April 21, 2013

Ana Montes betrayed her country and family for nearly two decades

By Jim Popkin P. 10

tom sietsema WEINGARTEN unhappy hours steak isn’t the a ‘date’? nope. boiling down @work advice P. 3 s tar here ... P.24 in date lab P.8 the news P. 29 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 two­bedroom co­op in Cleveland Park, Montes today lives in a two­bunk cell in the highest­security 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 14­page handwritten letter to a relative. “Or orn on a U.S. Army base in tes’s childhood made her intolerant of to Puerto Rico but could not find suit­ demanding assignment: spy in training. worth doing and then killing yourself before you have to spend too 1957, Ana Montes is the power differentials, led her to identify able work. When a friend told her about In 1984, the Cuban­intelligence service eldest child of Emilia and with the less powerful, and solidified her an opening as a clerk typist at the recruited her as a full­blown agent. much time in prison.” ¶ Like Aldrich Ames and Robert Hanssen Alberto Montes. Puerto Ri­ desire to retaliate against authoritarian Department of Justice in Washington, Sources close to the case think that a before her, Ana Montes blindsided the intelligence community co­born Alberto was a re­ figures,” the CIA wrote in a psychological she put her political considerations friend at SAIS served as a facilitator for Bspected Army doctor, and the family profile of Montes labeled “Secret.” Her aside. A job was a job. the Cubans, helping to identify potential with brazen acts of treason. By day, she was a buttoned­down GS­14 moved frequently, from Germany to “arrested psychological development” Montes excelled at the DOJ’s Office spies. Cuba considers recruiting at Amer­ in a Defense Intelligence Agency cubicle. By night, she was on the Kansas to Iowa. They settled in Towson, and the abuse she suffered at the hands of of Privacy and Information Appeals. ican universities a “top priority,” accord­ clock for Fidel Castro, listening to coded messages over shortwave outside Baltimore, where Alberto devel­ a temperamental man she associated Less than a year later, after an FBI ing to former Cuban intelligence agent radio, passing encrypted files to handlers in crowded restaurants oped a successful private psychiatric with the U.S. military “increased her vul­ background check, the Department of Jose Cohen, who wrote in an academic and slipping undetected into Cuba wearing a wig and clutching a practice and Emilia became a leader in nerability to recruitment by a foreign Justice granted Montes top­secret secu­ paper that the Cuban intelligence service the local Puerto Rican community. intelligence service,” adds the 10­page rity clearance. She could now review identifies politically driven students at phony passport. ¶ Montes spied for 17 years, patiently, methodical­ Ana thrived in Maryland. Slender, report.Lucyrecallsthatevenasateenager some of the DOJ’s most sensitive files. leading U.S. colleges who will “occupy ly. She passed along so many secrets about her colleagues — and the bookish and witty, she graduated with a Ana was distant and judgmental. “We positions of importance in the private advanced eavesdropping platforms that American spooks had 3.9 GPA from Loch Raven High School, were only a year apart, but I have to tell sector and in the government.” where she noted in her senior yearbook you that I never really felt close to her,” By night, she Montes must have seemed a godsend. covertly installed in Cuba — that intelligence experts consider her that her favorite things included “sum­ Lucy said. “She wasn’t one that wanted to She was a leftist with a soft spot for among the most harmful spies in recent memory. But Montes, now mer, beaches ... chocolate chip cookies, PREVIOUS PAGES: RADIO AND SURVEILLANCE PHOTOGRAPHS COURTESY OF FBI; FAMILY PHOTOGRAPH COURTESY OF THE FAMILY share things or talk about things.” was on the clock bullied nations. She was bilingual and 56, did not deceive just her nation and her colleagues. She also having a good time with fun people.” had dazzled her DOJ supervisors with betrayed her brother Tito, an FBI special agent; her former But the bubblegum sentimentality na Montes was a junior at her ambition and smarts. But most im­ masked a growing emotional distance, the University of Virginia for Fidel Castro, portant,shehadtop­secretsecurityclear­ boyfriend Roger Corneretto, a Cuban­intelligence officer for the grandiose feelings of superiority and a when she met a hand­ ance and was on the inside. “I hadn’t Pentagon;andhersister,Lucy,a28­yearveteranoftheFBIwhohas troubling family secret. some student during a listening to thought about actually doing anything won awards for helping to unmask Cuban spies. To outsiders, Alberto was a caring study­abroad program in untilIwaspropositioned,”Monteswould and well­educated father of four. But ASpain. He was from Argentina and a coded messages. later admit to investigators. The Cubans, behind closed doors, he was short­tem­ leftist, friends recall, and helped open she revealed, “tried to appeal to my con­ n the days after the Sept. 11, 2001, Ana, has been arrested for espionage, he pered and bullied his children. Alberto Montes’s eyes to the U.S. government’s viction that what I was doing was right.” terrorist attacks, the FBI’s Miami informed her, and she could face the “happened to believe that he had the support of authoritarian regimes. Spain Whileholdingdownherdayjob,Mon­ CIA analysts interpret the recruit­ field office was on high alert. Most death penalty. Your sister, Ana, is a right to beat his kids,” Ana would later had become a hotbed of political radi­ tes began pursuing a master’s degree at ment a bit more darkly. Montes was of the hijackers had spent time in Cuban spy. tell CIA psychologists. “He was the king calism, and the frequent anti­American the School of Advanced International manipulated into believing that Cuba South Florida, and FBI personnel Lucy didn’t scream, didn’t storm out of the castle and demanded complete protests offered a welcome diversion StudiesatJohnsHopkinsUniversity.Her desperately needed her help, “empower­ Ithere were desperate to learn whether in disbelief. Instead, she found the news and total obedience.” The beatings from schoolwork. “After every protest, political views hardened. Montes devel­ ing her and stroking her narcissism,” the any more had stayed behind. So when a strangely reassuring. “I believed it right started at 5, Lucy said. “My father had a Ana used to explain to me the ‘atroci­ oped a hatred for the Reagan administra­ CIA wrote. The Cubans started slowly, supervisor asked Lucy Montes to come away,” she recalled in a recent inter­ violent temper,” she said. “We got it with ties’ that the U.S.A. government used to tion’s policies in Latin America and espe­ asking for translations and bits of harm­ to his office, she didn’t blink. Lucy was a view. “It explained a lot of things.” the belt. When he got angry. Sure.” do to other countries,” recalls Ana cially for U.S. support of the contras, the less intel that might assist the Sandi­ veteran FBI language analyst who Major news organizations reported Ana’s mother feared taking on her Colón, a fellow college student who rebels fighting the communist Sandinista nistas, her pet cause. “Her handlers, translated wiretaps and other sensitive on the arrest, of course, but it was mercurial husband, but as the verbal and befriended Montes in Spain in 1977 and government in Nicaragua. with her unwitting assistance, assessed communications. overshadowed by nonstop coverage of physical abuse persisted, she divorced now lives near Gaithersburg. “She was Montes was now a budding Washing­ her vulnerabilities and exploited her But this impromptu meeting had the terrorist attacks. Today, Ana Mon­ him and gained custody of their children. already so torn. She did not want to be ton bureaucrat and a full­time student at psychological needs, ideology, and per­ nothing to do with Sept. 11. An FBI tes remains the most important spy Ana was 15 when her parents separat­ American but was.” one of the country’s premier universities. sonality pathology to recruit her and

squad leader sat Lucy down. Your sister, you’ve never heard of. ed, but the damage had been done. “Mon­ FAMILY THE OF COURTESY PHOTOGRAPH FAMILY After college, Montes moved briefly But she was about to take on another 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 From left: Friend Ana Colón, left, with Ana Montes in 1977; that would grant her great­ Montes in 1978; Montes, right, er access to classified infor­ at a party in Madrid in 1977; mation. She accepted a job Montes, in stripes, with, from at the Defense Intelligence left, father Alberto, sister Lucy, Agency, the Pentagon’s ma­ then-sister-in-law Joan and jor producer of foreign mili­ brother Tito at the FBI training facility in Quantico in 1989. tary intelligence. In an early mistake, Montes had confided to her old friend from Spain, Ana

april 21, 2013 | THE WASHINGTON POST MAGAZINE 13 Colón, that she had visited Cuba and had was promoted again and again. Montes Instead, she fastidiously memorized by Havana during the day but slip away to pying was lonely. Montes work was infiltrating Cuban exile organi­ had a fling with the cute guy who toured quickly became DIA’s principal analyst day and typed in the evenings, spewing brief her Cuban superiors. could confide only in her zations and making inroads into U.S. her around the island. Montes also re­ for El Salvador and Nicaragua, and later whole documents into a Toshiba laptop. Back in the States, when Montes handlers. Family gather­ military sites in Florida upon its capture. vealed that she was about to take a DIA was named the DIA’s top political and Night after night, she poured years’ needed to convey an urgent message, ings and holidays with her For Lucy, the Wasp case marked the job. “I was dumbfounded,” Colón re­ military analyst for Cuba. In the intelli­ worth of highly classified secrets onto she reached for a pager. Montes would two FBI siblings and their crowning achievement of her career. The called. “I couldn’t understand why some­ gence community and at DIA head­ cheap floppy disks bought at Radio seek out pay phones at the National Zoo, SFBI­employed spouses became tense FBI had called on her to translate hours body with her leftist beliefs would be quarters, Montes became known as “the Shack. the Friendship Heights Metro or by the affairs. At the beginning, the Cubans of wiretapped conversations of Cuban willing to work for the U.S.A. govern­ Queen of Cuba.” Not only was she one of Her tradecraft was classic. In Ha­ old Hecht’s in Chevy Chase to call pager provided enough of a social life. “They spies who were trying to penetrate the ment and for the military.” Montes said the U.S. government’s shrewdest inter­ vana, agents with the Cuban intelli­ numbers controlled by the Cubans. One were emotionally supportive. They un­ U.S. Southern Command base in Doral. she wanted to be part of the political preters of Cuban military affairs — gence service taught Montes how to slip beeper code would mean “I’m in ex­ derstood my loneliness,” Montes told Lucy earned praise from the FBI brass action and was “an American girl, after hardly surprising, given her inside packages to agents innocuously, how to treme danger”; another, “We have to investigators. But as she turned 40, and an award from a local Latin chamber all.”Butdaysaftertheconfession,Montes knowledge — but she also proved adept communicate safely in code and how to meet.” Schooled in spycraft by the KGB, Montes became despondent. “I was of commerce. But she never shared the cut her girlfriend off. Colón called and at shaping (and often softening) U.S. disappear if needed. They even taught the Cubans relied on the storied tools of finally ready to share my life with some­ news with Ana. Although Ana was one of wroteletterafterletterfor21/2 years,tono policy toward the island nation. Montes how to fake her way through a the trade. Montes’s pager codes and one but was leading a double life, so I the preeminent Cuba experts in the avail. Montes wouldn’t engage. Colón Over her meteoric career, Montes polygraph test. She later told investiga­ world and should have been ecstatic that never heard from Montes again. received cash bonuses and 10 special tors it involves the strategic tensing of her sister had helped expose a Cuban spy Back in Miami, Lucy Montes also was recognitions for her work, including a the sphincter muscles. It’s unknown if ring, Lucy was convinced Ana would just puzzled by her sister’s decision to work certificate of distinction that then­CIA the ploy worked, but Montes did pass a change the subject. “I knew she would for the Defense Department. But she Director George Tenet presented to her DIA­administered polygraph in 1994, have no interest in hearing about it or loved her sister and was so eager to make in 1997. The Cubans also awarded their after a decade of spying. talking about it,” Lucy said. a connection that she didn’t press the star student with a medal, a private Montes got most of her orders the But Lucy’s triumph became Ana’s point. Ana had become more introverted same way spies have since the Cold War: despair. Ana’s handlers suddenly went and rigid in her views since joining DIA. through numeric messages transmitted dark. They refused to contact her for “She would talk to me less and less about anonymously over shortwave radio. She months as they assessed the fallout from things that were going on with her,” Lucy Montes traveled would tune a Sony radio to AM frequen­ the investigation. “Something that gave said. Ironically, Ana now had much in cy 7887 kHz, then wait for the “numbers me fulfillment disappeared,” she later common with her siblings. Although to Cuba four station” broadcast to begin. A female toldinvestigators.Anabottomedout.She Juan Carlos, the baby of the family, had voice would cut through the other­ experienced crying spells, panic attacks become a deli owner in Miami, Lucy and times to meet worldly static, declaring, “Atención! and insomnia. She sought psychiatric her other brother, Alberto “Tito” Montes, Atención!” then spew out 150 numbers treatment and started taking antidepres­ had chosen careers helping to protect the with Cuba’s into the night. “Tres­cero­uno­cero­si­ sants. CIA­led psychologists would later United States. Tito had become an FBI ete, dos­cuatro­seis­dos­cuatro,” the conclude that the isolation, lies and fear special agent in Atlanta, where he still top intelligence. voice would drone. Montes would key of capture had triggered borderline ob­ works, and his wife was an FBI agent. the digits into her computer, and a sessive­compulsive traits. Montes began Lucy had become an FBI Spanish­lan­ Cuban­installed decryption program showering for long stretches with differ­ guage analyst in Miami, a job she still token of appreciation that Montes could would convert the numbers into Span­ ent soaps and wearing gloves when she holds, frequently working on cases in­ never take home. ish­language text. drove her car. She strictly controlled her volving Cubans. Her husband at the time She became a model of efficiency, a Montes also took the unusual risk of diet, at times eating only unseasoned worked for the FBI, too. warrior monk embedded deep within meeting the Cubans face­to­face. Every boiled potatoes. At a birthday party at Of her family members, only Lucy the bureaucracy. From cubicle C6­146A few weeks, she would dine with her Lucy’s home in 1998, Ana sat stone­faced would be interviewed. She agreed to talk at DIA headquarters at Joint Base Ana­ handlers in D.C. area Chinese restau­ and barely spoke. “Some of my friends for the first time — more than a decade costia­Bolling in Washington, she rants, where Montes would slide a fresh thought she was very rude, that there was after her sister’s arrest — to make her gained access to hundreds of thou­ batch of encrypted diskettes past tiny CIA Director George Tenet awards Ana did not feel I could live happily,” she something seriously odd with her. And views on Ana clear. “I don’t feel the way sands of classified documents, typically dishes of Chinese delicacies. The clan­ Montes a certificate of distinction for revealed. The Cubans set her up with a there was. She was cut off from her that a lot of her friends seem to feel, like taking lunch at her desk absorbed in destine handoffs also took place during her work in 1997. While Montes was lover, but after a couple of days of fun, handler,” Lucy said. excelling at her U.S. government job, she there’s a good excuse for what she did, or quiet memorization of page after page Montes’s vacations, on sunny Caribbe­ she realized she would not find happi­ Inside the DIA, the star analyst re­ was also excelling as a spy for Havana. I can understand why she did it, or, you of the latest briefings. Colleagues recall an islands. ness with a “mail order” groom. mained above suspicion. Montes had know, what this country did is wrong. that she could be playful and charming, Montes even traveled to Cuba four Ana’s alienation only grew when, by succeeded beyond the Cubans’ wildest There’s nothing to be admired,” Lucy especially with bosses or when trying to times for sessions with Cuba’s top intel­ shortwave­radio notes, for example, strange coincidence, Lucy began work­ dreams. She was now briefing the Joint said. talk her way into a classified briefing. ligence officers. Twice, she used a phony were written on specially treated paper. ing on the biggest case of her career: a Chiefs of Staff, the National Security But she also could be arrogant and Cuban passport and disguised herself in “The frequencies and the cheat sheet for massivecrackdownonCubanspiesoper­ CouncilandeventhepresidentofNicara­ or the next 16 years, Ana declined most social invitations. a wig, hop­scotching first to Europe to the numbers, that was all on water­solu­ ating in the United States. It was 1998, gua about Cuban military capabilities. Montes excelled — in both Montes would clock out at DIA, then cover her tracks. Two other times she ble paper,” explained the FBI’s Pete and the Miami field office had uncovered She helped draft a controversial Penta­ Washington and Havana. start her second job at her Macomb got Pentagon approval to visit Cuba on Lapp, one of two top agents on the case. a Cuban spy ring based in Florida, the gon report stating that Cuba had a “limit­ Hired by the DIA as an entry­ Street apartment in Cleveland Park. She U.S. fact­finding missions. She would “You throw it in the toilet, and it evapo­ so­called Wasp Network. More than a ed capacity” to harm the United States F level research specialist, she never risked taking a document home. meet at the U.S. Interests Section in AGENCY INTELLIGENCE DEFENSE THE OF COURTESY PHOTOGRAPH rates.” dozen members strong, the Wasp Net­ and could pose a danger to U.S. citizens

april 21, 2013 | THE WASHINGTON POST MAGAZINE 15 only “under some circumstances.” And she was about to earn yet another promo­ tion, this time a prestigious fellowship with the National Intelligence Council. An advisory body to the director of cen­ tral intelligence, the NIC was then at CIA headquarters in Langley. Montes was about to gain access to even more trea­ sured information. Her spy career would have reached unfathomable heights, had it not been for a back­bench DIA em­ ployee named Scott Carmichael.

ound­faced and often stuffed uncomfortably in size 44 suits from Macy’s, Carmichael defies the stereotype of the sophisti­ Rcated, Georgetown­trained mole hunt­ er. He laughingly describes himself as “a Kmart security guard,” but for the past quarter­century the former cop from Wisconsin’s dairy belt has hunted spies for the DIA. In September 2000, Carmichael got a hotlead.VeteranDIAcounterintelligence analyst Chris Simmons had been ap­ proached by a female intelligence officer. She had risked her career to inform Sim­ mons that the FBI had spent two years fruitlessly trying to identify a U.S. govern­ ment employee who appeared to be spy­ ing for the Cubans. It was an “UNSUB” case,meaningasearchforanunidentified subject. The FBI knew that the UNSUB had high­level access to U.S. intelligence on Cuba, had purchased a Toshiba laptop lysts had squealed on her, troubled by When FBI agents covertly searched to communicate with Havana and a few her occasionally aggressive efforts to Montes’s apartment in Cleveland Park, other tidbits. But with so few details, the access sensitive information. Carmi­ they found her laptop and the shortwave radio used to communicate with Cuba. FBI investigation had stalled. chael had even interviewed Montes and Carmichael got to work. He and his thought she had been lying. “I was left colleague Karl “Gator” James began with this nagging doubt,” he recalls. But Carmichael conceded there were inputting some of the FBI’s closely held Montes had been able to explain away all holes in his theory and reminded himself clues into their employee databases. DIA her actions, and Carmichael had closed that Montes was a stellar employee. He workers surrender many of their privacy the case. Now the computer screen was also knew that few women have been rights when applying for security clear­ blinking Montes’s name, and he was prosecuted for espionage in America ances, and Carmichael had access to convinced she must be a spy. “I knew, I since the Cold War. Still, Carmichael was reamsofpersonalfinancialrecords,med­ really knew it was her,” he said. certain he was on the right track. As he ical histories and detailed travel itinerar­ But the FBI was unimpressed. Lead walked out of the FBI that first day, he ies. The computer search produced more agent Steve McCoy riddled holes in Car­ swore a pledge. “I can remember looking than a hundred possible employee michael’s thesis, pointing out that many off, in the direction of the DIA and being matches. After scanning through about other federal workers and contractors so freakin’ pissed off,” Carmichael fumed Montes made contact with Cuban 20 subjects, the name “Ana Belen Mon­ matched the same circumstantial shreds years later. “I told Gator we’re going to intelligence at places such as tes” popped onto Carmichael’s screen. of evidence that had supposedly tied the Friendship Heights Metro, war. I said, ‘We’re getting rid of that ... Carmichael knew her. Four years Montes to the case. And some of Carmi­ the National Zoo and area woman, and these guys don’t know it yet,

earlier, one of Montes’s fellow DIA ana­ chael’s evidence made no sense. Chinese restaurants. GIRARD MATTHEW BY PHOTOGRAPHS but they’re opening a case on her.’ ”

april 21, 2013 | THE WASHINGTON POST MAGAZINE 17 Carmichael built a dossier on Mon­ Adding urgency was Montes’s pend­ espionage career. But her handlers tes and began badgering McCoy with ing promotion to the CIA advisory refused to let their top producer facts, dates and coincidences. He made council. Carmichael needed to quietly quit. “I’m a human being with excuses to stop by McCoy’s office to talk stall the assignment. With help from needs that I couldn’t deny. I about Montes and fill in holes. And then­DIA director Vice Adm. Thomas thought the Cubans would under­ when he was ignored, he went over Wilson, they concocted a simple ruse. At stand,” she later revealed to her McCoy’s head. the next big staff meeting, someone debriefers. But spy agencies don’t After nine weeks, Carmichael’s relent­ would casually mention that a large work that way. “She naively be­ less campaign paid off. McCoy was sold number of DIA employees were on loan lieved that they would thank her and persuaded headquarters to open a to outside agencies, a common practice. for her assistance and allow her to full investigation. “The bureau got really Wilson would explode and announce a stop spying for them,” the CIA lucky when the DIA came to us with total freeze on external assignments. commented in its analysis. Montes as a suspect,” said Pete Lapp, The theatrics worked. Montes never McCoy’s partner on the case. Despite knew that the agency­wide moratorium n May 25, 2001, their differences, McCoy says Carmichael was designed just for her. Dozens of Lapp and a small deserves a tremendous amount of credit supervisors at other Washington agen­ team of black­bag for his tenacity: “He broke the case. He cies had called Wilson to complain, but specialists slipped gave us our subject,” and “from that point the bogus temper tantrum kept Montes inside Apartment on, the FBI made the case.” out of the CIA. O20. Montes was out of town with Once the FBI was fully engaged, it Corneretto, and the FBI searched assigned more than 50 people to work ust as the FBI’s criminal case herclosetsandlaundrybins,paged the investigation and won permission was building steam, Montes through shelves of neatly stacked from a skeptical Foreign Intelligence fell in love. She had begun books and photographed personal Carmichael said: Surveillance Court judge to conduct dating Roger Corneretto, a papers. They spotted a cardboard surreptitious searches of Montes’s senior intelligence officer who box in the bedroom and carefully “We’re going to war. apartment, car and office. FBI opera­ Jran the Cuban intelligence program for opened it. Inside was a Sony short­ tives tailed Montes and filmed her mak­ SouthCom, the military installation the wave radio. Good start, Lapp We’re getting rid ing suspicious calls on pay phones. Lapp Wasp network had tried to infiltrate. thought. Next, techs found a used a national security letter, a form of Eight years her junior, Corneretto was Toshiba laptop. They copied the administrative subpoena, to gain unfet­ attracted to Montes’s ambition, tight hard drive, shut down the comput­ of that ... woman, tered access to Montes’s credit records. skirts and smarts. er and were gone. Montes, he learned, had applied for a Corneretto said that, at first, he en­ Several days later, a secure fax and these guys line of credit in 1996 at a CompUSA joyed the challenge of trying to woo the machine at the Washington field store in Alexandria. Her purchase? The DIA “ice queen.” “It took a long time for office began churning out the don’t know it yet.” same model of Toshiba laptop that the her to finally let me in, and when she did I translated contents of the hard FBI had learned about from its original realized that warmth and niceness were drive. “That was kind of our eureka source when it began its UNSUB inves­ not going to come pouring out in a way to moment,” Lapp said. tigation. “It was awesome, it was awe­ make up for how she was and for her The documents, which Montes some,” Lapp recalls. “This was regular inexplicable hostility to good people,” had tried to delete, included in­ old detective work.” Corneretto recalled in a recent e­mail. structions on how to translate Still, no one had witnessed Montes Corneretto is married now and still numbers­station broadcasts and Four years before persuading meeting a Cuban, typing coded messag­ works for the Pentagon. He reluctantly other Spy 101 tips. One file men­ the FBI to investigate her, Scott es at work or stuffing anything classified agreed to discuss his ill­fated office tioned the true last name of a U.S. Carmichael, a spy hunter for the Defense Intelligence Agency, into her pocketbook. For Lapp, then, romance. “As a close community we intelligence officer who had been had suspected Montes of lying there was a lot riding on the first were all fooled, but on top of that, I was operating undercover in Cuba. about accessing information. sneak­and­peek of Montes’s apartment. even dating her, so [my] sense of shame Montes had revealed the agent’s He needed concrete proof that Montes and guilt and failure and personal re­ identity to the Cubans, and her was a spy. Yet he couldn’t risk tipping sponsibility was indescribable,” he said. Cuban intelligence officer thanked her by 2007 book, “True Believer,” the elabo­ On the day, two IT geeks huddled by purse were pager warning codes and a her off with a messy search. “There’s no He calls Montes “an unapologetic, high­ noting, “We were waiting here for him rate stunt included a bogus software Montes’scubicleto investigateanannoy­ phone number (area code 917) later bigger stress that I’ve had professionally ly educated, volunteer thug for a police with open arms.” glitch and a phony invitation to speak at ing new computer malfunction. One of traced to Cuban intelligence. than being in someone’s apartment, state” and declares that “she will never But the FBI needed more. It wanted a meeting just one floor away. The them happened to be FBI Special Agent Without any eyes­on evidence of a legally, with them not knowing it and be off the hook with me.” the crypto codes that it was certain conference­room location was close Steve McCoy. When her colleagues dead drop of classified documents, having a chance to get caught,” said Despite her boyfriend’s obvious intel Montes carried in her purse. It fell to enough Montes might not bring her weren’t looking, McCoy tossed Montes’s though, the FBI worried that Montes Lapp, a former police officer. “You’re potential, investigators believe that Mon­ Carmichael to design a plan so Montes pocketbook, and the meeting was kept pocketbook into his toolbox and slipped would be able to plea­bargain her way being a cat burglar, legally, but you can tes’s affections were real. She fantasized would abandon her pocketbook in her short enough that she wouldn’t need her off. The FBI quickly copied the contents out of trouble. But they were out of time.

get caught, and the entire case is blown.” about starting a family and ditching her office. As described in Carmichael’s MORGAN MIKE BY PHOTOGRAPH purse to buy lunch afterward. and returned the pocketbook. Inside her Hijacked planes had just slammed into

april 21, 2013 | THE WASHINGTON POST MAGAZINE 19 the Pentagon and the World Trade Cen­ scribbled shortwave radio frequencies over other people,” Lucy conclud­ ter, and overnight the DIA was on a war and the address of a museum in Puerto ed. “You are a coward.” footing. Montes was named an acting Vallarta, Mexico, where she was meant In interviews, Lucy refuses to division chief, based on her seniority. to run in an emergency. The crib sheets make excuses for her sister. While Making matters worse, DIA supervisors were written on water­soluble disap­ her late father did have a fright­ who were ignorant of the investigation pearing paper. ening temper, Lucy also remem­ had selected Montes as a team leader to bers him as a compassionate man process target lists for Afghanistan. Wil­ or Lucy Montes, Ana’s arrest with solid values. “We all grew up son, the DIA director, had demanded was humiliating. She and in the same household, we all had strict operational security regarding Tito had worried they would the same parents, so you can’t Montes. But now he wanted her out of lose their FBI jobs, and the blame everything on what hap­ the way. Cuba had a long history of anger kept coming in waves. pened at home,” Lucy said. “If selling secrets to the United States’ en­ FBut for nearly a decade, Lucy saw little there’s one thing my father taught emies. If Montes obtained the Penta­ point in piling on against Ana. “I us, it’s respect for the law and gon’s war plan for Afghanistan, DIA thought it was better to be a sister and authority. It never even entered officials worried, the Cubans would ea­ not a judge and jury,” Lucy said. my mind that my sister would be gerlypasstheinformationtotheTaliban. But in late 2010, Ana went too far. capable of such a thing, because Carmichael came up with one final From her Texas prison cell, she wrote an we weren’t raised that way.” deception. On Sept. 21, 2001, a DIA angry letter suggesting that Lucy should supervisor called Montes with an ur­ see a psychologist to deal with her latent na Montes lives to­ gent request from the DIA inspector rage. The hypocrisy was too much. “I day at the Federal general’s office to help deal with an thought now would be a good time for Medical Center Car­ infraction by one of her subordinates. me to tell you exactly what I think about swell in Fort Worth, Montes: “I don’t Moments later, Montes appeared in you,” Lucy replied on Nov. 6, 2010, in a in a 20­inmate unit the inspector general’s office and was two­page letter she shared with this Areserved for the nation’s most owe allegiance to ushered into a conference room, where reporter. “I never told you before be­ dangerous female offenders. She McCoy and Lapp were waiting for her. cause ... it seemed a cruel thing to do could have been charged with the US or to Cuba McCoy played good cop, suggesting since you were in prison. But you need treason, a capital offense, but vaguely that a technical source or an to know what you’ve done to all of us.” pleaded guilty to espionage in informant had led them to her. Montes Lucy began by invoking their be­ exchange for a 25­year sentence. or to Obama or to went pale and stared ahead, blankly. loved mother, Emilia. “You should She still has another decade to go. McCoysoft­pedaledherculpability,hop­ know you ruined Mom’s life. Every “Apparently it’s pretty horrific in the Castro brothers ing she might try to offer innocent ratio­ morning she wakes up devastated by there for her,” Lucy says. “She says nales for unauthorized contacts with what you did and where you are,” Lucy it’s like being in an insane asy­ or even to God.” Cuban officials. But when Montes asked wrote. It’s not enough, Lucy added, that lum.” if she was under investigation and re­ Mom “was married to a violent man for U.S. military and intelligence quested a lawyer, the charade ended. 16 years and raised four children by agencies spent years assessing the “I’m sorry to tell you, but you are under herself. No, you had to ruin her final fallout from Montes’s crimes. At a arrest for conspiracy to commit espio­ years when she should be living in peace congressional hearing last year, nage,” McCoy announced. Lapp slapped and contentment.” the woman in charge of the dam­ on the handcuffs, and they escorted Then she turned to the rest of Ana’s age assessment testified that To build evidence against Montes out of the DIA for the last time. inner circle. “You betrayed your family, Montes was “one of the most Montes, FBI agents Steve A nurse, oxygen tanks and a wheel­ you betrayed all your friends. Everyone damaging spies in U.S. history.” McCoy, left, and Pete Lapp accessed her credit records and chair had been positioned in the wings, who loves you was betrayed by you,” Former National Counterintelli­ her home, and even copied the but the Queen of Cuba didn’t need any Lucy wrote. “You betrayed your co­ gence Executive Michelle Van contents of her pocketbook. help. “We figured she would just kind of workers and your employer, and you Cleave told Congress that Montes collapse, be a wreck,” Lapp said. “And I betrayed your nation. You worked for an “compromised all Cuban­focused think she could have just carried both of evil megalomaniac who shares or sells collection programs” used to eavesdrop correspondence, she refuses to apolo­ to the US or to Cuba or to Obama or to “There’s nothing acceptable about what us out on her back. She walked out that our secrets to our enemies.” on high­ranking Cubans, and it “is also gize. Spying was justified, she says, the Castro brothers or even to God.” she did. On the other hand I don’t feel calm — I won’t say ‘proud’ — but with Finally, Lucy tore down Ana’s tired likely that the information she passed because the United States “has done like I can turn my back on her, because that kind of composure.” rationalizations. “Why did you really do contributed to the death and injury of some things that are terribly cruel and ucy Montes knows all about she’s my sister.” Later that day, an FBI evidence team what you did? Because it made you feel American and pro­American forces in unfair” to the Cuban government. “I allegiance. When Ana walks scoured Montes’s apartment for hours. powerful. Yes, Ana, you wanted to feel Latin America.” owe allegiance to principles and not to out of prison on July 1, 2023, Jim Popkin is a writer living in Hidden in the lining of a notebook they powerful. You’re no altruist, it wasn’t Strict prison rules bar Montes from any one country or government or per­ Lucy will be waiting. She has Washington. To comment on this story, found the handwritten cipher Montes the ‘greater good’ you were concerned talking to the media and all but a few son,” Montes writes in one letter to a offered to let Ana live in her e­mail [email protected] or

used to encrypt and decrypt messages, for, it was yourself. You needed power friends and relatives. But in her private ARCHAMBAULT CHARLIE BY PHOTOGRAPH teenage nephew. “I don’t owe allegiance Lhome for a few months, to get settled. visit washingtonpost.com/magazine.

april 21, 2013 | THE WASHINGTON POST MAGAZINE 21