US President Donald Trump and Ukrainian President Volodymyr Zelensky are meeting again at the White House at a critical juncture in the war in Ukraine, with a focus on Kiev’s defense capabilities and supply of long-range weapons.

The course of relations between the two leaders from 2019 to today depicts a fragile mix of politics and cooperation, which continues to determine the fate of Ukraine.

Here is a timeline with the main points of the relations between the two leaders:

March 2019

Trump allies and others are beginning to spread a discredited, Russia-friendly theory that Ukraine conspired with Democrats to interfere in the 2016 US election to harm Trump.

April 2019

Zelensky, a comedian with no political experience and few concrete political positions, wins the presidential election in Ukraine by an overwhelming majority, overthrowing the establishment. It even secures an unprecedented parliamentary majority in early elections. He takes office on May 20.

July 25, 2019

In a famous phone conversation, Trump asks Zelensky to “do him a favor” and investigate former US Vice President Joe Biden, Hunter Biden’s son, and the theory of Ukrainian meddling in the 2016 election. This conversation led to Trump’s first impeachment. Hunter Biden had then joined the board of the Ukrainian energy company Burisma, while his father was vice chairman. He left the post in early 2016 when Trump first took office.

September 24, 2019

The US House of Representatives launches an impeachment inquiry into the Trump-Zelensky conversation. Zelensky says Trump did not try to blackmail him, while Trump rejects any accusations, calling the conversation “perfect” and the case a “democracy fraud.”

September 25, 2019

Trump and Zelensky meet for the first time in person at the UN General Assembly in New York. The US Justice Department is releasing a summary of their phone conversation, just days after a whistleblower’s complaint about the July call was published in the Washington Post.

The declassified version of the complaint is made public the following day.

The timing of the phone conversation, which took place shortly after nearly $400 million in military aid to Ukraine was frozen, raised concerns that Trump used public funds authorized by Congress as leverage for personal political gain.

February 5, 2020

The United States Senate votes to acquit Trump in his impeachment trial, 52-48, in a vote that moved clearly along party lines, rejecting the two articles of impeachment passed by the Democratic-controlled House of Representatives in December 2019.

November 7, 2020

Trump is losing his re-election bid to Joe Biden after results from several US states show the former Democratic vice president won the November 3 election. Trump, however, claims without evidence that the election was rigged.

He leaves the White House on January 20, 2021, days after his supporters stormed Capitol Hill, aimed at preventing Congress from ratifying his defeat.

Trump is leaving Washington without attending Biden’s inauguration, breaking a longstanding presidential tradition in the United States.

February 24, 2022

Russia is invading Ukraine, launching the largest military offensive in Europe since World War II.

November 5, 2024

Trump is re-elected president, defeating Vice President Kamala Harris. Zelensky is one of the first leaders to congratulate him on his “decisive leadership”.

January 20, 2025

Trump is sworn in for a second term as president, having promised to end the Russia-Ukraine war “from day one.”

February 28, 2025

The first Trump-Zelensky meeting after his re-election ends in a diplomatic crisis, causing a global backlash.

March 3, 2025

The White House announces that Trump is freezing all military aid to Ukraine.

August 18, 2025

Zelensky is visiting the White House with European leaders, days after the Trump-Putin summit in Alaska. Trump says the US will guarantee Ukraine’s security as part of an agreement to end the war, which Zelensky calls “a big step forward”. The two leaders agree that the meeting could lead to tripartite negotiations with Putin.

September 23, 2025

Zelensky speaks at the UN General Assembly and meets Trump again. Shortly thereafter, Trump dramatically changed his rhetoric on the war, stating that he believed Ukraine could regain all occupied territory and calling on Kiev to act quickly. Ukrainians treat the statements with indifference, while analysts express skepticism.

October 17, 2025

Trump welcomes Zelensky to the White House for the third time as Kiev calls for more long-range weapons.