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