Moscow: During more than 18 years in power in Russia, President Vladimir Putin has encountered four US Presidents but not built lasting good relations with any.
Here is a summary of relations between Putin and US leaders, ahead of his Helsinki summit on Monday with President Donald Trump:
Clinton and Kosovo
Putin became prime minister in 1999 as warm ties between president Boris Yeltsin and US leader Bill Clinton chilled over the Kosovo conflict.
Russia was outraged by NATO-led airstrikes against its Serbian allies in response to a massacre in Kosovo. Putin took office as premier months afterwards.
Bush sees Putin's 'soul'
Relations thawed from 2001 under President George W. Bush and Putin, now Russian president. Putin offered Russia's support in fighting terrorism after the September 11, 2001 attacks.
In June 2001, Bush told a news conference alongside Putin: "I looked the man in the eye. I found him to be very straightforward and trustworthy... I was able to get a sense of his soul."
The countries fell out again over US plans for a missile shield in eastern Europe, the US invasion of Iraq and Washington's backing for the pro-Western "Orange revolution" in Ukraine.
Obama 'reset'
US President Barack Obama vowed to "reset" relations with Russia, under Putin as prime minister and then president again from 2012.
Initial advances included the signing of a nuclear disarmament treaty in 2010. But that detente did not last either.
The countries exchanged sanctions in 2012 over the death of a Russian anti-corruption lawyer.
Russia also fell out with Western powers over the downfall of Libyan leader Moamer Kadhafi.
The West backed an uprising against the pro-Russian leadership in Ukraine. Moscow and the West also backed opposite sides in the Syrian civil war.
Trump tightrope
Donald Trump vowed to mend US relations with Moscow during his presidential election campaign.
Since becoming president in 2017, he has been beset by allegations of Russian meddling in the US election and collusion between the Kremlin and his campaign team.
The two countries have expelled each others' diplomats and exchanged fresh sanctions.
Trump's promise to restore ties with Moscow will be put to the test at Monday's summit in Helsinki.
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