President Donald Trump and his Ukrainian counterpart Volodymyr Zelenskyy return to the negotiating room on Sunday with a familiar, fraught task: trying once again to chart a path toward ending Russia’s war against Ukraine.
The two leaders have met three times since Trump took office for a second time in January, with each encounter carrying high expectations but producing few concrete results, and sometimes even appearing to push a resolution further away.
As Kyiv presses Trump to deliver security guarantees, questions remain over whether the Florida summit marks a genuine turning point or another round of high-stakes diplomacy with little for Zelenskyy to take home.
Eight months ago, a White House meeting in February ended in acrimony and failed to produce the breakthrough Trump had promised on “day one” of his administration.
European leaders flanked Zelenskyy on his next visit to the White House in August as they grappled for a voice in the faltering negotiations, but Europe has since remained largely shut out of high-level talks as Russia refuses to budge from its maximalist demands.
There now appear to be signals from the Ukrainian camp that Kyiv may be prepared to compromise with Moscow.
Zelenskyy said Sunday in a Telegram post that “much can be decided before the New Year,” but “whether decisions will be made depends on our partners.”
Last week, he outlined elements of an updated proposal that would see Ukraine potentially withdraw troops from parts of the east without recognizing captured areas as Russian territory, with a demilitarized zone established in their place.
Such suggestions had previously appeared to be red lines in peace talks. Until Tuesday, Zelenskyy had maintained that he would be unwilling to withdraw troops from the country’s eastern industrial heartland, much of which has been occupied by Russian forces, as part of any plan to end the war.
But he has remained firm on another issue.
Zelenskyy said the question of U.S.-backed security guarantees for Ukraine, aimed at preventing further Russian incursions, would ultimately depend on the U.S. president.
“For us, it is very important that there is a signal that we want legally binding security guarantees,” Zelenskyy told Ukrainian journalists in a Q&A session via WhatsApp on Saturday. “This primarily depends on President Trump. The question is what security guarantees President Trump is ready to provide to Ukraine.”
That said, Ukraine’s history underscores the dangers of relying on security assurances as a long-term solution. The Budapest Memorandum, signed in 1994 in exchange for Ukraine giving up its nuclear weapons, committed the U.S. and Russia to respecting Ukraine’s territorial integrity.
It was shattered in 2014 with Russia’s annexation of Crimea and incursions in eastern Ukraine, followed by the full-scale invasion of Ukraine almost four years ago, which sparked the deadliest conflict in Europe since World War II.
It remains unclear whether Zelenskyy’s optimism is widely shared. He presented a united front with European leaders and Canadian Prime Minister Mark Carney after meetings on Saturday, though there was little sign of an imminent breakthrough.
While European Commission President Ursula von der Leyen said countries would work toward a “shared objective,” divisions have blown up in recent weeks over since-dropped plans to hand seized Russian assets to Ukraine.
And it’s unclear how Russian President Vladimir Putin, and even Trump himself, will ultimately respond to Zelenskyy’s latest peace offerings.
Putin told some of Russia’s top businessmen that he might be open to swapping some territory controlled by Russian forces in Ukraine, but that he wanted full control of the Donbas region, the Kommersant newspaper reported on Friday.
“Vladimir Putin asserted that the Russian side is still ready to make the concessions that he made in Anchorage. In other words, that ‘Donbas is ours,’” Kommersant reported. In essence, Putin wants the whole of Donbas, though outside that area “a partial exchange of territories from the Russian side is not ruled out,” wrote columnist Andrei Kolesnikov.
Such hard-line demands, held by Putin throughout the conflict, still appear well at odds with Zelenskyy’s pathway to peace.
While demilitarized zones remain a possibility, Zelenskyy said Ukraine and the United States have not found common ground on demands that Ukraine cede the parts of Donbas it still controls.
After heavy Russian strikes hit Kyiv across the weekend, killing two and injuring dozens more, Zelenskyy said Saturday that Putin is not interested in peace, accusing him of seeking to prolong the war and “use every opportunity to cause Ukraine even greater suffering.”
Trump, meanwhile, has remained publicly noncommittal. Asked about Zelenskyy’s visit, he told Politico: “We will see what he’s got.”
A Ukrainian official familiar with the planning for Sunday’s meeting between Zelenskyy and Trump told NBC News that in addition to security guarantees for Ukraine, the Ukrainians are preparing to discuss economic prosperity and reconstruction of the war-torn country.
There are also talks of holding a joint news conference with Trump and Zelenskyy, not necessarily to announce anything new, but to discuss the results of the meeting, the Ukrainian official said.
Still, expectations persist that there will be something new for the duo to say Sunday, after years of deadlock and over a million dead.
From a European and Ukrainian perspective, “what we’re talking about now has much more substance than it used to,” said Moritz Brake, a senior fellow at the Center for Advanced Security, Strategic and Integration Studies.
“Zelenskyy has clearly demonstrated his willingness to compromise, to come to a sort of an agreement, especially when there’s perspective for future stability with U.S. security guarantees,” he told NBC News. “The big question remains, is Russia really willing to concede or to agree to an honest peace plan on terms that are also acceptable to Ukraine?”
“That is something we cannot see at the current moment,” he added.

