WASHINGTON DC (CNN) - What do you say to a rogue dictator of a repressive state?
To quote Frank Sinatra: "Come fly with me." Seriously.
A source confirms to CNN that this was exactly what former president trump did with North Korea's Kim Jong Un.
Air Force One - a symbol of American presidential power and prestige.
In 2019, a stunning invite from then-President Donald Trump to North Korean leader Kim Jong Un.
A former administration official tells CNN, Trump casually offered to fly Kim back to Pyongyang as he was walking out of denuclearization talks in Hanoi, Vietnam.
Trump “just did it for his friend,” the former official says, creating a potential logistical and security nightmare.
“I think it's clear Trump had no idea what he was doing and didn't really understand the kind of political constraints that somebody like Kim Jong Un would be under,” Jeffrey Lewis, professor at Middlebury Institute of International Studies said.
Trump’s former national security advisor John Bolton detailed the collapse of summit talks in his book, writing Trump “offered to fly him back to North Korea, canceling his evening in Hanoi.
Kim laughed and said he "couldn't do that.”
Trump abruptly canceled a working lunch, leaving the table empty.
“Kim Jong Un, his five-day train journey to get down there. Lots of build-up, and then to just be sort of dumped publicly," said Chad O’Carroll, CEO of Korea Risk Group. "I mean, I think it really, really upset Kim Jong Un.”
After the failed Hanoi Summit, Kim reportedly disciplined several high-ranking members of his entourage.
Ambassador Joseph Yun says U.S. and North Korea diplomacy under Trump never recovered.
“So, I think the first misstep was preparation was not enough," he said. "Second misstep was Trump pulling back and leaving early without sitting there and negotiating."
Yun says "the Air Force One offer was a failure to understand the North Korean leader's mindset."
“He wanted to appear as an equal. He got nothing in sanctions," he said. "So, a plane ride will do? No. That was not going to happen.”
Kim began work almost immediately, quietly growing his nuclear arsenal.
"I think his legacy is in many ways a complete failure," Ankit Panda, Stanton senior fellow at Carnegie Endowment for International Peace said. "Kim Jong Un has basically had the opportunity over the last four years to continue manufacturing warheads.”
Leaving President Joe Biden with a heavily armed nuclear North Korea and very little leverage, analysts say.
Extinguishing hopes of a nuclear-free Korean Peninsula anytime soon.