And is there time? The US Secretary of State, Rex Tillerson, said Trump had taken the decision to hold talks after the US was surprised at how "forward-leaning" Kim was in his conversations with a visiting South Korean delegation. First and foremost, the president should extract a promise from Kim in writing to not only freeze nuclear weapons development but to fully denuclearize. Later they traded barbs over who had a bigger nuclear button. But why should the presence of two humans in a room have such high stakes? South Korea said the president agreed to meet Kim by May, but Sanders said Friday that no time and place had been set - a refrain Trump repeated in a Friday night tweet.
President Donald Trump said Saturday he believes North Korea will abide by its pledge to suspend missile tests while he prepares for a summit by May with the North's leader, Kim Jong Un. Beyond that, little is yet known about potential objectives and concessions on either side.
Former US ambassador to the United Nations Bill Richardson has negotiated with numerous world's pariah leaders, from Saddam Hussein to Myanmar's military dictators to former North Korean leader Kim Jong Il.
Trump's willingness to take that dramatic step is a reflection of his showboat style, throwing out the diplomatic playbook and putting himself in the spotlight, in addition to what aides say is his desire to resolve the North Korea crisis before it spins out of control.
The willingness of North Korea to use chemical and biological weapons, requiring USA troops to use cumbersome protective gear, raises the risks, Fazal said. Non-nuclear states, including North Korea, signed on the dotted line.
So as President Trump contemplates a direct encounter with Kim Jong-un, he and his administration should reflect carefully and ask whether the "deal" they seek is really within reach.
"If they had a proper apparatus to deal with East Asia, it might be different". On the whole, experts in the USA and Japan find it hard to believe that Pyongyang will simply hand over its nukes.
It's likely that North Korea will also push for summits with China, Russia and Japan later in the year to further break out of its isolation, Cheong said.
A cryptic report by South Korean news agency Yonhap said the South's envoys also delivered a "special message" to Trump from Kim during their U.S. trip, but did not elaborate on what was said.
Earlier in the day, White House spokeswoman Sarah Sanders said at a briefing that Trump will meet with Kim after seeing "concrete steps" taken by Pyongyang. Mr Trump should have waited for the results of exploratory negotiations before rushing in. The current administration appears to lack all three.
US Vice-President Mike Pence has pledged to maintain pressure on North Korea, and Mr Trump spoke with Chinese president Xi Jinping on Friday to agree to maintain sanctions for the time being.
A decade after the fall of the Soviet Union, President George W. Bush famously looked into Russian President Vladimir Putin's eyes.
"His style has already produced a breakthrough", said Mr Hadley. A clear understanding of its meaning will show that North Korea's vision of "denuclearization" bears no resemblance to the American understanding of that term.
As Trump's administration ramped up its "maximum pressure campaign" on North Korea over the past year, Tillerson was one of the more enthusiastic advocates within the Cabinet for trying to talk to the North Koreans, even as other officials warned Trump of the risks of rewarding Kim too soon. "But whether it leads to a real agreement I think is very unclear at this point".
The speed of the decision leaves significant details up in the air.