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The Evolving Dynamics of Trump and Zelenskyy’s Relationship: From ‘Perfect’ Phone Call to Oval Office Confrontation | US News


The connection between Donald Trump and Volodymyr Zelenskyy has been intricate over the years.

The interactions between the two leaders date back to 2019, the year Zelenskyy assumed the presidency of Ukraine.

This relationship has endured the onset of the war in Ukraine, Trump’s reelection efforts, and last month’s intense confrontation in the Oval Office, where Zelenskyy faced accusations of being “disrespectful” to a key ally of his nation.

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Here, we revisit significant events that have influenced the evolution of their relationship over the years.

The ‘perfect’ phone call

One of the initial conversations between Zelenskyy and Trump occurred in July 2019, just months after Zelenskyy took office.

During a 30-minute call, the U.S. president suggested that for future military assistance to Ukraine, Zelenskyy should initiate an investigation into Joe Biden’s son, Hunter.

Trump’s allies claimed Biden had pressured Ukraine to dismiss its chief prosecutor to hinder an investigation into the energy company Burisma, which had Hunter Biden on its board.

Ukraine's President Volodymyr Zelenskiy greets U.S. President Donald Trump during a bilateral meeting on the sidelines of the 74th session of the United Nations General Assembly (UNGA) in New York City, New York, U.S., September 25, 2019. REUTERS/Jonathan Ernst
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Zelenskyy and Trump first met at the United Nations General Assembly in 2019. Pic: Reuters

Trump’s request came at a time when he seemed to aim at undermining Biden’s position as he sought the Democratic nomination for the presidential election.

This phone call ultimately led to Trump’s first impeachment by the Democratic-majority House in December 2019 on charges of abuse of power and obstruction of justice.

Part of the transcript of the phone call between U.S. President Donald Trump and Ukrainian President Volodymyr Zelenskiy is displayed during the testimony of Democratic staff counsel Daniel Goldman during a House Judiciary Committee hearing to receive counsel presentations of evidence on the impeachment inquiry into U.S. President Donald Trump on Capitol Hill in Washington, U.S., December 9, 2019. REUTERS/Loren Elliott
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Part of the transcript of the phone call Trump and Zelenskyy that was used as evidence during the impeachment inquiry. Pic: Reuters

Trump asserted he did nothing wrong and referred to his communication with Zelenskyy as a “perfect” call. He was later acquitted by the Senate.

During their first in-person meeting at the United Nations General Assembly in September 2019, Zelenskyy stated there was “no blackmail” in their conversation.

Outbreak of war

On February 24, 2022, Russia initiated a full-scale invasion of Ukraine, marking the most significant conflict in Europe since World War II.

At that time, the Biden administration made unwavering military and political support for Ukraine a cornerstone of U.S. foreign policy, providing significant military aid.

Trump condemned the war as “appalling,” expressing that he was praying for the Ukrainian people and praised Zelenskyy for his courage in remaining in Kyiv.

U.S. President-elect Donald Trump shakes hands with Ukraine's President Volodymyr Zelenskiy inside Notre-Dame de Paris Cathedral, ahead of a ceremony to mark the re-opening of the landmark cathedral following the 2019 fire, in Paris, December 7, 2024. LUDOVIC MARIN/Pool via REUTERS
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Trump shakes hands with Zelenskyy in Paris’s Notre-Dame cathedral. Pic: Reuters

As the 2024 presidential election approached, Trump asserted he could end the war within 24 hours, stating he would “get it settled” before even taking office.

Skeptical of Trump’s claims, Zelenskyy extended an invitation for him to visit Ukraine during an interview with Sky News’ 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 timeframe],” Zelenskyy told Meet The Press host Kristen Welker.

He also expressed uncertainty about whether Trump would support Ukraine if he were to return to the White House.

Meeting ahead of US election

A month before Trump’s successful bid for the U.S. presidency, Zelenskyy visited him at Trump Tower in New York.

This visit occurred in September after Zelenskyy was quoted in the New Yorker stating he believed Trump “doesn’t really know how to stop the war.”

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

FILE PHOTO: Republican presidential nominee and former U.S. President Donald Trump and Ukraine's President Volodymyr Zelenskiy meet at Trump Tower in New York City, U.S., September 27, 2024. REUTERS/Shannon Stapleton/File Photo
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Zelenskyy at Trump Tower right before the US election. Pic: Reuters

While in New York, they talked about ending the conflict, with Trump later informing Fox News that Zelenskyy wanted the fighting in Ukraine to cease.

Zelenskyy also reiterated his invitation for Trump to visit Ukraine, to which Trump agreed.

‘Dictator without elections’

Efforts seemingly commenced on a ceasefire agreement soon after Trump took office.

Zelenskyy indicated in February that he was collaborating with a team from the Trump administration, describing the U.S. as the “power that has the ability to not only stop the war but also help ensure peace afterwards.”

However, relations appeared to sour quickly when the U.S. administration engaged in discussions with Russian officials in Riyadh, Saudi Arabia, without including Ukraine.

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‘Dictator’ Zelenskyy ‘better move fast’

The four-and-a-half hour meeting faced backlash from Kyiv, who expressed that discussions should not occur without Ukraine’s involvement. Zelenskyy also postponed a visit to Saudi Arabia, reportedly to avoid lending “legitimacy” to the U.S.-Russia talks.

The U.S.-Russia meetings seemed to spark a decline in the relationship between the two leaders, with Trump suggesting that Ukraine bore responsibility for initiating the war and stating that Zelenskyy needed to “move fast” or risk losing his country.

He subsequently labeled Zelenskyy a “dictator without elections“—a remark on his position remaining intact after Ukraine postponed its general election due to the Russian invasion.

Trump also reiterated claims of Zelenskyy having low approval ratings—an assertion Zelenskyy dismissed as Russian disinformation—and alleged that American aid had been misallocated.

That Oval Office meeting

Despite some tension previously, the relationship between Trump and Zelenskyy seemed to improve toward the end of February, when Ukraine expressed a desire to sign a minerals agreement with the U.S., potentially yielding $500bn (£394bn) in revenue.

The deal was set to be finalized during an in-person meeting in the Oval Office; however, Zelenskyy’s visit was cut short due to a public confrontation.

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Trump and Zelenskyy’s body language analysed

The concluding moments of the nearly 45-minute meeting turned tense, initiated by Vice President JD Vance, stating, “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 Zelenskyy attempted to respond, Trump raised his voice, asserting, “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 has supported you much more than a lot of people claim they should have.”

Read more:
What could be the future of Ukraine?
Sky’s correspondents react to Trump-Putin phone call

Apology letter

A few days after the Oval Office meeting, Trump informed Congress he had received an important letter” from Zelenskyy, in which he expressed a willingness to work under Trump’s leadership to achieve a peace agreement.

The letter seemingly mirrored comments made by Zelenskyy in a social media statement shortly after the U.S. announced a halt in military aid to Kyiv.

Zelenskyy described the Oval Office encounter as “regrettable”, stating that it “did not go as it should have” and it was “time to make things right”.

He reiterated his readiness to sign the mineral deal, which had been a contentious issue between the two nations.

The two have not had any direct communication since, with a phone call occurring on Wednesday to discuss the details of Trump’s conversation with Russian President Vladimir Putin the day prior.



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