Trump relies on personal diplomacy with Putin. The result is a strategic muddle.

President Donald Trump waits to greet President Vladimir Putin of Russia at Joint Base Elmendorf Richardson in Anchorage, Alaska, Aug. 15, 2025. Nine days after the meeting, all the outward signs are that any real progress has ground to a stop. (Doug Mills/The New York Times)

By David E. Sanger

“Nothing’s going to happen,” President Donald Trump told reporters on Air Force One in mid-May, “until Putin and I get together.”

Trump was making the argument that, for a problem as contentious as the Russian war in Ukraine, the only solution was a meeting of the minds of the leaders of the two superpowers, who could strike deals, knock heads and make it happen.

Now, nine days after that meeting happened at a U.S. air base in Anchorage, Alaska, all the outward signs are that any real progress has ground to a stop. Trump had hinted that President Vladimir Putin of Russia and President Volodymyr Zelenskyy of Ukraine would meet one on one and then together with Trump; neither meeting has been scheduled. “The agenda is not ready at all,” Sergey Lavrov, Russia’s foreign minister, said on NBC on Sunday.

And while Trump insisted to European leaders that Putin had agreed to allow a peacekeeping force inside Ukraine, by midweek the Russians were describing a very different construct, one in which Russia would participate in security guarantees for the country it invaded in February 2022. If ever there was a geopolitical fox-guarding-the-henhouse problem, that seemed to describe it.

On Monday, when asked what the security guarantees would entail, Trump said “we haven’t even discussed the specifics.”

It is all symptomatic of the strategic incoherence of the past 10 days or so. At times, Trump portrays himself as a mediator, someone who can use his influence to extract concessions from Putin, then get Zelenskyy to offer up some land and strike a deal. In other moments, he sounds like an ally of Ukraine, promising to help secure it from future attack. Last week, he wrote a social media post saying Ukraine had “no chance of winning” without being allowed to attack deep inside of Russia, blaming his predecessor, Joe Biden, for not permitting Ukraine to “fight back, only defend.”

After declaring in Anchorage that Putin wants peace, he now admits to doubts, and says he will figure out which side is to blame for failure, if it comes to that. “We’ll know which way I’m going, because I’m going to go one way or the other,” he told reporters Friday.

For Trump, consistency is less important than the trappings of leader-to-leader diplomacy. And he is hardly alone among presidents in believing that his own powers of personal persuasion are the central element of success in U.S. foreign policy — and ending wars. Theodore Roosevelt was convinced of the same, and he brokered an end to the Russo-Japanese war 120 years ago. That conflict ended with the signing of the Treaty of Portsmouth on American soil, and resulted in Roosevelt winning a Nobel Peace Prize, exactly the outcome Trump has not been shy about saying he is seeking.

But so far, at least, this negotiation with Russia is not following the Roosevelt model. Instead, Trump’s session with Putin in Anchorage is beginning to invite comparisons with his face-to-face diplomacy with Kim Jong Un of North Korea seven years ago: friendly, full of handshakes and made-for-TV moments and warm exchanges — Putin sent Trump a photo of their meeting — but not progress. At the end of the day, North Korea gave up not a single nuclear weapon, and has dramatically expanded its nuclear arsenal since.

“Trump went into this meeting with a relatively unified Western position, saying there needed to be a ceasefire first,” said Ivo Daalder, a former U.S. ambassador to NATO who is joining the Belfer Center for Science and International Affairs at Harvard University. “Then, they finally get together, Trump abandons the position and rather than moving the ball forward, he scores a own goal.”

“He said he wouldn’t be happy if there wasn’t a ceasefire, that there would be severe consequences, and there were none,” he added.

Trump said his goal was to “go direct to a Peace Agreement,” he wrote on social media, “which would end the war” because ceasefires “oftentimes do not hold up.”

Trump now says he will know in two weeks whether Putin is serious — the same period of time he gave the Russian leader a few months ago to stop the fighting, a deadline he then ignored. (Two weeks is the standard unit of time for Trump to demand results, whether it is diplomacy or the creation of a new health care plan. Extensions are routine.)

But in the case of Ukraine, Trump always leaves himself an out, saying maybe there will be no peace, and maybe the United States will just have to pull back and let the Ukrainians and the Russians fight it out. Washing his hands of the conflict, declaring he can lead Putin and Zelenskyy to the negotiating table but cannot make them agree, gives him an escape hatch if his negotiations collapse.

But that creates a huge dissonance, an uncertainty about what the U.S. role is in this effort. Sometimes Trump and Vice President JD Vance sound like neutral mediators just trying to bring the sides together — as Roosevelt did — and sometimes they sound as if the United States has strong national interests in making sure that Ukraine remains a free, independent nation.

Trump took the second approach over the past week. He declared that the United States would join European leaders in creating security assurances for Ukraine, though he was quick to add, in interviews, that there would be no U.S. troops on the ground. He said if there were troops they would likely come from “a couple” of countries, including Britain, France and Germany, and the United States might provide intelligence and air support.

But the security assurance essentially means that the United States is committing to come to Ukraine’s defense if Russia attacked again, even if it is not a member of NATO — a move Trump opposes, as did Biden.

But Biden regularly reminded the world that the invasion of Ukraine was illegal, and that if Putin succeeded in Ukraine, it would only be a matter of time before he tried to pick off a NATO member. His Justice and State departments collected evidence of war crimes, for future trials. Trump muddies up who was responsible for the war and has dismantled units tracking war atrocities.

Understandably, the Ukrainians are suspicious: In 1994, they signed the Budapest Memorandum in which the United States, Britain and Russia offered an undefined security assurance, in return for Ukraine giving up the nuclear weapons left on its territory when the Soviet Union collapsed.

Trump said in Anchorage that Putin understood and acquiesced to the Western security guarantees for Ukraine. But by the end of last week the Russians inserted the caveat that they had to be part of the security force, and suggested no NATO nation could keep troops in Ukraine.

On “Meet the Press” on NBC on Sunday, Vance dodged a question about whether Russia could play such a role, saying that “give and take is part of negotiation.” He maintained that the Trump administration had “applied more economic pressure on the Russians to stop this war than Biden did in three years,” a claim Biden’s aides would dispute, given the wide-ranging sanctions on trade, banking, finance and other sectors the United States and its allies imposed after the invasion.

“We are going to eventually be successful or eventually hit a brick wall,” Vance concluded, again portraying Washington as a mediator. As a senator, Vance regularly argued the United States needed to pull back from supporting Ukraine because there was no direct national interest in the outcome.

Daalder said the Trump administration “fundamentally misunderstands” the conflict.

“Trump thinks the conflict is about territory,” he said. But as for the Russians, he said, “it is about identity and the question of whether Ukraine will join the West or effectively be under Russian control.”