Talking to Strangers

by Malcolm Gladwell

  You probably remember from high-school history how the encounter between Cortés and Montezuma ended. Montezuma was taken hostage by Cortés, then murdered. The two sides went to war. As many as twenty million Aztecs perished, either directly at the hands of the Spanish or indirectly from the diseases they had brought with them. Tenochtitlán was destroyed. Cortés’s foray into Mexico ushered in the era of catastrophic colonial expansion. And it also introduced a new and distinctly modern pattern of social interaction. Today we are now thrown into contact all the time with people whose assumptions, perspectives, and backgrounds are different from our own. The modern world is not two brothers feuding for control of the Ottoman Empire. It is Cortés and Montezuma struggling to understand each other through multiple layers of translators. Talking to Strangers is about why we are so bad at that act of translation.

  Each of the chapters that follows is devoted to understanding a different aspect of the stranger problem. You will have heard of many of the examples—they are taken from the news. At Stanford University in northern California, a first-year student named Brock Turner meets a woman at a party, and by the end of the evening he is in police custody. At Pennsylvania State University, the former assistant coach of the school’s football team, Jerry Sandusky, is found guilty of pedophilia, and the president of the school and two of his top aides are found to be complicit in his crimes. You will read about a spy who spent years undetected at the highest levels of the Pentagon, about the man who brought down hedge-fund manager Bernie Madoff, about the false conviction of the American exchange student Amanda Knox, and about the suicide of the poet Sylvia Plath.

  In all of these cases, the parties involved relied on a set of strategies to translate one another’s words and intentions. And in each case, something went very wrong. In Talking to Strangers, I want to understand those strategies—analyze them, critique them, figure out where they came from, find out how to fix them. At the end of the book I will come back to Sandra Bland, because there is something about the encounter by the side of the road that ought to haunt us. Think about how hard it was. Sandra Bland was not someone Brian Encinia knew from the neighborhood or down the street. That would have been easy: Sandy! How are you? Be a little more careful next time. Instead you have Bland from Chicago and Encinia from Texas, one a man and the other a woman, one white and one black, one a police officer and one a civilian, one armed and the other unarmed. They were strangers to each other. If we were more thoughtful as a society—if we were willing to engage in some soul-searching about how we approach and make sense of strangers—she would not have ended up dead in a Texas jail cell.

  But to start, I have two questions—two puzzles about strangers—beginning with a story told by a man named Florentino Aspillaga years ago in a German debriefing room.

  1 The idea that Montezuma considered Cortés a god has been soundly debunked by the historian Camilla Townsend, among others. Townsend argues that it was probably just a misunderstanding, following from the fact that the Nahua used the word teotl to refer to Cortés and his men, which the Spanish translated as god. But Townsend argues that they used that word only because they “had to call the Spaniards something, and it was not at all clear what that something should be.…In the Nahua universe as it had existed up until this point, a person was always labeled as being from a particular village or city-state, or, more specifically, as one who filled a given social role (a tribute collector, prince, servant). These new people fit nowhere.”

  Part One

  Spies and Diplomats:

  Two Puzzles

  Chapter One

  Fidel Castro’s Revenge

  1.

  Florentino Aspillaga’s final posting was in Bratislava, in what was then Czechoslovakia. It was 1987, two years before the Iron Curtain fell. Aspillaga ran a consulting company called Cuba Tecnica, which was supposed to have something to do with trade. It did not. It was a front. Aspillaga was a high-ranking officer in Cuba’s General Directorate of Intelligence.

  Aspillaga had been named intelligence officer of the year in the Cuban spy service in 1985. He had been given a handwritten letter of commendation from Fidel Castro himself. He had served his country with distinction in Moscow, Angola, and Nicaragua. He was a star. In Bratislava, he ran Cuba’s network of agents in the region.

  But at some point during his steady ascent through the Cuban intelligence service, he grew disenchanted. He watched Castro give a speech in Angola, celebrating the Communist revolution there, and had been appalled by the Cuban leader’s arrogance and narcissism. By the time of his posting to Bratislava, in 1986, those doubts had hardened.

  He planned his defection for June 6, 1987. It was an elaborate inside joke. June 6 was the anniversary of the founding of the Cuban Ministry of the Interior—the all-powerful body that administered the country’s spy services. If you worked for the General Directorate of Intelligence, you would ordinarily celebrate on June 6. There would be speeches, receptions, ceremonies in honor of Cuba’s espionage apparatus. Aspillaga wanted his betrayal to sting.

  He met up with his girlfriend Marta in a park in downtown Bratislava. It was Saturday afternoon. She was Cuban as well, one of thousands of Cubans who were guest workers in Czech factories. Like all Cubans in her position, her passport was held at the Cuban government offices in Prague. Aspillaga would have to smuggle her across the border. He had a government-issued Mazda. He removed the spare tire from the trunk, drilled an air hole in the floor, and told her to climb inside.

  Eastern Europe, at that point, was still walled off from the rest of the continent. Travel between East and West was heavily restricted. But Bratislava was only a short drive from Vienna, and Aspillaga had made the trip before. He was well known at the border and carried a diplomatic passport. The guards waved him through.

  In Vienna, he and Marta abandoned the Mazda, hailed a taxi, and presented themselves at the gates to the United States Embassy. It was Saturday evening. The senior staff was all at home. But Aspillaga did not need to do much to get the guard’s attention: “I am a case officer from Cuban Intelligence. I am an intelligence comandante.”

  In the spy trade, Aspillaga’s appearance at the Vienna embassy is known as a walk-in. An official from the intelligence service of one country shows up, unexpectedly, on the doorstep of the intelligence service of another country. And Florentino “Tiny” Aspillaga was one of the great walk-ins of the Cold War. What he knew of Cuba—and its close ally, the Soviet Union—was so sensitive that twice after his defection his former employers at the Cuban spy service tracked him down and tried to assassinate him. Twice, he slipped away. Only once since has Aspillaga been spotted. It was by Brian Latell, who ran the CIA’s Latin American office for many years.

  Latell got a tip from an undercover agent who was acting as Aspillaga’s go-between. He met the go-between at a restaurant in Coral Gables, just outside Miami. There he was given instructions to meet in another location, closer to where Aspillaga was living under his new identity. Latell rented a suite in a hotel, somewhere anonymous, and waited for Tiny to arrive.

  “He’s younger than me. I’m seventy-five. He’s by now probably in his upper sixties,” Latell said, remembering the meeting. “But he’s had terrible health problems. I mean, being a defector, living with a new identity, it’s tough.”

  Even in his diminished state, though, it was obvious what Aspillaga must have been like as a younger man, Latell says: charismatic, slender, with a certain theatricality about him—a taste for risks and grand emotional gestures. When he came into the hotel suite, Aspillaga was carrying a box. He put it down on the table and turned to Latell.

  “This is a memoir that I wrote soon after I defected,” he said. “I want you to have this.”

  Inside the box, in the pages of Aspillaga’s memoir, was a story that made no sense.

  2.

  After his dramatic appearance at the American embassy in Vienna, Aspillaga was flown to a debriefing center at a U.S. Army base in G
ermany. In those years, American intelligence operated out of the United States Interests Section in Havana, under the Swiss flag. (The Cuban delegation had a similar arrangement in the United States.) Before his debriefing began, Aspillaga said, he had one request: he wanted the CIA to fly in one of the former Havana station chiefs, a man known to Cuban intelligence as “el Alpinista,” the Mountain Climber.

  The Mountain Climber had served the agency all over the world. After the Berlin Wall fell, files retrieved from the KGB and the East German secret police revealed that they had taught a course on the Mountain Climber to their agents. His tradecraft was impeccable. Once, Soviet intelligence officers tried to recruit him: they literally placed bags of money in front of him. He waved them off, mocked them. The Mountain Climber was incorruptible. He spoke Spanish like a Cuban. He was Aspillaga’s role model. Aspillaga wanted to meet him face-to-face.

  “I was on an assignment in another country when I got a message to rush to Frankfurt,” the Mountain Climber remembers. (Though long retired from the CIA, he still prefers to be identified only by his nickname.) “Frankfurt is where we had our defector processing center. They told me a fellow had walked into an embassy in Vienna. He had driven out of Czechoslovakia with his girlfriend in the trunk of his car, walked in, and insisted on speaking to me. I thought it was kind of crazy.”

  El Alpinista went straight to the debriefing center. “I found four case officers sitting in the living room,” he remembers. “They told me Aspillaga was back in the bedroom making love with his girlfriend, as he had constantly since he arrived at the safe house. Then I went in and spoke to him. He was lanky, poorly dressed, as Eastern Europeans and Cubans tended to be back then. A little sloppy. But it was immediately evident that he was a very smart guy.”

  When he walked in, the Mountain Climber didn’t tell Aspillaga who he was. He was trying to be cagey; Aspillaga was an unknown quantity. But it was only a matter of minutes before Aspillaga figured it out. There was a moment of shock, laughter. The two men hugged, Cuban style.

  “We talked for five minutes before we started into the details. Whenever you are debriefing one of those guys, you need someone that proves their bona fides,” the Mountain Climber said. “So I just basically asked him what he could tell me about the [Cuban intelligence] operation.”

  It was then that Aspillaga revealed his bombshell, the news that had brought him from behind the Iron Curtain to the gates of the Vienna embassy. The CIA had a network of spies inside Cuba, whose dutiful reports to their case officers helped shape America’s understanding of its adversary. Aspillaga named one of them and said, “He’s a double agent. He works for us.” The room was stunned. They had no idea. But Aspillaga kept going. He named another spy. “He’s a double too.” Then another, and another. He had names, details, chapter and verse. That guy you recruited on the ship in Antwerp. The little fat guy with the mustache? He’s a double. That other guy, with a limp, who works in the defense ministry? He’s a double. He continued on like that until he had listed dozens of names—practically the entire U.S. roster of secret agents inside Cuba. They were all working for Havana, spoon-feeding the CIA information cooked up by the Cubans themselves.

  “I sat there and took notes,” the Mountain Climber said. “I tried not to betray any emotion. That’s what we’re taught. But my heart was racing.”

  Aspillaga was talking about the Mountain Climber’s people, the spies he’d worked with when he had been posted to Cuba as a young and ambitious intelligence officer. When he’d first arrived in Havana, the Mountain Climber had made a point of working his sources aggressively, mining them for information. “The thing is, if you have an agent who is in the office of the president of whatever country, but you can’t communicate with him, that agent is worthless,” the Mountain Climber said. “My feeling was, let’s communicate and get some value, rather than waiting six months or a year until he puts up someplace else.” But now the whole exercise turned out to have been a sham. “I must admit that I disliked Cuba so much that I derived much pleasure from pulling the wool over their eyes,” he said, ruefully. “But it turns out that I wasn’t the one pulling the wool over their eyes. That was a bit of a blow.”

  The Mountain Climber got on a military plane and flew with Aspillaga directly to Andrews Air Force Base outside Washington, DC, where they were met by “bigwigs” from the Latin American division. “In the Cuban section, the reaction was absolute shock and horror,” he remembers. “They simply could not believe that they had been had so badly, for so many years. It sent shock waves.”

  It got worse. When Fidel Castro heard that Aspillaga had informed the CIA of their humiliation, he decided to rub salt in the wound. First he rounded up the entire cast of pretend CIA agents and paraded them across Cuba on a triumphant tour. Then he released on Cuban television an astonishing eleven-part documentary entitled La Guerra de la CIA contra Cuba—The CIA’s War against Cuba. Cuban intelligence, it turned out, had filmed and recorded everything the CIA had been doing in their country for at least ten years—as if they were creating a reality show. Survivor: Havana Edition. The video was surprisingly high quality. There were close-up shots and shots from cinematic angles. The audio was crystal clear: the Cubans must have had advance word of every secret meeting place, and sent their technicians over to wire the rooms for sound.

  On the screen, identified by name, were CIA officers supposedly under deep cover. There was video of every advanced CIA gadget: transmitters hidden in picnic baskets and briefcases. There were detailed explanations of which park bench CIA officers used to communicate with their sources and how the CIA used different-colored shirts to secretly signal their contacts. A long tracking shot showed a CIA officer stuffing cash and instructions inside a large, plastic “rock”; another caught a CIA officer stashing secret documents for his agents inside a wrecked car in a junkyard in Pinar del Rio; in a third, a CIA officer looked for a package in long grass by the side of the road while his wife fumed impatiently in the car. The Mountain Climber made a brief cameo in the documentary. His successor fared far worse. “When they showed that TV series,” the Mountain Climber said, “it looked as though they had a guy with a camera over his shoulder everywhere he went.”

  When the head of the FBI’s office in Miami heard about the documentary, he called up a Cuban official and asked for a copy. A set of videotapes was sent over promptly, thoughtfully dubbed in English. The most sophisticated intelligence service in the world had been played for a fool.

  3.

  This is what makes no sense about Florentino Aspillaga’s story. It would be one thing if Cuba had deceived a group of elderly shut-ins, the way scam artists do. But the Cubans fooled the CIA, an organization that takes the problem of understanding strangers very seriously.

  There were extensive files on every one of those double agents. The Mountain Climber says he checked them carefully. There were no obvious red flags. Like all intelligence agencies, the CIA has a division—counterintelligence—whose job it is to monitor its own operations for signs of betrayal. What had they found? Nothing.1

  Looking back on the episode years later, all Latell could do was shrug and say that the Cubans must have been really good. “They did it exquisitely,” he said.

  I mean, Fidel Castro selected the doubles that he dangled. He selected them with real brilliance…Some of them were trained in theatrical deception. One of them posed as a naïf, you know…He was really a very cunning, trained intelligence officer…You know, he’s so goofy. How can he be a double? Fidel orchestrated all of this. I mean, Fidel is the greatest actor of them all.

  The Mountain Climber, for his part, argues that the tradecraft of the CIA’s Cuban section was just sloppy. He had previously worked in Eastern Europe, up against the East Germans, and there, he said, the CIA had been much more meticulous.

  But what was the CIA’s record in East Germany? Just as bad as the CIA’s record in Cuba. After the Berlin Wall fell, East German spy chief Markus Wolf wrote
in his memoirs that by the late 1980s

  we were in the enviable position of knowing that not a single CIA agent had worked in East Germany without having been turned into a double agent or working for us from the start. On our orders they were all delivering carefully selected information and disinformation to the Americans.

  The supposedly meticulous Eastern Europe division, in fact, suffered one of the worst breaches of the entire Cold War. Aldrich Ames, one of the agency’s most senior officers responsible for Soviet counterintelligence, turned out to be working for the Soviet Union. His betrayals led to the capture—and execution—of countless American spies in Russia. El Alpinista knew him. Everyone who was high up at the agency did. “I did not have a high opinion of him,” the Mountain Climber said, “because I knew him to be a lazy drunkard.” But he and his colleagues never suspected that Ames was a traitor. “It was unthinkable to the old hands that one of our own could ever be beguiled by the other side the way Ames was,” he said. “We were all just taken aback that one of our own could betray us that way.”

  The Mountain Climber was one of the most talented people at one of the most sophisticated institutions in the world. Yet he’d been witness three times to humiliating betrayal—first by Fidel Castro, then by the East Germans, and then, at CIA headquarters itself, by a lazy drunk. And if the CIA’s best can be misled so completely, so many times, then what of the rest of us?