Three years after Russia's unprovoked land, sea and air assault on Ukraine, which has reduced entire cities and towns to rubble and created a devastating war of attrition, few military analysts could have predicted that the President of the United States would go over the heads of Volodymyr Zelensky and his Western allies to negotiate directly with Vladimir Putin.
An even smaller number could have predicted that the leader of the free world would describe Zelensky as “a dictator without elections” while demanding 50 per cent of the revenue from Ukraine's rare-earth minerals and handing key concessions to Putin.
How did we get here? To answer that question, you have to go back to the start. Here's a rundown of the moments that have shaped Trump's relationship with Putin.
2013
Trump spoke positively about his dealings with Russia and its president several times in 2013.
When talk show host David Letterman asked, “Have you had any dealings with the Russians?”
Trump, then host of NBC reality show The Apprentice, responded: “Well, I’ve done a lot of business with the Russians. … They’re smart and they’re tough.”
Ahead of his trip later that year to Moscow to host the Miss Universe pageant - a competition he owned - Trump mused about Putin's possible attendance and whether they would hit it off.
“Do you think Putin will be going to The Miss Universe Pageant in November in Moscow — if so, will he become my new best friend?” Trump tweeted.
Interviewed by MSNBC ahead of the pageant, he said: “I do have a relationship [with Vladimir Putin] and I can tell you that he’s very interested in what we’re doing here today... He’s probably very interested in what you and I are saying today, and I’m sure he’s going to be seeing it in some form, but I do have a relationship with him and I think it’s very interesting to see what’s happened.”
Trump also praised Putin’s criticism of the concept of "American exceptionalism" on CNN, saying: “You think of the term [American exceptionalism] as being fine, but all of a sudden you say, what if you’re in Germany or Japan or any one of 100 different countries? You’re not going to like that term. It’s very insulting, and Putin really put it to him [President Barack Obama] about that.”
Appearing on Larry King, Trump also praised Putin for having done “a really great job outsmarting our country” - an apparent reference to Putin seizing the initiative over then-president Barack Obama during Syria's civil war.
Ukraine war: The minute-by-minute timeline of Trump's relationship with Putin as Zelensky faces darkest hour2014
On February 10, 2014, Trump reflected on his trip to Moscow to host the Miss Universe pageant.
“When I went to Russia with the Miss Universe pageant, [President Putin] contacted me and was so nice. I mean, the Russian people were so fantastic to us,” he told Fox News.
On 21 March, days after Putin held a sham referendum to justify his annexation of Crimea, Trump tweeted: “I believe Putin will continue to re-build the Russian Empire. He has zero respect for Obama or the U.S.!”
On April 12, Trump returned to Fox News, telling host Eric Bolling that Putin has "done an amazing job of taking the mantle", adding: "And he’s taken it away from the President, and you look at what he’s doing. And so smart. When you see the riots in a country because they’re hurting the Russians, OK, ‘We’ll go and take it over.’ And he really goes step by step by step, and you have to give him a lot of credit.”
During that same interview, he also spoke highly of his interaction with the Russian president during Miss Universe event, saying: “He could not have been nicer. He was so nice and so everything. But you have to give him credit that what he’s doing for that country in terms of their world prestige is very strong.”
At a New Hampshire event later that day Trump said Putin is “absolutely having a great time”, adding: “Russia is like, I mean they’re really hot stuff” and “and now you have people in the Ukraine — who knows, set up or not — but it can’t all be set up, I mean they’re marching in favour of joining Russia”.
On April 28, 2014, Trump tweeted: “Putin has shown the world what happens when America has weak leaders. Peace Through Strength!”
He also returned to his interaction with Putin at the Miss Universe event on several occasions, telling journalists on May 27 that Putin "could not have been nicer, and we had a tremendous success”.
On December 16, Trump appeared to justify a potential response from Putin over Obama's sanctions, telling Fox News host Neil Cavuto that Putin is “wounded” and that “wounded people and wounded animals can do lots of strange things and we’d better be a little bit careful”.
2015
Two months before Trump announced his candidacy for the President of the United States on June 16, 2015, Trump gave an interview to The Daily Mail in which he spoke highly of his relationship with Putin, telling the paper that “the relationship is great, and it would be great if I had the position I should have".
In that same interview, Trump revealed he'd received “a gift from Putin – an award and a beautiful letter” during his trip to Moscow.
During a trip to his golf resort in Scotland, Trump says he thinks he’d get along well with Putin:
"I think I'd get along very well with Vladimir Putin, I just think so. "People say 'what do you mean?' I think I'd get along well with him.”
Trump also said Putin “hates Obama and Obama hates him, we have unbelievably bad relationships".
On August 15, Trump said on Fox News that he would meet with Putin when the Russian president came to New York for the UN General Assembly.
“Frankly, I’d get along great with him,” he said. "You gotta get along with these people.”
In an interview with Bill O’Reilly on The O’Reilly Factor on Fox News, aired on September 29, 2015, Trump gives Putin an ‘A’ for leadership.
"I will tell you that I think in terms of leadership, he is getting an 'A,' and our president is not doing so well," Trump said. "They did not look good together."
In an interview with ABC’s This Week on December 20, 2015, Trump appears sceptical of allegations that Putin has ordered the killing of journalists who engage in political dissent.
“As far as the reporters are concerned, obviously I don’t want that to happen. I think it’s terrible—horrible. But, in all fairness to Putin, you’re saying he killed people. I haven’t seen that. I don’t know that he has. Have you been able to prove that? Do you know the names of the reporters that he’s killed? Because I’ve been—you know, you’ve been hearing this, but I haven’t seen the name. Now, I think it would be despicable if that took place, but I haven’t seen any evidence that he killed anybody in terms of reporters.”
2016
In an interview with Fox Business’ Maria Bartiromo on January 26, 2016, Trump discusses the 2006 murder of Alexander Litvinenko, a former Russian security agent, and the 2016 findings of a British inquiry that Putin “probably approved” his poisoning.
"Have they found him guilty?” Trump said. “I don't think they've found him guilty.”
“If he did it, fine. But I don’t know that he did it. You know, people are saying they think it was him, it might have been him, it could have been him. But Maria, in all fairness to Putin—I don’t know. You know, and I’m not saying this because he says, ‘Trump is brilliant and leading everybody’ —the fact is that, you know, he hasn’t been convicted of anything.”
At a news conference the following month, Trump suggested America should adopt a more doveish approach to Russia.
“You want to make a good deal for the country, you want to deal with Russia – and there’s nothing wrong with not fighting everybody, having Russia where we have a good relationship as opposed to all the stupidity that’s taken place.”
At a rally on February 16, 2016, Trump declared that he had "no relationship with Putin other than he called me a genius", adding: "He said, ‘Donald Trump is a genius and he is going to be the leader of the party and he's going to be the leader of the world or something.’”
Trump hit out at media claims that he admires Putin at a rally on March 16.
“Putin said good things about me. He said, ‘he’s a leader and there’s no question about it, he’s a genius.’ So they all said, the media, they said -- you saw it on the debate -- they said, ‘you admire President Putin.’ I said, I don’t admire him. I said he was a strong leader, which he is. I mean, he might be bad, he might be good. But he’s a strong leader.”
During a victory speech on April 26, 2016, Trump said: "We're going to have a great relationship with Putin and Russia.”
On May 27, 2016, Trump called Putin “a strong leader” at a rally.
Towards the end of the year, Trump appeared to walk back previous statements he made about his relationship with Putin, declaring at a presidential debate on October 9, 2016 that “I don’t know Putin" and at the third presidential debate on October 19th, Trump denied Hilary Clinton’s charge he was Putin’s “puppet”, saying: “No puppet. You’re the puppet.”
2017
Following Trump's shock victory, he appeared to slightly modify his messaging towards Putin while still talking up strong diplomatic ties with the country.
On January 2017, Trump said he believed Russia was responsible for the hacking the Democratic National committee in 2016: "I think it was Russia," Trump said, adding that Putin "should not be doing it.”
“He won't be doing it. Russia will have much greater respect for our country when I am leading it than when other people have led it,” Trump said.
Trump said he believed a good relationship with Putin would be an asset.
"If Putin likes Donald Trump, I consider that an asset, not a liability, because we have a horrible relationship with Russia. Russia can help us fight ISIS, which, by the way, is, number one, tricky. I mean if you look, this administration created ISIS by leaving at the wrong time. The void was created, ISIS was formed."
Facing criticism for his perceived soft stance on Russia and Putin’s authoritarianism as investigations into Russian interference in the 2016 US election gathered pace, Fox News' Bill O’Reilly wondered whether Trump thought Putin was a "killer".
Trump appeared to rebuke his remark during the Super Bowl interview on February 6, saying: “There are a lot of killers. Do you think our country is so innocent? Do you think our country is so innocent?"
Months before an investigation into Russia’s possible collusion with the Trump campaign in the 2016 US presidential election was officially launched, Trump assured CBS in April that he “would hold Putin responsible” if election meddling could be proved.
Asked about Russia’s human rights record on 60 Minutes on 15 October and whether the Putin administration had ordered the Sergei Skripal poisoning in the UK, Trump said, “probably... but it’s not our country”.
2018
During a phone call with Putin on March 20, Trump congratulated him on his victory in Russia’s highly disputed presidential election.
This went against the advice of his own national security advisers, who had reportedly written “DO NOT CONGRATULATE” in his briefing notes.
Arguably, Trump’s most controversial moment regarding Putin came on July 16, 2018 when during a press conference in Helsinki, Finland, Trump publicly sided with Putin over US intelligence agencies, which had concluded that Russia interfered in the 2016 election.
“All I can do is ask the question – my people came to me, Dan Coats [director of national intelligence] came to me and some others, they said they think it’s Russia,” he said.
“I have President Putin here, he just said it’s not Russia. I will say this, I don’t see any reason why it would be but I really want to see the server but, I have confidence in both parties.”
Facing massive backlash, Trump tried to clarify his statement the next day, telling reporters at the White House: “The sentence should have been: ‘I don’t see any reason why it wouldn’t be Russia."
While attending Armistice Day commemorations in Paris on November 11, 2018, Trump was seen briefly shaking hands with Putin and exchanging smiles.
“He is very important for Russia. He is very important for me. He is very important for the world," he told reports prior to the exchange.
2019
On May 3, 2019, Trump spoke with Putin by phone for over an hour and later described the conversation to reporters.
The call took place just weeks after Special Counsel Robert Mueller released his report, which detailed Russia’s interference in the 2016 election.
Trump claimed they did not discuss Russian interference in the 2016 election, despite the Mueller Report confirming Russian efforts to help Trump win.
“We discussed trade. We discussed Venezuela. We had a very good talk. We discussed nuclear arms control," Trump told reporters.
When asked if election interference came up, he added: “We didn’t discuss that... He [Putin] actually sort of smiled when he said something to the effect that it started off as a mountain and ended up as a mouse.”
At the G20 Summit in Osaka, Japan, Trump met face-to-face with Putin. When reporters asked about Russian election interference, Trump jokingly told Putin not to meddle in US elections.
Leading up to the G7 Summit in Biarritz, France, Trump pushed for Russia to be reinstated into what was formally known as the G8, a group it had been expelled from in 2014 after annexing Crimea.
“I think it’s much more appropriate to have Russia in. It should be the G8, because a lot of the things we talk about have to do with Russia.”
During a NATO leaders’ summit in London on December 3, 2019, Trump downplayed concerns about Russia’s aggressive actions in Ukraine and its broader threats to NATO.
“Russia wants to make a deal very much on arms control and nuclear. And that's smart. And so do we. We think it would be a good thing,” he said.
2020
After US intelligence officials briefed Congress that Russia was again interfering in the 2020 election to help Trump, the then-president lashed out on social media, tweeting: “Another misinformation campaign is being launched by Democrats in Congress saying that Russia prefers me to any of the Do-Nothing Democrat candidates... Hoax number 7!”
On March 20, 2020, during a press briefing, Trump defended Russia and Saudi Arabia amid a global oil price war that was harming US energy markets.
Instead of blaming Putin, Trump called for reducing US oil production to stabilise the market.
“I never thought I’d be saying this, but maybe we have to have an oil increase because we do. The price is so low," he told reporters.
In June 2020, reports emerged that Russian military intelligence had offered bounties to Taliban-linked militants to kill US troops in Afghanistan. Trump downplayed the intelligence.
“The Russia Bounty story is just another made up by Fake News tale that is told only to damage me.”
Just like in 2019, Trump pushed for Russia to rejoin the G7, despite opposition from European leaders.
Speaking aboard Air Force One on July 23, Trump said: “I don’t feel that as a G7 it properly represents what’s going on in the world. It’s a very outdated group of countries."
During his final debate with Joe Biden before the 2020 election, Trump praised Putin’s intelligence while attacking Biden and Ukraine, calling the Russian president "sharp".
2021
During his first major speech after leaving office, Trump referred to his relationship with Putin.
Speaking to a crowd at the Conservative Political Action Conference (CPAC) in Orlando on February 28, Trump said: “The problem with Democrats is that they always want to go after Russia. I had a good relationship with Putin.”
After Biden met with Putin in Geneva, Trump issued a statement on June 16 criticising Biden’s approach, suggesting Putin got the better deal.
“We gave a very big stage to Russia, and we got nothing. It was a good day for Russia. I don’t see what we got out of it," the statement read.
In the same statement, Trump said: "I got along great with him [Putin]. There was nobody tougher on Russia than me.”
During an interview with Sean Hannity on Fox News on October 7, 2021, Trump praised Putin while criticising Biden’s handling of Afghanistan and foreign policy.
“I got along very well with President Putin. I liked him. He liked me," he said.
As Russia began massing troops on the Ukraine border in December 2021, Trump did not initially issue a strong statement condemning Putin’s actions.
“Look, I knew Putin very well. I got along with him great. He wouldn’t have done this under my administration," he told Fox News.
2022
On February 22, just two days before Russia’s full-scale invasion of Ukraine, Trump appeared on The Clay Travis & Buck Sexton Show and praised Putin’s strategy as “smart” and “savvy”.
Speaking at CPAC (Conservative Political Action Conference) in Orlando on February 26, Trump argued that Putin would not have invaded Ukraine if he were still president.
Speaking to Sean Hannity on Fox News on April 13, Trump acknowledged Putin was struggling in Ukraine but still avoided directly condemning him.
“I’m surprised. I thought he [Putin] was negotiating when he sent troops to the border... I think he’s having a lot of trouble.”
During a rally in Alaska on July 9, Trump claimed that Putin “changed” and became more aggressive after his presidency ended.
“I think he [Putin] changed. It was a different Putin. I got along with him very well. I say he’s smart. He is smart... but I thought he was negotiating when he moved troops to the border," he told the crowd.
In an interview with John Fredericks Radio on September 1, Trump said the U.S. should push for a peace deal between Russia and Ukraine.
“This should never have happened. Russia needs to negotiate peace now, and the U.S. should be the one to broker it," he said.
In an interview with One America News on December 17, Trump appeared to make his strongest admission to date that Putin had made a mistake by invading Ukraine.
“He made a mistake. In his mind, he didn’t think it was a mistake. But he’s got a big problem. I think he’s having a harder time than he thought.”
However, critics pointed out that he still avoided calling Putin an aggressor and framed the war as a misjudgment rather than an act of unprovoked brutality.
2023
On January 27, 2023, as the Russia-Ukraine conflict escalated, Trump posted on his social media site Truth Social: "IF I WERE PRESIDENT, THE RUSSIA/UKRAINE WAR WOULD NEVER HAVE HAPPENED, BUT EVEN NOW, IF PRESIDENT, I WOULD BE ABLE TO NEGOTIATE AN END TO THIS HORRIBLE AND RAPIDLY ESCALATING WAR WITHIN 24 HOURS. SUCH A TRAGIC WASTE OF HUMAN LIFE!!!"
In a Radio Interview with Hugh Hewitt on February 27, Trump suggested that an end to war would require tough compromises on both sides.
He said: "That would mean saying things to Putin and saying things to Zelensky that they’re not gonna want to hear and getting them into a room and getting it done."
In a March interview with Fox News host Sean Hannity, Trump claimed he had deterred Putin from invading Ukraine during his presidency, implying that the war wouldn’t have happened on his watch in a thinly-veiled swipe at then-president Joe Biden.
"Putin would have never gone into Ukraine. I used to talk to him about it — I said ‘better not do it.’ And he wouldn’t have — we had a very friendly conversation about it: I said, ‘Hey, Vladimir, you can’t go into Ukraine," he told Fox News.
During the CNN Town Hall in New Hampshire on May 10, Trump suggested Europe needed to step up and could not rely solely on America to guarantee Ukrainian security.
"We’re giving away so much equipment, we don’t have ammunition for ourselves right now," he said, reiterating his pledge to end the war in 24 hours should win the election.
2024
InaninterviewwithconservativeradiohostHughHewitt,TrumpreiteratedhisclaimthatRussia’sinvasionofUkraine(ongoingsinceFebruary2022)wouldnothaveoccurredunderhispresidency.
Speaking to donors at a Mar-a-Lago fundraiser on April 12, Trump claimed he had explicitly warned Putin against invading Ukraine during his presidency.
During a nearly two-hour conversationtwith Elon Musk on his platform X in August, Trump repeated this claim, telling the tech mogul: “I told him [Putin] things that I would do. And he said, ‘no way’, and I said, ‘way.'"
In a wide-ranging three-hour interview with Joe Rogan in October, Trump repeated his assertion Russia would never have invaded Ukraine if he had been president.
“I said, ‘Vladimir, you're not going in,’” he told Rogan, referring to Russian President Vladimir Putin. “I used to talk to him all the time.
On Oct. 14 Trump called during his first presidency, that he "(got) along very well with (Russian President Vladimir) Putin," implying that the Russian leader often talked about his ambition to control Ukraine.
The comments came three weeks before the U.S. presidential election, which can have a profound impact on Washington's support for Ukraine's struggle against Russian aggression.
"I get along very well with Putin. I got; I fully understand what's happening," the Republican candidate for U.S. presidency said at a town hall event in Oaks, Pennsylvania, regarding Russia's invasion of Ukraine.
"It (Ukraine) was the apple of his eye; he used to talk about it. But I said, 'You're not going in,' and he wasn't going in."
After his election win in November, President-elect Trump said that Putin had expressed his interest in a meeting regarding the war with Ukraine.
“President Putin said that he wants to meet with me as soon as possible,” Trump said during his remarks at Turning Point’s AmericaFest convention on December 22.
“So we have to wait for this, but we have to end that war. That war is horrible, horrible.”
2025
Trump issued a stern warning to Putin on January 22, demanding an end to the war in Ukraine.
He stated that if Russia did not comply, it would face severe consequences, including increased taxes, tariffs, and sanctions on Russian goods sold to the United States and allied countries.
“Settle now, and STOP this ridiculous War! IT’S ONLY GOING TO GET WORSE,” Trump wrote on Truth Social.
“If we don’t make a ‘deal,’ and soon, I have no other choice but to put high levels of Taxes, Tariffs, and Sanctions on anything being sold by Russia to the United States, and various other participating countries,” he wrote.
In a significant policy shift on February 12, US Secretary of Defense Pete Hegseth stated that returning to Ukraine's pre-2014 borders was "an unrealistic objective" and that attempting to regain all territory "will only prolong the war".
He suggested that Ukraine must have "robust security guarantees", but NATO membership was not considered a realistic outcome of a negotiated settlement.
Later that day, Trump posted on Truth Social that he'd had a "highly productive phone call" with Putin, during which they agreed to "have our respective teams start negotiations immediately".
Trump also spoke with Zelensky, he said, assuring him of collaborative efforts to "stop Russian aggression and ensure a lasting, reliable peace".
On February 18th, American and Russian delegations, led by US Secretary of State Marco Rubio and Russian Foreign Minister Sergey Lavrov, respectively, met in Riyadh, Saudi Arabia, to develop a framework for further peace negotiations regarding the war in Ukraine.
The decision to go over the heads of Zelensky and Western allies caused outrage and dismay in Europe.
On February 19, Trump criticised Ukrainian President Zelensky on Truth Social, referring to him as a "dictator without elections" and suggesting that Ukraine was to blame for the ongoing conflict.
He wrote: "You should have never started it. You could have made a deal."
Zelensky hit back at these remarks, accusing Trump of being influenced by Russian disinformation.
On February 20, Special Envoy Keith Kellogg met with President Zelensky in Kyiv to discuss the ongoing conflict and potential peace negotiations. Despite the meeting, tensions remained high due to previous criticisms exchanged between Trump and Zelensky.
The next day, US Secretary of State Marco Rubio indicated that a potential meeting between Trump and Putin was contingent upon progress toward ending the war in Ukraine.
Rubio emphasised that the timing of such a meeting depended on Russia's commitment to ending the conflict initiated by its invasion of Ukraine three years prior.
