Meeting With Kim Tests Trump’s Dealmaking Swagger

President Trump this month at the White House with Kim Yong-chol, left, North Korea’s top nuclear arms negotiator, and Secretary of State Mike Pompeo.

SINGAPORE — When President Trump declared that he did not really need to prepare for his legacy-defining meeting with North Korea’s leader, he drew sighs or snickers from veterans of past negotiations. But he had a point: In his own unorthodox way, Mr. Trump has been preparing for this encounter his entire adult life.

For an American leader who came of age in the early 1960s, when the United States and the Soviet Union stepped to the brink of nuclear annihilation, the meeting with Kim Jong-un strikes a personal chord, offering Mr. Trump a historic chance to rid the world, and his own presidency, of the greatest threat from atomic weapons.

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.

Nineteen years ago, when the threat from Pyongyang was a fraction of what it is today, Mr. Trump said he would “negotiate like crazy” with North Korea’s leaders before considering a military strike. In May 2016, while running for president, he said he would sit down with Mr. Kim — an offer he repeated even when threatening to rain “fire and fury” on him if North Korea targeted America.

“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?”

Unlike other foreign policy issues, where Mr. Trump seems neither informed nor particularly interested, he has wrestled with the balance between threats and cajolery with North Korea. 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, who resigned this year out of frustration that diplomacy with Pyongyang was not moving quickly enough.

The administration conducted a major review of North Korea policy a month after Mr. Trump took office, and the campaign of “maximum pressure” against the North — a phrase the president has since disavowed — was one of its first, and arguably most successful, initiatives.

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Trump Talks Tough at G-7 Ahead of North Korea Summit

At the meeting of the Group of 7 nations on Saturday, President Trump threatened to end trade with countries he says follow unfair trade practices and displayed confidence about the upcoming talks with North Korea.

Tariffs are going to come way down, because we people cannot continue to do that. We’re like the piggy bank that everybody’s robbing, and that ends. It’s got to change. It’s going to change. I mean, it’s not a question of, I hope it changes. It’s going to change, 100 percent. I will say it was not contentious. What was strong was the language that this cannot go on. But the relationships are very good, whether it be President Macron or with Justin [Trudeau]. So I don’t blame them. I blame our leaders. In fact, I congratulate the leaders of other countries for so crazily being able to make these trade deals that were so good for their country and so bad for the United States. But those days are over. In just a few minutes, I’ll be leaving for Singapore. I’ll be on a mission of peace. We have to get denuclearization. We have to get something going. We really think that North Korea will be a tremendous place in a very short period of time. You know the way they say that you know if you’re going to like somebody in the first five seconds? You ever hear that one? Well, I think that very quickly I’ll know whether or not something good is going to happen. I also think I’ll know whether or not it will happen fast. I think within the first minute I’ll know. Just my touch, my feel. That’s what, that’s what I do. But I really feel confident. 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.

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At the meeting of the Group of 7 nations on Saturday, President Trump threatened to end trade with countries he says follow unfair trade practices and displayed confidence about the upcoming talks with North Korea.CreditCredit...Doug Mills/The New York Times

“In that sense, he is pretty well prepared,” Mr. Yun said.

That does not mean that Mr. Trump intends to dive into the details. But in that, he may not be alone: The summit meeting, should Mr. Kim choose to follow in the tradition of his father and grandfather, could turn out to be primarily the get-to-know-you session that many expect.

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.

“Does Trump recognize what it means to remove extended deterrence?” Mr. Yun said. “What it means to start peace negotiations? What it means to end the war?”

Mr. Trump’s preparation for those questions has fallen to Secretary of State Mike Pompeo, who helped arrange the summit meeting in two secret trips to Pyongyang. He bridled this past week at the suggestion that the president was not prepared. In his former job as C.I.A. director, Mr. Pompeo said, he briefed Mr. Trump on the history of the Korean conflict, the North’s military capabilities and the economic impact of the sanctions campaign.

“There were few days that I left the Oval Office after having briefed the president that we didn’t talk about North Korea,” Mr. Pompeo told reporters. “I am very confident the president will be fully prepared when he meets with his North Korean counterpart.”

As he left for Singapore on Saturday, however, Mr. Trump left little doubt that he would improvise. “It will be something that is always spur-of-the-moment,” he said to reporters at a Group of 7 summit meeting in Canada.

“This is a leader who really is an unknown personality,” he said. “People don’t know much about him. I think he is going to surprise on the upside.”

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.

But it also reflects deep divisions in the administration about the goals of the diplomatic opening to North Korea. Mr. Trump’s hawkish national security adviser, John R. Bolton, nearly derailed the summit meeting last month when he declared that Libya, whose leader, Col. Muammar el-Qaddafi, voluntarily turned over his entire nuclear infrastructure in 2003 and 2004, ought to be the template for the disarmament of North Korea.

The North Koreans lashed out at Mr. Bolton, pointing out that Qaddafi met a miserable fate — killed by his own people, in an uprising aided by a NATO bombing campaign. Mr. Trump complained bitterly to his staff about the comments — as did Mr. Pompeo — and officials said Mr. Bolton has been largely sidelined from the summit meeting preparations.

Much of Mr. Trump’s frustration, aides said, stemmed from his desire to make history and his belief — contrary to Mr. Bolton’s — that talking to Mr. Kim could yield a peaceful solution.

To some extent, the life-or-death issues at play today on the Korean Peninsula are the same ones that shaped Mr. Trump’s worldview. In 1959, six years after the armistice that halted the war, his father, Fred Trump, enrolled Donald as a cadet in the New York Military Academy.

Fred Trump chose the strict boarding school in Cornwall-on-Hudson mainly to straighten out his unruly son, then 13. But classmates of the future president said that while there, he got a firsthand taste of the terrors of the atomic age. In 1962, during Mr. Trump’s junior year, the United States and the Soviet Union almost went to war after the Soviet leader, Nikita S. Khrushchev, shipped missiles to Cuba to be pointed at American territory.

Mr. Trump and his classmates listened to the radio as President John F. Kennedy warned Khrushchev of American action if he did not pull back. At a time when students were used to air raid drills, the fears of these cadets went beyond the general dread of a nuclear exchange.

“Here we were, 60 miles outside of New York City, with rifles,” said Peter Ticktin, a lawyer in Florida, who was in his class. “We figured if the United States was attacked, we would have to keep order.”

For the cadets at the academy, the Korean War was less of a focus than the germinating conflict in Vietnam, where some would later serve and others, like Mr. Trump, would avoid through draft deferments — in his case because of his education and bone spurs in his feet.

But 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.

Among the general’s offenses: He repeatedly contradicted his commander in chief’s positions and called for expanding the Korean War to China, potentially with nuclear weapons. At Mr. Trump’s school, however, he remained a hero: When he died in 1964, the class organized a tribute.

“We sort of disregarded the controversy around MacArthur,” said George White, another classmate. “We just regarded him as a great commander.”

As a candidate, Mr. Trump regularly invoked MacArthur’s name, often to mock his opponents for their weakness. He once said of Hillary Clinton that she “tells you how to fight ISIS on her website. I don’t think Gen. Douglas MacArthur would like that too much.” Aides said the president has continued to talk about his exploits in the White House.

For Mr. Trump, they said, a deal with Mr. Kim would not just be about the nuts and bolts of disarmament. It would make him part of a chapter of history that has always resonated with him.

“To the president, ‘duck and cover’ and the Cuban missile crisis were formative experiences,” said Stephen K. Bannon, Mr. Trump’s former chief strategist. “He knows the Korean War hasn’t ended, and he can accomplish what destroyed his idol, General MacArthur.”

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