The standard thinking goes that he needs quick help to stabilize and then rebuild an economy that has suffered amid a decades-long pursuit of nuclear bombs, and that the North Koreans see a unique chance to win concessions, legitimacy and protection from a meeting with a highly unconventional US president who's willing to consider options past American leaders would not.
But Trump said: "We could absolutely sign an agreement and we're looking at it", adding: "Sounds a little bit unusual, but that's probably the easy part".
Observers in the region warn that ultimatums over denuclearization could make military confrontation between the USA and North Korea even more likely, a situation Zhao Hai from China's Academy of Social Sciences described as a "down-spiral of security" that could turn into a nuclear "nightmare".
Hours earlier, Kim had arrived in a jet and was received by Balakrishnan before heading to St Regis Hotel. The North Korean leadership, including Vice Minister of Foreign Affairs Choe Son Hui has also taunted Washington, calling Vice President Mike Pence a "political dummy".
Trump, who is staying in a separate hotel, the Shangri-La, is due to meet Lee on Monday.
"We've got a very interesting meeting. tomorrow, and I just think it's going to work out very nicely", Trump said.
Singapore has spent $S20 million hosting the summit, half of that on security costs, with Lee saying it was "in our profound interest" to contribute to such an worldwide endeavour.
"Thanks PM Lee for spending $20 million of taxpayers money, which can. help a lot of needy families in Singapore to survive", posted one Facebook user.
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The cost of hosting around 2000 worldwide media was put at $S5 million, but Lee said the publicity and boost for Singapore's global standing was worth it. The newspaper said the vehicles weren't from a local authorized dealer, which suggests the cars were brought in specifically for the summit and may be used by Kim.
The talks would also involve "building a permanent and durable peacekeeping mechanism on the Korean peninsula and "the issue of realising the denuclearisation of the Korean peninsula", the agency said".
"We will not be surprised by any scenario", said the official.
Trump spoke to a group of White House reporters in Charlevoix in the Canadian province of Quebec after cutting short his appearance at the G-7 leaders' gathering. "And then we'll find out later that, obviously, we didn't get there in terms of, you know, our goal, which is complete, verifiable, irreversible dismantlement of their program".
It "would instead lay out practical steps with requisite commitments from North Korea that demonstrate that it understands, accepts and is committed to achieving denuclearisation as the USA defines it", said Enos, who is also in Singapore to watch the proceedings.
Later, they would be joined by their respective negotiating teams for discussions that could last another hour.
The statement added that the island will remain accessible to all through "multiple modes of access" from 10 to 14 June, with the exception of the compound within Capella Singapore, where the summit will take place on 12 June. The United States stations 28,500 troops in South Korea, a legacy of the Korean War. Kim also released a statement in September that said he will "surely and definitely tame the mentally deranged USA dotard with fire".
But he has since lowered expectations, backing away from an original demand for North Korea's swift denuclearization.