If April's Inter-Korea Summit was the crack in the dam holding the world back from Pyongyang, Tuesday's Trump-Kim meeting could potentially represent the total collapse of the dam that brings the world surging towards North Korea. The official was not authorized to speak publicly about internal deliberations and insisted on anonymity. The truest measure of the success of the Singapore Dialogue will be an agreement by Trump and Kim to meet again in the near future.
Trump and Kim arrived in Singapore hours apart Sunday. 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.
While he famously attended school in Switzerland, traveling this far as supreme leader is an entirely different matter for someone used to being the most revered, most protected, most deferred to human in his country of 25 million.
Kim is expected to stay at the St Regis hotel and Trump at the Shangri-La, both in the Tanglin area in downtown Singapore.
Trump expressed optimism about Tuesday's meeting during a working lunch with Singapore's Prime Minister Lee Hsien Loong and aides to both leaders.
Kim met with Singapore's Prime Minister Lee at his Istana residence after his arrival, in talks which North Korea's KCNA news agency said proceeded "in an amicable and friendly atmosphere".
Kim told Lee: "The entire world is watching the historic summit between the DPRK and the United States of America, and thanks to your honest efforts. we were able to complete the preparation for the historic summit".
Despite this emphasis on first impressions, Trump began the Singapore summit by signaling to Kim that he's the kind of guy who refuses to put his phone down during dinner, and can't stop talking about his ex.
Ahead of his much-anticipated meeting with Kim, the US President sounded optimistic and said the meeting would be a "one-time shot" at peace.
He initially touted the potential for a grand bargain with North Korea to rid itself of a nuclear missile program that has advanced rapidly to threaten the United States.
Many experts on North Korea, one of the most insular and unpredictable countries in the world, remain skeptical Kim will ever completely abandon nuclear weapons.
The standard thinking goes that he needs quick help to stabilize and then rebuild an economy that has suffered amid a decades-long pursuit of nuclear bombs, and that the North Koreans see a unique chance to win concessions, legitimacy and protection from a meeting with a highly unconventional USA president who's willing to consider options past American leaders would not.
Trump also reaffirmed the tight US-Singapore relations by reassuring PM Lee that he was "his friend".
"When I woke up this morning I saw the news in the newspaper that our respected Marshal went to Singapore for the North Korea-U.S. summit", said Han Il Gwang, a Pyongyang resident, displaying typical discretion when speaking to an Associated Press Television crew. "North Korea's nuclear command, control, communications and intelligence is configured to promote a high degree of centralization in Kim's decision-making, it beggars belief that Kim would not be within secure reach to authorize a possible launch if required", O'Neil added. In subsequent years, the US and South Korea signed a mutual defence treaty, but nothing for the North.
South Korean media also claims there were fears that Kim's Soviet-era plane might not survive the trip.
Singapore has spent $S20 million hosting the summit, half of that on security costs, with Lee saying it was "in our profound interest" to contribute to such an global endeavour.