Many experts on North Korea, one of the most insular and unpredictable countries in the world, remain sceptical Kim will ever completely abandon nuclear weapons. "We're not going to go in and sign something on June 12, and we never were".
"I am on my way to Singapore where we have a chance to achieve a truly wonderful result for North Korea and the World". And based on the tweets that Trump sent Monday morning, it doesn't seem like he left his baggage from the first summit at the door.
Kim's full delegation has not yet been confirmed, but other prominent North Korean officials seen in photos included foreign minister Ri Yong Ho and Kim Chang Son - the man who has been in Singapore in recent weeks negotiating logistical details for the summit.
Trump and Kim are staying in separate hotels in the famous Orchard Road area of Singapore, dotted with high-rise luxury apartment blocks, offices and glittering shopping malls.
The crowd murmured. It was waiting to get a glimpse of one of the world's most villainous dictators, North Korea's Kim Jong Un. Funds for military activities are obtained from remittances that come from the forced labor of North Koreans sent overseas, as well as forced labor domestically.
"The circus-like atmosphere might be amusing if the stakes weren't so high", wrote USA campaigning group Human Rights Watch.
President Donald Trump blowing out a candle on his birthday cake.
Top members of Trump's administration have said that the North Koreans wouldn't receive any benefits before taking steps to denuclearize - wary of falling into the same predicament that doomed previous agreements with the rogue regime. Earlier in the day, he had lunch with Singapore's President Lee Hsien Loong and was presented with a cake ahead of his birthday on Thursday.More news: E3 2018: Cyberpunk 2077 Pre-Order Guide
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He is one of the few westerners to have met the North Korean leader on visits to the capital city Pyongyang.
Kim's summit with Trump has captured intense global attention after a turn to diplomacy in recent months after serious fears of war past year amid North Korean nuclear and missile tests.
He predicted that he will know "within the first minute" if the Singapore summit, which has been under threat of cancellation, is a success.
But North Korea now deems itself "a nuclear state", and insists the USA must end its "nuclear threats and blackmail" as a precondition for denuclearization, according to a statement last month from First Vice Minister of Foreign Affairs Kim Kye Gwan.
"Ms Choe has also served as an English language interpreter for Kim Jong-un and other senior DPRK leadership when they have interacted with foreign nationals", the website states. An editorial in the Rodong Sinmun news outlet also talked about a "new relationship" with the US.
Reunification, he said, would be impossible because four powers - the US, China, Russia and Japan - do not want to see a unified Korea.
Yet Trump and Kim have yet to agree even on how to define denuclearization of the Korean peninsula - the stated goal of the meeting.