Timeline of Trump-Zelenskyy Tensions: From the 2019 Call to Public Criticism

U.S. President Donald Trump on October 26 called for Ukraine to have a new president, accusing President Volodymyr Zelenskyy of driving up global diesel prices through attacks on Russian refineries. Speaking at the White House, Trump said: "I think it's time for Ukraine to have a new president," adding that Zelenskyy "wants to make things difficult for our farmers and ranchers with diesel, because Russia supplies most of the world's diesel."

The move came after Trump announced a deal to buy diesel from Russia, reversing years of Washington pressure on Moscow over the Ukraine conflict. Trump said he had asked Zelenskyy to stop attacking Russian energy facilities and warned that "he'd better stop."

On October 27, Zelenskyy responded on social media platform X, stating that Ukraine was ready to halt attacks on Russian refineries if Russia stopped striking Ukraine's energy infrastructure. "The attacks on energy infrastructure could be stopped today, but Russian President Vladimir Putin does not want to do it," Zelenskyy wrote. He also stressed that every additional billion dollars Russia earns from exports helps pay for weapons components, drone upgrades, missile production, and the recruitment of mercenaries.

This is not the first time Trump has criticized Zelenskyy. The strained relationship between the two leaders dates back to Trump's first term, when he pressured Zelenskyy to investigate political rival Joe Biden and Biden's son Hunter.

Below is a timeline of key events in the Trump-Zelenskyy relationship:

October 2026: At the White House, Trump criticized Zelenskyy for failing to reach a peace deal and demanded an end to Ukraine's attacks on Russian energy facilities. He said: "I told him: 'Do what you want. Don't hit the refineries. There are other targets. Don't hit the refineries.' And yet he still hits them. He'd better stop." Trump also suggested Ukraine should have a new leader capable of negotiating. A day earlier, Trump had struck a deal with Putin to buy diesel from Russia to lower fuel prices.

April 2025: On April 15, Trump criticized Zelenskyy and implied that Kyiv started the war with Russia, saying the Ukrainian leader "always wants to buy" American missiles. "You don't start a war with someone 20 times your size and then hope they give you missiles," Trump said. On April 23, Trump criticized Zelenskyy for making "very harmful" statements after the Ukrainian leader opposed the idea of ceding Crimea to Russia in a potential peace deal. Zelenskyy insisted he would not make territorial concessions. In a social media post, Trump accused Zelenskyy of inflaming tensions by "bragging" that Kyiv would not recognize the cession of Crimea to Russia. "This statement is very harmful to peace negotiations with Russia," Trump said, adding that Russia annexed Crimea in 2014 "without firing a shot." Nevertheless, on April 26, 2025, the two leaders still held a private meeting at the Vatican during the funeral of Pope Francis.

February 28, 2025: In a tense meeting in the Oval Office, Trump and Vice President JD Vance argued with Zelenskyy over a rare-earth minerals deal, security guarantees, and peace negotiations with Russia. Trump warned: "Either you make a deal [to end the war with Russia], or we pull out," and accused Zelenskyy of "disrespecting" the United States and "gambling too much." Trump and Vance also criticized Zelenskyy for lacking gratitude and refusing to compromise to end the war. The meeting turned into a major argument and Zelenskyy abruptly left the White House.

February 19, 2025: A month after returning to power for a second term, Trump called Zelenskyy an "unelected dictator" and accused him of wanting to keep the "money flow" of U.S. military aid going while Washington tried to end the war with Russia. In a lengthy post on Truth Social, Trump accused Zelenskyy of taking American money and dragging the United States into an endless conflict. Later, at an investment summit in Miami, Trump said Zelenskyy "has done a terrible job, his country is shattered, millions of people are dying for nothing." Trump also argued that the Biden administration never tried, Europe failed to bring peace, and Zelenskyy might want to keep the "money flow" going.

2024 campaign: On the campaign trail for the 2024 U.S. presidential election, Trump repeatedly criticized Zelenskyy for not trying hard enough to end Russia's war in Ukraine. In September, at a rally in North Carolina, Trump attacked Zelenskyy for refusing to negotiate, declaring that even the "worst deal" or ceding a small piece of territory would be better than continued death and destruction.

July 2019: During his first term, Trump repeatedly urged Zelenskyy to work with Rudy Giuliani and the U.S. attorney general to investigate Democratic political rival Joe Biden, according to a five-page memorandum summarizing the July 25 call. At the time of the call, the Trump administration was also withholding nearly $400 million in congressionally approved security aid to Ukraine, fueling speculation that the U.S. president used the money as leverage to get the investigation he wanted. Zelenskyy expressed willingness to look into new cases and cooperate with U.S. investigations, though he and Ukrainian officials later insisted they did not feel threatened or directly pressured during the conversation.