Page 37 - Malcolm Gladwell - Talking to Strangers

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need me, so I just decided I was going to get out of there. Go home and eat something.” 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.