A combination picture shows Russian President Vladimir Putin during a meeting with Arkhangelsk Region Governor Alexander Tsybulsky in Severodvinsk, Arkhangelsk region, Russia July 24, 2025.
Credit: Reuters Photo
By Anna Edgerton and Anthony Halpin
The curiously personal relationship between Donald Trump and Vladimir Putin has taken many bizarre turns from the last time they were alone in a room together without witnesses.
Their first summit meeting in seven years kicks off with the surprising and symbolically significant choice of Alaska as the venue for talks between the US and Russian presidents. As they meet to discuss ending the war in Ukraine, the Kremlin’s suggestion to hold it in a US state that once belonged to Russia hints at Putin’s sly strategy to appeal directly to Trump’s real-estate instincts and seal a grand bargain cutting others out.
Over the years, Putin has been the object of fascination for Trump, who praised his “genius” when Russia invaded its neighbor in 2022. The two appear to enjoy an easy, even playful rapport (Putin often refers to his American counterpart simply as “Donald”).
In his first term, Trump made no secret of his admiration for the strongman leader and has spoken to him at least six times since returning to the White House. "Putin went through a hell of a lot with me," he told Ukrainian President Volodymyr Zelenskiy in their infamous Oval Office clash.
For his part, Putin is known for switching from mischief to menace in a flash. After his “little green men” annexed Crimea in 2014, his answer to a pensioner asking him to take Alaska back was typical of his trolling style: “Why would you need Alaska?” he said. “It’s cold out there as well. Let's not get worked up about it.”
The world has changed dramatically since the calamitous 2018 summit in Helsinki, when Trump sided with Putin against his own officials on Russian election meddling in the 2016 presidential vote. Second-term Trump is a visibly more confident president and he’s grown frustrated with Putin’s delay tactics. Putin has been in power for more than a quarter of a century but the protracted conflict in Ukraine has dented his air of invincibility.
If the memorable moments from their past encounters are any measure, Friday’s summit promises compelling political drama whatever the outcome. Here are some of the highlights.
Hamburg, Germany: Group of 20, July 2017
The biggest issue hanging over Trump and Putin’s first major meeting was the role Russia played in interfering with the 2016 election that polls showed Hillary Clinton was favored to win. US intelligence agencies saw evidence of a Russian disinformation campaign aimed at boosting Trump, who was irritated that the legitimacy of his victory was being questioned. Moscow officials said Trump accepted Putin’s denial of any Russian role.
Russia’s incursions into Ukraine, which at the time were confined to Crimea and the eastern part of the country, were a minor topic in a bilateral that lasted more than than two hours.
Things took an unusual turn at the dinner for leaders and their spouses at the Elbphilharmonie concert hall on the banks of the Elbe River. At the end of the meal, Trump walked over to Putin and the two spoke informally for an hour. No notes. No aides.
The only record of this conversation came from the Kremlin’s Russian interpreter. Trump later criticized reports that characterized this second encounter as secretive, although it was only disclosed after other dinner participants recounted what they observed.
Da Nang, Vietnam: APEC, November 2017
Putin’s main motivation for traveling to Vietnam — rather than sending a lower ranking official — was to sit down with Trump. The Kremlin only found out on arrival that Trump had decided to cancel the meeting. The US president later agreed to meet “on the fly.” Putin bristled at the slight.
He blamed the failure of a more robust chat on a scheduling conflict and sent a warning. “This had to do with Mr. Trump’s schedule, my schedule and certain protocol formalities which our teams, unfortunately, failed to coordinate,” Putin said. “They will be punished for that.”
In Moscow, some pointed the finger at Trump’s team for trying to make up for the political fallout from the controversial dinner in Hamburg. Others recognized that Trump was under pressure not to appear too accommodating to Putin as US lawmakers and intelligence agencies continued to investigate Russian influence in the 2016 election.
Helsinki, Finland: Summit, July 2018
After speaking with Putin for roughly two hours, Trump shocked even members of his own party by saying he believed Putin over his own intelligence agencies in their assessment of Russian election influence.
He returned home to nearly universal rebukes of his performance. Republican Senator John McCain said “no prior president has ever abased himself more abjectly before a tyrant.” There was bipartisan pressure to tighten US sanctions on Russia.
Moscow, on the other hand, cheered both the tone and the outcome of the talks. Putin said the two leaders had “begun the path toward positive changes.” During the meeting, Putin secretly offered Trump a proposal to hold a referendum in the parts of eastern Ukraine held by Russian separatists. Trump later rejected the idea publicly, although Putin went ahead anyway after his full-scale invasion of Ukraine in 2022 when Trump was no longer in office.
In Helsinki, Trump also invited Putin to Washington later that fall. That meeting, however, never happened.
Paris, France: WWI Armistice Ceremony, November 2018
There was rampant speculation about whether Trump and Putin would have a substantive meeting on the sidelines of an international commemoration of the 1918 armistice that ended World War I. John Bolton, then Trump’s national security adviser, said the two did plan to meet. The Kremlin publicly played down the possibility of talks with Trump, even though Putin had met with Bolton several weeks earlier.
It was a rainy weekend. Trump and Putin took their own motorcades, skipping the soggy and somber walk to the Arc de Triomphe with other world leaders. When Putin arrived for the group photo, he first shook the hand of French President Emmanuel Macron, then German Chancellor Angela Merkel — then he shook Trump’s hand, with a brief thumbs-up.
Trump declining to meet separately with Putin was seen in Russia as a slight, but forgivable snub.
Buenos Aires, Argentina: G-20, November 2018
With no trip to Washington and no bilateral in Paris, Putin was confident that he would see Trump in Buenos Aires. Trump confirmed that plan, but then he canceled the meeting via a social media post from the plane, citing Russia’s capture of Ukrainian ships and sailors near Crimea.
Russian officials were taken aback by Trump’s affront – his second nixed meeting with Putin in less than a month – with one describing it as “really bad.” Publicly, Putin’s foreign policy adviser Yuri Ushakov insisted there was “no offense taken,” even after the Kremlin had previously talked up the Argentina meeting.
Osaka, Japan: G-20, June 2019
Putin would have to wait until the following year’s G-20 summit in Japan for his next sit-down with Trump on a day the US leader also met with four other heads of state. Speaking with reporters before the meeting, Putin noted that they hadn’t met since Helsinki. Trump lauded past meetings and said “we’ve had a very, very good relationship.”
This meeting came just two months after US Special Counsel Robert Mueller released his 448-page report on Russian election interference. He indicted two dozen Russians for social media activity and hacking Democrats. Mueller said he couldn’t charge a sitting president with a crime, according to Justice Department policy.
When asked in Osaka if he would tell Putin not to meddle in the 2020 US election, Trump said, “Yes, of course I will.” He grinned and pointed at the Russian leader and gave a light-hearted warning: “Don’t meddle in the election.” Putin played along. They also joked about fake news, with Putin smilingly telling Trump in English: “Yes, we have it too.”
Putin invited Trump to Moscow to mark the 75th anniversary of the Allied victory in World War II in 2020. That meeting never happened.
By the time 2020 came, the world was locking down as the Coronavirus pandemic took hold. Trump was voted out of office and Putin went into deep isolation, emerging with a much more hostile view of the West.