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.
"[Kim] said that the coming DPRK-U.S. summit would be a historic meeting for the excellent first step toward promotion of the positive situation development in the Korean peninsula and building of a good future", KCNA said, in coverage of a Wednesday meeting between the DPRK leader and Secretary of State Mike Pompeo in Pyongyang.
Pyongyang has since said it will dismantle its nuclear test sites.
"There are measurable, meaningful things that North Korea could do, but nothing that the North Koreans have offered or promised or said to date can give us confidence particularly in light of their discouraging track record", said Danny Russel, former assistant secretary of state for East Asia and the Pacific, who's now vice president at the Asia Society Policy Institute.
Tony Kim, who also goes by the Korean name Kim Sang-duk, was detained on April 22, 2017, at the Pyongyang airport for committing "criminal acts of hostility aimed to overturn" North Korea, according to the North's Korean Central News Agency.
They appeared exhausted but in excellent spirits, flashing peace signs and waving their arms as they emerged from the aircraft.
When asked by reporters how it felt to be home, one of the men answered through a translator: "It's like a dream; we are very, very happy".
"Though we're not quite back home yet, I welcomed them back", Pompeo told Associated Press.
South Koreans Are Still Buzzing Over Last Month's Inter-Korean Summit The mood in South Korea after the meeting between leaders of the two Koreas is optimistic and euphoric.
Despite Detente, North Korea Warns US Against 'Stupid Behavior'
"You're never certain exactly what you're going to get into when you're dealing with certain governments that you don't always have a friendly relationship with", she said.
USA officials had also considered holding the summit at the Korean demilitarized zone or in Mongolia, but ultimately settled on the city-state of Singapore as the location.
Tensions began to ease earlier this year, coinciding with the North's participation in the Winter Olympics in South Korea in February.
Drawn to big moments and bigger headlines, Trump views the North Korea summit as a legacy-maker for him, believing that the combustible combination of his bombast and charm already has led to warmer relations between North and South.
The meeting has been compared to Richard Nixon when he met with Chinese leader Mao Zedong in 1972.
In a typical move, the historic announcement was made by Trump on Twitter.
But the Rodong Sinmun on Thursday still found room to denounce the U.S.in reference to the 1950-53 Korean War.
"We've consistently underestimated North Korea's military, nuclear and cyberattack capabilities", said Bart Kosko, professor of law and electrical engineering at the USC Gould School of Law and the USC Viterbi School of Engineering.
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. After being flown to a US military base in Japan, the men were taken to Joint Base Andrews in Maryland.