The Last Analog Spy
BOOK REVIEW: Queen of Cuba: An FBI Agent’s Insider Account of the Spy Who Evaded Detection for 17 Years
By Peter J. Lapp with Kelly Kennedy / Post Hill Press
Reviewed by Cipher Brief Expert Mark Kelton
The Reviewer — Mark Kelton retired from CIA as a senior executive with 34 years of experience in intelligence operations including serving as CIA’s Deputy Director for Counterintelligence. He is currently a partner at the FiveEyes Group; a member of the Board of Trustees of Valley Forge Military Academy and College; member of the National Security Advisory Board of the MITRE Corp.; member of the Day & Zimmermann Government Services Advisory Board; member of the Siemens Federal Advisory Board; and a member of the Board of BigMediaTV.
REVIEW — Although we are only a little over two decades into it, the 21st century has already seen a lengthy list of betrayals of country and oath that have done great harm to US national security. Bradley Manning, Edward Snowden, Harold Martin, Jerry Lee, Joshua Schulte and others of their ilk have all made headlines. Against such a malodorous backdrop, it is easy to forget this epoch began with the roll-up of one of the longest running espionage cases in American history.
In his book, Queen of Cuba: An FBI Agent’s Insider Account of the Spy Who Evaded Detection for 17 Years, former FBI Special Agent Peter J. Lapp tells the story of Ana Belen Montes, a senior Defense Intelligence Agency (DIA) Cuba analyst who spied for 17 years for the Cuban intelligence service (DI). It is a compelling insider view of Montes’s spying and the investigation that led to her 2001 arrest.
Mr. Lapp’s casual writing style could be off-putting to those who like their espionage history presented in a ‘just the facts’ manner. But I found it appropriate for a book that is at once a telling of the Montes story and a memoir of his FBI career. On the face of it, this duality might seem a distraction. But Lapp makes it work by juxtaposing his own background and service to our country with Montes’s upbringing and betrayal of that same nation. His examination of the converging paths that brought investigative target and investigator together is particularly poignant given Montes’s family ties: her brother was an FBI Special Agent and her sister a translator on the Bureau investigation of the Cuban Directorate of Intelligence (DI) ’s “Wasp” network.
Montes has been called the last ideological spy. What is meant by tha, is that she is seen as the last in a long line of American traitors motivated by fealty to Marxist-Leninist ideology; in her case, the Cuban strain of that deadly virus. Montes herself, Lapp tells us, “didn’t see herself as a communist…(she) sympathized with the goals of Cuban and Nicaraguan revolutions.” Given the seeming fascination these days of many young people with disguised versions of the same dogma – likely a result of having been imbued on college campuses with a sanitized version of the actual brutal history of a creed responsible for the deaths of tens of millions – that judgement of being “last” is surely premature.
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Though he doesn’t use these words, Lapp frames Montes as driven by a form of romanticism. Like many on the left in an earlier era, her path to serving a revolutionary cause went through Spain. Montes travelled there in 1977 on a college year abroad at a time when the country was moving from the Franco era towards democracy. She and her Puerto Rican friend “Mimi” moved in revolutionary circles. Their friends in Spain, as Lapp notes, were all anti-American. And it was there that Montes fell in love. Twice. First with a young Argentine singer who sang of revolution. He spoke with Montes of US support for authoritarian governments in Latin America. Their romance didn’t last. But her love affair has another ending. In her letters home, her sister noted, Montes called herself a “leftist” and wrote of “her newfound interest in Cuba.”
Someone other than her sister also took note because shortly after Montes enrolled at Johns Hopkins School of Advanced International Studies (SAIS) in 1982 she found a soulmate. Or, more likely, the soulmate found her. Montes and fellow-student Marta Velazquez quickly developed a friendship based on Montes’s growing anger over the Reagan Administration’s policies in Central America and her opposition to the invasion of Grenada. In 1984, Marta introduced Montes to a ‘diplomat’ accredited to the Cuban UN Mission. Over dinner in New York, DI officer Millan Chang-German soft-pitched Montes – who was then working at the Justice Department – to moonlight translating newspaper articles.
Millan need not have been so elliptical. Montes, Lapp writes, immediately pushed back, describing the work as menial and indicating she could do more. She readily agreed to Millan’s suggestion that she provide her “analysis of US government actions.” On the train back to Washington, Montes announced to Marta that if she was really going to help the Cubans she had to join the US intelligence community (IC). The Cuban DI seemingly knew early on what a golden opportunity they had in Montes. Marta told Montes the DI thought she “could be one of the best”. The best what went unsaid but was well understood. As requested, Montes typed out her biography on a DI-provided typewriter (thereby relieving her recruiter of what, in my own experience, can be an onerous requirement). The DI’s bet paid off when, in early 1985, Montes got an offer to join DIA as a Latin America analyst. (Interestingly, the Cubans did not press Montes to try to get a job at CIA, an organization she hated.)
In March 1985, Montes and Marta travelled together to Cuba via Madrid – where falsified passports were passed to them – and Prague. By the time Montes left the island, she and Marta had been trained on receiving encrypted radio traffic and how to beat the polygraph. Montes – who was given the work-name “Sonia” – left Cuba a fully recruited and trained agent of the DI. Montes’s sister rightly observed that by the time Montes walked into DIA for the first time in fall 1985, she had become “a full-fledged spy for Fidel Castro”.
Lapp details Montes’s climb within the fraternity of Latin American analysts to the point where she earned the moniker the “Queen of Cuba.” Her ruthless insistence on being right, underhanded tactics in securing plumb assignment and cold demeanor earned her no friends in the office. But her knowledge and work ethic were unquestioned. Montes cut a wide swath through the IC, attended conferences and established contacts she could leverage to the benefit of both DIA and the DI – the organization to which she owed her true allegiance. There were, however, times when she was unable to restrain herself from injecting her hidden convictions into her analytical work. Colleagues would later recall that her judgements regarding events in Cuba and Latin America sometimes revealed a bias in favor of the Castro regime. Such instances were apparently written off as legitimate differences of opinion. In retrospect, however, they should have revealed much about who and what Montes really was.
Montes might also be called the last analogue spy. Montes’s use of old-school methodology to defeat modern insider threat detection tools serves as a lesson-learned for those charged with protecting sensitive information from anyone seeking to emulate her. Montes, Lapp stresses, “never took anything home – no discs, no documents, no notes…She didn’t take pictures with a miniature camera or scan documents”. Instead, Lapp emphasizes, “every day she memorized three things she learned she thought the Cubans needed to know.” To paraphrase the author, ‘no technology (yet available) can detect evidence inside someone’s mind.’
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That is not to say Montes and the DI didn’t make mistakes that, if detected and pursued, might have resulted in her exposure. Complacency and operational friction can, especially in an operation lasting so long, mitigate against discipline and sound tradecraft. For instance, although she returned from Cuba in 1985 a recruited agent, that did not mean Montes had fully acclimated herself to the demands a secret life exacted. Shortly thereafter, she erred in telling Mimi she had visited the island. Realizing what she had done, Montes subsequently broke all contact with her old friend who, it turned out, had assumed Montes had travelled there on behalf of DIA. This was, as Lapp recounts, not the only alerting behavior Montes and the DI engaged in over the course of her time as a spy.
Others included:
- Montes’s refusal of jobs offering increased responsibility for fear of losing access to information of interest to Cuba.
- Her weekly meetings with her handler for lengthy lunches in the same Chinese restaurant in Washington. Per Lapp, the Bureau – which thought such direct personal contact too dangerous to risk – did not consider the possibility the DI might be hiding in plain sight. The DI, conversely, likely calculated that casual observers would write off a Hispanic male and female seen dining together as what it appeared to be.
- Her handler waving Montes down on the street to make emergency contact with her in the wake of the 1996 Cuban shoot-down of an aircraft flown by the exile group ‘Brothers to the Rescue’. Montes met with her handler every night during the crisis, providing him with read-outs on the US response to it. This extensive contact with the DI increased the potential risk of detection.
- A phone call – probably by the DI – to Montes during a Pentagon meeting on the shoot-down crisis. That call, and Montes’s consequent precipitous departure from the session, drew the attention of DIA colleagues including a counterintelligence (CI) officer who presciently concluded: “She’s no good. If I’m right, it’s bad, real bad.”
- Montes’s denial, in a resulting interview, that the phone call had even occurred. In that interview, conducted by the author of another book on the case, Montes handled other probing questions well, leading the interviewer to conclude she had, perhaps, denied the call occurred because she was embarrassed to speak of it as it involved a private matter.
- The soft-pedaling by Montes of the threat posed by the Cubans and her down-playing of the malevolence of the Havana regime raised concerns among some of her DIA colleagues. But this was ultimately ascribed to legitimate analytical disagreement.
- The 1998 recall of her handler to Cuba because he was “too close to the Wasp Network.” This was, as Lapp writes, bad tradecraft as it linked different operations, potentially jeopardizing both should one or the other be compromised.
- Trips by Montes to the Caribbean every six months after her handler’s recall to meet her new Cuban contacts. This pattern of ostensible “vacation” travel should have been alerting to CI personnel.
- And the fact, as Lapp establishes, that compartmentation of information regarding “Sonia” within the DI was poor; too many people knew her real name and about her activities.
Investigation of some of these oddities might, Lapp concludes, have put Montes at risk of detection. But they were largely ignored or discounted because, Lapp concludes, she herself was viewed as odd. A “vicious bureaucratic infighter”, Montes “was intellectually arrogant…(and)…a bully during meetings”. Her expertise, Lapp writes, made Montes “cocky to the point that her coworkers hated her”. Co-workers called her “la ostra” (the outsider). The views of her co-workers notwithstanding, Lapp observes that, on paper, Montes was “the model” employee. She worked long hours, writing on the Cuban “political environment, the stability of the regime, the accumulation of new weaponry”, etc. “Highly respected and…(having)…moved on up quickly,” Montes was seen by her superiors as being good at her job and was given broad access to the full range of intelligence on Cuba to do it. Moreover, she had passed a polygraph exam. Finally, the fact that female spies are a relatively rarity also mitigated against Montes coming under CI scrutiny.
Lapp describes the loneliness, stress and anxiety that plagued Montes. She could not, Lapp judges, maintain friendships at work, because “she saw the US government as an enemy…(and)…disagreed with what they did for a living.” Consequently, “instead of hanging out with her co-workers,” Lapp deduces, “she socialized with her handlers; she saw them as friends”. Attempts by Montes to find companionship in the form of a “Mr. X” provided by the DI at her request and a relationship with DIA colleague – “Roger” – whom she may have seen as an escape route from her in stressful life as a spy – are well documented by Lapp. Both of those quests for love went unrequited. “Mr. X” evoked “no spark”, and Roger – her ultimate deception of him aside – grew increasingly estranged from a woman whose attention and emotional attachment were directed elsewhere.
Lapp’s explication of his involvement in the counterespionage investigation that led to Montes will be the most illuminating part of the book for general readers. That investigation was – as virtually all successful counterespionage investigations are – facilitated by information delivered to the US from the heart of the adversary service. In Lapp’s words: “spies catch spies.” Even with such assistance, hunting a spy involves knitting often seemingly disparate, sometimes partial and all too often false pieces of information together into first a plausible; and later – as leads and theories are run to ground – verifiable; and, finally, a provable narrative. As Lapp explains, there were several indicators that spurred the Montes investigation. These included: information from a Cuban intelligence officer who defected in 1989 that a colleague told him he was handling two American agents, both women; and – in a coup reminiscent of the VENONA project – information from other Cuban defectors that granted the FBI the ability to read encrypted high frequency radio traffic sent by the DI to it agents in the US for what Lapp describes as a “brief period in 1996-1997”.
With the assistance of NSA, the FBI could read “a couple-dozen” messages the Cubans sent to a designated person, who the FBI would later learn was Montes’s handler. Those messages contained clues regarding an agent the DI called “Agent S” or “Sergio”. Among those hints was information indicating that Agent S had purchased a “Tandy” laptop computer at a store in “Alexandria” (presumed to be the Virginia city by that name based upon the range of the DI radio broadcast); reference to the agent’s travel to Guantanamo in the mid-1990’s; a report that the agent was in touch with a certain “WD”; mention of the agent using a SAFE system (a computer system the FBI would learn was used by DIA); indication that the agent passing information to the DI on floppy discs; information on the agent having had access to a specific CIA document and having travelled to Cuba at a certain time; and the password for the agent’s laptop: “NELEBAINOS”.
As Lapp makes clear, espionage investigations never proceed as envisioned. In this instance, investigators pursued false leads (e.g. the assumption that “Sergio” was male when, in fact, the Cubans had used a male name for their agent “Sonia” in an effort to mislead any hostile person gaining access to messages on the case), suffered from the inevitable “humbling” errors inherent in any such endeavor (e.g. when they realized the computer password contained part of Montes’s full true name and her work name spelled backwards), and were plagued at key moments by the proverbial “Murphy” (notably in the course of their initial attempt to covertly enter Montes’s apartment). I won’t spoil Lapp’s telling of how the investigation eventually identified Montes as a spy here. Suffice it to say it is both informative and entertaining.
One aspect of Lapp’s description of the conduct of the investigation bears mentioning. Lapp’s rightful pride in the FBI and in the people he worked with, his frankness in addressing past mistakes the Bureau has made (to include such episodes as the wrongful focus on CIA officer Brian Kelley as a suspected Russian spy and the abuse to the FISA process in the Carter Page case), and his determination not to repeat them in the course of this investigation make his narrative even more compelling.
The denouement of the story – Lapp’s debriefing as part of Montes’s sentencing agreement – is a particularly gripping read. Addressing the “what, when, where and how” of her spying with Montes was a relatively straightforward task for Lapp and his colleagues. As is always the case in such circumstances, the biggest challenge was determining why Montes betrayed her country. Born into a military family, her parents were both of Puerto Rican heritage, but not political. Much has been made of Montes’s resentment of her US Army doctor father, whom she has portrayed as authoritarian and abusive as a factor in her spying. Lapp cites an IC psychological assessment’s conclusion that “Montes’s childhood made her intolerant to power differentials, led her to identify with the less powerful and solidified her desire to retaliate against authoritarian figures.” That may well be true. But, as Lapp makes clear by citing his own background, not everyone with a difficult upbringing becomes a spy. Lapp’s own conclusion – that Montes was a narcissist; coldly indifferent to the impact her actions had on those around her and all too ready to blame others – makes sense. It also helps explain why Lapp came to hate her as their time together went on.
I found two aspects of Lapp’s recounting of his debriefing of Montes especially interesting for what it said about her true nature. The first concerns a trip Montes took to Central America at the behest of DIA in early 1987. Lapp makes a good case that the trip gave Montes access to information she passed to the DI that ultimately resulted in the death of Green Beret S/SGT Gregory Fronius in a rebel attack in El Salvador late that same year. Lapp found her answer of “I don’t remember” to his question of whether she met Fronius during that trip unconvincing. But her comment “that if she had, in fact, been responsible for his death, it was his own fault” because he had joined the US military and understood the risk was particularly damning.
Concern that Montes might share US military plans for responding to 9/11 terror attack with the Cubans, was the determining factor in the decision by the Department of Justice and FBI to arrest her. During her debriefing, Lapp asked Montes whether she would have passed the DI the US war plans if she’d had an opportunity to do so. Her reply; that she would have as “she believed she had a moral right to tell the Cubans how we fought a modern war in case we attacked Cuba;” was not surprising. But her follow-up remark that if Cuba gave the plans to Al-Qa’ida or the Taliban and it resulted in the deaths of more Americans, “Then that’s the risk they took” was jarring for what it said about her cold-bloodedness.
As is always the case in such instances – one need only think of John Walker’s exploitation of children, Harold Nicholson’s attempt to use his son to re-contact the Russians, and Robert Hanssen’s reprehensible treatment of his wife, Bonnie – Montes’s deceit resulted in family tragedy. Accordingly, Lapp conveys the damage Montes’s deception and betrayal did to her siblings and her mother. As Lapp relates, the former released a statement disavowing their sister’s “treason against this country and the people of our nation” while the latter – at first reluctant to acknowledge the truth – later sent a heartrending letter to her daughter detailing the disappointment and grief she felt on learning the allegations were true. As for Montes herself, her devotion to the Cuban cause would prove abiding. Even after a lengthy prison term, Lapp writes, she showed no remorse.
Lapp’s book gives the reader unique insight into the Montes case and will be of great interest to intelligence professionals and amateurs alike. The story he tells serves as a reminder that, even in the cyber age, a disciplined agent being run by a professional intelligence service using basic tradecraft can wreak great havoc. I hope today’s CI professional are paying attention.
Queen of Cuba earns a solid three out of four trench coats.
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