The relationship between US President Donald Trump and Ukrainian President Volodymyr Zelenskyy has moved through moments of warmth, confrontation, and renewed diplomacy as Washington has tried to broker an end to Russia's war in Ukraine.
From their early meetings during Trump's first presidency to their most recent talks, the two leaders have repeatedly differed over how to achieve peace and how much support Ukraine should receive from the United States.
Here is how their relationship unfolded.
September 2019 | A friendly beginning
Ukrainian President Volodymyr Zelenskiy said that he was not pushed by US President Donald Trump to investigate a political rival, former Vice President Joe Biden, and did not want to be involved in the US elections.
But the relationship soon became entwined with US domestic politics, after Trump was accused of pressuring Zelenskyy to investigate Joe Biden, then a Democratic presidential candidate. Zelenskyy said at the time that he did not want to become involved in US elections.
September 2024 | Trump and Zelenskyy meet again
Trump, then a former president and Republican presidential candidate, met Zelenskyy in New York during the 2024 US presidential campaign.
The meeting came after Trump criticized the Ukrainian leader on the 2024 campaign trail and expressed doubts that the US ally could win its war with Russia.
February 28, 2025 | Oval Office confrontation
Zelenskiy and Trump clashed repeatedly during an encounter before the media in the Oval Office, with Zelenskyy urging Trump to be cautious with Russia and Trump accusing him of being disrespectful, as simmering differences spilled into the open.
"You're gambling with the lives of millions of people. You're gambling with World War Three, and what you're doing is very disrespectful to the country. This country, that's backed you far more than a lot of people said they should have,” criticised Trump.
A minerals deal was left unsigned after Zelenskyy left the White House early following the contentious meeting.
April 26, 2025 | A brief thaw at the Vatican
Months later, the tone changed.
Trump and Zelenskiy met one-on-one in a marble-lined Vatican basilica 26 while attending the funeral of Pope Francis.
Zelenskyy said the meeting could prove historic if it delivers the kind of peace he is hoping for, and a White House spokesman called it "very productive".
The meeting was their first since the angry encounter in the Oval Office in February and came at a critical time in negotiations aimed at bringing an end to fighting between Ukraine and Russia
AUGUST 18, 2025 | Another try for peace
Ukrainian President Volodymyr Zelenskyy gathered with US President Donald Trump and seven European leaders for an extraordinary summit at the White House to discuss a path to ending Russia's war in Ukraine.
Meeting on the sidelines of a UN General Assembly, Trump and Zelenskyy discussed Russian violations of NATO airspace and American efforts to put further pressure on Moscow and its allies to agree to a resolution to the conflict.
October 17, 2025 | Trump says both sides want peace
Trump met Zelenskyy, telling reporters that both Zelenskyy and Russian President Vladimir Putin are seeking an end to the war in Ukraine.
Zelenskyy visited the White House to plead for Tomahawk missiles. Trump portrayed himself as a mediator and reiterated his belief that both sides seek a peace deal.
Trump's conciliatory tone after a call the previous night with Putin raised questions over the near-term likelihood of assistance to Ukraine and reignited European fears of a deal that suits Moscow.
December 28, 2025 | Trump presses for a deal
Zelenskyy arrived in Miami to meet Trump. The talks in Florida were expected to focus on forging a plan to end the war in Ukraine.
"Gotta make a deal. Gotta get it done. Too many people died. And I think both presidents want to make a deal," Trump answered when the press asked him what his message to Putin was.
Trump added that he was hopeful talks to resolve the war in Ukraine were closer after a lengthy meeting with Ukrainian President Volodymyr Zelenskiy in Florida.
January 22, 2026 | Davos talks
Zelenskyy arrived in Switzerland for talks with Trump. The Ukrainian leader had said he would only travel to Davos if there was the opportunity to sign an agreement with Trump on resolving the nearly four-year war that included security guarantees and post-war reconstruction funding for Ukraine.
Trump said he believed peace efforts were getting closer and repeated his message to Putin: “The war has to end.”
Zelenskiy replied that a document outlining US security guarantees for Ukraine was complete but that territorial issues had not yet been resolved in the war against Russia's invading forces.
June 16, 2026 | Meeting at the G7
Zelenskyy met Trump and US Secretary of State Marco Rubio on the sidelines of the G7 summit. Zelenskyy's communications adviser said the leaders talked as part of a broader meeting at the summit.
July 8, 2026 | NATO summit in Ankara
Zelenskiy told Trump in Ankara at the NATO summit that a trip to the Russian capital to meet with Russian President Vladimir Putin would be ‘difficult’ because of the number of Ukrainian drones in the air.
During their meeting, Trump also said that the United States will give a license to Ukraine for Patriot missiles, as he said both Russia and Ukraine want to see the war settled
What comes next?
The long and often volatile relationship between Trump and Zelenskyy has repeatedly shifted between cooperation and confrontation.
Their disagreements have centred on the pace and terms of peace negotiations, military assistance and the security guarantees Ukraine would need to accept any settlement with Russia.
Yet despite their February 2025 confrontation, subsequent meetings have shown that the two leaders remain in contact as Washington continues to pursue a negotiated end to the war.
The central question remains whether diplomacy can bridge the gap between Trump's push for a deal and Kyiv's demand for a settlement that does not leave Ukraine vulnerable to another Russian attack.
