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.

June 2000: Putin-Clinton

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