Friday will be the sixth meeting between U.S. President Donald Trump and Ukrainian President Volodymyr Zelenskiy since Trump returned to the White House in January.
And while the US president has recently stepped up his support for Ukraine, previous talks have not always gone as planned.
February 28, 2025
The first meeting between President Trump and President Zelensky quickly devolved into a full-blown shouting match on live television in the Oval Office.
The debate was intended to focus on U.S. aid to Ukraine and the mineral deal, but quickly turned sour as U.S. Vice President Vance accused Zelenskiy of being “disrespectful” and “ungrateful.”
President Trump initially opted for silence while Vance addressed the Ukrainian leader, but later intervened after Zelensky suggested that the United States was also involved in supporting Ukraine, saying Washington would “feel the influence of Mr. Putin” if it did not take decisive action to stop Mr. Putin.
President Trump was furious: “You are gambling with the lives of millions of people.” “You’re betting on World War III,” he added.
Zelenskiy left the White House after a heated argument and without an agreement or even a joint press conference with Trump, which is a tradition in the White House after a meeting between a US president and a foreign leader.
Trump also ordered a suspension of U.S. military aid shipments to Ukraine immediately after Zelensky left office.
April 26, 2025
The two leaders met at the Vatican on the occasion of Pope Francis’ funeral and reached a reconciliation.
The 15-minute private meeting, organized by Vatican officials just before the start of services in St. Peter’s Basilica, was an important step toward reconciliation between the two leaders.
June 25, 2025
President Donald Trump and President Volodymyr Zelenskiy met on the sidelines of the NATO summit in The Hague, where Trump formally announced a strategy to increase the military burden of European allies by pushing for a significant increase in the alliance’s mandatory defense spending.
President Trump was able to get all member states except Spain to commit to a new target of 5% of gross domestic product (GDP) by 2035, up from the previous target of 2%.
The US president also called for increased European responsibility for Ukraine’s military needs.
August 18, 2025
Just three days after his summit in Alaska with Russian President Vladimir Putin, President Trump convened a meeting with Zelensky and several European leaders at the White House.
The meeting appeared to be primarily a diplomatic effort led by President Trump and was aimed at exploring the possibility of direct peace negotiations with Russia. President Trump has previously said that after his meeting with President Putin, he would like to hold a trilateral summit and have direct dialogue between the opposing presidents.
September 23, 2025
Zelensky met with Trump for the sixth time this year on the sidelines of the United Nations General Assembly High-Level Week in New York last month.
Although details remain somewhat hazy, President Trump has hinted at the possibility of U.S. air support for European forces in Ukraine under a post-conflict framework.
