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President Donald Trump and Russian President Vladimir Putin spoke by phone on Wednesday, a 90-minute conversation that began a new chapter in their storied history.
Their relationship during Trump's first term was dramatic and unpredictable, punctuated by unalloyed diplomatic victories for Putin and moments where Trump drew a hard line.
Here are some of the key moments and themes in the Trump-Putin relationship during Trump's first term.
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The accusation that Moscow meddled in Trump's election in 2016 loomed over his first-term interactions with Putin. The CIA and FBI both assessed that Russia intervened in the election, though Trump repeatedly cast doubt on their findings. The meddling came in the form of a bot-driven influence campaign to polarize the public and undermine the election process, attempts to disrupt voting systems, and the hacking of Democratic Party networks and staff by Russia, among other avenues, according to U.S. government assessments.
But Putin denied interference and Trump took him at his word, on the world stage. The pair appeared side by side in Helsinki in 2018 for a joint news conference, in which Trump said that Putin had delivered an "extremely strong and powerful" refutation. The investigation into Russian interference was a "total witch hunt," Trump said, contradicting his own Justice Department. "President Putin says it's not Russia. I don't see any reason why it would be," Trump later said.
Trump's words played well for Moscow: The summit was "better than super," Russia's foreign minister Sergei Lavrov said at the time. It was "fabulous," he said.
• Praise - and criticism
Trump and Putin have complimented each other's talent, intelligence and strength.
During Trump's first campaign, Putin said Trump was "a very flamboyant man, very talented."
"I will tell you that I think in terms of leadership, he's getting an ‘A,'" Trump said of Putin, while Barack Obama was still in office.
During the 2016 campaign, Trump repeatedly compared Obama to Putin, with the U.S. president consistently falling short of his Russian counterpart. Putin "has very strong control over a country," Trump said. "Certainly, in that system, he's been a leader, far more than our president has been a leader."
In September 2016, an NBC interviewer questioned Trump about his relationship with Putin. Trump said: "If he says great things about me, I'm going to say great things about him."
"To the extent that he was able to achieve success in business, this shows that he's a smart person," Putin said in a broadcast interview after Trump's first election victory.
In February 2017, Fox News's Bill O'Reilly pushed Trump on his praise for Putin. "Putin's a killer," O'Reilly said. Trump replied: "There are a lot of killers. We have a lot of killers. Well, you think our country is so innocent?"
• Syria
In his first term, Trump announced that he would withdraw U.S. forces from Syria, startling allies, handing Putin a victory and leaving in a lurch Kurdish forces that had pushed back the Islamic State. The departure of U.S. troops meant that Moscow would become the undisputed international power broker in Syria, the government of which it backed amid civil war.
Earlier that year, Trump had criticized Putin in a rare instance, blaming him for deaths in Syria under the regime of Bashar al-Assad.
• Ukraine
In 2017, the Trump administration first approved the sale of Javelin missiles and launchers to Ukraine to aid in its fight against separatists.
Two years later, Trump froze hundreds of millions of dollars in congressionally approved security assistance to Ukraine - which became a focus of later impeachment trials. The freeze came the summer of a call in which Ukrainian President Volodymyr Zelensky showed interest in more Javelins and Trump asked Zelensky for a "favor": digging up dirt on Democratic presidential candidate Joe Biden, as well as the Ukrainian business dealings of his son Hunter. Trump denied linking the ask to aid.
In 2022, no longer president, Trump made remarks in a radio appearance calling Russia's military a "peace force." He later said he was complimenting Putin's buildup on Ukraine border before the war as a negotiating tactic before he went "too far" and made the "unfortunate decision to enter Ukraine," according to Yahoo News.
On the 2024 campaign trail, Trump said repeatedly that he as president would bring an immediate end to the war between Russia and Ukraine.
• Skripal attack
Trump's response to an attempted assassination of a former Russian intelligence officer came under scrutiny in 2018.
On March 4, 2018, British citizen and ex-Russian intelligence officer Sergei Skripal and his daughter were both found near death, slumped on a park bench in the quiet English town of Salisbury.
Britain was swift and strong in its condemnation of the apparent attack as more information emerged. "This attempted murder using a weapons-grade nerve agent in a British town was not just a crime against the Skripals. It was an indiscriminate and reckless act against the United Kingdom," Prime Minister Theresa May said on March 12.
The Russian government has denied any role.
Meanwhile, Trump initially appeared reluctant to offer a tough response, according to reporting by the New York Times and The Washington Post. His administration ultimately imposed extensive sanctions on Moscow.
That October, Trump said in an interview with "60 Minutes" that Putin has "probably" been involved in assassinations and poisonings - but added: "it's not in our country."