And there Trump is gambling he'll be able to set the adversaries on a path toward dismantling North Korea's nuclear program, the likes of which has eluded US presidents for decades.
The meeting follows the historic summit between Kim and South Korean President Moon Jae-in in April, when the North and South vowed to work together to formally end the Korean War. And the United States has misread North Korea before.
"We're starting off on a new footing", Trump said. He hailed their release as a potential breakthrough in relations between the longtime adversary nations.
"So the relationship is good, and hopefully, for all of us, for the world, hopefully something very good is going to happen", he said. "I don't see any scenario he is going to give that up quickly, willingly, and so I think what he's trying to do is to, again, present an appearance of accommodation".
Ensuring that North Korea lives up to its commitment to give up its nuclear weapons will be far more hard than it sounds, given that it would probably require the sort of onerous and highly invasive inspection regime - with access to previously secret sites - that North Korea has resisted in the past.
The military hospital that received the three Americans released by North Korea says they will be reunited with their families once they have achieved what hospital officials call "an optimal period of decompression".
The ceremony, which also featured a giant American flag suspended between the ladders of two firetrucks, emphasized Trump's penchant for the dramatic as he raised expectations for the summit.
He previously taught Korean at Yanbian University of Science and Technology in Yanji, China, not far from the North Korea border.
Similarly, Trump would do well to think of United States troops in South Korea as keeping the Chinese out, the Americans in and the North Koreans down.
In the hours following the release of Kim Dong-chul, Tony Kim, and Kim Hak-song, the President ended weeks of speculation by announcing that his upcoming meeting with Kim Jong Un will be held in Singapore on June 12.
They appeared exhausted but in excellent spirits, flashing peace signs and waving their arms as they emerged from the aircraft.
"Singapore has been a great friend to the U.S. but also Singapore has carefully worked to be a friend to all, which has earned it trust in capitals around the world", he said.
Trump thanked North Korean leader Kim for releasing the Americans and said, "I really think he wants to do something" on denuclearization.
South Korea government said it had high hopes for the summit.
On the flight back from North Korea, Pompeo told reporters that the location and time of the summit had been agreed, but said details would be forthcoming in the next few days. If that's the Trump Doctrine, it would be a disaster for the United States and the world.
As for the venue, why Singapore?
Located at the southern tip of Malaysia, Singapore is a regional hub in Southeast Asia whose free enterprise philosophy welcomes trading partners from everywhere.
On the brink of starvation, she and her brother burned so hot with fever that they could only find relief on the cold concrete floor of their home in rural North Korea.
Unification Ministry spokesman Baik Tae-hyun did not provide a clear answer on whether the women could be returned to North Korea if it's confirmed they didn't want to come to South Korea.
Department officials took great pains on the prisoners' release in North Korea, as well as on their flights to Japan and Alaska, to keep them sequestered not only from the two journalists traveling with Pompeo but also from staffers not immediately involved in their cases. President Donald Trump is on hand to greet them. "I'm delighted to bring home three Americans".
He made at least seven trips to North Korea to teach.
When Trump and Kim sit down in the sweltering Southeast Asian city state, the two relatively new and untested leaders face a nuclear puzzle that has eluded seasoned diplomats for decades. Other foreigners have publicly admitted crimes but have said later their confessions were given involuntarily.
A series of USA administrations have sent envoys, both official and unofficial, to Pyongyang in the hope of stopping North Korea's provocative nuclear weapons programme.