The Separation: Inside the Unraveling U.S.-Ukraine Partnership

The Russians

The Americans might have been comfortable bullying the Ukrainians. But to get Mr. Putin to play, they felt they needed a softer approach.

At the first negotiating session, in February in Riyadh, Mr. Rubio had sought to break the ice. He channeled his inner Brando.

Sitting across from the foreign minister, Sergei Lavrov, and the close Putin aide Yuri Ushakov, he offered his rendition of the scene from “The Godfather” in which Vito Corleone counsels his son about threats from rival crime families and tells him: “I spend my life trying not to be careless. Women and children can be careless, but not men.” Nuclear powers, Mr. Rubio explained, need to communicate.

Even the characteristically scowling Mr. Lavrov broke a smile.

From the beginning, Mr. Trump’s advisers had judged that Mr. Putin had two options:

Fight on, at great cost — in battlefield dead, in economic havoc, in damage to his relationship with the American president.

Or cut a deal, laden with what Mr. Waltz touted to the Russians as “all of this upside”: an easing of sanctions, a new era of business cooperation — even an end to exile from the group of leading industrialized nations.

What made Mr. Trump confident about the upside was his belief in a personal connection to Mr. Putin. Returning from Moscow, Mr. Witkoff would gush about the Russian’s “huge respect” for the president. But there was more than that: For the first time in years, Mr. Trump’s aides told themselves, an American president and many top advisers were courting the Russians, listening with sympathetic ears. Surely Mr. Putin would see value there.

Yet it was not quite so simple. Mr. Witkoff may have been plying his back channel with Mr. Dmitriev. But the official negotiations would be conducted by two very different Russians, seasoned diplomats with a more orthodox adherence to geopolitical grievances and rivalries.

Mr. Lavrov was a nationalist hard-liner vehemently opposed to concessions to end the war; he spoke ominously about “solving the Ukraine problem once and for all.” Mr. Ushakov came across as more open. Yet he, too, spoke frequently about the war’s “root causes” — Kremlin shorthand for Mr. Putin’s bitterness over his country’s diminished post-Soviet world stature.

This front-channel, back-channel tension flared in the episode of the chairs.

At the February talks in Riyadh, Mr. Rubio, Mr. Waltz and Mr. Witkoff had taken their seats opposite Mr. Lavrov and Mr. Ushakov. The third chair, Mr. Dmitriev’s, was empty. “We want to wait for him?” a puzzled Mr. Rubio asked. “No,” Mr. Lavrov responded, and the chair was moved to the back of the room.

When the second session began, there were three chairs on the Russian side, and Mr. Dmitriev was in the room. According to two U.S. officials who were present, Mr. Lavrov moved the chair back to the rear, only to have Mr. Dmitriev retrieve it, sit down and later extol the economic benefits of a peace deal. (A spokeswoman for Mr. Dmitriev said the American account of the episode was “completely not true,” adding, “The meeting was always preplanned and structured with clearly defined political and economic segments.”)

If all of this bred uncertainty about where Mr. Putin stood, the hard-liners sought to put it to rest. To understand Mr. Putin’s negotiating position, they told the Americans, they should refer to his June 2024 speech to the Ministry of Foreign Affairs: Mr. Putin would not end the war until he fulfilled his territorial ambitions — complete control of the four oblasts in Ukraine’s east.

At that moment, in three of them, Russia controlled less than three-quarters of the territory. Mr. Trump could force the Ukrainians to abandon the rest, or the Russians would fight on.

Mr. Putin, the hard-liners seemed to be saying, wasn’t terribly keen on the Americans’ upside.

Once they had maneuvered the Ukrainians into the box, the Americans hoped to persuade the Russians to make concessions of their own. Wouldn’t Mr. Putin want to stay on Mr. Trump’s good side?

A week after Jeddah, Mr. Trump called Mr. Putin and asked him to accept the cease-fire. But the Russian would only agree to negotiate a narrow pause — of strikes on energy infrastructure.

To Mr. Trump’s advisers, perhaps the problem was less the incentives than skepticism that the president would deliver. “Today, Trump says one thing; tomorrow, who knows?” a senior European official recalls Mr. Lavrov saying. During his first presidency, after all, Mr. Trump had spoken about warming relations only to have Russia hawks in key national security posts double down with more adversarial policies.

Now, preparing for a second round of talks in Riyadh in late March, the Americans sought to show that this time would be different. They sent representatives who had been prominent critics of the Biden administration’s support for Ukraine — Michael Anton, the State Department’s head of policy planning, and Mr. Hegseth’s aide Mr. Caldwell. “A lot of people you don’t like are not here,” Mr. Anton told the Russians in Riyadh.

The Americans hoped to parlay the freeze on energy strikes into the broad cease-fire that the Ukrainians had accepted in Jeddah. But the talks would end where they had begun, with the Russians agreeing only to freeze energy strikes for 30 days.

Mr. Witkoff remained an optimist. “Steve says, ‘It’s always going great,’” a senior U.S. official said. Yet however much the president’s advisers wanted to believe in Mr. Dmitriev, many still couldn’t. Some, too, harbored misgivings about Mr. Witkoff. They were reluctant to speak up because of his friendship with the president, but they noticed how Mr. Witkoff sometimes seemed to lack an understanding of Ukraine’s geography and its strategic implications.

There was also his insistence on meeting alone with Mr. Putin and his aides; some American officials worried that would leave the diplomatically inexperienced Mr. Witkoff open to manipulation. At the first meeting, he was not accompanied by a U.S. government translator; while he did take one to subsequent meetings, he would not bring a note taker.

“He felt like Putin had invited him, and that he had this level of rapport with Putin,” an official explained. Mr. Witkoff told colleagues, “I’m a trained lawyer — I was the note taker.”

Over the next three months, Mr. Witkoff and Mr. Dmitriev tried to move the needle. The two men privately discussed possible new concessions to Mr. Putin that went far beyond those presented to the Ukrainians. Mr. Witkoff smoothed the way for Mr. Dmitriev’s brief April visit to Washington, bearing what the Russian touted as new proposals for consideration.

The meetings were held at Mr. Witkoff’s house in the Kalorama neighborhood, and to promote Mr. Dmitriev’s credibility, Mr. Witkoff invited Mr. Rubio and a group of senators to dinner on the night of April 2.

Among the senators was Richard Blumenthal, a Connecticut Democrat and outspoken Ukraine supporter. He had accepted the invitation, he recalled, with “mixed feelings” about “having this very elegant meal with a guy who is one of Putin’s henchmen.” He added, “I was a little put off by the friendliness, the chumminess, the coziness between him and Witkoff.”

At the dinner, Mr. Blumenthal said, he confronted Mr. Dmitriev, “as politely and courteously as possible.”

“I didn’t say, ‘You have blood on your hands,’” he recalled. “But I basically said, ‘We hope you will come to the table because Russia here is the aggressor, and people are dying.’”

One Trump adviser said the dinner was a way to pass a message to Mr. Putin through Mr. Dmitriev: “We have a lot of political obstacles here. This is what I heard here. Here are the political realities in Washington.”

It was amid the hope against hope in negotiations that Mr. Hegseth’s acrimony toward General Cavoli erupted.

The morning after the Dmitriev dinner party, the CNN correspondent Natasha Bertrand posted a message on X quoting the general’s remarks to a Senate committee that Russia constituted a “chronic” and “growing” threat. Aides forwarded the post to Mr. Hegseth as evidence that the general was undercutting efforts to win over Mr. Putin. “Fire Cavoli,” Mr. Hegseth barked to his chief of staff, Mr. Kasper, according to officials briefed on the conversation. General Cavoli would have become one of the at least two dozen top military officers purged by the defense secretary had Mr. Kasper not pointed out that a European general would have temporarily overseen U.S. nuclear forces in Europe.

On April 8, the general appeared before a House committee. First, though, a Caldwell ally at the Pentagon, Katherine Thompson, testified that “contours of a lasting peace are coming into view,” that an initial cease-fire — presumably the freeze on energy strikes — was taking hold.

Then General Cavoli spoke and, apparently unaware how close he had just come to being fired, repeated his warning about the Russian threat. This time the secretary called him and, according to an official briefed on the conversation, told him that by his “words, demeanor and testimony” he was undermining the president. What had he said? the general asked. “It’s not what you said necessarily; it’s what you didn’t say,” the secretary responded. “You didn’t say cease-fire, you didn’t say peace, you didn’t say negotiations.”

In fact, that initial cease-fire was holding only in the slimmest sense, with each side accusing the other of violations. Ukraine agreed to extend the pause; Russia refused.

Even Mr. Trump had to ask, “Does Putin really want a deal, or does he want all of Ukraine?” The president, one aide said, was beginning to suspect that he had “completely overestimated” his ability to charm Mr. Putin. A few weeks later, a senior European official spoke with Mr. Putin. Mr. Zelensky had conceded so much; Mr. Trump had offered so much. “If you ask me, Trump’s position is very close to your position,” he told the Russian president. “Why don’t you agree to a cease-fire and get the Americans to lift the sanctions?”

“We want to get peace,” Mr. Putin responded, and then reiterated his maximalist demands: Not only did he want all of the contested territory; he wanted the Americans and Europeans to recognize the legitimacy of his claims.

The European official later pressed Mr. Witkoff to take more initiative to bring Mr. Putin to the table. Mr. Witkoff’s message was: “We have tried every imaginable idea. And none of it was working. And we’d gotten to this place that, maybe, they just needed to fight it out.”