For US presidents, their first big overseas trip is basically a debutante ball: It’s meant to introduce the new president on the world stage and induct them into the high society of powerful world leaders. And for most US presidents, it’s an important but still relatively low-stakes affair, with kings, emirs, and presidents rolling out the red carpet to wine and dine the American president and stage smiling photo ops.

But Donald Trump isn’t most US presidents, and the stakes couldn’t be higher for his first trip abroad. All eyes will be watching Trump’s every move to see if he can really hack it as a serious world leader or whether he’ll have the same stumbles abroad that he’s been having at home.

And Trump is making his debut on the world stage in one of the most politically complex places on earth: the Middle East. He leaves late Friday for a two-day trip to Saudi Arabia, followed by a day-long trip to Israel on Monday (and then a short stop at the Vatican, meetings with European leaders in Sicily, and finally a NATO summit in Brussels, Belgium).

Navigating the tricky world of Middle East diplomacy is tough for even the most seasoned diplomats — and Trump is very emphatically not a seasoned diplomat. He tends to go off script, blurting out whatever pops into his head regardless of whether it’s even remotely appropriate or accurate.

With his young presidency mired in nonstop scandals, public relations gaffes, and political chaos, Trump could really use a big win right about now. And the White House is desperately praying that the big foreign trip will be that big win.

But early in his presidency Trump couldn’t even manage to give a simple speech to a room full of CIA officers in front of a wall honoring their dead — a speech meant to mend fences with and show support for the intelligence community — without pissing off nearly the entire room full of CIA officers.

Just imagine the potential damage he could do if he decides to riff while laying a wreath at Yad Vashem, Israel's official memorial to the victims of the Holocaust. Or if he ad libs while delivering his major speech on Islam to an audience of more than 50 leaders of Muslim countries.

That’s what has Trump’s aides — and more than a few ordinary Americans — worried. This trip is Trump’s first real chance to establish himself as a strong, capable world leader — but only if he doesn’t screw it up.

And so far, things aren’t looking too good.

Trump is giving a speech on Islam. In Saudi Arabia. Written by the architect of the “Muslim ban.”

During the campaign, Trump said that “Islam hates us,” called for “a total and complete shutdown of Muslims entering the United States,” cited dubious polls he said showed that a sizable segment of the Muslim population has "great hatred towards Americans," and falsely claimed that he personally witnessed “thousands” of Arabs celebrating in the streets of New Jersey on 9/11.

And, of course, just seven days after taking office, he signed an executive order temporarily banning people from seven Muslim-majority countries from entering the United States.

Now, he wants to mend relations with the leaders of Muslim world — perhaps because, as foreign policy experts and his current national security adviser have been trying to tell him for a while now, he actually needs their help to fight terrorism.

He’s apparently decided the best way to do this is to give a major speech on Islam and radicalism — or, sorry, “radical Islamic terrorism,” as Trump insists it must be called, despite the urging from his National Security Adviser H.R. McMaster to drop the potentially offensive phrase.

He’ll be delivering this grand speech in Saudi Arabia, the country that hosts the two holiest sites in Islam, to an audience of more than 50 leaders of Muslim countries. And he’s having his aide Stephen Miller — who was one of the key architects of Trump’s “Muslim ban” and has a long history of espousing anti-Muslim views — write the speech.

Let’s just pause for a second to let that sink in: Trump’s plan to improve relations with the Muslim world is to travel to the birthplace of Islam and deliver a big speech written by his anti-Muslim adviser about the religion’s problem with extremism in front of more than 50 Muslim leaders.

Solid plan.

To be sure, the Saudis themselves, along with many of the other leaders who will be at the meeting, have a lot of incentive to give Trump a fair amount of latitude even if he does say things they don’t like. The Saudis are nearly giddy that they have Trump instead of Obama to deal with now. He is hawkish on Iran and, at least verbally, opposes the Iran nuclear deal, and he’s more than willing to sign billion dollar arms deals with them without lecturing them on human rights.

But that only goes so far. Much of the Saudi royal family’s legitimacy comes from their control over the two holiest sites in Islam. Which means that if Trump says something truly outrageous and offensive about Islam, they’ll have a hard time just letting it go unchallenged.

Israel: the easy win that’s now anything but

When Trump chose to add Israel to his itinerary, it was supposed to be an easy win — after all, Israel is one of America’s closest allies. And when he was elected, Trump promised to put an end the Obama administration’s “disdain and disrespect” for Israel as soon as he took office and be the friend Israel truly deserved.

Israeli Prime Minister Benjamin Netanyahu was ecstatic:

President-elect Trump, thank you for your warm friendship and your clear-cut support for Israel! @IvankaTrump @DonaldJTrumpJr https://t.co/lURPimG0wS — Benjamin Netanyahu (@netanyahu) December 28, 2016

Surely, there’s no way Trump could mess this one up. It’s a slam-dunk — the perfect opportunity for Trump to show Americans and the world that not only is he a capable leader, he’s even more savvy at diplomacy than Barack Obama

You might already see where this is heading.

Earlier this month, reports came out that Trump would be visiting the Western Wall in Jerusalem, one of the holiest sites in Judaism, during his Israel trip — making him the first sitting US president to ever do so.

Past US presidents have avoided visiting the Western Wall while in office because it happens to be at the center of one of the most contentious issues in the Middle East: control over the holy sites of Jerusalem.

The wall is located in the Old City of Jerusalem, which Israel captured from Jordan during the Six-Day War in 1967. But some Muslims believe the wall is part of the al-Aqsa Mosque, a holy site in Islam, and therefore should be controlled by the Palestinians (or at the very least not controlled by Israel).

The international community — and official US policy historically — doesn’t recognize Israel’s authority over the Western Wall, asserting that the final status of who controls what in Jerusalem is subject to negotiations with the Palestinians. But Netanyahu — and most of the Israeli public, as well as world Jewry and many politically powerful American Evangelical Christians — are adamant that the Western Wall, and indeed all of Jerusalem, is and always will be part of Israel.

So by visiting the Western Wall during an official state visit to Israel, Trump would be making a very symbolic gesture implying that the US recognizes that the Western Wall does indeed belong to Israel.

It was a huge deal, and many Israelis were ecstatic, with some speculating that Trump might use the occasion to announce that he’d finally be fulfilling his campaign promise of moving the US embassy in Israel to Jerusalem (yet another contentious issue). Netanyahu’s office even asked the Trump team in charge of planning the visit if the prime minister could accompany the president to the wall — which would be an even more symbolic gesture.

And that’s when the Trump administration royally stepped in it.

Israel’s Channel 2 news reported on Monday that a senior member of Trump’s staff rejected the request, saying it would be a “private visit.” Then when the Israelis asked if they could at least send a camera crew along to film Trump’s visit, things got heated. “What are you talking about?” the Trump official reportedly fired back. “It’s none of your business. It’s not even part of your responsibility. It’s not your territory. It’s part of the West Bank.”

The Israelis were stunned, and the prime minister’s office immediately put out a statement demanding the White House clarify. An unnamed White House spokesperson told CNN Tuesday morning that "These comments were not authorized by the White House. They do not reflect the US position, and certainly not the President's position."

Okay, then. Problem solved, crisis over. Right?

Nope.

At a press conference just a few hours later, Trump’s National Security Adviser H.R. McMaster twice refused to answer direct questions about whether the administration considers the Western Wall to be part of Israel. McMaster would only say that the question "sounds like a policy decision.”

When asked the same question by reporters a little while later, White House Press Secretary Sean Spicer responded that “The Western Wall is obviously one of the holiest sites in Jewish faith. It’s clearly in Jerusalem.” But, as my Vox colleague Sarah Wildman points out, “that response actually did not answer the question on whether the wall was in Israel. The city wasn’t in question, the nationality of that city was.”

The White House doesn’t seem to have made any further attempts to clarify, at least in public. Which, given how they’ve done so far, is probably a good call. And as of now Trump’s still going to the Western Wall for a private visit. But even if they have managed to smooth things over with the Israelis, it’s not exactly the best way to start things off.

On top of that, Trump’s also planning to travel to Bethlehem to meet with Palestinian president Mahmoud Abbas — a decision that both surprised and irked many on the right in Israel who would very much prefer that the new US president focus solely on Israel and give the Palestinian leadership the cold shoulder.

Trump’s personal idiosyncrasies are only making things worse

In just a few short months in office, Trump has already become known for his short attention span, his bizarre aversion to any kind of physical exercise more strenuous than golf, his strong dislike for staying anywhere that isn’t Trump Tower or a Trump resort, and his general insistence on acting like a rich, spoiled businessman instead of a public servant and the leader of the free world.

That’s proven problematic enough here at home. Now he’s embarking on a grueling, nine-day, multi-country trip to the Middle East (and later Europe).

And it’s already causing problems.

Trump was scheduled to deliver a speech at the ancient desert fortress of Masada, a symbol of Jewish resilience and courage — but Newsweek reported today that Trump abruptly canceled the Masada visit when Israel told him he couldn't land his personal helicopter on top of the site and would just have to take the cable car up just like every other previous visiting US president has.

And then there’s Trump’s decision to visit Yad Vashem, Israel’s official Holocaust memorial museum. “Yad Vashem is a traditional stopping point for almost all foreign officials visiting Israel. Barack Obama spent an hour in the museum. George W. Bush stayed even longer,” explains Vox’s Wildman.

And Trump? “Advance readouts of Trump’s itinerary reveal he plans a whopping 15 minutes,” Wildman writes. Trump may have a notoriously short attention span, but one would think that a president who has been accused of dabbling in anti-Semitism and Holocaust denialism might try to make just a tiny bit more effort when it comes to visiting one of the most emotionally and historically symbolic sites to the world’s Jews.

In fact, Trump’s short attention span is so well known that NATO is reportedly “scrambling to tailor its upcoming meeting” with Trump in Brussels on the 25th in order to “avoid taxing” him too much. “The alliance is telling heads of state to limit talks to two to four minutes at a time during the discussion,” writes Foreign Policy’s Robbie Gramer.

“It’s like they’re preparing to deal with a child — someone with a short attention span and mood who has no knowledge of NATO, no interest in in-depth policy issues, nothing,” one source told Gramer. “They’re freaking out.”

Terrific. Trump (and, well, America, to be quite honest) really needs to be able to come across as, at the very least, a moderately competent leader during this trip. But so far, he looks like a bumbling fool at best and a fussy toddler at worst.

And the trip hasn’t even started yet. God only knows what might happen once he’s there — jet-lagged, cranky, and totally out of his element.

"Something will go wrong. That we know, but we don't know what," one Israeli politician told CNN, only half-joking, when asked about Trump’s upcoming trip. "A successful visit right now is for it to be over.”

But he could pull it off — if he’s on his best behavior

There are a lot of things Trump isn’t: a professional diplomat, a nuanced thinker, a seasoned politician, a polished orator, an adventurous world traveler.

But he is a showman. He has charisma. He knows how to work a crowd. And many, many people who’ve met with him one on one have come away saying that he was a lot more charming in person than they ever expected, and much more prone to listening to their views rather than simply repeating his own. Those aren’t skills to snub your nose at, especially when it comes to schmoozing with foreign leaders.

He’s also someone who appreciates ostentatious wealth, over-the-top pomp and circumstance, and flattery. And he’s going to be in places like freaking Saudi Arabia, where he’ll receive a red-carpet welcome from some of the most ostentatiously wealthy people on the planet. He’ll be put up in the most lavish rooms that will probably make a Trump Hotel look like a Motel 6 and fed only the finest cuisine.

And pretty much everywhere he goes, he’ll be treated like the most powerful man in the world — because in these meetings at least, he will be.

Trump loves that. And coming off of four straight months of being battered daily by mounting scandals and scathing criticism, and having his every move blocked, reversed, or ignored by judges and members of Congress — who, it turns out, have just as much power as he has — he’ll probably love it even more.

And while he’ll no doubt still be as obsessed as ever with reading or watching every single thing said about him in the US media while he’s abroad, even just the physical removal from the insanity of Washington may be a welcome respite. Indeed, that seems to be part of the reason why he goes to Mar-a-Lago so often on the weekends instead of staying in the White House.

As anyone who’s ever traveled abroad knows, no matter how connected you still are to Twitter, the hubbub of politics back home always seems to feel a bit more distant once you’re in a foreign country. And that could only be a good thing for Trump.

But, perhaps most important of all, Trump surely knows what’s on the line here. If he stays on script — and if the script is vetted by some of the more sober-minded and experienced members of his Cabinet to keep out anything catastrophically explosive — he just might pull it off.

Or, maybe more likely, he won’t.