When Trump and Kim meet on Tuesday at Sentosa, a resort island off Singapore's port with a Universal Studios theme park and man-made beaches, they will be making history.
After a flurry of contacts between the two Koreas, South Korean officials suggested to Trump in March that Kim would be willing to meet face-to-face.
Trump was received by Lee at the presidential palace Istana, where they were expected to discuss everything from the summit preparations to the US' tariff threats.
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News that U.S. Secretary of State Mike Pompeo had visited North Korea and a big photo of him shaking Kim's hand appeared on the front page of the ruling party newspaper, the Rodong Sinmun, the following day.
Kim had arrived hours earlier in a plane loaned by China, which for decades has been North Korea's only major ally.
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.
Mr Kim was sent off in a ceremony at the Pyongyang airport joined by a group of senior officials, such as Mr Kim Yong Nam, the North's nominal head of state, Mr Choe Ryong Hae, vice-chairman of the North's State Affairs Commission, and Prime Minister Pak Pong Ju.
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He said Trudeau - whom at one point he said "staged" a "sophomoric political stunt for domestic consumption" and should apologize. He sent a tweet that suggested he stands by the G7 communique despite the president's second thoughts.
"The first minute I'll know - just my touch, my feel, that's what I do", Trump said over the weekend at the G-7 summit in Canada.
North Korea's state media usually only reports on Kim's movements after he has conducted his business.
But in early 2018, North Korea began attempts to improve relations with South Korea by sending a team and delegates to the Winter Olympics in Pyeongchang.
A US official said Monday that Trump and Kim will first meet one on one with translators in a session that could last up to two hours before they open the meeting to their respective advisers. Because, you know, as a deal person, I've done very well with deals.
It is an extraordinary turnaround from the tensions of previous year, when Kim accelerated his weapons programmes - earning the North more sets of UN Security Council sanctions - and the two men traded personal insults and threats of war. He called for North Korea to follow a "Libya model" in negotiations.
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Japanese Prime Minister Shinzo Abe flew to Washington last week to meet with Trump before the G7 to ensure Japan's interests weren't overlooked in the summit.