The Unconventional Diplomacy Between Donald Trump and Kim Jong Un

Donald Trump recently reiterated his assertion of maintaining a good relationship with North Korean leader Kim Jong Un. Photographs from their past interactions highlight one of the most unusual diplomatic relationships in recent history. Over the weekend, Trump shared several social media posts mentioning Kim. In one post, he included a photograph from their 2019 meeting at the Korean Demilitarized Zone, commenting, “Despite the unfriendly look in this particular picture, there are many where we’re smiling. Kim Jong Un and I get along GREAT!” In another post, Trump stated that his “very good relationship” with Kim was a reason he opposed extensive joint military exercises involving the United States and South Korea.

These posts brought back memories of a diplomatic connection that achieved several historic milestones. Between 2018 and 2019, Trump and Kim met three times, marking the first summit between a sitting U.S. president and a North Korean leader and the first visit by a sitting American president to North Korean territory.

Singapore Summit, June 2018

In 2018, Trump and Kim were part of an event considered almost unthinkable: the first summit between a sitting U.S. president and a North Korean leader. The encounter received global attention and was heralded by both nations as the start of a new era in relations between Washington and Pyongyang. Their meeting at the Capella Resort in Singapore on June 12, 2018, involved several hours of talks. The leaders signed a joint statement committing to develop new relations and pursue the denuclearization of the Korean Peninsula. The images from Singapore remain iconic, showing Trump and Kim sharing smiles and camaraderie, characterizing their personal rapport.

Hanoi Summit, February 2019

Following the perceived goodwill from Singapore, expectations were high as both nations sought progress on North Korea’s nuclear weapons program and the sanctions imposed on Pyongyang. Unlike Singapore, the Hanoi meeting ended without an agreement. Negotiators failed to reconcile differences over the extent of sanctions relief and the denuclearization steps Washington expected from North Korea. The summit concluded earlier than planned, and a signing ceremony that had been highly anticipated did not occur. Nevertheless, the images from Hanoi continued to reflect a cordial relationship between the leaders.

Demilitarized Zone, June 2019

In June 2019, Trump and Kim met at the Korean Demilitarized Zone, the heavily fortified border between North and South Korea. During this encounter, Trump crossed the military demarcation line into North Korea, becoming the first sitting U.S. president to enter the country. This moment generated images that quickly spread worldwide and symbolized Trump’s North Korea diplomacy. The meeting underscored Trump’s claim that his personal rapport with Kim helped mitigate tensions, even as broader negotiations stalled.

Attention on a Unique Relationship

The diplomatic efforts initiated in Singapore ultimately did not achieve the denuclearization breakthrough negotiators sought, causing formal talks to stall. Yet the images from these encounters continue to capture attention because they document a series of unprecedented events. They include the first summit between U.S. and North Korean leaders, a sitting American president meeting a North Korean ruler, and a sitting U.S. president stepping into North Korean territory.

For more information, reach out to Newsweek editors Rebecca Flood and Emma Lee-Sang regarding this story.