There’s nothing like the drama of a deadline. But when President Donald Trump told Hamas it had until Saturday afternoon to release all of the Israeli hostages or “all hell is going to break loose,” he escalated the stakes of a fragile truce: Either Hamas can accelerate the terms of the ceasefire agreement—freeing dozens of captives now rather than in stages—or Israel can resume pummeling the Gaza Strip in a conflict that has already claimed more than 47,000 lives.

For Trump, it’s a tactic he outlined in his 1987 bestseller The Art of the Deal: Always be willing to walk away. “The strategy is simple,” says a senior White House official. “Hamas made commitments. They’re playing games, and the President was very clear that the burden is on them to keep this thing on track. If they don’t, then there’s repercussions.” 

Sources close to Trump say that he’s making a calculation: He thinks he can force Hamas into making more concessions by leveling a full-bore threat. If it works, his aides say, the President will be able to claim an early win in his second-term stewardship of U.S. foreign policy. If it doesn’t, critics counter, it could lead to more death and destruction in the already devastated coastal enclave. “We have a Mexican standoff here that could easily end badly,” says Aaron David Miller, a veteran diplomat.

Already, Trump’s threat seems to have moved Hamas. On Thursday, the terrorist group said it would return to releasing Israeli hostages “according to the specified timetable.” It’s not clear whether that will satisfy Trump, who has said he wants an end to the drawn out process. Israel has also not yet responded to Hamas’ offer.

So far, Hamas has freed 16 of the 33 Israeli hostages slated to be released in the first phase of the deal struck in January. Israel, for its part, has released more than 600 Palestinian prisoners. Roughly 60 more hostages—some of whom are believed to be dead—are scheduled to be released later this spring. But Hamas threatened to blow up the whole arrangement when it announced on Monday that it was indefinitely suspending the release of any more hostages, alleging “Israeli violations” of the pact. The declaration from Hamas, which is slated to release three more hostages this week under the deal, came nearly a week after Trump shocked the world by saying the U.S. planned to take over Gaza and permanently displace two million Palestinians so he could transform it into “the Riviera of the Middle East.”

Shortly after the Hamas communiqué, Trump issued his ultimatum and reiterated his desire to rebuild the territory into an oceanfront tourist destination. “They either have them out by Saturday at 12 p.m. or all bets are off,” he said in the Oval Office, sitting next to a visibly uncomfortable King Abdullah II of Jordan. “We will have Gaza. It’s a war-torn area. We’re going to take it.” 

Echoing Trump, Israeli Prime Minister Benjamin Netanyahu issued his own warning Tuesday, saying that “intense fighting” would resume in Gaza if the hostages are not returned by Saturday. Yet he notably did not say Hamas had to free every one of the captives. To that end, some analysts suspect the two sides may reach a compromise before the weekend. 

Miller, a fellow at the Carnegie Endowment for International Peace, argues that Hamas has little incentive to accede to Trump’s maximalist demand. “Hamas has one card left, and that’s the hostages,” Miller says. “They’ll hold as many of them as long as they possibly can. It’s their only leverage.” For that reason, the Islamist group may see an off-ramp in releasing nine of the living hostages slated to be released in Phase 1, he adds, rather than the three due on Saturday. “If Hamas releases the nine, bingo, it’s a win for everybody,” says Miller.

For Trump’s national security team, the images of the three Israelis let free on Saturday only intensified the push to get the rest back quicker; three male hostages returned to their homes emaciated and showing myriad signs of having survived 490 days of torture. “I think the condition that the last three were in exacerbated this,” says a Trump official. 

The prospect of renewed hostilities in the wake of Trump’s pronouncement has left Netanyahu’s circle with the impression they will be given carte blanche in how they attack Gaza. That would mark a sea change from the pressure exerted by the Biden Administration to scale back Israel’s incursion and limit humanitarian costs. “The big difference today is we don’t have the Americans limiting us. We have a total green light from the American administration,” says an Israeli official. “If we go back to fighting in Gaza, you are going to see very, very tough pictures coming out of there.”

Trump’s ultimatum comes as he seeks to radically remake the map of the Middle East: He said last week he wouldn’t deploy American troops to oust Hamas from Gaza, but that the U.S. would enter the coastal strip after Israel completes its military operation to begin a lengthy process of reconstructing the beleaguered strip. He said America would gain an “ownership position” of the land. And he clarified this week that Palestinians would not have the right to return to their homes, predicting Jordan and Egypt would accept most of them. 

Few Middle East experts see Trump’s proposal as feasible. Arab states recoil at the notion of forcibly displacing Gazans and fear the destabilizing potential of absorbing Palestinian refugees. International humanitarian groups have said it would amount to ethnic cleansing. But for some in Israel, the outlandish idea is picking up steam. “Trump’s plan is so left field, so out of the usual discourse, that even the opposition here is saying okay,” says an Israeli lawmaker outside the Netanyahu coalition. “If Trump wants to try something, let’s try it.” 

A sign of momentum, they say, was King Abdullah II agreeing to accept two thousand sick Palestinian children after Trump threatened to cut off aid to Jordan and Egypt. “We are already starting to see cracks,” says the Israeli official, who also points to Trump, as President-elect, threatening Hamas similarly before it agreed to the January ceasefire. 

Others are less optimistic. They see it as Jordan’s way of placating Trump while accepting only a tiny fraction of the millions of civilians trapped in Gaza. At the same time, Egypt’s President, Fattah al-Sisi, postponed a planned visit to the White House out of concern for the optics of appearing alongside Trump as he’s pushing an idea that is anathema to the Egyptian population. 

But the real test for what unfolds next may be on Saturday—whether Hamas tries to stave off another armed confrontation or risk the fallout. “This weekend is a very simple inflection point for them,” says the White House official. “They can get back on track with the commitments they’ve made, or face a whole new round of consequences.”