How Trump and Putin’s relationship has evolved since they first met eight years ago

By Kevin Liptak, Jeff Zeleny, CNN

Washington (CNN) — The last time President Donald Trump shared a room with Vladimir Putin, their relationship — perhaps the most scrutinized association of any two people in the entire world — was enjoying an upswing.

“We have had a very, very good relationship. And we look forward to spending some pretty good time together,” Trump said as their 2019 talks were getting underway in Japan. “A lot of very positive things going to come out of the relationship.”

Six years later, not much positive has happened when it comes to Russia and the United States. Putin invaded Ukraine a year after Trump left office. And in the months since he’s returned to the White House, Moscow has shown zero indication it will let up. Trump, once hopeful he might leverage his relationship with Putin into an end to the war, has grown disillusioned with his onetime friend, whom he now accuses of peddling “bullshit” over the telephone.

That makes for an altogether darker backdrop to Friday’s encounter between Trump and Putin in Alaska, their seventh face-to-face meeting and the first of Trump’s new presidency.

“There’s a realistic adjustment and lowering of expectations,” said John Herbst, a former US ambassador to Ukraine and senior director of the Atlantic Council’s Eurasia Center. “Even Trump is pointing out, correctly, that maybe you can’t trust Putin.”

Like all of Trump’s previous meetings with Putin, the sit-down at a US air base north of Anchorage comes with a degree of uncertainty about what will be said, which outcomes will be agreed to and how it will be spun afterward. Already, the White House has lowered expectations for what it describes as a “listening exercise,” even as Trump remains cautiously optimistic for progress. Moscow, meanwhile, insists a whole litany of topics meant to normalize US-Russia ties are up for discussion.

At the center of it all will be two men with a decidedly tangled relationship — long scrutinized, often secretive and never quite fully understood, even by some of Trump’s closest allies, who scratch their heads every time he seems to parrot a Kremlin talking point.

In the eight years since the leaders first sat down together on the sidelines of a Group of 20 summit in Germany, the ties between the men have zigged and zagged. Trump has heaped praise on Putin and adopted his views, but he’s also abruptly canceled meetings in anger and told other leaders he thinks Putin has changed for the worse, advisers have said.

If there has been one constant, it is the shadow of the 2016 election, in which US intelligence agencies found Russia sought to interfere on Trump’s behalf.

Those findings — and the attempts from Congress and other officials to hold individuals accountable — have colored Trump’s view of Russia and Putin for years. He has voiced a certain kinship with the Russian leader for having to endure what Trump calls the “Russia hoax.” Just this summer, he threatened criminal prosecution against officials in the Obama administration — including former President Barack Obama himself — for issues related to the probe.

“It was a strain on the relationship,” Trump said Wednesday of the investigations into Russian election interference. He added: “It made it very dangerous for our country, because I was unable to really deal with Russia the way we should have been.”

Indeed, the election meddling was a shadow over each of Trump’s previous meetings with Putin, including their inaugural session at the Hamburg G20 in 2017. Those talks lasted more than two hours, with only Trump’s Secretary of State Rex Tillerson in the room.

Afterward, Trump asked his interpreter for his notes to ensure the contents of the discussion weren’t revealed. And at a leaders’ dinner at the same summit, Trump sought out Putin for another hour-long talk — this time, without any other American officials nearby and only Putin’s interpreter to translate.

The two men would meet again several times after that, including at an Asian leaders’ summit in Da Nang, Vietnam. Trump said afterward that Putin again denied interfering in the US election — and indicated he believed him.

“I really believe that when he tells me that, he means it,” Trump said.

When Putin was reelected the next year, Trump congratulated him on his victory — despite a warning in all-capital letters from his national security team to “DO NOT CONGRATULATE” given questions about the fairness of the heavily managed contest.

Putin’s isolation on the world stage

Putin, 72, has stood the test of time through five American presidencies.

Long gone are the days of strolling through Moscow with Bill Clinton or visiting George W. Bush at his Texas ranch, where Bush glowingly said of Putin: “I was able to get a sense of his soul.”

But the Russian leader has grown increasingly isolated over the last decade, punished by much of the world for his 2014 invasion of Ukraine and Crimea, the downing of a Polish plane, a deadly nerve agent attack in the United Kingdom and far more atrocities.

An attempted reset — complete with big red prop button — with Obama failed, and Russia was ultimately expelled from the Group of Eight nations.

Before being elected in 2016, Trump claimed to have been “stablemates” with Putin ahead of an appearance on “60 Minutes,” though no evidence of the encounter ever materialized.

After Trump came into office, Putin sought to restore his place on the world stage, through a marquee summit in Helsinki. That face-to-face meeting in 2018 only intensified a Russia cloud that would hang over Trump for the remainder of his first term and carry over into Putin’s lone summit with Joe Biden in 2021. Eight months later, Putin launched another war with Ukraine that still rages on.

It was that Helsinki meeting, where Trump met with Putin behind closed doors without advisers, that fueled skepticism that is still alive today about his ability to stand up to the autocratic Russian leader. Trump faced an onslaught of bipartisan fury – and global condemnation – for accepting Putin’s word over considerable evidence from the US intelligence community that Russia interfered in an American election.

“We all think back to that really unsettling press conference in Helsinki where President Trump seemed to defer to Putin above the analysis of his own intelligence community,” said Ret. Admiral James Stavridis, former NATO Supreme Allied Commander. “I truly hope that doesn’t happen. I don’t think it will.”

It was a rare time in Trump’s presidency where he admitted a mistake, saying after returning to the White House that he “realized there is some need for clarification” about his Helsinki remarks.

But seven years later, after repeatedly striking a conciliatory tone toward Putin and touting his deep relationship with the Russian leader, Trump sounds far more skeptical at the prospect of reaching a deal over Ukraine. This pivot only came in May, when Trump suggested he would travel to Turkey to preside over a meeting with Putin and Ukrainian President Volodymyr Zelensky.

“Nothing’s going to happen until Putin and I get together, ok?” Trump said.

When that meeting never materialized, and Russia intensified its bombing campaign on Ukraine, Trump began souring on Putin and lowering expectations for his long-standing promise to end the war.

“I’m not happy with Putin,” Trump said last month in one of his sharpest sentiments yet toward the Russian leader. “We get a lot of bullshit thrown at us by Putin, if you want to know the truth. He’s very nice, all the time, but it turns out to be meaningless.”

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