The impulsive American president, who just this weekend sowed chaos within the Western alliance, is set to face his match on the global stage as he prepares to meet Kim in Singapore on Tuesday.
In the historic first meeting between the leaders of the technically-still-warring nations, Trump is prioritizing instinct over planning. Unlike traditional summits between heads of state, where most of the work is completed in advance, U.S. officials say the only thing certain ahead of these talks will be their unpredictability.
Ever since Trump shocked allies, White House officials and, by some accounts, the North Koreans themselves when he accepted Kim's March invitation for a meeting, the two leaders have lurched toward an uncertain encounter that could affect millions.
"It's unknown territory in the truest sense, but I really feel confident," Trump told reporters Saturday. "I feel that Kim Jong Un wants to do something great for his people and he has that opportunity and he won't have that opportunity again."
Trump landed in Singapore on Sunday evening, about four hours after Kim arrived in the island city-state. The two are scheduled to meet for the first time Tuesday morning.
Trump's engagement with Kim fulfills the North Korean ruling family's long-unrequited yearning for international legitimacy, itself a substantial concession after more than a generation of U.S. efforts to isolate the country on the global stage.
"It's never been done before," Trump said. "And obviously, what has been done before hasn't worked."
A triumvirate of forces is bringing the meeting to fruition, said Scott Snyder, senior fellow for Korea Studies and director of the Program on U.S.-Korea Policy at the Council on Foreign Relations. He describes the summit as "produced by Kim, directed by (South Korean President Moon Jae-in), and inspired by Trump."