Past efforts to halt North Korea's nuclear buildup and to broker a peace deal for the divided Korean Peninsula are today considered monumental failures.
One promising moment came in 1994; another in 2005. But those hopes gradually fizzled out.
The next effort begins on Tuesday at a scenic Singaporean beach resort, in a first-ever meeting between a sitting US president and the North Korean leader.
Outcomes are uncertain, with high drama and shifting expectations from a president frequently bragging about his deal-making ability and a dictator for whom nuclear diplomacy makes strategic and economic sense.
Analysts see the mere fact that the summit will happen at all as a promising step forward in bringing the reclusive state closer to the world community. Just months ago, such a meeting seemed unthinkable.
"The worst case scenario is fighting an unnecessary war against North Korea that kills tens or hundreds of thousands of people," Evan Resnick, assistant professor at the S. Rajaratnam School of International Studies in Singapore, told Al Jazeera.
"Anything that's not that is a better outcome."
One can never be comfortable dealing with North Korea.
Greg Scarlatoiu, Committee for Human Rights in North Korea
Hardline North Korean critics remain sceptical about the hastily arranged meeting and unchartered venture into summit diplomacy.
"This is truly unprecedented," Greg Scarlatoiu, executive director of the Washington, DC-based Committee for Human Rights in North Korea, told Al Jazeera.
"That said, one can never be comfortable dealing with North Korea. The regime has breached each and every promise it has made through bilateral or multilateral diplomatic interaction."
Fire and fury
A constructive US-North Korea dialogue on denuclearisation follows a lengthy exchange of name-calling and taunts.
Last August, Trump threatened North Korea with "fire, fury and, frankly, power the likes of which this world has never seen before".
He repeated his military threat the following month while labelling Kim "Little Rocket Man ... on a suicide mission".
"The United States has great strength and patience, but if it is forced to defend itself or its allies, we will have no choice but to totally destroy North Korea," Trump told the United Nations.
Kim responded in kind: "Whatever Trump might have expected, he will face results beyond his expectation. I will surely and definitely tame the mentally deranged US dotard with fire," Kim said in a statement.
Those exchanges have since cooled, and earlier this year Kim broached the possibility of a face-to-face meeting with Trump.
It follows Kim's meetings with regional leaders earlier this year - he was photographed walking in the woods with South Korean President Moon Jae-in, and on a beach with Chinese President Xi Jinping.
Shifted rhetoric
Intelligence analysts have long said the North Korean leadership's priority is its survival and that Pyongyang has staked its existence on the development of nuclear weapons. In what may amount to a negotiating posture, the US has maintained its bottom line remains the complete, verifiable and irreversible denuclearisation of North Korea.
But the rhetoric has shifted, with Trump backing away in recent weeks from his pledge to put "maximum pressure" on Pyongyang.
North Korea cannot denuclearise completely right now and hope to be safe from a president who said we're going to rain fire and fury on you
Horacio Falcao
After meeting senior North Korean envoy Kim Yong-chol at the White House on June 1, Trump said: "We're not going to go in and sign something on June 12. And we never were. We're going to start a process. And I told him today, take your time. We can go fast. We can go slowly."
Analysts doubt that denuclearisation is achievable in the short term, and even with a political agreement, experts say the process could take up to 15 years.
"North Korea cannot denuclearise completely right now and hope to be safe from a president who said we're going to rain fire and fury on you, from a country that's been calling you evil for 25 years," said Horacio Falcao, a negotiations expert at the INSEAD graduate business school in Singapore.
Lee Seong-hyon, of the Department of Unification Strategy Studies at the Sejong Institute in Seoul, added: "Given the tremendous complexity involved with North Korea's nuclear weapons, it's not going to be a quick one-shot deal, simply because of the sheer complexity and details."
Bargaining incentives
For North Korea, incentives to the bargaining table include a peace treaty formally ending the 1950-53 Korean War, the ceasing of hostilities, security guarantees, the lifting of economic sanctions and large-scale foreign investment.
[Trump] is much more interested in the theatrics of public policy, rather than the substance
Evan Resnick
In political terms, the Trump-Kim exchange may simply come down to optics, with an overall messaging designed to boost both politicians with their respective home audiences: Trump promoting his image as a deal-maker, and Kim - who is believed to still be in his mid-30s - winning political legitimacy for himself and his country on the global arena.
"Trump is a publicity seeker. He sees the summit not as a means to an end, but the end itself. He's much more interested in the theatrics of public policy, rather than the substance," Resnick, the assistant professor, said.
He added, "Kim wants to attain some prestige on the international stage, and I don't see that as a bad thing. The less under siege North Korea perceives itself to be, the less belligerent it will be on the world stage."