Donald Trump is heading into one of the most closely watched diplomatic encounters of his presidency — a face-to-face meeting with Vladimir Putin in Alaska this Friday. For many in Ukraine and across Europe, the moment carries an unsettling historical echo. The absence of Ukrainian and European representation at the table has drawn comparisons to the 1938 Munich Agreement, when the fate of Czechoslovakia was decided without its leaders present. Back then, Adolf Hitler, Benito Mussolini, Édouard Daladier and Neville Chamberlain carved up the country in a deal that was sold as “peace” but paved the way for greater conflict.
Trump insists this meeting will be different — and short. He claims he’ll know within two minutes whether there’s any chance of ending the war in Ukraine. “I may leave and say good luck, and that’ll be the end,” he told reporters. Yet his critics believe he has more than peace in mind. They see a man chasing a legacy moment, perhaps even the Nobel Peace Prize he has long coveted — and which Barack Obama received early in his presidency, something Trump has never forgotten.
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The Nobel Committee cited Obama’s “extraordinary efforts to strengthen international diplomacy and cooperation,” awarding him the prize less for concrete results than for the hope he inspired. Trump sees himself differently — as a “president of peace” who has brokered agreements from the Middle East to the Balkans. In the White House’s own list, those deals include the Abraham Accords and mediations involving countries from Azerbaijan to Ethiopia. Ending the war in Ukraine, his allies argue, would be the crowning achievement.
But there’s another theory: that Trump wants a “deal” in the business sense — something he can brand as a win and point to as proof of his negotiating genius. Eastern Ukraine, rich in rare earth minerals, is of particular interest. Trump has already signed an agreement with President Volodymyr Zelensky granting rights to mine these resources. That fact alone fuels speculation that his motivation may not be entirely about diplomacy.
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Across the table will be Putin — an autocrat with an imperial vision. He has repeatedly claimed Ukraine is not a real country, framing it as an existential threat to Russia. Former British Deputy Prime Minister David Liddington says Putin models himself on Russia’s great rulers, comparing his ambitions to both Peter the Great and Catherine the Great, who vastly expanded the empire’s reach. In his Kremlin office, Putin keeps a bust of Catherine, a reminder of his appetite for territorial gains.
Diplomats who have dealt with Putin say he is calculated, secretive and always determined to reassert his position rather than make concessions. Margaritis Schinas, former vice president of the European Commission, describes him as someone fluent in the power games of intelligence and security, not the transactional bargaining Trump prefers. According to former Irish ambassador Bobby McDonagh, Putin is “utterly predictable” — relentless in pursuing what he defines as Russian interests.
His strategy for the Alaska meeting will likely follow a familiar structure: first, a larger session with aides and interpreters where he outlines his stance, often with pointed criticism of opponents; then, a private tête-à-tête where he may show small signs of flexibility. That second part will be where he presses hardest for his goals — particularly the easing of Western sanctions, which the UK estimates have cost Russia at least £333 billion in war funds since 2022.
Former U.S. national security adviser John Bolton warns that Putin will use all his KGB-honed skills to sway Trump. Keeping Zelensky and European leaders out of the room, Bolton says, is deliberate — it removes distractions and allows Putin to work Trump directly. “He’s going to try to get Trump back on side,” Bolton warns, noting that Putin has sought to influence him since the start of his presidency.
What Putin wants is no mystery: recognition of Russian sovereignty over Crimea, Donetsk, Luhansk, Zaporizhzhia and Kherson; a weakened Ukrainian military; and a guarantee that Kyiv will never join NATO. For Ukraine, agreeing to these terms would mean surrendering its sovereignty.
Trump’s inner circle doesn’t inspire much hope in Kyiv. Tulsi Gabbard, his intelligence chief, has shown little sympathy for Ukraine’s cause. Defense Secretary Pete Hegseth and running mate JD Vance have openly called for Ukraine to cede territory. This makes it less likely that Trump will take advice from European leaders such as Britain’s Sir Keir Starmer, who will meet him just before the summit.
Still, there’s an unpredictable element. Some observers draw parallels to Ronald Reagan’s surprise turn at the 1986 Reykjavik summit with Mikhail Gorbachev, which, despite no immediate deal, set the stage for the end of the Cold War. Sir Julian King, Britain’s last European Commissioner, points out that Trump — for all his unpredictability — will be wary of appearing weak. That, he says, might be the one saving grace for Ukraine.
As the clock ticks toward Friday, the stakes are enormous. Putin will come armed with a maximalist agenda and the patience to press it. Trump will arrive with the confidence — or overconfidence — that he can size up his counterpart in mere minutes. Between them lies the fate of Ukraine’s territory, the resilience of Western alliances, and perhaps Trump’s own vision of his place in history.
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