For a property developer-turned-president, the tête-à-tête, scheduled for Tuesday in Singapore, is a long-anticipated test of Mr. Trump’s conviction that he can slice through decades of diplomatic orthodoxy and strike a grand bargain with North Korea, a feat that eluded his three immediate predecessors.
Mr. Trump, current and former aides said, has been preoccupied with North Korea since his predecessor, Barack Obama, warned him in a closed-door meeting two days after he was elected that the reclusive state would be his No. 1 foreign policy challenge. But he has been tantalized by the idea of solving the North Korea problem since long before that.
.. “If a man walks up to you and puts a gun to your head and says, ‘give me your money,’” Mr. Trump said in 1999, “wouldn’t you rather know where he’s coming from before he had the gun in his hand?”
.. Aides say he has mused about the motives of Mr. Kim, who, like him, is a scion born into wealth and privilege, with a skill for self-promotion and an ambition to be a major player.
.. “This is something that Trump has thought about for a long time, even before the election,” said Joseph Y. Yun, a former top Korea negotiator at the State Department
.. If Mr. Kim makes any moves toward disarmament, he is likely to press for security guarantees in exchange. The danger, Mr. Yun said, is that Mr. Trump does not understand the complex dynamics of security on the Korean Peninsula, where 28,500 American troops are deployed to keep the peace in a war that, as the president himself recently noted with wonder, never formally ended.
.. Mr. Trump left little doubt that he would improvise. “It will be something that is always spur-of-the-moment,”
.. The National Security Council has held no high-level meetings to devise a strategy for how to negotiate with him. In part, officials said, that reflects the recognition that whatever his briefing papers say, Mr. Trump will act on instinct once he is across the table from Mr. Kim.
.. Mr. Trump was steeped in the heroics of a Korean War commander, Gen. Douglas MacArthur. The brilliant tactician who led the amphibious assault at Inchon in 1950, MacArthur later clashed with Harry S. Truman, who fired him for insubordination. At Mr. Trump’s school, however, he remained a hero: When he died in 1964, the class organized a tribute.