President Donald Trump gets a second chance to make a first impression at the G20 Summit in Germany this week, where he'll have to negotiate a minefield of "uncomfortable conversations" with the gathered leaders.
Trump will face discussions on counter-terrorism, the civil war in Syria, trade, and the climate among other topics with his European counterparts.
And in his meeting with Russia's President Vladimir Putin, Trump will have to balance a working relationship on issues like Syria and fighting ISIS while showing European leaders the United States will be a check on Moscow's aggression.
German Chancellor Angela Merkel – who declared in May the United States couldn't be relied upon as an ally – is expected to be ready for tough talks on trade and climate change, with the Trump's decision to pull out of the Paris accord a likely flashpoint.
"The G20 agenda is set for some uncomfortable conversations," Charles Kupchan, a Council on Foreign Relations senior fellow, told NBC News. "It will be dominated by climate change, by free trade, by immigration, and these are issues where Trump is — more or less — alone."
According to NBC, the leaders — and issues — to watch include the host of the summit, Merkel, with German Marshall Fund's Sudha David-Wilp telling the outlet, "All eyes are on" the German leader.
"The top line will be: Is Trump — as he was during his first trip to Europe — the odd man out," Kupchan told NBC News.
And after months of investigations into alleged Russian meddling in the 2016 election, Trump on Friday has a face-to-face meeting with Putin.
"I expect an Olympian level of macho posturing between these two leaders, who both understand the importance of symbolism and the perception of being tough," Derek Cholett, former assistant secretary of defense for international security affairs under President Barack Obama, told NBC News.
The question, he said, will be "what Putin asks for and what he offers in return."
NBC News noted that Trump’s mantra of "jobs, jobs, jobs" and his vow to get the best deal will be on display at the summit.
The goal, said Gary Cohn, director of the National Economic Council, "is to work with our partners to jumpstart the world economy” which has been "too weak for far too long."
Meanwhile, Germany is bracing for the possibility of a "contentious time" with the United States on trade, David-Wilp told NBC News.
And Trump's climate decisions also will be a bone of contention for Merkel, though advisers have said Trump remains open to doing some kind of agreement on climate, NBC News reported.
Kupchan predicted Merkel may be "more inclined to look to Beijing than Washington for help" on the issue, NBC News reported.
The Associated Press contributed to this report.
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