As Russian President Vladimir Putin prepares for a summit in Alaska with his United States counterpart Donald Trump, he can draw on his experiences from 48 previous meetings with American presidents.

Over 25 years as Russia’s leader, Putin has met and worked with five US presidents: Bill Clinton, George W Bush, Barack Obama, Trump and Joe Biden.

While some of the earlier meetings were relatively warm, reflecting the hopes of US-Russia friendship between the end of the Cold War and the early 2000s, most of Putin’s more recent interactions — especially with Obama and Biden — have been frostier, as bilateral ties have worsened.

Here’s a recap of some of the key moments from those past meetings, and how jazz concerts and fishing trips gave way to threats.

FILE In this Saturday, July 21, 2000 file photo President Bill Clinton shares a light moment with Russian President Vladimir Putin during a tree-planting ceremony at Bankokushinryokan or "bridge to the world," before the Group of Eight meeting in Nago, Okinawa, Japan. (AP Photo/Vincent Yu, File)
Bill Clinton shares a light moment with Putin during a tree-planting ceremony before the G8 meeting in Nago, Okinawa, Japan, on July 21, 2000 [Vincent Yu/AP Photo]

June 2000: Putin-Clinton

Less than three months after he formally became president of Russia, Putin hosted US President Clinton in Moscow. The Russian leader took Clinton on a tour of the Kremlin, after which a Russian jazz group performed for them.

Clinton congratulated Putin on Russia’s decision to ratify two arms control treaties. “President Yeltsin led Russia to freedom. Under President Putin, Russia has the chance to build prosperity and strength, while safeguarding that freedom and the rule of law,” Clinton said, referring to Boris Yeltsin, Putin’s predecessor as president.

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Putin, on his part, described the US as “one of our main partners”. Moscow, he said, would never again seek confrontation with Washington. “Never. We are for cooperation. We are for coming to agreement on problems that might arise,” he said.

But Clinton acknowledged their differences over Chechnya, where Russian forces had launched a major war the previous year, after a series of apartment blasts in Russia killed more than 300 people. Moscow blamed Chechen separatists for the explosions.

The Moscow meeting was the first of four between Putin and Clinton in 2000, the others on the margins of multilateral events, before the US president left office in January the following year.

George W. Bush and Vladimir Putin during a toast at Bush ranch, Crawford, Texas, photo
George W Bush and Putin during a toast at Bush ranch, Crawford, Texas, on November 14, 2001 [AP Photo]

November 2001: Putin-Bush

After the September 11 attacks, Putin was the first world leader to call then-US President Bush and offer support. Two months later, Bush hosted Putin at his Crawford, Texas ranch, optimism about ties dripping from his words.

“When I was in high school, Russia was an enemy. Now the high school students can know Russia as a friend; that we’re working together to break the old ties, to establish a new spirit of cooperation and trust so that we can work together to make the world more peaceful,” Bush said. Bush drove Putin in a pick-up truck to a waterfall on the ranch.

But by the time they met in Russia in November 2002, US-led efforts for NATO expansion had injected unease into the relationship.

Putin holding up a fish he caught in Maine, while visiting US President George W Bush and his family on July 2, 2007 [FILE: AP Photo]
Putin holding up a fish he caught in Maine, while visiting Bush and his family on July 2, 2007 [AP Photo]

July 2007: Putin-Bush

By this point, the US invasion of Iraq in 2003 had amplified tensions between the two countries. But despite differences, Bush continued to maintain a warm personal relationship with Putin, whom he hosted at his parents’ home in Kennebunkport, Maine.

Both acknowledged areas where their views diverged, but they each credited the other with transparency.

Bush took Putin fishing. The Russian president was the only one who caught a fish on that trip – it was set free, Putin said.

FILE - In this April 6, 2008 file photo, President George Bush, left, and Russian President Vladimir Putin, look on during a press conference at the Russian Presidential residence Bochorov Ruchei, in Sochi, Russia. (AP Photo/Gerald Herbert)
Bush, left, and Putin, look on during a news conference at the Russian leader’s residence in Sochi, Russia, on April 6, 2008 [Gerald Herbert/AP Photo]

April 2008: Putin-Bush

The final meeting between Bush and Putin as presidents took place in Sochi, Russia, and was focused on US plans to expand a missile defence system in Europe that Russia was opposing.

There was no breakthrough – the two leaders agreed to disagree.

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But their personal rapport appeared intact. Bush met Putin 28 times in total. He only met British Prime Minister Tony Blair more.

FILE - In this July 7, 2009 file photo, President Barack Obama meets with then- Russian Prime Minister Vladimir Putin in Moscow. President Barack Obama and Russian President Vladimir Putin will use their first meeting Monday June 18, 2012 since Putin returned to the top job to claim leverage on their twin needs: Obama needs Russia to help, or at least not hurt, U.S. foreign policy aims in the Mideast and Afghanistan. Putin needs the United States as a foil for his argument that Russia doesn’t get its due as a great power. (AP Photo/Haraz N. Ghanbari, File)
Barack Obama meets with Putin in Moscow on July 7, 2009 [Haraz N Ghanbari/AP Photo]

July 2009: Putin-Obama

Putin was now prime minister, with ally Dmitry Medvedev the Russian president.

US President Obama met Putin during a visit to Moscow. By now, differences had grown over Russia’s invasion of Georgia in 2008, which the US had opposed.

“We may not end up agreeing on everything, but I think that we can have a tone of mutual respect and consultation that will serve both the American people and the Russian people well,” Obama told Putin.

FILE In this Monday, June 17, 2013 file photo President Barack Obama meets with Russian President Vladimir Putin in Enniskillen, Northern Ireland. (AP Photo/Evan Vucci, File)
Obama meets with Putin in Enniskillen, Northern Ireland, on June 17, 2013 [Evan Vucci/ AP Photo]

June 2013: Putin-Obama

As Obama met Putin on the margins of the G8 summit in Northern Ireland — Russia had been added to the grouping in 1998 and was expelled in 2014 after its annexation of Crimea — their frustration with each other was visible in an awkward photo that made headlines.

The US and its allies wanted then-Syrian President Bashar al-Assad to quit amid the civil war in that country, but Russia was backing him.

“With respect to Syria, we do have differing perspectives on the problem, but we share an interest in reducing the violence; securing chemical weapons and ensuring that they’re neither used nor are they subject to proliferation,” Obama said.

FILE - In this Nov. 20, 2016 file photo, President Barack Obama talks with Russia's President Vladimir Putin at the opening session of the Asia-Pacific Economic Cooperation (APEC) in Lima, Peru. When U.S. and Russian presidents meet, the rest of the world stops to watch. For decades, summits between leaders of the world powers have been heavily anticipated affairs in which every word, handshake and facial expression is scrutinized. (AP Photo/Pablo Martinez Monsivais, File)
Obama talks with Putin at the opening session of the Asia-Pacific Economic Cooperation (APEC) forum in Lima, Peru, on November 20, 2016 [Pablo Martinez Monsivais/AP Photo]

November 2016: Putin-Obama

By the time Obama and Putin met for the ninth and final time at the APEC Summit in Peru, there was no pretence of bonhomie.

Russia had accused the US of engineering a coup against its ally and former Ukrainian President Viktor Yanukovych in 2014. The US and its allies had imposed sanctions against Russia over its annexation of Crimea.

Putin and Obama spoke for barely four minutes on the sidelines of the summit, with the US president asking his Russian counterpart to stick to his commitments under the Minsk agreements that were meant to bring peace to Ukraine.

FILE - Russian President Vladimir Putin, right, and U.S. President Donald Trump give a joint news conference at the Presidential Palace in Helsinki, Finland, July 16, 2018. (AP Photo/Pablo Martinez Monsivais, File)
Putin, right, and Trump give a joint news conference at the Presidential Palace in Helsinki, Finland, on July 16, 2018 [Pablo Martinez Monsivais/AP Photo]

July 2018: Putin-Trump

A year and a half into his first presidency, Trump’s victory in the 2016 US presidential election was still clouded by accusations that Russia had interfered in the election on his behalf when he met Putin in Helsinki.

The two met alone, with only interpreters. In a media interaction after that, Putin tried to recast the relationship in optimistic hues. “The Cold War is a thing of past,” he said, before listing a series of modern challenges facing the world — from an environmental crisis to terrorism. “We can only cope with these challenges if we join the ranks and work together. Hopefully, we will reach this understanding with our American partners.”

But it was Trump who made headlines. After he acknowledged that he had discussed the allegations of election interference with Putin, Trump was asked whether he believed US intelligence agencies that had concluded that Moscow had intervened in the vote.

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“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.”

Trump met Putin six times in all in his first term.

FILE - Russian President Vladimir Putin, left, and U.S President Joe Biden shake hands in Geneva, Switzerland, on June 16, 2021. (AP Photo/Alexander Zemlianichenko, Pool, File)
Putin, left, and Joe Biden shake hands in Geneva, Switzerland, on June 16, 2021 [Alexander Zemlianichenko/AP Photo]

June 2021: Putin-Biden

US President Joe Biden flew to Geneva for his only face-to-face meeting with Putin.

After years of steady deterioration, relations had reached their nadir after Biden had described Putin as a killer in March, prompting Russia to withdraw its ambassador from Washington. The US had followed.

The Geneva meeting helped reset ties – a bit. Both countries agreed to reappoint ambassadors.

But Biden was also blunt with Putin about US concerns over Russian election interference and cyberattacks, and said he had, in effect, threatened Moscow that Washington could launch tit-for-tat cyberstrikes.

Russia by then was building up its troop presence along the border with Ukraine, a key source of stress in ties with the US that came up during the Putin-Biden meeting.

Eight months later, Russia would launch a fully fledged invasion of Ukraine, marking the start of Europe’s largest war since World War II — a war Trump says he wants to end through the summit in Alaska on August 15.

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