The president views the meeting as the first of perhaps several meetings with Kim, and the tangible "deliverables" are hard to forecast.
Whether such a deal can be done, Trump declared on Saturday, is something he will know nearly from the moment they meet. "It is a historic negotiation, and there is no way this president is not going to stand strong", Kudlowsaid.
In a final round of pre-summit preparation, top negotiators from the two sides met Monday at the Ritz Carlton Hotel.
"I bet the North will not abandon nuclear weapons", he said, adding that the USA and its allies should use both "carrots and sticks" to force the North to do so.
The clearest benchmarks about what the U.S.is seeking from the summit, however, have come from Pompeo rather than Trump. Ambassador Kim arrived with one advisor, past a scrum of television cameras.
On the U.S. side, joining Trump was a delegation of high-level officials, including Secretary of State Mike Pompeo and National Security Adviser John Bolton.
The Olympics-inspired diplomacy led to more talks with the South, during which the North extended an invitation for Trump to meet with Kim. But it's unclear what that security guarantee would entail. But any request for the USA to withdraw its 28,000 troops from South Korean bases would likely be rejected.
"Wide-ranging and profound views on the issue of establishing new DPRK-U.S. relations, the issue of building a permanent and durable peace-keeping mechanism on the Korean Peninsula, the issue of realizing the denuclearization of the Korean peninsula and other issues of mutual concern, as required by the changed era, will be exchanged at the DPRK-U.S. summit talks", a dispatch by the North's official Korean Central News Agency (KCNA) said.
"Even after the two leaders open the dialogue, we will need a long process that may take one year, two years or even longer to completely resolve the issues".
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That may be even more important to Trump in the wake of the disastrous G-7 summit.
But the spectacle was absorbing.
Earlier on Sunday evening, Trump arrived at Singapore's Paya Lebar Air Base and is now staying at the Shangri-La Hotel.
Curious onlookers wait for the departure of Donald Trump's motorcade from Singapore's presidential palace. He thanked Singapore hosting the summit as if it was "their own family affair". But, death grip handshakes aside, Trump has so far been gushingly polite in his dealings with Asian leaders.
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.
Trump, who is offering to reduce economic sanctions on North Korea in exchange for denuclearisation, also seemed to warn Kim that the summit is a "one-time opportunity" that should not be wasted.
Likely to attend the summit with Trump are Pompeo, Bolton and White House chief of staff John Kelly.
North Koreans were told two weeks ago that a summit between Kim and Trump would take place, but not when or where it would happen.
Mr Kim has only publicly left his country three times since taking power after his despot father's death in late 2011 - twice traveling to China and once across his shared border with the South to the southern part of the Demilitarised Zone in recent summits with the leaders of China and South Korea respectively.