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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 ing 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 itted 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 ing 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 ed 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."

Between May and September of 2001, the FBI "maintained periodic physical surveillance" of Montes. Much of what the evidence reveals has to do with phone calls to the above-mentioned beepers. The surveillance intensified after September 11. On September 14, Montes was observed at the National Zoo making "what telephone records confirmed to be two calls to the same pager number she had called in May, June and August …" On September 15, "Montes made a call to the same pager number 11:12 a.m. that lasted one minute." On September 16, Montes "made a brief telephone call from a payphone in the Metro station at approximately 1:50 p.m., again to the same pager number." Five days later, Montes was picked up.

According to The Washington Post, Van A. Harp, the assistant director in charge of the FBI's Washington field office, said, "This has been a very important investigation because it does show that our national defense information is still being targeted by the Cuban intelligence service."

"There has not been what is called an 'assessment of damage' of what she [Montes] might have known and been able to compromise by making it available to the Cubans,'' Senator Bob Graham, the Florida Democrat who chairs the Senate Intelligence Committee, told The Miami Herald. "The offense that she committed is a capital offense,'' Graham added, explaining that Montes might reveal the extent of her activities in exchange for prosecutors not seeking the death penalty which appeared to be her motivation in accepting the plea agreement.

There's also a question of how does a young woman raised in Baltimore get to be a spy for Cuba. Ana Belen Montes was born on February 28, 1957, on a U.S. military base in Nurnberg, . Her father was a psychologist on the base; he died more than a year ago. The official details are sketchy, but the family moved back to the United States during Montes' childhood and settled for a time in Baltimore. She graduated from the University of Virginia and attended Johns Hopkins School of Advanced International Studies (SAIS) in Washington, D.C., where she received a master's degree in 1988.

"We're trying to reconstruct who her friends were, and we can't," Riordan Roett, director of Western Hemisphere studies at SAIS, told the Herald. "I took a look at her transcript and she took two of my classes." Roett only vaguely ed Montes.

"She was not a particularly engaging person," recalls Rand Corp. analyst Edward Gonzalez, professor emeritus at UCLA. "She was not happy. She never smiled." Gonzalez has written studies on Cuba for the U.S. military and intelligence establishment and would often run into Montes at military and professional conferences.

Montes began her career at the DIA as a junior analyst in 1985. She concentrated mainly on matters dealing with Central America. In a published report in late September, her supervisor at the time, who spoke on condition of anonymity, described Montes as introverted. "She was very private," the supervisor said. "She never attended parties. When we had office parties, she might show up for only a little while."

The Defense Intelligence Agency's mission and its charter is to "provide military intelligence to war fighters, defense policymakers and force planners, in the Department of Defense and the Intelligence Community, in of U.S. military planning and operations and weapon systems acquisition." Perhaps the most serious harm Montes caused came from how she used her position at the DIA to influence the way Cuba was perceived. Montes was described by sources in the intelligence community as "the go-to person on Cuba," and she would routinely brief military officers at the U.S. Southern Command in Miami. As a senior intelligence analyst, she visited Cuba at least twice, most recently in 1998.

In the mid-1990s, Montes would have been in a position to along "detailed analysis," former White House officials say, of what the United States was considering as a response to the shootdown in 1996 by the Cubans of two small planes belonging to the exile group Brothers to the Rescue. The two aircraft were being used for propaganda activities, dropping leaflets over Cuba.

Montes also participated in creating a 1997 DIA assessment of Cuba's military capacity. The conclusion of the DIA report was that Cuba was too weak since the fall of the Soviet Union to present a significant military threat to the United States. The Pentagon did not completely agree with that assessment as is reflected in a May 1998 letter accompanying the report that then-Defense Secretary William Cohen sent to of the Senate Armed Services Committee. Cohen wrote that while "the direct conventional threat by the Cuban military has decreased, I remain concerned about the use of Cuba as a base for intelligence activities directed against the United States … ."

The conclusion of the Pentagon's revised report, entitled "The Cuban Threat to U.S. National Security" (go to www.defenselink.mil for the entire letter and report), reinforces the notion that Cuba represents little conventional military threat to the United States. But the last line states: "Nonetheless, Cuba has a limited capability to engage in some military and intelligence activities which would be detrimental to U.S. interests and which could pose a danger to U.S. citizens under some circumstances."

Cuba, in the wake of September 11, was quick to dispel any suggestions that it was involved in any hostile actions against the United States. Cuba's foreign minister, Felipe Perez Roque, told reporters that day, "We deeply regret the loss of human life, and our position is of total rejection of this sort of terrorist attack." Perez also said that "any idea of Cuban involvement, I don't think that's even worth referring to. No one could be thinking such a barbarous thing."

President Fidel Castro, in a speech on September 22, said "Cuba … is opposed to terrorism and opposed to war. … Cuba reiterates its willingness to cooperate with every country in the total eradication of terrorism." He went on later in the speech to say, "Whatever happens, the territory of Cuba will never be used for terrorist actions against the American people and we will do everything within our reach to prevent such actions against that people. Today we are expressing our solidarity while urging peace and calmness."

The fact remains, however, that the U.S. Department of State lists Cuba among countries that terrorism, largely based on accusations that both Basque and Colombian terrorists are allowed to live in the country. And, in a statement released in early March 2002, the Bush istration said that it was investigating Cuba's links to international terrorist groups, as well as exploring the possibility that Cuba had the means to disrupt U.S. military communications. Some intelligence sources have speculated about the possibility that Cuba could have ed sensitive information on to other countries that are considered hostile to the United States, such as Iran and Iraq. And they cite the Montes case as part of an underlying concern that she could have had access to information about U.S. military deployments as the country prepared to attack Afghanistan. In a published report in late September, The Washington Post cited FBI sources that explicitly said that concern was the reason for Montes' arrest. But no official U.S. government source is pointing the finger at Cuba for involvement in any terrorist activities directed at America.

The question still remains: why did Ana Belen Montes become a spy for Cuba? "Most of these people recruit themselves," explains Dr. Jeffrey Richelson, an intelligence expert and senior fellow at the nonprofit National Security Archive and author of numerous books on foreign intelligence gathering, including A Century of Spies: Intelligence in the Twentieth Century. "I think in her case it's likely that there was an ideological affinity for the Cuban regime. From what I know, she always came down on the softer side of U.S. policy towards Cuba."

That might be explained by what some investigators see in Montes' family history. An shared by Marcelo Fernandez-Zayas, a Cuban exile and writer of the Web-based "Intelligence Report From Washington," indicates that when Montes was a child, her mother appeared on a radio talk show and expressed sympathetic views of the Castro regime. The response from a handful of Cuban exiles was critical, to say the least. This had to have an effect on the young Ana Belen, Fernandez-Zayas and others speculate. That and her mother's family history of participation in Puerto Rico's socialist party, they add.

Everyone agrees that Montes' motives were not financial. The evidence so far shows no large deposits into her bank , nor any extravagant spending. Friends say she was very focused on saving for retirement as a "single woman." Other friends say there might have been some romantic connection that led Montes into the arms of the Cubans. One friend recalls that Montes would go out dancing at clubs in the Washington area where Cubans from the Interests Section would go. That, however, seems to go against what most who knew Montes professionally believe. They describe her as "dour" and "not particularly friendly." They argue that the reason Montes became a spy has to be more about ideology and politics.

The other question to which an answer might never come is how U.S. counterintelligence became suspicious enough to start looking at Montes. "There could have been some evidence that the Cubans acted on some information Montes gave them and the U.S. noticed and began looking for a leak," Richelson hypothesizes. "Alternatively, there could have been a penetration of the Cuban [intelligence] services by the U.S. that revealed her existence."

Finally, apart from showing the world once again that U.S. intelligence agencies are highly penetrable, of what real use was Montes to the Cubans?

"It was probably of greater propaganda value to the Cubans in the intelligence area in of their status within the rest of the Cuban government," says Richelson, who believes that the damage Montes might have caused doesn't even approach what Robert Hanssen did. Throughout the entire Montes case, the Cuban government, and its representatives in Washington, declined to comment.

Others say the real prize in all this, little diminished by the conviction of Montes, is the influence on attitudes of those in the U.S. political establishment towards Cuba. The bottom line there is that the U.S. embargo is still in effect, but emergency relief was allowed last year by the Bush istration after a hurricane devastated parts of Cuba. How much will change now that the war on terrorism seems likely to expand to other countries is anyone's guess.

The potential that fallout from the Montes case will hurt the Cubans probably depends less on the story she told than the one truth that has pervaded the relationship between Cuba and the United States: whenever either needs a bogeyman, the other is always available.