Talking to Strangers

1. Gladwell resumes the Cuban spy story he began in Chapter One. The early 1990s ushered in a wave of Cuban refugees who fled from Cuba to the U.S. to escape Fidel Castro’s regime. They traveled the 90 miles of the Florida Straits on crudely fashioned boats, and up to 24,000 died while trying to complete the journey. In response to the refugee crisis, Cuban emigres living in Miami formed Hermanos al Rescate (“Brothers to the Rescue”), an air force of single-engine planes that patrolled the Florida Straits to look for refugees and forward their coordinates to the Coast Guard.

Over time, Cuban emigres expanded their territory into Cuba, flying over Cuban airspace and dropping down political leaflets that urged the citizens of Havana to rise up against Castro. Tensions brewed between the Cuban government and the emigres, culminating in Cuban Air Force fighters shooting down two Hermanos al Rescate planes, killing all four people onboard. At a press conference, President Bill Clinton and the U.S. government condemned Cuba’s actions.

However, coverage of the story changed after a retired U.S. rear admiral named Eugene Carroll revealed that he and some military analysts had met with Cuban officials the day before the air strike. On the visit, the Cuban officials asked what would happen if they were to shoot down one of the Hermanos al Rescate planes. When Carroll’s group relayed this concerning information to the U.S. Defense Intelligence Agency (DIA), CIA, and NSA, all three agencies failed to act on the threat. When Carroll’s admission went public, it was a huge embarrassment for U.S. intelligence, since the shoot-down had happened on February 24, a mere day after Carroll’s people had made the U.S. government aware of the threat. 

2. Gladwell draws attention to some of the air strike’s unsettling coincidences. For instance, isn’t it odd that a prominent Washington insider (Carroll) just so happened to disclose Cuba’s hypothetical plans to shoot down the Rescate planes the day before the air strike occurred? Furthermore, is it also a mere coincidence that Carroll went public with his claims on CNN the day after the attack?

A counterintelligence analyst named Reg Brown shares Gladwell’s suspicions. When the incident took place, Brown worked on the Latin American desk of DIA, and he was immediately suspicious that the Cuban government had orchestrated the entire crisis. One piece of evidence pointing to this conclusion was that Cuba had a source inside Hermanos al Rescate, a pilot, Juan Pablo Roque, who suspiciously disappeared before the attack, only to later reappear in Havana. Since it was likely Roque had informed his superiors of the Hermanos del Rescates’ plans to undertake a mission on February 24, it wouldn’t quite click that the date of Carroll’s briefing in Cuba had been selected by chance.

Brown’s investigations suggested that it was most likely one of his DIA colleagues—a Cuban expert named Ana Belen Montes, whose glowing reputation among the intelligence community earned her the nickname “Queen of Cuba”—who had picked February 23 as the date of Carroll’s briefing. This information troubled Brown, who was reluctant to accuse such a revered colleague of treason, but he finally came forward with his findings to a DIA counterintelligence officer named Scott Carmichael. Brown’s most damning evidence included a report he had compiled in the late 1980s attesting to senior Cuban officials’ involvement in international drug smuggling. A few days before Brown’s report was set to be published, every official he mentioned in the report issued a public denial of their involvement, and it was clear there had been a leak.

In 1994, two Cuban intelligence officers who defected confirmed Brown’s suspicion that there was a high-ranking informant inside American intelligence. In his report to Carmichael, Brown also revealed that Montes had worked at the DIA’s office on Bolling Air Force Base. Given Montes’s status as an expert on Cuba, she should have been at the scene to investigate the incident. Yet when Brown called the evening after the shoot-down occurred, he was informed that Montes had left the office after receiving a phone call that made her “agitated.” Brown became paranoid. His suspicions increased upon discovering that it was Montes who had arranged for Admiral Carroll’s meeting with the Cuban officials. 

Months later, Carmichael investigated Montes’s file and learned that she had passed her lie detector test and had no unusual activity in her bank account. Carmichael recalls believing that Brown must have been mistaken about Montes. After investigating Montes’s file, Carmichael met with Montes. He immediately took note of her intimidating demeanor. When Carmichael asked Montes about arranging the meeting with Admiral Carroll, Montes claimed that she’d only accompanied Carroll to Cuba and hadn’t arranged the meeting herself. When Carmichael asked Montes if the officer she claimed did set up the meeting would corroborate her story, she assured Carmichael that he would. Finally, when Carmichael asked about the troubling phone call Montes reportedly received the day of the shoot-down, Montes claimed not to have received the call. She insisted that she left work early due to a food allergy.

After Carmichael corroborated Montes’s information, he was convinced that Reg Brown’s concerns were unfounded. The investigation faded into obscurity until 2001, when it finally came to light that Montes had been operating as a spy all along. 

3. In spy novels, double agents are clever and elusive. Gladwell argues that this trope explains why CIA agents attributed Florentino Aspillaga’s admissions to Castro’s genius, for instance. In reality, however, villains are rarely so impressive or meticulous. For instance, Aldrich Ames was a lousy worker with a drinking problem, and Ana Montes kept the codes she used to communicate with dispatches in Havana in her purse. Brian Latell, a CIA Cuba specialist who worked closely with Montes, described her as strange and observably tense whenever he would ask her about Fidel Castro’s motives or other subjects concerning Cuban intelligence. Furthermore, when the CIA accepted Montes into their Distinguished Analyst Program and granted her the freedom to take a research sabbatical anywhere she chose, she opted to go to Cuba. In short, Montes made a number of sloppy decisions that should have raised red flags. 

And yet, even Montes’s brother—an FBI agent—had no suspicions about Montes. Montes’s boyfriend, who worked in Latin American intelligence in the Pentagon, also had no idea. Montes’s arrest shocked everybody. It shouldn’t have, though, given the signs that were all around them if they’d only chosen to look. In short, Gladwell concludes, there’s nothing special about spies—about “them.” Rather, there’s something flawed in “us.”

4. Tim Levine has dedicated much of his career to conducting variations on the same experiment. In this experiment, Levine invites students into his lab and asks them trivia questions to win a cash prize. An instructor assigns each student a partner who, unbeknownst to them, is working with Levine. Partway through the study, the monitoring instructor leaves the room. Then, the partner points to an envelope that contains the answers to the trivia questions. Arguing that they could really use the cash prize, the partner urges the test subject to cheat by looking at the answers in the envelope. About 30 percent of test subjects end up cheating. 

Gladwell includes a transcript of the interview Levine’s test subjects undergo after completing the trivia portion of the experiment. When the interviewer asks one subject, Philip, if he cheated, Philip mumbles noncommittal responses before stating “I guess. No.” Most people who watch Philip’s interview—Gladwell included—identify Philip as the cheating partner. Yet, as Levine shows additional subjects’ interviews to viewers, it becomes harder to discern which subjects are lying and which are telling the truth. Another subject, Lucas, appears more confident in his responses. The impulse for most viewers is to believe that Lucas is telling the truth. In reality, however, Lucas is lying.  

After hours of watching taped interviews with Levine, Gladwell can no longer tell who is deceptive and who is truthful. One would think that years of evolution would make us better at identifying human deception, laments Gladwell, yet Levine’s study proves otherwise. On average, viewers are able to correctly discern between liars and truthtellers just over 50 percent of the time.

Levine attributes people’s inability to detect deception to what he calls the “Truth-Default Theory,” or TDT. Levine’s theory was inspired by one of his graduate students, Hee Sun Park, who pointed out that the 54 percent deception-accuracy statistic “was averaging across truths and lies,” which is very different from how frequently people can identify truths and lies independently. While a person averages a 54 percent chance of discerning between truth and deception, they are considerably better at picking out truths than they are picking out lies. This is because humans have a “default to truth,” or an “assumption […] that the people we are dealing with are honest.” 

Levine’s experiment is an apt example of the “default to truth” phenomenon. One assumes that the students Levine invites to participate in his experiment aren’t that gullible. After all, they’re invited to partake in a psychological study for money, only to have a partner coerce them into cheating the moment the supervising instructor just so happens to leave the room. One would think that college students would catch on to this string of coincidences and recognize them as scripted components of the study. And yet, they don’t make the connection. While some students recognize that certain elements of the study must be a setup, they never suspect that their partners are in on it—that their partners would lie to them. 

According to Levine, engaging in the truth-default mode requires a “trigger.” A trigger is an action that compels a person to stop “gathering evidence” and start accepting the version of reality that lets them forget the initial misgivings they might have had about a potentially deceptive situation.

As an example, Levine cites Stanley Milgram’s infamous 1961 obedience experiment, in which subjects were assigned the role of “teacher” and asked to deliver increasingly powerful shocks of electricity to a “learner” named “Mr. Wallace.” The “teacher” would give Mr. Wallace memory tasks, and each time Mr. Wallace would fail, an experiment supervisor would order the teacher to administer increasingly powerful shocks as punishment. Teachers were under the impression that they were administering shocks to see whether receiving threats impacted a person’s memory. As the shock voltage increased, Mr. Wallace would cry out in pain. If the teacher hesitated, the monitoring instructor would urge them to continue, prompting them with commands like, “You have no other choice, you must go on.” In the end, most teachers complied with the instructor’s commands, and 65 percent administered the maximum voltage of 450 volts.

In addition to the Milgram experiment’s implications about compliance, Levine also believes the experiment offers compelling insight into human gullibility. In reality, the experiment was entirely staged. “Mr. Wallace,” the “learner,” wasn’t really administered electric shocks—he was an actor who was paid to cry out in agony to make subjects believe they were inflicting pain on another human. What’s more, Wallace wasn’t a particularly good actor. In fact, Gladwell notes, the whole production was “a little far-fetched” and unbelievable. Even so, many subjects fell for it and “defaulted to truth.”

Not all of Milgram’s subjects were so naive, however. In fact, many of them had serious doubts about the legitimacy of the experiment. One of the original test subjects believed that Wallace was faking his cries of pain. However, after Wallace emerged from the supposed shock room and put on an act of looking worn and emotional, the subject second-guessed himself. In the end, over 50 percent of Milgram’s subjects believed the learner was receiving painful shocks; 24 percent had doubts but believed; 6.1 percent was undecided; 11.4 percent believed the learner was probably not receiving shocks; and only 2.4 percent failed to fall for the setup. So, while over 40 percent of subjects had doubts about the experiment, those doubts weren’t enough to counteract their instinct to default to truth. This is the crux of Levine’s philosophy on deception: people don’t believe because they have no doubts—they believe because they “don’t have enough doubts[.]”

5. Ana Belen Montes grew up in a wealthy suburb of Baltimore, Maryland. She studied at the University of Virginia and received a master’s degree from Johns Hopkins University. She supported the Marxist Sandinista government in Nicaragua, which caught the attention of a Cuban intelligence recruiter who secretly brought her to Havana in 1985. Shortly after this, Montes joined the DIA and moved steadily up the ranks. When Scott Carmichael conducted his investigation of Montes, her coworkers described her as “focused” and “intelligent,” albeit somewhat “aloof” and reserved.

When Montes met with Carmichael, she assumed he was conducting a standard security check. She initially tried to call Carmichael off by claiming that she had just been promoted to Acting Division Chief and didn’t have a lot of time to spare. Carmichael initially played along with the lie, but when Montes pushed too hard, he came clean about his suspicions that she was involved in a counterintelligence operation. The accusation created an instant look of fear in Montes’s eyes. In retrospect, Carmichael realizes, it was this look that initially gave Montes away, since her reaction made no sense. Montes didn’t try to question the accusation or ask Carmichael to backtrack—she simply stared ahead in silence.

Carmichael remembers having doubts about Montes. But, as Levine would argue, doubt that one can reason oneself out of isn’t enough to “trigger disbelief.” And Carmichael was more than willing to reason himself out of believing that the “Queen of Cuba” was a spy. As Carmichael and Montes continued to talk, Montes relaxed and became almost flirty. She continued to insist that she had never received a phone call the day of the shoot-down. Although people who were in the situation room with Montes that day clearly remember her receiving a phone call, this red flag wasn’t enough to trigger Carmichael’s disbelief. Montes raised a final red flag when she became agitated when Carmichael asked her to recall her movements after leaving work the day of the shoot-down, specifically whether she saw anyone on her way home from work.

After Montes’s arrest, investigators discovered the truth about her movement that night. Cuban intelligence had a system in place where seeing one of her old handlers on the street was a signal to Montes that her spymasters needed to speak with her right away. When Carmichael later asked Montes if she had seen anyone she knew after leaving the office the night of the shoot-down, she must have assumed he was privy to this arrangement and aware of her spy activities. And yet, despite Montes’s clearly suspicious reaction to Carmichael’s question, he chose to rationalize her response. 

Gladwell concludes that while Montes was not a particularly talented spy, she didn’t need to be. In a world governed by the Truth-Default Theory, people are primed to ignore all manner of deceptive behaviors. According to Levine, it’s incredibly difficult to accumulate enough doubt that we are willing to reject the truth. Our instinct is to believe, and we will dismiss a high degree of doubt before we are willing to abandon belief. This logic provides us with an answer to the first puzzle of why Cuban intelligence was able to fool the CIA for so long: like all other humans, CIA agents have a bias toward truth.