Page 43 - Malcolm Gladwell - Talking to Strangers

disarmingly boyish man, with fair hair and a substantial stomach. He looks, by his own estimation,
like the late comedian and actor Chris Farley. She must have thought she could bully him. “I dealt
with it the way you normally do,” he remembers:
The first time you just acknowledge it. You say, “Oh, I understand. Yeah, I heard that,
congratulations, great. I understand you’ve got a limited amount of time.” And then you just kind
of ignore it, because if it takes you twelve days, it takes twelve days. You don’t let them go. But
then she hit me with it again.…She really made a point of it. I hadn’t even settled in yet and she
said, “Oh, but seriously, I’ve gotta leave by two,” or something like that, “because I’ve got all
these things to do.”
I’m like, “What the fuck?” That’s what I’m thinking.…I didn’t lose my temper, but I lost my
patience. “Look, Ana. I have reason to suspect that you might be involved in a
counterintelligence influence operation. We need to sit down and talk about this.” Bam! Right
between the eyes.
Montes had been, by that point, a Cuban spy for nearly her entire government career. She had
met with her handlers at least 300 times, handing over so many secrets that she ranks as one of the
most damaging spies in U.S. history. She had secretly visited Cuba on several occasions. After her
arrest, it was discovered that Fidel Castro had personally given her a medal. Through all of that,
there hadn’t been even a whiff of suspicion. And suddenly, at the start of what she thought was a
routine background check, a funny-looking Chris Farley character was pointing the finger at her.
She sat there in shock.
“She was just looking at me like a deer looking at the headlights, waiting for me to say another
word, just waiting.”
When Carmichael looked back on that meeting years later, he realized that was the first clue he
had missed: her reaction made no sense.
I just didn’t pick up on the fact that she never said, “What are you talking about?” Nothing like
that. She didn’t say a freaking word. She just sat there and was listening. If I’d been astute, I’d
have picked up on that. No denial, no confusion, no anger. Anybody who has been told they’re
suspected of murder or something.…If they’re completely innocent it’s like, “What do you
mean?” They’re going to say, “Wait a minute, you just accused me of some…I want to know
what the fuck this is all about.” Eventually, they’ll get in your face, they’ll really get in your face.
Ana didn’t do a freaking thing except sit there.
Carmichael had doubts, right from the beginning. But doubts trigger disbelief only when you
can’t explain them away. And he could easily explain them away. She was the Queen of Cuba, for
goodness’ sake. How could the Queen of Cuba be a spy? He had said that line to her—“I have
reason to suspect that you might be involved in a counterintelligence influence operation”—only
because he wanted her to take the meeting seriously. “I was anxious to get into it and get to the next
step. Like I said, I’m just patting myself on the back: ‘That worked, that shut her up. I’m not going
to hear any more of that crap anymore. Now, let’s get to this, get this done.’ That’s why I missed it.”
They talked about the Admiral Carroll briefing. She had a good answer. They talked about why
she abruptly left the Pentagon that day. She had an answer. She was being flirty, a little playful. He
began to relax. He looked down at her legs again.
Ana started doing this thing. She’s got her legs crossed and she’s bouncing her toe, like that. I
don’t know if it was conscious…but what I do know is, that catches your eye.…We got more
comfortable with one another, and she became just a little bit more flirty. Flirty? I don’t know,
but cute sometimes in some of her responses to questions.
They talked about the phone call. She said she never got a phone call, or at least she didn’t
remember getting one. It should have been another red flag: the people who were with her that day
in the situation room distinctly remembered her getting a phone call. But then again, it had been a
long and stressful day. They had all been in the middle of an international crisis. Maybe they had
confused her with someone else.
There was one other thing—another moment when Carmichael saw something in her reaction
that made him wonder. Near the end of the interview, he asked Montes a series of questions about
what happened after she left the Pentagon that day. It was a standard investigative procedure. He