People who know Steve Witkoff, Donald Trump’s nominee for envoy to the Middle East, weren’t surprised to hear that a single stern talking to Prime Minister Benjamin Netanyahu convinced him to sign a deal that included a cease-fire and the return of hostages.
"He’s a smart man and a skilled negotiator," said a source close to Witkoff over the weekend. "His usual negotiation style isn’t confrontational—he doesn’t see the other side as an enemy, and he doesn’t look for blood on the floor before closing a deal. But that’s what makes him even more effective when he does come down hard. If you’ve managed to anger Steve, you’re in trouble. There’s no swear word he won’t use."
Donald Trump's pre-inauguration speech, Sunday
Witkoff is a staunch supporter of Israel—and, by extension, of Netanyahu. He attended the prime minister’s speech to Congress last year and called it an "epic speech" when speaking to Republican members of Congress. But his loyalty to Trump is even stronger. Trump referred to him recently as "not a nice guy"—said in the best possible sense. When it came to choosing between taking a softer approach with Netanyahu or following Trump’s instructions, there was no hesitation then, nor will there be any in the future.
Witkoff took on the role previously held by Trump’s son-in-law, Jared Kushner, for the same reasons: loyalty to Trump, and a belief that no problem can’t be solved with a deal. Even the Israeli-Palestinian conflict, in Trump’s eyes, isn’t a centuries-old religious struggle but rather a particularly complicated real estate negotiation.
Witkoff’s flexibility in pursuit of a deal was evident in his collaboration with Joe Biden’s envoy, Brett McGurk. "They had a productive partnership and worked in complete coordination," an American official said. "They didn’t get caught up in politics or rivalries between the two administrations. They had a common goal, and they achieved it."
Trump’s appointment of Witkoff as his Middle East envoy came as no surprise. The two have been close friends since their first meeting in 1986 when Witkoff was a young real estate attorney working at a New York law firm where Trump was a client. They first crossed paths at a deli after working on a joint deal. "Trump didn’t have any cash on him, so I bought him a ham sandwich," Witkoff once recounted.
Witkoff was one of Trump’s most significant fundraisers during his presidential campaign and often served as the man cleaning up Trump’s messes behind the scenes. After Trump insulted Georgia Governor Brian Kemp, Witkoff flew to Atlanta to smooth things over. A few days later, Kemp announced his support for Trump.
When Florida Governor Ron DeSantis dropped out of the primaries, Witkoff mediated a truce between the two. He arranged a breakfast meeting at Trump’s golf club north of Miami, where membership costs over $1 million. By the end of the meal, DeSantis shook hands with Trump and publicly endorsed him.
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Witkoff, 67, is the son of a women’s coat manufacturer, born in the Bronx and raised in Long Island. Trained as a lawyer, he transitioned to real estate in the 1980s. He married Lauren Rappaport, and the couple had three sons: Zach, Alex and Andrew.
In 1997, he founded the Witkoff Group, where his wife and two of his sons also work. Tragically, his youngest son, Andrew, died of an opioid overdose in 2011. Witkoff credits Trump for offering him comfort during that dark time, saying his support brought "real solace in a dark hour."
Compared to the billionaires in Trump’s orbit, Witkoff is considered modest. His net worth is estimated at around $500 million, stemming from his ownership of dozens of properties in London, Miami and New York. He has strong connections in Abu Dhabi and Qatar, whose governments helped finance two major Witkoff Group projects in New York.
Like Trump, Witkoff is a New Yorker who built his fortune in the city, brought his children into the business and then split his time between New York and Florida. As Trump’s envoy to the Middle East, Witkoff’s first priority will always be Trump’s wishes—not necessarily the desires of the people in the region.