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 US president who's willing to consider options past American leaders would not.
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.
Trump canceled the meeting, but chose to move ahead with it a week later after a visit to Washington by a top North Korean official.
In a post on Twitter during his flight, Trump reiterated his optimism that the summit with the North Korean leader will be a success.
Hours earlier, Kim had arrived in a jet and was received by Balakrishnan before heading to St Regis Hotel.
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Kim is now scheduled to leave Singapore around 2pm on Tuesday with Trump departing on Wednesday morning. Otherwise, the relationship between the two countries could quickly become fraught with frustration and misunderstandings.
Even after touching down in Singapore, it was clear that the trade disputes with USA allies in Quebec continued to rankle Trump.
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The outcomes of Tuesday's unprecedented meeting are highly uncertain, but analysts say that the mere fact is happenng is a step forward.
He says the U.S.is prepared to show North Korea that rather than denuclearization posing a threat to North Korea, it's "the opposite".
The tests culminated in November's test of an intercontinental ballistic missile that North Korea said could reach the entirety of the United States.
But in his new diplomatic role - until March he had not left his country for more than six years - Kim has come across as polite, respectful and even charming in meetings with the Chinese and South Korean leaders.
"We've got a very interesting meeting in particular tomorrow, and I just think it's going to work out very nicely", Trump said.
Experts believe the North is on the brink of being able to target the entire USA mainland with its nuclear-armed missiles, and while there's deep skepticism that Kim will quickly give up those hard-won nukes, there's also some hope that diplomacy can replace the animosity between the United States and the North.
Monday's meeting is apparently aimed at narrowing the gap between the USA and North Korea over the demand for North Korea to give up its nuclear weapons.
Among those representing the U.S. at the lunch were Secretary of Secretary Mike Pompeo, White House Chief of Staff John Kelly and National Security Adviser John Bolton.
The White House and State Department have said little about those talks, though people briefed on them said American negotiators found it difficult to make significant headway with the North Koreans, in part because the White House did not back them up in taking a hard line.
But he has since lowered expectations, backing away from an original demand for North Korea's swift denuclearization.