Kim Jong Un and Donald Trump meet on Tuesday for an unprecedented summit in an attempt to address the last festering legacy of the Cold War, with the US President calling it a "one time shot" at peace.
Bringing the Korean War to a formal end 65 years after hostilities ceased will also be on the table at the first-ever summit between a North Korean leader and a sitting president of its "imperialist enemy".
The meeting in Singapore is the climax of the astonishing flurry of diplomacy on and around the Korean peninsula this year, but critics charge that it risks being largely a triumph of style over substance.
Washington is demanding the complete, verifiable and irreversible denuclearisation (CVID) of the North, while Pyongyang has so far only made public pledges of its commitment to the denuclearisation of the peninsula -- a term open to wide interpretation -- while seeking security guarantees.
"The success will be in the shutter clicks of the cameras," he said. "They both get what they want." Trump insisted last week that the summit would "not be just a photo op", saying it would help forge a "good relationship" that would lead to a "process" towards the "ultimate making of a deal".
But as he embarked for Singapore he changed his tune, calling it a "one-time shot" and adding he will know "within the first minute" whether an agreement will be possible.
"If I think it won't happen, I'm not going to waste my time," he said.
But even the merit of the event itself -- long sought by the North, and which Trump apparently impulsively agreed to in March, reportedly without consulting his advisers -- has been called into question.
"People call it a historic summit but... it is important to understand that this summit was available to any US president who wanted to do it and the point is no US president wanted to do this, and for good reasons," said Christopher Hill, a former lead US nuclear negotiator with North Korea.
The two countries have been at loggerheads for decades.
The North invaded the South in 1950 and the ensuing war saw the US-led UN troops backing Seoul fight their way to a stalemate against Pyongyang's forces which were aided by Russia and China, before the conflict ended in stalemate and an armistice which sealed the division of the peninsula.
Sporadic provocations by the North have continued while Pyongyang has made increasing advances in its nuclear arsenal, which it says it needs to defend against the risk of a US invasion.
Last year it carried out by far its most powerful nuclear test to date and launched missiles capable of reaching the US mainland, sending tensions soaring to a level unseen in years as a newly-elected Trump traded threats of war and colourful personal insults with Kim, with Trump dubbed a "dotard" and Kim "Little Rocket Man".
Kim has met twice with both Moon and Xi Jinping, the president of China, long the North's most important ally.
But Trump -- for whom a major accomplishment would bolster his position ahead of midterm elections in November -- baffled observers when he said he did not think he had to prepare "very much" for the summit.
"It's about attitude," Trump said. "So this isn't a question of preparation.
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