Why Putin could be smiling soon
GEORGE W. Bush once said he could see into Vladimir Putin's soul, while Barack Obama found the Russian President "shrewd and unsentimental" - so how will Donald Trump view a man many fear will use him to wreck havoc on his Western rivals?
The two leaders meet tomorrow in the Finland capital of Helsinki and there is speculation among everyone from Mr Trump's domestic opponents to his European counterparts about how he will approach Mr Putin.
Given the diplomatic havoc the US President has created in recent days - first at a fiery NATO meeting in Brussels and then in London with Theresa May - many fear Mr Putin will try and widen the divisions further.
Mr Putin will be keen to see the rift between the US and Europe escalate and will be boosted by Mr Trump's comments about being open to at least discussing the presence of US troops in former Soviet republics.
The Times reported Mr Putin determined he should meet alone with Mr Trump after watching the Singapore summit with North Korea's Kim Jong-un, who secured a cancellation of US-South Korea military exercises to the surprise of US national security figures and allies.
Some fear Mr Trump will announce a withdrawal of US troops in eastern Syria - he has spoken several times about getting America "out of Syria".
He may also pursue a public statement about how people in Crimea supported Russia's annexation, even if Mr Trump refuses to formally recognise it, and will try and see some sanctions imposed on his country lifted.
When pressed about if he would consider cancelling military drills in the Baltic States, he last week told reporters: "Perhaps we'll talk about that", adding there was a clear benefit to doing it "but also a benefit not to do it".
If his own public statements are any guide, Mr Trump isn't sure how the meeting will go either. He said on Friday he wasn't sure what would come from saying something productive could arise "or maybe not".
The meeting will last four hours and initially will just be the two leaders, with no aides. Later they will be joined by US national security adviser Mike Pompeo, Mike Pompeo, the secretary of state, and Jon Huntsman, the US ambassador to Russia.
It will be held at Helsinki's Presidential Palace and will run alongside a working lunch between he two leaders. A media conference will be held at the conclusion, but it is not yet clear if Mr Putin will join it.
Helsinki was chosen as a venue partly due to its geography, but also because it is considered neutral territory. It has a long history of hosting US-Russian talks with US President George H.W. Bush and Soviet President Mikhail Gorbachev holding talks at the presidential palace in 1990.
According to the Associated Press, Mr Trump originally expressed concern Helsinki was not glamorous enough and favoured hosting Mr Putin at the White House, but was persuaded it would be effective.
For his part, the US President is hopeful of recreating the impact of his summit with Kim in Singapore - and in doing so getting Mr Putin to concede things Mr Obama could never achieve.
"I could say: 'Would you do me a favour? Would you get out of Syria,"' Mr Trump said in an interview with Fox News last month where he appeared to joke about it. "'Would you do me a favour? Would you get out of Ukraine?"'
Many in Washington DC believe the meeting will achieve nothing except provide a global platform for Mr Trump and legitimacy for Mr Putin, the day after his country hosts the Football World Cup final.
Mr Putin may find Mr Trump more sympathetic than his most recent predecessor, whose former colleagues have slammed Mr Trump for the way he deals with foreign leaders.
John McCain, the chairman of the Senate armed services committee, said Mr Trump spoke in a way about allies that should be left for "adversaries", while President Obama's national security adviser Susan Rice said the meeting could be a "recipe for disaster" because of Mr Trump's "refusal to prepare for critical meetings".
- additional reporting: AP