Trump and Putin have history. That adds to the intrigue for Anchorage summit

ANCHORAGE, Alaska — President Trump has made no secret that he wants to be the one to broker an end to Russia’s war in Ukraine, touting his relationship with President Vladimir Putin as giving him the means to do so.

Now, as the two leaders prepare to meet face to face in Anchorage, Alaska, their history adds to the intrigue.

Trump said he’ll know “probably in the first two minutes” whether Putin is serious about pursuing peace. But Trump may already know the answer. When asked by a reporter this week whether he could convince Putin to stop targeting civilians in Ukraine, Trump was skeptical.

“I’ve had that conversation with him,” Trump said during an unrelated event at the Kennedy Center. “I’ve had a lot of good conversations with him. Then I go home and I see that a rocket hit a nursing home, or a rocket hit an apartment building and people are laying dead in the street.”

Putin has been widely viewed as a pariah on the world stage for more than a decade. And for nearly as long, Trump has talked about trying to work with him.

“He’s a leader of his country. I say it’s better to get along with Russia than not,” Trump told Fox News shortly after taking office in 2017.

When the interviewer pressed Trump, saying “Putin is a killer,” the president shot back.

“What, you think our country’s so innocent?” Trump said.

That wouldn’t be the last time Trump appeared to side with Putin. At times, Trump has echoed Russian propaganda about Ukraine’s responsibility for the war that Putin started, and as recently as this week suggested that “land swapping” was in order.

Trump showed Putin deference during 2018 Helsinki summit

Trump and Putin have met face to face six times over the years. The meeting that drew the most attention was a one-on-one summit in Helsinki in 2018.

Though they were on neutral territory in Finland, Trump was deferential. With cameras rolling, Trump let Putin speak first and then congratulated him on hosting a successful World Cup.

“I’ve been saying, and you’ve heard over the years, that getting along with Russia is a good thing,” Trump said. “Not a bad thing.”

He talked about his hopes for nuclear non-proliferation and even possible economic cooperation.

The moment was politically charged, with an ongoing special counsel probe of Russian interference in the 2016 presidential election. The U.S. intelligence community had determined Russia was behind the hacking of material damaging to Hillary Clinton’s campaign, and had tried to sow discord among voters.

As they stood side by side during a joint press conference, Trump said he had addressed the election interference with Putin directly, noting they “spent a great deal of time talking about it.”

Putin categorically denied the interference — and Trump appeared to side with Putin, saying “I don’t see any reason why it would be” Russia.

“I have great confidence in my intelligence people,” Trump said. “But I will tell you, President Putin was extremely powerful in his denial today.”

In Washington, the condemnation of Trump’s remarks came from across the political spectrum — and Trump tried to clarify his comment, saying he had misspoken.

At their final meeting, on the sidelines of the G20 in Osaka, Japan, in 2019, Trump and Putin were chummy, joking about having to put up with the “fake news” media. When a reporter shouted a question asking Trump whether he would tell Putin not to meddle in the 2020 election, Trump did so, but in a mocking tone as journalists were pushed out of the room.

Trump has expressed irritation with Putin recently

During the 2024 presidential campaign, Trump often boasted that he could bring an end to Russia’s war in Ukraine in 24 hours because he got along with Putin so well.

“Let me tell you, Putin went through a hell of a lot with me,” Trump shouted during a heated Oval Office meeting with Ukrainian President Volodymyr Zelenskyy in February. “He went through a phony witch hunt, where they used him and Russia – Russia, Russia, Russia.”

But Trump’s sentiments about Putin have since soured, as the fighting in Ukraine dragged on.

“We get a lot of bull**** thrown at us by Putin if you want to know the truth,” Trump said last month. “He’s very nice all the time, but it turns out to be meaningless.”

Trump began pressuring Russia, agreeing to sell powerful weapons systems to NATO intended for use by Ukraine.

He threatened to punish Russia by hiking tariffs on the main buyers of its oil exports. But just as the deadline for more sanctions approached, Putin offered this meeting. And Trump again said he thought Putin might be ready for a deal.

Trump has expressed optimism about Anchorage — even as he tempers expectations

Trump on Monday described the summit as a “feel-out meeting,” tempering expectations for a grand deal. “President Putin invited me to get involved. He wants to get involved. I think, I believe, he wants to get it over with.”

He has also suggested that a follow-up summit with both Putin and Zelenskyy could happen soon.

This week, Trump’s public statements have vacillated between close alignment with Ukraine and Europe and talking about the war in terms more sympathetic to Russia and Putin.

“We’ve seen this movie before,” said Wendy Sherman, a former deputy secretary of state who served under three Democratic presidents.

“The president seems to be on board with President Zelenskyy — and then President Putin does something that sort of woos President Trump back into the Russian fold. And that. I think, is the anxiety that most of us have,” said Sherman, now at the Belfer Center at Harvard University.

Sherman had an up-close view of how Putin operates during a four-hour meeting in 2015 with then Secretary of State John Kerry, where Putin used no notes.

Her concern is that Putin will come in with a pitch that is tailored to Trump’s transactional approach to foreign policy and his desire to rack up wins.

“I hope that President Trump feels he’s in a stronger position now as a second-term president, that he won’t fall so easily for the flattery and enticements of President Putin,” Sherman said.