Friday marks the sixth meeting between US President Donald Trump and his Ukrainian counterpart Volodymyr Zelenskyy since Trump’s return to the White House in January.
And while the US president has recently demonstrated more support for Ukraine, their previous meetings did not always go as planned.
28 February 2025
The first meeting between Trump and Zelenskyy quickly escalated into a full-blown shouting match, in the Oval Office, on live TV.
The discussion, meant to focus on US support for Ukraine and the minerals agreement, quickly turned sour, as US Vice President JD Vance accused Zelenskyy of being “disrespectful” and “ungrateful”.
Trump, who earlier opted to keep quiet as Vance addressed the Ukrainian leader, later jumped in after Zelenskyy suggested that the US too has a stake in supporting Ukraine, stating that Washington will “feel Putin’s influence” if it doesn’t take decisive action to stop him.
“You’re gambling with the lives of millions of people,” Trump snapped. “You’re gambling with World War Three,” he added.
Zelenskyy left the White House after the heated spat, without a deal, or even a joint press conference with Trump – a White House tradition after meetings between the US president and foreign heads of states.
Trump also ordered a temporary pause on the shipment of US military aid to Ukraine shortly after Zelenskyy’s departure.
26 April 2025
The two leaders made amends during their meeting at the Vatican on the sidelines of Pope Francis’ funeral.
A private 15-minute talk, organised by Vatican officials just before the service commenced in St. Peter’s Basilica, was a significant step towards reconciliation between the two leaders.
25 June 2025
Donald Trump and Volodymyr Zelenskyy met on the sidelines of the NATO summit in The Hague, where Trump formalised his strategy of increasing the military burden on European allies by pushing for a substantial raise in the alliance’s compulsory defence spending commitments.
Trump was able to make all member states, with the exception of Spain, commit to a new target of 5 percent of GDP by 2035, up from previous targets of 2 percent.
The US president also pushed for greater European responsibility towards Ukraine’s military needs.
18 August 2025
Just three days after the Alaskan summit with Russian President Vladimir Putin, Trump convened a meeting with Zelenskyy and several European leaders in the White House.
The meeting, largely seen as a diplomatic effort led by Trump, intended to explore the possibility of direct peace talks with Russia. Trump noted previously following his meeting with Putin that he wants to hold a trilateral summit and engage the warring presidents in direct dialogue.
23 September 2025
Zelenskyy met Trump for the sixth time this year on the sidelines of the United Nations General Assembly High-level Week in New York last month.
While details remain somewhat ambiguous, Trump has indicated potential US air support to European forces in Ukraine under a post-conflict framework.
