• Foreign & Public Diplomacy
• United States
• Russia
• Christina Lu

August 13, 2025, 5:40 PM

When U.S. President Donald Trump meets with Russian President Vladimir Putin in Alaska on Friday for high-stakes talks, Trump will be coming face-to-face with a shrewd leader who has dealt with his fair share of U.S. presidents.

In Anchorage, the two presidents are set to discuss the future of Russia’s full-scale invasion of Ukraine—which began nearly three and a half years ago—without Ukrainian President Volodymyr Zelensky at the negotiating table. But in the days ahead of the talks, Trump has downplayed expectations for any breakthrough, telling reporters last Friday that he planned to “see what [Putin] has in mind.”

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

It won’t be the first time that Trump and Putin are meeting in person, and Trump is far from the first American leader to hold talks with the Russian strongman. After more than 25 years in power, Putin has met with multiple U.S. presidents amid fraught geopolitical circumstances—experiences that experts say have shaped him into a seasoned and sharp negotiator.

Putin is a “very clever” negotiator, said Daniel Fried, a former U.S. ambassador to Poland who is currently at the Atlantic Council. “He’s excellent at bullshit.”

“The Russians will pitch their level of bullshit based on their assessment of their interlocutor’s level of ignorance,” Fried added.

Friday’s summit may be the two leaders’ first face-to-face meeting since Trump returned to the Oval Office, but they are no strangers. Trump and Putin met six times during the U.S. leader’s first term in office. In one of the most memorable cases, the two leaders met privately for nearly two hours in Helsinki in 2018. In a news conference afterward, Trump—while standing next to Putin—appeared to accept the Russian leader’s denial that his country had interfered in the 2016 U.S. presidential election, publicly contradicting U.S. 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.”

At the time, Trump’s remarks drew sharp rebukes from top Republicans, who expressed shock and anger at the president’s statements. One of the most vocal critics was the late Sen. John McCain, who lambasted it as “one of the most disgraceful performances by an American president in memory” in a statement.

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

In contrast, former President Joe Biden met with Putin in person only once during his presidency. The two leaders met in Geneva in June 2021 for a high-level summit where the agenda was dominated by issues of arms control and cybersecurity. The next year, the Kremlin would launch its full-scale invasion of Ukraine.

In his eight years in office, former U.S. President Barack Obama met with Putin nine times. He also met 12 times with Dmitry Medvedev—a member of Putin’s party who was briefly made the Russian president between 2008 and 2012 in a move that allowed Putin to circumvent constitutional term limits and again take office in 2012.

Under Obama’s tenure, U.S.-Russia relations were strained by the Kremlin’s accusations that the State Department was instigating protests against Putin as well as Russia’s decision to grant temporary asylum to American whistleblower Edward Snowden. Tensions deepened in 2014, when Russia illegally annexed Crimea, and in 2015, when the Kremlin militarily intervened in Syria to back the regime of President Bashar al-Assad.

In his 2020 memoir, A Promised Land, Obama compared Putin to the powerful Chicago ward bosses that he faced earlier in his career—“except with nukes and a U.N. Security Council veto.”

“Putin did, in fact, remind me of the sorts of men who had once run the Chicago machine or Tammany Hall [a historical New York City political organization]—tough, street-smart, unsentimental characters who knew what they knew, who never moved outside their narrow experiences, and who viewed patronage, bribery, shakedowns, fraud, and occasional violence as legitimate tools of the trade,” Obama wrote.

Obama’s predecessor, President George W. Bush, met with Putin a whopping 28 times during his eight years in office. Bush appeared taken with his Russian counterpart’s character, famously declaring that he got “a sense of his soul” after their first meeting in 2001.

“I looked the man in the eye. I found him to be very straightforward and trustworthy,” Bush said at a press conference. “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.”

After the terrorist attacks of Sept. 11, 2001, Putin was reportedly the first world leader to telephone Bush to express his condolences. In 2002, the two leaders inked a nuclear arms pact, the Strategic Offensive Reductions Treaty.

Putin’s first-ever meeting with a U.S. leader was with President Bill Clinton, who traveled to Moscow for talks in June 2000. In a press conference afterward, Clinton said that the two leaders shared common interests such as nonproliferation and arms control but clashed over Moscow’s actions in Chechnya. Both leaders reached an agreement to each destroy 34 tons of military-grade plutonium and establish a joint data exchange center, Clinton said.

The two leaders met as presidents a total of four times.

In 2023, Clinton said that he realized more than a decade ago that Russia planned to ultimately take military action in 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,” Clinton said, referring to the 1994 Budapest Memorandum, which saw Russia vow to respect Ukraine’s territorial integrity while Ukraine surrendered its nuclear arsenal.

“He said … ‘I don’t agree with it. And 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,” Clinton said.