Mr Trump descended from Air Force One into the steamy Singapore night, greeting officials and declaring he felt "very good" before being whisked away to his hotel via a route lined with police and photo-snapping onlookers.
The North has presented Kim's sudden diplomatic overtures to the country's neighbours and the United States as a logical next step and completion of his plan to develop a credible nuclear deterrent in response to what Pyongyang says is a policy of "nuclear blackmail" by Washington. The president has consistently predicted success, even as his definition of that has grown foggier.
As Kim departed for Singapore, North Korea's state-run Korean Central News Agency noted that the objective of the summit would be to share "wide-ranging and profound views on the issue of establishing new DPRK-U.S. relations", with "denuclearization" receiving a perfunctory mention.
Trump and Kim planned to meet one on one for most of an hour- joined only by interpreters.
Mr Pompeo said Mr Trump was "fully prepared" for the talks, and was optimistic that the outcome would be "successful".
The motorcade carrying North Korean leader Kim Jong-un, drives past on the street in Singapore on June 10, 2018.
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North Korea has long rejected unilateral nuclear disarmament, instead referring to the denuclearization of the peninsula. Most important, few believe Kim is actually willing to give up the nuclear weapons that cement his grip on power.
It was a striking about-face from less than a year ago, when Trump was threatening "fire and fury" against Kim, who in turn scorned the American president as a "mentally deranged US dotard".
Totalitarian North Korea's governing ideology of "Juche", which champions self-sufficiency, has brought little but decades of economic stagnation, widespread poverty and, at times, starvation.
Mr Trump and Mr Kim arrived in Singapore on Sunday, both staying at luxurious and heavily guarded hotels less than one kilometre, with Mr Trump at the Shangri-La Hotel and Mr Kim at the St Regis Hotel.
On May 30, Pompeo met with North Korean spy chief Kim Yong-chol in NY; their discussion concluded two hours earlier than expected, as Kim refused to make any commitment whatsoever on denuclearization, according to the Washington Post. The president wants the complete, verifiable and irreversible dismantling of his nuclear weapons program.
As Trump was trying to build a bridge with Kim, he was smashing longtime alliances with Western allies with his abrasive performance at the G-7.
The senior official said Seoul could have chose to go ahead with a visit at "the very last minute", but reiterated the Moon administration would not rush the signing of a peace treaty.
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Asked Saturday about his goals, he said: "Well, I think the minimum would be relationship. Thank you very much". The summit will instead focus on the country's nuclear weapons arsenal.
Experts believe the North is on the brink of being able to target the entire U.S. mainland with its nuclear-armed missiles, and while there is deep scepticism that Mr Kim will quickly give up those hard-won nukes, there is also some hope that diplomacy can replace the animosity between the United States and the North.
The private first meeting will come amid concerns from USA officials, allies and North Korea experts that Trump has not sufficiently prepared for his meeting with Kim and instead plans to open the dialogue in a more freewheeling fashion by following his gut instincts rather than a predetermined strategy.
China, both Koreas and the United States would have to sign off on any legally binding treaty, so it is unlikely Kim and Trump will do more than express an intention to end the war.
Even so, the summit continues to be a sensitive topic in North Korea and it is hard - even more so than usual - to get people to express opinions about it.
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