The jet carrying Kim landed at the airport Sunday afternoon amid huge security precautions on this city-state island.
The despot took a break from official government business on Monday to take a mini tour with Singapore Foreign Minister Vivian Balakrishnan, his sister and other top deputies. He said that those talks "in fact are moving quite rapidly and will come to a logical conclusion more quickly than anticipated".
Regardless, Trump seemed determined to keep his meeting with Kim low-key, dangling the possibility of a future summit in the USA if things go well this week.
Trump, speaking in Canada on Saturday, said any agreement at the summit would be "spur of the moment", underscoring the uncertain outcome of what he called a "mission of peace".
And accordingly to Lee Yun-keol, who worked in a North Korean Guard Command unit before defecting to South Korea in 2005, that's par for the course. They will be joined only by translators and will spend a couple of hours before admitting their close advisers to the meeting.
'Cheating Every Time'North Korea has previously promised to denuclearize, only to continue its nuclear program after receiving concessions from the United States, said Michael J. Green, senior vice president for Asia and Japan Chair at the Center for Strategic and International Studies.
An aviation source in China said that "It probably cost a lot of money as well as representing a huge political burden to loan Kim the aircraft", the publication Chosun Ilbo reported.
As Trump and Lee sat down for a working lunch at the Istana house, the president sounded optimistic, telling Lee, "We've got a very interesting meeting in particular tomorrow, and I think things can work out very nicely".
"I feel that Kim Jong-Un wants to do something great for his people".
This time they had it a bit easier, though - as the North Korean leader preferred to walk nonchalantly, enjoying the evening and clearly not being in a hurry.
While fighting a trade war with allies, Trump now brings his America First negotiating style to the deadly topic of North Korea's nuclear weapons. And the maximum, I think you know the answer to that.
Before flying to Singapore, Mr. Trump was in Canada for the G-7 summit with leaders from Canada, France, Germany, Italy, Japan and the U.K. All seven leaders had worked out a joint statement stressing the importance of a rules-based worldwide trading system.
The North has faced crippling diplomatic and economic sanctions, which began years before Trump's "maximum pressure" campaign, as it has advanced development of its nuclear and ballistic missile programs. "Just my touch, my feel".
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I knew that question would come, but I like to be here. "I have no idea at this point", James told reporters. What either factor will mean for James' upcoming decision will be determined in the coming weeks.
Trump, Macron cool down the buddy act at Canada's G7
Leaders have struggled to find ways of getting through to Trump and persuading him to budge from his pre-established positions. The G-7 groups Britain, Canada, France, Germany, Italy, Japan and the United States, plus the European Union.