The impulsive American president, who just this weekend sowed chaos within the Western alliance, is set to face his match on the global stage as he prepares to meet Kim in Singapore on Tuesday. The official was not authorized to speak publicly about internal deliberations and insisted on anonymity.
Bringing the Korean War to a formal end 65 years after hostilities ceased will also be on the table at the first-ever summit between a North Korean leader and a sitting president of its "imperialist enemy".
The North Korean autocrat's every move will be followed by 3,000 journalists who have converged on Singapore, and by gawkers around the world, up until he shakes hands with Trump on Tuesday.
Although there are geopolitical and security interests at stake for China in the negotiations, Beijing has refrained from direct involvement in the summit between Trump and Kim.
The KCNA report noted the summit is being held "under the great attention and expectation of the whole world".
Kim and Ri both joined Kim Jong Un for the April 27 inter-Korean summit, and Kim Yong Chol recently traveled to the U.S.to meet Secretary of State Mike Pompeo before delivering a letter from Kim Jong Un to Trump at the White House.
"[President Trump] is not going to permit any show of weakness on the trip to negotiate with North Korea", Kudlow said on CNN's State of the Union.
Sen. Bob Menendez of New Jersey says: "To the extent that Kim Jong Un has already gone from worldwide pariah to being normalized internationally, you have to say that he's had some success here".
When he previously appeared at the Pyeongchang Winter Olympics in South Korea with the same Donald Trump lookalike, he was escorted out by security after waving and dancing in front of North Korea's cheerleaders.
Asked whether he would sign onto an AUMF as an alternative, Menendez said, "I'm not ready to give an authorization for use of military force to this President or any other one until I understand the path for peace is not attainable, and the threat continues to be a real challenge to the national security of the United States, and we have all of the intelligence on a robust debate in the Senate on such an AUMF".
Trump descended from Air Force One into the steamy Singapore night, greeting officials and declaring he felt "very good", before he was whisked away to his hotel, driving along a route lined with police and photo-snapping onlookers.
Trump's planned meeting with Kim has also not been without controversy.
The US wants North Korea to give up its nuclear weapons but it is not clear what Pyongyang might want in return.
The North invaded the South in 1950 and the ensuing war saw US-led United Nations troops backing Seoul fight their way to a stalemate against Pyongyang's forces which were aided by Russian Federation and China, before the conflict ended in stalemate and an armistice which sealed the division of the peninsula.
Ahead of President Donald Trump's landmark summit next week with the North Korean leader, USA allies and many Republicans are raising concerns that he may impulsively give in on issues they say should be deal-breakers for the United States. Francis said he wanted yet again to send "a special thought in friendship and prayer" to the beloved Korean people.
Photographers are kept back from a meeting between North Korean leader Kim Jong-un and Singapore prime minister Lee Hsien Loong.
PM Lee is scheduled to meet Kim at the Istana on Sunday, and Trump on Monday.
"The entire world is focusing on the historic summit between the DPRK and the U.S., and thanks to your honest efforts. we were able to complete the preparations for the historic summit, and I would like to thank you for that", Mr Kim, speaking through an interpreter, told Mr Lee.
"This is a leader who really is an unknown personality", Trump added of Kim.
A jet carrying Kim landed hours earlier.
Trump on Sunday called the unprecedented summit, at which North Korea's nuclear arsenal will be at the top of the agenda, a "one-time shot" at peace.
"The people know these are all lies because it's obvious".