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 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