrote in a
psychological profile of Montes labeled "Secret." Her "arrested
psychological development" and the abuse she suffered at the hands of a
temperamental man she associated with the U.S. military "increased her
vulnerability to recruitment by a foreign intelligence service," adds
the 10-page report. Lucy recalls that even as a teenager Ana was distant
and judgmental. "We were only a year apart, but I have to tell you that
I never really felt close to her," Lucy said. "She wasn't one that
wanted to share things or talk about things."


Ana Montes was a junior at the University of Virginia when she met a
handsome student during a study-abroad program in Spain. He was from
Argentina and a leftist, friends recall, and helped open Montes's eyes
to the U.S. government's support of authoritarian regimes. Spain had
become a hotbed of political radicalism, and the frequent anti-American
protests offered a welcome diversion from schoolwork. "After every
protest, Ana used to explain to me the 'atrocities' that the U.S.A.
government used to do to other countries," recalls Ana Colón, a fellow
college student who befriended Montes in Spain in 1977 and now lives
near Gaithersburg. "She was already so torn. She did not want to be
American but was."

After college, Montes moved briefly to Puerto Rico but could not find
suitable work. When a friend told her about an opening as a clerk typist
at the Department of Justice in Washington, she put her political
considerations aside. A job was a job.

Montes excelled at the DOJ's Office of Privacy and Information Appeals.
Less than a year later, after an FBI background check, the Department of
Justice granted Montes top-secret security clearance. She could now
review some of the DOJ's most sensitive files.

While holding down her day job, Montes began pursuing a master's degree
at the School of Advanced International Studies at Johns Hopkins
University. Her political views hardened. Montes developed a hatred for
the Reagan administration's policies in Latin America and especially for
U.S. support of the contras, the rebels fighting the communist
Sandinista government in Nicaragua.

Montes was now a budding Washington bureaucrat and a full-time student
at one of the country's premier universities. But she was about to take
on another demanding assignment: spy in training. In 1984, the
Cuban-intelligence service recruited her as a full-blown agent.

Sources close to the case think that a friend at SAIS served as a
facilitator for the Cubans, helping to identify potential spies. Cuba
considers recruiting at American universities a "top priority,"
according to former Cuban intelligence agent Jose Cohen, who wrote in an
academic paper that the Cuban intelligence service identifies
politically driven students at leading U.S. colleges who will "occupy
positions of importance in the private sector and in the government."

Montes must have seemed a godsend. She was a leftist with a soft spot
for bullied nations. She was bilingual and had dazzled her DOJ
supervisors with her ambition and smarts. But most important, she had
top-secret security clearance and was on the inside. "I hadn't thought
about actually doing anything until I was propositioned," Montes would
later admit to investigators. The Cubans, she revealed, "tried to appeal
to my conviction that what I was doing was right."

CIA analysts interpret the recruitment a bit more darkly. Montes was
manipulated into believing that Cuba desperately needed her help,
"empowering her and stroking her narcissism," the CIA wrote. The Cubans
started slowly, asking for translations and bits of harmless intel that
might assist the Sandinistas, her pet cause. "Her handlers, with her
unwitting assistance, assessed her vulnerabilities and exploited her
psychological needs, ideology, and personality pathology to recruit her
and keep her motivated to work for Havana," the CIA concluded.

Montes secretly visited Cuba in 1985 and then, as instructed, began
applying for government positions that would grant her greater access to
classified information. She accepted a job at the Defense Intelligence
Agency, the Pentagon's major producer of foreign military intelligence.

In an early mistake, Montes had confided to her old friend from Spain,
Ana Colón, that she had visited Cuba and had had a fling with the cute
guy who toured her around the island. Montes also revealed that she was
about to take a DIA job. "I was dumbfounded," Colón recalled. "I
couldn't understand why somebody with her leftist beliefs would be
willing to work for the U.S.A. government and for the military." Montes
said she wanted to be part of the political action and was "an American
girl, after all." But days after the confession, Montes cut her
girlfriend off. Colón called and wrote letter after letter for 2 1/2
years, to no avail. Montes wouldn't engage. Colón never heard from
Montes again.

Back in Miami, Lucy Montes also was puzzled by her sister's decision to
work for the Defense Department. But she loved her sister and was so
eager to make a connection that she didn't press the point. Ana had
become more introverted and rigid in her views since joining DIA. "She
would talk to me less and less about things that were going on with
her," Lucy said. Ironically, Ana now had much in common with her
siblings. Although Juan Carlos, the baby of the family, had become a
deli owner in Miami, Lucy and her other brother, Alberto "Tito" Montes,
had chosen careers helping to protect the United States. Tito had become
an FBI special agent in Atlanta, where he still works, and his wife was
an FBI agent. Lucy had become an FBI Spanish-language analyst in Miami,
a job she still holds, frequently working on cases involving Cubans. Her
husband at the time worked for the FBI, too.

Of her family members, only Lucy would be interviewed. She agreed to
talk for the first time — more than a decade after her sister's arrest —
to make her views on Ana clear. "I don't feel the way that a lot of her
friends seem to feel, like there's a good excuse for what she did, or I
can understand why she did it, or, you know, what this country did is
wrong. There's nothing to be admired," Lucy said.


For the next 16 years, Ana Montes excelled — in both Washington and
Havana. Hired by the DIA as an entry-level research specialist, she was
promoted again and again. Montes quickly became DIA's principal analyst
for El Salvador and Nicaragua, and later was named the DIA's top
political and military analyst for Cuba. In the intelligence community
and at DIA headquarters, Montes became known as "the Queen of Cuba." Not
only was she one of the U.S. government's shrewdest interpreters of
Cuban military affairs — hardly surprising, given her inside knowledge —
but she also proved adept at shaping (and often softening) U.S. policy
toward the island nation.

Over her meteoric career, Montes received cash bonuses and 10 special
recognitions for her work, including a certificate of distinction that
then-CIA Director George Tenet presented to her in 1997. The Cubans also
awarded their star student with a medal, a private token of appreciation
that Montes could never take home.

She became a model of efficiency, a warrior monk embedded deep within
the bureaucracy. From cubicle C6-146A at DIA headquarters at Joint Base
Anacostia-Bolling in Washington, she gained access to hundreds of
thousands of classified documents, typically taking lunch at her desk
absorbed in quiet memorization of page after page of the latest
briefings. Colleagues recall that she could be playful and charming,
especially with bosses or when trying to talk her way into a classified
briefing. But she also could be arrogant and declined most social

Montes would clock out at DIA, then start her second job at her Macomb
Street apartment in Cleveland Park. She never risked taking a document
home. Instead, she fastidiously memorized by day and typed in the
evenings, spewing whole documents into a Toshiba laptop. Night after
night, she poured years' worth of highly classified secrets onto cheap
floppy disks bought at Radio Shack.

Her tradecraft was classic. In Havana, agents with the Cuban
intelligence service taught Montes how to slip packages to agents
innocuously, how to communicate safely in code and how to disappear if
needed. They even taught Montes how to fake her way through a polygraph
test. She later told investigators it involves the strategic tensing of
the sphincter muscles. It's unknown if the ploy worked, but Montes did
pass a DIA-administered polygraph in 1994, after a decade of spying.

Montes got most of her orders the same way spies have since the Cold
War: through numeric messages transmitted anonymously over shortwave
radio. She would tune a Sony radio to AM frequency 7887 kHz, then wait
for the "numbers station" broadcast to begin. A female voice would cut
through the otherworldly static, declaring, "Atención! Atención!" then
spew out 150 numbers into the night. "Tres-cero-uno-cero-siete,
dos-cuatro-seis-dos-cuatro," the voice would drone. Montes would key the
digits into her computer, and a Cuban-installed decryption program would
convert the numbers into Spanish-language text.

Montes also took the unusual risk of meeting the Cubans face-to-face.
Every few weeks, she would dine with her handlers in D.C. area Chinese
restaurants, where Montes would slide a fresh batch of encrypted
diskettes past tiny dishes of Chinese delicacies. The clandestine
handoffs also took place during Montes's vacations, on sunny Caribbean

Montes even traveled to Cuba four times for sessions with Cuba's top
intelligence officers. Twice, she used a phony Cuban passport and
disguised herself in a wig, hop-scotching first to Europe to cover her
tracks. Two other times she got Pentagon approval to visit Cuba on U.S.
fact-finding missions. She would meet at the U.S. Interests Section in
Havana during the day but slip away to brief her Cuban superiors.

Back in the States, when Montes needed to convey an urgent message, she
reached for a pager. Montes would seek out pay phones at the National
Zoo, the Friendship Heights Metro or by the old Hecht's in Chevy Chase
to call pager numbers controlled by the Cubans. One beeper code would
mean "I'm in extreme danger"; another, "We have to meet." Schooled in
spycraft by the KGB, the Cubans relied on the storied tools of the
trade. Montes's pager codes and shortwave-radio notes, for example, were
written on specially treated paper. "The frequencies and the cheat sheet
for the numbers, that was all on water-soluble paper," explained the
FBI's Pete Lapp, one of two top agents on the case. "You throw it in the
toilet, and it evaporates."


Spying was lonely. Montes could confide only in her handlers. Family
gatherings and holidays with her two FBI siblings and their FBI-employed
spouses became tense affairs. At the beginning, the Cubans provided
enough of a social life. "They were emotionally supportive. They
understood my loneliness," Montes told investigators. But as she turned
40, Montes became despondent. "I was finally ready to share my life with
someone but was leading a double life, so I did not feel I could live
happily," she revealed. The Cubans set her up with a lover, but after a
couple of days of fun, she realized she would not find happiness with a
"mail order" groom.
Ana Montes1631364842332_image_1024w

When FBI agents covertly searched Montes's Cleveland Park apartment,
they found her laptop and the shortwave radio she used to communicate
with Cuba. (Photograph by Matthew Girard)

Ana's alienation only grew when, by strange coincidence, Lucy began
working on the biggest case of her career: a massive crackdown on Cuban
spies operating in the United States. It was 1998, and the Miami field
office had uncovered a Cuban spy ring based in Florida, the so-called
Wasp Network. More than a dozen members strong, the Wasp Network was
infiltrating Cuban exile organizations and making inroads into U.S.
military sites in Florida upon its capture. For Lucy, the Wasp case
marked the crowning achievement of her career. The FBI had called on her
to translate hours of wiretapped conversations of Cuban spies who were
trying to penetrate the U.S. Southern Command base in Doral. Lucy earned
praise from the FBI brass and an award from a local Latin chamber of
commerce. But she never shared the news with Ana. Although Ana was one
of the preeminent Cuba experts in the world and should have been
ecstatic that her sister had helped expose a Cuban spy ring, Lucy was
convinced Ana would just change the subject. "I knew she would have no
interest in hearing about it or talking about it," Lucy said.

But Lucy's triumph became Ana's despair. Ana's handlers suddenly went
dark. They refused to contact her for months as they assessed the
fallout from the investigation. "Something that gave me fulfillment
disappeared," she later told investigators. Ana bottomed out. She
experienced crying spells, panic attacks and insomnia. She sought
psychiatric treatment and started taking antidepressants. CIA-led
psychologists would later conclude that the isolation, lies and fear of
capture had triggered borderline obsessive-compulsive traits. Montes
began showering for long stretches with different soaps and wearing
gloves when she drove her car. She strictly controlled her diet, at
times eating only unseasoned boiled potatoes. At a birthday party at
Lucy's home in 1998, Ana sat stone-faced and barely spoke. "Some of my
friends thought she was very rude, that there was something seriously
odd with her. And there was. She was cut off from her handler," Lucy said.

Inside the DIA, the star analyst remained above suspicion. Montes had
succeeded beyond the Cubans' wildest dreams. She was now briefing the
Joint Chiefs of Staff, the National Security Council and even the
president of Nicaragua about Cuban military capabilities. She helped
draft a controversial Pentagon report stating that Cuba had a "limited
capacity" to harm the United States and could pose a danger to U.S.
citizens only "under some circumstances." And she was about to earn yet
another promotion, this time a prestigious fellowship with the National
Intelligence Council. An advisory body to the director of central
intelligence, the NIC was then at CIA headquarters in Langley. Montes
was about to gain access to even more treasured information. Her spy
career would have reached unfathomable heights, had it not been for a
back-bench DIA employee named Scott Carmichael.


Round-faced and often stuffed uncomfortably in size 44 suits from
Macy's, Carmichael defies the stereotype of the sophisticated,
Georgetown-trained mole hunter. He laughingly describes himself as "a
Kmart security guard," but for the past quarter-century the former cop
from Wisconsin's dairy belt has hunted spies for the DIA.

In September 2000, Carmichael got a hot lead. Veteran DIA
counterintelligence analyst Chris Simmons had been approached by a
female intelligence officer. She had risked her career to inform Simmons
that the FBI had spent two years fruitlessly trying to identify a U.S.
government employee who appeared to be spying for the Cubans. It was an
"UNSUB" case, meaning a search for an unidentified subject. The FBI knew
that the UNSUB had high-level access to U.S. intelligence on Cuba, had
purchased a Toshiba laptop to communicate with Havana and a few other
tidbits. But with so few details, the FBI investigation had stalled.

Carmichael got to work. He and his colleague Karl "Gator" James began
inputting some of the FBI's closely held clues into their employee
databases. DIA workers surrender many of their privacy rights when
applying for security clearances, and Carmichael had access to reams of
personal financial records, medical histories and detailed travel
itineraries. The computer search produced more than a hundred possible
employee matches. After scanning through about 20 subjects, the name
"Ana Belen Montes" popped onto Carmichael's screen.

Carmichael knew her. Four years earlier, one of Montes's fellow DIA
analysts had squealed on her, troubled by her occasionally aggressive
efforts to access sensitive information. Carmichael had even interviewed
Montes and thought she had been lying. "I was left with this nagging
doubt," he recalls. But Montes had been able to explain away all her
actions, and Carmichael had closed the case. Now the computer screen was
blinking Montes's name, and he was convinced she must be a spy. "I knew,
I really knew it was her," he said.

But the FBI was unimpressed. Lead agent Steve McCoy riddled holes in
Carmichael's thesis, pointing out that many other federal workers and
contractors matched the same circumstantial shreds of evidence that had
supposedly tied Montes to the case. And some of Carmichael's evidence
made no sense.

Carmichael conceded there were holes in his theory and reminded himself
that Montes was a stellar employee. He also knew that few women have
been prosecuted for espionage in America since the Cold War. Still,
Carmichael was certain he was on the right track. As he walked out of
the FBI that first day, he swore a pledge. "I can remember looking off,
in the direction of the DIA and being so freakin' pissed off,"
Carmichael fumed years later. "I told Gator we're going to war. I said,
'We're getting rid of that … woman, and these guys don't know it yet,
but they're opening a case on her.' "

Carmichael built a dossier on Montes and began badgering McCoy with
facts, dates and coincidences. He made excuses to stop by McCoy's office
to talk about Montes and fill in holes. And when he was ignored, he went
over McCoy's head.

After nine weeks, Carmichael's relentless campaign paid off. McCoy was
sold and persuaded headquarters to open a full investigation. "The
bureau got really lucky when the DIA came to us with Montes as a
suspect," said Pete Lapp, McCoy's partner on the case. Despite their
differences, McCoy says Carmichael deserves a tremendous amount of
credit for his tenacity: "He broke the case. He gave us our subject,"
and "from that point on, the FBI made the case."

Once the FBI was fully engaged, it assigned more than 50 people to work
the investigation and won permission from a skeptical Foreign
Intelligence Surveillance Court judge to conduct surreptitious searches
of Montes's apartment, car and office. FBI operatives tailed Montes and
filmed her making suspicious calls on pay phones. Lapp used a national
security letter, a form of administrative subpoena, to gain unfettered
access to Montes's credit records. Montes, he learned, had applied for a
line of credit in 1996 at a CompUSA store in Alexandria. Her purchase?
The same model of Toshiba laptop that the FBI had learned about from its
original source when it began its UNSUB investigation. "It was awesome,
it was awesome," Lapp recalls. "This was regular old detective work."

Still, no one had witnessed Montes meeting a Cuban, typing coded
messages at work or stuffing anything classified into her pocketbook.
For Lapp, then, there was a lot riding on the first sneak-and-peek of
Montes's apartment. He needed concrete proof that Montes was a spy. Yet
he couldn't risk tipping her off with a messy search. "There's no bigger
stress that I've had professionally than being in someone's apartment,
legally, with them not knowing it and having a chance to get caught,"
said Lapp, a former police officer. "You're being a cat burglar,
legally, but you can get caught, and the entire case is blown."

Adding urgency was Montes's pending promotion to the CIA advisory
council. Carmichael needed to quietly stall the assignment. With help
from then-DIA director Vice Adm. Thomas Wilson, they concocted a simple
ruse. At the next big staff meeting, someone would casually mention that
a large number of DIA employees were on loan to outside agencies, a
common practice. Wilson would explode and announce a total freeze on
external assignments. The theatrics worked. Montes never knew that the
agency-wide moratorium was designed just for her. Dozens of supervisors
at other Washington agencies had called Wilson to complain, but the
bogus temper tantrum kept Montes out of the CIA.


Just as the FBI's criminal case was building steam, Montes fell in love.
She had begun dating Roger Corneretto, a senior intelligence officer who
ran the Cuban intelligence program for SouthCom, the military
installation the Wasp network had tried to infiltrate. Eight years her
junior, Corneretto was attracted to Montes's ambition, tight skirts and

Corneretto said that, at first, he enjoyed the challenge of trying to
woo the DIA "ice queen." "It took a long time for her to finally let me
in, and when she did I realized that warmth and niceness were not going
to come pouring out in a way to make up for how she was and for her
inexplicable hostility to good people," Corneretto recalled in a recent

Corneretto is married now and still works for the Pentagon. He
reluctantly agreed to discuss his ill-fated office romance. "As a close
community we were all fooled, but on top of that, I was even dating her,
so [my] sense of shame and guilt and failure and personal responsibility
was indescribable," he said. He calls Montes "an unapologetic, highly
educated, volunteer thug for a police state" and declares that "she will
never be off the hook with me."

Despite her boyfriend's obvious intel potential, investigators believe
that Montes's affections were real. She fantasized about starting a
family and ditching her espionage career. But her handlers refused to
let their top producer quit. "I'm a human being with needs that I
couldn't deny. I thought the Cubans would understand," she later
revealed to her debriefers. But spy agencies don't work that way. "She
naively believed that they would thank her for her assistance and allow
her to stop spying for them," the CIA commented in its analysis.


On May 25, 2001, Lapp and a small team of black-bag specialists slipped
inside Apartment 20. Montes was out of town with Corneretto, and the FBI
searched her closets and laundry bins, paged through shelves of neatly
stacked books and photographed personal papers. They spotted a cardboard
box in the bedroom and carefully opened it. Inside was a Sony shortwave
radio. Good start, Lapp thought. Next, techs found a Toshiba laptop.
They copied the hard drive, shut down the computer and were gone.

Several days later, a secure fax machine at the Washington field office
began churning out the translated contents of the hard drive. "That was
kind of our eureka moment," Lapp said.

The documents, which Montes had tried to delete, included instructions
on how to translate numbers-station broadcasts and other Spy 101 tips.
One file mentioned the true last name of a U.S. intelligence officer who
had been operating undercover in Cuba. Montes had revealed the agent's
identity to the Cubans, and her Cuban intelligence officer thanked her
by noting, "We were waiting here for him with open arms."

But the FBI needed more. It wanted the crypto codes that it was certain
Montes carried in her purse. It fell to Carmichael to design a plan so
Montes would abandon her pocketbook in her office. As described in
Carmichael's 2007 book, "True Believer," the elaborate stunt included a
bogus software glitch and a phony invitation to speak at a meeting just
one floor away. The conference-room location was close enough Montes
might not bring her pocketbook, and the meeting was kept short enough
that she wouldn't need her purse to buy lunch afterward.

On the day, two IT geeks huddled by Montes's cubicle to investigate an
annoying new computer malfunction. One of them happened to be FBI
Special Agent Steve McCoy. When her colleagues weren't looking, McCoy
tossed Montes's pocketbook into his toolbox and slipped off. The FBI
quickly copied the contents and returned the pocketbook. Inside her
purse were pager warning codes and a phone number (area code 917) later
traced to Cuban intelligence.

Without any eyes-on evidence of a dead drop of classified documents,
though, the FBI worried that Montes would be able to plea-bargain her
way out of trouble. But they were out of time. Hijacked planes had just
slammed into the Pentagon and the World Trade Center, and overnight the
DIA was on a war footing. Montes was named an acting division chief,
based on her seniority. Making matters worse, DIA supervisors who were
ignorant of the investigation had selected Montes as a team leader to
process target lists for Afghanistan. Wilson, the DIA director, had
demanded strict operational security regarding Montes. But now he wanted
her out of the way. Cuba had a long history of selling secrets to the
United States' enemies. If Montes obtained the Pentagon's war plan for
Afghanistan, DIA officials worried, the Cubans would eagerly pass the
information to the Taliban.

Carmichael came up with one final deception. On Sept. 21, 2001, a DIA
supervisor called Montes with an urgent request from the DIA inspector
general's office to help deal with an infraction by one of her subordinates.

Moments later, Montes appeared in the inspector general's office and was
ushered into a conference room, where McCoy and Lapp were waiting for
her. McCoy played good cop, suggesting vaguely that a technical source
or an informant had led them to her. Montes went pale and stared ahead,
blankly. McCoy soft-pedaled her culpability, hoping she might try to
offer innocent rationales for unauthorized contacts with Cuban
officials. But when Montes asked if she was under investigation and
requested a lawyer, the charade ended. "I'm sorry to tell you, but you
are under arrest for conspiracy to commit espionage," McCoy announced.
Lapp slapped on the handcuffs, and they escorted Montes out of the DIA
for the last time.

A nurse, oxygen tanks and a wheelchair had been positioned in the wings,
but the Queen of Cuba didn't need any help. "We figured she would just
kind of collapse, be a wreck," Lapp said. "And I think she could have
just carried both of us out on her back. She walked out that calm — I
won't say 'proud' — but with that kind of composure."

Later that day, an FBI evidence team scoured Montes's apartment for
hours. Hidden in the lining of a notebook they found the handwritten
cipher Montes used to encrypt and decrypt messages, scribbled shortwave
radio frequencies and the address of a museum in Puerto Vallarta,
Mexico, where she was meant to run in an emergency. The crib sheets were
written on water-soluble disappearing paper.


For Lucy Montes, Ana's arrest was humiliating. She and Tito had worried
they would lose their FBI jobs, and the anger kept coming in waves. But
for nearly a decade, Lucy saw little point in piling on against Ana. "I
thought it was better to be a sister and not a judge and jury," Lucy said.

But in late 2010, Ana went too far. From her Texas prison cell, she
wrote an angry letter suggesting that Lucy should see a psychologist to
deal with her latent rage. The hypocrisy was too much. "I thought now
would be a good time for me to tell you exactly what I think about you,"
Lucy replied on Nov. 6, 2010, in a two-page letter she shared with this
reporter. "I never told you before because … it seemed a cruel thing to
do since you were in prison. But you need to know what you've done to
all of us."

Lucy began by invoking their beloved mother, Emilia. "You should know
you ruined Mom's life. Every morning she wakes up devastated by what you
did and where you are," Lucy wrote. It's not enough, Lucy added, that
Mom "was married to a violent man for 16 years and raised four children
by herself. No, you had to ruin her final years when she should be
living in peace and contentment."

Then she turned to the rest of Ana's inner circle. "You betrayed your
family, you betrayed all your friends. Everyone who loves you was
betrayed by you," Lucy wrote. "You betrayed your co-workers and your
employer, and you betrayed your nation. You worked for an evil
megalomaniac who shares or sells our secrets to our enemies."

Finally, Lucy tore down Ana's tired rationalizations. "Why did you
really do what you did? Because it made you feel powerful. Yes, Ana, you
wanted to feel powerful. You're no altruist, it wasn't the 'greater
good' you were concerned for, it was yourself. You needed power over
other people," Lucy concluded. "You are a coward."

In interviews, Lucy refuses to make excuses for her sister. While her
late father did have a frightening temper, Lucy also remembers him as a
compassionate man with solid values. "We all grew up in the same
household, we all had the same parents, so you can't blame everything on
what happened at home," Lucy said. "If there's one thing my father
taught us, it's respect for the law and authority. It never even entered
my mind that my sister would be capable of such a thing, because we
weren't raised that way."


Ana Montes lives today at the Federal Medical Center Carswell in Fort
Worth, in a 20-inmate unit reserved for the nation's most dangerous
female offenders. She could have been charged with treason, a capital
offense, but pleaded guilty to espionage in exchange for a 25-year
sentence. She still has another decade to go. "Apparently it's pretty
horrific in there for her," Lucy says. "She says it's like being in an
insane asylum."

U.S. military and intelligence agencies spent years assessing the
fallout from Montes's crimes. At a congressional hearing last year, the
woman in charge of the damage assessment testified that Montes was "one
of the most damaging spies in U.S. history." Former National
Counterintelligence Executive Michelle Van Cleave told Congress that
Montes "compromised all Cuban-focused collection programs" used to
eavesdrop on high-ranking Cubans, and it "is also likely that the
information she passed contributed to the death and injury of American
and pro-American forces in Latin America."

Strict prison rules bar Montes from talking to the media and all but a
few friends and relatives. But in her private correspondence, she
refuses to apologize. Spying was justified, she says, because the United
States "has done some things that are terribly cruel and unfair" to the
Cuban government. "I owe allegiance to principles and not to any one
country or government or person," Montes writes in one letter to a
teenage nephew. "I don't owe allegiance to the US or to Cuba or to Obama
or to the Castro brothers or even to God."


Lucy Montes knows all about allegiance. When Ana walks out of prison on
July 1, 2023, Lucy will be waiting. She has offered to let Ana live in
her home for a few months, to get settled. "There's nothing acceptable
about what she did. On the other hand I don't feel like I can turn my
back on her, because she's my sister."

Jim Popkin is a writer living in Washington.

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