If our nation’s spies are the infantry of our ideology, as John Le Carré once observed, Tom Sylvester is an unknown soldier who became a four-star general. Two years ago, he was named the CIA’s deputy director of operations, in charge of thousands of officers conducting espionage, covert action, and paramilitary operations. He won the job by virtue of his role in stealing Russia’s war plans for Ukraine, warning the world about the coming invasion, and providing steadfast support to Kyiv’s military and intelligence services. These missions were at the heart of a conversation we had last summer.

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.”

If our nation’s spies are the infantry of our ideology, as John Le Carré once observed, Tom Sylvester is an unknown soldier who became a four-star general. Two years ago, he was named the CIA’s deputy director of operations, in charge of thousands of officers conducting espionage, covert action, and paramilitary operations. He won the job by virtue of his role in stealing Russia’s war plans for Ukraine, warning the world about the coming invasion, and providing steadfast support to Kyiv’s military and intelligence services. These missions were at the heart of a conversation we had last summer.

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

Sylvester, at 60, had the lean and hungry look of a military commando and the dry wit of a hard-bitten war correspondent. His father was a foreign service officer who served in the Saigon embassy during the Vietnam War, at the U.S. mission in Beijing shortly after Mao Zedong died, and as consul general in Shanghai. His grandfather was a vice admiral, his great-grandfather commanded the Navy in the Pacific before World War II, and his great-great-grandfather helped rescue Beijing’s foreign legations during the Boxer Rebellion in 1900. He went to Andover, shook President Ronald Reagan’s hand upon graduating from the U.S. Naval Academy in 1985, and parlayed six years as a SEAL into a career at the CIA, starting out at the Cairo station.

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........

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