Page 36 - Malcolm Gladwell - Talking to Strangers

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