Putin vs. POTUS: Two Decades of Tense Relations and Diplomatic Standoffs

Since assuming office in 1999, Russian President Vladimir Putin has been a pivotal figure in global politics, engaging with U.S. Presidents from Bill Clinton to Joe Biden, each relationship characterized by its unique set of challenges and diplomatic maneuvers.

Spanning over two decades, Putin's political tenure has intersected with the administrations of five U.S. leaders, each bringing their own policies and perspectives to the often fraught U.S.-Russia relationship.

As Putin is inaugurated for an unprecedented fifth six-year term, Newsweek takes a look at those relationships, and the ongoing chess match between the Kremlin and White House that has influenced major geopolitical issues from cybersecurity to wars in Ukraine and the Middle East.

Bill Clinton: The Initial Encounter (1999-2000)

The beginning of Putin's tenure overlapped with the final months of Bill Clinton's presidency. Despite a warm relationship with Putin's predecessor, Boris Yeltsin, Clinton has recounted that he found Putin personally cold, but competent.

Clinton once said he hung up after congratulating Putin on becoming acting Russian president in 1999 "thinking he was tough enough to hold Russia together."

As NATO expanded eastward in the late 1990s and conflict erupted in Kosovo, tensions between the two superpowers ratcheted up. Clinton criticized Russia's campaign in Chechnya, prompting sharp responses from Putin.

More recently, due to Russia's war in Ukraine, Clinton rejected the notion that Putin's invasion was a response to NATO's expansion, which began during his presidency. He told CNN in 2022: "I think we did the right thing at the right time. And if we hadn't done it, this crisis might have occurred even sooner."

George W. Bush: From Soul Gazing to Tension (2001-2008)

George W. Bush entered office aiming to stabilize relations with Russia. His initial encounters with the Russian leader were warm, illustrated by Bush's famous claim to have looked into Putin's eyes and seen his "soul" during a press conference on June 16, 2001, in Slovenia. However, the relationship deteriorated over disagreements over the Iraq War, U.S. missile defense plans in Eastern Europe, and Russia's internal policies, which Bush saw as increasingly authoritarian.

While there were moments of camaraderie, Putin had his own criticisms of the Bush presidency. As the Iraq war deterioriated into a quagmire for the U.S., Putin said he would not be lectured on democracy from the American president. "We would not want to have a democracy like in Iraq," he told reporters during a joint press conference with Bush.

Bush's vice president, Dick Cheney, also remained unmoved, saying when he saw Putin, "I think KGB, KGB, KGB," referring to the Soviet secret service to which the Russian president once belonged.

When Russia invaded Georgia in the waning days of Bush's second term in 2008, Bush confronted Putin directly at the Beijing Olympics, he wrote in his memoirs. Bush wrote that warned Putin that the Georgian president was hot-blooded.

"I'm hot-blooded too," Putin replied. "No, Vladimir," Bush retorted. "You're cold-blooded."

Barack Obama: The Chill Deepens (2009-2016)

Barack Obama, who also came into office with plans to "reset" relations with Russia, found himself increasingly at odds with Putin almost from day one of his presidency. Obama's working relationship with Putin was mostly marked by sanctions and diplomatic standoffs. Disagreements over Syria, Ukraine and allegations of election interference led to a new low in bilateral relations.

Diplomatic relations between the Kremlin and White House all but collapsed with Russia's surprise annexation of Crimea on March 18, 2014, which preceded the full invasion of Ukraine by eight years and led to a renewal of the Cold War-esque tension that simmers today.

Obama once described Putin as a "tough, street-smart, unsentimental" character, also saying that Putin reminded him of the political barons he encountered during his early career in Chicago.

For his part, Putin never made his distaste for Obama much of a secret, once saying: "President Obama hasn't been elected by the American people to be pleasant to Russia..." In response to Obama's comment calling Russia a "regional power," Putin said, "It is hard to dialogue with people who confuse Austria with Australia."

Donald Trump: Controversial Camaraderie (2017-2020)

Donald Trump's presidency was marked by controversy from the beginning over alleged Russian interference in the 2016 election. But Trump and Putin appeared to have a somewhat warmer personal relationship.

The relationship was marked by public admiration. Putin, who once referred to Trump as a "colorful individual," expressed his willingness to work with him from the beginning.

Their interactions were marked by a series of high-profile meetings, including a notable summit in Helsinki where Trump appeared to side with Putin over his own intelligence agencies regarding election interference. That exchange caused uproar in the U.S., with critics accusing Trump of undermining American interests.

Putin, for his part, seemed to appreciate Trump's willingness to flout conventional diplomatic norms but remained cautious, aware of the political instability Trump's presidency brought.

The Russian president also saw an opportunity with Trump in office, using Trump's impeachments and investigations to criticize the American political system as "rotten".

Joe Biden: Back to the Cold War (2021-present)

When Joe Biden came into office, U.S.-Russia relations saw a return to a more confrontational style — inherited from the Obama administration — with Biden openly criticizing Putin and taking a firm stance on issues like human rights and Ukrainian sovereignty.

One of the defining moments early in his presidency was when Biden agreed with a description of Putin as a "killer" during a media interview, which led to a brief recall of the Russian ambassador to the U.S. for consultations — a diplomatic signal of the frayed relations between the two powers. In response, Putin said simply: "It takes one to know one." He also argued that the U.S. was a murderous state, citing historical events such as slavery and the atomic bombs dropped on Japan by the U.S. at the end of WWII.

The Biden administration, along with Western allies, has also slapped Russia and Putin personally with sanctions since the invasion of Ukraine. The last meeting between the two leaders took place in 2021 — before the war — at a summit in Geneva, Switzerland. Both leaders agreed at the time that the relationship was at a "low point."

It would only go lower from there.