Even before the two leaders had left their separate city centre hotels and driven the 13 minutes through blocked-off police-lined roads to the island summit venue, the U.S. president used Twitter to claim victory and hit back at his critics.
While advisers say Trump has been reviewing briefing materials, the president insists his gut instincts will matter most when he gets in the room with Kim.
"We hardly ever talk politics", Rodman said.
That decision has raised concerns about the risk of holding such a monumental meeting with barely anyone to bear witness.
China is also hoping that the summit leads to an easing of the worldwide sanctions that have been imposed on North Korea. With the eyes of the world upon them, here is a breakdown of how the day will unfold.
Greg Scarlatoiu, executive director of the USA -based Committee for Human Rights in North Korea, and Rabbi Abraham Cooper at the Simon Wiesenthal Center urged Trump to seek "the complete, verifiable, irreversible dismantlement" of North Korean political prison camps - mimicking the formulation used by the U.S.in its demand for that nation's denuclearization.
US President Donald Trump and North Korean leader Kim Jong Un begin their historic summit at 1pm NZT in Singapore, a meeting that could lead to peace between countries that have technically been at war for 68 years - or swiftly end in new recriminations.
"I just think it's going to work out very nicely", he said during a lunch with Singapore's prime minister on Monday.
The US is also concerned about the proliferation of North Korea's weapons and the infrastructure supporting its nuclear programme, and will want those issues addressed as part of any deal.
The PBS NewsHour's Nick Schifrin tells managing editor and anchor Judy Woodruff the latest from Singapore.
But some question why Kim should trust any guarantees given Trump's history of pulling out of accords - most recently the painstakingly negotiated Iran nuclear deal.
Japan officially lists 17 citizens as abduction victims and suspects North Korea's involvement in many more disappearances.
Smart negotiations with Kim could help to rein in North Korea's nuclear activities and significantly disrupt Iran's efforts to improve upon its ballistic missile capabilities.
Retired American professional basketball player Dennis Rodman speaks to the press as he arrives at Changi International airport ahead of US-North Korea summit in Singapore on June 11, 2018. The two leaders are expected to meet at 9 a.m. local time on Tuesday, or 9 p.m. Monday ET.
Dinner plans were abandoned by reporters, including this correspondent, as they raced to likely locations for the first close up look at Kim, who had remained out of sight in the St Regis on Monday. To believe Kim would agree to relinquish his nuclear arsenal-the greatest deterrent for an global campaign to depose his regime-on words alone, or consent to immediately shipping his program out of the country as National Security Advisor John Bolton suggested, were always ludicrous propositions. But Kim Jong Un chose to take a little sightseeing tour of the major spots where a lot of tourists go in Singapore with only 10, 11 hours to spare before the summit happening.
Kim's black armored limousine with two large North Korean flags was surrounded Tuesday by police vehicles, their lights flashing, and other black cars.