Secretary of State Rex Tillerson and Russian Foreign Minister Sergey Lavrovbetween President Trump and President Vladimir Putin, along with translators for each side. Tillerson has the most experience dealing with Putin of any member of the Trump administration. That may have helped the president navigate the meeting.
The meeting between the two had been scheduled for 35 minutes. Instead, it went on for over two hours.
At times, candidate Trump appeared taken by Putin's flattery, reports CBS News correspondent Major Garrett.
"Well, I have no relationship with him other than he called me a genius," Mr. Trump said last February in South Carolina.
"Maybe we'll have a good relationship. Maybe we'll have a horrible relationship," Mr. Trump said last October in Nevada.
As president, he must now keep his guard up.
"Putin, as a trained KGB officer… he is never caught off guard and he's never short of words," said Angela Stent, who has written extensively on Putin's relationship with American presidents and has met with him a dozen times.
"He has spent most of his adult life understanding the strengths and weaknesses of his partners and opponents and how to maximize those for his own benefit," Stent said.
Putin has charmed other American presidents, most memorably George W. Bush.
"I found him to be very straightforward and trustworthy," Mr. Bush said in 2001, adding, "I was able to get a sense of his soul."
Mr. Bush thought Putin was a true ally – especially after 9/11. He hosted Putin on his Texas ranch and on a fishing trip in Maine. Putin shattered that optimism with his 2008 invasion of neighboring Georgia, the first sign of Putin's nationalist and expansionist foreign policy.
Relations with President Obama further soured when, housed renegade national security leaker and Bashar al-Assad. Their body language at the 2013 G8 Summit in Ireland illustrated the rift, something Mr. Obama later described.
"He's got that kind of slouch, looking like the bored kid in the back of the classroom," Mr. Obama said in 2013.
Stent said Putin was insulted and wants to regain prestige with Mr. Trump.
"He needs to come out of this looking stronger and looking as if the relationship he had with President Obama, that that's over, and that President Trump is going to respect him," Stent said.
Putin and his team always look for the advantage. That means there are risks for the new American president.
"One of the dangers is that you could get President Trump to agree to something which he might then have to roll back," Stent said.
Mr. Trump has maintained all Obama-era sanctions imposed for election meddling. In February, the president said relations with Russia were too toxic for progress.
"Putin probably assumes that he can't make a deal with me anymore because politically it would be unpopular for a politician to make a deal," Mr. Trump said in February.
Putin has a history of intimidation in private meetings with world leaders. The Russian president brought along a large black labrador to a meeting with German Chancellor Angela Merkel after he found out she was afraid of dogs.
White House aides have kept Mr. Trump's preparations for this meeting simple and straight forward, reminding him to seek short-term U.S. objectives without seeking any big breakthroughs.