A Moment Of Truth In The Middle East For Donald Trump — And Steve Witkoff

President Donald Trump’s visit to Saudi Arabia, Qatar and the United Arab Emirates this week will highlight how his presidency is affecting the Middle East, where tens of millions of people are in crisis.

But it will also be a big moment for a different powerful American: Trump’s special envoy for the region, the 68-year-old real estate billionaire Steve Witkoff. The visit could vindicate his ambitious strategy, or sound an alarm about how he and his boss are operating.

“This is a key potential inflection point for the administration’s Middle East policy,” said Sina Toossi, a senior fellow at the Center for International Policy think tank. “There’s this space for a more peaceful Persian Gulf region where the U.S. tries to maximize what it can get from these countries vis-a-vis China,” amid growing American anxiety about partners growing closer to Beijing.

Many regional officials see Witkoff “as a more even-handed negotiator and interlocutor” than past American counterparts, said a former U.S. official familiar with Witkoff’s team, noting the impression that the Biden administration prioritized America’s relationship with Israel above all else. The Trump envoy is “understated and results-oriented,” offering “a positive strategic departure from American business as usual in the Middle East,” they argued.

However, Witkoff also reflects defining characteristics of the Trump administration, like inexperience, disregard for norms, and potentially mixing public and private interests.

He has become known for little coordination with other American officials, traversing regional capitals on his private jet with a handful of close aides, many of them young and without national security experience, as well as private business contacts interested in real estate opportunities in the Middle East, the former U.S. official said. His girlfriend, former professional golfer Lauren Olaya, often joins sensitive trips too, per CNN.

Early in his tenure, Witkoff’s style risked a crisis when his plane approached the airspace of the U.A.E. without providing prior warning ― alarming Emiratis, whose country has faced aerial attacks for years. They refused to let him land until American diplomats, who had themselves been blindsided, managed to assuage their concerns, saying there was a miscommunication, a regional source told HuffPost.

Witkoff has made a habit of extensive private and potentially momentous dealings with foreign interlocutors, suggesting his counterparts have faith in him. But such deals also make it harder to have transparency or coordination in U.S. policy-making, and risk relying too heavily on one official’s skills.

Some senior officials in Middle Eastern governments spend two to three hours chatting with Witkoff daily via WhatsApp, according to Khalid Aljabri, a well-connected commentator on the relationship between the U.S. and Saudi Arabia. On another visit to the U.A.E, Witkoff spent nearly 10 hours alone with Emirati President Muhammed bin Zayed, providing no official readout to colleagues about what seemed like “a black hole,” the regional source said, adding that though Eric Trager, the top Middle East official at the White House, was on that trip, he was not included in the discussion. The lack of transparency is “making things very difficult for embassies in the region,” the source said.

Karoline Leavitt, the White House Press Secretary, praised Witkoff’s tactics in an email to HuffPost. “Special Envoy Witkoff is working at the direction of President Trump in solving problems at the negotiating table rather than the battlefield, ” Leavitt wrote. “Unlike Joe Biden, who was incapable of talking to both sides, President Trump and his team are uniquely able to look anyone in the eye to negotiate deals that secure peace and prioritize the United States of America.”

The Trump envoy’s team seems to almost relish complaints about its approach. “They have all these catchphrases like, ‘We’re not process-oriented but outcome-oriented,’” a Western official told HuffPost. “They have disdain for bureaucracy, and they are not interested in fitting the mold of conventional diplomatic norms because they think this is part of the reason U.S. diplomacy has been failing.”

Dysfunction could doom Witkoff’s efforts, however, producing unexpected and dangerous scenarios, and threatening U.S. interests, while spurring chaos within the Trump administration by strengthening skepticism of him among some influential conservatives.

Witkoff embodies Trump tendencies that are maddening for some in and close to the historically hawkish Republican ecosystem, from wealthy donors to pundits. His engagement with U.S. foes like Iran and Russia, and seeming disregard for conventions like deference to Israel, reflect how Trump largely sees global affairs in personalistic terms ― a tendency that is core to efforts by some in the president’s circle to reduce American involvement abroad.

Supporters of more assertive U.S. policies, including Republican members of Congress, have labeled Witkoff as misguided. Vice President J.D. Vance and Donald Trump Jr. have attacked Witkoff’s critics as pro-war. The fracture in GOP thinking about Middle East policy has already contributed to significant shifts by the administration, like Trump’s decision to remove Mike Waltz as national security adviser after he reportedly frustrated the president by discussing attacking Iran with Israeli Prime Minister Benjamin Netanyahu.

A senior administration official defended Witkoff.

“Not surprisingly, the swamp is disturbed when a person comes along who thinks outside the box and does things differently ― the very same people who have spent their careers loving bureaucracy with nothing to show for it,” the official wrote in an email to HuffPost.

“Witkoff has done incredible work securing the release of Americans detained abroad, like Edan Alexander and Marc Fogel, while leaving behind a massive business enterprise to serve his country ― all on his own dime,” the official continued. “All his work is coordinated with the other members of the President’s foreign policy team, including Secretary Marco Rubio, who is a close personal friend. It’s one team, one mission. And Steve is supported by an experienced team who work together to support his efforts at advancing President Trump’s agenda.”

The run-up to Trump’s departure brought a new wrinkle in how the president’s coalition is handling Middle East policy, and a sign the current approach may soon face even more intense criticism.

A particular fixation of pro-Israel hardliners is Qatar, the Persian Gulf emirate that helps the U.S. negotiate with the Palestinian militant group Hamas. Witkoff’s critics have highlighted his past business with Qatar as they have questioned his handling of diplomacy over the Israel-Hamas war. The news that Trump himself wants to accept a luxury jet as essentially a personal gift from the Qataris brought fresh attacks about the administration’s ties to Qatar, including from a notable voice in the Trump-world faction usually supporting Witkoff and a less hawkish policy, the far-right activist Laura Loomer.

The unfolding scandal and the trip come as the stakes of the Trump administration’s Middle East choices become more clear.

Witkoff’s ongoing diplomacy over Gaza bore fruit on Monday when Hamas freed its Israeli-American hostage Edan Alexander in a win for Trump and his envoy. The moment exemplified how any change in the Israel-Hamas war likely depends on American moves – at a point where the status quo of an Israeli blockade has left 1 in 5 Palestinians in Gaza facing starvation, and where Netanyahu says he plans to expand Israeli attacks despite pleas from many Israelis to cut a deal and free the remaining Hamas hostages.

Meanwhile, Witkoff’s talks with Iran about limiting its nuclear program are advancing but face a looming deadline: For the negotiations to continue, some kind of interim settlement is vital within a matter of weeks, experts say. The alternative is further tension in a still-unsettled region.

Business ties between the U.S. and the wealthy Gulf monarchies are ostensibly the priority of Trump’s trip this week, but with regional players and Washington observers intensely tracking his team’s moves, “There will definitely be a more diplomatic segment,” the Western official said.

For the 2.1 million Palestinians in Gaza, a shift in U.S. policy in the region is an existential necessity.

Since Israel in mid-March broke a ceasefire that Witkoff helped craft, its renewed offensive has killed at least a thousand people ― including through strikes on Sunday on a school and a mosque whose victims included children ― while its 10-week ban on supplies has created unprecedented hunger in the strip. Palestinians are now reporting deaths from malnutrition, like that of a 4-month-old, Jinan Iskafi, on May 3. “She was like a small miracle, but I couldn’t feed her, I couldn’t protect her,” her mother Aya told Amnesty International.

Trump and his staff have indicated they are frustrated with Netanyahu’s resistance to a ceasefire agreement. “We want to bring the hostages home, but Israel is not willing to end the war,” Witkoff reportedly told relatives of Israeli hostages captured on Oct. 7, 2023, in the Hamas-led raid that began the current round of fighting. Notably, he did not brief Israel about discussions with Hamas about Alexander, the Israeli-American hostage, until he sealed the deal.

Witkoff is personally wary of the Israeli leader, three sources told HuffPost, with one saying the Trump envoy has told people Netanyahu “played” him by abandoning the previous ceasefire. (Publicly, Witkoff blamed the breakdown on Hamas.) His limited progress on Gaza since then has been in part because Witkoff has struggled to focus Trump’s attention on pushing Netanyahu to reach a deal, the regional source said, though they also noted he has a “barely functioning circle” of staff.

Amid Alexander’s release, the president expressed hope it will be “the first of those final steps necessary to end this brutal conflict,” and U.S. officials have said they want to see less suffering among Palestinians. Still, Trump has sustained extensive military support for Netanyahu and endorsed some of his hard-right allies’ most bellicose ideas, like expelling Palestinians from Gaza.

The way the administration ― including Witkoff ― is handling aid for Gaza shows how lasting peace in the region, including through tough conversations with Israel given the U.S.’ unique leverage over the country, may prove elusive if their priority is PR wins.

The Trump era began with officials taking a literal chainsaw to America’s role in international humanitarian work, baselessly claiming many landmark aid programs were defined by fraud and waste, and halting much of the U.S. funding for global relief efforts.

Now, amid high-profile distress in Gaza because of the U.S.-backed Israeli blockade, American officials are promoting a proposal to establish a new so-called “Gaza Humanitarian Foundation.” Backers of the plan ― which envisions Palestinians gathering small amounts of supplies weekly at “hubs” run by private security contractors ― claim it could deliver aid more efficiently than the United Nations or other relief groups that have operated in Gaza for decades.

HuffPost obtained a pitch for the foundation that avoided placing responsibility for food and resource shortages on Israeli restrictions on aid operations ― a problem independent organizations have documented for 19 months ― and instead highlighted aid diversion by Palestinian militants, which is not seen by most experts as a systemic issue.

Aryeh Lighstone, an adviser to Witkoff, is leading Trump administration discussions about humanitarian issues in Gaza. He does not appear determined to force the implementation of the foundation plan specifically, but he views his role as “neutralizing the crisis as a political issue,” a humanitarian official told HuffPost, requesting anonymity to preserve relationships. Effectively, the official continued, that “means supporting whatever the Israelis are comfortable with regardless of whether it’ll work.” UN officials now believe the U.S. would cut off funding for their operations globally, including the vital World Food Programme, if they do not endorse the proposal.

The plan is deeply controversial both because of fears about its efficacy and the long-standing norm that humanitarian delivery should be impartial, rather than being seen, and possibly rejected by people in need, as part of a strategy by one party in a conflict. A recent UN document warning against the foundation notes that aid groups who work with it may violate international law, since the International Court of Justice has directed governments and organizations not to help Israel’s occupation of the Palestinian territories, and the court is also considering if Israel’s war policy war constitutes genocide.

The Trump team’s thinking is at least different from the views guiding the U.S. for most of the war, in that they do not “take for granted” that Israel is sincere about improving aid delivery, the humanitarian official said.

Given Netanyahu’s dependence on hardline ministers and general Israeli antipathy toward Palestinians, “the Biden administration kept trying to speak to an Israeli enlightened self-interest that is nowhere near what exists in real life,” the official continued. “Meeting with Lightstone is in that way refreshing… he said, ‘Phase 2 [of Witkoff’s Gaza ceasefire] is never going to happen because the Israelis don’t want it to happen.’”

Still, observers doubt the Trump team has either the technical expertise or the political appetite to challenge Israel’s narrative on humanitarian conditions in Gaza and meaningfully ease Palestinian suffering.

“Even if this plan doesn’t move forward, the next plan isn’t more likely to be workable, because it’s all predicated on the false and unsubstantiated claims that our humanitarian system, that has saved and improved countless lives against all odds, is somehow compromised or unworkable,” Scott Paul, the peace and security director at Oxfam America, told HuffPost. “The focus ought to be on what Israel is not allowing: unfettered humanitarian access for us to continue safely delivering lifesaving aid.”

The foundation proposal overlooks key details, Paul noted, by focusing on food and a few non-food goods, while ignoring “the vast majority” of needs among desperate Palestinians, from shelter, sanitation supplies and “everything else people need to survive that can’t be picked up once a week.”

In the U.S., Witkoff may be most intensely scrutinized when it comes to his diplomacy with Iran.

The Trump administration initially seemed poorly suited to handle the dilemma over Iran’s nuclear program, which the president helped worsen in his first term by abandoning a U.S.-negotiated deal to limit Iranian nuclear development in exchange for sanctions relief. Iran has since come far closer to possibly building a nuclear weapon, a prospect U.S. presidents and allies see as inconceivably dangerous, and Israel has said it would use military means to stop.

But four months into Trump’s term, public advocacy for a deal from MAGA loyalists and Iran’s own need for a settlement to boost its economy have boosted expectations Witkoff can reach a compromise.

Meanwhile, critics of “a mutually beneficial deal with Iran” ― including Netanyahu ― have “played their hand very poorly” by demanding any agreement involve a so-called Libya model with a full dismantling of Iran’s nuclear program, said Ali Vaez, an analyst at the International Crisis Group think tank. Demands for such a model with North Korea killed U.S. efforts at a nuclear deal with that country in Trump’s first term, disappointing the president, and Tehran has said it is a nonstarter, suggesting the idea will have to be abandoned if Witkoff’s negotiations are to continue.

Trump has also made a habit of agreements with regional players regardless of Israel’s preferences, said Toossi of the Center for International Policy, like his agreement to halt U.S. strikes on Yemen’s Houthi militia without any promise from them to stop striking Israeli targets in stated solidarity with Palestinians; his talks with Hamas; and his discussion of a nuclear agreement with Saudi Arabia separate from a possible Saudi-Israel deal ― all breaks with U.S. efforts over several years.

Still, Witkoff has yet to develop the kind of broad, sophisticated team that delivered the previous agreement among the U.S., Iran and other governments in 2015. That could give an opportunity to his opponents.

“There’s very little input from different [U.S. government] agencies into his thinking. He is just staffing up and …just started having technical experts joining these conversations; the flow of information and the policy process is all ad hoc,” said Vaez, who recently spoke with Witkoff’s team. “Those who are much more hawkish like Rubio and outside voices still have a chance of trying to influence the administration’s policy direction, because those who are advocates for a deal do not necessarily operate in a systematic fashion.”

Skeptics of Iran have noted that it is in a weak position both financially and strategically, with Israel’s post-Oct. 7 military campaigns weakening its regional allies and Iran’s own defenses. Some members of Witkoff’s staff share the belief that “more pressure could help Iran show more flexibility” in limiting its nuclear capabilities, Vaez said, but “it is possible at some point the administration pushes too far” and dooms the talks, encouraged along by some in Washington since “the process has a lot of enemies.”

Witkoff recently made “maximalist” statements about concessions he seeks from Iran, Toossi noted.

Still, American and Iranian officials, as well as Oman, the mediator between them, made positive remarks about the latest talks on Sunday. And Witkoff has recently hired several career officials who have worked on Iran for years at the State and Energy Departments, Vaez told HuffPost, adding that based on a recent visit to Saudi Arabia, he believes the kingdom, a key Trump ally, is very supportive of a new potential nuclear deal.

The possibility of a negotiated settlement can likely only be sustained if by late June or early July the U.S. and Iran reach even a tentative, small-bore deal to start limiting the nuclear program. Without that in place, other signatories to the 2015 nuclear deal will start to reimpose UN sanctions on Iran given its lack of compliance with the prior agreement ― opening a Pandora’s box of technical problems in continued diplomacy.

The president and his envoy appeal to officials in the Middle Eastern monarchies Trump is visiting this week because of their style, and the sense the U.S. may now be more receptive to partners who had felt frustrated with the previous administration, especially over Gaza.

The men are “emblematic of what Gulf leaders like,” said Aljabri, the commentator on U.S.-Saudi relations. “They’re predictable, they’re transactional, they are strong on deterrence … When you contrast this to the Biden years, it becomes even more pleasing for them as a breath of fresh air after his policy oscillated between empty moralistic rhetoric and pragmatic inertia that really pleased no one.”

Trump has historically embraced quid pro quo diplomacy with repressive foreign rulers and abandoned talk of human rights — habits that trigger alarm bells for many Americans.

But Aljabri, whose father Saad Aljabri was for years a high-ranking Saudi security official whom the first Trump administration described as “a valued partner to the U.S. government,” argued the administration should be assessed based on what it delivers.

Witkoff can “open doors that diplomats couldn’t” because of his record of doing business in the Gulf, he said, also noting that the envoy’s long personal friendship with Trump has created the impression he will retain influence regardless of “whatever attacks he is facing in D.C.”

In terms of progress in the region, Saudi Arabia, the heavyweight among the countries Trump is visiting, is focused on Syria. The country has been ruled since December by Ahmed al-Sharaa — who the U.S. lists as a terrorist over his past militancy. Many U.S. partners in the Middle East and Europe, however, hope he will help the country rebuild after a punishing civil war, to prevent another spiral of bloody chaos and any possible resurgence by figures close to Iran and Russia, the allies of the former Syrian dictator Bashar Assad.

Some foreign policy watchers suspect the new Syrian leader will be in the kingdom while Trump is there, potentially even meeting the president. And this summer presents a looming decision point: Washington must decide by July 6 whether to renew a Biden-era exemption on some sanctions in order to permit interactions with Sharaa’s team.

An intense debate on Sharaa is ongoing within the Trump administration, the Western official told HuffPost.

“You have a group of people very much against any sort of engagement… and who want to increase pressure,” they continued, pointing to Sebastian Gorka, the hard-right counterterrorism director at the White House National Security Council, and Joel Rayburn, Trump’s nominee to run the Middle East office at the State Department. The Israeli government and its allies in Washington also oppose deeper interactions with Sharaa.

Meanwhile, Witkoff and Rubio are open to engaging Damascus. “Witkoff knows Trump wants to expand the Abraham Accords [deals through which the U.S. has encouraged Arab states to recognize Israel] wherever there is an opportunity to deliver that,” the Western official said.

“The main indicator of Saudi leverage will be on Syria policy,” the official continued.

The urgency around Syria is also a result of the kingdom and Trump’s team being similarly aligned on another hotspot in the region: Lebanon. Israel waged a punishing war there last year against Hezbollah, the Lebanese militia aligned with Iran. The U.S. now feels other Lebanese forces are moving “in the right direction” to persuade Hezbollah to disarm even though progress so far “has been slow,” said Randa Slim, a fellow at Johns Hopkins University. The Saudis share that view and, like the Trump team, are not pressing for a quick Israeli withdrawal from the country, the Western official noted.

The driving question of the trip, beyond any single context, is what kind of course it sets for U.S. Middle East policy. Ostensibly, the visit is about business, specifically more than $1 trillion worth of investment in the U.S. But in the Trump era, the intermingling of diplomacy, national-level investments and private enrichment makes for a complex web of motivations ― and worry that corruption could drive decisions rather than rigorous assessments of the best policies.

Witkoff’s own financial ties to the Gulf are significant, and both his family and Trump’s are becoming more entangled with the region’s power player through ventures like a new crypto project backed by the Emiratis and new Trump organization business deals.

The Western official said their government fears the promise of increasing their personal net worths could lead Trump officials to making flawed policy decisions. They noted the Gulf countries have gained major leverage since the first Trump era through growing financial links with the president and his circle even though Europeans “are not ready to play that game.”

“But at the same time …when you see the influence of the Israel lobby in the U.S., I guess the only thing that can balance that out [in terms of Middle East policy-making] is someone willing to play outside the traditional rules and willing to speak the only language that works at the moment in Washington – which is the language of money,” the official said.

They described an optimistic scenario where the general vibe of deal-making produces settlements that calm the region and take into account the security concerns of players from the Israelis to the Saudis. Still, they noted “the other scenario: short-sighted bad deals and making matters worse all over the region.”

“I’m trying to keep an open mind – to not be completely panicked,” the official concluded.