Dasha Litvinova, The Associated Press

Bilateral meetings between Russian President Vladimir Putin and his U.S. counterparts were a regular occurrence early in his 25-year tenure.

But as tensions mounted between Moscow and the West following the illegal annexation of Ukraine’s Crimean Peninsula in 2014 and allegations of meddling with the 2016 U.S. elections, those meetings became increasingly less frequent, and their tone appeared less friendly.

Here’s what to know about past meetings between Russian and U.S. presidents:

Putin and Joe Biden

Putin and Joe Biden met only once while holding the presidency –- in Geneva in June 2021.

Russia was massing troops on the border with Ukraine, where large swaths of land in the east had long been occupied by Moscow-backed forces; Washington repeatedly accused Russia of cyberattacks. The Kremlin was intensifying its domestic crackdown on dissent, jailing opposition leader Alexei Navalny months earlier and harshly suppressing protests demanding his release.

Putin and Biden talked for three hours, with no breakthroughs. They exchanged expressions of mutual respect, but firmly restated their starkly different views on various issues.

They spoke again via videoconference in December 2021 as tensions heightened over Ukraine. Biden threatened sanctions if Russia invaded, and Putin demanded guarantees that Kyiv wouldn’t join NATO –- something Washington and its allies said was a nonstarter.

Another phone call between the two came in February 2022, less than two weeks before the full-scale invasion. Then the high-level contacts stopped cold, with no publicly disclosed conversations between them since the invasion.

Putin and Donald Trump

Putin met Trump met six times during the American’s first term -– at and on the sidelines of G20 and APEC gatherings — but most famously in Helsinki in July 2018. That’s where Trump stood next to Putin and appeared to accept his insistence that Moscow had not interfered with the 2016 U.S. presidential election and openly questioned the firm finding by his own intelligence agencies.

His remarks were a stark illustration of Trump’s willingness to upend decades of U.S. foreign policy and rattle Western allies in service of his political concerns.

“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.”

Since Trump returned to the White House this year, he and Putin have had about a half-dozen publicly disclosed telephone conversations.

Putin and Barack Obama

U.S. President Barack Obama met with Putin nine times, and there were 12 more meetings with Dmitry Medvedev, who served as president in 2008-12. Putin became prime minister in a move that allowed him to reset Russia’s presidential term limits and run again in 2012.

Obama traveled to Russia twice — once to meet Medvedev in 2009 and again for a G20 summit 2013. Medvedev and Putin also traveled to the U.S.

Under Medvedev, Moscow and Washington talked of “resetting” Russia-U.S. relations post-Cold War and worked on arms control treaties. U.S. State Secretary Hillary Clinton famously presented a big “reset” button to Foreign Minister Sergey Lavrov at a meeting in 2009. One problem: instead of “reset” in Russian, they used another word meaning “overload.”

After Putin returned to office in 2012, tensions rose between the two countries. The Kremlin accused the West of interfering with Russian domestic affairs, saying it fomented anti-government protests that rocked Moscow just as Putin sought reelection. The authorities cracked down on dissent and civil society, drawing international condemnation.

Obama canceled his visit to Moscow in 2013 after Russia granted asylum to Edward Snowden, a former National Security Agency contractor and whistleblower.

In 2014, the Kremlin illegally annexed Crimea and threw its weight behind a separatist insurgency in eastern Ukraine. The U.S. and its allies responded with crippling sanctions. Relations plummeted to the lowest point since the Cold War.

The Kremlin’s 2015 military intervention in Syria to prop up Bashar Assad further complicated ties. Putin and Obama last met in China in September 2016, on the sidelines of a G20 summit, and held talks focused on Ukraine and Syria.

Putin and George W. Bush

Putin and George W. Bush met 28 times during Bush’s two terms, according to the Russian state news agency Tass. They hosted each other for talks and informal meetings in Russia and the U.S., met regularly on the sidelines of international summits and forums, and boasted of improving ties between onetime rivals.

After the first meeting with Putin in 2001, Bush said he “looked the man in the eye” and “found him very straightforward and trustworthy,” getting “a sense of his soul.”

In 2002, they signed the Strategic Offensive Reductions Treaty -– a nuclear arms pact that significantly reduced both countries’ strategic nuclear warhead arsenal.

Putin was the first world leader to call Bush after the 9/11 terrorist attack, offering his condolences and support, and welcomed the U.S. military deployment on the territory of Moscow’s Central Asian allies for action in Afghanistan.

He has called Bush “a decent person and a good friend,” adding that good relations with him helped find a way out of “the most acute and conflict situations.”

Putin and Bill Clinton

Bill Clinton traveled to Moscow in June 2000, less than a month after Putin was inaugurated as president for the first time in a tenure that has stretched to the present day.

The two had a one-on-one meeting, an informal dinner, a tour of the Kremlin from Putin, and attended a jazz concert. Their agenda included discussions on arms control, turbulence in Russia’s North Caucasus region, and the situation in the Balkans.

At a news conference the next day, Clinton said Russia under Putin “has the chance to build prosperity and strength, while safeguarding that freedom and the rule of law.”

The two also met in July of that same year at the G8 summit in Japan, in September — at the Millennium Summit at the U.N. headquarters in New York, and in November at the APEC summit in Brunei.

In an interview with former Fox News host Tucker Carlson last year, Putin said he asked Clinton in 2000 if Russia could join NATO, and the U.S. president reportedly said it was “interesting,” and, “I think yes,” but later backtracked and said it “wasn’t possible at the moment.” Putin used the anecdote to illustrate his point about the West’s hostility toward Russia, “a big country with its own opinion.”

“We just realized that they are not waiting for us there, that’s all. OK, fine,” he said.

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Associated Press writer Yuras Karmanau contributed.

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