North Korean leaders, who have been subject to some of the world's toughest ever sanctions, have long wanted to meet with the USA president, in part because of the worldwide legitimacy such a summit would provide.
What was initially portrayed by the White House as a summit meant to completely rid the North of its nuclear weapons is now being cast as a chance to "start a dialogue" and for Trump the dealmaker to look into the eyes and take the measure of his nuclear-armed antagonist.
Kim's massive security team covered him from all sides, making him barely visible to reporters who were snapping pictures of the "procession".
In the weeks leading up to the summit in Singapore, Trump praised Kim as "very honorable" and "very open", a stark contrast from the "Little Rocket Man" moniker Trump had previously bestowed on the North Korean leader.
Nobody is pretending North Korea can ape Singapore but the message to Kim of the hermit kingdom is clear - come in from the cold on the steaming hot humid south Asian island of Singapore. Trump had earlier tweeted about "excitement in the air!"
"The ultimate objective we seek with diplomacy with North Korea has not changed".
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.
There was no word on how Trump was spending the night before the summit.
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Kim held a meeting with Singapore Prime Minister Lee Hsien Loong ahead of the planned summit.
Few people expect Kim to commit to what some Trump administration officials call "CVID:" Complete, verifiable, and irreversible dismantlement of nuclear weapons programs - certainly not at this meeting, and perhaps not ever.
The world now needs to wait for Trump and Kim to finally meet.
Kim's Diplomatic Win 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.
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. He went out of his way to be cordial during two summits with South Korean President Moon Jae-in in April and May.
Citizens are traditionally told - pretty much from birth - that the United States and former colonial power Japan are the great enemies of the people of the Korean peninsula. And he won't have that opportunity again.