South Korean President Moon Jae-in was instrumental in facilitating the summit and has staked much of his political capital on a rapprochement with Pyongyang.
"Chairman Kim is anxious about whether he can trust that the USA will end the policy of hostility and guarantee the stability of his regime", the South Korean President told the media upon his secretive meeting with Kim in May.
The two leaders are scheduled to meet for the first time on Tuesday at the Capella Hotel on Sentosa Island, where the process regarding denuclearisation of North Korea may kick-start in exchange for economic aid.
"No matter what happens, President Trump and Kim Jong Un are going to call it a success because both leaders are invested in this and they want to", Sue Mi Terry, Korea chair at the Center for Strategic and International Studies (CSIS), said at a press briefing.
The summit provides "an unprecedented opportunity to change the trajectory of our relationship and bring peace and prosperity" to North Korea, Pompeo told a news conference on the eve of the summit.
According to National Security Council spokesman Robert Palladino, President Trump intends to meet one on one with Kim.
Trump has even floated the idea of extending this week's summit for a second day, and maybe inviting Kim to the United States for further meetings.
So the summit was almost derailed by talk from Trump's hawkish National Security Advisor John Bolton of a "Libya model" of disarmament.
The Trump administration has previously insisted on "complete, verifiable, irreversible disarmament" (CVID) of North Korea, with the emphasis on unilateral steps by Pyongyang rewarded by U.S. security assurances.
Enlarge this image
Whether such a deal can be done, Trump declared Saturday, is something he will know nearly from the moment they meet.
Rodman said he hopes everyone reads it before the summit and reiterated that "we've got the greatest negotiator of all time" to "show the world how it's done".
Preliminary meetings have already begun.
"Donald Trump is not going to capitulate, so there's really only two options- peace or war".
The understated photo op belied the intensive behind-the-scenes negotiations that continued between the USA and North Korean delegations less than 24 hours before Trump was scheduled to meet Kim at the Capella Hotel on the resort island of Sentosa, just off Singapore's southern coast.
The Singaporean delegation also surprised the U.S. leader with a birthday cake.
Security is tight ahead of the summit between two unpredictable men who in the past have threatened to destroy the other's country during the stand-off over North Korea's nukes. The leaders are spending the night at hotels about a half-mile apart in the upscale shopping area in Tanglin.
Chairman Kim thanked Singapore's organisation of the summit as if it was "their own family affair".
Given the importance surrounding the on-again, off-again, and back on-again meeting between these two, it's hard to foresee what possible support that Rodman could offer these leaders in their high-wire negotiations. He sees the summit not as a means to an end, but the end itself.