President Donald Trump is set to meet with Russian leader Vladimir Putin in Anchorage, Alaska on Friday in what could ultimately be one of the most consequential bilateral conversations of his second term.

Trump’s effort to negotiate an end to the Russia-Ukraine war — which he said on the campaign trail he’d be able to do in one day — has been unsuccessful through his first 200 days in office, though this meeting will be the first time the Russian and U.S. leaders are talking in-person since Trump’s second inauguration.

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Trump and Putin meet for a ‘feel-out’ meeting

The president described their upcoming exchange at Joint Base Elmendorf-Richardson on Monday as a “feel-out meeting” in which he’ll be able to “know exactly whether or not a deal can be made” in the “first two minutes.”

Trump specifically said it’s not his place to make the agreement, rather he will relay the sentiment from Putin to European leaders, including Ukrainian President Volodymyr Zelensky, and give his opinion on Putin’s posture. At the same time, the meeting represents what could be the first major step in the process of ending the war and creating a lasting peace.

“I’m not going to make a deal. It’s not up to me to make a deal,” Trump said on Monday, though he said on Wednesday that there will be “very severe consequences,” if Putin doesn’t appear open to ending the deal.

He also indicated that the U.S. could walk away as a lead mediator if Putin proves unwilling to end the war that’s gone on for three and a half years.

“If it’s a fair deal, I’ll reveal it to the European Union leaders and to the NATO leaders, and also to President Zelensky, I think out of respect, I’ll call him first, and then I’ll call them after, and I may say, lots of luck, keep fighting,” the president said. “Or I may say, we can make a deal.”

The meeting itself will be the first Trump-Putin face-to-face since Trump’s first term. The president has said he’ll be able to read Putin — a former spy for the Committee for State Security better known as the KGB — almost instantly as to whether he’s serious about ending the war.

“I think Putin’s had a very successful run over the years, beginning back in the first term, of using his KGB training to manipulate Trump,” John Bolton, Trump’s former national security adviser, told the Washington Examiner. “But in this case, he had pushed too far. So he needs the meeting to try and work his KGB magic to get Trump back more aligned with him.”

President Trump celebrated Putin coming to the U.S. for the meeting, calling it “very respectful.” It’s Putin’s first trip to the United States in a decade and is his first face-to-face with a U.S. president since before Russia’s full scale invasion of Ukraine, which began in February 2022.

Putin “gets the benefit having been for three and a half years a pariah among international leaders, he’s now going to be on a U.S. military base on U.S. soil, so he’ll be standing next to Trump in the pictures,” Bolton added. “And that’s worth a lot in terms of rehabilitation, and he paid nothing to get it.”

Infamously, Trump agreed with Putin that the Kremlin did not meddle in the 2016 presidential election, disagreeing with the prevailing belief from the U.S. intelligence community, following a one-on-one conversation in the Finnish presidential palace in Helsinki in 2018.

Europe worries about what could go wrong

From Zelensky’s perspective, who was not invited to this meeting, the best-case scenario for him would be for the president to determine immediately that Putin is not serious about ending the war, said Bolton, who also served as U.S. ambassador to the United Nations. Should that happen, it could definitely prove to Trump that Putin is the obstacle to peace, and such a development could aid Zelensky’s efforts to secure continued military support from the Trump administration.

Trump said that ideally, this meeting will be followed by a meeting between Putin and Zelensky, which Trump said he’d be open to attending. If the first meeting goes well, Trump said he would want the next one to happen “almost immediately.”

Alternatively, if Trump is convinced that Putin is willing to make some sort of agreement with significant Ukrainian concessions, it could lead the U.S. president to pressure the Ukrainians to accept the proposal or lose U.S. military and intelligence support.

That concern is shared by other European countries as well.

Trump huddled with Zelensky and many European leaders on Wednesday morning to discuss the president’s upcoming meeting with Putin. Zelensky traveled to Berlin, Germany for it.

The president rated the conversation a perfect 10, while U.K. Prime Minister Keir Starmer praised Trump for opening the door to a negotiated end to the conflict.

World leaders want land concessions off the table

Zelensky has been adamant since the Trump-Putin summit was announced last week that no peace deal can be finalized without Ukrainian input and approval. He has long refused any peace efforts that include sacrificing Ukrainian territory and redrawing the Ukraine-Russia borders in eastern Ukraine.

“There’ll be some land swapping going on,” Trump said. “Russia has occupied a big portion of Ukraine. They’ve occupied some very prime territory. We’re going to try and get some of that territory back for Ukraine.”

Russian officials have also not shown any willingness to give up the Ukrainian territory it occupies. The opposite is true. They are demanding that Ukraine sacrifice land it hasn’t lost on the battlefield yet.

When Russians were at their peak in the war in March 2022, they occupied 26.8% of Ukrainian territory. As of Aug. 11, they occupy an estimated 18.98% of Ukrainian territory, according to the Institute for the Study of War.

Russia has unilaterally annexed four different territories in Ukraine — Donetsk, Luhansk, Zaporizhzia, and Kherson. The Russians carried out referendums they claimed showed those areas voted to join the Russian Federation, but the results were widely viewed internationally as illegitimate.

A major focal point from the European perspective is the idea of security guarantees to ensure that Russia does not agree to pause the war to regroup militarily and restart the fighting at a later date.

The European leaders “know that Putin’s desire is not just to take all of Ukraine, but to rebuild the Russian Empire, which includes parts of NATO, parts of the parts of the EU,” Amb. Kurt Volker, who previously served as the U.S. ambassador to NATO, told the Washington Examiner. “So they are very concerned that if Putin is just appeased in this aggression, he’s going to keep going. And they also know that if there is a cease fire, it’s not a full peace, as you’re not changing Putin’s ambitions.”

There is an unlikely possibility that the two sides could agree to a short-term ceasefire that would allow for time to negotiate a lasting agreement during a cessation of hostilities.

“The ideal thing from a European perspective is that there’s an immediate and full ceasefire, that would be a big success and that would be seen very positively,” Volker added, “but since that’s very unlikely to happen, I think the best thing is that you’re teeing up further discussions that move in that direction.”

Non-Ukraine topics of discussion

Trump has discussed the possibility of strengthening economic penalties on Russia and countries that do business with Moscow because of the support that it provides to the Russian economy.

Trump had given Russia 50 days to agree to a ceasefire last month, and then shortened the time frame to ten days after a series of Russian attacks on Ukrainian cities far from the frontlines. The president said if Russia did not agree to some sort of deal, he would apply “severe tariffs” and possible sanctions and secondary tariffs on Russia’s trading partners.

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The deadline was last Friday and it passed without a specific announcement from the Treasury Department, in light of the summit between Trump and Putin. The administration did double the tariffs on India for purchasing Russian oil.

The U.S. has not implemented similar penalties for China, another major buyer of Russian oil as Washington, D.C., and Beijing continue to negotiate a broader trade deal.

Putin will try to convince Trump not to continue with or strengthen the economic penalties facing Russia.