It all started last Wednesday night, after the first day of the Aspen Security Forum, perhaps the most high-level annual gathering of national security types: spooks, former spooks, people who rely on spooks to set U.S. foreign policy, people who write about spooks, people who study spooks, and any politicians who want to participate in the forum. That night, after FBI director Christopher Wray had delivered a milquetoast performance on a panel, and after a group of some three dozen national security journalists had sated themselves at Jimmy's, a local steakhouse, I stood waiting for an Uber with my friend Shane Harris, who reports on the intelligence community for The Washington Post.
Finally, a car pulled up and our designated Uber driver, a woman I'll call Gloria, welcomed us in. She was an older woman, somewhere in her sixties, and had a sweet and heavy Hispanic accent. It was all very standard Uber chit-chat fare: Have you been to Aspen before? What brings you here? Then we dropped Shane off at his hotel, and on we went to mine.
“So what's going on with North Korea?” Gloria asked. “What are people saying?”
I murmured something as I dug around Instagram.
“You know, I've been to North Korea,” Gloria said.
I looked up.
“What?” I asked, startled. “How? When?”
“As part of a delegation.”
“What kind of delegation?” I asked. Gloria was silent, driving through the dark streets. It's notoriously difficult to get into—let alone out of—the Hermit Kingdom. How did Gloria the Uber driver manage it?
“What kind of work do you do?” I asked her. “I mean, other than the Uber driving.”
“I'm a person of faith,” Gloria said mysteriously.
“When were you in North Korea?” I asked. Gloria said nothing. “What were you doing there?” Silence still.
“Here you are,” she finally said, and I got out in the dark meadow in front of my hotel, wondering just who this Uber driver was.
The next morning, a group of journalists stood around waiting for FBI director Wray to arrive at this off-the-record briefing, and as we waited, huffing coffee, talk turned to Gloria. She had driven Shane here this morning and asked him about what he expected to hear at the conference. She had pumped another reporter, a national security correspondent with one of the major networks, for information. “I'll tell you something if you tell me something,” the correspondent recalled her saying. She laughed, we all laughed, but it was now leavened with a good bit of alarm. Was Gloria something more than a mere Uber driver?
“We have to tell Wray about her,” said Deb Riechmann of the Associated Press. We all laughed because we knew she was joking, but only kind of. “Being in this environment makes you hyper-sensitive to it,” Deb told me later when we compared notes on our drives with Gloria. Neither of us was sure if Gloria was a spy or if we were crazy, or both. Deb made a good point: “It is strange that the first thing she asks about when you get in the car is 'What have you heard about North Korea?’ ”
Gloria had also driven Shane a few more times, and he was also growing concerned that Gloria was more than just an Uber driver in a mountain resort town. “She was way more interested in what was going on than any other Uber drivers I've had,” Shane told me. “She was like, 'Come on, what's happening, give me the skinny.' She seemed very aware of what was happening here and that this was a very big security conference.”
Gloria had driven Shane the day after Dan Coats, the Director of National Intelligence, learned on stage at the Forum that his boss, Trump, had just invited Vladimir Putin to the White House. His stunned reaction—“Okaaaaaaay. That's going to be special”—had set Washington aflame for the umpteenth time that week. And Gloria wanted to know how it all went down. “I was like, you know Dan Coats, the top intelligence official, and she was like, 'Yes, the DNI,' ” Shane recounted, using the inside-the-Beltway abbreviation for Director of National Intelligence. “She knew who the DNI was, she called him the DNI—no one calls him the DNI!”
Shane and I were sitting on a couch in a meadow outside the conference, puzzling over our mysterious driver. Were we being paranoid or, worse yet, racist and classist? Why wouldn't an Uber driver be interested in foreign policy, especially at a time when the president seemed to be running nearly daily sprints between the precipice of world war and declarations that he had brought about world peace? And anyone with a smart phone or a TV would have seen the wall-to-wall coverage of DNI Coats's stuttering surprise. There seemed no escaping it, especially for someone as interested in the news as Gloria seemed to be.
I put this theory to Shane: Was this just the bigotry of our low expectations? Shane hesitated. “Let's put it this way: Her grasp of the issues and her sense of what was immediately going to be the point of conflict was a bit more sophisticated than a normal Uber driver's,” he finally said. “Which is not to say that Uber drivers don't understand politics, but most of the time it's like, 'Trump sure is crazy!' or 'Boy, those people sure won't leave Trump alone!' But she was much more sophisticated.” We sat with this thought for a beat. “But could she be a spy? I don't know,” Shane said. “She says she went to North Korea. I don't know that many people who have gone to North Korea!”
Earlier that afternoon, I had buttonholed Representative Will Hurd of Texas. Hurd, a Republican and former CIA operative, had made waves in condemning Trump's performance at the Helsinki Summit with Putin. Hurd had been welcomed at the Forum as a hero for speaking truth to power, but I wanted to ask him about Gloria.
“First off, this is 100 percent a target-rich environment,” Hurd told me. At the Aspen Security Forum, “you have people who are intimately involved in setting national security policy, so when you have this concentration of people involved in the industry, it's always a good target, so people should be careful about the conversations they're having, whether it's in a taxi or an Uber or at a restaurant. Because I would not be surprised if there were folks that were interested in trying to overhear what was going on here or make contact.”
I had expected Hurd to squelch my blooming paranoia with some dismissive laughter. Instead, his warning kindled two contradictory impulses in me. On the one hand, I resolved to be less chatty in Ubers, but now I was even more curious about Gloria. What was she up to?
I texted Gloria and asked her to pick me up in downtown Aspen (where I had been running an errand) and take me back to the conference site. Her car pulled up and she welcomed me in, as warm and cheerful as ever.
“Hiiiii! How aaaaare you?” she nearly sang. We quickly established that I was good, and she was also good. Now it was time to get real.
Have you been driving a lot of people from the conference? I asked her.
“Yes, yes,” she said. “A lot.”
I told her I found her fascinating and wanted to write a story about her. She paused and asked why, but ultimately agreed.
So how did you get into driving Uber? I asked her.
“I used to live in my own world, so when I started driving Uber, I started seeing the world in a different way, absorbing information a different way,” she told me. Strange, I thought, scribbling in my notebook. Was she just a curious, open spirit, or was she absorbing information on someone's behalf?
I asked her where she was from. She told me about her life in Central America and about the violent drug cartels that operated there.
I sat in the back seat, listening to her story and slowly filling with guilt: This was just a sweet older lady who had fled violence and made a new home for herself here, serving the wealthy Angelenos who had their second—or fourth—homes here. I felt bad about my assumptions and decided to stop being so nosy about Gloria.
“Since I saw your face yesterday, I've been wondering,” she said, “are you from a Russian background?”
Suddenly, I was jolted from my self-flagellating reverie. How the hell did Gloria know I was from Russia? I certainly hadn't mentioned it, and my last name wasn't on my Uber profile. And, since I'm Jewish, I don't even look particularly Russian—that is, classically Slavic. What else did Gloria know, and how did she know it?
How did you know? I asked her.
Gloria resorted to flattery. “Because your face is so beautiful,” she cooed. “The dark hair and the light eyes and the white skin.”
I wasn't buying it.
How did you know I was from Russia? I asked her again.
“I saw yesterday your eyes a little bit, and I thought, she's so beautiful,” she said. “But it was dark and now I see your face more in the day.” She repeated the characteristics that she felt made me Russian, seasoned with even more gratuitous flattery.
How did you know I was from Russia? I repeated, totally rattled.
“So what is going on with Putin now?” she asked, quickly changing the subject. “What is happening?”
I managed something about Trump inviting him to the White House in the fall.
“Why is he doing this thing?” Gloria asked.
“I don't know,” I said and, trying to steer the conversation back to her, I asked, “Do you understand it?”
“I don't know,” Gloria said, again squirming out of my grasp. “I want to understand. I think I hear he wants—” she stopped herself. “I think it's interesting,” she said.
“Why do you think he wants to meet with Putin?” I asked.
“What do you think about that?” Gloria parried.
“I think because he helped him win the election?” I offered. “What do you think?”
“I think—are you having dinner? Enjooooy!”
And just like that, the ride—and my interview—was over.
How had she known I was from Russia?
“I bet she looked up your credit card,” Shane posited.
“Or ran my user pic through a Google Image search?” I tried.
I felt increasingly paranoid. Part of it was the fact that I was surrounded for a few intense and saturated days by people who saw Russian—or Chinese or North Korean—spies and their malign influence everywhere. Part of it was that I had been so highly skeptical of their seemingly fantastical theories of Russian interference that I had missed some key things just under my nose. Just days before, Maria Butina, an alleged Russian agent, had been arrested in Washington, D.C., and charged for her role in an elaborate campaign to spy on and influence American conservative politics. I had written a profile of Butina back in 2012, when I was still living in Moscow, and because it had never occurred to me that she might be an agent of the Russian security services, I had ignored her requests to hang out when she, too, moved to Washington. Now she was the redheaded Russian spy, and I felt like an idiot for missing her now obvious connections to the Kremlin. What else had I missed?
At the Aspen Security Forum, I was marooned in the mountains with people who never used public Wi-Fi, who seemed to be able to spot a Russian spy before he opened his mouth—and that was just the journalists. We were eating and talking and drinking with men and women who had served at the highest level of the American government, as well as in its intelligence agencies, the most decorated veterans of the Deep State. Over the past two years, their most dire diagnoses had been borne out by press reports, by Robert Mueller's indictments, and by Trump's increasingly bizarre behavior. It was they, and not the skeptics, who had been right. The Russians had intervened in the 2016 election and infiltrated Trump's campaign, and they'd gone far deeper than anyone had anticipated. So who was crazy now? Those of us who had dismissed their vein-popping alarm as paranoia, or the people who had been trained to look for spies in our midst and who rang the alarm when they spotted them?
I asked a well-known figure in national security and Russiagate circles what he thought of my Gloria obsession. I expected him to dismiss it, but he didn't. “There's a lot of spies around,” said the well-known figure, who asked to remain nameless because of potential legal issues involved in speaking to the press. “These days, whatever paranoid fantasy you can come up with has a halfway decent chance of being true. I mean, the NRA really was infiltrated by the Russians.”
I decided to ask John McLaughlin, the former acting head of the CIA and the unofficial mayor of the Forum, if it were feasible to run an intelligence-gathering operation via a ride-sharing app. “I don't want to stoke the paranoia, but without knowing specifically what 'Gloria' was asking, and indulging in pure speculation—it's not inconceivable that some intel service would commission someone like that to 'find out what you can,' ” he told me. “After all, Aspen that week is ground zero for apparatchiks from government and media—a giant, practically no-holds-barred geeky gabfest. Make no mistake, this would be bargain-basement espionage—really low-end stuff and a sign of either desperation or genius, depending on how it turned out. Kind of a low-end proto-illegal, maybe auditioning or training for the next level.”
But then he, too, caught himself. “Alternatively—and here I'm thinking of some of the NPR-addicted D.C. cab drivers I encounter in D.C.—it could simply be some smart person, well-educated and literate, who's unable to get work in their country of origin and who is genuinely interested and curious for innocent reasons.”
Ned Price, a former CIA analyst who had served as a spokesman for the National Security Council during the Obama administration, echoed those thoughts. “We know any number of foreign governments, even purportedly friendly ones, are collecting intelligence on U.S. soil,” he said. “And we can bet with near certainty that the Security Forum was a target of those efforts. Services would be derelict not to train their focus on the event.” Price, however, was highly skeptical of my spy-spotting abilities. “Those specific efforts are going to be obscured to the naked eye in most cases, and speculating will engender little more than paranoia,” he wrote in an e-mail. “Rather than jump to conclusions about incidents—an Uber driver named 'Gloria,' for example—it's more effective to be prudent about your remarks and conduct generally, ensuring that you're not offering those intelligence services anything they could use.”
Good, I thought. I was just being crazy. I thought back to my days in Moscow where, according to an ex-boyfriend who had served in Israeli intelligence, my circle had definitely had one or two Russian spies. There were people in my Moscow milieu whose stories certainly didn't add up, and close friends and I would often discuss why this or that person may or may not be an FSB agent sent to keep an eye on foreign journalists and businesspeople. But those were the halcyon days when the U.S. and Russia were “resetting” their relationship; as targets, we American journalists weren't as succulent as our Russian colleagues, who were regularly tracked and followed—or worse. The people I thought might be Russian intelligence I just kept at a slight distance, and didn't think much about.
But times had changed. After Russia's invasion of Ukraine and annexation of Crimea, relations with the United States had gone from bad to worse, until the unthinkable happened: Putin tried to elect our president, and in the past week, it seemed more than ever that he had succeeded with Trump's knowledge, if not his direct participation. Suddenly the power of covert intelligence actions seemed limitless.
Later, I called Gloria to see what would happen if I pressed her directly on whether she worked for a foreign intelligence service. "Why? Why you ask that," she said, as she hustled off the phone. "Call me back later, okay?" she said before hanging up.
As McLaughlin had told me of my Gloria mission, “Maybe the fact that the question even arises is a sign of the times.”
On our last night at the conference, Shane and I called an Uber to take us into to town for drinks at a journalist's house. Not totally to our surprise, the driver Uber selected for us was Gloria.
“How aaaaare you?” she sang again as we greeted her.
“So what's going on?” she asked before we'd even closed the car doors. “What are people saying about North Korea?”
“Well,” Shane said, “it seems like people don't really know that much of what's going on there. But you've been to North Korea, right?”
Gloria's heavy silence was interrupted only by the bloop-bloop-bloop of her phone's notification system.
“When did you go to North Korea, Gloria?” Shane asked.
Again, Gloria was silent as her phone screamed on in the cup holder.
“Was it a long time ago?” Shane asked. “Or was it more recent?”
Silence.
“Gloria,” Shane pressed on. “When were you in North Korea?”
“A couple years ago,” she mumbled after a long silence.
“What were you doing there?”
Silence. “I'd like to go back,” she finally said.
Shane, who had also come to see our suspicions of Gloria as silly and paranoid, was now suspicious all over again, as was I. “What were you doing in North Korea, Gloria?” he asked again. “Tell me, Gloria.”
“You know,” Gloria began, finally catching her footing. “You're so cute. I like you. I like you so much. I really do. I like you so, so much. And we can become friends. You can come visit me in Colombia, and we can be good friends. I like you so much.”
She had snatched away the initiative, and here we were anyway, pulling up to the house. “Shane,” she said as he climbed out of the car. “You text me, okay? You text me your name and your last name and your e-mail, and we will stay in touch and be friends, okay?”
We were laughing, but it was that same laughter we'd laughed at the beginning: the uncomfortable laughter of people who don't really know what they're laughing at, or whether they should be laughing at all. What was it that we had encountered? Was Gloria a spy, or were we made paranoid by the surreality of this moment? Or was it a bit of both?
“Gloria!” Shane exclaimed as we headed into the party. “She is up to something! What are you up to, Gloria!”
Julia Ioffe is a GQ correspondent.