If Donald Trump meets with Kim Jong Un sometime this spring, he’ll be the first sitting American president to meet with a North Korean leader. There are many reasons for that.

Speaking to reporters after the surprise announcement Thursday, a senior Administration official touted the fact that Trump is willing to do what his predecessors would not.

“President Trump has made his reputation on making deals,” the official said. “Kim Jong Un is the one person who is able to make decisions under their authoritarian, uniquely authoritarian, or totalitarian system, and so it made sense to accept an invitation to met with the one person who can actually make decisions instead of repeating the sort of long slog of the past.”

It’s not that previous presidents didn’t have the option of meeting with the head of the hermit kingdom. “North Korea has been seeking a summit with an American president for more than twenty years,” Jeffrey Lewis, director of the East Asia Nonproliferation Program at Middlebury Institute of International studies tweeted Thursday night. “It has literally been a top foreign policy goal of Pyongyang since Kim Jong Il invited Bill Clinton.”

For starters, the United States is still technically at war with the isolated country: an armistice halted Korean War fighting in 1953, but neither the U.S. nor South Korea formally inked a peace deal.

President Bill Clinton didn’t go meet with Kim Jong Un’s father himself, but eager for a diplomatic win at the end of his presidency, he sent Secretary of State Madeleine Albright for the meeting in 2000. Writing in the New York Times in 2017, Albright recalled, “I held two days of intensive talks, during which [Kim Jong Il] appeared willing to accept more significant restraints on the missile programs than we had expected.” But she continued, “Obviously, if this dilemma were easy to resolve, it would have been settled long ago. The fundamental problem is that the North Korean leadership is convinced it requires nuclear weapons to guarantee its own survival.”

When George W. Bush came into the Oval Office soon after, he took a more hardline approach to North Korea, halting the negotiations that began under Clinton and Albright and naming the country part of an “axis of evil” in 2002. In 2006, North Korea tested its first nuclear device. The following year, Bush reportedly wrote a personal note to Kim Jong Il, “in which he held out the prospect of normalized relations with the United States if North Korea fully disclosed all nuclear programs and got rid of its nuclear weapons,” according to the New York Times. In his last year in office, Bush authorized the removal of North Korea from the list of state sponsors of terrorism (last year, Trump put the country back on the list). He hoped the move would salvage a faltering diplomatic process but ultimately the effort failed.

Although Bush wasn’t successful in denuclearizing the country, Bush’s former deputy press secretary Tony Fratto weighed in favorably on Trump’s decision on Twitter Thursday. “There’s nothing wrong with meeting, even if the chances of success are exceedingly slim,” he wrote. “Kim & his father have played the freeze game before. But the other options are military strikes, or years (decades?) more of privation for millions of innocents in NK. So talk.”

After Bush, President Barack Obama was open to talks, but never became convinced that North Korea would meet his preconditions or seriously intended to give up its nuclear weapons. “This is the same kind of pattern that we saw his father engage in and his grandfather before that,” Obama said of Kim Jong Un in 2013, who took over the country from his father in 2011 and had been making threats against the U.S. and South Korea. “Since I came into office, the one thing I was clear about was, we’re not going to reward this kind of provocative behavior. You don’t get to bang your spoon on the table and somehow you get your way.” As he was leaving office, Obama reportedly warned Trump that North Korea would be his most urgent foreign policy threat.

Each of the recent presidents before Trump struggled with North Korea, and none was able to get to a point where he felt that the country’s leader would come into a good-faith negotiation where denuclearization was seriously on the table. “To be clear — we need to talk to North Korea,” Lewis explained in a follow-up tweet. “But Kim is not inviting Trump so that he can surrender North Korea’s weapons. Kim is inviting Trump to demonstrate that his investment in nuclear and missile capabilities has forced the United States to treat him as an equal.”

Trump thinks things will be different for him. Since Trump became president, he and Kim have taunted each other from across the world, with Trump calling Kim “little rocket man,” Kim calling Trump a “dotard,” and the two comparing the size of their proverbial nuclear buttons. But on Tuesday, Trump said he believed North Korea to be “sincere” in showing willingness to halt nuclear tests. And Thursday night, South Korean National Security Advisor Chung Eui-Yong revealed outside outside the White House that Trump “would meet Kim Jong-un by May to achieve permanent denuclearization.”

It’s a risky move. “A Trump-Kim summit is a major diplomatic gamble,” Richard Fontaine, president of the Center for a New American Security, tweeted Thursday. “Talks can be good, but a summit should be a carrot for the end of a satisfactory process, not the beginning. High chance Kim will pocket the optics, show his people and the world he is received as a legitimate head of state, and in the end keep his programs intact.”

“I’d love to be more optimistic,” Fontaine added. “But we’ve been down similar roads numerous times with North Korea. Is this time different? Unlikely.”

What will be different this time is the fact that a U.S. president is actually sitting down in person with the North Korean leader. And Trump, at least, is betting that will make all the difference in the world.

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Write to Tessa Berenson at tessa.berenson@time.com.