Talking to Strangers

by

Malcolm Gladwell

Talking to Strangers: Chapter 1 Summary & Analysis

Summary
Analysis
1. Gladwell begins by telling the story of Florentino Aspillaga, a high-ranking officer in Cuba’s General Directorate of Intelligence. In 1987, two years before the Iron Curtain fell, Aspillaga was running a consulting trading company called Cuba Tecnica out of Bratislava, Czechoslovakia. In reality, Cuba Tecnica functioned as a front for Cuban spy activity, and Aspillaga was a lauded official whom Fidel Castro had named intelligence officer of the year in 1985. Despite his achievements and status, however, Aspillaga grew disillusioned with the Communist cause and planned to defect in 1987.
During the Cold War, the Iron Curtain was the dividing boundary between Soviet-affiliated countries on the east side and NATO-affiliated (or neutral) countries on the west side.  Czechoslovakia was on the east side. Cuba, under Fidel Castro’s communist rule, was aligned with the Soviet Union (USSR) and was a point of contention between the USSR and the United States. Gladwell introduces Aspillaga’s story to show how the “stranger problem” that incited conflict between the Spanish and the Aztecs in the 16th century plays out in more recent history.   
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When it was time to go through with his plan, Aspillaga smuggled his Cuban girlfriend, Marta, over the border to Vienna, Austria. From there, the couple headed to the United States Embassy and turned themselves in. Aspillaga’s high rank gave him access to information about Cuba and the Soviet Union that was so sensitive that his former employers have twice tried to assassinate him. Since then, Aspillaga has lived a low-profile life under an assumed name. He has only been spotted once, by Brian Latell, who ran the CIA’s Latin American office. Latell’s meeting with Aspillaga occurred after Latell received a tip from Aspillaga’s go-between, an undercover agent. During the meeting, Aspillaga gave Latell the manuscript for his memoir that described an unbelievable story. 
Spy activity hinges on deception—on tricking strangers into not realizing that a misunderstanding has occurred between themselves and a person they don’t realize is a spy with foreign allegiances.
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2. After Aspillaga arrived at the American embassy in Vienna, Austria agents sent him to a U.S. Army base in Frankfurt, West Germany, for debriefing. Before the debriefing could begin, Aspillaga requested that a former Havana station chief known only to Cuban intelligence as “el Alpinista,” the Mountain Climber, be flown in to speak with Aspillaga. El Alpinista had served the CIA all over the world and was a role model to Aspillaga. Aspillaga’s request puzzled El Alpinista, but he traveled to Frankfurt to meet with him, nonetheless.
Austria and Vienna were on the west side of the Iron Curtain. Aspillaga’s desire to talk to el Alpinista suggests that he has insider information about Cuban intelligence he wants to share with el Alpinista. If this is the case, it supports Gladwell’s premise that humans are innately bad at making sense of strangers, since one would assume that el Alpinista, a renowned CIA officer and expert in counterintelligence, would be well-equipped to discern suspicious behavior or deception.
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Aspillaga and El Alpinista connected immediately, and it wasn’t long before Aspillaga shared his big secret: the CIA had a network of spies operating within Cuba to influence America’s perception of Cuba. Aspillaga began to list off dozens of CIA spies who operated as double agents for Cuba. Aspillaga’s list of double agents included nearly the entire force of U.S. soldiers inside Cuba, and their job was to give the CIA information especially curated by the Cuban government. El Alpinista tried to keep calm, but Aspillaga’s words alarmed him, since they implicated El Alpinista’s own people.
Aspillaga’s confession is a huge blow to el Alpinista, showing that Cuban double agents were so skilled at their job that they could fool a seasoned veteran in counterintelligence. But was it the double agents’ skill that allowed them to fool el Alpinista, or was it simply a matter of el Alpinista falling prey to the simple fact that people are bad at detecting deceit—even those, like el Alpinista, who are trained to detect it?
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El Alpinista and Aspillaga flew to Andrews Air Force Base outside Washington, D.C., to talk with higher-ups in the Latin American division. When Fidel Castro heard about Aspillaga’s betrayal, he assembled the double agents for a victory tour around Cuba, even releasing a documentary film about them featuring shockingly clear, high-quality footage the double agents had secretly filmed over the past 10 years. When the head of the FBI’s office in Miami received a copy of the documentary, the reality of the situation was clear: the Cuban government had completely duped the CIA.
Cuban double agents achieved the seemingly impossible feat of deceiving the CIA, one of the leading counterintelligence agencies in the world.  Gladwell introduces this ludicrous scenario to make a broader point about how common misunderstanding is in stranger interactions. It’s not only people who speak different languages, like Hernán Cortés and Montezuma II, who misunderstand each other. Even CIA agents whose training prepares them to detect deceit and discrepancies fell victim to misreading double agents’ allegiances and intentions.
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3. One aspect of Florentino Aspillaga’s story that doesn’t track is how the double agents were able to fool the CIA, which should be hypervigilant to such a threat. Looking back on Aspillaga’s unbelievable story, Latell can only speculate that Cuban double agents must have been very good at their job. El Alpinista argues that the CIA’s Cuban section had simply made “sloppy” work of monitoring Cuban intelligence. However, Gladwell reveals, the CIA’s East German division was just as compromised by spy activity as the Cuban Division. According to East German spy chief Markus Wolf, by the time the Berlin Wall fell, there wasn’t a single CIA agent who’d ever worked in East Germany who hadn’t been turned into a double agent.
Latell believes the Cuban double agents’ skill allowed them to evade detection. El Alpinista takes an opposite stance, suggesting that the CIA simply wasn’t as vigilant as they should have been. Gladwell disagrees with both positions, suggesting that nothing the CIA or double agents did or didn’t do would have changed the outcome of the situation, since agents failing to detect spy activity is a widespread occurrence that happens all the time. This implies, perhaps, that humans are fundamentally flawed at detecting when some is deceiving them. 
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Quotes
Aldrich Ames, for instance, was a senior officer assigned to Soviet counterintelligence who secretly worked for the Soviet Union. El Alpinista knew Ames personally, and while he admits to disliking Ames for being lazy, he insists that nobody could have suspected that he was a traitor. All this leads Gladwell to state Puzzle Number One: “Why can’t we tell when the stranger in front of us is lying to our face?”
Even Ames, who was thought of as a sloppy, lazy agent, was able to evade el Alpinista’s detection, which contradicts Brian Latell’s earlier claim that the double agents’ skillfulness was what allowed them to conduct their spy activity without attracting the CIA’s attention.
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