In the Magazine Analysis

Donald Trump, Russia and Why the President Would Make a Terrible Spy

Donald Trump
President Donald Trump on the South Lawn of the White House upon his return to Washington, D.C., on August 20, after a vacation in Bedminster, New Jersey. Yuri Gripas/Reuters

“Are you fucking kidding me?”

It was the summer of 2008, and I was in Wayne, New Jersey, standing in a Hooters parking lot with Captain Oleg Kulikov, a New York–based Russian spymaster. For three years, I’d been working for Moscow, trying to prove my worth. I wanted to become a key asset for the GRU, Russia’s military intelligence agency. In return, I wanted a hefty paycheck and thought I’d done enough to earn it. But Kulikov was dithering—and he could see I was upset.  

What he didn’t know: I was a double agent, working for the FBI. My mission was to make the Russians believe I was a spy. Which meant I had to show Kulikov that I was tired of his games and willing to walk away.

I’ve thought of this moment several times since Donald Trump won the 2016 presidential election. Many have speculated that Trump is a Russian asset— perhaps a longtime one. His ties to ex-Soviet oligarchs are certainly troubling; some allege he’s allowed the Russian mob to launder big money through his properties (the Kremlin reportedly has extensive links to organized crime). His remarks about Moscow are equally troubling. He has defended the Kremlin’s killing of dissidents (“Do you think our country is so innocent?”) and dismissed claims by his own intelligence services that Russian-backed hackers carried out a plot to undermine his opponent—and American democracy—in November.

Today, as a special counsel and others investigate ties between the president’s campaign and Moscow, Trump has dismissed these probes as “fake news” and a “witch hunt.” His assertions are false and self-serving.

Yet from my years of being a double agent, it’s also evident that the brash New York real estate mogul would have made a terrible spy. Becoming a foreign asset is a one-sided relationship; the handlers have all the leverage. Being a willing participant is not enough. Intelligence services carefully study their recruits, gauging their suitability for spycraft. “The Russians pitch a lot of people,” says Scott Olson, a recently retired counterintelligence senior FBI agent, “but for a host of reasons, those people don’t always make the cut.”

As a double agent, I spent most of my time convincing my handlers I was not an FBI plant—and that I was trustworthy. Those two things may sound the same, but they aren’t. The Russians were interested in the intelligence I could provide. And they were constantly making sure they could depend on me, as well as keep me under control. They had to trust what I delivered but also that I would follow directions.

It is often assumed that lying is synonymous with spying, but that is not the case, says Emily Brandwin, a former CIA case officer: “At the CIA, we'd always say, ‘Don't case officer a case officer’.... You can B.S. everyone else, but you don't B.S. your colleagues.” It was the same thing with my Russian handlers; my work for the FBI aside, lying wasn’t really an option. The Russians routinely asked me questions they had asked months before to see if my answers changed. No matter how insignificant the details, there could be no deviation, because if Oleg couldn't trust me about the small things, how could he trust me about the big things?  

Of course, over three-plus years, my Russian handler wasn’t able to watch me all the time or verify how I received the intelligence I gave him. I once handed him a stack of fighter plane manuals that I had “borrowed” from a defense contractor. When I presented these materials to the Russians (which was illegal), they never suspected the FBI’s involvement. My handler believed me because I had earned his trust.

The issue of trust is even more important when somebody is a “high-visibility” asset, such as a lawmaker. “Politicians are malleable,” says a former American senior intelligence officer, who served undercover and asked to be called only “Logan” to protect U.S. intelligence sources and operations. “We would weigh what they say privately much more than what they say publicly.”

Enter Trump, a politician whose public and private persona seem to be one in the same. From his inflammatory comments about the violence in Charlottesville, Virginia, to his tweets trashing Attorney General Jeff Sessions, the president appears to think, speak and act on impulse, with little restraint.

He also has a long history of lies. Just ask The New York Times. The paper has compiled an up-to-date list of his breathless falsehoods, from the crowd size at his inauguration (it wasn’t the largest in presidential history) to his claim that the Department of Justice signed a “watered-down” travel ban ( he signed it). Enlisting him as an asset would be a “nightmare,” says John Sipher, a 27-year veteran of the CIA’s national clandestine service with multiple overseas tours as chief of station and deputy chief of station. “Agent handlers are looking for spies that can...protect the secrecy of the relationship.”

True. But as the Republican presidential candidate, Trump would still have been a tempting target. Plus, as Sipher points out, the reality TV star “oozes the two top traits that recruiters are looking for: an unhealthy ego and over-the-top greed.” Would those attributes, coupled with his position, have negated his obvious risk as an asset? That’s unclear.

What is clear, however, is that the Russia probe has uncovered some suspicious behavior from Trump surrogates such as Paul Manafort, Michael Flynn and Jared Kushner. All have ties to Moscow that predate the election: Flynn accepted money to appear at a gala for RT, a state-controlled Russian television station; Kushner has socialized with Roman Abramovich, an influential Russian billionaire; and Manafort made a fortune working for the party of Viktor Yanukovych, the former president of Ukraine, now a guest of Russian President Vladimir Putin living in Russia.

Because of these connections and others—and because of Trump’s impulsive personality and history of mendacity—it’s reasonable to assume that Moscow may have avoided direct contact with the GOP candidate in favor of working through surrogates.

Back in that Hooters parking lot, Kulikov and I stared at each other for a long, tense moment. The Russian spymaster weighed his options. He had spent years trying to cultivate me, knowing that if my access to U.S. government information grew, so would his. Suddenly, a smile spread across his face, and he assured me that more money would be coming my way. He invited me inside for wings and beer—a sign that I had passed his test and officially become a trusted Russian asset.

Or so he thought.

Naveed Jamali is the author of How to Catch a Russian Spy , a memoir about working undercover as a double agent for the FBI. He continues to serve as an intelligence officer in the United States Navy Reserve and a senior fellow in the Program on National Security at the Foreign Policy Research Institute.

Join the Discussion