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This article is adapted from The Mission: The CIA in the 21st Century by Tim Weiner (Mariner Books, 464 pp., $35, July 2025).

Sylvester had been under cover for 33 years when we sat down in a windowless chamber at CIA headquarters in Langley, Virginia; before we met, no sitting director of the clandestine service had ever given an on-the-record interview, as far as I know. I asked to meet him shortly after he appeared—as “Tom S.”—on a newly created in-house CIA podcast. I had been struck by what he’d said about the power of tyrants to shape the fate of nations: “I’ve had this catbird seat in watching, over the past decades, what has happened in world history. And what continues to horrify me, shock me, is the fact that single individuals have within their power the ability to wreak pain and suffering.”

Sylvester became the CIA’s acting director at the moment President Donald Trump took the oath of office on Jan. 20, serving until Trump’s nominee, John Ratcliffe, a MAGA acolyte, was sworn in three days later. He remained the deputy director of operations until he stepped down in late May.

Looking back on our conversation, I wonder how Sylvester copes with the shattering of the nation’s alliances, what he makes of the amateurs and toadies now in charge of U.S. national security, and if he fears that the chances of a catastrophic intelligence failure are rising as fast as they did at the dawn of the 21st century. The CIA is an executor of U.S. foreign policy; its spies are exquisitely sensitive to orders from on high, and they conduct covert operations under the command of presidents and presidents alone. What do they do when the greatest threat to U.S. national security is the man in the White House?

Officers stand guard outside the George Bush Center for Intelligence in Langley, Virginia, in July 2022. Tom Brenner/The New York Times via Redux Pictures

After 9/11, he led a largely successful mission to penetrate Saddam Hussein’s military and intelligence services before the U.S. attack on Baghdad and then served as station chief in Damascus in 2005 and 2006. He spent the next decade running covert operations throughout the Middle East.

In the summer of 2017, Sylvester received new marching orders from Tomas Rakusan, the new chief of the clandestine service, whose identity remained a state secret until after his retirement. Rakusan had spied on Russia since before the end of the Cold War, operating throughout Central and Eastern Europe. His hatred of the Russians was bred in the bone. His parents were Czech; he was 9 years old when Soviet troops crushed the Prague Spring uprising in 1968. Rakusan saw Russian President Vladimir Putin’s subversion of the presidential election on Trump’s behalf as the espionage equivalent of 9/11. In retaliation, he aimed to penetrate the Kremlin—among the greatest aspirations of the CIA since its foundation, and a goal never achieved.

Rakusan vowed a gut renovation of the CIA’s Russia House, established early in the Cold War to gather intelligence on the Soviet Union and run covert operations to undermine Soviet influence around the world. He began by bringing in scores of senior counterterrorism officers—including Sylvester, one of his favorite officers. “The Russians manipulated our fucking elections,” he told them. “How do we make sure this never happens again?” He didn’t care if they didn’t speak Russian or had never set foot in Moscow. He ordered them to take their expertise in targeting and recruiting terrorists and turn it against Russian spies, diplomats, and oligarchs. The goal was to obtain intelligence on the intentions of the Russian leader and his inner circle through espionage.

Rakusan enlisted the electronic eavesdroppers at the National Security Agency (NSA) and the counterintelligence forces of the FBI. He asked the leaders of the congressional intelligence and armed services committees for help. How much money do you need? they asked. They delivered tens of millions of dollars, and Rakusan doubled the size of Russia House in less than two years.

“What he had done was to reimagine, and get us out of, a paradigm where we’re stuck in the early Cold War,” Sylvester said. “The heart of the issue was the concrete decisions by which to ensure that we would put daylight into Russia House,” long the most cloistered part of the CIA. Its conference center at headquarters was decorated with Soviet propaganda posters depicting muscular peasants and handsome soldiers. One-third of Russia House was a back room where operators and analysts had toiled throughout their careers in the greatest secrecy; the nature of their work had not changed fundamentally since Winston Churchill called Joseph Stalin’s Russia a riddle wrapped in a mystery inside an enigma. They guarded and hoarded intelligence reaped through years of painstaking operations, reluctant to share their secrets with outsiders, and everyone was an outsider. They were proud to the point of arrogance. To their shame, they had failed to see the Kremlin’s covert support for Trump’s election until it was too late.

Rakusan ordered the old guard in the back room to unseal their secret files, sanitize them to protect sources and methods, and share them with the rest of the clandestine service—and, more importantly, its allies overseas. In the past, those secrets always had been deemed too sensitive. That all changed, and the result was revolutionary. The call to arms marked the return of espionage to its traditional place of preeminence at the CIA after 16 years in the shadow of counterterrorism, counterinsurgency, and their attendant horrors. (“We were focused on that, and China and Russia were focused on us,” former CIA Deputy Director Mike Morell said.) The CIA had failed to deduce the military intentions of the Russians during the Cold War. Now its spies were starting to peer inside the Kremlin, and divining secrets only espionage could reveal.

By the summer of 2020, CIA officers were working in close liaison with the British, Dutch, Ukrainians, Poles, Czechs, Estonians, and many other services against the Russians. “There was the strategic decision on how we would share intelligence,” Sylvester said. “We used it as an influence mechanism, in and of itself, to get governments to start cooperating with us.” This hard-won trust “allowed them to open up taps of cooperation and intelligence that they had theretofore not shared with us,” he added. The CIA and its foreign allies were cross-fertilizing intelligence, choreographing operations, and, most importantly, recruiting Russian sources.

CIA Director William Burns prepares to testify before the Senate Select Committee on Intelligence about global threats against the United States on March 11, 2024. Chip Somodevilla/Getty Images

The CIA had been able to “push back against the Russian services” largely by “working with liaison partners overseas to expose and disrupt Russian intelligence activities,” then-CIA Director William Burns told me last year. “And then what we tried to build on that, starting in the spring of 2021, was the recruitment dimension of this,” he said. “This was really, especially once the war drums started beating, a once-in-a-generation opportunity, given the disaffection in some parts of the Russian elite and Russian society” against Putin’s regime.

Sylvester took charge of the call to arms against the Kremlin as the CIA’s new operations chief for Europe and Eurasia in the spring of 2021. That October, five weeks after Kabul fell to the Taliban, he foresaw that Russia was preparing to invade Ukraine. No eureka moment, no flash of insight, no single source had led to this revelation. Many streams of intelligence, flowing through myriad channels, had become a mighty river. The CIA, riding that current, had arrived at the conclusion that Putin was going to war.

Kyiv’s spy services, rebuilt by the CIA after Putin seized Crimea and other parts of eastern Ukraine in 2014, had become one of Washington’s best sources of intelligence on the Russians; the CIA was becoming the Ukrainians’ best defense against them. “It was probably one of the best investments that the CIA, the U.S. government, has made,” Sylvester said; it had created “the trust, the confidence, the ability in times of need to feel like you were in the trenches together.” By the fall of 2021, the CIA had given the Ukrainians a graduate course in espionage and paramilitary operations, along with the ability to understand and utilize a steady stream of U.S. intelligence.

“If you ask me the two biggest factors” that have allowed Ukraine to hold out against Russia, Sylvester said, “one was the decisions in 2014 onwards to invest, put in people and money, and training continuously, all the way up to the war. And second was this ongoing decision on the intelligence sharing and the repeated travel by our director all over Europe” in advance of the invasion.

Ukrainian soldiers stand in a field where they dug trenches in Donetsk oblast, Ukraine, on Jan. 10, 2023.Viktor Fridshon/Global Images Ukraine via Getty Images

Burns said the CIA had to go public with its knowledge that Russia was preparing to invade, and Biden approved. Many European political leaders were skeptical; the stench of the CIA’s bogus reporting on Saddam’s arsenal still lingered. But when the foresight proved precise, Sylvester said, the effect was electric: “The fact that we shared accurate information with many, many of our partners that accurately predicted the fact that Russia came into the war, they told us, was the most powerful thing the CIA had done with them and for them for the last 18 years.”

Sylvester called the survival of Ukraine a triumph of HUMINT: human intelligence, the heart and soul of espionage. The term was coined in the 1950s to distinguish the work of human spies from SIGINT, signals intelligence collected by the newborn NSA, and IMINT, imagery obtained by the U-2 plane and photoreconnaissance satellites. These technologies “threatened to change the character of our work,” former CIA Director Richard Helms warned in 1983. “The collectors with technical gadgets began to disparage the work of human collectors. The new cry from the gadgeteers was, ‘Give us the money and leave it to us.’ And, indeed, why take risks running spies when gadgets would tell you what you wanted to know? But therein lay a fallacy. … Because gadgets cannot divine man’s intentions.”

“If there is a weakness in our intelligence apparatus,” Helms had concluded, “it is in our ability to figure out what the leaders of a foreign power are going to do in any given situation.”

All this remains true. If the CIA has 10 analysts studying the transcript of an intercepted conversation, “they’re going to come to 10 different analytic assessments on what happened,” Sylvester said. But if you speak with someone who was in the room, you might know the truth, or something close to it. “When we talk about human intelligence, it really is the collection of everything that goes into how our adversaries are thinking, acting, and the context in which those decisions are being made,” he said. The people the CIA had recruited to penetrate the Kremlin “are not case numbers. … They’re human beings who’ve decided to make some incredibly bold and courageous things to try and change the world around them.”

Washington’s ability to warn of the Russian invasion and blunt its force rested “on espionage, human intelligence, the collection of insights from people to effect policy,” Sylvester said. So did the CIA’s decade of covert support for Ukraine. That mission depended on the ability “to build up human relations” with its military and intelligence officers. “Is that espionage? Absolutely. That’s what HUMINT is,” he said. “And I think this should be so revelatory.”

The thought that a humanity lay at the heart of espionage clashes with the perception that spying is at worst immoral to the core. Both things are true. The director of the CIA’s boot camp during the Cold War, Hugh Cunningham, told two generations of young trainees: “We must have the greatest immorality, and we must have the greatest morality.” The alliance between a CIA officer and a foreign recruit was an alloy of trust and betrayal, founded in the agent’s faith in the United States and his choice to commit treason.

U.S. President Donald Trump speaks at CIA headquarters on Jan. 21, 2017. Olivier Doulier/Getty Images

In the past few months, Trump has called Ukrainian President Volodymyr Zelensky a dictator, accused him of starting the war in Ukraine, and tried to shove a cease-fire on Russia’s terms down his throat. Trump cut off the flow of U.S. intelligence to Kyiv on March 5 and kept the spigot shut for a week as Ukrainian forces reeled and retreated. His support for Russia’s war aims was a bitter betrayal and not only of Ukraine. The CIA’s officers had been fighting the Kremlin ever since the agency’s creation in 1947. They depend mightily on secret liaisons with scores of foreign intelligence services; they cannot think globally without that help. Now Trump has made U.S. allies wary of sharing secrets with Washington. This bodes ill for officers and analysts trying to peer over the horizon to see what’s coming.

Trump has been implacably hostile to the CIA ever since its unassailable assessment that Russia worked to elect him in 2016. He sees it as the capital of the “deep state,” that imaginary cryptocracy of spies and soldiers working in secret to undermine his presidency. In the weeks before the Jan. 6, 2021, insurrection at the Capitol, he had come to believe that Gina Haspel, then his CIA director, had been part of a plot to rig the presidential vote against him. Trump tried to keelhaul Haspel, but she stood up to him and protected the agency from his wrath.

Ratcliffe has failed to do so at every turn. He has fired new CIA hires, targeted senior officers for early retirement, twisted intelligence to please the president, and overseen an ideological purge. In March, Sylvester and his colleagues nominated a recently retired officer to succeed him: Ralph Goff, a six-time station chief who had been deeply involved in Russian and Ukrainian operations. As a civilian, Goff had voiced the strongest support for Kyiv. That same day, Laura Loomer, a far-right saboteur beloved by Trump, went to the Oval Office and handed him a long list of intelligence and national security officials whom she deemed denizens of the deep state. The White House blocked Goff’s nomination within hours.

With Ratcliffe in charge at the CIA, the MAGA warrior Kash Patel running the FBI, the conspiracy theorist Tulsi Gabbard overseeing national intelligence, and the Christian-nationalist Pete Hegseth at the Pentagon, Trump has created the makings of a national security nightmare. “Totalitarianism in power invariably replaces all first-rate talents, regardless of their sympathies, with those crackpots and fools whose lack of intelligence and creativity is still the best guarantee of their loyalty,” Hannah Arendt observed decades ago.

“The world is getting increasingly complex and increasingly dangerous,” Sylvester said last year. “Across the globe our adversaries are doing everything they can” to instill authoritarian rule. Russia and China depended on “other countries that fear their dominion, fear their tyranny, and only cooperate from a sense of either intimidation, or that it’s business, or they’re bought off.” But he asserted confidently that the United States had allies around the world who “identify with us and what we want to do in this globe.” Who sides with it now as it lurches toward autocracy?

Over the course of eight decades, the CIA’s officers saw themselves as a secret army in the battle for what once was known as the free world. Now the country faces a threat from within. As the president assaults civil liberties and the Constitution, the instruments of U.S. national security are in the hands of his sycophants. The foundations of its foreign policy are crumbling. The ranks of the CIA’s most experienced spies and analysts are thinning. Its ties to foreign services are fraying. All this raises the danger of a disastrous intelligence failure. Imagine what could happen if the United States were struck again by a surprise attack in the coming days. What would stop Trump from declaring martial law, suspending elections, and truly ruling as a dictator?

Presidents before Trump have used the CIA to try to realize their imperial ambitions. And the nation’s spies do not have a history of defying presidents. But perhaps those with the greatest morality will resist him. And years could pass before their stories might be told.