President Donald Trump will look to seal the biggest diplomatic achievement of his second term when he travels to the Middle East to herald a deal ending the Israel-Hamas war and greet hostages emerging from two years of subjugation.

The fragile ceasefire stands as a major test of Trump’s dealmaking abilities, one that would bolster his goal of being remembered as a peacemaker, if it lasts. The president’s team is betting his personal guarantees — and the watchful eye of the U.S. military — can hold together the pact. Trump plans stops Monday in Israel and Egypt to celebrate the agreement and plot the next steps for a region shattered by the violence.

Still, anything could go wrong in the coming days that could undercut the deal, rendering it just another short-lived pause in a conflict between Arabs and Jews in the Middle East that long predates Israel’s founding 77 years ago. There are many ways the truce could sour — and those risks are all the more reason for Trump’s administration to remain involved, one U.S. official told reporters ahead of the trip.

If the deal holds, it would mark a major step toward a lasting peace that until now, neither Trump nor his predecessor, Joe Biden, was able to secure despite multiple negotiations following the outbreak of the war triggered by Hamas’ attack on Israel on Oct. 7, 2023. It came as the president exerted pressure on Israeli Prime Minister Benjamin Netanyahu, and used Arab allies to conduct shuttle diplomacy with Hamas, considered a terrorist group by the U.S. and European Union.

The return of hostages would deprive Hamas of a powerful bargaining chip it has used against Israel — but one that analysts say the group has decided is better used now. Convincing Netanyahu to gradually withdraw from Gaza and give up ambitions of taking control of the territory could stop the bloodbath there and give Palestinians a chance at reversing their global isolation.

“The Trump administration convinced both parties that continuing the war along the current trajectory is worse than entering its framework,” Michael Herzog, a former Israeli ambassador to the U.S., said Friday during a virtual event hosted by the Washington Institute think tank. “However, it’s clear that the big challenges are ahead of us. There are major questions about the next phases.”

The whirlwind trip is vintage Trump: the dealmaker-in-chief swooping in with the ink not yet dry — and fine print not yet hashed out. Still, for the president, the mere prospect of a deal is reason enough to head overseas, as he looks to codify his legacy.

“I think it’ll hold. They’re all tired of the fighting. Don’t forget you have Oct. 7th, which was a horrible day, 1,200 people killed, but Hamas has lost 58,000 people. That’s big retribution, that’s big retribution,” Trump said Friday, apparently referring to — and understating — the Palestinian death toll cited by the Hamas-run health ministry.

“But this is beyond Gaza. This is peace in the Middle East, and it is a beautiful thing,” Trump added.

Trump will arrive in Tel Aviv Monday, where he’ll meet with hostage families and address the Knesset, before heading to Sharm El Sheikh, Egypt, There, he’ll cohost a peace summit with Egyptian President Abdel-Fattah El-Sisi, with a slew of Arab and European leaders, including UK Prime Minister Keir Starmer, German Chancellor Friedrich Merz and French President Emmanuel Macron.

First deal

The Abraham Accords were seen as the biggest foreign-policy accomplishments of Trump’s first term, which saw several Arab and Muslim nations normalize relations with Israel. Hamas launched its brutal assault across the border two years ago amid speculation that one of the region’s biggest powers, Saudi Arabia, was ready to join.

Ending the war could give space for those talks to resume.

More urgently, it would stop the killing in Gaza and allow the shattered territory to start rebuilding from Israel’s attacks, which have caused a humanitarian disaster and left scores of civilians dead. The ferocious nature of Israel’s military campaign damaged relations with several traditional Western allies, which last month recognized a Palestinian state at the United Nations.

Ensuring the deal sticks beyond its first stage, a hostage-for-prisoner exchange between Israel and the Palestinians, won’t be easy. Key details remain up in the air.

Short clock

The White House announced Friday that a 72-hour clock to release hostages had begun, putting the onus on Hamas to deliver some 20 captives believed to be alive and the remains of others. Future stages of Trump’s outline, including how Hamas will disarm, which countries will make up a stabilization force to patrol Gaza and how quickly Israel’s forces will retreat and to where — are undecided.

“Inevitably, there are going to be conflicts here. They’re going to be things that the people in Gaza disagree with Israel about, that the Israelis disagree with the Gulf Arab states about,” Vice President JD Vance said Sunday on CBS’s "Face the Nation." “We see our role really, as mediating some of those disputes and ensuring that the pressure stays on everybody to achieve a durable and lasting peace.”

Front of mind is how the president will ensure that Israel does not take up arms in Gaza once it receives the hostages. Netanyahu and members of his right-wing coalition have said it’s imperative to destroy Hamas and that they can’t accept a future Palestinian state.

Trump “has made guarantees to Hamas, as far as we understand, that he will guarantee that Israel won’t restart this war. And I think it’s very unclear what the guarantees will look like,” said Will Todman, senior fellow at the Center for Strategic and International Studies.

Trump sidestepped a question Friday about guarantees but acknowledged work remained. “There is consensus on most of it, and some of the details, like anything else, will be worked out,” he said.

The deal came together quickly this week, following talks that started in August over a potential small-scale prisoner exchange. They produced a list of principles that would become Trump’s eventual 20-point plan.

Close aides

Top Trump envoy Steve Witkoff and the president’s son-in-law, Jared Kushner, flew to Egypt and then Israel to seal the deal Wednesday over a series of marathon meetings.

Trump joined at several points, with Witkoff or Kushner dialing him up and putting their iPhone on speaker to conference him in, U.S. officials said. Trump told his aides to get a deal done, and that the end of the war should not simply revert Gaza to what it was before.

Trump’s personal involvement, and the presence of close advisers, were an essential signal of U.S. involvement and crucial to convince the other parties to sign on, the officials said.

Trump has guaranteed that all sides would stand by the deal, one of the officials said. This week’s trip will double down on the pledge. So too will the allocation of 200 U.S. troops, some of them in Israel, to steward the establishment of an International Stabilization Force.

The U.S. officials said that Netanyahu trusts Trump won’t do anything to jeopardize their security — and that, therefore, they could discuss “creative” solutions with Israel about the future of Gaza and bat away requests from other countries that Israel won’t agree to.

That dynamic eliminated what one U.S. official called scenarios and stupidity that plagued prior peace talks.

The trip comes on the heels of the announcement of the most recent Nobel Peace Prize, which Trump had vigorously lobbied for. Ultimately, this year’s award went to Venezuela’s opposition leader. Should the Middle East deal last, Trump could have a strong argument to win it in the future.

_____

(With assistance from Josh Wingrove and Ros Krasny.)

_____

©2025 Bloomberg L.P. Visit bloomberg.com. Distributed by Tribune Content Agency, LLC.