Trump’s Trusted Confidant Heads to Tehran Talks: Can a Real Estate Mogul Avert a Nuclear Crisis?

In a high-stakes diplomatic gamble, the United States and Iran will return to the negotiating table this Saturday in Oman, with the goal of convincing Tehran to abandon its nuclear ambitions. But in a stunning departure from diplomatic tradition, the U.S. delegation won’t be led by Secretary of State Marco Rubio. Instead, it will be headed by Steve Witkoff—a real estate tycoon, Trump confidant, and the President’s newest foreign policy fixer.
Witkoff, known more for his Manhattan property deals than geopolitical nuance, has become the Trump administration’s go-to emissary for the world’s most volatile conflicts—from Gaza to Ukraine, and now Iran. His appointment has drawn comparisons to Henry Kissinger, though critics point out Kissinger had decades of expertise in international relations, unlike Witkoff, whose diplomatic credentials begin and end with loyalty to Trump.
“He may not know the technicalities of uranium enrichment, but he has the President’s ear—and that matters,” said James Dorsey, a Middle East expert based in Singapore.
Iranian Foreign Affairs Minister Abbas Araghchi will lead Tehran’s team at the talks, where expectations remain low. Negotiators will tackle complex questions over centrifuge counts, enrichment limits, and nuclear site access. Yet the presence of an untested envoy on the American side raises eyebrows.
Witkoff’s personal bond with President Trump is well documented. Their friendship dates back to a 1986 real estate deal in New York and a now-famous “ham and Swiss” lunch Trump forgot to pay for. Since then, Witkoff has become a trusted adviser, major donor, and—now—foreign policy architect.
Despite his lack of experience, Witkoff has made waves. He helped secure a temporary ceasefire between Israel and Hamas in January, which led to hostage releases and a short-lived pause in fighting. That deal collapsed in March, and Witkoff was widely criticized for backing Israeli Prime Minister Benjamin Netanyahu’s aggressive return to war.
In Ukraine, his March ceasefire deal also faltered. Russia insisted on sanctions relief in exchange for a halt to Black Sea combat—a condition Washington refused. Meanwhile, Witkoff drew scorn in Kyiv after parroting Kremlin talking points and failing to name all five Ukrainian regions annexed by Russia in an interview with Tucker Carlson.
Volodymyr Zelensky, Ukraine’s president, accused Witkoff of acting as a mouthpiece for Moscow. Russian President Vladimir Putin, for his part, responded by appointing his own business ally, Kirill Dmitriev, to handle negotiations with the U.S.
That shift has alarmed many observers, particularly after the Biden-era travel ban on Dmitriev was quietly lifted to facilitate talks in Washington.
Now, with Iran, Witkoff faces perhaps his most dangerous assignment yet. The stakes couldn’t be higher. Trump has given the negotiations a strict two-month deadline—threatening military action by the U.S. or Israel if a deal isn’t reached. Tehran, in turn, has warned it will expel international nuclear inspectors if pressured.
Yet some analysts believe conditions are ripe for compromise. Years of sanctions and recent military blows to Iranian proxies have weakened Tehran’s regional posture. Iranian President Masoud Pezeshkian, elected on a mandate to restore economic stability, has signaled readiness to re-engage diplomatically.
Still, the question remains: Can a businessman with a direct line to the Oval Office succeed where seasoned diplomats have failed?
Witkoff’s mission is clear—secure a deal that de-escalates nuclear tensions without reigniting conflict. Whether he has the skill to do so, or simply the proximity to power, may define not only America’s foreign policy but also the future of peace in the Middle East.