What past US presidents’ meetings with Putin reveal about Alaska summit?

When US President Donald Trump meets Russian President Vladimir Putin in Alaska on August 15, the encounter is far more than a routine diplomatic engagement—it is a high-stakes confrontation with a leader whose decades in power have honed him into a formidable negotiator.

As Foreign Policy writes in its analysis, the summit comes at a pivotal moment in the nearly three-and-a-half-year war in Ukraine, with Trump set to discuss the conflict without Ukrainian President Volodymyr Zelenskyy present.

Trump has tempered expectations ahead of the talks, telling reporters that he planned to “see what [Putin] has in mind.”

White House press secretary Karoline Leavitt emphasised that “the president is agreeing to this meeting at the request of President Putin. And the goal of this meeting for the president is to walk away with a better understanding of how we can end this war.”

For Putin, this is another step in a long series of interactions with US leaders. Daniel Fried, former US ambassador to Poland, told Foreign Policy that Putin is a “very clever” negotiator. 

“He’s excellent at bullshit,” Fried said, adding, “The Russians will pitch their level of bullshit based on their assessment of their interlocutor’s level of ignorance.”

Trump and Putin are not strangers, having met six times during Trump’s first term. One of the most memorable encounters came in Helsinki in 2018, where Trump—standing next to Putin—appeared to accept the Russian leader’s denial of interference in the 2016 US election, contradicting US intelligence findings.

“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.”

The comments drew sharp rebukes from senior Republicans, including the late Sen. John McCain, who condemned the remarks as “one of the most disgraceful performances by an American president in memory.”

McCain added, “The damage inflicted by President Trump’s naivete, egotism, false equivalence, and sympathy for autocrats is difficult to calculate. But it is clear that the summit in Helsinki was a tragic mistake.”

Other US presidents have approached Putin with varying degrees of caution and strategy. Former President Joe Biden met with him once in Geneva in June 2021, focusing on arms control and cybersecurity—a meeting that preceded Russia’s full-scale invasion of Ukraine.

Former President Barack Obama met with Putin nine times, navigating a relationship strained by Russia’s actions in Crimea, Syria, and asylum for Edward Snowden. Obama compared Putin to “the sorts of men who had once run the Chicago machine or Tammany Hall…except with nukes and a UN Security Council veto,” describing him as “tough, street-smart, unsentimental.”

President George W. Bush met with Putin 28 times, famously remarking after their first meeting, “I looked the man in the eye. I found him to be very straightforward and trustworthy. We had a very good dialogue. I was able to get a sense of his soul; a man deeply committed to his country and the best interests of his country.”

Finally, President Bill Clinton inaugurated US-Russia presidential diplomacy with Putin in June 2000. Clinton recalled in 2023 that he had recognised Russia’s long-term intentions toward Ukraine:

“Vladimir Putin told me in 2011—three years before he took Crimea—that he did not agree with the agreement I made with [former Russian President] Boris Yeltsin…‘I do not support it. And I am not bound by it.’ And I knew from that day forward it was just a matter of time.”

As Trump prepares to meet Putin again, analysts and former diplomats alike are watching closely, aware that this encounter is as much a test of psychological acuity as it is of diplomatic skill—an encounter with a leader who has, for decades, played the long game on the global stage.

By Sabina Mammadli