Mr Trump arrived in the country's Paya Lebar Air Base aboard Air Force One, having flown directly from the turbulent G7 meeting in Canada, where he fought with his supposed allies and refused to sign a joint communique.
Those hoping Mr Trump’s meeting with the North Korean leader helps bring about peace to the region and wider world, will be praying the US president is more diplomatic with Mr Kim than he was with Canadian prime minister, Justin Trudeau, who he called “very dishonest and weak”.
When he landed at around 8.20pm on Sunday, Mr Trump was asked by a reporter how he felt about the upcoming meeting, for which he has reportedly prepared minimally. He replied: “Very good.” His motorcade, including the reinforced “Beast” Cadillac limousine, made its way to the Shangri-La hotel, where a sweating line of photographers and a small crowd of people were waiting to see him pass.
“It’s exciting, but I am also anxious,” said a woman who asked to be identified only by her first name, Kim. “Kim can change his mind at any time. Mr Trump also likes to get his own way.”
She added: “But if it works, it’s for the good of the whole world. It will make history.”
Christine McDougal, a Singaporean resident and US citizen, had arrived with a friend to cheer the president’s arrival. “This is a such an important moment,” said the 16-year-old student.
Mr Kim had arrived earlier in the afternoon, touching down at the nation’s main airport, Changi, in a plane loaned to him by China. While North Korea has proved it has been able to create a successful intercontinental ballistic missile, there are questions about the air worthiness of its aircraft for anything other than short journeys. Like Mr Trump, Mr Kim was received at the airport by Singapore’s foreign minister, Vivian Balakrishnan.
He then made his way to the St Regis, one of the nation’s most exclusive and expensive hotels. It is understood that Singapore has agreed to meet the costs of Mr Kim’s bill.
While the two hotels were surrounded by media on Sunday, it will be the Capella hotel on the island of Sentosa, half a mile off shore, where all attention will turn on Tuesday. It is there, in a building designed by British architect Norman Foster, that Mr Trump and Mr Kim are due to meet, starting at 9am.
When Mr Trump initially agreed to meet with the North Korean leader, the US president spoke of his hope that their encounter could secure a major breakthrough and lead to the denuclearisation of the Korean peninsula.
If so, then the meeting would be the most important since Ronald Reagan met with Soviet leader Mikhail Gorbachev in Geneva in November 1985.
Mr Trump has since sought to play down expectations, saying that the meeting will be an important first step, but that securing a deal will likely take many more meetings.
Given that what the US wants to get out of the summit, a rapid denuclearisation of the Korean peninsula, may be different to what North Korea wants, there may be many such meetings. Many observers will be looking to see whether Mr Trump does extend an invitation to his counterpart to visit the White House.
Despite many observers playing down the likely outcome of Tuesday’s summit, the fact it is happening at all – the first such encounter between a North Korean leader and a sitting US president – is nothing short of remarkable. Last year, as North Korea stepped up its testing of missiles and fissile material, Mr Trump told the United Nations General Assembly the US may have to “totally destroy” North Korea, if it continued to threaten the region.
Earlier this year, he and Mr Kim, whom he dubbed “Little Rocket Man” swapped insults about the size of their nuclear arsenals. Yet since the remarkable breakthrough led by South Korea, at the Korean summit held in the demilitarised zone between the two nations, Mr Trump has appeared committed to meeting the long-sanctioned leader.
Reuters said that also travelling with Mr Kim were top officials including Foreign Minister Ri Yong-ho and Kim Yong-chol, a close aide of Mr Kim, who has been instrumental in the diplomacy leading up to Tuesday's summit.
Kim Yo-jong, Mr Kim’s younger sister, was also spotted in his delegation. She emerged as an influential figure in Pyongyang’s leadership in February, when she led a North Korean delegation to the winter Olympics in South Korea.
Officials who arrived with Mr Trump included Secretary of State Mike Pompeo, National Security Adviser John Bolton, White House Chief of Staff John Kelly and White House Press Secretary Sarah Huckabee Sanders.
Mr Trump and Mr Kim will have to work quickly if they are to achieve anything meaningful on this meeting. The Wall Street Journal said the North Korean leader is scheduled to leave at 2pm on Tuesday, just five hours after his meeting with the US president is scheduled to start.
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