Their meeting at a luxury hotel in Singapore, scheduled for 9 a.m. local time -- 9 p.m. EDT Monday -- will mark the first face-to-face encounter between a U.S. president and a leader of North Korea. Its outcome could prove pivotal in determining whether the two nations pursue a lasting peace or a fresh military conflict.
The summit represents a major gamble for each leader, a high-wire act that carries the elevated potential for risk and reward that Trump has become increasingly comfortable with. The meeting will be monitored and dissected around the globe for a sense of whether one of the world's greatest national security threats -- Kim's nuclear arsenal -- can be solved.
"The way the summit goes in Singapore could set the stage for the next period of Northeast Asian regional security," said Eric Altbach, vice president of the Albright Stonebridge Group in Washington, who also represented the National Security Council in sanctions discussions with North Korea during the Bush administration.
"We could be on a course for a more collaborative approach and lower tensions, albeit in a very challenging path forward on the North Korean nuclear issues. Or we could have a failed summit that really takes us in the other direction."
On the summit's eve, Secretary of State Mike Pompeo drew a firm line, saying the U.S. plans to keep sanctions in place until North Korea eliminates its nuclear weapons capability. Complete, verifiable, irreversible denuclearization, he told reporters, "is the only outcome that the United States will accept."
Yet the top U.S. diplomat added Trump is ready to offer "unique" guarantees to ease the regime's concerns about giving up a nuclear arsenal that provides a deterrent against foreign adversaries while also serving as a key point of national pride.
"We're prepared to take actions that will provide them sufficient certainty that they can be comfortable that denuclearization isn't something that ends badly for them," he said.
Trump and Kim will first pose for a handshake, followed by a private one-on-one meeting, the White House said Monday. They'll be joined later by their staffs for an expanded meeting and a working lunch. Trump will hold a press conference and leave Singapore later Tuesday, the White House said, noting that negotiations "have moved more quickly than expected." Trump had previously said the talks might extend beyond the first day.
Trump, a former real-estate developer, has approached his meeting with Kim like a business negotiation -- with flattery, flashy promises and flexible terms juxtaposed with constant threats to walk away from the table. He said last week that he expects to know "within the first minute" of their meeting if Kim is serious about giving up his weapons.
Kim has been more cryptic and calculating, with his regime vacillating between welcoming talks with the U.S., ignoring American overtures, and sharply attacking some of Trump's top officials with insults and threats, said Patrick Cronin, director of the Center for a New America Security's Asia-Pacific security program.
At issue is whether Kim would be willing to abandon a nuclear weapons program that has advanced rapidly in recent years, posing an increasing threat to the U.S. and its allies.
Trump has said that North Korea must decide to "denuke" or there will be no deal and economic pressure on the regime would only intensify. He credits his administration's "maximum pressure" campaign with getting Kim to the table.
Pompeo, who has traveled twice to Pyongyang to meet with Kim, told reporters Monday that North Korea has conveyed a willingness to denuclearize.
But Pompeo has refused to answer reporters' questions about whether the two governments had reached agreement on how to define denuclearization, and how it might play out.
North Korea has previously promised to denuclearize, only to continue its nuclear program after receiving concessions from the U.S., said Michael J. Green, senior vice president for Asia and Japan Chair at the Center for Strategic and International Studies.
Few experts believe that Kim, who has conducted several missile tests in recent years, is willing to dismantle his entire nuclear program.
The process could turn on what Trump is willing to offer Kim for ending his pursuit of nuclear weapons and submitting to intrusive inspections.
The president has said that he would be willing to guarantee the safety of Kim's regime -- though it's not clear how he would back that up. He has also said that North Korea would benefit economically after sanctions are lifted.
Just meeting with Trump will be a diplomatic accomplishment for Kim, who has emerged from isolation in recent months and rapidly increased his outreach to other world leaders. By sitting down with an American president -- a longtime goal of North Korea's government -- Kim's regime is advancing its effort to establish its "reputation, respect, and credibility as a nuclear weapon state," Green said.
Top members of Trump's administration have said that the North Koreans wouldn't receive any benefits before taking steps to denuclearize -- wary of falling into the same predicament that doomed previous agreements with the rogue regime.
But North Korea now deems itself "a nuclear state," and insists the U.S. must end its "nuclear threats and blackmail" as a precondition for denuclearization, according to a statement last month from First Vice Minister of Foreign Affairs Kim Kye Gwan.
Pompeo's firm line on sanctions relief suggests that the U.S. is looking for a short transition toward denuclearization, according to Zhang Baohui, director of the Centre for Asian Pacific Studies at Lingnan University in Hong Kong. That would avoid the prospect of Kim winning sanctions relief for gradual progress while remaining a nuclear power.
"The idea is to force North Korea to do a quick and complete denuclearization and not to drag it out, which will make the United States look like a fool," Zhang said "The problem here is: Will Kim accept this?"
Trump suggested last week the two leaders may sign a peace agreement to formally end the Korean War 65 years after the armistice that ceased military hostilities.
"We could sign an agreement. As you know, that would be a first step,'' Trump told reporters June 7 during a joint news conference with Japanese Prime Minister Shinzo Abe at the White House. "It's what happens after the agreement that really is the big point.''
Less than a week before the summit, Trump dismissed questions about his readiness, saying, "I don't think I have to prepare very much. It's about attitude, it's about willingness to get things done.''
Kim, on the other hand, has shown he is prepared for his moment on the world stage, and could end up outfoxing Trump, said Victor Cha, a senior adviser and Korea Chair at the Center for Strategic and International Studies in Washington.
"North Korea has been preparing for this meeting for this meeting for 45 years,'' he said. "So you can't go in unprepared because the North Koreans will open lots of trap doors for you.''