The jet carrying Kim landed at the airport Sunday afternoon amid huge security precautions on this city-state island. Singapore quickly released a picture of Kim and the foreign minister shaking hands.
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A large limousine with a North Korean flag could then be seen surrounded by other black vehicles with tinted window as it sped through the city's streets to the St. Regis Hotel, where China's President Xi Jinping once stayed.
Kim's summit with Trump has captured intense global attention after a turn to diplomacy in recent months replaced, for the time being, serious fears of war last year amid North Korean nuclear and missile tests.
The North, many experts believe, stands on the brink of being able to target the entire U.S. mainland with its nuclear-armed missiles, and while there's deep skepticism that Kim will quickly give up those hard-won nukes, there's also some hope that diplomacy can replace the animosity between the U.S. and the North.
The North Korean autocrat's every move will be followed by 3,000 journalists up until he shakes hands with Trump.
Kim has only publicly left his country three times since taking power after his despot father's death in late 2011 - twice traveling to China and once across his shared border with the South to the southern part of the Demilitarized Zone in recent summits with the leaders of China and South Korea respectively.
Despite the high stakes of a meeting meant to rid North Korea of its nuclear weapons, the talks have been portrayed by Trump in recent days more as a get-to-know-you session.
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He has also raised the possibility of further summits and an agreement ending the Korea War by replacing the armistice signed in 1953 with a peace treaty. China and South Korea would have to sign off on any legal treaty.
There's a flurry of speculation about what results might come from the summit.
The initial goal was the "complete denuclearization" of the North. Pyongyang has said it's willing to deal away its entire nuclear arsenal if the United States provides it with a reliable security assurance and other benefits.
But many, if not all analysts, say that this is highly unlikely, given how hard it has been for Kim to build his program and that the weapons are seen as the major guarantee to his unchecked power.
Any nuclear deal will hinge on North Korea's willingness to allow unfettered outside inspections of the country's warheads and radioactive materials, much of which is likely kept in a vast complex of underground facilities. Past nuclear deals have crumbled over North Korea's reluctance to open its doors to outsiders.
Another possibility from the summit is a deal to end the Korean War, which North Korea has long demanded, presumably, in part, to get U.S. troops off the Korean Peninsula and, eventually, pave the way for a North Korean-led unified Korea.
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The fighting ended on July 27, 1953, but the war technically continues today because instead of a difficult-to-negotiate peace treaty, military officers for the U.S.-led United Nations, North Korea and China signed an armistice that halted the fighting.
The North may see a treaty - and its presumed safety assurances from Washington - as its best way of preserving the Kim family dynasty.
The ensuing recognition as a "normal country" could then allow sanctions relief, and later international aid and investment.
Kim may also be interested in getting aid and eventual investment to stabilize and then rebuild a crumbling economy. Just meeting with Trump will also give Kim recognition as the leader of a "normal" country and as an equal of the U.S. leader.
(Copyright 2018 The Associated Press. All rights reserved.)