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The Cuban Spy Connection

An American female intelligence analyst was convicted in March of spying for Cuba for 16 years
CA Staff
From the Print Edition:
Cuban Spy Scandal, May/Jun 02

In September 11, the entire U.S. defense and intelligence establishment was put on high alert. Ships at sea went to "zip lip" status, meaning they ceased radio communications for fear of giving away their location. The Air Force began flying cover over U.S. territory. The uncertainty of the source of the attacks and whether more were coming meant that everyone had to be ready and all measures needed to be taken to maintain security.

However, one security breach wasn't closed for another 10 days, a lapse that puzzled many intelligence community sources. The FBI waited that long before arresting suspected Cuban spy Ana Belen Montes. She was a 45-year-old senior analyst on Cuba for the Defense Intelligence Agency (DIA), a group of more than 7,000 military and civilian employees worldwide who provide foreign military intelligence for the Department of Defense.

In a criminal complaint, the United States accused Montes of being a spy for Cuba. Her spying qualifies as one of the highest-level penetrations in the history of the DIA. On March 19, Montes pleaded guilty to one count of conspiracy to commit espionage, a charge that could have carried the death penalty, but in return for leniency, she agreed to cooperate with U.S. authorities. The court hearing revealed that she had spied for Cuba since beginning work at the DIA in 1985. The prosecutor, assistant U.S. Attorney Ronald Walutes Jr., reading the original indictment, said, "Montes used her position as an intelligence officer, and subsequently a senior intelligence analyst … to gather writings, documents, materials and information, classified for reasons of national security, for unlawful communication, delivery and transmission to the government of Cuba."

Montes was unavailable for comment after the plea hearing, but her lawyer, Plato Cacheris, told reporters that "she engaged in these activities because of her belief that U.S. policy does not afford Cubans respect, tolerance and understanding. She was motivated by her desire to help the Cuban people, and did not receive any compensation." Cacheris told Cigar Aficionado that "she took the 25 year sentence because if they tried it and we lost, she could have gotten life plus 40 years. The case would have been difficult for us to win." But he went on to say that the government "in order to learn the full extent of her activities, they had to make the deal. Otherwise, we weren't going to let her be debriefed." He declined to speculate further about her motivation.

But what remains clear is that in the wake of September 11, intelligence officials couldn't help but wonder to what extent Montes and other Cuban spies still at large could have compromised the national security of the United States. At the very least, her position in the DIA, and the information she had access to there, finally convinced counter-intelligence agents in the United States that it was too risky to allow her to remain in place at the DIA.

After tailing her beginning in May 2001, federal agents arrested Montes on September 21 in her DIA office at Bolling Air Force Base in Washington, D.C. Later that day, Walutes, the assistant U.S. Attorney, told the U.S. District Court in Washington that Montes "knowingly compromised national defense information" and claimed that Montes had harmed the United States. The affidavit supporting the complaint and arrest of Montes was filed by Special Agent Steven A. McCoy, a veteran of the FBI's counterintelligence unit and an expert on Cuban espionage. In the final plea agreement, Montes admitted to also revealing the identity of four U.S. agents to the Cuban Government. All four agents, according to U.S. Attorney Roscoe Howard are "alive and safe."

The original affidavit asserts that Montes committed two particularly egregious acts against the national security of the country. First, she had been passing details "about a particular top-secret Special Access Program (SAP) related to the national defense of the United States" to her Cuban handlers, at least one of whom was an official based in New York at Cuba's mission to the United Nations, according to U.S. investigators. SAPs usually have to do with either technical (satellite) or human intelligence gathering operations, to which few people are given access. In this case, as Montes seemed to brag to her Cuban handlers, "[J]ust today the agency made me enter into a program, 'special access top secret.' [First name, last name omitted from this application] and I are the only ones in my office who know about the program."

Second, Montes revealed the identity of a U.S. intelligence officer "who was present in an undercover capacity in Cuba," according to the original affidavit. The Cubans did not arrest the U.S. spy, but Cuban sources explained that the agent was identified and fed bad information. The affidavit seems to confirm that, saying that Cuba was "able to direct its counterintelligence resources" against the U.S. agent. "We were waiting here for him with open arms," the affidavit states, revealing a message from Cuba to Montes that was deleted but recovered from the hard drive of Montes' computer.

Affidavits are usually the most informative documents that ever become public in many spy cases. The government is often not interested in having a full trial, because information that could potentially compromise intelligence activities might have to be presented. That's why, as in the case of FBI mole Robert Hanssen, deals are made that might seem lenient, but they are made to protect ongoing operations. (Hanssen, a senior FBI counterintelligence agent who was arrested for spying for the old Soviet Union, monitored how the United States checked up on suspected Cuban agents and passed along that information to his KGB handlers.)

The public evidence against Montes was based largely on material found during at least two searches by federal agents of her Washington apartment. It included information about "the identities of foreign espionage agents" and "espionage paraphernalia, including devices designed to conceal and transmit national defense and classified intelligence information and material." The agents discovered more than 50 computer diskettes, and later found messages still on the hard drive of Montes' computer that had been "deleted." Among them, the FBI asserted, was a message from Montes' Cuban handlers at the Cuban Intelligence Services, or CuIS, according to the affidavit. The FBI stated that the instructions on the message duplicate the known methods by which Cuban agents have communicated with the CuIS, "by making calls to a pager number from a pay telephone booth and entering a pre-assigned code to convey a particular message." Montes was directed to communicate with beepers in the 917 area code. That's New York—where Cuba's mission to the United Nations is located. The recovered message from the CuIS on Montes' hard drive, according to the affidavit, listed three beeper numbers with codes. The message tells Montes to be cautious using one of the devices, "because this beeper is public, in other words it is known to belong to the Cuban Mission at the UN and we assume there is some control over it. You may use this beeper only in the event you cannot communicate" with the other two secure beepers. FBI agent McCoy explained in the affidavit that "control over it" means the CuIS officer suspects that the FBI "is aware that this beeper number is associated with the Cuban government and is monitoring it in some fashion."


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