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Now, the third generation leader of the reclusive state appears to have spruced up his international image in a matter of months as he takes leisurely strolls with world leaders and engages in bear hugs. He even has a sense of humor.
"Kim Jong Un is presenting a much more accessible face of the regime to the world, and he's actually been quite clever, I think, in the way he's managed the international image," said Simon Baptist, regional director for Asia at The Economist Intelligence Unit.
That is particularly shrewd as "he has murdered his relative at an international airport, and millions of North Koreans do live in impoverishment, or in prison camps," Baptist told CNBC.
Belying years of international isolation, Kim appeared at ease this week as he interacted with Singaporean government officials including Prime Minister Lee Hsien Loong.
In videos of his nocturnal jaunt, Kim smiled and waved to cheering crowds, a spectacle replicated elsewhere in Singapore as disbelieving onlookers gather to gawk at the reclusive leader — or rather, his motorcade — on his rare trip overseas.
Kim even posed for selfies with Singaporean ministers accompanying him. The photos uploaded on social media went viral.
"He's certainly managed to present a very different face globally," Baptist said.
Kim's laidback stance in Singapore followed similar displays elsewhere recently.
When International Olympic Committee President Thomas Bach visited Pyongyang in March, the rotund North Korean leader told the German: "Even if it may not look like it, I love to play sport, and especially basketball," The Wall Street Journal reported, citing Bach.
When Kim met South Korean President Moon Jae-in in April, Kim joked that North Korea's early morning missile launches had likely awakened Moon numerous times, and promised not to do that anymore, Reuters reported, citing officials.
Despite the bonhomie, there is skepticism that North Korea is shifting strategically — if history is anything to go by.
"In 2000, Kim Jong Un's father did exactly the same thing. He came out of his anti-social character, his shell dramatically, called for an inter-Korean summit in June, and a fortnight before his meeting with the South Korean president, he made his very trip to China as the national leader six years after inheriting power — just as Kim Jong Un did this March, " said Sung-Yoon Lee, Tufts Fletcher School and Alexandra Bell of the Center for Arms Control and Non-Proliferation, on CNBC's "Power Lunch."
But, little changed.
"So Kim Jong Un by doing this, by putting on this elaborate show through a period of provocation that he's a new man, he's a legitimate global statesman with whom the U.S. can engage and do nuclear business, not only does he affect a dramatic image makeover but, more importantly, Kim is able to buy time and money to do what he really wants to do, which is to further advance his nuclear and missile, his menacing capabilities," said Lee.
Kim is probably turning to diplomacy now just for sanctions relief and economic concessions, said Paul Haenle, director of the Carnegie-Tsinghua Center at Tsinghua University in Beijing.
"There may be a glimmer of hope that [Kim's] decided to make a strategic shift, but I haven't seen a lot of indications that that is the case and I tend to think that Kim Jong Un probably sees the development of his nuclear program as what has gotten him to the table with President Trump," said Haenle, who is also former U.S. representative to the six-party talks.