It was a meeting which will be spoken about for generations. After three years of war aided and largely funded by the arrived in Washington to sign a mineral deal which was set to preserve US backing - at least for the time being.
But as the world's media watched on, a meeting that was hoped to strengthen a difficult relationship between the new administration in the White House and Kyiv descended into chaos instead. US President spelt out the consequences of US support no longer being available, Vice President attempted to rebuke the Ukrainian leader and presented the Americans with pictures of tortured Ukrainian prisoners of war. Following the meeting, which saw raised voices and remarks uncommon in geopolitical meetings, a scheduled press conference was cancelled, with seen leaving the White House shortly after.
The Express took a look at four key moments that stood out during this momentous evening.
Perhaps it should come as no surprise after the comments heard from the Trump administration throughout the election campaign and more so in the last two weeks.
But for a US President to sit next to an "ally" in the White House and declare that he is in the middle between them and a Russian leader is a watershed moment.
He said: "I'm not aligned with Putin, I'm not aligned with anybody. I'm aligned with the United States of America."
"I am for both Ukraine and Russia, I want to get it solved," said Trump, laying out clearly a shift in US standpoint on who it is (or isn't backing) in this conflict.
"Why aren't you wearing a suit"?As a journalist, the opportunity to ask world leaders a question in the Oval Office perhaps comes around once in your career, if you're lucky.
One American journalist focused their attention on Zelensky's attire, asking the wartime leader why he was not wearing a suit.
When the Ukrainian president noted he had bigger concerns than his wardrobe at the moment, the reporter said "a lot of Americans have problems, with you not respecting office". Zelensky rebuked: "I will wear [a suit] after this war will finish. Yes, maybe, maybe something like yours, maybe some something better. I don't know, we will see."
Elon Musk has appeared in the Oval Office in a baseball cap and t-shirt on multiple occasions.
During the meeting, JD Vance intervened to say: "Mr President, with respect, I think it is disrespectful for you to come into the Oval Office and try to litigate this in front of the American media.
"Right now you guys are going around and forcing conscripts to the frontline because you have manpower problems."
He then pointed to his boss and added: "You should be thanking the President for trying to bring an end to this conflict."
When asked if he had visited , the Vice President responded: "I have actually watched and seen the stories and I know what happens is you bring people on a propaganda tour Mr President."
The sight of a US President telling the leader of an ally to "be thankful" for their help is almost unheard of in geo-political terms - especially in front of the world's media.
After accusing Zelensky of "gambling with World War 3", Trump went on to tell the Ukrainian President to "be grateful", as if he was a petulant child.
The former host of the Apprentice concluded the fiery meeting by claiming that it would "make great television", with ratings never far from the former TV personality's mind.
The scenes were extraordinary and if Zelensky was caught unaware, his face did not give it away.