ANCHORAGE — The first presidential summit in years between Russia and the United States is on, setting nerves in Europe and Ukraine on a knife’s edge. But President Trump may have a surprise in store for Vladimir Putin.

Efforts to scuttle the high-stakes meeting have not been subtle. European officials issued statements in recent days on the futility of Trump negotiating with Putin over Ukraine without Ukraine, urging the U.S. president on Wednesday to not cut a unilateral deal. Kyiv warned that Moscow’s proposals for peace — rewarding its war of conquest with territorial concessions — are a nonstarter. Many Russia experts are hoping one side simply decides to call it off.

Despite their efforts, the summit — haphazardly scheduled on American soil with days to spare — is moving ahead, with Trump scheduled to host the Russian leader at a U.S. military base in Anchorage on Friday, the first meeting of its kind since 2021.

Experts fear Putin may be laying a trap for the Americans, manipulating Trump in private to solidify Russia’s position on the battlefield. But Trump suggested Wednesday that he would demand Putin agree to a ceasefire in Alaska.

“There will be very severe consequences” if he doesn’t, Trump told reporters.

‘Very grave risk’

Hosting the meeting is an about-face from Trump, who over much of the summer appeared in the throes of a remarkable transformation on Putin, criticizing the Russian leader in harsh terms for the first time. To the relief and delight of Europe, Trump appeared to be losing his patience — embarrassed, even — at Putin’s open refusal to heed his calls for a ceasefire in Ukraine.

But Trump’s threats of a response, increasing sanctions against Russia and its trading partners, lasted only a matter of days.

On Aug. 6, the president’s special envoy on the crisis, Steve Witkoff, a real estate investor with no experience in diplomacy and no background in the region, was dispatched to Moscow. Planning for a summit began within hours of his departure from the Kremlin.

On Tuesday, as White House Press Secretary Karoline Leavitt told reporters that the summit would amount to a “listening session” for Trump on Putin’s interest in peace, battlefield reports emerged of a significant Russian breach in Ukrainian lines.

In a phone call, Ukrainian President Volodymyr Zelensky told Trump that Putin was “bluffing” on his commitments to peace, pressing ahead with an offensive to gain more territory. “There should be joint pressure on Russia, there should be sanctions — and there should be a message that if Russia doesn’t agree to a ceasefire in Alaska, this principle should work,” Zelensky said Wednesday.

“It sure looks like it’s moving in the wrong direction,” John Bolton, Trump’s former national security advisor in his first term, told The Times, dismissing Witkoff as a chief culprit behind what he fears is a coming diplomatic crisis: “Better send the Bobbsey twins.”

The perils of this meeting, Bolton said, lie in Putin’s skills as a manipulator. The Russian president may well convince Trump that his designs on Ukraine are reasonable — and the only way forward.

“There’s a very grave risk it does become an almost take-it-or-leave-it proposition for Zelensky,” Bolton said. On Wednesday morning, Trump criticized the media for being “very unfair” to him for quoting “fired losers and really dumb people like John Bolton.”

Russia invaded the Ukrainian peninsula of Crimea and its eastern regions in 2014, and launched a full-scale invasion of the country in 2022. Nearly a million Russian soldiers have been killed or wounded in pursuit of Vladimir Putin’s war of conquest, according to independent analysts, with hundreds of thousands of Ukrainian soldiers adding to the casualty count.

“Clearly, Trump wants to sit down with the guy that he thinks is his friend again,” Bolton said. “And from Putin’s point of view, he doesn’t want any pesky Europeans around — and particularly not Zelensky. He wants to see if he can correct the damage he did.”

Echoes of Helsinki

President Trump shakes hands with Russian President Vladimir Putin at 2018 Helsinki summit.

(Alexander Zemlianichenko/Associated Press)

Seven years ago, entering a meeting with his Russian counterpart, Trump set a similar bar for success as Leavitt has this week. “I don’t expect anything,” Trump said in an interview at the time from Scotland, before leaving for Helsinki. “I go in with very low expectations.”

On Air Force One en route to Helsinki, he cast himself as a dealmaker and tweeted that, “no matter how well I do at the Summit, if I was given the great city of Moscow as retribution for all of the sins and evils committed by Russia,” it would still not be enough to earn him praise. He repeated the turn of phrase Wednesday morning in his post criticizing Bolton.

“If I got Moscow and Leningrad free,” Trump wrote, “as part of the deal with Russia, the Fake News would say that I made a bad deal!”

What resulted was a meeting and subsequent news conference that produced one of the most notorious moments of Trump’s first term. On the heels of calling the European Union a “foe” of the United States, Trump stood beside Putin and took his side over the U.S. intelligence community, disputing its assessment that Russia had interfered in the 2016 presidential election.

Experts fear that a similar diplomatic rupture could unfold if Trump, deferential to Putin, emerges from their meeting Friday siding with the Russian leader over Ukraine in the war.

In recent days, Trump has said that a deal between the two sides would have to include land “swapping” — territorial concessions that are prohibited by the Ukrainian Constitution without a public vote of support — and that he would give Zelensky the “courtesy” of a call after his meeting with Putin, if all goes well.

“This will be the first U.S.-Russia summit brought about by sheer ignorance and incompetence: The U.S. president and his chosen envoy mistook a Russian demand for a concession,” said Brian Taylor, director of the Moynihan Institute of Global Affairs at Syracuse University.

“Ultimately, this is not a war about this or that piece of territory, but about whether Russia can establish political control over Ukraine, or whether Ukraine will remain free to choose its own domestic and international path,” Taylor said. “Trump’s false suggestion again that Zelensky is somehow at fault for Russia invading Ukraine indicates he still does not understand how we got here or what’s at stake.”

Konstantin Sonin, a professor at the University of Chicago who has been sentenced in absentia to 8½ years in prison in Russia for publishing information on a Russian massacre of Ukrainian civilians at Bucha, said that Trump’s attempts to negotiate away Ukrainian territory could be diplomatically disastrous — but will make little difference on the ground.

“This is not a very popular view, but I am not sure that the U.S. has that much leverage over President Zelensky to force him into major concessions,” Sonin said. “Many European countries would support Ukraine no matter what — even at the cost of their relationship with the U.S. With full withdrawal of the U.S. support, the catastrophic scenario, Ukraine will still be able to fight on.”

Pitfalls for both sides

Kremlinologists tend to believe Putin’s training as a KGB officer at the end of the Cold War gave him unique skills to navigate the world stage.

In Helsinki — as he had so often done with other world leaders, including the queen of England and the pope — Putin kept Trump waiting for half an hour, seen as a move to throw off the U.S. delegation leading up to the meeting.

Last week, in his meeting with Witkoff, the Russian president offered an Order of Lenin to a CIA official whose son died in Ukraine fighting for Russian forces.

Russia watchers fear that Friday will be no different. Already, Putin has secured a meeting with the U.S. president on his own terms.

“Whatever else you think about Putin, he’s an experienced and clever ruler who has successfully manipulated Trump in the past,” Taylor said. “Putin’s intransigence in rejecting Trump’s proposed ceasefire led not to the sanctions that Trump promised to apply last Friday, but an invitation to the United States for a summit at which the U.S. president has already signaled he will endorse territorial changes achieved through military conquest.”

But there may also be pitfalls in store for Putin, experts said.

Trump’s shift in tone on Putin since a NATO summit in The Hague in June suggests it is possible, if unlikely, that Trump is preparing to enter the meeting with a tougher stance. In recent months, the president has seen political benefit in catching world leaders off guard, berating Zelensky and South Africa’s leader in the Oval Office with cameras rolling.

At the North Atlantic Treaty Organization summit, showered in praise by European leaders, Trump said in unusually clear terms that he was with the alliance “all the way.” Days later, he accused Putin of throwing “meaningless … bull—” at him and his team over the Ukraine war.

“I think there is some risk for Putin,” Sonin said. “He is not comfortable in any kind of adversarial situation — he quickly gets angry and defensive. And President Trump has the ability to put people in uncomfortable situations publicly. He has never done this to Putin before, but who knows.”

To Bolton, the best outcome of the summit would be that Putin fails to persuade Trump that he’s seriously interested in peace.

“I don’t think that’s going to happen, but it’s possible,” Bolton said. “I think in the environment that they’ve got, one on one — only Russians and Americans present — that’s ideal for Putin to do his thing.”

“So he’s got what he wants,” Bolton added. “He’s on American soil, with no one else around.”

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Michael Wilner
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