Steve Witkoff: Who is the real estate mogul turned Gaza truce broker?

He has no prior diplomatic experience and no formal government office. Yet, in Donald Trump’s second term, Steve Witkoff, not the Secretary of State or the CIA Director, has emerged as the US president's most trusted emissary on some of the world's most combustible crises.

His journey to the highest levels of American foreign policy began not in the halls of Congress or the Ivy League seminar rooms that typically groom US diplomats, but in a New York City deli at 3 am in 1986.

Ties forged on a ham sandwich

The then-young lawyer working a property deal ran into Donald Trump, who was involved in the transaction but had no cash on him. Witkoff bought him a ham and Swiss sandwich. Eight years passed before their paths crossed again, but Trump hadn’t forgotten the favour.

Over four decades, the businessmen bonded over golf and a shared disdain for bureaucracy. When Trump first entered politics, Witkoff was one of the few from his real estate circle to stand by him. "He’s not just a friend," one Trump insider told CNN. "He’s family."

Witkoff made his fortune through shrewd acquisitions and ambitious real estate developments. He founded the Witkoff Group in the 1990s and amassed a portfolio that included the iconic Park Lane Hotel and the Woolworth Building. By 2019, he had nearly 50 properties across the United States and around the globe.

But it was not his commercial experience that threw him into Trump’s foreign policy world. It was his loyalty.  "Witkoff is a closer," Trump is said to have told aides after a successful hostage negotiation in Gaza. "He knows how to get things done."

The apprentice diplomat

Following Trump’s re-election, Witkoff joined the administration in an informal capacity, initially expected to focus on post-COVID economic revitalisation. But in a private lunch, Witkoff pitched himself for a role in the Middle East, an area where, thanks to business ventures and personal ties, he claimed to have valuable connections.

Congress figures believed it was a long shot, but in Trump’s Washington, proximity often beats protocol. "I was stunned," Senator Lindsey Graham recalled. "I didn’t even know he was interested in the Middle East. But Trump just said, 'Let’s try someone nice and smart.'"

Unlike Jared Kushner, who handled Middle East policy during Trump's first term, Witkoff doesn’t pretend to be a traditional diplomat.

He avoids briefing binders for face-to-face talks and always keeps two notebooks with him, one for general notes, the other for classified information. He rarely holds formal press conferences and often travels with his partner, Lauren Olaya, who serves as a confidante and sounding board.

"He’s an outsider," said Ohio Senator Bernie Moreno. "But that’s why he’s effective. He doesn’t think like the rest of them." But European diplomats are concerned about his lack of policy depth and tendency to speak in business metaphors. "This isn’t a commercial lease," one EU official told US broadcasters. "It’s war and peace."

Iranian leaders, who are on the brink of nuclear deal talks, have also expressed frustration with what one diplomat described as Witkoff's "contradictory and confusing" messages. And Russia, while willing to talk, has shown no signs of making major concessions.

'Riviera of the Middle East' without Gazans

When ceasefire talks between Israel and Hamas stalled in January, Witkoff called Israeli Prime Minister Benjamin Netanyahu’s office from Doha and informed aides that he would be flying in the next day. They reminded him it would be the Sabbath and Netanyahu wouldn’t conduct business.

According to Haaretz, he replied in "salty English" that Shabbat did not concern him. Netanyahu, uncharacteristically, folded. The meeting went ahead. The ceasefire followed.

After visiting Gaza and witnessing Israel's devastation on the enclave, he voiced support for Trump’s radical redevelopment plan to turn the besieged enclave into a "Riviera of the Middle East". The Israeli-backed proposal, which inevitably involves the expulsion without return of millions of Palestinians, was met with international outrage.

Human rights groups called it an ethnic cleansing disguised as economic renewal. Witkoff offered no detailed defence but doubled down on the claim that rebuilding Gaza could only happen under new governance. He said: "If you want peace, you need prosperity. And for prosperity, you need a clean slate."

The second phase of the Gaza ceasefire, which would require Israel to release more Palestinian prisoners and withdraw fully from the Strip, remains in limbo. Netanyahu, under pressure from his far-right coalition allies, has signalled reluctance. Witkoff, however, is pressing ahead.

"Phase two is more difficult," he said recently. "But everybody agrees that getting the hostages out is the right thing. That should be enough."