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.
Ana Montes wasn’t a master spy. She didn’t need to be. In a world where our lie detector is set to the “off” position, a spy is always going to have an easy time of it. And was Scott Carmichael somehow negligent? Not at all. He did what Truth-Default Theory would predict any of us would do: he operated from the assumption that Ana Montes was telling the truth, and—almost without realizing it—worked to square everything she said with that assumption. We need a trigger to snap out of the default to truth, but the threshold for triggers is high. Carmichael was nowhere near that point.
The simple truth, Levine argues, is that lie detection does not—cannot—work the way we expect it to work. In the movies, the brilliant detective confronts the subject and catches him, right then and there, in a lie. But in real
life, accumulating the amount of evidence necessary to overwhelm our doubts takes time. You ask your husband if he is having an affair, and he says no, and you believe him. Your default is that he is telling the truth. And whatever little inconsistencies you spot in his story, you explain away. But three months later you happen to notice an unusual hotel charge on his credit-card bill, and the combination of that and the weeks of unexplained absences and mysterious phone calls pushes you over the top. That’s how lies are detected.
This is the explanation for the first of the puzzles, why the Cubans were able to pull the wool over the CIA’s eyes for so long. That story is not an indictment of the agency’s competence. It just reflects the fact that CIA officers are—like the rest of us—human, equipped with the same set of biases to truth as everyone else.
Carmichael went back to Reg Brown and tried to explain.
I said, “Reg, I realize what it looks like to you, I understand your reasoning that you think that this is a deliberate influence operation. Looks like it. But if it was, I can’t point a finger [to] it to say she was part of a deliberate effort. It just doesn’t make any sense.…At the end of the day, I just had to close out the case.”
6.
Four years after Scott Carmichael’s interview with Ana Montes, one of his colleagues at the DIA met an analyst for the National Security Agency at an interagency meeting. The NSA is the third arm of the U.S. intelligence network, along with the CIA and the DIA. They are the code-breakers, and the analyst said that her agency had had some success with the codes that the Cubans were using to communicate with their agents.
The codes were long rows of numbers, broadcast at regular intervals over shortwave radio, and the NSA had managed to decode a few snippets. They had given the list of tidbits to the FBI two and a half years before, but had heard nothing back. Out of frustration, the NSA analyst decided to share a few details with her DIA counterpart. The Cubans had a highly placed spy in Washington whom they called “Agent S,” she said. Agent S had an interest in something called a “safe” system. And Agent S had apparently visited the American base at Guantánamo Bay in the two-week time frame from July 4 to July 18, 1996.
The man from the DIA was alarmed. “SAFE”5 was the name of the DIA’s internal computer-messaging archive. That strongly suggested that Agent S was at the DIA, or at least closely affiliated with the DIA. He came back and told his supervisors. They told Carmichael. He was angry. The FBI had been working on a spy case potentially involving a DIA employee for two and a half years, and they hadn’t told him? He was the DIA’s counterintelligence investigator!
He knew exactly what he had to do—a search of the DIA computer system. Any Department of Defense employee who travels to Guantánamo Bay needs to get approval. They need to send two messages through the Pentagon system, asking first for permission to travel and then for permission to talk to whomever they wish to interview at the base.
“Okay, so two messages,” Carmichael said.
He guessed that the earliest anyone traveling to Guantánamo Bay in July would apply for their clearances was April. So he had his search parameters: travel-authority and security-clearance requests from DIA employees regarding Guantánamo Bay made between April 1 and July 18, 1996. He told his coworker, “Gator” Johnson, to run the same search simultaneously. Two heads would be better than one.
What [the computer system] did back in those days, it would set up a hit file. It would electronically stack up all your messages and tell you, “You’ve got X number of hits.” I can hear Gator over there…I can hear him tapping away and I knew he hadn’t even finished his query yet and I already had my hit file to go through, so I thought, I’m going through them real quickly, just to see if any [name] pops out at me, and that’s when I’m pretty sure it was the twentieth one hit me. It was Ana B. Montes. The game was fucking over, and I mean it was over in a heartbeat.…I was really stunned—speechless stunned. I could have fallen out of my chair. I literally backed up—I was on wheels—I was literally distancing myself from this bad news.…I literally backed up all the way to the end of my cubicle and Gator is still going dink-pink-tink-tink.
I said, “Oh shit.”
1 The State Department had informed Hermanos al Rescate, through official channels, that any flight plan with Cuba as a destination was unacceptable. But clearly those warnings weren’t working.
CNN: Admiral, the State Department had issued other warnings to Brothers to the Rescue about this, haven’t they?
Carroll: Not effective ones.…They know that [Brothers] have been filing flight plans that were false and then going to Cuba, and this was part of the Cuban resentment, was that the government wasn’t enforcing its own regulations.
2 This was in fact true. Montes strictly controlled her diet, at one point limiting herself to “eating only unseasoned boiled potatoes.” CIA-led psychologists later concluded she had borderline OCD. She also took very long showers with different types of soap and wore gloves when she drove her car. Under the circumstances, it’s not surprising that people would explain away their suspicions about her often-strange behavior.
3 Levine’s theories are laid out in his book, Duped: Truth-Default Theory and the Social Science of Lying and Deception (Tuscaloosa, AL: University of Alabama Press, 2019). If you want to understand how deception works, there is no better place to start.
4 In my book Blink, I wrote of Paul Ekman’s claim that a small number of people are capable of successfully detecting liars. For more on the Ekman-Levine debate, see the extended commentary in the Notes.
5 SAFE stands for Security Analyst File Environment. I love it when people start with the acronym and work backward to create the full name.
Chapter Four
The Holy Fool
1.
In November 2003, Nat Simons, a portfolio manager for the Long Island–based hedge fund Renaissance Technologies, wrote a worried email to several of his colleagues. Through a complicated set of financial arrangements, Renaissance found itself with a stake in a fund run by an investor in New York named Bernard Madoff, and Madoff made Simons uneasy.
If you worked in the financial world in New York in the 1990s and early 2000s, chances are you’d heard of Bernard Madoff. He worked out of an elegant office tower in Midtown Manhattan called the Lipstick Building. He served on the boards of a number of important financial-industry associations. He moved between the monied circles of the Hamptons and Palm Beach. He had an imperious manner and a flowing mane of white hair. He was reclusive, secretive. And that last fact was what made Simons uneasy. He’d heard rumors. Someone he trusted, he wrote in the group email, “told us in confidence that he believes that Madoff will have a serious problem within a year.”
He went on: “Throw in that his brother-in-law is his auditor and his son is also high up in the organization, and you have the risk of some nasty allegations, the freezing of accounts, etc.”
The next day Henry Laufer, one of the firm’s senior executives, wrote back. He agreed. Renaissance, he added, had “independent evidence” that something was amiss with Madoff. Then Renaissance’s risk manager, Paul Broder—the person responsible for making sure the fund didn’t put its money anywhere dangerous—weighed in with a long, detailed analysis of the trading strategy that Madoff claimed to be using. “None of it seems to add up,” he concluded. The three of them decided to conduct their own in-house investigation. Their suspicions deepened. “I came to the conclusion that we didn’t understand what he was doing,” Broder would say later. “We had no idea how he was making his money. The volume numbers that he suggested he was doing [were] not supported by any evidence we could find.” Renaissance had doubts.
So did Renaissance sell off its stake in Madoff? Not quite. They cut their stake in half. They hedged their bets. Five years later, after Madoff had been exposed as a fraud—the mastermind of the biggest Ponzi scheme in history—federal investigators sat down with Nat Simons and asked him to explain why. “I never, as the mana
ger, entertained the thought that it was truly fraudulent,” Simons said. He was willing to admit that he didn’t understand what Madoff was up to, and that Madoff smelled a little funny. But he wasn’t willing to believe that he was an out-and-out liar. Simons had doubts, but not enough doubts. He defaulted to truth.
The emails written between Simons and Laufer were discovered during a routine audit by the Securities and Exchange Commission (SEC), the agency responsible for monitoring the hedge-fund industry. It wasn’t the first time the SEC had run across doubts about Madoff’s operations. Madoff claimed to follow an investment strategy linked to the stock market, which meant that like any other market-based strategy, his returns ought to go up and down as the market went up and down. But Madoff’s returns were rock steady—which defied all logic. An SEC investigator named Peter Lamore once went to see Madoff to get an explanation. Madoff’s answer was that, essentially, he could see around corners; he had an infallible “gut feel” for when to get out of the market just before a downswing, and back into the market just before an upswing. “I asked him repeatedly,” Lamore recalled later:
I thought his gut feel was, you know, strange, suspicious. You know, I kept trying to press him. I thought there was something else…I thought, you know, he was getting some sort of insight into the overall broad market that other people weren’t getting. So I repeatedly sort of pressed him on that. I asked Bernie repeatedly over and over again, and at some point, I mean, I’m not sure what else to do.
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