On the eve of another fraught round of diplomacy, Ukraine finds itself at the crossroads of hope and uncertainty. President Volodymyr Zelenskyy, determined as ever to secure his country’s future, announced that Ukrainian officials will meet representatives of U.S. President Donald Trump in New York on August 29, 2025, as part of a renewed push to end the grinding war with Russia. This high-stakes dialogue comes amid an uptick in both diplomatic activity and battlefield violence, with all sides searching for a breakthrough that remains stubbornly out of reach.
Speaking during his nightly address on August 27, Zelenskyy revealed not only the planned meeting but also the appointment of a new Ukrainian ambassador to the United States. Former Justice Minister Olha Stefanishyna will take over from Oksana Markarova, who has served since 2021. According to AFP, Zelenskyy emphasized, “Much of Ukraine’s long-term security depends on relations with America,” underscoring that continued U.S. weapons transfers are a top priority for Kyiv. The message was clear: as the war enters yet another chapter, Ukraine’s ties with Washington are more vital than ever.
The diplomatic flurry is not limited to New York. In the days leading up to the announcement, Ukraine’s government delegation embarked on a whirlwind tour, visiting Qatar, Saudi Arabia, and Switzerland. In Riyadh, Zelenskyy’s Chief of Staff Andriy Yermak met with the Saudi defense minister and national security adviser to discuss “paths to peace in Ukraine and Saudi Arabia’s participation in this process,” according to Yermak’s post on Telegram. The aim, as articulated by Kyiv, is to build an international coalition to pressure Russia into meaningful negotiations.
Yet, the path to peace remains riddled with obstacles. Despite a much-publicized summit between Trump and Russian President Vladimir Putin in Alaska on August 15, little tangible progress has been made. The two leaders exchanged warm words, but no peace agreement emerged. The prospect of a direct Zelenskyy-Putin meeting, which Kyiv has repeatedly sought, remains elusive. As Reuters reports, Russian Foreign Minister Sergey Lavrov recently stated that no such meeting was planned, though Putin would be ready once a clear agenda was established. Zelenskyy, for his part, has decried what he called “very arrogant and negative signals from Moscow regarding the negotiations,” urging the international community to “force Russia to take real steps.”
Behind the scenes, the Trump administration’s approach to Ukraine has been anything but conventional. Shortly after a meeting with Putin in Moscow on August 6, Trump’s special envoy Steve Witkoff reported that the Russian president was prepared to offer significant territorial concessions to end the war. Trump, buoyed by this so-called “great progress,” agreed to the Alaska summit, with talk of a land swap on the table. However, confusion quickly set in. On August 7, Witkoff told European leaders that Putin was willing to withdraw from the Ukrainian regions of Zaporizhzhia and Kherson in return for Kyiv ceding Donetsk and Luhansk. According to Reuters, this proposal startled many European officials, who saw it as a sharp departure from previous Russian positions.
The next day, Witkoff appeared to walk back his earlier account. In a call convened by U.S. Secretary of State Marco Rubio, he stated that Putin was not, in fact, offering to withdraw from Zaporizhzhia and Kherson. Instead, Putin had signaled lesser concessions, including not demanding formal Western recognition of those territories as Russian. The lack of an official State Department notetaker at the Moscow meeting meant there was no authoritative record of what Putin actually proposed, further muddying the waters. As one U.S. official confided to Reuters, the resulting confusion left both American and European allies scrambling to interpret Moscow’s true intentions.
This seat-of-the-pants style has become a hallmark of Trump’s foreign policy. Supporters argue it has yielded breakthroughs unimaginable under previous administrations, such as the opening of U.S. relations with Syria and the establishment of a direct line to Putin. Critics, however, worry that bypassing traditional diplomatic channels has sown chaos within the administration and alarmed allies. Kurt Volker, a former U.S. ambassador to NATO and special representative for Ukraine, summed up the situation: “We are just exactly where we were before Trump took office. Russia has not changed its position one iota. The war is raging on... We don’t have a clear strategy of how to get Putin to stop the war.”
Indeed, the reality on the ground in Ukraine remains bleak. On August 27, Ukraine’s General Staff reported that Russian forces had launched a barrage of attacks: two missile strikes, 64 air strikes (including 109 guided aerial bombs), and 4,625 shelling attacks, among them 21 barrages from multiple launch rocket systems and nearly 3,900 kamikaze drones. Air strikes targeted Stara Huta in the Sumy region, Bilohiria and Preobrazhenka in Zaporizhia, and Antonivka in Kherson. Russian forces also made ground gains, taking Zaporizke and Novoheorhiivka in Dnipropetrovsk and advancing near Shevchenko, Bila Hora, and Oleksandr-Shultyno. Russia’s Ministry of Defence, quoted by TASS, claimed that its air defenses shot down 191 Ukrainian drones, six guided aerial bombs, and a long-range guided missile in a single day.
Meanwhile, the Trump administration’s diplomatic efforts have been accompanied by a sweeping purge of Russia and Ukraine experts at key U.S. agencies, including the Pentagon, State Department, and National Security Council. Trump has relied heavily on trusted advisers like Witkoff, whose lack of diplomatic experience has raised eyebrows among U.S. and European officials. Some fear that Moscow may be exploiting this inexperience to its advantage. Even so, Trump’s team remains adamant that they are unified and effective, with State Department spokesperson Tommy Pigott insisting that Witkoff, Rubio, and Trump’s Ukraine envoy Keith Kellogg are “in lockstep” in implementing the president’s America First foreign policy.
Despite the confusion, there have been moments of cooperation. After the Alaska summit, Trump and European leaders agreed to draft the contours of future security guarantees for Ukraine, with foreign ministers and military officials holding ongoing calls to determine each country’s role. However, Russian officials, including Lavrov, have made clear that they will not accept any Ukrainian security guarantees that involve foreign troops on Ukrainian soil. The road ahead, it seems, will be long and fraught with disagreement.
All the while, the violence continues to escalate. On August 28, a Russian missile and drone onslaught across Ukraine included the second-biggest bombardment of Kyiv with those weapons since the war began. Keith Kellogg, Trump’s special envoy to Ukraine, denounced the attacks as “egregious” and said they “threaten the peace” the president is pursuing. For everyday Ukrainians, these words offer little comfort as the war grinds on with no end in sight.
As Zelenskyy prepares for his delegation’s meeting with Trump’s representatives in New York, the stakes could hardly be higher. With shifting proposals, diplomatic confusion, and relentless violence, Ukraine’s fate hangs in the balance. Whether this latest round of talks can break the deadlock is the question on everyone’s mind—but for now, the only certainty is uncertainty itself.
