The world will be watching this week as President Trump arrives for an historic meeting with North Korea leader Kim Jong Un.
The summit, held Tuesday at a luxury hotel on a secluded island in Singapore, is slated to be the first such meeting between a sitting U.S. president and North Korean leader.
Trump’s national security team has raced to finalize details on possible requests and concessions for the meeting, where Trump and Kim are expected to discuss efforts to denuclearize the Korean Peninsula.
Much remains unknown about the meeting – including who will ultimately have a seat at the table, what the U.S. will demand and what will happen when the meeting concludes.
Here are five things to watch at the summit, which kicks off Monday at 9 p.m. Eastern Time, 9 a.m. Tuesday in Singapore:
Does Trump stay on script?
While the first face-to-face meeting between a sitting president and North Korean leader is sure to require intense attention to detail, Trump has downplayed his own need to prepare.
“I think I’m very well prepared. I don’t think I have to prepare too much,” Trump told reporters after meeting with Japanese Prime Minister Shinzo Abe last week.
“This isn’t a question of preparation. It is a question of whether or not people want it to happen, and we’ll know that very quickly,” Trump said.
“It’s about attitude,” he added.
Those comments could suggest that Trump plans to speak more off the cuff, rather than from prepared remarks, when he sits down with Kim.
Trump has often taken a free-wheeling approach to his interactions with foreign leaders, drawing on his years of experience as a New York businessman and reality TV star.
But he will face particular scrutiny when it comes to securing specific concessions from Kim over Pyongyang’s nuclear program, with lawmakers sure to parse their every word.
“With [Intercontinental Ballistic Missiles] and nuclear warheads in the hands of North Korea, the situation is far too dangerous for seat of the pants negotiating,” Senate Minority Leader Charles Schumer (D-N.Y.) warned in a tweet last week.
Sen. Tammy Duckworth (D-Ill.) similarly said that Trump must not “undermine our own national security interests in search of a dramatic television moment consisting of more style than substance.”
Secretary of State Mike Pompeo sought to alleviate some of those fears last week, insisting the president has prepared through briefings on the military, economy and history of U.S.-North Korea relations “over months and months, days and days.”
“I am very confident the president will be fully prepared when he meets with his North Korean counterpart,” he said.
Does Kim lay on the charm?
The 34-year-old notoriously secretive North Korean leader has turned up the charm as the summit with Trump approaches.
At an historic meeting between the North and South Korean leaders in April, Kim was described as generally charming, reasonable and accommodating, The New Yorker reported.
During a banquet held at those talks, Kim was said to have toasted and hugged South Korean officials, and even brought a magician for the evening’s entertainment.
The image was held up by Pompeo, who after returning from his meeting with Kim in Pyongyang in April reportedly described him as “a smart guy who’s doing his homework.”
Kim also laid the groundwork for smoother talks with Trump by inviting foreign journalists to witness the closing of North Korea’s main nuclear weapons test site in May.
And in April, Kim pledged “complete denuclearization” at the meeting with South Korean President Moon Jae-in.
Experts expect a similar charm offensive, rather than bluster, at the meeting with Trump – though what Kim will employ this time around is anyone’s guess.
What exactly is on the table?
The Trump administration has so far kept quiet on specific goals going into the talks Tuesday, with them generally expected to center on North Korea’s denuclearization.
But Washington and Pyongyang have widely different views of what denuclearization looks like.
The U.S. has pushed for total, irreversible elimination of North Korea’s nuclear capabilities and testing, while the North sees the term as simply halting its development of such a weapon but keeping the work it has amassed over decades.
Asked last week if the administration has made progress in narrowing the gap between what the U.S. understands to be denuclearization and North Korea’s definition, Pompeo simply replied “yes,” but refused to give details.
He added that in his meetings with Kim, the North Korean leader “has indicated to me personally that he is prepared to denuclearize. That he understands that the current model doesn’t work.”
North Korea is also hoping for eased sanctions and a place back on the world stage.
Trump indicated Thursday he may be willing to offer such a concession, noting there is “tremendous potential” for North Korea to reap the economic benefits of striking a deal.
Kim, in turn, reportedly told Moon at the summit in April that Pyongyang would not need a nuclear weapon if the United States agreed to frequently meet and develop trust.
Also on the table this week is an agreement to end the Korean War, which stopped in 1953 but never had a formal peace treaty. Trump has said it is possible he and Kim could sign such a deal, which North Korea wants.
“We’re looking at it, we’re talking about it with a lot of other people … that’s probably the easy part, the hard part remains after that,” Trump said.
Th president has also said that he is “totally prepared to walk away” from the negotiating table if the summit does not meet his goals.
Who is influencing Trump?
Reports emerged earlier this month that despite the administration’s insistence that Trump was well prepared for the summit, national security adviser John Bolton hadn’t yet gathered Cabinet-level officials in a larger discussion with the president on the meeting.
The revelation suggests that Trump’s national security team is fractured when it comes to advice and preparation to give the president prior to the summit.
News also leaked that Trump is frustrated with Bolton after he referred to a “Libya model” for denuclearization during an interview in April.
The remark suggested that Washington would not give North Korea what it wants until it completely hands over its nuclear capabilities.
North Korea balked at the suggestion, responding with threats. Trump temporarily halted the meeting while reportedly placing blame on Bolton’s shoulders.
The rift seemed to remain earlier this month when a top North Korean official arrived at the White House and Bolton was not invited to the meeting in the Oval Office, Politico reported.
Bolton will, however, travel with Trump to the summit, according to presidential adviser Kellyanne Conway.
Pompeo, who has emerged as the lead negotiator for the U.S. over North Korea, is expected to have a prominent role during the trip to Singapore. Also in attendance will be White House chief of staff John Kelly and Defense Secretary James Mattis.
What happens next?
Many experts expect the summit to simply be the starting point in a push to denuclearize the Korean Peninsula, producing only a vague declaration on the path forward.
Pompeo alluded to such an outcome earlier this month when he said that the summit would put Trump and Kim in a position where “real progress” can be made.
He added last week that “it will take some amount time … this doesn’t happen instantaneously.”
Trump himself has suggested the U.S. may be willing to extend talks instead of insisting an instantaneous halt to North Korea’s nuclear and testing activities.
“Normalizing relations is something that I would expect to do, I would hope to do, when everything is complete,” Trump said during the press conference with Abe last week.
The president has even floated that if the meeting with Kim “goes well,” an invitation to the White House could be in the works.
“I think it would be well received and I think [Kim] would look at it very favorably. So, I think that could happen,” Trump said.
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