He will rack up another one here Tuesday, when he becomes the first North Korean leader to meet with a sitting U.S. president. It will be the most important day to date of his expectation-defying reign.
"This is an epic-making moment," said Ken Gause, an expert on North Korea's leadership at CNA, a research group based in Virginia. "Even if this is just a meet-and-greet, it's going to be a huge event simply because the president of the United States and the head of North Korea actually sat at the same table."
Both leaders have a penchant for making bold decisions and a love of the limelight. Yet both want this meeting to be more than just a photo op.
For President Donald Trump, it offers an opportunity to prove his self-described masterful negotiating skills and score a diplomatic victory after a year of "maximum pressure" on North Korea.
As for Kim, his objectives are clear - and eminently relatable for the American president.
"Kim Jong Un wants to make North Korea great again," said Kim Il-guk, who raised money for the regime before escaping from the North in 2014. "He wants to get rid of the international sanctions so North Korea can make more money and become a great country."
When Kim Jong Un succeeded his father more than six years ago, he inherited a totalitarian state known mainly for its brutal repression, widespread malnutrition and bellicose propaganda department.
Kim, then just 27, had no leadership qualifications other than being born into the cult established by his grandfather after World War II with the backing of China and the Soviet Union. Many analysts, in Washington and Seoul, thought North Korea's days were numbered.
But Kim has not just survived - he has arguably thrived. He has presided over astonishing advances in nuclear and missile technology and had potential rivals for power killed, including his uncle and his half brother. And this year, he has embarked on a charm offensive that has global leaders - from China, South Korea, Japan, Syria and Russia - seeking to meet him.
But Tuesday brings the jackpot: a meeting with the head of the world's No. 1 superpower that will legitimize Kim as a leader - an equal, even - in a way that eluded both his predecessors.
"This unprecedented meeting with the U.S. president will make Kim Jong Un feel very proud, having achieved something his father and grandfather didn't," said Joo Seong-ha, who escaped from North Korea and now writes about the country for South Korea's Dong-A Ilbo newspaper.
And although "maximum pressure" may have helped bring Kim to the negotiating table, the other reality is that he is coming to the summit from a position of relative strength, said Kenneth Dekleva, a former State Department diplomat and psychiatrist who has profiled leaders including Slobodan Milosevic and Vladimir Putin, as well as the two most recent North Korean leaders.
"Kim is strong, confident and very well-prepared - including the technical details of denuclearization - for the upcoming summit. He has in effect staked his reputation on having a successful summit," Dekleva said.
It would be "folly" to look at Kim's relative youth and inexperience and underestimate him, he said, noting that Trump himself once memorably called Kim a "smart cookie."
The North Korean leader is following a plan he laid out early in his tenure.
In 2013, he announced a "dual-track" policy to advance both the nuclear program and the economy, a shift from the "military first" approach of his father.
To prove his military chops, he first focused on the nuclear program, pouring his country's meager resources into building increasingly long-range missiles and what is widely acknowledged to be a hydrogen bomb.
After a year of alarming tests, Kim announced in November that his weapons program was complete. That was the signal he was ready to turn to the economy.
And so he did.
The goal: to boost the economy by getting rid of the international sanctions imposed as punishment for last year's provocations, or at least getting Beijing to stop implementing them. About 90 percent of North Korea's trade goes to or through China.
"This is his top priority," Kim Seok-hyang, professor of North Korean studies at Ewha Womans University in Seoul, said of Kim's focus on the economy. "In 2012, Kim Jong Un promised his people that they would never be hungry again. But he has not been so successful at that so far."
Malnutrition remains chronic, with the World Food Program estimating that 40 percent of the population is undernourished. But Kim's pledge to end hunger is not about caring for his people. In the tradition of his dynasty, he has shown blind disregard for North Koreans' well-being, channeling money into the nuclear weapons program rather than providing medicine for hospitals, books for schools or electricity for homes.
For Kim, this appears to be an existential issue. He is now ready to take care of his people solely because he wants to take care of himself. Like his father and grandfather before him, he wants to die a natural death in office.
His father, Kim Jong Il, was 53 when he took control of North Korea, so all he really had to do was to hold on for 20 or so years (he lasted 17.) He didn't need to change anything, said Andrei Lankov, a Russian historian who studied at Kim Il Sung University in Pyongyang and periodically visits North Korea.
But Kim Jong Un was 27 when he was bequeathed the country. Now 34, he could have as many as 50 years in power ahead of him. Kim Il Sung lived to 82.
"He can't afford to do nothing," said Lankov. "For that reason, he is trying to revive the economy. He wants to keep people's stomachs full of food and their hearts full of fear."
While much of the North Korean economy remains stuck in the Soviet era, theoretically shaped by communist central planning, there have been notable improvements thanks to the emergence, and tolerance, of private-sector market activity.
Surveys show that the vast majority of citizens now earn a living through their own business projects, whether it be offering perms from their front rooms or smuggling coal or movies across the border with China.
The regime has allowed this burgeoning market activity, apparently recognizing that it helps head off resentment over the state's inability to provide. It has had the added benefit of making North Koreans feel that their living standards are improving.
Kim Jong Un has endeavored to show that North Korea is becoming a modern country through showcase projects concentrated in the capital, including high-rise apartment towers, amusement parks and sushi restaurants.
But that doesn't mean he's about to embark on Chinese- or Vietnamese-style reforms that could loosen his grip on the regime. Instead, he wants "reforms without openness," Lankov said.
"He wants to reduce the gap with North Korea's neighbors so that people will give him a chance to stay in power," he said. "Chances are not high that he will die a natural death at age 75, but he needs to try. For a young person, it makes sense to take this risk."
Gause of CNA also thinks that Kim is playing a long game. While Kim Jong Il tended to think tactically and maneuver for short-term gains, his son has to think in longer strategic moves.
"He is a young leader who has no inherent legitimacy," Gause said. Kim Jong Un's grandfather was the leader of the North Korean revolution, and his father spent 20 years building a myth and patronage network. Kim Jong Un had little of that.
"If he can tell North Koreans that he brought the American president to the negotiating table," Gause said, "his legitimacy is going to go off the charts."
(This story has not been edited by NDTV staff and is auto-generated from a syndicated feed.)