Kim and Trump are set to meet on Tuesday at the Capella Hotel on Sentosa Island and Trump is expected to stay at the Shangri-La during his visit to Singapore.
But the hard truth of the matter is that Trump and Kim, by necessity, must talk about North Korea's human rights record.
"It's unknown territory in the truest sense, but I really feel confident", he said.
"Well Kim Jong Un is a cheat, hiding, lying - 100%", he explained. Glor will also lead Special Reports for coverage on the summit, and contribute to CBSN, CBS News' 24/7 streaming news service.
An Australian comedian known for impersonating North Korean leader Kim Jong Un said he was detained by Singapore's authorities on Friday and questioned about his political views, before being allowed into the country.
"I think President Trump signed onto this thinking that he was going to ride in on a white horse to Singapore, accept a bunch of nuclear warheads, and problem solved", Kristof says. "We're going to have to see what happens".
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"If I think it won't happen, I'm not going to waste my time". And if I think it won't happen, I'm not going to waste my time. "But I think it will take a little bit of time".
The arrival of the Air China Airbus 330 flight at Changi airport raised speculation that a delegation of North Korean officials joined an advance team headed by Kim's close aide, Kim Chang Son, who was in Singapore to prepare for the talks. He said he thinks "it's going to work out very well".
Taking this time frame into account, Japan will likely be tapped to play the "bad cop" until the "good cops" can complete the denuclearization process, said Tetsuo Kotani, a senior fellow at the Japan Institute of International Affairs. The president said at a press briefing in Quebec that his relationships with the other highly industrialized nations in the G-7 are all very strong despite disagreements over recent US tariffs.
Speaking on Thursday, Pompeo said that Kim had personally assured him that North Korea was ready to give up its nuclear arsenal.
Still, questions remain about what a deal on the North's nuclear weapons could look like. "And, by the way, we have worked very well with their people", he said.
"If it's hard for the USA ... to continue pushing 'maximum pressure, ' " Kotani said of Trump's campaign of sanctions and diplomacy meant to bring the North to the negotiating table, "then Japan should continue to verify the commitment of the worldwide community on behalf of Washington". "You don't know. This has not been done before at this level".
The minimum he hoped to achieve, Trump said, would be a "relationship, you start a dialogue, because as a deal person I've done very well with deals".