As Donald Trump renewed claims that he and North Korean leader Kim Jong Un have a good relationship, photographs offer a look back at one of the most unusual diplomatic relationships in modern history.

Over the weekend, Trump shared multiple social media posts referencing Kim. In one, he posted a photograph from their 2019 meeting at the Korean Demilitarized Zone and wrote: “Despite the unfriendly look on this particular picture, there are many where we’re smiling, Kim Jong Un and I get along GREAT!”

In another, Trump said his “very good relationship” with the North Korean leader was one reason he opposed large-scale joint military exercises involving the United States and South Korea.

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The posts revived memories of a diplomatic relationship that produced a series of historic firsts. Between 2018 and 2019, Trump and Kim met three times, including 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.

Here is a look at Trump’s relationship with Kim through the photographs that defined it.

Singapore Summit, June 2018

It was in 2018 that Trump and Kim were at the center of a moment that was considered almost unimaginable: the first ever summit between a sitting U.S. president and a North Korean leader.

The encounter was closely watched around the world and was presented by both sides as the beginning of a new chapter in relations between Washington and Pyongyang.

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Meeting at the Capella Resort in Singapore on June 12, 2018, it involved several hours of talks before the two leaders signed a joint statement committing to work toward new relations and the denuclearization of the Korean Peninsula.

The images from Singapore remain among the defining photographs of Trump’s first presidency, showing the U.S. president walking alongside Kim, smiling for cameras and presenting a display of personal rapport that would become a hallmark of their interactions.

Hanoi Summit, February 2019

Expectations were high following the apparent goodwill generated in Singapore. Both sides entered the talks seeking progress on the central issue of North Korea’s nuclear weapons program and the sanctions imposed on Pyongyang.

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But unlike the summit in Singapore, the Hanoi meeting between Trump and Kim ended without an agreement. Negotiators were unable to bridge differences over the extent of sanctions relief North Korea wanted and the steps Washington expected in return on denuclearization. The summit concluded earlier than planned, and a signing ceremony that many observers had anticipated never took place. Even so, the images from Hanoi still projected a cordial relationship between the two leaders.

Demilitarized Zone, June 2019

In June 2019, Trump and Kim met in the Korean Demilitarized Zone, the heavily fortified border separating North and South Korea. During the encounter, Trump stepped across the military demarcation line into North Korea, becoming the first sitting U.S. president to enter the country. The moment generated images that quickly circulated around the world and became a defining symbol of Trump’s North Korea diplomacy.

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The meeting reinforced Trump’s argument that his personal relationship with Kim had helped reduce tensions, even as broader negotiations remained stalled.

A Relationship That Still Draws Attention

The diplomatic process launched in Singapore ultimately failed to deliver the denuclearization breakthrough that negotiators sought, and formal talks later stalled. Yet the images continue to stand out because they documented a series of unprecedented moments: the first summit between U.S. and North Korean leaders, the first meeting between a sitting American president and a North Korean ruler, and the first time a sitting U.S. president crossed into North Korea.