Trump and Kim are scheduled to hold talks starting Tuesday, and possibly extending longer, on Singapore's resort island of Sentosa.
New York Times op-ed writer and two-time Pulitzer Prize victor Nicholas Kristof.
At best, a framework will be agreed upon in which North Korea agrees to completely and verifiably denuclearise, and the rogue state actually follows through on its commitment.
Raising expectations in advance of the meeting, Trump said the outcome will rely heavily on his own instincts.
His two friendship medals from the rogue state are among his most prized possessions. It will certainly be an exciting day and I know that Kim Jong-un will work very hard to do something that has rarely been done before, create peace and great prosperity for his land.
Kristof, a two-time Pulitzer Prize-winning journalist who has covered the region for almost 30 years, is not convinced the result will be anywhere near big and bold.
"Nobody started talking about a meeting between Kim Jong Un and President Trump until we suggested it at the Olympics", Alan added, referring to their appearance at the Pyeongchang Winter Olympics in February. "It really amazed me and I thought we can learn a lot".
"And if I think it won't happen - I'm not going to waste my time".
"But it's an bad lot better than firing missiles at each other".
The summit idea seemed to appear out of nowhere back in March, when Trump announced a meeting.
Kim, the 39-year-old founder of People for Successful Corean Reunification (PSCORE), escaped North Korea when he was 19 years old.
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He said: "I have a clear objective, but I have to say - it's going to be something that will always be spur of the moment".
"I think within the first minute, I'll know", Trump said, when asked about negotiations over the United States demand for the complete surrender by Pyongyang of its nuclear weapons. (South Korea Presidential Blue House/Yonhap via AP) Kristof credits the South Korean president for deftly handling both sides. "It's the engagement, especially humanising, giving a human face to North Korea, that is our biggest protection from war".
What is achievable is really anyone's calculated guess.
The armistice was more of a ceasefire agreement, instead of a permanent peace treaty. "We're going in with a very positive spirit".
"That takes a great deal of work, a great big commitment on the part of North Korea as well, and there'll be a parallel set of security assurances that are also big and bold and different", the top USA diplomat said.
Given North Korea's systemic threat to the region and the world, reasonable minds should agree that a Trump-Kim deal is a good thing, even if it slows, but does not stop, North Korea's dark ambitions.
Such is the short-term nature of politics, and the cult of personality unique to the Trump presidency.
SINGAPORE, June 9 ― A rare direct flight from Pyongyang landed in Singapore today ahead of the expected arrival of North Korea's leader Kim Jong Un for a summit with US President Donald Trump to discuss ending the North's isolation and its nuclear programme.
"Just my touch, my feel".
"I think it would be an asset to have Russian Federation back in, it would be good for the world. I mean, if you are a diplomat, you [would be] very, very focused on this truly historic opportunity to solve a nuclear crisis a standoff", Kristof adds.