By his own admission, it was a failure. In a surprisingly frank Oval Office interview, Trump conceded that his high-profile attempt – Anchorage summit with Vladimir Putin – to secure a Ukraine ceasefire “achieved nothing.” He said he thought he had it “done,” but now expects Ukraine and Russia to “keep fighting… stupidly, keep fighting.” Those words stripped away the carefully choreographed images of Trump and Putin shaking hands in Alaska just two weeks ago. President Trump, who built his political brand on cutting deals no one else could, has laid bare the limits of his one-man approach to diplomacy.
The Anchorage meeting was billed as a turning point. Trump entered the talks confident that his personal rapport with Putin would produce results where traditional diplomacy had faltered. Yet Moscow emerged with validation and nothing in return. Trump’s candor is rare in the political theater of Washington, but it also highlights the limits of his approach. Ukraine remains under relentless attack, with missile strikes on Kyiv in late August killing at least 23 civilians. Putin is playing a long game, betting that Western unity will fracture under the weight of sanctions fatigue and war costs. The Alaska episode suggests that, so far, he is winning that bet.
Trump’s supporters, however, remain convinced he is the best chance for peace. They point to his unconventional record: the 2020 Abraham Accords, which normalized ties between Israel and several Arab states, and the August 2025 Armenia–Azerbaijan agreement signed at the White House. While both accomplishments were limited, they demonstrated Trump’s willingness to bypass traditional diplomatic channels. His summits with Kim Jong-un similarly produced little concrete change but opened dialogue with an isolated regime. These episodes reinforce the idea that Trump thrives on personal engagement and showmanship. But Ukraine is a different challenge altogether – a live war involving massive destruction, entrenched territorial disputes, and global stakes that extend far beyond Eastern Europe.
The costs of the conflict are staggering. The World Bank now estimates damage to Ukraine at over $500 billion. More than 10 million people have been displaced since Russia’s full-scale invasion in 2022, according to UNHCR. These are not numbers that can be brushed aside with symbolic summits. Any settlement that legitimizes Russian control over Crimea or the Donbas risks institutionalizing aggression and setting a dangerous precedent for other revisionist powers.
Putin knows this. His goal is not to end the war quickly but to outlast Western resolve. Russia’s economy, which contracted 3.4 percent in the second quarter of this year, is straining under sanctions and the costs of war. Yet Putin left Alaska with global attention, a handshake photo op, and no commitments to de-escalate. Trump’s willingness to talk territory concessions and limit American involvement aligns disturbingly well with Moscow’s interests.
The narrative that Ukrainian President Volodymyr Zelensky is corrupt or ineffective—echoed by some in Trump’s orbit further undermines Kyiv’s standing. Zelensky faces undeniable political headwinds: declining popularity, accusations of over-centralization, and the crushing responsibility of leading a nation under siege. Still, Ukraine has demonstrated remarkable resilience, controlling about 80 percent of its pre-2022 territory and targeting Russian energy routes in the Black Sea. Portraying Zelensky as expendable tilts the negotiating table toward Moscow and signals to other authoritarian leaders that democratic governments can be weakened through brute force.
History provides an uncomfortable warning. In the 1930s, European leaders believed that conceding territory to aggressive regimes would buy peace. Instead, it hastened catastrophe. Today’s world is different—global economies are more intertwined, NATO is stronger, and nuclear deterrence looms over every calculation—but rewarding territorial conquest remains a recipe for future instability. A Ukraine settlement that trades land for temporary quiet would embolden not only Moscow but also Beijing, Tehran, and Pyongyang, all of whom are closely watching how this war reshapes the international order.
America’s own stake is enormous. Since 2022, Washington has sent over $180 billion in military and economic aid to Ukraine, a figure that underscores NATO’s credibility as much as it does U.S. commitment to European security. Trump’s “America First” message, which increasingly frames Ukraine as “mostly Europe’s” problem, ignores the lessons of 1914 and 1939: regional wars have a habit of escalating into global ones. A withdrawal of American leadership would send a clear signal to adversaries that alliances are conditional and Western deterrence is weakening.
Steve Witkoff, Trump’s special envoy, has floated a plan that would give Ukraine security guarantees in exchange for territorial concessions. But Kyiv has reason to doubt such promises. In 1994, Ukraine surrendered its nuclear weapons under the Budapest Memorandum in exchange for assurances of territorial integrity, only to see those guarantees crumble when Russia annexed Crimea twenty years later. Without enforceable commitments—backed by NATO forces, robust sanctions, and international legal accountability—new guarantees risk being little more than paper promises.
Trump’s admission of failure may at least clear the air. It punctures the illusion that bold, one-off negotiations can deliver durable peace in a war of this scale. If the United States wants a settlement that protects Ukraine’s sovereignty, it will require a coalition-driven strategy. That means tightening sanctions on Russia, increasing military assistance to Kyiv, and preparing a long-term plan for postwar reconstruction and security. It also means pursuing justice for war crimes through the International Criminal Court, even if doing so complicates diplomacy.
Trump’s direct engagement style is not without value. In some contexts, personal diplomacy can break stalemates. But Anchorage demonstrated the risks of overestimating its power. Putin exploited the optics without offering concessions, while Trump’s own remarks revealed frustration and fatigue rather than a roadmap for resolution.
A peace deal is possible, but not at any price. Conceding Ukrainian land would pause the fighting but reward aggression, embolden autocrats, and undermine the principles that have underpinned global stability since World War II. The Anchorage summit was a reminder that a handshake cannot replace strategy. For Trump, it may have been a political spectacle. For Ukraine, it was another missed opportunity for meaningful progress—and a warning of what happens when diplomacy trades principle for optics.
