Although President Donald Trump often criticizes his predecessors for failing to resolve the nuclear stalemate on the Korean peninsula, he seems largely indifferent to history and its lessons.

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WASHINGTON — In his 1961 inaugural address, President John Kennedy spoke about the possibility of daring diplomacy to thaw even the coldest of relationships: “Let us never negotiate out of fear. But let us never fear to negotiate.”

Those words, often cited by President Barack Obama, could also be repurposed by President Donald Trump — if the 45th president were into quotations — as he embarks on the highest-stakes U.S. summit in a generation, sitting down in Singapore on Tuesday with Korean dictator Kim Jong Un.

But Kennedy’s most consequential summit, which came just months into his presidency, was an unmitigated disaster, according to historians.

Despite careful preparation, the young president did not heed the warnings of advisers familiar with his Soviet counterpart, Nikita Khrushchev, whom he met in Vienna in June 1961. Kennedy’s attempts to establish a friendly rapport, which experts had cautioned him against, came across as weakness.

After the summit, he knew immediately he’d blown it, as did William Lloyd Stearman, a national-security aide who traveled with Kennedy to Vienna.

“It was Al Capone meets Little Boy Blue,” Stearman said this past week. Many historians say that first impression fueled Khrushchev’s later confrontations with Kennedy: the Berlin Wall’s construction later in 1961 and the Cuban missile crisis in 1962.

Their understanding of that and other consequential summits, like President Richard Nixon’s 1972 trip to China and the meeting between President Ronald Reagan and Russia’s Mikhail Gorbachev in 1986, especially worries them about grave risks of Trump’s brash, media-centric diplomacy as he comes face to face with Kim.

“Nixon was very quiet personally in these situations, more careful and more shy,” said Julian Zelizer, a historian at Princeton University. “Trump’s the opposite: He’s more explosive and liable to say anything.”

Like Nixon, who went to China without knowing if Mao Zedong would greet him, Trump is accepting some political risk in meeting with Kim, who is unlikely to scrap the nuclear program that brought the United States to the negotiating table without securing major concessions — a much heavier lift than Nixon had in 1972.

“Nixon had no preconditions going in, and both countries came out of that summit with nothing other than the understanding that they needed to talk and coexist,” said Timothy Naftali, a presidential historian at New York University. “The (1972) summit’s achievement is just in the fact that it happened.”

Trump is heading into the Singapore summit with his characteristic nonchalance, saying that his lack of traditional preparation — National Security Council meetings, of which there have been none, thick briefing books and hours of Situation Room strategizing — will be more than offset by his instincts and “attitude.”

“This is a neophyte who has given every indication that he does not like to do his homework, and the cost could end up being very great,” said presidential historian Michael Beschloss. “We’ve never seen a president who wears as such a badge of honor that he won’t prepare. There’s no president in American history that has done that, and certainly not on a summit as important as this.”

Trump, who has toggled between unbridled optimism with effusive praise for Kim and bluster that he may abruptly walk out of their meeting if it goes poorly, has only recently engaged in setting more modest expectations for the summit, saying that this meeting could be just the beginning of a continuing dialogue.

“I’m not sure if he’ll recognize that a good, constructive meeting can be a victory in itself,” Naftali continued. “If he’s not careful, he could paint himself into a corner, seeking an achievement he can’t actually get. That’s what Kennedy did with Khrushchev.”

Like the Singapore summit, Reagan’s 1986 summit with Gorbachev in Reykjavik, Iceland, was hastily arranged in response to Gorbachev’s sudden willingness to ban all ballistic missiles. Reagan engaged in remarkably free-form negotiations and nearly came to a far-reaching agreement. But Reagan ultimately balked, unwilling to give up his “Star Wars” missile-defense program.

What at the time appeared to be a diplomatic failure is now seen as a success, as the talks allowed both countries to realize their shared desire to avoid a war and better understand the concessions each was willing to make. The next year, the United States and Soviet Union agreed on an arms reduction treaty. Now, historians view the meeting in Reykjavik as the beginning of the end of the Cold War and the Soviet Union itself.

“Reagan’s command of detail was not great, but we know now that he had actually been studying these issues for decades,” Beschloss said. “He had a very specific idea of how the Cold War would end. This was not a neophyte stumbling into the room.”

The Singapore summit will be different. It is the first major summit to occur in the social-media era and the first involving two leaders as unpredictable and untested as Trump and Kim.

For the past year, Twitter has enabled Trump and Kim to speak to each other directly without the filters of experts and aides — and that dialogue has taken a number of twists and turns. But it has also led to Singapore and a summit that historians, for all their concerns, are hoping will yield something positive. Although forming a clear-eyed and lasting assessment of its success or failure could take years, there is a possibility for success.

“Experts on diplomacy scoff at this, but the proof of whether a summit is successful or not is the result,” Farrell said.

Although Trump often criticizes his predecessors for failing to resolve the nuclear stalemate on the Korean Peninsula, he seems largely indifferent to history and its lessons.

Here’s how other presidential meetings and summits have played out:

Hoover confers with Hitler

Five years after his presidency, Herbert Hoover toured Europe, mostly to pick up awards for his can-do humanitarian effort to feed the war-ravaged continent in the 1920s. In Berlin, Hoover had a 40-minute chat with Adolf Hitler at the Reich Chancellery in March 1938, then dined with Nazi minister Hermann Göring at his hunting lodge. In his conversation with Hitler, Hoover spoke up for personal liberty. The Fuhrer replied that Germany, unlike resource-rich America, could not afford such liberties.

Back home, Hoover denounced the Nazis’ “disregard for both life and justice,” but he argued the United States should stay out of European conflicts with Germany. He thought Hitler posed a bigger threat to Josef Stalin’s Soviet Union than the West.

Roosevelt’s wartime meetings with Stalin

Franklin Roosevelt and Winston Churchill met twice with Soviet dictator Josef Stalin during World War II, to coordinate the fight against Germany. In Tehran in 1943, Roosevelt and Churchill agreed to open up a second front in Western Europe against Germany, while Stalin agreed to launch an offensive in Eastern Europe to divide Germany’s resources. Roosevelt, who had granted diplomatic recognition to the Soviet Union in 1933, thought he had won Stalin’s confidence with the promise. But Stalin also pressed for concessions about the borders and governments of postwar Poland and the Baltic states.

Eastern Europe’s fate was a key subject when the wary Allies met again at Yalta in March 1945. Inside the Soviet Crimean seaside resort’s primitive, bedbug-ridden palaces, and between Stalin’s many long vodka-fueled toasts, Roosevelt and Churchill made concessions to Stalin about Poland’s provisional government and borders. They extracted a promise of free elections in Eastern Europe, which Stalin disregarded as soon as he could.

Reagan fetes the ruthless Suharto

Indonesia’s ruthless general and president, Suharto, oversaw a massacre of 500,000 leftists as he seized power in the mid-1960s. His 1975 invasion and annexation of East Timor left 200,000 dead. Yet U.S. presidents from Lyndon Johnson to Gerald Ford backed Suharto as an anti-Communist force in Southeast Asia.

Reagan kept up the U.S. support, even welcoming Suharto and his wife with a White House state dinner in October 1982. First lady Nancy Reagan wore “a black and white satin dinner gown by Bill Blass,” The Washington Post reported. “President Suharto waved goodbye, his diamond ring flashing in the night.” Four years later, Suharto returned the favor, hosting the Reagans in Bali during a meeting of the Association of Southeast Asian Nations.

Bush smooches with Crown Prince Abdullah

Yes, this really happened. The two leaders were also photographed holding hands at George W. Bush’s ranch in Crawford, Texas, in 2005.

Keep in mind that 15 of the 19 hijackers on Sept. 11, 2001, were Saudis. So was the man who ordered the attack: Osama bin Laden. The oil-rich kingdom was then — and remains now — one of the most repressive and religiously intolerant regimes in the world.

Clinton refuses to grip-and-grin with Kim Jong Il

Bill Clinton isn’t smiling in the official photograph from his 2009 trip to North Korea. He warned his aides not to smile, too. He was all business, officially there as a private citizen (though his wife was secretary of state) to negotiate the release of two American journalists held hostage by the government of Kim Jong Il, the current North Korean leader’s father. “We were told that we were going to a meeting,” recalled journalist Laura Ling after flying home with the ex-president. “When we walked through the doors, we saw standing before us President Bill Clinton.”

Obama swallows his idealism with Mubarak

For Obama, welcoming Egyptian President Hosni Mubarak to the White House represented a compromise of his foreign-policy idealism. Since 1981, Mubarak had ruled Egypt as a military dictator, with broad arrest powers and a record of police-state torture. The agenda for Mubarak’s August 2009 White House visit was an ever-elusive peace between Israel and the Palestinians, a classic example of presidential practicality in dealing with an oppressive ally.

The two men met again in 2010. But Obama reversed course in 2011 amid Egypt’s Arab Spring protests, declaring that a transfer of power from Mubarak “must begin now.” That helped nudge Mubarak out of power, though critics say it led other U.S. allies to doubt American loyalty.

Trump embraces Putin

Even after the appointment of a special counsel to investigate Russian interference in the 2016 presidential election, Trump spent much of July 2017’s Group of 20 summit in Hamburg getting to know Russian President Vladimir Putin better. The two leaders stretched a scheduled half-hour meeting into two hours, then had an unscheduled hourlong chat with only a Kremlin interpreter present.

“Trump’s best single relationship in the G-20 is with Putin,” said Ian Bremmer, a consultant who broke news of the second meeting in Vanity Fair. The friendly chat, after Trump’s praise of Putin’s authoritarian control of Russia, alarmed other summit-goers. “U.S. allies were surprised, flummoxed, disheartened,” Bremmer said. “You’ve got Trump in the room with all these allies and who is the one he spends time with?”