Trump arrived a few hours after Kim on Air Force One, directly from a tumultuous G7 summit in Quebec, which ended in a bitter personal exchange between the United States president and the host, the Canadian prime minister, Justin Trudeau.
Although gaps remain over what denuclearisation would entail, Trump sounded a positive note in a lunch meeting with Singapore's Prime Minister Lee Hsien Loong.
The meeting was kicking off at 9 a.m. Tuesday with a handshake between Trump and Kim. Traffic was held up in the steamy midday sun and scores of bystanders were penned in by police when Trump went to meet Lee.
U.S. presidents and vice-presidents generally never fly on the same aircraft to guarantee that one of them survives in the event of a disaster, and the move appeared created to ensure the preservation of the Kim dynasty, which has ruled the North for three generations.
Another possibility from the summit is a deal to end the Korean War, which North Korea has long demanded, presumably, in part, to get US troops off the Korean Peninsula and, eventually, pave the way for a North Korean-led unified Korea.
As Kim's black Mercedes arrived at the St Regis hotel in downtown Singapore, it was flanked by bodyguards in identical black suits jogging alongside the auto. Earlier this month, Singapore's defense minister said the USA trade threats were as disruptive to the global order as China's military deployments in the disputed South China Sea.More news: U.K. Minister Phillip Lee Resigns Ahead of Brexit Bill Showdown
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Part of the interest in Tuesday's summit is simply because Kim has had limited appearances on the world stage. Trump left the summit early, and as he flew to Singapore, he tweeted that he was yanking the US out of the group's traditional closing statement.
Trump advisers cast his actions as a show of strength before the Kim meeting.
Trump and Kim are set to meet on Tuesday at the Capella Hotel in Sentosa for talks, which could see North Korea dismantle its nuclear arsenal in return for economic help and security guarantees. Both leaders were greeted on arrival by Singapore Foreign Minister Vivian Balakrishnan.
He would not say whether that included the possibility of withdrawing USA troops from the Korean Peninsula, but said the context of the discussions was "radically different than ever before".
The Rodong Sinmun newspaper, the mouthpiece of the ruling Workers' Party, devoted its first two pages and 16 photos to Kim's trip, including images of him boarding an Air China Boeing 747 for the journey.
UN Security Council Resolution 2270 forbids loaning aircraft, ships and crew to North Korea, but Beijing apparently had US approval. He told Lee: "We've got very interesting meeting in particular tomorrow, and I just think it's going to work out very nicely".