Kim has given signs that he wants to resist Beijing's influence - and the United States can help him there.
He thanked Singapore's organisation of the summit as if it was "their own family affair". The president arrived in Asia having blown up relations with USA allies - and personally with French President Emmanuel Macron and Canadian Prime Minister Justin Trudeau - over trade and Russian Federation, announcing via Twitter en route to Singapore that he'd withdraw from a joint agreement covering climate change and other issues.
But in his new diplomatic role - until March he had not left his country for more than six years - Kim has come across as polite, respectful and even charming in meetings with the Chinese and South Korean leaders. And so, the first indication of success will be that the two leaders don't rub each other the wrong way and that the meeting exceeds 60 seconds.
"Despite his young age, he seems to be shrewd", he said, adding that he believes Kim realises his crusade to develop a nuclear arsenal to ensure his regime's survival has "hit a dead end" under intensifying sanctions.
In return, Kim, said to be in his mid-thirties, called Trump "mentally deranged" and a "dotard".
Kim may also be seeing the gamble in a light never considered by his autocratic father and grandfather because of "his determination to modernize North Korea", according to Ryan Haas, an Asia expert at the John L. Thornton China Center. "There is a very wide gap between the USA and North Korean negotiating positions, and finding common ground will require a sustained diplomatic process with high-level buy-in from Pyongyang and Washington", Daniel Wertz, associate director of the National Committee on North Korea, told Newsweek.
He initially touted the potential for a grand bargain with North Korea to rid itself of a nuclear missile programme that has advanced rapidly to threaten the United States. Their meeting is expected to begin Tuesday with a one-on-one session - just Trump and Kim and their personal interpreters.
Bourdain's death means loss of a voice for immigrant workers
Chef Wan said he broke into laughter when he saw Bourdain's description of him, as the American was initially very reserved. "Any stranger who shows an honest curiosity about what the locals think is the best food is going to be welcomed".
But last month, Trump abruptly cancelled the Singapore summit, citing the "tremendous anger and open hostility" by Pyongyang.
Before flying home, Trump planned to speak to reporters in Singapore after concluding the summit, the White House said. US President Donald Trump is set to arrive in the city-state later on Sunday. "And he has that opportunity, and he won't have that opportunity again", Trump said.
People crowded around poster stands at train stations around the capital, Pyongyang, to read the news, and gathered at noon on Monday in front of the city's main train station to watch a large screen display of images of Kim disembarking from the special Air China flight that took him to Singapore.
"I am on my way to Singapore where we have a chance to achieve a truly wonderful result for North Korea and the World", Trump wrote in a pair of tweets.
"North Korea's increased dialogue with other countries is a positive step, but before the world gets too excited they should remember that Kim Jong Un still presides over perhaps the most repressive system in the world", he said. Create peace and great prosperity for his land. "And if I think it won't happen, I'm not going to waste my time".
Donald Trump has sat down for lunch with his Singapore's Prime Minister Lee Hsien Loong.
The commemorative coin issued ahead of the US-North Korea Summit.
It has been used before for high-profile diplomatic occasions.