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Vladimir Putin is coming to America. Despite the international warrant for the Russian president’s arrest, despite his years of hostile threats against NATO, and despite him showing no remorse for his invasion of a sovereign nation.
None of that matters to President Donald Trump, who announced Friday night that he would meet the globally shunned leader this Friday in Alaska. What does matter to Trump is that he may be able to stop the bloodshed in Ukraine, the worst European conflict since World War II, fulfilling one of his biggest campaign promises.
Many of Washington’s European allies, Ukraine included, now worry that the Art of the Deal president could propose a solution to this conflict that makes concessions to the aggressor, including and especially a redrawing of Ukraine’s borders, when he sits with Putin. Putin has made no commitments to cede territory or scale back Russia’s aggressive military campaign, and he has long claimed that Ukraine does not exist. Ukrainian President Volodymyr Zelensky, in a video message yesterday, angrily condemned the notion that Trump and Putin alone could decide Ukraine’s future. “Any decisions made against us, any decisions made without Ukraine, are at the same time decisions against peace,” he said.
Trump, who has grown frustrated in recent weeks with Putin’s lack of enthusiasm for compromise, had set a deadline for Russia to come to the negotiating table or risk increased tariffs and other punitive measures. He even threatened to move nuclear-armed submarines closer to Russia, and vowed to punish India—one of the largest buyers of Russian oil—for helping bankroll Moscow’s energy sector.
Trump had promised to end the conflict before even stepping foot inside the White House. As months passed with no deal, Trump finally came to believe that Putin was to blame.
But signs that an end to hostilities between Ukraine and Russia was remotely plausible came the day after Trump’s envoy to the Middle East (and beyond), Steve Witkoff, returned early this month from Israel. Through back-channel discussions with a close Putin ally, Witkoff—the real-estate executive who, like Trump, is more dealmaker than diplomat—received word of the Russian leader’s new willingness to discuss ways to end the fighting.
Witkoff had reason to believe that talks were in the making, but he did not want to discuss the details over the phone, according to two people who spoke on the condition of anonymity because the discussions weren’t public. After giving his pilot a night off in Miami, Witkoff shuttled back to Washington to brief Trump, Vice President J. D. Vance, Secretary of State Marco Rubio, and White House Chief of Staff Susie Wiles on what he learned, before heading to Moscow last week to get a face-to-face guarantee from Putin that he would attend an in-person meeting in good faith. “We are not going to send Donald Trump there if it’s not perfect,” a top Trump adviser told us. By Wednesday, Trump and Witkoff looped in European allies, including Zelensky, on Witkoff’s meeting and their plans to get Trump and Putin in a room together.
[Read: Trump’s real secretary of state]
Trump is open to including Zelensky in the Alaska talks this week, a White House official told us. But for now, at Putin’s request, the Ukrainian leader has not received an invite. “The President hopes to meet with Putin and Zelensky in the future to finally bring this conflict to an end,” White House deputy press secretary Anna Kelly told us in a statement.
Zelensky’s resistance risks provoking the ire of Trump, who often hails himself as a peacemaker in a world that, in his telling, had plunged into warfare and chaos during Joe Biden’s presidency. There is real worry in Kyiv and Europe about the deal Trump may strike, especially as public opinion about U.S. assistance to Ukraine continues to sour, particularly among Republicans. At most, European and U.S. officials believe that Trump may walk away with some flimsy guarantees to freeze the conflict—meaning that Ukrainian territory captured by Russia since February 2022 will stay in Russian hands.
That, according to Zelensky, is a nonstarter.
Trump has disliked Zelensky dating back to their “perfect call” in 2019 that ultimately led to his first impeachment, and he views Ukraine as undeserving of U.S. support. Trump also remains skeptical of the traditional transatlantic alliances prized by his predecessors, and he routinely calls out Europe for failing to share more of the burden regarding NATO’s collective-defense agreement.
Trump’s skepticism of Ukraine was shaped even before he became president, when, in the thick of the 2016 election, the country’s anti-corruption agency released information alleging payments to his campaign manager at the time, Paul Manafort. In White House meetings and talks with foreign leaders during his first term, Trump repeatedly described Ukraine as “totally corrupt” and full of “terrible people.” Trump has even repeated Kremlin talking points that Ukraine is to blame for the war.
Trump has long believed that he and Putin share a special rapport. Allies say he felt that the two survived the “Russia, Russia, Russia hoax” together, and that Putin would respect his historic political comeback. Trump has been deferential to his Russian counterpart, fueling speculation about the true nature of their relationship in global capitals since his first term in office.
At their introductory meeting in Germany, in 2017, Putin urged Trump to recognize Russia’s claim of sovereignty over part of Ukraine, citing links dating to an 11th-century political federation located in modern-day Ukraine, Belarus, and part of Russia. Former officials with direct knowledge of the meeting said Trump listened intently to Putin’s soft-spoken argument against Ukrainian sovereignty.
But Putin, a shrewd former Russian-intelligence officer, has never quite returned the affection. He openly admitted, when asked during the leaders’ 2018 Helsinki summit, that he had hoped Trump would win the election two years prior, although he never owned up to interfering in the contest on the Republican candidate’s behalf. He has been at times cool to Trump in recent months, including being slow to congratulate him on his election.
[Read: How Putin humiliated Trump]
Administration officials like to note the state of play when Trump took office the second time, emphasizing how much the U.S.-Russia relationship has deteriorated since February 2022, with Putin isolated from much of the Western world, particularly after the International Criminal Court issued a warrant for his arrest in connection with the war in Ukraine (the U.S. is not a party to the Rome Statute of the ICC). Witkoff, officials say, has largely been responsible for restoring those direct lines—something you want intact when dealing with two of the world’s biggest nuclear powers. Witkoff “speaks directly for the president,” one person said. “Trump is a chameleon, but when it comes to Witkoff, the two are in lockstep.”
Trump has many people he calls friends, but few like Witkoff; the men have the same background in New York real estate and made a point of not abandoning the president during his months of political exile after he left office, in 2021.
A person familiar with the White House discussions said the members of the small senior national-security team supporting Trump all bring different perspectives to the peace talks. Vance has long been a skeptic of U.S. involvement in Ukraine. Rubio has taken a more hawkish approach to Russia. Witkoff and Trump consider themselves dealmakers, often speaking with each other in front of the others in a language the others don’t speak, the person said. Still, Trump came into office believing that he could quickly deliver a cease-fire. For months, he generally sided with Moscow in its war against Ukraine, absolving Russia for having started the conflict and threatening to abandon Kyiv as it mounted a desperate defense. He upbraided Zelensky in the Oval Office, in February, and briefly stopped sharing intelligence with Ukraine. He believed that he could, in addition to working with his Russian counterpart to end the war, reset relations and forge new economic ties between the two countries. He even envisioned a grand summit to announce a peace deal.
But Putin rejected repeated American calls to stop his attacks. And Trump, in recent months, began to take that personally, complaining privately to advisers—and then eventually in public—that Putin would tell him one thing in their phone calls (that he was committed to peace) and then act entirely differently afterward (by bombing Ukraine).
Putin only ratcheted up his attacks as the weather warmed and Russia began a renewed summer offensive. Some aides close to Trump came to believe that Putin would signal a willingness to negotiate—including agreeing to some low-level meetings with the Ukrainians in Turkey this spring—in order to buy time to continue his offensive.
Trump’s recent sanctions threat played a role in pushing Putin back toward negotiations, aides believe. The president imposed some steep secondary sanctions on India but held off on punishing other nations that do business with Moscow—namely, China—and he did not sanction Russia directly by Friday’s deadline, giving Putin more time to negotiate.
[Read: Is Trump falling out of love with Putin?]
Still, the president had remained intrigued by the thought of a summit’s made-for-TV spectacle. When the idea resurfaced last week, Trump first said that he wanted an initial meeting with Putin, followed by a second one that included Zelensky. But the Kremlin balked at the subsequent summit, not wanting to legitimize Zelensky by putting him opposite Putin (Trump later said that Zelenky’s eventual inclusion would not be a dealbreaker). White House aides are leery of dispatching Trump to meet with Putin without any guarantee of a deliverable goal—namely, a cease-fire or, at minimum, a real step toward the cessation of hostilities. U.S. and European officials were still gauging whether Russia was serious about curtailing the fighting or simply buying time for more attacks to strengthen its position for future negotiations. And though Trump believes his own personal negotiating skills could sway Putin, it is not clear that Russia would offer an agreement acceptable to Zelensky.
Trump has long argued that it is always better to talk, regardless of who it is with, and he has especially emphasized that dialogue between nuclear-armed states, such as the U.S. and Russia, is imperative. He’s been known to walk away from splashy summits when talks go awry, as he did in 2019, when he abruptly ended his Vietnam meeting with North Korean Chairman Kim Jong Un. He canceled a highly controversial Camp David meeting with the Taliban before it ever took place. But five days is also a long time in Trump’s America, and these fragile efforts to get Trump and Putin in the same Alaskan meeting room could easily hit barriers before the delegations board their flights.
