WASHINGTON, D.C., USA — The first time he spoke to Volodymyr Zelenskyy, President Donald Trump tried to pressure Ukraine’s new leader to dig up dirt on Joe Biden ahead of the 2020 election. It was a 2019 phone call that eventually sparked an impeachment.

On Friday, a meeting in the Oval Office that started out with cordialities turned heated at the end, with Vice President JD Vance telling Zelenskyy to show more gratitude toward Trump, before the president himself began shouting.

“You’re gambling with the lives of millions of people,” Trump berated Zelenskyy. “You’re gambling with World War III.”

With that, Trump scrapped plans to sign an agreement that would have allowed the U.S. to access Ukraine’s rare earth minerals, a deal the U.S. president had said would have helped move the war toward a conclusion. The blowup cast new doubt on the future of U.S. support for Kyiv in fending off Russia’s invasion.

A look at the evolution of Trump and Zelenskyy’s relationship over the years:

In July 2019, Zelenskyy was anxious for a meeting with Trump at the White House, one of the Ukrainian leader’s top foreign policy priorities at the time.

During a 30-minute call, Trump dangled the possibility of a face-to-face meeting. But he also suggested that future U.S. military support for Ukraine might be contingent on its leader helping investigate business dealings there by Hunter Biden, the former vice president’s son.

The elder Biden was competing for the Democratic presidential nomination, and Trump seemed to want to weaken him 15 months out from Election Day.

Trump denied wrongdoing and began referring to his exchange with Zelenskyy as a “perfect” phone call. Even Zelenskyy later insisted that he faced “no blackmail.”

But Trump was impeached by the Democratic-controlled House in December 2019 on abuse of power and obstruction of justice charges, only the third American commander in chief to be in that situation. He was acquitted by the Senate.

Russia launched a full-scale invasion of Ukraine on Feb. 24, 2022, triggering the biggest conflict on the European continent since World War II.

Since then, the U.S. has provided more than $65 billion in military assistance to Ukraine. The Biden administration made steadfast military and political support for Zelenskyy’s country a centerpiece of his foreign policy.

As the war raged, the Biden White House staunchly defended continuing to provide support to Ukraine, even as some Republicans began grumbling about so much funding for a war that had no end in sight.

In a speech to Congress in December 2022, Zelenskyy thanked “every American” for supporting his country.

“Your money is not charity,” he said then. “It’s an investment in the global security and democracy that we handle in the most responsible way.”

Trump, then campaigning for his second term, said repeatedly that Russia would never have invaded Ukraine if he’d been president and that he’d have no trouble solving the conflict.

Upon taking office, he upended years of U.S. policy by dispatching negotiators to Saudi Arabia to meet with officials from Russian President Vladimir Putin’s government, and also began hammering out the minerals deal that he and Zelenskyy had planned to sign Friday.

Last September, Zelenskyy accompanied Biden to a Pennsylvania ammunition factory to thank the workers producing some of the most critically needed munitions for his country’s fight with Russian ground forces.

A few days later, he traveled to Trump Tower in Manhattan and discussed ending the war. In comments to Fox News Channel afterward, Trump said of the fighting, “It should stop and the president wants it to stop,” meaning Zelenskyy.

“And I’m sure President Putin wants it to stop and that’s a good combination,” Trump added. Zelenskyy invited Trump to visit Ukraine, to which Trump responded, ”I will.”

That trip came up again Friday, when Vance told Zelenskyy, “You went to Pennsylvania and campaigned for the opposition.”

Zelenskyy’s September trip was not billed as political, though, and Trump’s election opponent was Vice President Kamala Harris, not Biden. Still, Pennsylvania is a battleground state and some congressional Republicans at the time accused Democrats of using Zelenskyy’s visit to bolster Harris politically.

Last December, Trump met with Zelenskyy again during a visit to Paris to attend the reopening of the Notre Dame cathedral. It was a hastily arranged three-way meeting set up by French President Emmanuel Macron, who was trying to push the president-elect to maintain support for Ukraine in its defense against Russia’s invasion.

As president, Trump has publicly prodded Zelenskyy that he had better move quickly to negotiate an end to Russia’s war in Ukraine, or risk no longer having a country to lead. On his social media site, Trump decried Zelenskyy for not organizing an election to decide if he should remain in power — an idea backed by Russia — calling him a “ dictator without elections.”

He also suggested that Ukraine was responsible for Russia’s invasion, but later conceded that Russia was the aggressor.

Before this week, Zelenskyy had been to the White House four times — all during the Biden administration. When the Ukrainian leader announced he was coming to Washington and was ready to sign a minerals deal, Trump’s tone got more conciliatory.

He called America’s support for Ukraine against Russia’s invasion “a very worthy thing to do.” And, when pressed about having called Zelenskyy a dictator, Trump responded: “Did I say that? I can’t believe I said that. Next question.”

It all served to make Friday’s blowup all the more spectacular.