Eighteen months after President Donald Trump vowed to quickly end the Russia-Ukraine War, his chief negotiator, Steve Witkoff, made his first trip to the Ukrainian capital on September 6. The visit, which included a meeting with President Volodymyr Zelensky, was welcomed by Ukrainians, but it remains unclear whether it signals a genuine shift in the administration's approach—one that has so far produced no ceasefire, no settlement, and no softening of Moscow's demands.
The conflict, which began with Russia's 2014 seizure of Crimea and escalated into a full-scale invasion in 2022, has become the largest war in Europe since 1945. Trump's first term did little to prevent that invasion, and his second-term mediation efforts have been widely criticized as one-sided and ineffective. Witkoff's nine visits to Moscow before finally going to Kyiv underscored the imbalance, though his presence in Kyiv—alongside Jared Kushner and with British, French, and German national security advisors joining part of the talks—was a positive, if overdue, step.
But the visit produced no visible breakthrough. As Trump's foreign policy distractions mount, critics argue that his approach to Putin is fundamentally flawed. Trump has repeatedly claimed that Putin wants peace, telling reporters in July that "President Putin wants it to end, I will tell you that very strongly." Yet the Kremlin has consistently stated it will settle only on its own terms, which remain unchanged from 2024. Putin's spokesman, Dmitriy Peskov, reiterated on August 28 that Russia's "position has not changed. It was set out two years ago by [Putin]."
Putin has shown he can game Trump. At their August 2025 meeting in Alaska, Trump arrived demanding a ceasefire or consequences, but Putin left without agreeing to anything—and faced no repercussions. Similarly, a planned October Oval Office meeting with Zelensky, where Kyiv hoped for long-range missiles, was undermined when Putin called Trump the night before, and Zelensky went home empty-handed. As former U.S. Ambassador to Ukraine Steven Pifer notes, "Putin respects strength. Trump has not shown that in his dealings with the Russian."
Witkoff, too, has been criticized for naively taking Russian assurances at face value. After Putin denied sharing intelligence on U.S. forces with Iran, Witkoff said, "We can take them at their word." He also floated a 28-point peace plan in November that favored Moscow, including demands for Ukraine to cede territory never occupied by Russian forces. Unsurprisingly, Putin said of Witkoff and Kushner, "We work with them with pleasure."
To break the impasse, Pifer argues, Trump must back diplomacy with pressure. He could leverage Elon Musk to lift restrictions on Starlink use for Ukrainian drone strikes, tighten enforcement against advanced technology exports to Russia, impose secondary sanctions on buyers of Russian oil like China, and target more "shadow fleet" tankers. He could also ask Congress for new military aid for Ukraine, sending Putin a clear message that the West will sustain Ukraine's defense.
Such measures would raise the costs of Putin's war and strengthen Witkoff's bargaining hand. But so far, Trump has avoided them, and Putin has learned he can defy Trump without penalty. As questions about Trump's management style persist, the administration's Ukraine policy remains adrift. Absent a radical change, Pifer concludes, the Trump team "will not bring peace closer to Ukraine. It will only continue to fail."
The stakes are high: every day of delay means more Ukrainian cities under fire and more lives lost. With global energy prices spiking amid the conflict, the economic fallout also deepens. Whether Trump will shift course—or continue to let Putin dictate terms—remains the central question of his mediation effort.
