Rodman has no official role in the diplomatic efforts between his country and North Korea, but he appears to be invested in promoting positive ties between Washington and Pyongyang.
Secretary of State Mike Pompeo said Monday the goal remains the complete, verifiable, irreversible denuclearization of the Korean Peninsula, a policy laid out under the George W. Bush administration and continued through the Obama administration to this point.
As for Singapore, the White House said Trump was leaving early because negotiations had moved "more quickly than expected, " but gave no details about any possible progress in preliminary talks.
For Trump, cutting a deal to end the North Korean nuclear threat with his approach to Kim, in defiance of the US security establishment's long-held ways of dealing with the North, would be a success unmatched by any predecessors.
As for where Kim will spend the night, he's opted for the St. Regis Singapore, where it is believed he has checked into the hotel's $11,500-a-night Presidential Suite.
It's where former Chinese President Hu Jin Tao stayed during the 2009 APEC Summit (and don't tell Trump, but Hillary Clinton stayed there in 2011, too).
The unraveling of the Canada summit meeting increases the North Korean leader's incentive to "up his asks and limit his compromises and for Trump to do the opposite", Richard Haass, the president of the Council on Foreign Relations, said on Twitter, adding, "Hardly the ideal context".
Still, the sense of anticipation was great in Singapore, with people lining spotless streets holding cellphones high as Trump headed to meet Lee.
Probably. In fact, Trump has been doing quite a bit of this lately.
Alluding to the North's concerns that giving up its nuclear weapons could surrender its primary deterrent to forced regime change, Pompeo told reporters that the USA was prepared to take action to provide North Korea with "sufficient certainty" that denuclearization "is not something that ends badly for them".
Mr Kim was sent off in a ceremony at the Pyongyang airport joined by a group of senior officials, such as Mr Kim Yong Nam, the North's nominal head of state, Mr Choe Ryong Hae, vice-chairman of the North's State Affairs Commission, and Prime Minister Pak Pong Ju.
The fighting ended on 27 July, 1953, but the war technically continues today because instead of a difficult-to-negotiate peace treaty, military officers for the USA -led United Nations, North Korea and China signed an armistice that halted the fighting. Speaking to reporters on Monday, Rodman suggested that he may have played a role in making the world pay attention to North Korea.
Here's how the day is scheduled to go: Trump and Kim will meet at 9am local time and sit down for a one-on-one discussion (with translators, but no advisers present) at 9.15.
"In light of how many flimsy agreements the United States has made in previous years, this President will ensure that no potential agreement will fail to adequately address the North Korean threat".
The summit's venue is the Capella hotel on Sentosa, a resort island off Singapore's port with luxury hotels, a Universal Studios theme park and man-made beaches.
Trump has in the past week described the meeting as the first in a process and meant for the two leaders to get to know each other.
Trump advisers cast his actions as a show of strength before the Kim meeting.
That's in part because of South Korea's diplomatic outreach to the North, which was highlighted by two summits this spring between the rivals' leaders.
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Trump plans to brief reporters following the summit's conclusion, and will leave for the USA around 8pm local time (midnight NZT). But he said that any past US president could have gotten a one-on-one meeting with the leader of North Korea .