On Sunday, Kim Jong-un arrived in Singapore in a plane he borrowed from China.

The journey is the farthest the North Korean leader has ever taken, due to both a lack of reliable travel options and the ever present concern a coup could erupt in his absence.

Later Sunday, Donald Trump landed in Singapore after refusing to sign a joint communique with other G7 nations and leaving the Canadian hosted summit early in protest.

Tomorrow, Trump and Kim will hold a historic meeting culminating a 180-degree pivot in US-North Korea relations relative to last year, when the two leaders were exchanging nuclear threats.

To understand what we can expect out of tomorrow’s meeting, it’s important to adopt a historical lens, while considering the distinct perspectives both nations bring to the table and the diverse perspectives that clash within each nation’s leadership.

From the summer of 1950 to the summer of 1953, the US fought a brutal proxy war on the Korean peninsula with the Soviet Union and China that killed over a million people and wounded millions more.

Though the war concluded with an armistice that divided the peninsula into North and South Korea, it has never officially ended and numerous flare-ups have occurred over the past 65 years.

In April 1975 after South Vietnam’s capital fell to North Vietnam, Kim Il-sung visited Beijing to ask Mao Zedong for support to invade South Korea but was turned down. Since 1974, four tunnels leading from North Korea to Seoul have been discovered and in 2010 North Korea killed 46 South Korean sailors, two soldiers, and two civilians.

As a result of North Korea’s continued provocations and relentless pursuit of nuclear weapons in the years following the 1953 armistice, they have become increasingly ostracized from the international community with a recent US-led campaign of “maximum pressure” raising the stakes with strict sanctions.

North Korea’s current “Supreme Leader” Kim Jong-un inherited the authoritarian throne held by his father and grandfather just in time to oversee the culmination of their nuclear ambitions, when in 2017 he tested intercontinental ballistic missiles that could be capable of delivering nuclear warheads around the world.

Kim has tested more missiles than both his father and grandfather combined, and though he hasn’t hesitated to escalate both verbal and military tensions with Trump, he also knows that without some concessions on the part of the US he’ll never be able to grow his economy.

Now that North Korea is an established nuclear power capable of bringing the US to the table, Kim has an opportunity his predecessors never did.

Thanks to the serendipitous election and diplomatic efforts of South Korean President Moon Jae-in, Kim now has a once in a lifetime opportunity to move North Korea away from its historically inwardly focused, isolationist stance with a singular focus on militarization.

Kim can now add a new chapter to the mythology that surrounds his family — the story of how their relentless pursuit of nuclear weapons above all else was a necessary sacrifice to earn the respect of US leaders, who only understand the language of force.

Any substantive outcomes from the Singapore Summit benefitting North Korea would be icing on the cake for Kim, the simple fact that the summit will take place is a victory itself.

Though Kim need not concede much beyond superficial shows of aggression in tomorrow’s meeting to call it a success, we can only speculate just how much he can feasibly concede without stretching the powers of his office beyond their breaking point.

What Kim may choose to concede tomorrow and how eager he may be to move forward with diplomatic relations come down to how much history he intends to write in one day.

Something similar could be said about President Trump, though that would be about where the similarities in circumstance end.

Politically speaking, Trump needs this summit more than Kim (it doesn’t hurt that dictators don’t have to worry about re-election) after provoking US allies with blanket tariffs and putting on a stubborn performance at the G7.

President Trump, Chancellor Merkel, and other world leaders at the G7 Summit in Canada. Photo by Jesco Denzel.

Much like Trump’s frustration is often the result of his own actions, US frustration with North Korea today dates back to our strategic error to push too far North during the Korean war.

Once we were too close for Mao’s comfort, China got involved and pushed the US further south to a stalemate with no peace treaty, leaving the neighboring states in a perpetual state of war.

Then we watched North Korea develop their military capabilities throughout the rest of the 20th century to the point where they are now a genuine nuclear threat. The entire time, no President has had any diplomatic or military success toward reducing the threat the regime poses to the US and our allies.

Now, we have a new President with an incoherent doctrine and chronically low approval ratings who is desperately seeking his first major accomplishment on the international stage as he alienates former allies left and ride with his isolationist trade policies.

If Trump plunges the US into a full blown trade war, he’ll no longer be able to use surface level statistics about the economy to bolster the false narrative that his administration and the tax cuts he signed are creating growth.

The President has nearly finished undoing just about every accomplishment of President Obama’s that he can get his hands on, leaving him little slack with the fragile coalition he’ll need to win re-election and making this summit his Hail Mary.

Trump already canceled the meeting once before changing his mind and deciding to go through with it after all, signaling some degree of self-awareness on his part that this will not be an easy needle to thread.

What’s clear is that Trump will have to give something up if he wants to walk away from the summit with any tangible achievements, what’s less clear is what he might be willing to give up and what he might demand in exchange.

Ultimately, there is a limit to how much progress toward denuclearization and official peace on the Korean peninsula will be made in Singapore on Tuesday. That limit will largely depend how comprehensive of a grasp both Trump and Kim have of their nuclear arsenals heading into tomorrow’s meeting.

Ideal outcomes include some sort of agreement between Kim and Trump to move forward with a mutually agreed upon framework for expert negotiations on denuclearization.

If the meeting goes well, we could expect to see plans for a trilateral summit between North and South Korea and the United States where the three nations would put forward a path for an official peace treaty, bringing an end to the 68-year-old war.

Considering Trump just shredded the expertly-negotiated Iran deal and refuses to acknowledge that there is anything he isn’t an expert on, agreeing to proceed with expert level negotiations would be an ironic, though not out of character step for him.

Another potential outcome is that the most historic thing about the summit is its occurrence, and the entire production ends up being little more than a highly-anticipated photo-op.

This would leave Kim with the victory he wants without requiring any real concessions on his part, while leaving team Trump empty handed and pitching spin about having built a foundation for a future denuclearization deal and peace treaty that may or may not materialize.

On the other hand, we should also be realistic about potential less-than-ideal outcomes. There seem to be few safeguards preventing this summit from devolving into a hostile exchange between Trump and Kim, an eventuality not entirely outside the realm of possibility as the two have traded harsh insults in the past.

If the leaders’ more hawkish advisors get the best of them, all bets are off and we risk returning to an incredibly dangerous escalation of hostility. If there’s one thing you should know about a potential war with North Korea it’s that no matter how bad you imagine it being, it’s infinitely worse.

Suffice it to say, the stakes for tomorrow’s summit in Singapore are high. History will be made no matter what happens, and according to Trump it will all come down to the “spur of the moment.”