How a real estate mogul became Trump’s Middle East point man

But that Palm Beach party, in April 2022, was also something else: an extravagant reminder of the distance that the groom’s father, Steven Witkoff, had traveled over his nearly seven decades. From his boyhood in the Bronx, Witkoff ascended to the peak of the real-estate business in New York and Florida, and along the way secured a privileged place in Donald Trump’s court.

Paying tribute that evening were the former president and first lady, who stayed late into the night to celebrate. Also on hand: Florida Gov. Ron DeSantis, a collection of real estate royalty, including Barry Sternlicht, and the baseball star Alex Rodriguez.

Elon Musk may be Trump’s most visible new “bestie" since throwing his weight and money behind the president-elect’s campaign, but Witkoff has been one of Trump’s closest and most constant friends on his climb back to power. Witkoff traveled with Trump throughout his campaign and stayed with him at Mar-a-Lago in the week leading up to election day. Witkoff was golfing with Trump on the day of an attempted assassination in September.

Now Trump has tapped his old friend for a substantial role in setting U.S. foreign policy: as Middle East Envoy, the high-profile post held by Trump’s son-in-law, Jared Kushner, during his first term.

The appointment of another developer—as opposed to a diplomat—deepens the sense that Trump ultimately views the Middle East crisis as a complicated property negotiation. Witkoff shares that view, seeing it in part as “one giant real estate deal," according to a person familiar with his thinking. And choosing someone so close to the family, say insiders, means Witkoff should be able to have some continuity with Kushner’s approach.

Like Trump, Witkoff is a quintessential New Yorker who made his fortune in the city, brought his kids into the business, and then, at a certain age, relocated to South Florida. Also like Trump, he is an avid golfer. Peers in the real-estate world invariably describe Witkoff, 67, as smart, personable and a talented negotiator with a common touch.

“His negotiating style was one where it was never adversarial," said Don Peebles, another well-known developer who attended the Mar-a-Lago wedding, recalling their first dealings years ago. Witkoff is “not the kind of negotiator that wants to see blood on the floor before getting the deal done."

Whether he has grasped the tangled history and nuance of the Middle East is another question.

Witkoff, who is Jewish, has been a staunch supporter of Israel. Although he has no diplomatic training, friends point to the business contacts he has built up in the region. Last year Witkoff sold Manhattan’s Park Lane Hotel to the Qatari Investment Authority, the country’s sovereign-wealth fund, for $623mn. Abu Dhabi’s investment fund was also involved.

“He’s very self-aware about what he knows and he doesn’t know," said Marty Edelman, a Paul Hastings real estate lawyer, who described his friend as someone able to “understand both the Rubik’s Cube and the people who are turning it."

Still, another real-estate executive sounded skeptical about Witkoff’s credentials even while praising his savvy. Peacemaking in the Middle East isn’t Witkoff’s world, this person said.

In addition to the sensitivities of the region, Witkoff may also have to finesse relationships closer to home. Kushner has indicated that he expects to remain involved—even without an official role. “I’ll give them my advice, I’ll help them in any way they need," he told The Wall Street Journal in a recent interview.

Witkoff plans to “speak with, collaborate and download with" Kushner, whom he believes has an “exceptional grasp of the dynamics" of the region, said a personal familiar with this thinking.

Many foreign-policy professionals were aghast at Kushner’s own appointment.

Yet Trump’s son-in-law managed to seal the Abraham Accords, in which several Arab countries normalized relations with Israel. Its momentum has since been halted by Hamas’ attack on Israel, and the resulting war in Gaza.

Kushner also demonstrated the job’s commercial possibilities. Upon leaving office, he received a $2bn investment from Saudi Arabia for a new private-equity fund. Another $1 billion came from the United Arab Emirates and Qatar.

Direct line to Trump

What’s certain is that Witkoff will have Trump’s ear. The two first met in 1986 when Witkoff, then a young real estate lawyer, worked for a law firm, Dreyer & Traub, where Trump was a client.

The basis of their friendship was a sandwich, according to Witkoff’s testimony last year on Trump’s behalf in a fraud suit brought by the New York attorney general. They had bumped into each other in a deli after working on a deal together. Trump didn’t have any cash so “I ordered him a ham and Swiss," Witkoff testified.

Trump, according to Witkoff’s son, Alex, was “one of the big inspirations" who prompted his father to make the leap from lawyer to developer.

The relationship has deepened over the years, with Steve Witkoff praising Trump’s steadfastness after Witkoff’s son, Andrew, died of an opioid overdose in 2011. “His presence brought real solace in a dark hour," Witkoff said during his address at this year’s Republican National Convention, calling Trump “as kind and compassionate a man as I’ve ever met in my lifetime."

As president, Trump invited Witkoff to speak about Andrew at a conference on the opioid epidemic he and the first lady hosted.

Witkoff, in turn, came to Trump’s aid during the Manhattan fraud trial. He was the first to testify in his friend’s defense, and did so at a time when many previous supporters and donors were distancing themselves.

During the last week of the campaign one of Witkoff’s real estate partners reached out, asking when he would see him again. Witkoff, according to this person, declared: “I will stay with the president for the duration." On the night of Trump’s victory, he was among the tight circle of family and friends called to the stage to celebrate.

Yet most of his work for Trump has been out of the spotlight. Witkoff has been one of Trump’s biggest fundraisers—providing a link to Jewish donors, including Miriam Adelson, a staunch supporter of Israel who ultimately contributed $100mn—and a regular companion on the campaign trail.

He has also played cleanup man. After Trump insulted Georgia Gov. Brian Kemp at a rally, for example, Witkoff flew to Atlanta to smooth things over. Days later, Kemp went on Fox news to pledge his allegiance to Trump.

And when DeSantis bowed out of the race, Witkoff brokered a detente between the protege-turned challenger and Trump.

Witkoff brought them together in April for breakfast at his Shell Bay Club in Hallandale, Fla., where golf memberships go for more than $1 million. It is the place where Witkoff plays gin with pals and holds court. The chef, Julien Jouhannaud, is from Le Bilboquet, the Upper East Side French restaurant in which Witkoff is a part owner.

“It’s like his Mar-a-Lago—only much nicer," said one person who has visited.

He also wooed Nikki Haley, the last of Trump’s challengers in the Republican field. In her podcast, Haley recounted how Witkoff traveled to her home in South Carolina to negotiate a “truce," and asked what Trump could do for her. “There’s nothing I want," said Haley, who endorsed Trump, but never fully embraced him.

Landlord to diplomat

It is a far cry from his early days as a developer when Witkoff, the son of a coat maker, and another Dreyer & Traub lawyer, Laurence Gluck, scoured 1980s Harlem and the Bronx for tenement buildings as a kind of side hustle. They named their company Stellar—a mashup of ‘Steve’ and ‘Larry’.

Operating such low-rent properties with tight margins taught him the importance, he has said, of overseeing the maintenance himself. When introducing him at the RNC, Zach Witkoff recalled his father leaving a New Year’s Eve dinner one year to fix a broken sewer tank in Harlem with “a bear of a man named ‘Shecky.’ You see, they couldn’t afford a crew. They were the crew."

A less savory detail from those days is that Witkoff sometimes carried a revolver in an ankle-holster—presumably to protect himself while operating in rough neighborhoods.

The partners eventually split and while Gluck stuck to residential properties Witkoff began snapping up New York office buildings that had come on the market at deep discounts in the aftermath of the late 1980s real estate crash. One of his first purchases was 156 Williams Street, in the financial district, for a mere $20 a square foot.

Witkoff’s early loans came from Buffalo’s M & T bank. When he exhausted their appetite he moved on to Credit Suisse First Boston, and then Lehman Brothers.

(In a 1998 Journal article, a Lehman banker downplayed concerns that it might be overexposed after lending more than $750mn to Witkoff. Much of that had been sold on to investors as mortgage-backed securities, the banker explained).

Witkoff was no longer living the life of a toiling landlord. He spent nights with Bo Dietl, the former New York police detective, at Rao’s, the clubby Italian restaurant known for being almost impossible to get into. He moved on from financial district buildings to hunt for trophies, including the Daily News and Woolworth buildings. He even took a shot at the Chrysler Building, which ultimately went to Jerry Speyer of Tishman Speyer.

By the end of the decade, speculation cropped up that Witkoff was overextended, especially after plans for a public offering were dashed. He managed to work himself out of it.

In recent years, the Witkoff Group has profited from the South Florida boom with projects like Shell Bay north of Miami. It has developed close relationships with private-equity firms, including Blackstone and Apollo, and a reputation for executing where other developers have stumbled.

One of its current projects is the ultraluxury Shore Club in Miami’s South Beach, where a penthouse earlier this year went under contract for more than $120mn. Witkoff scooped up the property and then revised the plans after another developer, HFZ, went bust. He has employed a similar playbook at One High Line in New York City, also an HFZ castoff.

The $2 billion project, originally known as XI, looked like an expensive failure. After buying it out of distress, Witkoff changed the name and overhauled the architectural plans. Sales have been brisk, according to Pamela Liebman, chief executive of real estate agency The Corcoran Group, who has worked with Witkoff for more than 20 years and is a member of his golf club.

“He changed the narrative," she said.

Write to Joshua Chaffin at joshua.chaffin@wsj.com and Deborah Acosta at deborah.acosta@wsj.com