The president views the meeting as the first of perhaps several meetings with Kim, and the tangible "deliverables" are hard to forecast. "It is a historic negotiation, and there is no way this president is not going to stand strong", Kudlowsaid.
But critics have warned that the meeting risks being largely light on substance considering what is believed to be a wide gap between the USA and the North on the denuclearization issue. The two men are set to meet for a historic summit on Tuesday where they will focus on the denuclearization of the Korean Peninsula in exchange for the easing of both economic and diplomatic sanctions.
At their summit in April Kim and South Korean President Moon Jae-in agreed to seek a peace treaty and Trump mused earlier this month: "Can you believe we're talking about the ending of the Korean War?"
In tamping down expectations, Trump himself has described this initial meeting as the start of a process. Progress could lead to a peace treaty and formally end a state of war on the Korean peninsula, which has persisted for almost 70 years. Volatility and the Trump-Kim pairing go together like joint statements and the phrase "constructive talks".
White House press secretary Sarah Huckabee Sanders told reporters that veteran diplomat Sung Kim is leading the US delegation in a working group meeting Monday at the city-state's Ritz Carlton hotel.
Trump arrives in Singapore ahead of historic North Korea summit
Menendez spoke Sunday on ABC's "This Week" as President Donald Trump arrived in Singapore ahead of Tuesday's talks with Kim. The official said Trump and Kim would hold a one-on-one meeting on Tuesday that could last up to two hours.
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 worldwide endeavour. Why only potentially? That's because these two world leaders are not, strictly speaking, known to be very diplomatic - that is to say that they are in no manner of speaking, known to be very diplomatic at all.
"I'm very confident the relationships between our countries, the United States and those G-7 countries, will continue to move forward on a strong basis", Pompeo said.
Kim Jong Un will undoubtedly get a sense of all that as he arrives.
Ponsei University's John Delury told Singapore broadcaster AsiaNews that Trump was a disruptive force in traditional diplomacy but his tactics of a one-on-one meeting could work. Kim, up until his recent high-profile summit with South Korea's president on the southern side of their shared border, has usually hunkered down behind his vast propaganda and security services, or made short trips to autocrat-friendly China.
North Korean state-run news reported Monday that Mr. Kim was seeking denuclearization of the Korean Peninsula in response to a "changed era".
While Singapore has authoritarian leanings, it is still a thriving bastion of capitalism and wealth, and Kim will be performing his high-stakes diplomatic tight-rope walk in front of 3,000 global journalists, including a huge contingent from the ultra-aggressive South Korean press - sometimes referred to by Pyongyang as "reptile media" - two of whom were arrested by Singapore police investigating a report of trespassing at the residence of the North Korean ambassador.
Earlier this morning, the tweeter-in-chief expressed his elation about being in Singapore and feeling "excitement in the air".