The Queen of Cuba: A Selection from Malcolm Gladwell’s Talking to Strangers (2019)

“Ana Montes was a star. She had been selected, repeatedly, for promotions and special career opportunities, showered with accolades and bonuses. Her reviews were glowing. She had come to the DIA from the Department of Justice, and in his recommendation, one of her former supervisors described her as the best employee he had ever had. She once got a medal from George Tenet, the director of the CIA. Her nickname inside the intelligence community was the ‘Queen of Cuba.’ . . . From the day she’d joined the DIA, Montes had been a Cuban spy. . . . Right before she was arrested, the DIA found the codes she used to send her dispatches to Havana . . . in her purse. And in her apartment, she had a shortwave radio in a shoebox in her closet. . . .

Montes had a younger brother named Tito, who was an FBI agent. He had no idea. Her sister was also an FBI agent, who in fact played a key role in exposing a ring of Cuban spies in Miami. She had no idea. Montes’s boyfriend worked for the Pentagon as well. His specialty, believe it or not, was Latin American intelligence. His job was to go up against spies like his girlfriend. He had no idea. When Montes was finally arrested, the chief of her section called her coworkers together and told them the news. People started crying in disbelief. The DIA had psychologists lined up to provide on-site counseling services. Her supervisor was devastated. None of them had any idea. . . . The issue with spies is not that there is something brilliant about them. It is that there is something wrong with us. . . .

We have a default to truth: our operating assumption is that the people we are dealing with are honest. . . . We fall out of truth-default mode only when the case against our initial assumption becomes definitive. We do not behave, in other words, like sober-minded scientists, slowly gathering evidence of the truth or falsity of something before reaching a conclusion. We do the opposite. We start by believing. And we stop believing only when our doubts and misgivings rise to the point where we can no longer explain them away. . . . You believe someone not because you have no doubts about them. Belief is not the absence of doubt. You believe someone because you don’t have enough doubts about them. . . .

Ana Belen Montes grew up in the affluent suburbs of Baltimore. Her father was a psychiatrist. She attended the University of Virginia, then received a master’s degree in foreign affairs from Johns Hopkins University. She was a passionate supporter of the Marxist Sandinista government in Nicaragua, which the U.S. government was then working to overthrow, and her activism attracted the attention of a recruiter for Cuban intelligence. . . . Her new compatriots encouraged her to apply for work in the U.S. intelligence community. That same year, she joined the DIA—and from there her ascent was swift. . . .

She ranks as one of the most damaging spies in U.S. history. She had secretly visited Cuba on several occasions. After her arrest, it was discovered that Fidel Castro had personally given her a medal. Through all of that, there hadn’t been even a whiff of suspicion. . . . Ana Montes wasn’t a master spy. She didn’t need to be. In a world in which our lie detector is set to the off position, a spy is always going to have an easy time of it.”—Malcolm Gladwell, Talking to Strangers: What We Should Know about the People We Don’t Know (2019)