Does the Middle East Rest in the Hands of One Real-Estate Investor?

1. Can Witkoff Square the Circle?

There are moments in which it seems that the entire future of the Middle East rests in the hands of one real-estate investor. Not Donald Trump, the other one—Steve Witkoff.

Since being appointed to serve as Trump’s special envoy to the Middle East, Witkoff has gained an almost mythical reputation among U.S.-Israel relations watchers. 

His visit to Israel, even before Trump officially took office, and his now-famous insistence on meeting Netanyahu during Shabbat, have already become textbook material for dealing with a recalcitrant Israeli leader. Witkoff reportedly twisted Bibi’s arm into agreeing to the cease-fire deal, thus enabling the hostage release process to go into effect just in time for Trump to celebrate it as his first presidential foreign policy victory. In the month that has passed since that visit, Witkoff not only has become the top authority in Trump’s circle on everything relating to the Middle East (at times overshadowing the secretary of state and national security adviser), he has also been recruited to Trump’s Russia-Ukraine negotiation team after his 3.5-hour tête-à-tête with Vladimir Putin secured the release of wrongfully detained schoolteacher Marc Fogel.

Witkoff’s deal-making qualities may soon face their biggest test. On Wednesday he heads to the Middle East, tasked with what now looks like an impossible mission of getting Israel and Hamas to agree on ending the war, releasing all hostages and formulating a post-war mechanism to rule the Gaza Strip. 

The central question is: Will Netanyahu agree to implementing Phase II of the cease-fire agreement, which includes the release of all remaining hostages in return for a cessation of military operations and full withdrawal of Israeli forces from Gaza, or will he opt instead to relaunch military activities in order to “fully eliminate” Hamas?

“I think the Israelis have a red line, which is you can’t have Hamas in the government. And so it’s hard to sort of square that circle,” Witkoff said last week. Now, squaring that circle is his job. Witkoff’s marching orders include a blanket statement by Trump regarding his wish to see all hostages back and the war coming to an end, coupled with a no-less-vague statement by Trump that he will be “okay” with any decision Netanyahu makes on whether to stick to the deal or resume fighting.

Trump’s stance of deference toward any move Netanyahu makes could be seen as either catastrophic or brilliant. It could mean that Netanyahu, who has demonstrated in the past year and a half his preference for continuing the military conflict, now has a free hand to do just that and potentially drag Israel into an endless war at the expense of the hostages and the people of Gaza. Or, it could actually force Bibi to adopt a more pragmatic view, since any decision he makes will be his own, not a move he can blame on the U.S. administration. Netanyahu got a free hand from Trump to do whatever he wishes—now he will have to bear the consequences of whatever decision he makes.

Still, it is now on Witkoff to get a reluctant Israeli leader, a murderous and battered terror organization, and an uninvolved U.S. president to agree on a framework that will, in the very literal sense of the term, mean life and death for a great many people.

2. Trump’s Gaza Plan? That’s Yesterday’s News

It’s been only three weeks since President Trump announced his plan to expel the entire Palestinian population of the Gaza Strip and then have the United States take it over and turn the troubled piece of land into a Middle Eastern “Riviera.” 

But just as Trump floated the idea out of nowhere, it is now disappearing into thin air.

Facing persistent resistance from Egypt and Jordan, the two countries that according to Trump would have absorbed the displaced 1.8 million Gazans, as well as across-the-board rejection from all Arab nations, Western countries and from the Palestinians themselves, Trump now seems to have lost interest in his own dramatic initiative.

“I’ll tell you, the way to do it is my plan. I think that’s the plan that really works. But I’m not forcing it. I’m just going to sit back and recommend it,” Trump said in a radio interview on Friday. 

And just like that, the Gaza Riviera was downgraded from a key policy idea to a mere idea that the sides can either accept or reject, but that the president is not going to invest time and energy in convincing and negotiating. 

What happens next?

Trump is still waiting to formally hear back from Egypt after the Arab nations discuss the idea and come up with their counter-plan for Gaza. But the pressure on all players to accept the idea seems to be off. Middle East leaders can breathe a sigh of relief, all except for Israel’s Netanyahu, who enthusiastically embraced Trump’s idea and is now left holding on to a controversial proposal that its author is no longer pushing.

3. Turning L’s into W’s

Even though only a month has passed since Donald Trump took office, it’s not too early to look at his Middle East scorecard:

– Trump had demanded that all hostages be released before he was sworn in. He actually succeeded in securing a deal before January 20 and got credit for being the leader who managed to push the stagnant cease-fire deal across the finish line. True, not all hostages were released by that date, but Trump definitely kicked off the process.

– Gaza takeover: Again, the idea of turning it into the “Riviera of the Middle East” seems to have lost steam, but according to Trump’s advisers, even if the plan never pans out, it is still a victory because by presenting it, Trump pushed Egypt, Jordan and the other Arab states to come up with a plan of their own for rebuilding Gaza.

– Last week’s threat that “all hell would break loose” if all hostages weren’t released: This did not happen. Hamas released only three hostages that day, but Trump and his team don’t see this as a failure. On the contrary, by setting the ultimatum, the White House argued, Trump forced Hamas to live up to its commitment in the agreement to release the three hostages.

4. How DOGE Cuts Will Impact Jewish Priorities

With the battle over the future of the federal government still raging, Jewish advocates are trying to figure out how the new Trump-Musk actions will impact their communal priorities.

Most of the early moves are seen as attacking not the community itself but its values and policy priorities, which for the most part overlap with those of the Democratic Party.

A few examples:

The Jewish community is among the most pro-immigration groups in America. Everything Trump has said and done, including the already enforced cuts in funding for refugee resettlement, is viewed as problematic by most of the Jewish community. (With even more anger directed at the new administration’s intent to allow ICE to raid houses of worship in search of undocumented immigrants.) 

The same is true when it comes to cutting foreign assistance provided by USAID, slashing medical research budgets, firing federal workers en masse and revoking environmental safeguards.

Some budget issues that are of specific concern to the Jewish community are still being closely watched: Foreign aid to Israel has not been touched and is not likely to be cut; no word yet about Department of Homeland Security grants for securing Jewish institutions; and there is still a big question mark regarding how the new attorney general will deal with devoting resources to battle white nationalist, anti-Jewish hate crimes.

5. But Some Causes Are About to Benefit

Many in the Orthodox Jewish community are eagerly expecting the Department of Education (if it remains active) and other government agencies to allow more federal funding for religious schools. The lower the wall separating church and state on issues of funding, the better off Orthodox and ultra-Orthodox education institutions are.

In addition, the Executive Order on Antisemitism signed by Trump focuses on uprooting anti-Israel campus activities that veer into antisemitism. It also calls for direct actions against foreign students expressing support for Hamas. This largely symbolic act signals the administration’s commitment to fight campus protests, a move that many in the pro-Israel community will welcome. 

Top image: Steve Witkoff (Photo credit: U.S. Department of State / TownDown (CC BY-SA 3.0)).