Singapore was selected as the host site because it has significant experience in staging major global events, including a summit between Chinese President Xi Jinping and then-Taiwanese President Ying-jeou in 2015, the first such meeting in almost seven decades.
New York Times op-ed writer and two-time Pulitzer Prize victor Nicholas Kristof. Mr Xi's agenda remains hidden, and muddied by its complicated relationship with both North Korea, and the US.
President Trump has spent the past week tamping down expectations, calling it a "get acquainted meeting, plus", and saying "it's a process".
His two friendship medals from the rogue state are among his most prized possessions. Will Kim Jong Un reciprocate, and if so, how?
Yet many close observers doubt the once hostile leader's appetite for peace. The Lowy Institute's worldwide security director Euan Graham says Mr Kim has relied on the classic North Korean playbook, swinging predictably from provocation to engagement.
"I think we were played".
"But it's an bad lot better than firing missiles at each other".
Trump frequently has boasted of his negotiating prowess as a real estate developer, and his ability to read people, even though his businesses have declared multiple bankruptcies.
Over the years, I've had many hours of discussions with North Korean officials about human rights.
She said if the outcome was denuclearisation in North Korea, "we all need to celebrate that". He said he thinks "it's going to work out very well".
"Within the first minute, Ill know", Trump said during a news conference in Quebec as he prepared to depart the Group of 7 summit en route to Singapore, where he is scheduled to meet Kim on Tuesday.
Ronaldo Makes An ‘Irreversible’ Decision To Leave Real Madrid
He sparked a huge reaction with his post-match interview, which has stuck with many supporters in spite of a later apology. Numerous factors seem to have contributed but doubts revolve around his pay compared to Lionel Messi and Neymar .
Poll numbers that showed most Americans - on both sides of the aisle - approve of his handling of North Korea. "I think it would be well received and I think [Kim] would look at it very favorably".
He added that Obama left Trump with "unfettered worldwide disaster after disaster".
"I think within the first minute I'll know" if North Korea is serious about a deal, said the president, who then touted his dealmaking abilities.
North Korea has a reputation for pocketing rather than reciprocating unilateral concessions.
What is achievable is really anyone's calculated guess.
The report didn't reveal the exact date of Kim's visit amid reports that his arrival in Singapore is imminent ahead of the June 12 summit.
To achieve this long-held desire he has dramatically shifted in character from isolated angry strongman to global statesman.
But Trump also hedged his bets, claiming that the results he demands - a complete denuclearization of the peninsula - could take time. Glor will also lead Special Reports for coverage on the summit, and contribute to CBSN, CBS News' 24/7 streaming news service.
Trump's meeting with Abe comes ahead of what promises to be a tense Group of Seven summit in Canada, clouded by the USA leader's aggressive trade policies. "That's what I do", he added. We've had hawkish policies, we've had sanctions and so on, they don't work. We have values at stake as well as interests. "That's why I feel positive because it makes so much sense".
"It's not like the Trump-Kim summit will solve everything", he added. And when they blow up at a presidential level, Kristof points out, it's hard to put the pieces back together. He called Kim an "unknown personality". China - North Korea's only ally - has long pushed for dialogue between Washington and Pyongyang.
"I think President Trump signed onto this thinking that he was going to ride in on a white horse to Singapore, accept a bunch of nuclear warheads, and problem solved", Kristof says.
Matt Kulesza with two North Korean students.
Watch Susan Ormiston's interview with Nicholas Kristof about the U.S. He believes North Korea is unfairly portrayed in the West.
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