The former U.S. official said many of the Trump administration appointees focusing on North Korea lack serious diplomatic experience in the region, and they are not coordinating well enough with American diplomats who deal with countries such as South Korea, Japan and China.

Working with those countries is crucial, especially if Kim is replaced as the head of the regime. But the U.S. relationship with each of those states is frayed.

The Trump administration has made no secret of its view of China as a threat to the U.S. in areas ranging from cybersecurity to trade. The two countries have in recent months engaged in a war of words over who is to blame for the spread of the coronavirus, which emerged in China’s Hubei province.

But China is North Korea’s most important economic partner, and often its shield at multilateral forums such as the United Nations. It is deeply wary of destabilizing the regime in Pyongyang politically or economically, for fear it will have a massive humanitarian and refugee crisis on its borders.

For U.S. or international sanctions on North Korea to work, China has to go along. Sometimes it does — such as in 2017, as Trump led a maximum pressure campaign against Pyongyang. But that Chinese commitment is rarely 100 percent; Beijing has pushed Trump to relax sanctions in more recent years.

Japan and South Korea are historically close U.S. allies that house American military bases, but both have felt bruised by Trump’s tariff-heavy actions on the trade front. They’ve also felt insulted by his demands that they pay much more to cover the cost of keeping U.S. troops in the region. At times, the two – especially Japan – have had to scramble to stay looped in on U.S.-North Korea policy.

Trump’s investment in Kim could also complicate the dangerous period that accompanies a transition of power in a country ruled by fear and force.

The U.S. has developed past contingency plans for how to deal with a North Korean change in leadership, but they have been “premised on ongoing relationship, especially with the allies – clarity of what we want to do, and what they want to do, and similar clarity with China,” the former U.S. official said.

Current and former officials, as well as outside analysts, do not underestimate the challenge any administration has in dealing with North Korea, and they do not all fault Trump for initially throwing out convention in sitting down with Kim.

The history of U.S. diplomacy toward North Korea is rife with failure and frustration. Past sitting U.S. presidents, Democratic and Republican alike, never met with their North Korean counterparts, and yet struggled and ultimately failed to permanently dismantle North Korea’s nuclear arsenal. Trump’s predecessor, Barack Obama, was accused of essentially giving up on the North Korea nuclear issue, even as he managed to strike a nuclear deal with Iran.

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Kim’s father, Kim Jong Il, and his grandfather Kim Il Sung did not make things easy for U.S. envoys. Kim Il Sung died in July 1994 shortly after meeting with former President Jimmy Carter and expressing a willingness to suspend his country’s nuclear program and establish relations with the United States.

Kim Jong Il oversaw the initial implementation of that resulting 1994 arrangement called the Agreed Framework, but over time, that deal collapsed, with both sides casting blame on the other. Kim Jong Il died Dec. 17, 2011; his passing caught the U.S. intelligence community off-guard, according to reports at the time. By then, North Korea was suspected to have a still-small nuclear arsenal.

Before Trump, the general U.S. blueprint for negotiations with Pyongyang — or any government, really — involved starting at lower levels. Diplomats from the State Department, for instance, would meet with North Korean counterparts to hammer out basics, such as confidence-building measures, with the goal of eventually pushing the talks upward.

Trump, a political neophyte, campaigned for the presidency in part on his reputation as a dealmaker from his real estate days. Obama warned him that North Korea may prove the top threat facing the United States, and Trump spent much of his first year trading insults and threats with Kim Jong Un.

He promised “fire and fury” if North Korea made any threatening moves and heaped economic sanctions on Kim’s regime. Kim called Trump a “dotard” and pressed ahead with missile tests and other nuclear-linked actions.

At the behest of South Korea, Trump eventually agreed to meet with Kim. The pair first met in Singapore in June 2018, appearing friendly and signing a vague declaration promising to work toward denuclearization.

They met again in Vietnam in February 2019, but ended the summit early when Trump said he could not agree to Kim’s proposal that he lift numerous U.S. sanctions in exchange for modest curbs on North Korea’s nuclear program.

The pair nonetheless met once more later that year at the Demilitarized Zone, the boundary that separates North and South Korea. Trump became the first sitting president to set foot on North Korean soil.

Trump also has repeatedly boasted of his warm personal ties with Kim, even saying the two “fell in love.” The pair also have exchanged letters.

There are signs, however, that even that relationship is cooling. After a lengthy moratorium amid talks with Trump, North Korea resumed testing missiles months ago. North Korea also swiftly denied a Trump claim earlier this month that he’d recently received a note from Kim. The North Korean statement warned Trump not to use the relationship for “selfish purposes.”