Ana Montes assumed that the reason for her meeting with Carmichael was that he was performing a routine security check. All intelligence officers are periodically vetted so that they can continue to hold a security clearance. She was brusque.
“When she first came in she tried to blow me off by telling me—and it was true—she had just been named as the Acting Division Chief,” Carmichael remembered. “She had a ton of responsibilities, meetings and things to do, and she just didn’t have a lot of time.” Carmichael is a disarmingly boyish man, with fair hair and a substantial stomach. He looks, by his own estimation, like the late comedian and actor Chris Farley. She must have thought she could bully him. “I dealt with it the way you normally do,” he remembers:
The first time you just acknowledge it. You say, “Oh, I understand. Yeah, I heard that, congratulations, great. I understand you’ve got a limited amount of time.” And then you just kind of ignore it, because if it takes you twelve days, it takes twelve days. You don’t let them go. But then she hit me with it again.…She really made a point of it. I hadn’t even settled in yet and she said, “Oh, but seriously, I’ve gotta leave by two,” or something like that, “because I’ve got all these things to do.”
I’m like, “What the fuck?” That’s what I’m thinking.…I didn’t lose my temper, but I lost my patience. “Look, Ana. I have reason to suspect that you might be involved in a counterintelligence influence operation. We need to sit down and talk about this.” Bam! Right between the eyes.
Montes had been, by that point, a Cuban spy for nearly her entire government career. She had met with her handlers at least 300 times, handing over so many secrets that she ranks as one of the most damaging spies in U.S. history. She had secretly visited Cuba on several occasions. After her arrest, it was discovered that Fidel Castro had personally given her a medal. Through all of that, there hadn’t been even a whiff of suspicion. And suddenly, at the start of what she thought was a routine background check, a funny-looking Chris Farley character was pointing the finger at her. She sat there in shock.
“She was just looking at me like a deer looking at the headlights, waiting for me to say another word, just waiting.”
When Carmichael looked back on that meeting years later, he realized that was the first clue he had missed: her reaction made no sense.
I just didn’t pick up on the fact that she never said, “What are you talking about?” Nothing like that. She didn’t say a freaking word. She just sat there and was listening. If I’d been astute, I’d have picked up on that. No denial, no confusion, no anger. Anybody who has been told they’re suspected of murder or something.…If they’re completely innocent it’s like, “What do you mean?” They’re going to say, “Wait a minute, you just accused me of some…I want to know what the fuck this is all about.” Eventually, they’ll get in your face, they’ll really get in your face. Ana didn’t do a freaking thing except sit there.
Carmichael had doubts, right from the beginning. But doubts trigger disbelief only when you can’t explain them away. And he could easily explain them away. She was the Queen of Cuba, for goodness’ sake. How could the Queen of Cuba be a spy? He had said that line to her—“I have reason to suspect that you might be involved in a counterintelligence influence operation”—only because he wanted her to take the meeting seriously. “I was anxious to get into it and get to the next step. Like I said, I’m just patting myself on the back: ‘That worked, that shut her up. I’m not going to hear any more of that crap anymore. Now, let’s get to this, get this done.’ That’s why I missed it.”
They talked about the Admiral Carroll briefing. She had a good answer. They talked about why she abruptly left the Pentagon that day. She had an answer. She was being flirty, a little playful. He began to relax. He looked down at her legs again.
Ana started doing this thing. She’s got her legs crossed and she’s bouncing her toe, like that. I don’t know if it was conscious…but what I do know is, that catches your eye.…We got more comfortable with one another, and she became just a little bit more flirty. Flirty? I don’t know, but cute sometimes in some of her responses to questions.
They talked about the phone call. She said she never got a phone call, or at least she didn’t remember getting one. It should have been another red flag: the people who were with her that day in the situation room distinctly remembered her getting a phone call. But then again, it had been a long and stressful day. They had all been in the middle of an international crisis. Maybe they had confused her with someone else.
There was one other thing—another moment when Carmichael saw something in her reaction that made him wonder. Near the end of the interview, he asked Montes a series of questions about what happened after she left the Pentagon that day. It was a standard investigative procedure. He just wanted as complete a picture as possible of her movements that evening.
He asked her what she did after work. She said she drove home. He asked her where she parked. She said in the lot across the street. He asked her if she saw anyone else as she was parking. Did she say hello to anyone? She said no.
I said, “OK, well, so what’d you do? You parked your car and you walked across the street”—and while I’m doing this is when the change of demeanor occurred. Keep in mind, I’d been talking to her for almost two hours and by that time, Ana and I were almost like buddies, not that close, but we have a great rapport going. She’s actually joking about stuff and making funny remarks every once in a while about stuff—it’s that casual and that warm, if you will.
Then all of a sudden, this huge change came over her. You could see it, one minute she’s just almost flirting and stuff, having a good time.…All of a sudden she changed. It’s like a little kid who has been caught with his hand in the cookie jar, and he’s got it behind his back, and Mom says, “What do you have?” She was looking at me and denying, but…with that look like, “What do you know? How do you know? Are you going to catch me? I don’t want to get caught.”
After her arrest, investigators discovered what had really happened that night. The Cubans had an arrangement with her: if she ever spotted one of her old handlers on the street, it meant that her spymasters urgently needed to talk to her in person. She should keep walking and meet them the following morning at a prearranged site. That night, when she got home from the Pentagon, she saw one of her old handlers standing by her apartment building. So when Carmichael asked her, pointedly, “Who did you see? Did you see anyone as you came home?” she must have thought that he knew about the arrangement—that he was on to her.
She was scared to fucking death. She thought I knew it and I didn’t. I had no idea, I didn’t know what I had. I knew I had something, I knew there was something. After the interview, I would look back on it…and what did I do? I did the same thing every human being does.…I rationalized it away.
I thought, Well, maybe she’s been seeing a married guy…and she didn’t want to tell me. Or maybe she’s a lesbian or something and she was hooking up with a girlfriend that she doesn’t want us to know [about], and she’s worried about that. I started thinking about all these other possibilities and I sort of accepted it, just enough so that I wouldn’t keep going crazy. I accepted it.