Donald Trump’s summit with Vladimir Putin in Alaska on Friday could be a decisive moment for both the war in Ukraine and the U.S. leader’s anomalous relationship with his Russian counterpart.

Trump has long boasted that he’s gotten along well with Putin and spoken admiringly of him, even praising him as “pretty smart” for invading Ukraine. But in recent months, he’s expressed frustrations with Putin and threatened more sanctions on his country.

At the same time, Trump has offered conflicting messages about his expectations for the summit. He has called it “really a feel-out meeting” to gauge Putin’s openness to a ceasefire but also warned of “very severe consequences” if Putin doesn’t agree to end the war.

For Putin, Friday’s meeting is a chance to repair his relationship with Trump and unlace the West’s isolation of his country following its invasion of Ukraine 3 1/2 years ago. He’s been open about his desire to rebuild U.S.-Russia relations now that Trump is back in the White House.

The White House has dismissed any suggestion that Trump’s agreeing to sit down with Putin is a win for the Russian leader. But critics have suggested that the meeting gives Putin an opportunity to get in Trump’s ear to the detriment of Ukraine, whose leader was excluded from the summit.

“I think this is a colossal mistake. You don’t need to invite Putin onto U.S. soil to hear what we already know he wants,” said Ian Kelly, a retired career foreign service officer who served as the U.S. ambassador to Georgia during the Obama and first Trump administrations.

Republican Sen. Lindsey Graham of South Carolina, a longtime Russia hawk and close ally of Trump’s, expressed optimism for the summit.

“I have every confidence in the world that the President is going to go to meet Putin from a position of strength, that he’s going to look out for Europe and Ukrainian needs to end this war honorably,” Graham wrote on social media.

A look back at the ups and downs of Trump and Putin’s relationship:

Russia questions during the 2016 campaign

Months before he was first elected president, Trump cast doubt on findings from U.S. intelligence agencies that Russian government hackers had stolen emails from Democrats, including his opponent Hillary Clinton, and released them in an effort to hurt her campaign and boost Trump’s.

In one 2016 appearance, he shockingly called on Russian hackers to find emails that Clinton had reportedly deleted.

“Russia, if you’re listening,” Trump said, “I hope you’re able to find the 30,000 emails that are missing.”

Questions about his connections to Russia dogged much of his first term, touching off investigations by the Justice Department and Congress and leading to the appointment of special counsel Robert Mueller, who secured multiple convictions against Trump aides and allies but did not establish proof of a criminal conspiracy between Moscow and the Trump campaign.

These days, Trump describes the Russia investigation as an affinity he and Putin shared.

“Putin went through a hell of a lot with me,” Trump said earlier this year. “He went through a phony witch hunt where they used him and Russia. Russia, Russia, Russia, ever hear of that deal?”

Putin in 2019 mocked the investigation and its ultimate findings, saying, “A mountain gave birth to a mouse.”

‘He just said it’s not Russia’

Trump met with Putin six times during his first term, including a 2018 summit in Helsinki, when Trump stunned the world by appearing to side with an American adversary on the question of whether Russia meddled in the 2016 election.

“I have great confidence in my intelligence people, but I will tell you that President Putin was extremely strong and powerful in his denial today,” Trump said. “He just said it’s not Russia. I will say this: I don’t see any reason why it would be.”

Facing intense blowback, Trump tried to walk back the comment a full 24 hours later. But he raised doubt on that reversal by saying other countries could have also interfered.

Putin referred to Helsinki summit as “the beginning of the path” back from Western efforts to isolate Russia. He also made clear that he had wanted Trump to win in 2016.

“Yes, I wanted him to win because he spoke of normalization of Russian-U.S. ties,” Putin said. “Isn’t it natural to feel sympathy to a person who wanted to develop relations with our country?”

Trump calls Putin ‘pretty smart’ after invasion of Ukraine

The two leaders kept up their friendly relationship after Trump left the White House under protest in 2021.

After Putin invaded Ukraine in 2022, Trump described the Russian leader in positive terms.

“I mean, he’s taking over a country for $2 worth of sanctions. I’d say that’s pretty smart,” Trump said at his Mar-a-Lago resort. In a radio interview that week, he suggested that Putin was going into Ukraine to “be a peacekeeper.”

Trump repeatedly said the invasion of Ukraine would never have happened if he had been in the White House — a claim Putin endorsed while lending his support to Trump’s false claims of election fraud.

“I couldn’t disagree with him that if he had been president, if they hadn’t stolen victory from him in 2020, the crisis that emerged in Ukraine in 2022 could have been avoided,” he said.

Trump also repeatedly boasted that he could have the fighting “settled” within 24 hours.

Through much of his campaign, Trump criticized U.S. support for Ukraine and derided Ukrainian President Volodymyr Zelenskyy as a “salesman” for persuading Washington to provide weapons and funding to his country.

Revisiting the relationship

Once he became president, Trump stopped claiming he’d solve the war in Ukraine in 24 hours. In March, he said he was “being a little bit sarcastic” when he said that.

Since the early days of Trump’s second term, Putin has pushed for a summit while trying to pivot from the Ukrainian conflict by emphasizing the prospect of launching joint U.S.-Russian economic projects, among other issues.

“We’d better meet and have a calm conversation on all issues of interest to both the United States and Russia based on today’s realities,” Putin said in January.

In February, things looked favorable for Putin when Trump had a blowup with Zelenskyy at the White House, berating him as “disrespectful.”

In late March, Trump still spoke of trusting Putin when it came to hopes for a ceasefire, saying, “I don’t think he’s going to go back on his word.”

But a month later, as Russian strikes escalated, Trump posted a public and personal plea on his social media account: “Vladimir, STOP!”

He began voicing more frustration with the Russian leader, saying he was “Just tapping me along.” In May, he wrote on social media that Putin “has gone absolutely CRAZY!”

Earlier this month, Trump ordered the repositioning of two U.S. nuclear submarines “based on the highly provocative statements” of the country’s former president, Dmitry Medvedev.

Trump’s vocal protests about Putin have tempered somewhat since he announced their meeting, but so have his predictions for what he might accomplish.

Speaking to reporters Monday, Trump described their upcoming summit not as the occasion in which he’d finally get the conflict “settled” but instead as “really a feel-out meeting, a little bit.”

“I think it’ll be good,” Trump said. “But it might be bad.”

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Isachenkov reported from Moscow. Associated Press writer Matthew Lee contributed to this report.

This story was originally featured on Fortune.com

© AP Photo/Evan Vucci

The Trump administration is seeking a $1 billion settlement from the University of California, Los Angeles, a White House official said Friday, weeks after the Department of Justice accused the school of antisemitism and other civil rights violations.

UCLA is the first public university to be targeted by a widespread funding freeze over allegations of civil rights violations related to antisemitism and affirmative action.

President Donald Trump’s administration has frozen or paused federal funding over similar allegations against elite private colleges. In recent weeks, the administration has struck deals with Brown University for $50 million and Columbia University for $221 million but has explored larger settlements, such as with Harvard University.

The White House official did not detail any additional demands the administration has made to UCLA or elaborate on the settlement amount. The person was not authorized to speak publicly about the request and spoke on condition of anonymity.

The Trump administration suspended $584 million in federal grants for UCLA, the university said this week. The Department of Justice’s Civil Rights Division issued a finding that UCLA violated the equal protection clause of the Fourteenth Amendment and Title VI of the Civil Rights Act of 1964 “by acting with deliberate indifference in creating a hostile educational environment for Jewish and Israeli students.”

The university had drawn widespread criticism for how it handled dispersing an encampment of Israel-Hamas war protesters in 2024. Jewish students said demonstrators in the encampment blocked them from getting to class. One night, counterprotesters attacked the encampment, throwing traffic cones and firing pepper spray, with fighting that continued for hours, injuring more than a dozen people, before police stepped in. The next day, after hundreds defied orders to leave, more than 200 people were arrested.

The University of California’s president, James B. Milliken, said in a statement Friday that the university was reviewing a document it “just received” from the Department of Justice.

“Earlier this week, we offered to engage in good faith dialogue with the Department to protect the University and its critical research mission,” Milliken said. “As a public university, we are stewards of taxpayer resources and a payment of this scale would completely devastate our country’s greatest public university system as well as inflict great harm on our students and all Californians.”

This would not be the university’s first settlement over the 2024 protests. Last month, UCLA reached a $6 million settlement with three Jewish students and a Jewish professor who sued, arguing that the university violated their civil rights by allowing pro-Palestinian protesters to block their access to classes and other areas on campus in 2024.

The settlement comes nearly a year after a preliminary injunction was issued, marking the first time a U.S. judge had ruled against a university over their handling of on-campus demonstrations against Israel’s war in Gaza.

UCLA initially had argued that it had no legal responsibility over the issue because protesters, not the university, blocked Jewish students’ access to areas. The university also worked with law enforcement to thwart attempts to set up new protest camps.

But U.S. District Judge Mark Scarsi disagreed and ordered UCLA to create a plan to protect Jewish students on campus. The University of California, one of the nation’s largest public university systems, has since created systemwide campus guidelines on protests and has said it is committed to campus safety and inclusivity and will continue to implement recommendations.

As part of the settlement, UCLA said it will contribute $2.3 million to eight organizations that combat antisemitism and support the university’s Jewish community. It also has created an Office of Campus and Community Safety, instituting new policies to manage protests on campus.

UCLA Chancellor Julio Frenk, whose Jewish father and grandparents fled Nazi Germany to Mexico and whose wife is the daughter of a Holocaust survivor, launched an initiative to combat antisemitism and anti-Israeli bias.

The Trump administration has used its control of federal funding to push for reforms at elite colleges that the president decries as overrun by liberalism and antisemitism. The administration also has launched investigations into diversity, equity and inclusion efforts, saying they discriminate against white and Asian American students.

Last month Columbia University agreed to pay $200 million as part of a settlement to resolve investigations into the government’s allegations that the school violated federal antidiscrimination laws. The agreement also restores more than $400 million in research grants.

The Trump administration plans to use its deal with Columbia as a template for other universities, with financial penalties that are now seen as an expectation.

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AP reporters Jocelyn Gecker and Julie Watson contributed to this report.

This story was originally featured on Fortune.com

© AP Photo/Damian Dovarganes, File