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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.

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

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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Pic: Reuters

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.

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

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.

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

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”.

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, 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.

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‘Dictator’ Zelenskyy ‘better move fast’

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.

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Trump and Zelenskyy’s body language analysed

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.

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Donald Trump says he wants to meet North Korea’s Kim Jong Un again – as soon as ‘this year’

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Donald Trump says he wants to meet North Korea's Kim Jong Un again - as soon as 'this year'

Donald Trump has said he wants to meet North Korean leader Kim Jong Un again.

Speaking at the White House as he held talks with the new South Korean president Lee Jae Myung, Mr Trump told reporters: “I’d like to meet him this year… I look forward to meeting with Kim Jong Un in the appropriate future.”

“I’d like to have a meeting. I got along great with him,” President Trump said, adding they “became very friendly” during his first term in office.

“We think we can do something in that regard,” he said, adding that he would like to help the relationship between the two Koreas.

Trump and Kim at the demilitarized zone in June 2019. Pic: Reuters
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Trump and Kim at the demilitarized zone in June 2019. Pic: Reuters

Mr Trump and Mr Kim held three meetings between 2018 and 2019 during Mr Trump’s first term and exchanged a number of, what the president called, “beautiful” letters.

In June 2019, Mr Trump briefly stepped into North Korea from the demilitarized zone (DMZ) with South Korea.

The US president on Monday responded to a question about whether he would return to the DMZ by fondly recalling the last time he did so.

“Remember when I walked across the line and everyone went crazy?” especially the Secret Service, Mr Trump told reporters in the Oval Office.

But “I loved it”, Mr Trump said. He added he felt safe because he had a good relationship with Mr Kim.

Mr Trump met South Korea's Lee Jae Myung at the Oval Office on Monday. Pic: Reuters
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Mr Trump met South Korea’s Lee Jae Myung at the Oval Office on Monday. Pic: Reuters

Mr Trump became the first sitting American president to set foot on North Korean soil six years ago.

However, little progress was made in curbing North Korea’s nuclear programme, and Mr Trump acknowledged in March this year that Pyongyang is a “nuclear power”.

Kim possible: Is Trump seeking another ‘Hermit Kingdom’ handshake?

It was Donald Trump’s first meeting with the new president of South Korea.

A highly unconventional platform for glowing words about the North Korean one.

He said he got along “great” with Kim Jong Un and would like to meet him again “this year”.

The US president’s renewed interest in North Korea appears less about policy and more about theatrics.

The historic image of President Trump stepping on to North Korean soil in 2018 gave him global headlines.

The timing is curious – North Korea has been busy polishing its nuclear credentials and vowing not to disarm without serious concessions.

In other words, Pyongyang is holding the same cards it held four years ago, only now they’re shinier.

But Trump seems eager to revive his image as the only US president bold, or brash, enough to break bread with the ruler of the “Hermit Kingdom”.

Supporters call it visionary diplomacy; critics call it reality TV masquerading as foreign policy.

Either way, President Trump clearly sees value in the spectacle.

Whether Kim Jong Un does is another story.

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Since Mr Trump’s first-term meetings with Mr Kim ended, North Korea has shown no interest in returning to talks.

The White House said in June that Mr Trump would welcome communications with Mr Kim.

The attempts at rapprochement come after the election in South Korea of Mr Lee, who has pledged to reopen dialogue with North Korea.

As a gesture of engagement in June, Mr Lee suspended South Korean loudspeakers blasting music and messages into the North at the DMZ along their shared border.

Analysts say, however, that engaging North Korea will likely be more difficult for both Mr Lee and Mr Trump than it was in the president’s first term.

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Since then, North Korea has significantly expanded its nuclear weapons and ballistic missile programmes.

And it has developed close ties with Russia through direct support for Moscow’s war in Ukraine, with Pyongyang providing both troops and weaponry.

Mr Kim told Russian President Vladimir Putin that his country will always stand with Moscow, state media reported in June.

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Lil Nas X pleads not guilty after being charged with assaulting police officer

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Lil Nas X pleads not guilty after being charged with assaulting police officer

US rapper Lil Nas X has pleaded not guilty after being charged with assaulting a police officer while walking in downtown Los Angeles in his underwear.

The musician, real name Montero Lamar Hill, was taken to hospital and arrested after police responded to reports of a naked man shortly before 6am on Thursday.

The district attorney’s office said on Monday that Lil Nas X faces three counts of battery with injury on a police officer and one count of resisting an executive officer.

He was being held on a $75,000 (£55,457) bail, conditional on attending drug treatment. It is not immediately clear whether he had posted it and been released yet.

He is set to return to court on 15 September for his next pre-trial hearing.

Pic: AP
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Pic: AP

During the hearing on Monday, Hill’s lawyer Christy O’Connor told the judge he had led a “remarkable” life, adding: “Assuming the allegations here are true, this is an absolute aberration in this person’s life.

“Nothing like this has ever happened to him.”

A law enforcement source told Sky’s US partner network, NBC News, on Thursday that the Old Town Road and Industry Baby hitmaker punched an officer twice in the face during the encounter.

The source added officers were unsure whether he was on any substances or in mental distress.

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NBC News cited TMZ footage where Hill was seen walking down the middle of Ventura Boulevard at 4am on Thursday in a pair of white briefs and cowboy boots.

In the videos, Hill tells a driver to “come to the party” in one clip and in another tells the person: “Didn’t I tell you to put the phone down?”

“Uh oh, someone’s going to have to pay for that,” Hill says as he continues to walk away.

In some clips, Hill struts as if he’s on a catwalk, posing for onlookers, and at one point he places an orange traffic cone on his head.

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Kilmar Abrego Garcia: Man wrongly deported from US to El Salvador detained by ICE again

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Kilmar Abrego Garcia: Man wrongly deported from US to El Salvador detained by ICE again

A man who was wrongly deported from the US to El Salvador has been detained by Immigration and Customs Enforcement (ICE) again.

Kilmar Abrego Garcia, a 30-year-old originally from El Salvador, handed himself into the ICE field office in Baltimore, Maryland, for a check-in on Monday.

The visit was a mandatory condition of his release from federal custody earlier this weekend. However, in a court filing on Saturday, his lawyers said they expected Garcia would be detained again upon attending.

Garcia is charged in an indictment, filed in federal court in Tennessee, with conspiring to transport illegal immigrants into the US.

An emotional Kilmar Abrego Garcia appears outside the ICE Baltimore field office on 25 August 2025. Pic: Reuters
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An emotional Kilmar Abrego Garcia appears outside the ICE Baltimore field office on 25 August 2025. Pic: Reuters

According to a court filing by his lawyers, immigration officials made an offer to Garcia to be deported to Costa Rica in exchange for pleading guilty to the charges.

Otherwise, they would seek to deport him to Uganda.

Pics: Reuters
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Pics: Reuters

Speaking at a news conference outside the ICE office on Monday morning, Garcia said via a translator: “This administration has hit us hard, but I want to tell you guys something: God is with us, and God will never leave us.

“God will bring justice to all the injustice we are suffering.”

Simon Sandoval-Moshenberg, one of Garcia’s lawyers, also said: “There was no need to take him into ICE detention… the only reason they took him into detention was to punish him.”

A judge later ruled Garcia could not be deported after he filed a challenge asking to be allowed due process to fight any removal attempt.

Judge Paula Xinis ruled the 30-year-old must remain detained in the US until she can hold an evidentiary hearing – set for Wednesday.

She added there appeared to be “several grounds” for her to have jurisdiction to exercise relief, including that Uganda has not agreed to offer Garcia protections, such as being able to walk freely, being given refugee status, and not being re-deported to El Salvador.

After initially being detained in Maryland – where he lived with his American wife and children – by ICE in March, Garcia was sent to El Salvador, where he was then imprisoned in the country’s maximum security Terrorism Confinement Center (CECOT).

This was despite an immigration judge’s 2019 order granting him protection from deportation after finding he was likely to be persecuted by local gangs if he was returned to his native country.

Garcia was first detained by ICE in March. Pic: CASA/AP
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Garcia was first detained by ICE in March. Pic: CASA/AP

The Trump administration admitted deporting Garcia was an “administrative error”, but said at the time they could not bring him back as they do not have jurisdiction over El Salvador.

After eventually returning him to the US in June, the Trump administration detained Garcia on criminal charges that were filed in May.

The criminal indictment alleges Garcia worked with at least five co-conspirators to bring immigrants to the US illegally and transport them from the border to other destinations in the country.

Minutes after his release on Friday, officials notified Garcia they intended to deport him to Uganda.

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Homeland Security secretary Kristi Noem, US President Donald Trump, vice president JD Vance and other officials claim Garcia was a member of MS-13 – an international criminal gang formed by immigrants who had fled El Salvador‘s civil war to protect Salvadoran immigrants from rival gangs.

Garcia’s lawyers strongly deny the claims.

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