Trump and Zelensky’s relationship explained: From Oval Office clash to cautious reset

Ahead of his Washington visit, European allies advised Zelensky to adopt a more conciliatory style with Trump

When Volodymyr Zelensky last visited the Oval Office in February, the meeting ended in acrimony. President Donald Trump berated him, cancelled a planned luncheon, and told aides the Ukrainian leader should not return “until he is ready for peace.” Trump dismissed Zelensky’s appeals, warning he was “gambling with World War III.” Vice President JD Vance added to the tension, questioning whether Zelensky had ever shown gratitude for US support, CNN reported.

A changed atmosphere since spring

Despite the rupture, Trump and Zelensky began repairing ties in subsequent encounters. They met briefly in April at the Vatican and again in June at the NATO summit in the Netherlands. On both occasions, Trump praised Zelensky’s tone, saying “he couldn’t have been nicer.” Zelensky, in turn, told reporters he believed their Vatican conversation had been the most constructive yet, marking a reset in tone if not in substance.

Alaska summit reshapes the agenda

The landscape shifted again after Trump’s Alaska summit with Vladimir Putin. Trump abandoned his earlier insistence on a cease-fire first, instead exploring a broader peace agreement that could involve Ukrainian concessions. He indicated openness to Putin’s demand for full control of the Donbas, telling European leaders the war could end quickly if Zelensky agreed. This approach has unsettled both Kyiv and its allies, who insist no deal can proceed under bombardment.

European leaders counsel caution

Ahead of his Washington visit, European allies advised Zelensky to adopt a more conciliatory style with Trump. Leaders such as French President Emmanuel Macron and Britain’s Prime Minister Keir Starmer urged demonstrations of gratitude while avoiding confrontational appeals. Zelensky followed their advice, posting on social media his thanks for Trump’s invitation and stressing his desire to discuss “all the details regarding ending the killing and the war.”

Monday’s high-stakes return

Zelensky will now enter the Oval Office flanked by Europe’s top leaders, including Germany’s Friedrich Merz, Italy’s Giorgia Meloni, and EU Commission President Ursula von der Leyen. NATO’s Secretary General Mark Rutte may also attend. The optics contrast with Putin’s Alaska visit, which featured pageantry and personal warmth from Trump but not the symbolism of the Oval Office. For Zelensky, the meeting represents both an opportunity and a test of his recalibrated strategy.

Trust but uncertainty

Trump has publicly praised Zelensky’s recent posture, saying after their June encounter, “He’d like to see it end.” Yet doubts persist about how much leverage the Ukrainian leader has. Trump appears receptive to Putin’s conditions, while offering vague US “security guarantees” once the war ends. The Oval Office discussions will determine whether their repaired rapport can withstand new strains as Zelensky resists land concessions and Trump pushes for rapid resolution.