"It's very hard for me to imagine this summit not succeeding", said Robert L. Gallucci, a former chief US negotiator with the North Koreans, although he acknowledged that a sudden meltdown in Singapore could trigger a quick reversal to the threat-soaked posturing between Mr. Trump and Mr. Kim just a year ago.
Kim is hoping Trump will relieve the economic sanctions that have crippled the North Korean economy.
"And I don't think either interpreter will be in a position to correct the record if the self-reporting by Kim and Trump doesn't reflect what was actually said in the same manner and tone", said Jenny Town, assistant director of the U.S. -Korea Institute at Johns Hopkins University.
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But on the eve of the summit, the White House unexpectedly announced Trump would depart Singapore by Tuesday evening, meaning his time with Kim would be fairly brief.
The White House said the summit was to kick off at 9 am Tuesday. Both leaders were greeted on arrival by Singapore Foreign Minister Vivian Balakrishnan. "We would like to make sure this message will be conveyed (to Kim)", said Sakie Yokota, 82, whose daughter Megumi was kidnapped at age 13 on her way home from school in Niigata Prefecture in 1977.
"I'm very optimistic that we will have a successful outcome from our meetings tomorrow", he said.
US and North Korean officials huddled throughout Monday at the Ritz-Carlton hotel ahead of the sit-down aimed at resolving a standoff over Pyongyang's nuclear arsenal.
"If diplomacy doesn't move in the right direction, sanctions will increase", Secretary of State Mike Pompeo says.
He has made two trips to China since March to meet President Xi Jinping, and held summit talks with South Korean President Moon Jae-in in April and May in the Demilitarized Zone, which separates the two Koreas.
North Korea summit: How Trump will communicate, negotiate with Kim Jong Un
It started with significant diplomatic overtures from North Korea towards South Korea during the Winter Olympics. So, in this respect at least, it seems this historic summit is no different than Kim's other excursions.
They came with scores of aides, bodyguards and diplomats in tow: Donald Trump from Washington, Kim Jong Un from Pyongyang.
Trump, asked last week if Rodman had been invited to Singapore, said, "No, he wasn't".
Ordinary North Koreans citizens are not allowed to travel, so seeing a North Korean in the flesh is a thrilling affair.
Trump and Kim arrived in Singapore on Sunday, both staying at luxurious and heavily guarded hotels about a kilometre and a half apart, with Trump at the Shangri-La Hotel and Kim at the St. Regis Hotel.
The North has presented Kim's sudden diplomatic overtures to the country's neighbours and the U.S. as a logical next step and completion of his plan to develop a credible nuclear deterrent in response to what Pyongyang says is a policy of "nuclear blackmail" by Washington. Early in Trump's presidency, he raised eyebrows when he met with Russian President Vladimir Putin during a conference in Germany with only a Kremlin translator present.
"Just my touch, my feel", Trump replied. This is just an elaborate get-to-know-you session, albeit between the two most famous leaders in the world, and nuclear armed at that.
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It also tells us that the game can be completed in one sitting, so The Quiet Man is definitely an intriguing game. In the middle of the trailerfest, Square Enix dropped a new IP with a minute-long teaser and a title.