Ana Belen Montes Character Analysis

Ana Belen Montes is a former U.S. Defense Intelligence Agency (DIA) agent. She began working as an informant for the Cuban government in 1985. Upon joining the DIA, Montes quickly made her way up the ranks to become an expert on Cuba, earning her the nickname “Queen of Cuba.” Counterintelligence analyst Reg Brown began to suspect that there was a Cuban informant operating within the DIA in the late 1980s. Brown’s focus narrowed on Montes after discovering it was she who had arranged the February 23 meeting between Admiral Eugene Carroll and Cuban officials. During the February 23 meeting, Cuban officials strongly hinted at the possibility of an attack on the Hermanos al Rescate planes. The next day, the Cuban Airforce shot down two Hermanos al Rescate planes. When the public learned that the DIA knew about the possibility of an attack but had failed to act, it painted the U.S. government as incompetent and ineffective. In 1996, DIA counterintelligence officer Scott Carmichael investigated Montes, though he initially found nothing suspicious in her files. When Montes’s counterintelligence activities ultimately came to light in 2001, the revelation shocked her colleagues. However, in retrospect, Montes made many mistakes over the years that simply went unnoticed. For example, she kept the codes she used to communicate with Havana dispatches in her purse. Ultimately, Gladwell attributes Montes’s ability to avoid detection for over a decade to humanity’s bias toward truth—not to her adeptness as a spy.