The relationship between Donald Trump and Volodymyr Zelenskyy has been complex over the years.

Relations between the two presidents extend as far back as 2019, the year the Ukrainian leader took office.

It has since weathered the start of the war in Ukraine, Mr Trump‘s reelection and last month’s heated exchange in the Oval Office, in which Mr Zelenskyy was accused of being “disrespectful” to his country’s most powerful ally.

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Here we look back at the key moments that have helped shape the pair’s relationship and how it has changed over the years.

The ‘perfect’ phone call

One of the first times Mr Zelenskyy spoke with Mr Trump was in July 2019, months after he became president of Ukraine.

During a 30-minute phone call, the US leader suggested that in exchange for future military support for Ukraine, Mr Zelenskyy should help launch an investigation into Joe Biden’s son, Hunter.

Trump allies alleged Mr Biden had lobbied Ukraine to dismiss its top prosecutor to obstruct a probe into energy fIrm Burisma, which had Hunter Biden as one of its board members.

Mr Trumo’s request coincided with him appearing to want to weaken Mr Biden as he competed to become the Democratic nominee for the presidential election.

It was this call that formed the basis for Mr Trump’s first impeachment by the Democratic-controlled House in December 2019 on abuse of power and obstruction of justice charges.

Mr Trump denied wrongdoing at the time and referred to his exchange with Mr Zelenskyy as a “perfect” phone call. He was later acquitted by the Senate.

Mr Zelenskyy later admitted, during his first face-to-face meeting with Mr Trump on the sidelines of the United Nations General Assembly in September 2019, that there was “no blackmail” involved in the exchange.

Outbreak of war

Russia launched a full-scale invasion of Ukraine on 24 February 2022, triggering the biggest conflict on the European continent since the Second World War.

At the time, the Biden administration made steadfast military and political support for Ukraine a centrepiece of US foreign policy, which included huge sums of military assistance.

Mr Trump condemned the war as “appalling”, saying at the time that he was praying for Ukrainians. He even extended praise to Mr Zelenskyy, calling him “brave” for staying in the capital, Kyiv.

In the run-up to the 2024 presidential election, Mr Trump claimed he would be able to stop the war in 24 hours, adding that he would be able to “get it settled” before even entering the White House.

Doubting the claims, Mr Zelenskyy invited Mr Trump to Ukraine during an interview with Sky News’ US partner network, NBC News, in November 2023.

“If he can come here, I will need 24 minutes – yes, 24 minutes. Not more. Yes. Not more – 24 minutes to explain [to] President Trump that he can’t manage this war [in that time frame],” Mr Zelenskyy told Meet The Press presenter Kristen Welker.

He added at the time that he was unsure if Mr Trump would have Ukraine’s back if he were to re-enter the White House.

Meeting ahead of US election

A month before Mr Trump won the US election, Mr Zelenskyy visited him in Trump Tower, New York.

The trip, which took place in September, came after Mr Zelenskyy told the New Yorker magazine that he thought Mr Trump “doesn’t really know how to stop the war”.

He added, “many leaders have thought they could, but have been unable to do so”.

While in New York, the pair discussed ending the war, with Mr Trump telling Fox News after the meeting that Mr Zelenskyy wants fighting in his country to stop.

Mr Zelenskyy also reissued the invite for Mr Trump to visit Ukraine, to which he said he would accept.

‘Dictator without elections’

Work seemingly began on a ceasefire deal soon after Mr Trump was sworn into office.

Mr Zelenskyy said in February that he was working with a team from the Trump administration, describing the US as the “power that has the ability to not only stop the war but also help ensure the reliability of peace afterwards”.

But relations quickly seemed to turn sour when the US administration held talks with Russian officials in Riyadh, Saudi Arabia without Ukraine.

The four-and-a-half hour meeting was condemned by Kyiv, who said talks should not be held behind Ukraine’s back. Mr Zelenskyy also postponed a visit to Saudi Arabia, reportedly as a way to avoid giving the US-Russian meeting “legitimacy”.

The US-Russian meetings appeared to work as a catalyst of dwindling relations between the two presidents, with Mr Trump then suggesting that Ukraine was responsible for starting the war, adding that Mr Zelenskyy had “better move fast” or he would have no country left.

Her later called Mr Zelenskyy a “dictator without elections” – a dig at him remaining in office after Ukraine’s general election was delayed due to Russia’s invasion.

He also repeated the claim that the Ukrainian president has low approval ratings – which had already been dismissed by Mr Zelenskyy as Russian disinformation – and claimed American aid money had been misused.

That Oval Office meeting

Despite prior crosswords, relations between Mr Trump and Mr Zelenskyy appeared to be back on track near the end of February, when Ukraine said it wanted to sign a minerals deal with the US, giving them the right to $500bn (£394bn) in potential revenue from the resources.

The deal had planned to be signed during an in-person meeting in the Oval Office, but Mr Zelenskyy’s visit was cut short due to a clash in front of the world’s media.

The last 10 minutes of the almost 45-minute meeting descended into a tense back-and-forth, which began with vice president JD Vance telling Mr Zelenksyy: “I think it’s disrespectful for you to come to the Oval Office to try to litigate this in front of the American media.

“You should be thanking the President [Trump] for trying to bring an end to this conflict.”

As the Ukrainian president tried to object, Mr Trump raised his voice and told him: “You’re gambling with the lives of millions of people.

“You’re gambling with World War Three, and what you’re doing is very disrespectful to the country, this country that’s backed you far more than a lot of people say they should have.”

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The back ‘on track’ phone call

Addressing Congress a few days after the meeting in the Oval Office, Mr Trump said he had received an “important letter” from Mr Zelenskyy in which he said he would work under his leadership to reach a peace deal.

The letter appeared to echo what Mr Zelenskyy had said in a statement on social media hours after the US reported it was pausing military aid to Kyiv.

Mr Zelenskyy described the Oval Office meeting as “regrettable”, adding that it “did not go the way it was supposed to be” and it was “time to make things right”.

He also added that he was “ready to sign” the mineral deal, which had remained a sticking point between the two countries.

The pair did not have any direct contact until Wednesday, when they had an hour-long phone call.

Mr Trump described the conversation as “very good” adding that he and Mr Zelenskyy are “very much on track”.

He said most of the call was based on what he discussed with Russian President Vladimir Putin the day before.