Oval Office spat to public rebukes: A timeline of Trump-Zelenskyy ties

The criticism on Saturday came as tensions between the US and Ukraine have increased after Trump announced a diesel supply deal with Russia.

“I think it’s ⁠⁠⁠⁠time for Ukraine to get a new president,” Trump told reporters at the White House on Saturday, saying Zelenskyy had hurt global diesel supplies with strikes on Russian refineries.

“He wants to make problems for our farmers, our ranchers with diesel fuel because Russia supplies a large portion of the diesel fuel throughout the world,” Trump added.

Zelenskyy on Sunday pushed back, vowing to continue striking Russian oil refineries. “Ukraine will be ready to stop striking Russian oil refineries if Russia stops striking our energy infrastructure,” Zelenskyy wrote on X.

“It is possible to stop strikes on energy infrastructure as early as today, but (Russian President Vladimir) Putin does not want to do so,” he said.

This is not the first time Trump has lambasted Zelenskyy. Their tense relationship goes back to Trump’s first term as president, when he pressured Zelenskyy to investigate his rival, Joe Biden, and his son, Hunter Biden.

Here’s a timeline of some of the occasions when Trump has been critical of Zelenskyy:

October 2026: In his remarks at the White House, Trump criticised Zelenskyy over the lack of a peace deal while demanding an end to Ukrainian strikes on Russian energy facilities.

“I said to him, ‘Do what you want. Don’t hit refineries. There’s plenty of targets. Don’t ‌‌‌‌hit ‌‌‌‌refineries.’ And he went out and he hit,” Trump said. “He better damn well stop.”

“I suggest they get a new leader who can make a deal because he could have made many deals, but for some reason, he never does,” Trump added.

Trump, who has been urging Zelenskyy to stop attacking Russian energy infrastructure for weeks, struck a deal with Putin on Friday to buy diesel from Russia in an attempt to reduce high fuel prices.

The deal marked a stunning reversal of years of Washington’s pressure on Russia over its full scale invasion of Ukraine.

Zelenskyy, meanwhile, said every additional $1bn Russia earns from exports would help pay for weapons components, drone upgrades, missile production and the recruitment of mercenaries.

Moscow would only be ready to stop when its ability to fight diminished, he added.

April 2025: On April 15 , Trump criticised Zelenskyy and implied Kyiv had started the war against Russia, saying the Ukrainian leader was “always looking to purchase” US missiles. “You don’t start a war against someone 20 times your size and hope people give you some missiles,” Trump said.

Then on April 23 , he criticised Zelenskyy for making “very harmful” statements after the Ukrainian president pushed back against the idea of ceding occupied Crimea to Russia in a potential peace deal.

Zelenskyy had ruled out ceding any territory, declaring, “There is nothing to talk about – it is our land, the land of the Ukrainian people”.

In a post on his social media platform, Trump accused Zelenskyy of stoking tension by “boasting” that Kyiv would not legally recognise ceding Crimea to Russia.

“This statement is very harmful to the Peace Negotiations with Russia,” Trump said, adding that Russia invaded the Crimean Peninsula and annexed it back in 2014 “without a shot being fired”.

“It’s inflammatory statements like Zelenskyy’s that makes it so difficult to settle this War,” Trump said. “He can have Peace or, he can fight for another three years before losing the whole Country.”

Despite the tension, the two leaders held a private meeting at the Vatican on April 26, 2025, during Pope Francis’s funeral.

Feb 28, 2025: During their fiery Oval Office meeting, Trump and Vice President JD Vance clashed with Zelenskyy over rare earth mineral agreements, security assurances and peace negotiations with Russia.

Trump warned Zelenskyy, “You’re either going to make a deal [on ending the war with Russia] or we’re out,” and accused the Ukrainian leader of having “disrespected” the United States and “overplayed his hand”.

The US president and Vance also berated Zelenskyy for lacking gratitude and refusing to compromise to end the war, with Trump arguing that Zelenskyy was unready for peace.

The meeting devolved into a shouting match and Zelenskyy departed the White House abruptly.

February 19, 2025: A month after returning to power for a second term, Trump called the Ukrainian president a “dictator without elections” and accused him of wanting to keep the “gravy train” of US military support going while Washington tries to end the war with Russia.

In a lengthy and scathing post on his social media platform Truth Social, Trump accused Zelenskyy of taking US money and embroiling the country in an endless conflict.

He later doubled down on those comments, telling an audience at an investment summit in Miami that Zelenskyy had “done a terrible job, his country is shattered, and millions and millions of people have unnecessarily died”.

“A dictator without elections. Zelenskyy better move fast or he’s not going to have a country left. Gotta move. Gotta move fast cause that war’s going in the wrong direction,” Trump said on stage at the Future Investment Initiative (FII) Institute summit.

“In the meantime, we’re successfully negotiating an end to the war with Russia. Something I’ll admit that only Trump is going to be able to do and the Trump administration – we’re going to be able to do it. I think Putin even admitted that,” he said.

“Biden never tried. Europe has failed to bring peace and Zelenskyy probably wants to, maybe he wants to keep the gravy train going. I don’t know what’s the problem, but he has been able. He’s very upset,” he added.

Trump had been critical of Biden’s financial and military support to Ukraine during the war. He had vowed to end the war within 24 hours of his taking office, but later said he was being “sarcastic”.

2024 Campaign trail: On the 2024 US presidential election campaign trail, Trump repeatedly criticised Zelenskyy for not trying hard enough to end Russia’s war on Ukraine. In September, at an election rally speech in North Carolina, Trump lashed out at Zelenskyy for refusing to negotiate, stating that even the “worst deal” or giving up a small amount of territory would be better than ongoing death and destruction.

July 2019: During his first term, Trump repeatedly urged Zelenskyy to work with Rudy Giuliani and the US attorney general to investigate Democratic political rival Joe Biden. That is according to a five-page memo summarising the July 25 call.

At the time of the call, the Trump administration was also withholding from Ukraine nearly $400m in congressionally approved security assistance, prompting speculation the US president was using the money as leverage to get his desired investigations.

Zelenskyy expressed willingness to look into new cases and cooperate with US investigations, though he and Ukrainian officials later maintained they did not feel directly threatened or pressured during the conversation itself.