US President Donald Trump is gearing up for a White House meeting with Ukrainian counterpart Volodymyr Zelenskyy on Friday, fresh off a marathon phone call with Russian President Vladimir Putin that set the stage for a future meeting in Budapest.
On the agenda: military aid, and whispers are swirling that the US might hand Ukraine long-range Tomahawk cruise missiles—a move that could shake up the battlefield. Trump has hinted he’d like to float the idea by Putin first, hoping to sweeten the deal for cooperation as he continues his quest to broker an end to the conflict.
From 2019, when Zelenskyy became the President to 2025 the relationship between the two leaders have eveolved. Here is the timeline:
Zelenskyy became President
21 April 2019: Volodymyr Zelenskyy wins the Ukrainian presidency. President Trump, still in his first term, calls to congratulate him, describing the election as “incredible” and expressing confidence that Zelenskyy “will do a great job.”
2019: Allegations emerge suggesting Joe Biden, then a Democratic presidential frontrunner, lobbied Ukraine to dismiss its top prosecutor to protect his son, Hunter Biden, who served on the board of energy company Burisma. These claims are later found to be fabricated, with the prosecutor’s removal officially attributed to corruption, BBC reported.
25 July 2019: In a call that eventually triggers Trump’s first impeachment, he urges Zelenskyy to investigate the Biden allegations. Zelenskyy responds that the evidence would be reviewed later that year.
29 September 2020: During the first Trump-Biden presidential debate, Trump references Hunter Biden’s business dealings in Ukraine, framing them as part of broader criticism of the Biden family.
Ukraine war begun
24 February 2022: Russia launches a full-scale invasion of Ukraine. Trump labels the attack “appalling” and commends Zelenskyy for remaining in Kyiv, asserting the conflict “would never have happened” had he been re-elected in 2020.
5 March 2023: At a conservative conference, Trump claims he could resolve the war in a single day.
May 2024: Zelenskyy’s term expires, but scheduled elections are postponed under martial law due to the ongoing conflict. Zelenskyy emphasizes that “now is not the time for elections.”
22–27 September 2024: In the lead-up to the US election, Zelenskyy expresses doubts about Trump’s ability to end the war, while Trump criticizes Zelenskyy’s comments and pledges a swift resolution. The two meet in New York, agreeing that Russia cannot win.
6 November 2024: Trump is re-elected US president. Zelenskyy is among the first world leaders to congratulate him, praising his “decisive leadership” and signaling continued cooperation on the Ukraine conflict.
Oval office controversy
February 19, 2025: Weeks before their first Oval Office meeting, Trump called Zelenskyy a “dictator without elections,” criticizing Ukraine’s wartime election postponement. On Truth Social, he wrote, “I love Ukraine, but Zelenskyy has done a terrible job, his country is shattered, and MILLIONS have unnecessarily died.”
February 28: Zelenskyy visits the White House to discuss a minerals deal. Pleasantries collapse into a shouting match over Putin’s violations of peace agreements. Trump accuses Zelenskyy of “gambling with World War III” and critiques his wardrobe. Allies rally around Zelenskyy after he is asked to leave, asper Axios.
April 23–26: After Ukraine rejects a US-backed peace deal recognizing Crimea as Russian, Trump posts that Zelenskyy “has no cards to play” and urges him to “GET IT DONE.” They meet briefly at Pope Francis’ funeral, described as “very productive.”
May–July: Trump criticizes both Putin and Zelenskyy on Truth Social. Weapon shipments to Ukraine pause temporarily before $10 billion in arms is approved for NATO.
August–October: Zelenskyy returns to D.C. with European leaders for diplomatic meetings. His October visit includes the White House, energy companies, and Congress, marking a more cordial tone than his February encounter.