President Trump’s posture toward President Vladimir V. Putin of Russia over the last two decades or so has veered from admiring to infuriated, cozy to detached, and it is unclear which approach he will take on Friday when they meet in Anchorage.
This would be at least their seventh known face-to-face encounter, and the first of Mr. Trump’s second term. Here’s a look at some of the past meetings, and what the two have said about each other over the years:
The Early Years
In 2007, after Time magazine selected Mr. Putin as its “Man of the Year,” Mr. Trump wrote him a congratulatory letter. “As you probably have heard, I’m a big fan of yours!” Mr. Trump wrote.
Six years later, Mr. Trump took the Miss Universe contest to Moscow. Months before the pageant, which he owned at the time, he wondered on social media if Mr. Putin would attend, and if so, “will he become my new best friend?”
Mr. Putin did not attend.
The 2016 Presidential Campaign
Soon after he formally announced a run for the White House in 2015, Mr. Trump told reporters in July that he would “get along very well with Vladimir Putin.”
The exchange of compliments continued that year, when Mr. Putin called Mr. Trump “a very bright and talented man,” and Mr. Trump said that praise was a “great honor.”
In July 2016, though, Mr. Trump seemed to backtrack after saying repeatedly for years that he had a relationship with Mr. Putin. “He said one nice thing about me. He said I’m a genius. I said thank you very much to the newspaper and that was the end of it. I never met Putin,” he said.
During the final presidential debate in 2016, Hillary Clinton suggested that he would be Mr. Putin’s “puppet,” which Mr. Trump dismissed. But questions over Mr. Trump’s ties to Russia did not go away, and after he took office in January 2017, Russia’s role in the U.S. election dominated political conversation in the United States.
A U.S. intelligence assessment made public that month concluded that Mr. Putin had ordered an operation to interfere in the election in an effort to “undermine public faith in the U.S. democratic process, denigrate Secretary Clinton and harm her electability and potential presidency.” Russia, the assessment said, had “developed a clear preference for” Mr. Trump.
Mr. Trump denied wrongdoing and attacked the investigation.
The First Meetings
The first in-person meeting between the two leaders took place at the Group of 20 summit in Hamburg, Germany, where Mr. Trump asked Mr. Putin about Russian interference in the election. Mr. Putin denied any involvement. After the meeting, Mr. Trump took his interpreter’s notes and instructed him not to brief anyone.
They met again in November that year, in Vietnam, and in July 2018 in Helsinki, Finland. On both occasions, Mr. Putin denied interfering in the 2016 election. In Helsinki, Mr. Trump stood beside Mr. Putin and challenged the conclusion of his own intelligence agencies about Russian election interference.
Later in 2018, the two leaders spoke informally at dinner during a G20 meeting in Argentina. Little information emerged about that discussion.
They met once more before the end of the first Trump term, at the G20 summit in Osaka, Japan, in June 2019. By then, the special counsel Robert S. Mueller III had concluded that Russian had carried out a “sweeping and systematic” attack on American democracy.
Asked by a reporter whether he would tell Russia not to meddle in American elections, Mr. Trump said, “Yes, of course, I will.” He then turned to Mr. Putin, with a half-grin, and said, “Don’t meddle in the election, President,” as Mr. Putin chuckled.
Russian Invasion of Ukraine
In February 2022, as Russia prepared to invade Ukraine, Mr. Trump, now out of the White House, called Mr. Putin “pretty smart” during a fund-raiser.
“He’s taken over a country for $2 worth of sanctions,” Mr. Trump said, “taking over a country — really a vast, vast location, a great piece of land with a lot of people — and just walking right in.”
The next year, as he revved up another presidential campaign, Mr. Trump said he would end the war in Ukraine “before I even arrive at the Oval Office.”
Trump’s Second Term
As he began his second term, Mr. Trump expressed an interest in swiftly bringing an end to the war in Ukraine. But his relationship with President Volodymyr Zelensky of Ukraine took a nosedive in February after a fiery confrontation at the White House.
Mr. Trump and Vice President JD Vance berated Mr. Zelensky for not showing more gratitude for U.S. support, and the president said that Mr. Putin had “been through a lot with me” in enduring the “Russia hoax” — Mr. Trump’s description of the investigation into Russian election interference in 2016.
But Mr. Trump began to indicate frustration with Mr. Putin as the war proved harder to end than he had expected. “I’m not happy with Putin. I can tell you that much right now, because he’s killing a lot of people,” Mr. Trump said in July.
He appeared to soften his comments ahead of the meeting in Alaska, saying he “got along well” with Mr. Putin. He said he would know within minutes of speaking with the Russian leader on Friday if he would strike a deal to end the war.
Talya Minsberg is a Times reporter covering breaking and developing news.
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