Cubanálisis El Think-Tank



Por Juan F. Benemelis





Ana BelEn Montes: A mole in the Pentagon





A few days after the terrorist attack of September 11 in New York, Ana Belen Montes, an analyst in the Defense Intelligence Agency for the Department of Defense, sent an email message to an old friend communicating to him that everything was fine and that she did not know any of the people who had died in the Pentagon.  “I can see the Pentagon burning from my office—she wrote--, anyway it pales compared to the World Trade Center; dark days await us; so much hatred”. 1  The days got rapidly darker, especially for Montes.  One week later, September 21, at 10:00 AM, after sending a letter to her family, FBI agents arrested her on the job for being the agile intelligence agency for Cuba, the General Directorate of Intelligence (DGI).



The FBI, who followed her movement’s months earlier, would have preferred to arrest her when she was setting up contact with supposed Cuban agents who controlled her activities.  The rhythm of Montes’ contacts with the Cuban intelligence had increased dramatically after the terrorist attack of September 11.  On September 14, the FBI surveillance trailed Montes while she abandoned the DIA to return to her house, located in an apartment complex on Connecticut Avenue, where she made an evasive maneuver to later make a call to a telephone locator owned by the Cuban Mission to the UN.  She also contacted the DGI again on September 15 and 16. 2


That precipitated the events, for fear that an agent embedded deeply in the US military intelligence system might pass secret information to Cuba about Washington’s response to said attacks. 3  “Those were the people who prepare the intelligence reports, and it is not possible to have someone you know is transmitting information to a hostile country when you are preparing to go to war; that forced the closing of the case much sooner than what they would have wanted”. 4


Ana Belen Montes, 44 years old, was the principal Cuba analyst in the DIA (Defense Intelligence Agency), the intelligence organ that provides the North American armed forces with political and strategic analysis, military capacity, the number and location of other countries’ troops.  Montes worked at Bolling, an Air Force Base, where one of the DIA’s sites is located.


Montes was the 17th spy arrested in the United States since September 1998, and she was the one who held the highest position of them all.  She was brought before the Federal Court in the District of Columbia, accused by the government of conspiracy to transmit to Castro’s espionage services a quantity of highly classified documents related to the national defense of the United States and the North American evaluations of Cuban armed forces.  Counterintelligence officials indicated Montes had access to a variety of U.S. military and intelligence secrets of interest to Havana, to terrorist groups, and to regimes allied with Castro.  Montes remained silent in the District Court and did not declare herself guilty; and the judge ordered her to be held without bond, and ordered that she be kept under suicide watch.  Later, on March 19, 2002, she plead guilty to having spied for the government of Fidel Castro for 17 years, incriminating herself in a charge of espionage that could bring a sentence of 25 years in jail with no possibility of parole.


The detention of this intelligence officer demonstrated that the Cuban espionage apparatus, despite the difficult financial situation of the country, was still very sophisticated and aggressive.  It could be the reason why the North American forces have failed to penetrate the higher levels of Cuban society.


As journalist Michael Waller said: 5 The successful penetration of the DIA by Cuba shows that the Havana regime, discarded by many as a week anachronism after the Soviet collapse, continues to be a serious intelligence threat.  Established by the Soviet KGB but refined and disciplined by the East German STASI, the DGI has surprised friends and enemies alike with its hampering and destruction of US human intelligence operations on the Island and by its capacity to penetrate academic, political and governmental institutions in the United States”. 6

“Cuba has not been able to spend (on those services) on the same scale as many other governments due to its lack of hard cash, however, the behavior of the DGI can be compared favorably to the best agencies of developed nations”, wrote the ex Major of the DGI, Juan A Rodriguez Menier in a still unpublished study carried out at the end of the 1990’s”. 7

One of the mysteries surrounding the case is the motive that caused Montes to commit that high act of betrayal against the United States.  According to prosecutors, she started working in the DIA, spying for Cuba for ideological reasons and not for the money, since she only received symbolic payments to reimburse her expenses.


Montes graduated from the University of Virginia in 1979 and received a Masters degree from Johns Hopkins University, School of Advanced Studies in 1988.  In the early 1980’s, Montes worked in the Office of Information and Privacy of the Department of Justice.

The character profile that emerges of Montes was the following: a single woman, brilliant and organized8, calm, very well known but with few friendships, very introverted and with little sense of humor9, she never attended parties, but in a position within the government capable of causing considerable damage10.




In 1985 Montes started working as an analyst for the DIA, rapidly moving up to high rank in the intelligence community.  Her fluency in Spanish and familiarity with Latin American issues helped her to reach her objectives.  First she concentrated on Nicaragua, and then in 1992 she went on to occupy herself with Cuban issues.  Her stay in that specialized job coincided with a period of tumultuous relations with Havana, the exodus of thousands of refugees in 1994 and 1995; the decision in Havana to shoot down civilian airplanes piloted by North Americans of Cuban origin; the approval in Congress of the Cuban Democracy Act which very effectively put a stop to the openings conceived by President Bill Clinton.

Montes avoided being promoted out of the Cuba area with the idea of staying in charge of the analysis.  She made use of a security pass that allowed her ample access to documents from various intelligence agencies, not just the DIA, and only about Cuba, such as satellite images, intercepted foreign communications and spy intelligence of other countries.


In 1990 she formed part of a group that visited Nicaragua several times with the objective of personally informing President Violeta Chamorro about the activities and the active Cubans in her country; Chamorro was facing a difficult situation with her army, still in the hands of the Sandinistas.  In 1992, Montes was selected by the CIA, along with a group of intelligence analysts who demonstrated talent, to receive a sabbatical course in the Center for Intelligence Studies.  From that moment on, she specialized in Cuba.

As the highest-ranking analyst on Cuba for the DIA, Montes traveled to Havana, in 1993, in a CIA financed operation with the objective of studying and familiarizing herself with the Cuban army.  There she succeeded in interviewing with Cuban generals to ask them about the economic reforms on the island.  Some sources have indicated that Montes entered into a relationship with an individual Cuban, and that perhaps that is what brought her to transfer her fidelity to Havana.  After that trip, she published a study of intelligence under the DIA about the attempts of the Cuban army to adopt administration tactics of the West with the idea of confronting the economic crisis in the island.  According to Edward González, the study was relevant and shed light on an aspect of the Cuban army until that moment unknown.11

In 1998, she returned to Cuba with two of Senator Jesse Helms’ assistants during the visit of Pope John Paul II.  After that trip, and possibly on other occasions, Montes collaborated so that the Pentagon would be convinced by the rational that since the fall of the Soviet Union, Cuba no longer presented a threat for the United States, because of its inability to project outside the territory.  This attempt to influence North American policy toward Cuba spread through high military and intelligence circles. 12


That report, prepared by Montes from the DIA, in coordination with the CIA’s National Counsel of Intelligence, the National Security Agency and the Office of Investigation of the Department of State, the U.S. Southern Command’s Joint Intelligence Center and the Office of the Secretary of Defense, considered the Cuban armed forces weak after the fall of the USSR.  Montes, however, tried to dilute the report and other agencies had to toughen it up conveying that the regime still presented a serious unconventional intelligence threat to the United States since its intelligence systems had suffered little damage. 13


Likewise, in one part of the same report dedicated to the biological war, it was set forth that the current scientific installations in Cuba could carry out the research and development of an offensive biological war, since its biotechnological industry is advanced with the capability of producing biological agents.  When Secretary of Defense William S. Cohen delivered his report to Congress, he added that he was worried about the potential of Cuba to develop and produce biological agents. 14


Fidel Castro himself referred to this report as follows: “There is another precedent:  the Pentagon analyzed the matter and made a fairly objective report. Immediately there was a reaction: the report was withheld, they tried to change the Pentagon’s report due to political reasons; there was a scandal. They were accusing the Pentagon of lying in relation to Cuba, that they were hiding the reality, in the end it was several weeks before they published the scandal; I don’t really know if there was some modification or not, but yes we read what was published about the introduction to the report, interpreting, distorting, planting confusions.  In other words, for political reasons they tried to lessen the objectivity of the report”. 15


From that moment on, many academics and high-ranking retired military of the United States began to repeat that Cuba did not present a threat to the national security of the United States.  Behind this consideration was hidden the intention to convince the North American administration that the best transition in Cuba was one controlled by the Castro brothers, with the support of the army, which would solve three basic issues of security for the United States:  avoid a massive immigration of Cubans; avoid a civil war inside Cuba which a US intervention would precipitate; and provide security for cooperation in the war on drug trafficking.


Everything seems to indicate that Montes fulfilled this disinformation task that molded the criteria of those who made Cuba policy toward those points.  Monte’s important position in the US intelligence community leads one to think that she influenced the official position on Cuba on important points of national security.  She participated in the seminars of the Study Group on Cuba at Georgetown University, where about 70 academics, intelligence analysts and other professionals involved in the Cuban topic congregated.


Her work allowed her to contact directly political executives and intelligence analysts from other government agencies.  Montes constantly held sessions on Cuban information and strategic considerations for members of Congress and the US Southern Command.  She met regularly with her counterparts in the CIA, and had access to secret intelligence reports in the internal computer network.  In the year 2000, she participated in meetings of the intelligence agencies during the seven months of the Elian Gonzalez custody problem.  One source described her desk as a warehouse of all kinds of intelligence information. 16   Due to the fact that Montes was a respected intelligence analyst, with an enviable history and no apparent motives of frustration with her superiors, her arrest came as a surprise in the intelligence community.


According to the FBI, she had been sending secret information about important US military operations to Cuba since 1991. 17    In fact, Montes attended military exercises of the U.S. Atlantic Command that took place in 1996.  In the accusation, the FBI determined that Montes was assigned by the DIA to participate in the military exercises that took place in Norfolk, Virginia




The FBI agents started to follow Montes periodically from the beginning of 2001, watching her when she visited stores in Washington, bookstores, gas stations, the zoo, and when she used public phones in the northeast of Washington and in Maryland.  On May 25th, FBI agents who were conducting surveillance on Montes, covertly entered her apartment with a search warrant and were able to retrieve a vast amount of information from her Toshiba laptop which were deleted from the hard drive, which contained secret information on the Department of Defense, including the military exercises conducted in 1996.  They also searched her Toyota Echo 2000 vehicle, red; her office at the Bolling Base and her safe deposit box at the bank.  Among the contents, there were instructions on how to erase material from the computer, methods utilized for radio reception, and references to the frequencies received through the radio.   Although she was under strict surveillance she was not limited to access classified materials, especially the highly classified on the Interlink; this one did not contain any operational plan for a possible response to terrorist attacks.


On a extensive, 17 page long accusation document, presented by FBI agent Stephen A. McCoy, there was detailed information on how she had, on reiterated occasions, maintained contact with the Cuban secret service, through high frequency radio transmissions, short wave, receiving numerical signals, through the same way used to de-codify her computer. 18   The technique utilized to receive codified data through short wave is commonly used by the Cuban intelligence.   The messages consisted in 150 numerical groups. The FBI determined that such precise numbers, in an exact order, were transmitted on 6 February 1999, in an AM frequency, through the 7887 kilohertz, and in the voice of a woman who spoke Spanish, and who introduced the transmission with the words “attention, attention”. 19

McCoy is the main FBI expert on Cuban espionage, with more than twelve years of experience operating against the DGI (General Directorate of Intelligence) and his equivalent in the communist party, the Department for America.  According to McCoy one of the forms of communication was using “a diskette that contains a deciphering program to convert the apparent group of numbers randomly selected into text in the Spanish language”.  In this same manner the DGI communicated with the Wasp Net in Florida, according to the FBI.  Montes “downloaded” confidential information or would enter it in a diskette in code and physically handed it over, directly or indirectly to her “controller” from the DGI.  The spy Robert P. Hanssen, who the counterintelligence say he actively monitored the surveillance done by the United States of the Cuban spies and its operations from their location as one of the main counterintelligence agents for the FBI, also communicated with his “controllers” from the KGB via computer diskettes in code, and would leave these in clandestine places utilized as mailboxes to be picked up.


The agents also found a short-wave Sony radio, and also receivers similar to the ones utilized by the Cuban spies of the Wasp Net.  Her portable computer contained various radial code frequencies, including numerical identical chains identical to the ones used by Cuba in their short wave transmissions that afterwards were de-codified by a program in Spanish. 20 These number transmissions utilized by Cuba in intercontinental short wave radio transmissions are received very easily and with great potency.  Here, the first two or three numbers of each group of five digits of the messages represent the pages of a book, and the two or three last, reading in between the lines; and with these, words can be composed.  The same book should be used for the receiver and the transmitter, and should not exceed 1,000 pages.  These messages can be again codified by computerized crypto-graphics.  Likewise, the key and the book change for each message, and the new code is included as part of the last message. 21

Hugh Stegman, editor of the short wave magazine Monitoring Time, making reference to how the Cubans utilized this communication system, said that the transmissions in numbers by short wave started to be listened all over the world shortly after the Cuba Missile Crisis in 1962, in several languages; and it was assumed that they were assigned to spies in different countries.  According to Stegman, ham radio operator sources were able to “triangle” these transmissions and detected that they proceeded from Cuba. 22   Montes utilized public telephones to contact her Cuban “controllers” from the UN mission in New York, calling her “locators” through code numeration. 


At the same time she delivered diskettes with numbered information to her controllers.  One of the texts recovered from her portable computer refers to “a particular access program related to the national defense of the United States”, that is so confidential that the FBI could not present, nor describe in the documents presented in court, for security reasons.  In a message that the FBI partially recovered from her computer, Montes expressed that she and another colleague “were the only ones in her office that knew such program”.  The DIA confirmed that on May 15, 1997 Montes and her colleague received training in how to operate such program. 23 An intelligence source expressed that apparently it referred to a highly classified system to store intelligence information via satellite and other technical means. 24


Another document describes how around the year 1996, Montes had informed her “controllers” at the Cuban DGI of the arrival to Cuba of a U.S. military intelligence agent that would operate undercover.  In the acknowledgment of receipt the Cuban intelligence answered:  “We are waiting here for him with open arms”. 25 According to the FBI, as a result the Government of Cuba could direct its counterintelligence resources against the American agent.  Subsequently, in her admittance of guilt statement, Montes confessed that among the Pentagon secrets that she delivered to Castro’s government were the names of four U.S. secret agents that were operating in the island.


In another response to Montes proceeding from her Cuban contacts you read: “Practically everything that occurs over there shall be of great intelligence value; let’s see if it has contingency plans and specific targets in Cuba”. 26 In another occasion Montes informed her Cuban controllers that the United States had become aware of the place, quantity and certain types of armaments in Cuba. 27


Contrary to the CIA, the Pentagon does not submit their intelligence analysts to polygraph tests to assure their loyalty on a periodic basis.  The sensitivity of the case is that Montes worked for the Pentagon, that had been a target of the September 11 terrorists attacks; and days before, the authorities of the Grand Cayman Caribbean island revealed that they had in their custody three afghans citizens suspected of being terrorists that had arrived in that country with false passports in a flight originating in Cuba. 


Montes detention shook the U.S. intelligence community where she was widely known; according El Nuevo Herald a serious investigation was unleashed within it, in search of accomplices. 28 It is noticeable that the arrest of Montes is produced a day after that the Gari couple of the Wasp Net confessed their involvement to the FBI, which leads us to think that there is a possible connection. The FBI informed that the methods for transmitting classified information utilized by Montes were the same as those used by the Wasp Net.  A source of the U.S. Congress expressed to a Sun-Sentinel reporter that Montes was identified in connection with the investigations of the Wasp Net. 29 According to the reporter Noah Adams, Montes had been recognized by one of the spies detained in Miami, a few months before. 30


Plato Cacheris and Preston Burton, a law firm with great experience in espionage cases, was able to obtain a plea bargain agreement with the prosecutors, where in exchange of cooperation and a declaration of guilt to one count of espionage, Montes received a significantly reduced sentence from the severe punishment she would face if convicted.  The prosecutors agreed to a 25-year jail sentence with no possibility of parole, followed by five years of supervised probation.  This is what normally happens in such cases, where you would negotiate to avoid the death penalty.  The other factor that leads to the acceptance of the quid pro quo by the federal prosecutors is that if Montes appears in trial, her attorneys would ask that all secret documents be made public, and this would greatly harm ongoing intelligence operations.


To accept the cooperation means that Montes would agree to be questioned by the DIA, FBI and CIA, and other departments that were victims of her actions, who would be interested in a thorough explanation of everything that has occurred, her contacts, information about its operational and technical Cuban espionage activities, and details of what Havana has revealed.




Everything seems to indicate that Ana Belen Montes caused enormous harm, since she knew the identity of U.S. secret agents in Cuba.  It is yet to be known how much damage was caused to the National Security in favor of Fidel Castro and performed by Montes, since she had access to a daily synopsis of American intelligence of all the countries in the world.  For an official who specialized in Cuba, Montes was in a position to know “90% of what we do in Cuba in the intelligence front and everything we knew about Cuba”. 31 Another official source expressed that she knew virtually all of what the intelligence community knew about the Cuban Armed Forces and surely led them to know what were the contingency military plans of the United States in case of an invasion of Cuba.


Alberto R. Coll, a high level Pentagon official during the George Bush, Sr., administration expressed that the harm could multiply if Cuba had shared this stolen intelligence with hostile governments against the United States. 32 According to diplomatic and federal sources the United States had serious indications that the government of Fidel Castro would exchange information with various Arab countries.  Montes had access to the Interlink, an electronic information web about intelligence matters where confidential documentation archives was gathered by various agencies. 33 Government sources informed the Washington Post that in other cases Cuba had transmitted information to Libya, Iran and other countries that have certain ties with the Saudi millionaire Osama Ben Laden. 34


The sub-director of the FBI office in Washington, Van A. Harp, would express that this had been and extremely important investigation that demonstrated how the United States national defense were still a target of Cuban intelligence services. Another high-level FBI official was in agreement with such opinion and added that the case “was very serious” because any information received by Cuba could have been shared with other foreign governments, causing damage. 35 “I don’t recall her expressing opinions in that study group”, declared the academic Wayne S. Smith. 


And even though Cuba has not expressed a public opinion about her arrest, Cuban diplomats in Washington justified the presence of spies in the United States.36 Florida’s representative, congresswoman Ileana Ros-Lehtinen, explained that this espionage case that Cuba is involved in, proves that you can not trust in Fidel Castro, and for this Cuba should continue in the list of states that promote terrorism.  “In reality, this could link Castro to the recent terrorist attacks, because his regime will continue to be a sworn enemy of the United States; Cuba is part of this terrorist net and what they do is sell information to our enemies”, concluded Ros-Lehtinen. 37


According to statements done to the Miami Herald from democrat senator Bob Graham from Florida and president of the Senate’s Intelligence Committee “the offense that she (Montes) has perpetrated is a capital offense”.38 Graham noted that time was needed for the accusers to determine if in this case of espionage the death penalty was applicable.


According to Richard Nuccio, a White House advisor on Cuba issues during president Bill Clinton’s administration, the fact that Montes was spying since 1996, placed her in an excellent position to send to Cuba details and analysis of the American military, due to the fact that after the incident in which Cuba knock down two Brothers to the Rescue planes in international waters, the White House requested the Pentagon to revise various scenarios, where the bombarding of landing Cuban zones and other possible military actions was included.  To have access to these military plans surely resulted of great use for a spy from Cuba. 39


On the other hand, Dennis Hays, the executive Vice-president of the Cuban American National Foundation, one of the best-organized and most powerful organizations, expressed that Montes was in such a position that she could compromise American intelligence sources and methods, not only in Cuba but also in other hostile countries.  The Cuban intelligence services—expressed Hays--, have strong ties with strong regimes such as Iran and Iraq. 40


The Executive Director for a Center for Free Cuba, Frank Calzon, expressed in Washington that her arrest validated the worries of the exiled Cuban community and of the legislator of Cuban origin elected in Congress regarding the extent of Cuban espionage operations in the United States.  “When these members of Congress expressed their concern, the response from certain political levels was that Castro was not a threat and that his main interest was to spy the exiled Cuban community; and now we have a case where an important intelligence officer has been caught and has been working for the Cuban government”. 41


Montes arrest puts in doubt the general evaluation of the Pentagon regarding that Cuba does not constitute a threat to the national security of the United States.  According to the El Nuevo Herald reporter Pablo Alfonso, “it is a proof of the candor that some politicians and American military leaders have judged Fidel Castro’s regime in the past months.  But Montes’s arrest will have more immediate repercussion will be without a doubt in the arguments utilized up to now in Havana and its representatives in the foreign countries and its representatives, to defend in Miami the presence of their net of agents, found guilty of spying for Cuba. 42


After accepting the guilt for Montes, Senator Graham demanded the government to reveal the details of the case that from what has been said, puts in manifest that Cuba is still a threat to the United States.  “The fact that some of our sensitive information of our national security is been compromised, is an indication of the continuous desire of Fidel Castro of harming the United States and the security of our country”, added Graham. 43


The Cuban press media did not make any comments about the arrest and the judicial trial of Montes.  Luis Fernandez, a diplomat from the Cuba Interests Section in Washington, expressed to the reporters that “he did not have any idea of what was been said and he did not know that woman”. 44 Another Cuban diplomat expressed the following:  “You have spies in Cuba; we have to find out what are your plans; we need to find out what type of operations are been done against us”. 45


After accepting guilt on the 19 of March of 2002, the District Federal Attorney of Columbia, Roscoe Howard, manifested that “this should sent a strong and clear message to anyone that engages in espionage activities against that country, that we will act with speed and that the price to be paid for this compromise will be high”.46 According to the FBI, Montes worked without receiving any compensation from the government of Cuba, differentiating from other spies that have received millions of dollars in jewelry and other luxury items.  “She conducted activities because she believed that the United States policy does not respect the Cubans, and is not even tolerant nor tries to understand them.  She was motivated by her desire to help the Cuban people and did not receive monetary compensation for this”, said Cacheris in the trial. 47




1.   Sun-Sentinel, Fort Lauderdale, Fl., October 1, 2001 Pg. 3(tm).

2.   J. Michael Waller, Vivitos y Coleando. Insight Magazine, 2001.

3.   El Nuevo Herald, Miércoles, 3 de octubre de 2001.

4.   Sun-Sentinel, Fort Lauderdale, September 28, 2001.

5.   J. Michael Waller, Ob. cit.

6..   J. Michael Waller, Ob. cit.

7. .  J. Michael Waller, Ob. cit.

8.   Sun-Sentinel, Idem.

9.   Tim Johnson, Saturday, September 29, 2001,

10. Sun-Sentinel, Idem.

11. Tim Johnson, Ob. cit.

12. Idem.

13. J. Michael Waller, Ob. cit.

14. J. Michael Waller, Ob. cit.

15. Granma, Nacionales. La Habana, 06/22/2001.

16. The Economist, September 29, 2001, U.S. Edition.

17. Contacto Magazine, 09/24/2001, pp. 2-4.

18. The New York Times, September 22, 2001.

19. Tim Johnson, Ob. cit.

20. J. Michael Waller, Ob. cit.

21. J. Michael Waller, Ob. cit.

22. Agencia EFE, Washington, 26 de septiembre, 2001.

23. Los Angeles Times, September 22, 2001, pag. 29.

24. The Washington Post, September 23, 2001.

25. Contacto Magazine, Idem.

26. Idem.

27. The Washington Post, September 23, 2001.

28. El Nuevo Herald, Miércoles, 3 de octubre de 2001.

29. Sun-Sentinel, Fort Lauderdale, Fl, September 22, 2001. Saturday Broward.

30. National Public Radio. October 4, 2001, 8:00 pm. ET.

31. The New York Times, September 23, 2001, P. 32.

32. Sun-Sentinel, Fort Lauderdale, Fl., October 1, 2001 Pg. 3(tm).

33. El Nuevo Herald, Miércoles, 3 de octubre de 2001.

34. AFP, Washington, Octubre 4, 2001.

35. The Washington Post, September 23, 2001.

36. Tim Johnson, Ob. cit.

37. Chicago Tribune, September 23, 2001, Pg. 19.

38. Tim Johnson, Ob. cit.

39. Tim Johnson, Ob. cit.

40. The New York Times, September 22, 2001.

41. The Washington Post, September 23, 2001.

42. El Nuevo Herald, 26 de septiembre del 2001.

43. Contacto Magazine. 03-19-2002.

44. Chicago Tribune, September 23, 2001, Pg. 19.

45. Tim Johnson, Ob. cit.

46. Contacto Magazine. 03-19-2002.

47. El Nuevo Herald; 20 de marzo, 2002.