Page 35 - Malcolm Gladwell - Talking to Strangers

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 shoot-down
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