Talking to Strangers

by Malcolm Gladwell

  The response to the attack was immediate. The United Nations Security Council passed a resolution denouncing the Cuban government. A grave President Clinton held a press conference. The Cuban emigré population in Miami was furious. The two planes had been shot down in international airspace, making the incident tantamount to an act of war. The radio chatter among the Cuban pilots was released to the press:

  “We hit him, cojones, we hit him.”

  “We retired them, cojones.”

  “We hit them.”

  “Fuckers.”

  “Mark the place where we retired them.”

  “This one won’t fuck with us anymore.”

  And then, after one of the MiGs zeroed in on the second Cessna:

  “Homeland or death, you bastards.”

  But in the midst of the controversy, the story suddenly shifted. A retired U.S. rear admiral named Eugene Carroll gave an interview to CNN. Carroll was an influential figure inside Washington. He had formerly served as the director of all U.S. armed forces in Europe, with 7,000 weapons at his disposal. Just before the Hermanos al Rescate shoot-down, Carroll said, he and a small group of military analysts had met with top Cuban officials.

  CNN: Admiral, can you tell me what happened on your trip to Cuba, who you spoke with and what you were told?

  Carroll: We were hosted by the Ministry of Defense. General Rosales del Toro.… We traveled around, inspected Cuban bases, Cuban schools, their partially completed nuclear power plant, and so on. In long discussions with General Rosales del Toro and his staff the question came up about these overflights from U.S. aircraft—not government aircraft, but private airplanes operating out of Miami. They asked us, “What would happen if we shot one of these down? We can, you know.”

  Carroll interpreted that question from his Cuban hosts as a thinly veiled warning. The interview continued:

  CNN: So when you returned, who did you relay this information to?

  Carroll: As soon as we could make appointments, we discussed the situation…with members of the State Department and members of the Defense Intelligence Agency.

  The Defense Intelligence Agency—the DIA—is the third arm of the foreign intelligence triumvirate in the U.S. government, along with the CIA and the National Security Agency. If Carroll had met with the State Department and the DIA, he had delivered the Cuban warning about as high up in the American government as you could go. And did the State Department and DIA take those warnings to heart? Did they step in and stop Hermanos al Rescate from continuing their reckless forays into Cuban airspace? Obviously not.1

  Carroll’s comments ricocheted around Washington, DC, policy circles. This was an embarrassing revelation. The Cuban shoot-down happened on February 24. Carroll’s warnings to the State Department and DIA were delivered on February 23. A prominent Washington insider met with U.S. officials the day before the crisis, explicitly warned them that the Cubans had lost patience with Hermanos al Rescate, and his warning was ignored. What began as a Cuban atrocity was now transformed into a story about American diplomatic incompetence.

  CNN: But what about the position that these were unarmed civilian planes?

  Carroll repeated what he had been told in Havana.

  Carroll: That is a very sensitive question. Where were they? What were they doing? I’ll give you an analogy. Suppose we had the planes flying over San Diego from Mexico, dropping leaflets and inciting against [California] Governor Wilson. How long would we tolerate these overflights after we had warned them against it?

  Fidel Castro wasn’t being invited onto CNN to defend himself. But he didn’t need to be. He had a rear admiral making his case.

  2.

  The next three chapters of Talking to Strangers are devoted to the ideas of a psychologist named Tim Levine, who has thought as much about the problem of why we are deceived by strangers as anyone in social science. The second chapter looks at Levine’s theories through the story of Bernie Madoff, the investor who ran the largest Ponzi scheme in history. The third examines the strange case of Jerry Sandusky, the Pennsylvania State University football coach convicted of sexual abuse. And this, the first, is about the fallout from that moment of crisis between the United States and Cuba in 1996.

  Does anything about Admiral Carroll and the Cuban shoot-downs strike you as odd? There are an awful lot of coincidences here.

  The Cubans plan a deliberate murderous attack on U.S. citizens flying in international airspace.

  It just so happens that the day before the attack, a prominent military insider delivers a stern warning to U.S. officials about the possibility of exactly that action.

  And, fortuitously, that warning puts that same official, the day after the attack, in a position to make the Cuban case on one of the world’s most respected news networks.

  The timing of those three events is a little too perfect, isn’t it? If you were a public relations firm, trying to mute the fallout from a very controversial action, that’s exactly how you’d script it. Have a seemingly neutral expert available—right away—to say, “I warned them!”

  This is what a military counterintelligence analyst named Reg Brown thought in the days after the incident. Brown worked on the Latin American desk of the Defense Intelligence Agency. His job was to understand the ways in which the Cuban intelligence services were trying to influence American military operations. His business, in other words, was to be alert to the kinds of nuances, subtleties, and unexplained coincidences that the rest of us ignore, and Brown couldn’t shake the feeling that somehow the Cubans had orchestrated the whole crisis.

  It turned out, for example, that the Cubans had a source inside Hermanos al Rescate—a pilot named Juan Pablo Roque. On the day before the attack, he had disappeared and resurfaced at Castro’s side in Havana. Clearly Roque told his bosses back home that Hermanos al Rescate had something planned for the 24th. That made it difficult for Brown to imagine that the date of the Carroll briefing had been chosen by chance. For maximum public relations impact, the Cubans would want their warning delivered the day before, wouldn’t they? That way the State Department and the DIA couldn’t wiggle out of the problem by saying that the warning was vague, or long ago. Carroll’s words were right in front of them on the day the pilots took off from Miami.

  So who arranged that meeting? Brown wondered. Who picked February 23? He did some digging, and the name he came up with startled him. It was a colleague of his at the DIA, a Cuban expert named Ana Belen Montes. Ana Montes was a star. She had been selected, repeatedly, for promotions and special career opportunities, showered with accolades and bonuses. Her reviews were glowing. She had come to the DIA from the Department of Justice, 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 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.

  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 stran
ge 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.