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.
There should have been all kinds of red flags raised and guns that went off when her paper was read by her supervisors, because she said things about the Cuban military that make absolutely no sense, except from [the Cubans’] point of view.
But did anyone raise those red flags? Latell says he never once suspected she was a spy. “There were CIA officers of my rank, or close to my rank, who thought she was the best Cuban analyst there was,” he said. So he rationalized away his uneasiness. “I never trusted her, but for the wrong reasons, and that’s one of my great regrets. I was convinced that she was a terrible analyst on Cuba. Well, she was. Because she wasn’t working for us. She was working for Fidel. But I never connected the dots.”
Nor did anyone else. Montes had a younger brother named Tito, who was an FBI agent. He had no idea. Her sister was also an FBI agent, who in fact played a key role in exposing a ring of Cuban spies in Miami. She had no idea. Montes’s boyfriend worked for the Pentagon as well. His specialty, believe it or not, was Latin American intelligence. His job was to go up against spies like his girlfriend. He had no idea. When Montes was finally arrested, the chief of her section called her coworkers together and told them the news. People started crying in disbelief. The DIA had psychologists lined up to provide on-site counseling services. Her supervisor was devastated. None of them had any idea. In her cubicle, she had a quotation from Shakespeare’s Henry V taped to her wall at eye level—for all the world to see.
The king hath note
of all that they intend,
By interception
Which they dream not of.
Or, to put it a bit more plainly: The Queen of Cuba takes note of all that the U.S. intends, by means that all around her do not dream of.
The issue with spies is not that there is something brilliant about them. It is that there is something wrong with us.
4.
Over the course of his career, the psychologist Tim Levine has conducted hundreds of versions of the same simple experiment. He invites students to his laboratory and gives them a trivia test. What is the highest mountain in Asia? That kind of thing. If they answer the questions correctly, they win a cash prize.
To help them out, they are given a partner. Someone they’ve never met before, who is, unknown to them, working for Levine. There’s an instructor in the room named Rachel. Midway through the test, Rachel suddenly gets called away. She leaves and goes upstairs. Then the carefully scripted performance begins. The partner says, “I don’t know about you, but I could use the money. I think the answers were left right there.” He points to an envelope lying in plain sight on the desk. “It’s up to them whether they cheat or not,” Levine explains. In about 30 percent of cases, they do. “Then,” Levine goes on, “we interview them, asking, ‘Did you cheat?’”
The number of scholars around the world who study human deception is vast. There are more theories about why we lie, and how to detect those lies, than there are about the Kennedy assassination. In that crowded field, Levine stands out. He has carefully constructed a unified theory about deception.3 And at the core of that theory are the insights he gained from that first trivia-quiz study.
I watched videotapes of a dozen or so of those post-experiment interviews with Levine in his office at the University of Alabama at Birmingham. Here’s a typical one, featuring a slightly spaced-out young man. Let’s call him Philip.
Interviewer: All right, so…have you played Trivial Pursuit games…before?
Philip: Not very much, but I think I have.