It is immensely flattering for Kim Jong-un, the leader of North Korea – a small, impoverished and isolated country – to take part in a one-to-one summit with the president of the United States.
Traditionally, history-making summits have been held between the leaders of great powers and dealt with matters of war and peace. During the 20th century, several changed the course of history. And each holds their own lessons.
The summit between Adolf Hitler of Germany, Neville Chamberlain of the UK, Benito Mussolini of Italy and Édouard Daladier of France has become notorious in the history books as marking the high point of the failed policy of appeasement of Nazism.
Chamberlain traded away Czech territory in return for assurances of future peace that turned out to be valueless. To this day, “Munich” has become shorthand for short-sighted weakness.
But, at the time, Munich was regarded as a triumph by many in the UK. Chamberlain was greeted with cheering crowds in London, and even in Munich before his departure.
Lesson: History's verdict may be very different from the verdict the day after the summit. Remember that, if Donald Trump emerges from the summit proclaiming that peace is breaking out on the Korean peninsula.
The Yalta summit, held in Crimea, between Joseph Stalin of the Soviet Union, US president Franklin Roosevelt and British prime minister Winston Churchill was a crucial moment in the making of the post-second World War order.
In an effort to keep the anti-Nazi alliance together, and to persuade Moscow to enter the war against Japan, an ailing Roosevelt agreed to Soviet demands to keep hold of the Polish territory that the USSR had annexed in 1939.
Some historians argue that Roosevelt had little option at this stage in the war. Churchill favourably compared the summit to Munich: “Poor Neville Chamberlain believed he could trust Hitler . . . But I don’t think I’m wrong about Stalin.”
However, to this day, many in Poland and elsewhere regard Yalta as a synonym for betrayal.
Lesson: If you are not at the negotiating table, you should be worried that your interests might be traded away. This is something that the Japanese government will be particularly concerned about, as Trump and Kim prepare to meet.
Richard Nixon's meeting with Mao Zedong was one of the most dramatic moments of the cold war, marking the beginning of the end of decades of US-Chinese antagonism.
The summit happened after many months of secret diplomacy, involving US secretary of state Henry Kissinger and Zhou Enlai, the Chinese premier. It was a sign that the Communist bloc was not monolithic and that the interests of Moscow and Beijing had begun to diverge.
Nixon called his visit to China "the week that changed the world". The immediate results of the summit were fairly minor.
By 1974, Nixon was out office and, by 1976, Mao was dead. But the road to the full restoration of relations between the US and China began here.
Lesson: Sometimes the meeting is the message. Much as with Trump and Kim, the pictures of historic adversaries shaking hands went around the world.
This summit between the leaders of the US and the USSR took place against a background of both fear and anticipation.
The US military build-up during Ronald Reagan’s presidency and the USSR’s fierce reaction had led to heightened fears of nuclear war.
But it was also clear that Mikhail Gorbachev was a new kind of Soviet leader, more open to the West and prepared to take risks.
The Reykjavik meeting illustrated that summits between two leaders can branch off in unexpected directions if the personal chemistry is right. At one point, the two leaders agreed on the breathtaking goal of the “elimination of all nuclear weapons within 10 years”.
To the relief of many of their senior officials, they were unable to sign off on the deal because of remaining disputes about the Reagan administration’s push for the Strategic Defence Initiative, a missile-based system nicknamed “Star Wars” at the time.
In public, Gorbachev spun the summit as a "breakthrough". In private, he was dismayed. His biographer, William Taubman, records that two days after Reykjavik, Gorbachev told the politburo that Reagan was "extraordinarily primitive, troglodyte and intellectually feeble."
Lesson: Once two leaders are locked together in a negotiating room, unexpected things can happen.
The chances that something unpredictable will happen at the Sentosa summit are heightened by the extreme lack of preparation in the Trump White House.
Even Reagan, who had a reputation for intellectual laziness, submitted to many hours of briefings at the White House before the Reykjavik summit.
By contrast, just days before the Singapore summit, the Trump administration had not convened a single meeting of cabinet-level officials to prepare the president for his meeting with Kim Jong-un. – Copyright The Financial Times Limited 2018