In the hours before the summit began, Trump expressed optimism about prospects for the first-ever meeting of sitting US and North Korean leaders, while US Secretary of State Mike Pompeo injected a note of caution whether Kim would prove to be honest about his willingness to denuclearise.
Critics said the pomp and ceremony lent too much prestige to Kim, a dictator who imprisons his opponents, murders his opponents, and has pursued long-range nuclear weapons.
North Korean leader Kim Jong Un's motorcade arrives at the Capella Hotel.
"The world will see a major change", he continued through a translator.
It was a day of pleasantries, but little public substance.
The size appeared created to match the number of North Korean "journalists" present, according to a press pool, and led to tension between USA media and White House officials on the ground in Singapore. "I also think I'll know if it's going to happen fast - it may not, but I'll know pretty quickly whether or not in my opinion something positive will happen".
The Associated Press reported that while the press corps and White House have an agreement to allow a full pool of reporters into any meetings where media is allowed, reporters for the AP and other outlets were kept out of some events at the Singapore summit.
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Pompeo is scheduled to immediately fly to Seoul and Beijing after the summit to brief South Korean allies and Chinese officials on the discussions, reflecting the reality than any solutions in the region will need buy-in from those nations. "We will be fine!"
North Korea granted such access as part of a Clinton-era diplomatic deal and agreed to freeze its nuclear material production. "But", he added, "'The Apprentice' had more likable characters, more credible plots, and didn't involve the enslavement of 25 million people or prospect of nuclear war".
At dawn, three hours before the summit was due to begin, Trump focused on his domestic audience reminding them of the economic successes of his presidency, with the stock market up and unemployment down.
"The discussions between the United States and North Korea are ongoing and have moved more quickly than expected", the White House said in a statement.
After greeting each other for the first time at 9 a.m. Tuesday Singapore time - 9 p.m.
After being driven separately to the resort island of Sentosa, the two leaders shook hands and exchanged a few words on the steps of the Capella Hotel.
In a September 2017 speech in front of the United Nations, President Trump referred to Kim as "Rocket Man" and threatened to "totally destroy North Korea", which earned a rare rebuke directly from Kim describing the president as a "frightened dog" and "mentally deranged US dotard". This week, the president said he looked forward to getting to know his new negotiating partner. It's a price they are willing to pay for peace. Technically, both Koreas remain at war; only a cease-fire ended the Korean War in 1953.
Each plans to leave Singapore hours after their meetings wrap up, though Trump plans to speak to reporters about the developments. On Monday night, he strolled the downtown area of this trade and finance capital, taking in the sights and posing for selfies with local citizens.
"There were a lot of obstacles on the way here", he said, "but we overcame them all". "If we say we need to fundamentally change the relationship, then you have a framework where there can be real progress". "Both leaders will want to trumpet it as a success, but it seems like this will largely be a photo op both can use for their domestic purposes".
Trump is set to meet with Lee on Monday. That could lead to misunderstandings, he said, if there are no witnesses to record what is said.
The one-on-one meeting lasted for about 30 minutes and was followed by a bigger group meeting that included Secretary of State Mike Pompeo, Chief of Staff John Kelly and National Security Adviser John Bolton.
Trump predicted earlier Monday that the summit could "work out very nicely" as officials from both countries sought to narrow differences on how to end a nuclear standoff on the Korean peninsula.
But a war would mean devastating casualties, including of American troops in South Korea, and American cities would also be at risk of suffering a nuclear strike because of the North's recent advances. Past nuclear deals have crumbled over North Korea's reluctance to open its doors to outsiders. Some supporters have said he could win the Nobel Peace Prize.
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Trump's one-on-one meeting with Kim kicks off the first ever summit between a sitting USA president and a North Korean leader. USA and North Korean officials are set to meet Monday morning in Singapore to make final preparations for Tuesday's meeting.