"This is just a new beginning", said Trump while he was shaking hands with Kim.
Wearing a Make America Great Again baseball cap and a T-shirt bearing the name of his sponsor Potcoin, Rodman sobbed as he described his feelings about the summit and recalled the abuse he had received over his controversial visits to Pyongyang to meet Kim. There was a past that grabbed our ankles and wrong prejudices and practices that at times covered our eyes and ears.
Kim was heard telling Trump through a translator: "I think the entire world is watching this moment".
But other reports said it was Kim who made a decision to leave early, even though Trump was willing to stick around.
Kim is due to leave on Tuesday afternoon, a source has said. "We will all know soon whether or not a real deal, unlike those of the past, can happen!" he wrote.
Employees at a foreign exchange trading company in Tokyo watch the meeting.
Rodman claimed that several officials, including former President Barack Obama, brushed him off and did not take his trips to North Korea seriously: "Obama didn't even give me the time of day", Rodman said.
The president planned to stop in Guam and Hawaii on the way back to Washington. Trump then directed Kim to walk down a hallway, where they briefly spoke.
As for where Kim will spend the night, he's opted for the St. Regis Singapore, where it is believed he has checked into the hotel's $11,500-a-night Presidential Suite.
Critics of Trump, however, were quick to point out that the US president had given legitimacy to a murderous regime responsible for the starvation and death of tens of millions of people.
The summit won't be Trump's first foray into treating an established despot and human rights abuser like or perhaps better than the leader of an allied nation, though it is Twitter's first time treating such an event like a Game of Thrones season finale.
It's not clear what the U.S. side has been able to extract from the North Koreans in terms of their willingness to get rid of their nuclear weapons or allow inspectors into the country to catalogue the scale of their program. Or, it could amount to little more than a much-photographed handshake.
White House press secretary Sarah Huckabee Sanders said Sung Kim, the United States ambassador to the Philippines who has taken the lead on policy negotiations with the North, will hold a "working group" with a North Korean delegation to discuss final preparations for the meeting.
As Trump sought to build a bridge with Kim, he was smashing longtime alliances with Western allies with his abrasive performance at the G-7 and angry tweets directed at Trudeau and sent from aboard Air Force One as Trump flew from Quebec to Singapore.
Kim referred to the decades of hostility that preceded the landmark meeting. Before the announcement, U.S. Secretary of State Mike Pompeo seemed to hint that the outcome of the talks might not be what Trump has promised in the past.
But when pressed by reporters, the secretary of state would not say whether or not that could include reduction of the number of or removal of US troops in South Korea.
Rodman said he believed Trump "will understand that the people of North Korea have a heart, have a soul, charisma and love each other".
Another challenge is monitoring North Korea's nuclear scientists.
And until denuclearisation takes place, sanctions against North Korea would remain in place, he stressed.
It is the first time a sitting USA president has ever met a North Korean leader.
It's unclear what Trump and Kim might decide Tuesday. "I knew things was going to change". "That's what I do".