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 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 need me, so I just decided I was going to get out of there. Go home and eat something.”2 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.