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

Witkoff has embraced untraditional tactics and defied some conservatives as the administration seeks quick wins in the Middle East. Now his strategy is being put to the test.

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.