This paper examines the counterintelligence case of the infamous Cuban spy, Ana Montes. Ana Montes was able to conduct her espionage activities within the heart of the US intelligence community (IC) despite the IC’s recognition of a Cuban penetration. Throughout this paper the history and background of this spy will be discussed, detailing Ana Montes’ espionage operations and outlining the damage she posed to the US national security. An intelligence analysis and assessment have also been conducted, discovering Ana Motes’ betrayals of her country and the joint counterintelligence operation (mole hunt) conducted by the DIA and the FBI. This paper will also discuss the severity of the damage posed by Ana Montes as an “agent of influence” as she plainly shaped US foreign policy on Cuba, allowing Cuba and Russia the opportunity to reshape their strategic planning and foreign policy parallel to the US. Lastly, this paper will detail the accounts of the counterintelligence investigation bringing her to justice and putting an end to the era of Cuban intelligence success.
Insider threats, whether moles, double agents, or agents of influence, are one of the constant security risk counterintelligence services strive to detect, deter, and defend against. Ana Montes proved to be a challenging threat to detect and thwart. Her perfect persona and exemplary work ethics and record kept her seamlessly undetected for years while she spied for the Cubans, influenced US foreign policy pertaining to Cuban affairs, and was allegedly responsible for the shoot down of the Brothers to the Rescue (BTTR) in 1996 (Carmichael 2007, 7). The counterintelligence operation mounted against her also known as (Ana Montes’ counterintelligence case) by DIA counterintelligence officer Scott Carmichael and the FBI to detect the Cuban spy that operated in the heart of the US intelligence community was a pain staking operation (Johnson 2001). This operation was both a success and a failure to a certain extent, given Ana Montes had already caused grave damage by the time she was detected.
Ana Montes swiftly proved herself and was promptly advanced through the DIA ranks until she became a senior military and political analyst on Cuba in 1992 (Johnson 2001). It was during this time that Ana gained access to classified information of Cuban interest (Gertz 2007). Her deviousness and cleverness allowed her pass US classified materials to her Cuban handlers in Washington DC and in Cuba during her several unsuspected trips to Cuba (Gertz, 2007). Ana Montes was the Cuban mole that operated in the core of the US intelligence community, was able to influence US foreign policy on Cuba, and responsible of the deaths of several BTTRs, all because she sympathized for the Cuban people and deeply disagreed with the US foreign policy on Cuba, thinking that the US was too harsh on them (‘The Center for Counterintelligence and Security Studies”,).
The US counterintelligence services looked for the suspected Cuban spy everywhere. No one would have ever suspected her of any wrong doing if it was not for two situational aware DIA employees (Marquis 2001). Ana Montes was reported to the DIA counterintelligence office on two separate occasions four years apart. It was because of these reports that DIA counterintelligence officer Carmichael launched the counterintelligence operation to bring the Cuban spy down (Golden 2002). With the cooperation of the FBI, Carmichael was able to zero in on Ana Montes and blow her cover as the infamous Cuban spy that haunted Washington policy makers and intelligence officials (Golden 2002). Ana Montes was arrested in September 21, 2001 and was convicted of conspiracy to commit espionage for a foreign government. She pleaded guilty and received a sentence of 25 years in prison, followed by five year probation (‘The Center for Counterintelligence and Security Studies”,).
Ana Montes at DIA:
Ana Montes was recruited by the Cuban intelligence services while she was finishing her graduate degree in Advanced International Studies. By the time she obtained employment with the DIA in 1985, Ana Montes was a full-fledged Cuban spy (‘The Center for Counterintelligence and Security Studies”,). Ana Montes was an exemplary employee and her performance by her colleagues and supervisors was always rated as outstanding and described her as an “exceedingly rare” employee (Carmichael 2007, 54). She was the ideal candidate for the job. Given her Latina ethnicity and educational background, Ana Montes easily secured a position as an analyst on Latin affairs, Cuba specifically. She was rapidly promoted through the DIA’s ranks to the DIA’s senior intelligence analyst on Cuban politics and military affairs (Golden 2002). While employed by the DIA, Ana Montes had the perfect opportunity to satisfy her Cuban handlers’ intelligence thirst.
Ana Montes used her “pillar employee” status and access to highly classified US documents pertaining to Cuba, even Russia at times, to clandestinely gather intelligence and communicate it to her Cuban handlers in Washington DC (Golden 2002). Ana Montes was also able to communicate with the Cuban as she was able “to travel to Cuba at least four times while working for the DIA” as she was selected for the DIA’s Exceptional Analyst Program to study the Cuban military in1992 (‘The Center for Counterintelligence and Security Studies”,).
Ana Montes’ Espionage Methodology:
Ana Montes was extremely brilliant when it came to how she conducted her espionage activities. She was careful not to leave any trace linking her back to her misconduct. She did not remove any documents from her place of work, whether electronic or hard copies. Instead, “she kept the details in her head and went home and typed them up on her laptop. Then, she transferred the information onto encrypted disks.” (‘The Center for Counterintelligence and Security Studies”,) This way, she avoided the DIA’s security and counterintelligence branch from tracking her down early in her espionage career.
In addition, after Ana Montes received her commands from the Cubans through a short-wave radio, she then would meet with her handler and pass on the encrypted disks she made (‘The Center for Counterintelligence and Security Studies”,). Furthermore, Ana Montes contacted the Cubans over coded messages and received her guidelines through shortwave encoded broadcasts from Cuba (‘The Center for Counterintelligence and Security Studies”,). Finally, Ana Montes “communicated by coded numeric pager messages with the Cuban Intelligence Service by public telephones located in the District of Columbia and Maryland. The codes included ‘I received message’ or ‘danger’” (‘The Center for Counterintelligence and Security Studies”,).
National Security Damage Caused by Montes:
Ana Montes was considered one of the most damaging spies in US history. She was labeled as such due to her significant influence on US/ Cuban relations and loss of lives. Ana Montes’ analyses were guarded as very accurate and extensive by her supervisors as she became the DIA’s senior intelligence analyst on Cuban politics and military affairs (Marquis 2001). She was recommended to “help draft a 1998 official US Government finding that Cuba no longer presents a military threat to the United States” (‘The Center for Counterintelligence and Security Studies”,). Her involvement in shaping US foreign policy on Cuba caused grave damage to the US national security. In her trial, Ana Montes indicated that she did what she did solely based on ideology, as she stated “I believe our government’s policy towards Cuba is cruel and unfair, profoundly unneighborly, and I felt morally obligated to help the island defend itself from our efforts to impose our values and our political system on it. We have displayed intolerance and contempt towards Cuba for most of the last four decades. We have never respected Cuba’s right to make its own journey towards its own ideals of equality and justice”, she also added “I do not understand why we must continue to dictate how the Cubans should select their leaders, who their leaders cannot be, and what laws are appropriate in their land. Why can’t we let Cuba pursue its own internal journey, as the United States has been doing for over two centuries?” (‘The Center for Counterintelligence and Security Studies”,)
During the counterintelligence investigation mounted to thwart the Cuban mole operating within the heart of the intelligence community (IC), the FBI, CIA, and DIA investigators came to realize the damage caused by Ana Montes. Ana Montes provided the Cubans with a substantial amount of classified information about US foreign policy on Cuba and clandestine intelligence operations ongoing in Cuba to include the identities of four American spies (Gertz 2007).
Moreover, the counterintelligence officers determined based on the evidence mounting against Montes that she also provided the Cubans with information about a US Army Special Forces covert camp in El Salvador (Gertz 2007). The compromise of a highly classified US military camp and operation in El Salvador resulted in the death of a Special Forces soldier, Sgt. Gregory A. Fronuis, after the guerrillas of the FMLN attacked the camp on March 31, 1987. Counterintelligence officers concluded that Ana Montes was responsible for this betrayal after their investigation indicated that Montes was in Cuba only weeks before the camp was ambushed (Gertz 2007).
In addition, counterintelligence investigators believed that Ana Montes orchestrated the process “to be selected to represent the DIA for a special Cuba related joint project” to provide the Cubans with information about a “Brothers To The Rescue” mission that resulted in the shoot down of their plane by Cuban fighter jets in 1996 (Carmichael 2007, 9). She also disclosed CIA’s operations in Cuba to her handler because CIA operations encountered persistent obstacles in handling their Cuban agents after the same event.
The CI Investigation:
Ana Montes’ counterintelligence investigation was unlike any other of its time. The primary counterintelligence officer that was tasked to bring Ana Montes down before joining forces with the FBI was Scott Carmichael. Carmichael’s first technique was to develop “straw men” (Carmichael 2007, 31). These individuals “serve as a template against which investigators might measure potential suspects to gauge the likelihood that a particular suspect was a Cuban spy” (Carmichael 2007, 31). This technique failed Carmichael because it functioned on the preconceived bases that all possible spies are men. This method was based on the historical figures and statistics that indicated that “93 percent of males engage in espionage and only 7 percent were females” (Carmichael 2007, 36). This apparatus failed because it simply ruled out the probability of a female spy.
Carmichael than – with a little bit of common sense- zeroed in his attention to individuals that “would be employed as a specialist in Latin American Affairs” (Carmichael 2007, 31). Although this method was rather a possible big operation with multiple intelligence agencies to look into, it was plausible because it narrowed down the scope to intelligence professionals that specialize in Latin America’s affairs, a convenient position for a spy in need of Cuban information. Unfortunately, this technique did not yield any promising results either.
In 1996, Ana Montes’ colleague Reg Brown reported to the counterintelligence officer that “he felt Montes might be under the influence of Cuban intelligence” (‘The Center for Counterintelligence and Security Studies”,). Counterintelligence officer Carmichael interviewed Ana, but she answered every question confidently. Her responses checked out to be legitimate and truthful after Carmichael followed up her alibies. Ana Montes had also just passed a counterintelligence polygraph two years prior to her interview (Johnson 2001). It was until FBI counterintelligence officials were certain that there is a Cuban mole operating in the heart of the intelligence community, four years later, that counterintelligence investigator Carmichael “contacted the FBI with his suspicions” (‘The Center for Counterintelligence and Security Studies”,).
During the investigation, the FBI acquired court approval to enter and search Ana Montes’ apartment. Special agents found “a shortwave radio, an earpiece and a laptop computer.” (‘The Center for Counterintelligence and Security Studies”,) The FBI copied Ana Montes computer’s hard drive and repaired what she deleted. They also conducted a major physical and electronic surveillance operation and monitored her as she contacted her Cuban handlers on pay phone and sent coded messages (O’Grady 2002).
After the terrorist attacks of 9/11, the US intelligence community especially the DIA and the FBI did not want to wait any longer from fear that Ana Montes may again pass on intelligence to Cuba, intelligence that could be delivered to terrorists given Cuba’s relations with terrorist organizations. Ana Montes was aware of US military highly classified information about the impending invasion of Afghanistan in October 2001 (O’Grady 2002).
DIA and FBI did not want to give her the chance to pass that intelligence to the Cubans therefore the possibility of the Cubans passing it on to US adversaries (Gertz 2007). The FBI expedited Ana Montes’ arrest (Miller et al 2001). She was arrested on September 20, 2001 at DIA’s headquarters. Ana Montes was charged with “conspiracy to commit espionage 18 USC § 794 (a) and (c)” (‘The Center for Counterintelligence and Security Studies”,) because she used her position as a senior intelligence analyst to unlawfully provide and transmit highly classified US national security information to the Cuban government (Marquis 2001). Ana Montes received a twenty five year prison sentence and five years’ probation as a result of her deceitful and cowardly deed (Miller et al 2001).
Insiders threats are one of the persistent security risk counterintelligence services endeavor to detect, deter, and defend against. Ana Montes attested to the existence of such threats and the difficulty to detect and thwart them. Her perfect persona and exemplary work ethics and record kept her seamlessly undetected for years while she spied for the Cubans delivering highly classified information about US operations in El Salvador and Cuba, influenced US foreign policy pertaining to Cuban affairs, and was allegedly responsible for the shoot down of the Brothers to the Rescue (BTTR) in 1996 and the death of Special Forces Sgt. Fronuis (Carmichael 2007, 7). The counterintelligence operation mounted against her by DIA counterintelligence officer Scott Carmichael and the FBI to detect the Cuban spy that operated in the heart of the US intelligence community was a pain staking operation (Johnson 2001). This operation was both a success and a failure to a certain extent, given Ana Montes had already caused grave damage to US national security by the time she was detected. Ana Montes was unlike any other spy. She betrayed her country based on emotions and ideology. She believed that the US was unfair to the Cuban government and intolerant to their systems. Ana Montes was arrested in September 20, 2001 as the FBI expedited her arrest due of fears that she might provide the Cubans with more highly classified US information about the invasion of Afghanistan (O’Grady 2002). She was convicted of conspiracy to commit espionage for a foreign government. She pleaded guilty and received a sentence of twenty five years in prison, followed by five year probation (‘The Center for Counterintelligence and Security Studies”,) for her betrayal to her country and damages done to the US national security and foreign policy.
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