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Talking to Strangers

Malcolm Gladwell, host of the podcast Revisionist History and #1 bestselling author of The Tipping Point, Blink, Outliers, David and Goliath, and What the Dog Saw, offers a powerful examination of our interactions with strangers—-and why they often go wrong.

How did Fidel Castro fool the CIA for a generation? Why did Neville Chamberlain think he could trust Adolf Hitler? Why are campus sexual assaults on the rise? Do television sitcoms teach us something about the way we relate to each other that isn't true?

Talking to Strangers is a classically Gladwellian intellectual adventure, a challenging and controversial excursion through history, psychology, and scandals taken straight from the news. He revisits the deceptions of Bernie Madoff, the trial of Amanda Knox, the suicide of Sylvia Plath, the Jerry Sandusky pedophilia scandal at Penn State University, and the death of Sandra Bland—-throwing our...

Year:
2019
Publisher:
Little, Brown and Company6
Language:
english
Pages:
675
ISBN 13:
978-0-316-53562-5
File:
PDF, 4.56 MB
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Copyright © 2019 by Malcolm Gladwell
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Author photograph by Celeste Sloman
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Table of Contents
Cover
Title Page
Copyright
Dedication
Author’s Note
Introduction: “Step out of the car!”
Part One: Spies and Diplomats: Two Puzzles
Chapter One: Fidel Castro’s Revenge
Chapter Two: Getting to Know der Führer
Part Two: Default to Truth
Chapter Three: The Queen of Cuba
Chapter Four: The Holy Fool
Chapter Five: Case Study: The Boy in the Shower
Part Three: Transparency
Chapter Six: The Friends Fallacy
Chapter Seven: A (Short) Explanation of the Amanda Knox Case
Chapter Eight: Case Study: The Fraternity Party
Part Four: Lessons
Chapter Nine: KSM: What Happens When the Stranger Is a Terrorist?
Part Five: Coupling
Chapter Ten: Sylvia Plath
Chapter Eleven: Case Study: The Kansas City Experiments
Chapter Tw; elve: Sandra Bland
Discover More Malcolm Gladwell
Acknowledgments
Notes
Permissions
About the Author
Also by Malcolm Gladwell

For Graham Gladwell, 1934–2017

Explore book giveaways, sneak peeks, deals, and more.
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Author’s Note

Many years ago, when my parents came down to visit me in New York City, I
decided to put them up at the Mercer Hotel. It was a bit of mischief on my part.
The Mercer is chic and exclusive, the kind of place where the famous and the
fabulous stay. My parents—and particularly my father—were oblivious to that
kind of thing. My father did not watch television, or go to the movies, or listen to
popular music. He would have thought People magazine was an anthropology
journal. His areas of expertise were specific: mathematics, gardening, and the
Bible.
I came to pick up my parents for dinner, and asked my father how his day had
been. “Wonderful!” he said. Apparently he had spent the afternoon in
conversation with a man in the lobby. This was fairly typical behavior for my
father. He liked to talk to strangers.
“What did you talk about?” I asked.
“Gardening!” my father said.
“What was his name?”
“Oh, I have no idea. But the whole time people were coming up to him to
take pictures and have him sign little bits of paper.”
If there is a Hollywood celebrity reading this who remembers chatting with a
bearded Englishman long ago in the lobby of the Mercer Hotel, please contact
me.
For everyone else, consider the lesson. Sometimes the best conversations
between strangers allow the stranger to remain a stranger.

INTRODUCTION

“Step out of the car!”

1.
In July 2015, a young African American woman named Sandra Bland drove
from her hometown of Chicago to a little town an hour west of Houston, Texas.
She was interviewing for a job at Prairie View A&M University, the school
she’d graduated from a few years before. She was tall and striking, with a
personality to match. She belonged to the Sigma Gamma Rho sorority in college,
and played in the marching band. She volunteered with a seniors group. She
regularly posted short, inspirational videos on YouTube, under the handle
“Sandy Speaks,” that often began, “Good morning, my beautiful Kings and
Queens.”
I am up today just praising God, thanking His name. Definitely thanking Him
not just because it’s my birthday, but thanking Him for growth, thanking Him
for the different things that He has done in my life over this past year. Just
looking back at the twenty-eight years I have been on this earth, and all that

He has shown me. Even though I have made some mistakes, I have definitely
messed up, He still loves me, and I want to let my Kings and Queens know
out there to that He still loves you too.
Bland got the job at Prairie View. She was elated. Her plan was to get a
master’s degree in political science on the side. On the afternoon of July 10 she
left the university to get groceries, and as she made a right turn onto the highway
that rings the Prairie View campus, she was pulled over by a police officer. His
name was Brian Encinia: white, short dark hair, thirty years old. He was
courteous—at least at first. He told her that she had failed to signal a lane
change. He asked her questions. She answered them. Then Bland lit a cigarette,
and Encinia asked her to put it out.
Their subsequent interaction was recorded by the video camera on his
dashboard, and has been viewed in one form or another several million times on
YouTube.
Bland: I’m in my car, why do I have to put out my cigarette?
Encinia: Well, you can step on out now.
Bland: I don’t have to step out of my car.
Encinia: Step out of the car.
Bland: Why am I…
Encinia: Step out of the car!
Bland: No, you don’t have the right. No, you don’t have the right.
Encinia: Step out of the car.
Bland: You do not have the right. You do not have the right to do this.
Encinia: I do have the right, now step out or I will remove you.
Bland: I refuse to talk to you other than to identify myself. [crosstalk] I am
getting removed for a failure to signal?
Encinia: Step out or I will remove you. I’m giving you a lawful order. Get
out of the car now or I’m going to remove you.
Bland: And I’m calling my lawyer.
Bland and Encinia continue on for an uncomfortably long time. Emotions
escalate.
Encinia: I’m going to yank you out of here. [Reaches inside the car.]
Bland: OK, you’re going to yank me out of my car? OK, all right.

Encinia: [calling in backup] 2547.
Bland: Let’s do this.
Encinia: Yeah, we’re going to. [Grabs for Bland.]
Bland: Don’t touch me!
Encinia: Get out of the car!
Bland: Don’t touch me. Don’t touch me! I’m not under arrest—you don’t
have the right to take me out of the car.
Encinia: You are under arrest!
Bland: I’m under arrest? For what? For what? For what?
Encinia: [To dispatch] 2547 County FM 1098. [inaudible] Send me another
unit. [To Bland] Get out of the car! Get out of the car now!
Bland: Why am I being apprehended? You’re trying to give me a ticket for
failure…
Encinia: I said get out of the car!
Bland: Why am I being apprehended? You just opened my—
Encinia: I’m giving you a lawful order. I’m going to drag you out of here.
Bland: So you’re threatening to drag me out of my own car?
Encinia: Get out of the car!
Bland: And then you’re going to [crosstalk] me?
Encinia: I will light you up! Get out! Now! [Draws stun gun and points it at
Bland.]
Bland: Wow. Wow. [Bland exits car.]
Encinia: Get out. Now. Get out of the car!
Bland: For a failure to signal? You’re doing all of this for a failure to signal?
Bland was arrested and jailed. Three days later, she committed suicide in her
cell.

2.
The Sandra Bland case came in the middle of a strange interlude in American
public life. The interlude began in the late summer of 2014, when an eighteenyear-old black man named Michael Brown was shot to death by a police officer
in Ferguson, Missouri. He had just, allegedly, shoplifted a pack of cigars from a
convenience store. The next several years saw one high-profile case after another

involving police violence against black people. There were riots and protests
around the country. A civil rights movement, Black Lives Matter, was born. For
a time, this was what Americans talked about. Perhaps you remember some of
the names of those in the news. In Baltimore, a young black man named Freddie
Gray was arrested for carrying a pocket knife and fell into a coma in the back of
a police van. Outside Minneapolis, a young black man named Philando Castile
was pulled over by a police officer and inexplicably shot seven times after
handing over his proof of insurance. In New York City, a black man named Eric
Garner was approached by a group of police officers on suspicion that he was
illegally selling cigarettes, and was choked to death in the ensuing struggle. In
North Charleston, South Carolina, a black man named Walter Scott was stopped
for a nonfunctioning taillight, ran from his car, and was shot to death from
behind by a white police officer. Scott was killed on April 4, 2015. Sandra Bland
gave him his own episode of “Sandy Speaks.”
Good morning, my beautiful Kings and Queens.… I am not a racist. I grew up
in Villa Park, Illinois. I was the only black girl on an all-white cheerleading
squad.… Black people, you will not be successful in this world until you
learn how to work with white people. I want the white folks to really
understand out there that black people are doing as much as we can…and we
can’t help but get pissed off when we see situations where it’s clear that the
black life didn’t matter. For those of you who question why he was running
away, well goddamn, in the news that we’ve seen of late, you can stand there
and surrender to the cops and still be killed.
Three months later, she too was dead.
Talking to Strangers is an attempt to understand what really happened by the
side of the highway that day in rural Texas.
Why write a book about a traffic stop gone awry? Because the debate
spawned by that string of cases was deeply unsatisfying. One side made the
discussion about racism—looking down at the case from ten thousand feet. The
other side examined each detail of each case with a magnifying glass. What was
the police officer like? What did he do, precisely? One side saw a forest, but no
trees. The other side saw trees and no forest.
Each side was right, in its own way. Prejudice and incompetence go a long
way toward explaining social dysfunction in the United States. But what do you
do with either of those diagnoses aside from vowing, in full earnestness, to try

harder next time? There are bad cops. There are biased cops. Conservatives
prefer the former interpretation, liberals the latter. In the end the two sides
canceled each other out. Police officers still kill people in this country, but those
deaths no longer command the news. I suspect that you may have had to pause
for a moment to remember who Sandra Bland was. We put aside these
controversies after a decent interval and moved on to other things.
I don’t want to move on to other things.

3.
In the sixteenth century, there were close to seventy wars involving the nations
and states of Europe. The Danes fought the Swedes. The Poles fought the
Teutonic Knights. The Ottomans fought the Venetians. The Spanish fought the
French—and on and on. If there was a pattern to the endless conflict, it was that
battles overwhelmingly involved neighbors. You fought the person directly
across the border, who had always been directly across your border. Or you
fought someone inside your own borders: the Ottoman War of 1509 was between
two brothers. Throughout the majority of human history, encounters—hostile or
otherwise—were rarely between strangers. The people you met and fought often
believed in the same God as you, built their buildings and organized their cities
in the same way you did, fought their wars with the same weapons according to
the same rules.
But the sixteenth century’s bloodiest conflict fit none of those patterns. When
the Spanish conquistador Hernán Cortés met the Aztec ruler Montezuma II,
neither side knew anything about the other at all.
Cortés landed in Mexico in February of 1519 and slowly made his way
inland, advancing on the Aztec capital of Tenochtitlán. When Cortés and his
army arrived, they were in awe. Tenochtitlán was an extraordinary sight—far
larger and more impressive than any of the cities Cortés and his men would have
known back in Spain. It was a city on an island, linked to the mainland with
bridges and crossed by canals. It had grand boulevards, elaborate aqueducts,
thriving marketplaces, temples built in brilliant white stucco, public gardens, and
even a zoo. It was spotlessly clean—which, to someone raised in the filth of
medieval European cities, would have seemed almost miraculous.
“When we saw so many cities and villages built in the water and other great

towns on dry land, we were amazed and said that it was like the enchantments,”
one of Cortés’s officers, Bernal Díaz del Castillo, recalled. “And some of our
soldiers even asked whether the things that we saw were not a dream?… I do not
know how to describe it, seeing things as we did that had never been heard of or
seen before, not even dreamed about.”
The Spanish were greeted at the gates of Tenochtitlán by an assembly of
Aztec chiefs, then taken to Montezuma. He was a figure of almost surreal
grandeur, carried on a litter embroidered with gold and silver and festooned with
flowers and precious stones. One of his courtiers advanced before the
procession, sweeping the ground. Cortés dismounted from his horse. Montezuma
was lowered from his litter. Cortés, like the Spaniard he was, moved to embrace
the Aztec leader—only to be restrained by Montezuma’s attendants. No one
embraced Montezuma. Instead, the two men bowed to each other.
“Art thou not he? Art thou Montezuma?”
Montezuma answered: “Yes, I am he.”
No European had ever set foot in Mexico. No Aztec had ever met a European.
Cortés knew nothing about the Aztecs, except to be in awe of their wealth and
the extraordinary city they had built. Montezuma knew nothing of Cortés, except
that he had approached the Aztec kingdom with great audacity, armed with
strange weapons and large, mysterious animals—horses—that the Aztecs had
never seen before.
Is it any wonder why the meeting between Cortés and Montezuma has
fascinated historians for so many centuries? That moment—500 years ago—
when explorers began traveling across oceans and undertaking bold expeditions
in previously unknown territory, an entirely new kind of encounter emerged.
Cortés and Montezuma wanted to have a conversation, even though they knew
nothing about the other. When Cortés asked Montezuma, “Art thou he?,” he
didn’t say those words directly. Cortés spoke only Spanish. He had to bring two
translators with him. One was an Indian woman named Malinche, who had been
captured by the Spanish some months before. She knew the Aztec language
Nahuatl and Mayan, the language of the Mexican territory where Cortés had
begun his journey. Cortés also had with him a Spanish priest named Gerónimo
del Aguilar, who had been shipwrecked in the Yucatán and learned Mayan
during his sojourn there. So Cortés spoke to Aguilar in Spanish. Aguilar
translated into Mayan for Malinche. And Malinche translated the Mayan into
Nahuatl for Montezuma—and when Montezuma replied, “Yes, I am,” the long
translation chain ran in reverse. The kind of easy face-to-face interaction that

each had lived with his entire life had suddenly become hopelessly complicated.1
Cortés was taken to one of Montezuma’s palaces—a place that Aguilar
described later as having “innumerable rooms inside, antechambers, splendid
halls, mattresses of large cloaks, pillows of leather and tree fibre, good
eiderdowns, and admirable white fur robes.” After dinner, Montezuma rejoined
Cortés and his men and gave a speech. Immediately, the confusion began. The
way the Spanish interpreted Montezuma’s remarks, the Aztec king was making
an astonishing concession: he believed Cortés to be a god, the fulfillment of an
ancient prophecy that said an exiled deity would one day return from the east.
And he was, as a result, surrendering to Cortés. You can imagine Cortés’s
reaction: this magnificent city was now effectively his.
But is that really what Montezuma meant? Nahuatl, the language of the
Aztecs, had a reverential mode. A royal figure such as Montezuma would speak
in a kind of code, according to a cultural tradition in which the powerful
projected their status through an elaborate false humility. The word in Nahuatl
for a noble, the historian Matthew Restall points out, is all but identical to the
word for child. When a ruler such as Montezuma spoke of himself as small and
weak, in other words, he was actually subtly drawing attention to the fact that he
was esteemed and powerful.
“The impossibility of adequately translating such language is obvious,”
Restall writes:
The speaker was often obliged to say the opposite of what was really meant.
True meaning was embedded in the use of reverential language. Stripped of
these nuances in translation, and distorted through the use of multiple
interpreters…not only was it unlikely that a speech such as Montezuma’s
would be accurately understood, but it was probable that its meaning would
be turned upside down. In that case, Montezuma’s speech was not his
surrender; it was his acceptance of a Spanish surrender.
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 highranking 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 gobetween. 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 Germany. 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-toface.
“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?
Puzzle Number One: Why can’t we tell when the stranger in front of us is
lying to our face?
1

The CIA makes a regular practice of giving its agents lie-detector tests—to guard against just the
kind of treachery that Aspillaga was describing. Whenever one of the agency’s Cuban spies left the
island, the CIA would meet them secretly in a hotel room and have them sit for a polygraph.
Sometimes the Cubans would pass; the head of the polygraph division personally gave a clean bill of
health to six Cuban agents who ended up being doubles. Other times, the Cubans would fail. But
what happened when they did? The people running the Cuban section dismissed it. One of the CIA’s
former polygraphers, John Sullivan, remembers being summoned to a meeting after his group gave
the thumbs-down on a few too many Cuban assets. “They ambushed us,” Sullivan said. “We were
berated unmercifully.…All these case officers were saying, ‘You guys just don’t know what you’re
doing,’ et cetera, et cetera. ‘Mother Teresa couldn’t pass you.’ I mean, they were really very, very
nasty about it.”
But can you blame them? The case officers chose to replace one method of making sense of strangers
(strapping them to a polygraph machine) with another: their own judgment. And that is perfectly
logical.
Polygraphy is, to say the least, an inexact art. The case officer would have had years of experience with the
agent: met them, talked to them, analyzed the quality of the reports they filed. The assessment of a
trained professional, made over the course of many years, ought to be more accurate than the results
of a hurried meeting in a hotel room, right? Except that it wasn’t.
“Many of our case officers think, ‘I’m such a good case officer, they can’t fool me,’” Sullivan said. “This
one guy I’m thinking of in particular—and he was a very, very good case officer—they thought he
was one of the best case officers in the agency.” He was clearly talking about the Mountain Climber.
“They took him to the cleaners. They actually got him on film servicing a dead drop. It was crazy.”

CHAPTER TWO

Getting to Know der Führer

1.
On the evening of August 28, 1938, Neville Chamberlain called his closest
advisor to 10 Downing Street for a late-night strategy session. Chamberlain had
been the British prime minister a little over a year. He was a former
businessman, a practical and plainspoken man, whose interests and experience
lay with domestic affairs. But now he faced his first foreign-policy crisis. It
involved Adolf Hitler, who had been making increasingly bellicose statements
about invading the Sudetenland, the German-speaking portion of
Czechoslovakia.
If Germany invaded Czechoslovakia, it would almost certainly mean a world
war, which Chamberlain wanted desperately to avoid. But Hitler had been
particularly reclusive in recent months, and Germany’s intentions were so
opaque that the rest of Europe was growing nervous. Chamberlain was
determined to resolve the impasse. He dubbed his idea, which he put to his
advisors that night, Plan Z. It was top secret. Chamberlain would later write that

the idea was “so unconventional and daring that it rather took [Foreign Secretary
Lord] Halifax’s breath away.” Chamberlain wanted to fly to Germany and
demand to meet Hitler face-to-face.
One of the odd things about the desperate hours of the late 1930s, as Hitler
dragged the world toward war, was how few of the world’s leaders really knew
the German leader.1 Hitler was a mystery. Franklin Roosevelt, the American
president throughout Hitler’s rise, never met him. Nor did Joseph Stalin, the
Soviet leader. Winston Churchill, Chamberlain’s successor, came close while
researching a book in Munich in 1932. He and Hitler twice made plans to meet
for tea, but on both occasions Hitler stood him up.
The only people in England who spent any real amount of time with Hitler
before the war were British aristocrats friendly to the Nazi cause, who would
sometimes cross the Channel to pay their respects or join the Führer at parties.
(“In certain moods he could be very funny,” the fascist socialite Diana Mitford
wrote in her memoirs. She dined with him frequently in Munich. “He did
imitations of marvelous drollery.”) But those were social calls. Chamberlain was
trying to avert world war, and it seemed to him that he would benefit from taking
the measure of Hitler for himself. Was Hitler someone who could be reasoned
with? Trusted? Chamberlain wanted to find out.
On the morning of September 14, the British ambassador to Germany sent a
telegram to Hitler’s foreign minister, Joachim von Ribbentrop. Would Hitler like
to meet? Von Ribbentrop replied the same day: yes. Chamberlain was a masterly
politician with a gift for showmanship, and he artfully let the news slip. He was
going to Germany to see if he could avert war. Across Britain, there was a shout
of celebration. Polls showed that 70 percent of the country thought his trip was a
“good thing for peace.” The newspapers backed him. In Berlin, one foreign
correspondent reported that he had been eating in a restaurant when the news
broke, and the room had risen, as one, to toast Chamberlain’s health.
Chamberlain left London on the morning of September 15. He’d never flown
before, but he remained calm even as the plane flew into heavy weather near
Munich. Thousands had gathered at the airport to greet him. He was driven to
the train station in a cavalcade of fourteen Mercedes, then had lunch in Hitler’s
own dining car as the train made its way into the mountains, toward Hitler’s
retreat at Berchtesgaden. He arrived at five in the evening. Hitler came and
shook his hand. Chamberlain would later report every detail of his first
impressions in a letter to his sister Ida:

Halfway down the steps stood the Führer bareheaded and dressed in a khakicoloured coat of broadcloth with a red armlet and a swastika on it and the
military cross on his breast. He wore black trousers such as we wear in the
evening and black patent leather lace-up shoes. His hair is brown, not black,
his eyes blue, his expression rather disagreeable, especially in repose and
altogether he looks entirely undistinguished. You would never notice him in a
crowd and would take him for the house painter he was.
Hitler ushered Chamberlain upstairs to his study, with just an interpreter in
tow. They talked, sometimes heatedly. “I am ready to face a world war!” Hitler
exclaimed to Chamberlain at one point. Hitler made it plain that he was going to
seize the Sudetenland, regardless of what the world thought. Chamberlain
wanted to know whether that was all Hitler wanted. Hitler said it was.
Chamberlain looked at Hitler long and hard and decided he believed him. In the
same letter to his sister, Chamberlain wrote that he had heard back from people
close to Hitler that the German leader felt he had had a conversation “with a
man.” Chamberlain went on:
“In short I had established a certain confidence which was my aim, and on my
side in spite of the hardness and ruthlessness I thought I saw in his face I got the
impression that here was a man who could be relied upon when he had given his
word.”
Chamberlain flew back to England the next morning. At Heston Airport, he
gave a quick speech on the tarmac. “Yesterday afternoon I had a long talk with
Herr Hitler,” he said. “I feel satisfied now that each of us fully understands what
is in the mind of the other.” The two of them would meet again, he promised,
only this time closer to England. “That is to spare an old man such another long
journey,” Chamberlain said, to what those present remembered as “laughter and
cheers.”

2.
Chamberlain’s negotiations with Hitler are widely regarded as one of the great
follies of the Second World War. Chamberlain fell under Hitler’s spell. He was
outmaneuvered at the bargaining table. He misread Hitler’s intentions, and failed
to warn Hitler that if he reneged on his promises there would be serious

consequences. History has not been kind to Neville Chamberlain.
But underneath those criticisms is a puzzle. Chamberlain flew back to
Germany two more times. He sat with Hitler for hours. The two men talked,
argued, ate together, walked around together. Chamberlain was the only Allied
leader of that period to spend any significant time with Hitler. He made careful
note of the man’s behavior. “Hitler’s appearance and manner when I saw him
appeared to show that the storm signals were up,” Chamberlain told his sister
Hilda after another of his visits to Germany. But then “he gave me the double
handshake that he reserves for specially friendly demonstrations.” Back in
London, he told his cabinet that he had seen in the Führer “no signs of insanity
but many of excitement.” Hitler wasn’t crazy. He was rational, determined: “He
had thought out what he wanted and he meant to get it and he would not brook
opposition beyond a certain point.”
Chamberlain was acting on the same assumption that we all follow in our
efforts to make sense of strangers. We believe that the information gathered from
a personal interaction is uniquely valuable. You would never hire a babysitter for
your children without meeting that person first. Companies don’t hire employees
blind. They call them in and interview them closely, sometimes for hours at a
stretch, on more than one occasion. They do what Chamberlain did: they look
people in the eye, observe their demeanor and behavior, and draw conclusions.
He gave me the double handshake. Yet all that extra information Chamberlain
gathered from his personal interactions with Hitler didn’t help him see Hitler
more clearly. It did the opposite.
Is this because Chamberlain was naive? Perhaps. His experience in foreign
affairs was minimal. One of his critics would later compare him to a priest
entering a pub for the first time, blind to the difference “between a social
gathering and a rough house.”
But this pattern isn’t confined to Chamberlain. It also afflicted Lord Halifax,
who would go on to become Chamberlain’s foreign secretary. Halifax was an
aristocrat, a superb student at Eton and Oxford. He served as Viceroy of India
between the wars, where he negotiated brilliantly with Mahatma Gandhi. He was
everything Chamberlain was not: worldly, seasoned, deeply charming, an
intellectual—a man of such resolute religiosity that Churchill dubbed him the
“Holy Fox.”
Halifax went to Berlin in the fall of 1937 and met with the German leader at
Berchtesgaden: he was the only other member of England’s ruling circle to have
spent time with the Führer. Their meeting wasn’t some meaningless diplomatic

reception. It began with Halifax mistaking Hitler for a footman and almost
handing him his coat. And then Hitler was Hitler for five hours: sulking,
shouting, digressing, denouncing. He talked about how much he hated the press.
He talked about the evils of communism. Halifax listened to the performance
with what another British diplomat at the time called a “mixture of astonishment,
repugnance, and compassion.”
Halifax spent five days in Germany. He met with two of Hitler’s top ministers
—Hermann Göring and Joseph Goebbels. He attended a dinner at the British
Embassy, where he met a host of senior German politicians and businessmen.
When he returned home, Halifax said that it was “all to the good making
contact” with the German leadership, which is hard to dispute. That’s what a
diplomat is supposed to do. He had gained valuable insights from their face-toface encounter about Hitler’s bullying and volatility. But what was Halifax’s
ultimate conclusion? That Hitler didn’t want to go to war, and was open to
negotiating a peace. No one ever thought Halifax was naive, yet he was as
deluded after meeting with Hitler as Chamberlain was.
The British diplomat who spent the most time with Hitler was the ambassador
to Germany, Nevile Henderson. He met Hitler repeatedly, went to his rallies.
Hitler even had a nickname for Henderson, “The man with the carnation,”
because of the flower the dapper Henderson always wore in his lapel. After
attending the infamous Nuremberg Rally in early September 1938, Henderson
wrote in his dispatch to London that Hitler seemed so abnormal that “he may
have crossed the borderline into insanity.” Henderson wasn’t in Hitler’s thrall.
But did he think Hitler had dishonorable intentions toward Czechoslovakia? No.
Hitler, he believed, “hates war as much as anyone.” Henderson, too, read Hitler
all wrong.2
The blindness of Chamberlain and Halifax and Henderson is not at all like
Puzzle Number One, from the previous chapter. That was about the inability of
otherwise intelligent and dedicated people to understand when they are being
deceived. This is a situation where some people were deceived by Hitler and
others were not. And the puzzle is that the group who were deceived are the ones
you’d expect not to be, while those who saw the truth are the ones you’d think
would be deceived.
Winston Churchill, for example, never believed for a moment that Hitler was
anything more than a duplicitous thug. Churchill called Chamberlain’s visit “the
stupidest thing that has ever been done.” But Hitler was someone he’d only ever
read about. Duff Cooper, one of Chamberlain’s cabinet ministers, was equally

clear-eyed. He listened with horror to Chamberlain’s account of his meeting with
Hitler. Later, he would resign from Chamberlain’s government in protest. Did
Cooper know Hitler? No. Only one person in the upper reaches of the British
diplomatic service—Anthony Eden, who preceded Halifax as foreign secretary
—had both met Hitler and saw the truth of him. But for everyone else? The
people who were right about Hitler were those who knew the least about him
personally. The people who were wrong about Hitler were the ones who had
talked with him for hours.
This could all be a coincidence, of course. Perhaps Chamberlain and his
cohort, for whatever private reason, were determined to see the Hitler they
wanted to see, regardless of the evidence of their eyes and ears. Except that the
same puzzling pattern crops up everywhere.

3.
The judge was middle-aged, tall, white-haired, with an accent that put his roots
squarely in the borough of Brooklyn. Let’s call him Solomon. He had served on
the bench in New York State for over a decade. He wasn’t imperious or
intimidating. He was thoughtful, with a surprisingly gentle manner.
This was a Thursday, which in his courtroom was typically a busy day for
arraignments. The defendants were all people who had been arrested in the past
twenty-four hours on suspicion of some kind of crime. They’d just spent a
sleepless night in a holding cell and now they were being brought into the
courtroom in handcuffs, one by one. They sat on a low bench behind a partition,
just to Solomon’s left. When each case was called, the clerk would hand
Solomon a file containing the defendant’s rap sheet, and he would start flipping
through, bringing himself up to speed. The defendant would stand directly in
front of Solomon, with his lawyer on one side and the district attorney on the
other. The two lawyers would talk. Solomon would listen. Then he would decide
if the defendant would be required to post bail, and if so, how much the bail
should be. Does this perfect stranger deserve his freedom?
The hardest cases, he said later, involved kids. A sixteen-year-old would
come in charged with some horrible crime. And he would know that if he set bail
high enough, the child would end up in a “cage” in the city’s notorious Rikers
Island facility, where—he put it as delicately as he could—there’s basically “a

riot waiting to happen at every turn.”3 Those cases got even harder when he
looked up into the courtroom and saw the kid’s mom sitting in the gallery. “I
have a case like this every day,” he said. He had taken up meditation. He found
that made things easier.
Solomon was faced day in, day out with a version of the same problem that
had faced Neville Chamberlain and the British diplomatic service in the fall of
1938: he was asked to assess the character of a stranger. And the criminal justice
system assumes, as Chamberlain did, that those kinds of difficult decisions are
better made when the judge and the judged meet each other first.
Later that afternoon, for example, Solomon was confronted with an older man
with thinning, close-cropped hair. He was wearing blue jeans and a guayabera
shirt and spoke only Spanish. He’d been arrested because of an “incident”
involving the six-year-old grandson of his girlfriend. The boy told his father
right away. The district attorney asked for $100,000 bail. There was no way the
man had the resources to raise that amount. If Solomon agreed with the DA, the
man in the guayabera would go straight to jail.
On the other hand, the man denied everything. He had two previous criminal
offenses—but they were misdemeanors, from many years ago. He had a job as a
mechanic, which he would lose if he went to jail, and he had an ex-wife and a
fifteen-year-old son whom he was supporting with that income. So Solomon had
to think about that fifteen-year-old, relying on his father’s paycheck. He also
surely knew that six-year-olds are not the most reliable of witnesses. So there
was no way for Solomon to be sure whether this would all turn out to be a
massive misunderstanding or part of some sinister pattern. In other words, the
decision about whether to let the man in the guayabera go free—or to hold him
in jail until trial—was impossibly difficult. And to help him make the right call,
Solomon did what all of us would do in that situation: he looked the man right in
the eyes and tried to get a sense of who he really was. So did that help? Or are
judges subject to the same puzzle as Neville Chamberlain?

4.
The best answer we have to that question comes from a study conducted by a
Harvard economist, three elite computer scientists, and a bail expert from the
University of Chicago. The group—and for simplicity’s sake, I’ll refer to it by

the economist’s name, Sendhil Mullainathan—decided to use New York City as
their testing ground. They gathered up the records of 554,689 defendants
brought before arraignment hearings in New York from 2008 to 2013—554,689
defendants in all. Of those, they found that the human judges of New York
released just over 400,000.
Mullainathan then built an artificial intelligence system, fed it the same
information the prosecutors had given judges in those arraignment cases (the
defendant’s age and criminal record), and told the computer to go through those
554,689 cases and make its own list of 400,000 people to release. It was a bakeoff: man versus machine. Who made the best decisions? Whose list committed
the fewest crimes while out on bail and was most likely to show up for their trial
date? The results weren’t even close. The people on the computer’s list were 25
percent less likely to commit a crime while awaiting trial than the 400,000
people released by the judges of New York City. 25 percent! In the bake-off,
machine destroyed man.4
To give you just one sense of the mastery of Mullainathan’s machine, it
flagged 1 percent of all the defendants as “high risk.” These are the people the
computer thought should never be released prior to trial. According to the
machine’s calculations, well over half of the people in that high-risk group
would commit another crime if let out on bail. When the human judges looked at
that same group of bad apples, though, they didn’t identify them as dangerous at
all. They released 48.5 percent of them! “Many of the defendants flagged by the
algorithm as high risk are treated by the judge as if they were low risk,” Team
Mullainathan concluded in a particularly devastating passage. “Performing this
exercise suggests that judges are not simply setting a high threshold for detention
but are mis-ranking defendants.…The marginal defendants they select to detain
are drawn from throughout the entire predicted risk distribution.” Translation:
the bail decisions of judges are all over the place.
I think you’ll agree that this is baffling. When judges make their bail
decisions, they have access to three sources of information. They have the
defendant’s record—his age, previous offenses, what happened the last time he
was granted bail, where he lives, where he works. They have the testimony of
the district attorney and the defendant’s lawyer: whatever information is
communicated in the courtroom. And they have the evidence of their own eyes.
What is my feeling about this man before me?
Mullainathan’s computer, on the other hand, couldn’t see the defendant and it
couldn’t hear anything that was said in the courtroom. All it had was the

defendant’s age and rap sheet. It had a fraction of the information available to
the judge—and it did a much better job at making bail decisions.
In my second book, Blink, I told the story of how orchestras made much
smarter recruiting decisions once they had prospective hires audition behind a
screen. Taking information away from the hiring committee made for better
judgments. But that was because the information gleaned from watching
someone play is largely irrelevant. If you’re judging whether someone is a good
violin player, knowing whether that person is big or small, handsome or homely,
white or black isn’t going to help. In fact, it will probably only introduce biases
that will make your job even harder.
But when it comes to a bail decision, the extra information the judge has
sounds like it should be really useful. In an earlier case in Solomon’s courtroom,
a young man in basketball shorts and a gray T-shirt was charged with getting into
a fight with someone, then buying a car with the man’s stolen credit card. In
asking for bail, the district attorney pointed out that he had failed to appear for
his court date after two previous arrests. That’s a serious red flag. But not all
“FTAs” are identical. What if the defendant was given the wrong date? What if
he would lose his job if he took off work that day, and decided it wasn’t worth it?
What if his child was in the hospital? That’s what the defendant’s lawyer told the
judge: Her client had a good excuse. The computer didn’t know that, but the
judge did. How could that not help?
In a similar vein, Solomon said the thing he’s most alert to in bail cases is
“mental illness with an allegation of violence.” Those kinds of cases are a
judge’s worst nightmare. They let someone out on bail, then that person stops
taking their medication and goes on to commit some horrible crime. “It’s shoot a
cop,” Solomon said.
It’s drive a car into a minivan, killing a pregnant woman and her husband. It’s
hurt a child. [It’s] shoving somebody in front of a subway train and killing
them. It’s an awful situation at every possible angle.…No judge would ever
want to be the one having made the release decision on that case.
Some of the clues to that kind of situation are in the defendant’s file: medical
records, previous hospitalizations, some mention of the defendant’s being found
not competent. But other clues are found only in the moment.
“You also will hear terms thrown around in the courtroom of ‘EDP’—
emotionally disturbed person,” Solomon said.

That will come from either the police department who’s brought them in and
handed you an envelope that’s from a doctor at a hospital where he’s been
screened at a psychiatric ER prior to arraignment.…Other times, that
information will get into the DA’s folder and the DA will ask questions.…
That’s a fact for me to think about.
He’ll look at the defendant, in those cases—closely, carefully, searching for,
as he put it,
sort of a glassy-eyed look, not being able to make eye contact. And not the
adolescent unable to make eye contact because the frontal lobe hasn’t
developed. I’m talking about the adult off their meds.…
Mullainathan’s machine can’t overhear the prosecutor talking about an EDP,
and it can’t see that telltale glassy-eyed look. That fact should translate into a big
advantage for Solomon and his fellow judges. But for some reason it doesn’t.
Puzzle Number Two: How is it that meeting a stranger can sometimes make
us worse at making sense of that person than not meeting them?

5.
Neville Chamberlain made his third and final visit to Germany at the end of
September 1938, two weeks after his first visit. The meeting was in Munich at
the Nazi Party’s offices—the Führerbau. Italian leader Benito Mussolini and
French prime minister Édouard Daladier were also invited. The four of them
met, with their aides, in Hitler’s private study. On the morning of the second day,
Chamberlain asked Hitler if the two of them could meet alone. By this point,
Chamberlain felt he had the measure of his adversary.
When Hitler had said his ambitions were limited to Czechoslovakia,
Chamberlain believed that “Herr Hitler was telling the truth.” It was now just a
matter of getting that commitment in writing.
Hitler took him to his apartment on Prinzregentenplatz. Chamberlain pulled
out a piece of paper on which he had written a simple agreement and asked
Hitler whether he would sign it. As the interpreter translated the words into
German, “Hitler frequently ejaculated, ‘Ja! Ja!’ And at the end he said, ‘Yes I

will certainly sign it,’” Chamberlain later wrote to one of his sisters. “‘When
shall we do it?’ I said, ‘now,’ & we went at once to the writing table & put our
signatures to the two copies which I had brought with me.”
That afternoon, Chamberlain flew home to a hero’s welcome. A crowd of
journalists surged toward him. He took the letter from his breast pocket and
waved it to the crowd. “This morning I had another talk with the German
Chancellor Herr Hitler, and here is a paper which bears his name upon it as well
as mine.”
Then it was back to the prime minister’s residence at 10 Downing Street.
“My good friends, this is the second time in our history that there has come
back from Germany to Downing Street peace with honor. I believe it is peace for
our time. We thank you from the bottom of our hearts.”
The crowd cheered.
“Now I recommend you go home, and sleep quietly in your beds.”
In March 1939, Hitler invaded the rest of Czechoslovakia. It had taken him
less than six months to break his agreement with Chamberlain. On September 1,
1939, Hitler invaded Poland, and the world was at war.
We have, in other words, CIA officers who cannot make sense of their spies,
judges who cannot make sense of their defendants, and prime ministers who
cannot make sense of their adversaries. We have people struggling with their
first impressions of a stranger. We have people struggling when they have
months to understand a stranger. We have people struggling when they meet with
someone only once, and people struggling when they return to the stranger again
and again. They struggle with assessing a stranger’s honesty. They struggle with
a stranger’s character. They struggle with a stranger’s intent.
It’s a mess.

6.
One last thing:
Take a look at the following word, and fill in the two blank letters. Do it
quickly, without thinking.
GL__

This is called a word-completion task. Psychologists commonly use it to test
things such as memory.
I completed G L _ _ as GLUM. Remember that. The next word is:
_ _TER
I completed that as HATER. Remember that too. Here are the rest of the words:
S_ _RE
P_ _ N
TOU_ _
ATT_ _ _
BO_ _
FL_ _ T
SL_ T
STR_ _ _
GO_ _
CHE_ _
_ _OR
SL_ _ _
SC _ _ _
_ _ NNER
B_ _ T
PO _ _ _
BA_ _
_RA_
_ _ _EAT
I started out with GLUM and HATER and ended up with SCARE, ATTACK,
BORE, FLOUT, SLIT, CHEAT, TRAP, and DEFEAT. That’s a pretty morbid and
melancholy list. But I don’t think that says anything about the darkness of my
soul. I’m not melancholy. I’m an optimist. I think that the first word, GLUM,
popped into my head, and then I just continued in that vein.
A few years ago, a team of psychologists led by Emily Pronin gave a group of
people that same exercise. Pronin had them fill in the blank spaces. Then she
asked them the same question: What do you think your choices say about you?
For instance, if you completed TOU_ _ as TOUCH, does that suggest that you

are a different kind of person than if you completed it as TOUGH? The
respondents took the same position I did. They’re just words.
“I don’t agree with these word-stem completions as a measure of my
personality,” one of Pronin’s subjects wrote. And the others in the group agreed:
“These word completions don’t seem to reveal much about me at all.…
Random completions.”
“Some of the words I wrote seem to be the antithesis of how I view the
world. For instance, I hope that I am not always concerned about being
STRONG, the BEST, or a WINNER.”
“I don’t really think that my word completions reveal that much about me.
… Occurred as a result of happenstance.”
“Not a whole lot.… They reveal vocabulary.”
“I really don’t think there was any relationship.… The words are just
random.”
“The words PAIN, ATTACK, and THREAT seem similar, but I don’t know
that they say anything about me.”
But then things got interesting. Pronin gave the group other people’s words.
These were perfect strangers. She asked the same question. What do you think
this stranger’s choices reveal? And this time Pronin’s panel completely changed
their minds.
“He doesn’t seem to read too much, since the natural (to me) completion of
B_ _K would be BOOK. BEAK seems rather random, and might indicate
deliberate unfocus of mind.”
“I get the feeling that whoever did this is pretty vain, but basically a nice
guy.”
Keep in mind that these are the exact same people who just moments before
had denied that the exercise had any meaning at all.
“The person seems goal-oriented and thinks about competitive settings.”
“I have a feeling that the individual in question may be tired very often in
his or her life. In addition, I think that he or she might be interested in having
close personal interactions with someone of the opposite sex. The person may
also enjoy playing games.”

The same person who said, “These word completions don’t seem to reveal
much about me at all” turned around and said, of a perfect stranger:
“I think this girl is on her period.…I also think that she either feels she or
someone else is in a dishonest sexual relationship, according to the words
WHORE, SLOT (similar to slut), CHEAT.”
The answers go on and on like this. And no one seemed even remotely aware
that they had been trapped in a contradiction.
“I guess there is some relationship.…He talks a lot about money and the
BANK. A lot more correlation here.”
“He seems to focus on competition and winning. This person could be an
athlete or someone who is very competitive.”
“It seems this individual has a generally positive outlook toward the things
he endeavors. Most words, such as WINNER, SCORE, GOAL, indicate some
sort of competitiveness, which combined with the jargon, indicate that he has
some athletic competitive nature.”
If the panel had seen my GLUM, HATER, SCARE, ATTACK, BORE,
FLOUT, SLIT, CHEAT, TRAP, and DEFEAT, they would have worried for my
soul.
Pronin calls this phenomenon the “illusion of asymmetric insight.” She
writes:
The conviction that we know others better than they know us—and that we
may have insights about them they lack (but not vice versa)—leads us to talk
when we would do well to listen and to be less patient than we ought to be
when others express the conviction that they are the ones who are being
misunderstood or judged unfairly.
This is the problem at the heart of those first two puzzles. The officers on the
Cuba desk of the CIA were sure they could evaluate the loyalty of their spies.
Judges don’t throw up their hands at the prospect of assessing the character of
defendants. They give themselves a minute or two, then authoritatively pass
judgment. Neville Chamberlain never questioned the wisdom of his bold plan to
avert war. If Hitler’s intentions were unclear, it was his job, as prime minister, to

go to Germany and figure them out.
We think we can easily see into the hearts of others based on the flimsiest of
clues. We jump at the chance to judge strangers. We would never do that to
ourselves, of course. We are nuanced and complex and enigmatic. But the
stranger is easy.
If I can convince you of one thing in this book, let it be this: Strangers are not
easy.
1

The one exception was Canadian prime minister William Lyon Mackenzie King. He met Hitler in
1937. He loved him. He compared him to Joan of Arc.
2 The Nazi official Henderson knew even better was Göring, Hitler’s deputy. Henderson would go
stag hunting with Göring. They had long conversations. Henderson was convinced that Göring
wanted peace as well, and that underneath his Nazi bluster was a decent man. In a memoir of his time
in Berlin, written just as war broke out, Henderson said that Göring “loved animals and children; and,
before ever he had one of his own, the top floor at Karinhall contained a vast playroom fitted up with
every mechanical toy dear to the heart of a modern child. Nothing used to give him greater pleasure
than to go and play there with them. The toys might, it is true, include models of airplanes dropping
heavy bombs which exploded on defenseless towns or villages; but, as he observed when I
reproached him on the subject, it was not part of the Nazi conception of life to be excessively
civilized or to teach squeamishness to the young.” (In case you were wondering, that’s what Nazism
was really about: tough-minded child-rearing.)
3

The law has since been changed. A defendant must be eighteen years old or above to be sent to
Rikers.
4 Two technical points about the dueling lists of 400,000 defendants: When Mullainathan says that
the computer’s list committed 25 percent fewer crimes than the judge’s list, he’s counting failure to
appear for a trial date as a crime. Second, I’m sure you are wondering how Mullainathan could
calculate, with such certainty, who would or wouldn’t end up committing a crime while out on
pretrial release. It’s not because he has a crystal ball. It’s an estimate made on the basis of a highly
sophisticated statistical analysis. Here’s the short version. Judges in New York City take turns doing
bail hearings. Defendants are, essentially, randomly assigned to them for consideration. Judges in
New York (as in all jurisdictions) vary dramatically in how likely they are to release someone, or how
prohibitively high they set bail. Some judges are very permissive. Others are strict. So imagine that
one set of strict judges sees 1,000 defendants and releases 25 percent of them. Another set of
permissive judges sees 1,000 defendants, who are in every way equivalent to the other 1,000, and
releases 75 percent of them. By comparing the crime rates of the released defendants in each group,
you can get a sense of how many harmless people the strict judges jailed, and how many dangerous
people the permissive judges set free. That estimate, in turn, can be applied to the machine’s
predictions. When it passes judgment on its own 1,000 defendants, how much better is it than the
strict judges on the one hand, and the permissive judges on the other? This sounds highly
complicated, and it is. But it’s a well-established methodology. For a more complete explanation, I
encourage you to read Mullainathan’s paper.

Part Two
Default to Truth

CHAPTER THREE

The Queen of Cuba

1.
Let’s take a look at another Cuban spy story.
In the early 1990s, thousands of Cubans began to flee the regime of Fidel
Castro. They cobbled together crude boats—made of inner tubes and metal
drums and wooden doors and any number of other stray parts—and set out on a
desperate voyage across the ninety miles of the Florida Straits to the United
States. By one estimate, as many as 24,000 people died attempting the journey. It
was a human-rights disaster. In response, a group of Cuban emigrés in Miami
founded Hermanos al Rescate—Brothers to the Rescue. They put together a
makeshift air force of single-engine Cessna Skymasters and took to the skies
over the Florida Straits, searching for refugees from the air and radioing their
coordinates to the Coast Guard. Hermanos al Rescate saved thousands of lives.
They became heroes.
As time passed, the emigrés grew more ambitious. They began flying into
Cuban airspace, dropping leaflets on Havana urging the Cuban people to rise up

against Castro’s regime. The Cuban government, already embarrassed by the
flight of refugees, was outraged. Tensions rose, coming to a head on February
24, 1996. That afternoon three Hermanos al Rescate planes took off for the
Florida Straits. As they neared the Cuban coastline, two Cuban Air Force MiG
fighter jets shot two of the planes out of the sky, killing all four people aboard.
The response to the attack was immediate. The United Nations Security
Council passed a resolution denouncing the Cuban government. A grave
President Clinton held a press conference. The Cuban emigré population in
Miami was furious. The two planes had been shot down in international airspace,
making the incident tantamount to an act of war. The radio chatter among the
Cuban pilots was released to the press:
“We hit him, cojones, we hit him.”
“We retired them, cojones.”
“We hit them.”
“Fuckers.”
“Mark the place where we retired them.”
“This one won’t fuck with us anymore.”
And then, after one of the MiGs zeroed in on the second Cessna:
“Homeland or death, you bastards.”
But in the midst of the controversy, the story suddenly shifted. A retired U.S.
rear admiral named Eugene Carroll gave an interview to CNN. Carroll was an
influential figure inside Washington. He had formerly served as the director of
all U.S. armed forces in Europe, with 7,000 weapons at his disposal. Just before
the Hermanos al Rescate shoot-down, Carroll said, he and a small group of
military analysts had met with top Cuban officials.
CNN: Admiral, can you tell me what happened on your trip to Cuba, who
you spoke with and what you were told?
Carroll: We were hosted by the Ministry of Defense. General Rosales del
Toro.… We traveled around, inspected Cuban bases, Cuban schools, their
partially completed nuclear power plant, and so on. In long discussions
with General Rosales del Toro and his staff the question came up about
these overflights from U.S. aircraft—not government aircraft, but private
airplanes operating out of Miami. They asked us, “What would happen if
we shot one of these down? We can, you know.”

Carroll interpreted that question from his Cuban hosts as a thinly veiled
warning. The interview continued:
CNN: So when you returned, who did you relay this information to?
Carroll: As soon as we could make appointments, we discussed the
situation…with members of the State Department and members of the
Defense Intelligence Agency.
The Defense Intelligence Agency—the DIA—is the third arm of the foreign
intelligence triumvirate in the U.S. government, along with the CIA and the
National Security Agency. If Carroll had met with the State Department and the
DIA, he had delivered the Cuban warning about as high up in the American
government as you could go. And did the State Department and DIA take those
warnings to heart? Did they step in and stop Hermanos al Rescate from
continuing their reckless forays into Cuban airspace? Obviously not.1
Carroll’s comments ricocheted around Washington, DC, policy circles. This
was an embarrassing revelation. The Cuban shoot-down happened on February
24. Carroll’s warnings to the State Department and DIA were delivered on
February 23. A prominent Washington insider met with U.S. officials the day
before the crisis, explicitly warned them that the Cubans had lost patience with
Hermanos al Rescate, and his warning was ignored. What began as a Cuban
atrocity was now transformed into a story about American diplomatic
incompetence.
CNN: But what about the position that these were unarmed civilian planes?
Carroll repeated what he had been told in Havana.
Carroll: That is a very sensitive question. Where were they? What were they
doing? I’ll give you an analogy. Suppose we had the planes flying over
San Diego from Mexico, dropping leaflets and inciting against [California]
Governor Wilson. How long would we tolerate these overflights after we
had warned them against it?
Fidel Castro wasn’t being invited onto CNN to defend himself. But he didn’t
need to be. He had a rear admiral making his case.

2.
The next three chapters of Talking to Strangers are devoted to the ideas of a
psychologist named Tim Levine, who has thought as much about the problem of
why we are deceived by strangers as anyone in social science. The second
chapter looks at Levine’s theories through the story of Bernie Madoff, the
investor who ran the largest Ponzi scheme in history. The third examines the
strange case of Jerry Sandusky, the Pennsylvania State University football coach
convicted of sexual abuse. And this, the first, is about the fallout from that
moment of crisis between the United States and Cuba in 1996.
Does anything about Admiral Carroll and the Cuban shoot-downs strike you
as odd? There are an awful lot of coincidences here.
1. The Cubans plan a deliberate murderous attack on U.S. citizens flying in
international airspace.
2. It just so happens that the day before the attack, a prominent military insider
delivers a stern warning to U.S. officials about the possibility of exactly that
action.
3. And, fortuitously, that warning puts that same official, the day after the
attack, in a position to make the Cuban case on one of the world’s most
respected news networks.
The timing of those three events is a little too perfect, isn’t it? If you were a
public relations firm, trying to mute the fallout from a very controversial action,
that’s exactly how you’d script it. Have a seemingly neutral expert available—
right away—to say, “I warned them!”
This is what a military counterintelligence analyst named Reg Brown thought
in the days after the incident. Brown worked on the Latin American desk of the
Defense Intelligence Agency. His job was to understand the ways in which the
Cuban intelligence services were trying to influence American military
operations. His business, in other words, was to be alert to the kinds of nuances,
subtleties, and unexplained coincidences that the rest of us ignore, and Brown
couldn’t shake the feeling that somehow the Cubans had orchestrated the whole
crisis.
It turned out, for example, that the Cubans had a source inside Hermanos al
Rescate—a pilot named Juan Pablo Roque. On the day before the attack, he had

disappeared and resurfaced at Castro’s side in Havana. Clearly Roque told his
bosses back home that Hermanos al Rescate had something planned for the 24th.
That made it difficult for Brown to imagine that the date of the Carroll briefing
had been chosen by chance. For maximum public relations impact, the Cubans
would want their warning delivered the day before, wouldn’t they? That way the
State Department and the DIA couldn’t wiggle out of the problem by saying that
the warning was vague, or long ago. Carroll’s words were right in front of them
on the day the pilots took off from Miami.
So who arranged that meeting? Brown wondered. Who picked February 23?
He did some digging, and the name he came up with startled him. It was a
colleague of his at the DIA, a Cuban expert named Ana Belen Montes. 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.”
Weeks passed. Brown agonized. To accuse a colleague of treachery on the
basis of such semi-paranoid speculation was an awfully big step, especially
when the colleague was someone of Montes’s stature. Finally Brown made up
his mind, taking his suspicions to a DIA counterintelligence officer named Scott
Carmichael.
“He came over and we walked in the neighborhood for a while during lunch
hour,” Carmichael remembers of his first meeting with Reg Brown. “And he
hardly even got to Montes. I mean most of it was listening to him saying, ‘Oh
God.’ He was wringing his hands, saying, ‘I don’t want to do the wrong thing.’”
Slowly, Carmichael drew him out. Everyone who worked on Cuba
remembered the bombshell dropped by Florentino Aspillaga. The Cubans were
good. And Brown had evidence of his own. He’d written a report in the late
1980s detailing the involvement of senior Cuban officials in international drug
smuggling. “He identified specific senior Cuban officers who were directly
involved,” Carmichael said, “and then provided the specifics. I mean, flights, the
dates, times, the places, who did what to whom, the whole enchilada.” Then a
few days before Brown’s report was released, the Cubans rounded up everyone
he’d mentioned in his investigation, executed a number of them, and issued a
public denial. “And Reg went, ‘What the fuck?’ There was a leak.”

It made Brown paranoid. In 1994, two Cuban intelligence officers had
defected and told a similar story: The Cubans had someone high inside
American intelligence. So what was he to think? Brown said to Carmichael.
Didn’t he have reason to be suspicious?
Then he told Carmichael the other thing that had happened during the
Hermanos al Rescate crisis. Montes worked at the DIA’s office on Bolling Air
Force Base, in the Anacostia section of Washington, DC. When the planes were
shot down, she was called in to the Pentagon: if you were one of the
government’s leading Cuba experts, you were needed at the scene. The shootdown happened on a Saturday. The following evening Brown happened to
telephone, asking for Montes.
“He said some woman answered the phone and told him that Ana had left,”
Carmichael says. Earlier in the day, Montes had gotten a phone call—and
afterward she’d been agitated. Then she’d told everyone in the situation room
that she was tired, that there was nothing going on, that she was going home.
Reg was just absolutely incredulous. This was just so counter to our culture
that he couldn’t even believe it. Everybody understands that when a crisis
occurs, you’re called in because you have some expertise that can add to the
decision-making processes. And at the Pentagon, you were available until you
were dismissed. It’s just understood. If somebody at that level calls you in,
because all of a sudden those North Koreans have launched a missile at San
Francisco, you don’t just decide to leave when you get tired and hungry.
Everybody understands that. And yet she did that. And Reg was just, “What
the hell?”
In Brown’s thinking, if she really worked for the Cubans, they would have
been desperate to hear from her: they would want to know what was happening
in the situation room. Did she have a meeting that night with her handler? It was
all a bit far-fetched, which is why Brown was so conflicted. But there were
Cuban spies. He knew that. And here was this woman, taking a personal phone
call and heading out the door in the middle of what was—for a Cuban specialist
—just about the biggest crisis in a generation. And on top of that, she’s the one
who had arranged the awfully convenient Admiral Carroll briefing?
Brown told Carmichael that the Cubans had wanted to shoot down one of the
Hermanos al Rescate planes for years. But they hadn’t, because they knew what
a provocation that would be. It might serve as the excuse the United States

needed to depose Fidel Castro or launch an invasion. To the Cubans it wasn’t
worth it—unless, that is, they could figure out some way to turn public opinion
in their favor.
And so he finds out that Ana was not just one of the people in the room with
Admiral Carroll, but she’s the one who organized it. He looked at that and
went, “Holy shit, I’m looking at a Cuban counterintelligence influence
operation to spin a story, and Ana is the one who led the effort to meet with
Admiral Carroll. What the hell is that all about?”
Months passed. Brown persisted. Finally, Carmichael pulled Montes’s file.
She had passed her most recent polygraph with flying colors. She didn’t have a
secret drinking problem, or unexplained sums in her bank account. She had no
red flags. “After I had reviewed the security files and the personnel files on her, I
thought, Reg is way off base here,” Carmichael said. “This woman is gonna be
the next Director of Intelligence for DIA. She’s just fabulous.” He knew that in
order to justify an investigation on the basis of speculation, he had to be
meticulous. Reg Brown, he said, was “coming apart.” He had to satisfy Brown’s
suspicions, one way or another—as he put it, to “document the living shit out of
everything” because if word got out that Montes was under suspicion, “I knew I
was gonna be facing a shit storm.”
Carmichael called Montes in. They met in a conference room at Bolling. She
was attractive, intelligent, slender, with short hair and sharp, almost severe
features. Carmichael thought to himself, This woman is impressive. “When she
sat down, she was sitting almost next to me, about that far away”—he held his
hands three feet apart—“same side of the table. She crossed her legs. I don’t
think that she did it on purpose, I think she was just getting comfortable. I
happen to be a leg man—she couldn’t have known that, but I like legs and I
know that I glanced down.”
He asked her about the Admiral Carroll meeting. She had an answer. It wasn’t
her idea at all. The son of someone she knew at DIA had accompanied Carroll to
Cuba, and she’d gotten a call afterward.
She said, “I know his dad, his dad called me, and he said, ‘Hey, if you want
the latest scoop on Cuba, you should go see Admiral Carroll,’ and so I just
called up Admiral Carroll and we looked at our schedules and decided the
23rd of February was the most convenient date that works for both of us, and

that was it.”
As it turned out, Carmichael knew the DIA employee she was talking about.
He told her that he was going to call him up and corroborate her story. And she
said, “Please do.”
So what happened with the phone call in the situation room, he asked her?
She said she didn’t remember getting a phone call, and to Carmichael it seemed
as though she was being honest. It had been a crazy, hectic day, nine months
before. What about leaving early?
She said, “Well, yeah, I did leave.” Right away, she’s admitting to that. She’s
not denying stuff, which might be a little suspicious. She said, “Yeah, I did
leave early that day.” She says, “You know, it was on a Sunday, the cafeterias
were closed. I’m a very picky eater, I have allergies, so I don’t eat stuff out of
vending machines. I got there around six o’clock in the morning, it was
about…eight o’clock at night. I’m starving to death, nothing was going on,
they didn’t really need me, so I just decided I was going to get out of there.
Go home and eat something.”2 That rang true to me. It did.
After the interview, Carmichael set out to double-check her answers. The date
of the briefing really did seem like a coincidence. Her friend’s son had gone to
Cuba with Carroll.
I learned that yeah, she does have allergies, she doesn’t eat out of vending
machines, she’s very particular about what she eats. I thought, she’s there in
the Pentagon on a Sunday. I’ve been there, the cafeteria’s not open. She went
all day long without eating, she went home. I said, “Well, it kind of made
sense.”
What’d I have? I didn’t have anything. Oh well.
Carmichael told Reg Brown not to worry. He turned his attention to other
matters. Ana Montes went back to her office. All was forgotten and forgiven
until one day in 2001, five years later, when it was discovered that every night
Montes had gone home, typed up from memory all of the facts and insights she
had learned that day at work, and sent it to her handlers in Havana.
From the day she’d joined the DIA, Montes had been a Cuban spy.

3.
In the classic spy novel, the secret agent is slippery and devious. We’re
hoodwinked by the brilliance of the enemy. That was the way many CIA insiders
explained away Florentino Aspillaga’s revelations: Castro is a genius. The
agents were brilliant actors. In truth, however, the most dangerous spies are
rarely diabolical. Aldrich Ames, maybe the most damaging traitor in American
history, had mediocre performance reviews, a drinking problem, and didn’t even
try to hide all the money he was getting from the Soviet Union for his spying.
Ana Montes was scarcely any better. 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.
Brian Latell, the CIA Cuba specialist who witnessed the Aspillaga disaster,
knew Montes well.
“She used to sit across the table from me at meetings that I convened, when I
was [National Intelligence Officer],” Latell remembers. She wasn’t polished or
smooth. He knew that she had a big reputation within the DIA, but to him, she
always seemed a bit odd.
I would try to engage her, and she would always give me these strange
reactions.…When I would try to pin her down at some of these meetings that
I convened, on—“What do you think Fidel’s motives are about this?”—she
would fumble, in retrospect, the deer with the headlights in his eyes. She
balked. Even physically she would show some kind of reaction that caused
me to think, “Oh, she’s nervous because she’s just such a terrible analyst. She
doesn’t know what to say.”
One year, he says, Montes was accepted into the CIA’s Distinguished Analyst
Program, a research sabbatical available to intelligence officers from across the
government. Where did she ask to go? Cuba, of course.
“She went to Cuba funded by this program. Can you imagine?” Latell said. If
you were a Cuban spy, trying to conceal your intentions, would you request a
paid sabbatical in Havana? Latell was speaking almost twenty years after it had
happened, but the brazenness of her behavior still astounded him.
She went to Cuba as a CIA distinguished intelligence analyst. Of course, they

were delighted to have her, especially on our nickel, and I’m sure that they
gave her all kinds of clandestine tradecraft training while she was there. I
suspect—I can’t prove it, but I’m pretty sure—she met with Fidel. Fidel loved
to meet with his principal agents, to encourage them, to congratulate them, to
revel in the success they were having together against the CIA.
When Montes came back to the Pentagon, she wrote a paper in which she
didn’t even bother to hide her biases.
There should have been all kinds of red flags raised and guns that went off
when her paper was read by her supervisors, because she said things about the
Cuban military that make absolutely no sense, except from [the Cubans’]
point of view.
But did anyone raise those red flags? Latell says he never once suspected she
was a spy. “There were CIA officers of my rank, or close to my rank, who
thought she was the best Cuban analyst there was,” he said. So he rationalized
away his uneasiness. “I never trusted her, but for the wrong reasons, and that’s
one of my great regrets. I was convinced that she was a terrible analyst on Cuba.
Well, she was. Because she wasn’t working for us. She was working for Fidel.
But I never connected the dots.”
Nor did anyone else. 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.
In her cubicle, she had a quotation from Shakespeare’s Henry V taped to her wall
at eye level—for all the world to see.
The king hath note
of all that they intend,
By interception
Which they dream not of.

Or, to put it a bit more plainly: The Queen of Cuba takes note of all that the
U.S. intends, by means that all around her do not dream of.
The issue with spies is not that there is something brilliant about them. It is
that there is something wrong with us.

4.
Over the course of his career, the psychologist Tim Levine has conducted
hundreds of versions of the same simple experiment. He invites students to his
laboratory and gives them a trivia test. What is the highest mountain in Asia?
That kind of thing. If they answer the questions correctly, they win a cash prize.
To help them out, they are given a partner. Someone they’ve never met
before, who is, unknown to them, working for Levine. There’s an instructor in
the room named Rachel. Midway through the test, Rachel suddenly gets called
away. She leaves and goes upstairs. Then the carefully scripted performance
begins. The partner says, “I don’t know about you, but I could use the money. I
think the answers were left right there.” He points to an envelope lying in plain
sight on the desk. “It’s up to them whether they cheat or not,” Levine explains.
In about 30 percent of cases, they do. “Then,” Levine goes on, “we interview
them, asking, ‘Did you cheat?’”
The number of scholars around the world who study human deception is vast.
There are more theories about why we lie, and how to detect those lies, than
there are about the Kennedy assassination. In that crowded field, Levine stands
out. He has carefully constructed a unified theory about deception.3 And at the
core of that theory are the insights he gained from that first trivia-quiz study.
I watched videotapes of a dozen or so of those post-experiment interviews
with Levine in his office at the University of Alabama at Birmingham. Here’s a
typical one, featuring a slightly spaced-out young man. Let’s call him Philip.
Interviewer: All right, so…have you played Trivial Pursuit games…before?
Philip: Not very much, but I think I have.
Interviewer: In the current game did you find the questions difficult?
Philip: Yes, some were. I was like, “Well, what is that?”
Interviewer: If you would scale them one to ten, if one was easy and ten was
difficult, where do you think you would put them?

Philip: I would put them [at] an eight.
Interviewer: An eight. Yeah, they’re pretty tricky.
Philip is then told that he and his partner did very well on the test. The
interviewer asks him why.
Philip: Teamwork.
Interviewer: Teamwork?
Philip: Yeah.
Interviewer: OK, all right. Now, I called Rachel out of the room briefly.
When she was gone, did you cheat?
Philip: I guess. No.
Philip slightly mumbles his answer. Then looks away.
Interviewer: Are you telling the truth?
Philip: Yes.
Interviewer: Okay. When I interview your partner and I ask her, what is she
going to say?
At this point in the tape, there’s an uncomfortable silence, as if the student is
trying to get his story straight. “He’s obviously thinking very hard,” Levine said.
Philip: No.
Interviewer: No?
Philip: Yeah.
Interviewer: OK, all right. Well, that’s all I need from you.
Is Philip telling the truth? Levine has shown the Philip videotape to hundreds
of people and nearly every viewer correctly pegs Philip as a cheater. As the
“partner” confirmed to Levine, Philip looked inside the answer-filled envelope
the minute Rachel left the room. In his exit interview, he lied. And it’s obvious.
“He has no conviction,” Levine said.
I felt the same thing. In fact, when Philip is asked, “Did you cheat?” and
answers, “I guess. No,” I couldn’t contain myself, and I cried out, “Oh, he’s
terrible.” Philip was looking away. He was nervous. He couldn’t keep a straight
face. When the interviewer followed up with, “Are you telling the truth?” Philip

actually paused, as if he had to think about it first.
He was easy. But the more tapes we looked at, the harder it got. Here is a
second case. Let’s call him Lucas. He was handsome, articulate, confident.
Interviewer: I have to ask, when Rachel left the room, did any cheating
occur?
Lucas: No.
Interviewer: No? You telling me the truth?
Lucas: Yes, I am.
Interviewer: When I interview your partner and I ask her the same question,
what do you think she’s going to say?
Lucas: Same thing.
“Everybody believes him,” Levine said. I believed him. Lucas was lying.
Levine and I spent the better part of a morning watching his trivia-quiz
videotapes. By the end, I was ready to throw up my hands. I had no idea what to
make of anyone.
The point of Levine’s research was to try to answer one of the biggest puzzles
in human psychology: why are we so bad at detecting lies? You’d think we’d be
good at it. Logic says that it would be very useful for human beings to know
when they are being deceived. Evolution, over many millions of years, should
have favored people with the ability to pick up the subtle signs of deception. But
it hasn’t.
In one iteration of his experiment, Levine divided his tapes in half: twentytwo liars and twenty-two truth-tellers. On average, the people he had watch all
forty-four videos correctly identified the liars 56 percent of the time. Other
psychologists have tried similar versions of the same experiment. The average
for all of them? 54 percent. Just about everyone is terrible: police officers,
judges, therapists—even CIA officers running big spy networks overseas.
Everyone. Why?4
Tim Levine’s answer is called the “Truth-Default Theory,” or TDT.
Levine’s argument started with an insight that came from one of his graduate
students, Hee Sun Park. It was right at the beginning of Levine’s research, when
he was as baffled as the rest of his profession about why we are all so bad at
something that, by rights, we should be good at.
“Her big insight, the first one, was that the 54-percent deception-accuracy
figure was averaging across truths and lies,” Levine said. “You come to a very

different understanding if you break out…how much people are right on truths,
and how much people are right on lies.”
What he meant was this. If I tell you that your accuracy rate on Levine’s
videos is right around 50 percent, the natural assumption is to think that you are
just randomly guessing—that you have no idea what you are doing. But Park’s
observation was that that’s not true. We’re much better than chance at correctly
identifying the students who are telling the truth. But we’re much worse than
chance at correctly identifying the students who are lying. We go through all
those videos, and we guess—“true, true, true”—which means we get most of the
truthful interviews right, and most of the liars wrong. We have a default to truth:
our operating assumption is that the people we are dealing with are honest.
Levine says his own experiment is an almost perfect illustration of this
phenomenon. He invites people to play a trivia game for money. Suddenly the
instructor is called out of the room. And she just happens to leave the answers to
the test in plain view on her desk? Levine says that, logically, the subjects should
roll their eyes at this point. These are college students. They’re not stupid.
They’ve signed up for a psychological experiment. They’re given a “partner,”
whom they’ve never met, who is egging them on to cheat. You would think that
they might be even a little suspicious that things are not as they seem. But no!
“Sometimes, they catch that the instructor leaving the room might be a
setup,” Levine says. “The thing they almost never catch is that their partners are
fake.…So they think that there might be hidden agendas. They think it might be
a setup because experiments are setups, right? But this nice person they are
talking and chatting to? Oh no.” They never question it.
To snap out of truth-default mode requires what Levine calls a “trigger.” A
trigger is not the same as a suspicion, or the first sliver of doubt. 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.
This proposition sounds at first like the kind of hairsplitting that social
scientists love to engage in. It is not. It’s a profound point that explains a lot of
otherwise puzzling behavior.
Consider, for example, one of the most famous findings in all of psychology:
Stanley Milgram’s obedience experiment. In 1961, Milgram recruited volunteers

from New Haven to take part in what he said was a memory experiment. Each
was met by a somber, imposing young man named John Williams, who
explained that they were going to play the role of “teacher” in the experiment.
Williams introduced them to another volunteer, a pleasant, middle-aged man
named Mr. Wallace. Mr. Wallace, they were told, was to be the “learner.” He
would sit in an adjoining room, wired to a complicated apparatus capable of
delivering electrical shocks up to 450 volts. (If you’re curious about what 450
volts feels like, it’s just shy of the amount of electrical shock that leaves tissue
damage.)
The teacher-volunteer was instructed to give the learner a series of memory
tasks, and each time the learner failed, the volunteer was to punish him with an
ever-greater electrical shock, in order to see whether the threat of punishment
affected someone’s ability to perform memory tasks. As the shocks escalated,
Wallace would cry out in pain, and ultimately he started hammering on the walls.
But if the “teacher” wavered, the imposing instructor would urge them on:
“Please continue.”
“The experiment requires that you continue.”
“It is absolutely essential that you continue.”
“You have no other choice, you must go on.”
The reason the experiment is so famous is that virtually all of the volunteers
complied. Sixty-five percent ended up administering the max