How Trump’s Middle East Envoy Pick Became A Billionaire

On Tuesday, Donald Trump watched the sixth test flight of SpaceX’s Starship rocket alongside Elon Musk at the billionaire’s launch site in Brownsville, Texas. The pair were joined by Steve Witkoff, Trump’s longtime friend and a fellow real estate developer.

Witkoff, 67, has been by Trump’s side on the campaign trail for months. When a Secret Service agent assigned to protect Trump fired at a gunman hiding in the shrubs near the sixth hole at the Trump International Golf Club in West Palm Beach in September, he was golfing with Witkoff. A month later, Witkoff spoke at Trump’s Madison Square Garden rally. And in the hectic final day of the campaign, as Trump held rallies in Pennsylvania and Michigan on November 4 before returning home to Mar-a-Lago to watch the results the next day, he was followed again by Witkoff, whose Gulfstream private jet crisscrossed the country in Trump’s tow.

“Our city has drifted away from what it once was, but if there’s one man who can restore it to its greatness, it’s my dear friend president Donald J. Trump,” Witkoff said at the rally in Manhattan in October. “I’ve known the president for over 30 years, not just as a leader, but as a friend.”

In yet another case of the president-elect naming someone from his circle of friends to a position in his new administration, Trump appointed Witkoff co-chairman of his inaugural committee on November 9 and named him as his special envoy to the Middle East four days later. He’s expected to continue the work of Trump’s son-in-law Jared Kushner, who helped negotiate the Abraham Accords between Israel and two Gulf states during Trump’s first term. (Kushner has said he won’t be formally involved in the new administration and will stay focused on his Saudi Arabia-backed private equity firm, which has helped boost his fortune to an estimated $900 million.)

In a press release announcing the appointment, Trump said Witkoff “will be an unrelenting voice for PEACE.” It’s unclear whether Witkoff will need Senate approval—special envoys that work under the State Department have required confirmation votes since January 2023, although president Joe Biden skirted that rule by appointing an envoy as a presidential advisor in the White House instead.

Not only do Witkoff and Trump hail from the same city and the same industry, they are both billionaires. dug into Witkoff’s real estate developments for the first time and now estimates the previously low profile developer to be worth at least $1 billion. That makes him one of at least half a dozen billionaires in Trump’s second administration, though not in the same league as Trump himself ($5.5 billion) or anywhere close to the world’s richest person and Trump’s latest confidante Elon Musk ($318 billion).

His fortune is largely made up of the Witkoff Group, the New York-based real estate developer he founded in 1997. He also owns homes in Manhattan, the Hamptons and south Florida, where he’s developing projects including the Dutchman’s Pipe Golf Club, a Jack Nicklaus-designed course with a luxury hotel, in partnership with Soviet-born billionaire Len Blavatnik’s Access Industries.

“The president-elect has confidence in [Witkoff] as a deal-maker and negotiator and trying to find a way for people who aren’t necessarily seeing eye-to-eye to find a solution,” says Jon Mechanic, a real estate attorney who has represented Witkoff on several deals. “He’s very personable. He’s got some of the same salesmanship qualities as [Trump.]”

The two New York real estate magnates have been close friends since the early 1990s, when Trump was battling bankruptcies at his Atlantic City casinos and Witkoff was snapping up distressed office buildings in Manhattan. That friendship was on display as Trump campaigned for re-election and fought against lawsuits over the past year: Witkoff testified in the New York attorney general’s civil fraud suit against Trump in November 2023 and spoke at the Republican National Convention in July. And it was on Witkoff’s jet that Trump reportedly made his choice to pick J.D. Vance as his vice presidential pick, as the three men flew from Vance’s home in Cincinnati to Palm Beach together.

While Witkoff and Trump haven’t partnered on any real estate deals, they both now live in Florida and are both involved in World Liberty Financial, a crypto project for which Trump takes 75% of the platform’s revenues and Witkoff keeps 12.5%. (Since launching in October, the project has only sold about $20 million worth of tokens out of a goal of $300 million.)

Witkoff built his real estate fortune largely by identifying undervalued properties and raising capital from the same investors over and over again. Recently he’s been focusing on building luxury condos and hotels in New York, Los Angeles and Florida, where he first invested before the post-pandemic boom. Among his most notable holdings are One High Line, a pair of luxury condo towers abutting the High Line park on the west side of Manhattan, and the Shore Club in Miami Beach, which will have 49 condos and a 73-room Auberge hotel when it’s complete in 2027.

Both One High Line and the Shore Club are a testament to Witkoff’s eye for a good deal, according to Mechanic. Witkoff purchased both of them out of foreclosure when the previous developer went bankrupt, found deep-pocketed partners including Blavatnik—plus a $1.2 billion loan from JPMorgan for One High Line—and transformed them into successful condo and hotel projects. One High Line fetched some of the highest-priced residential sales in New York this year, while an oceanfront penthouse at the Shore Club recently went into contract for more than $120 million, making it one of the most expensive homes in Florida.

Longtime New York real estate broker Bob Knakal, who’s known Witkoff since the 1980s, says Witkoff is one of the first people called when there is a big development site available. “A big part of that is being able to see things that other people don’t see, and Steve’s always been very good at that.”

“He’s a very creative real estate guy,” adds Mechanic. “He’s very transactional. He finds an opportunity, fixes what’s broken, and then he creates value. He sells it and moves on to the next thing as opposed to holding it for 50 years.” That’s in contrast to Trump, who has owned his most high-profile properties including Trump Tower for decades.

Witkoff, an avid golfer, has also followed in his friend’s footsteps, betting on golf courses—which have been a bright spot in Trump’s real estate fortune lately and are now worth $1 billion. Besides the Dutchman’s Pipe golf club in West Palm Beach, Witkoff also owns a stake in the Shell Bay Club, a golf course, hotel and condo development located north of Miami in Hallandale Beach, Florida, where memberships now cost $1.5 million—the highest in the country. Between October 2023 and January 2024, the club sold about $100 million worth of condos.

“I could see him holding onto the golf courses long-term because he’s taking a bunch of money out,” adds Mechanic.

Witkoff was born in the Bronx in 1957, the son of a coat maker father and schoolteacher mother, and grew up there before moving to Long Island in the early 1960s. He started out at Union College in Schenectady and later transferred to Hofstra University, where he got a degree in political science and then stayed for law school, graduating in 1983. His first job was at law firm Dreyer & Traub first as a litigator and then in the real estate department.

Trump was a client of the firm at the time. The two men first met in the mid-1980s, at a deli near Dreyer & Traub’s offices in midtown Manhattan, when Witkoff was still an associate and Trump was worth an estimated $600 million. “It had to be 3 in the morning, and I knew who he was. He didn’t know who I was,” recalled Witkoff when he testified on Trump’s behalf in November 2023, recounting how he bought Trump a ham and swiss sandwich because Trump didn’t have any money with him.

By 1985, Witkoff had left Dreyer & Traub for another law firm and started working in real estate on the side, teaming up with his colleague Larry Gluck to buy small residential buildings in northern Manhattan and the Bronx. The pair bought their first property, a 24-unit walk-up in the Inwood neighborhood in northern Manhattan, for $240,000. Each partner had to put in $20,000 for the down payment, with Witkoff financing his cut with a loan from his father—a sum that made up half of all his dad’s cash at the time.

They later sold that property for a $50,000 profit and bought more buildings, ultimately leaving their jobs to start a company named Stellar Management. The two partners hired a crew of 30 people, tending to many repairs themselves. “He famously carried a gun in his sock to collect rents,” adds Knakal.

The next time Trump and Witkoff met was in the early 1990s at a restaurant, where Trump remembered the sandwich incident. The two then struck up a friendship and started golfing and attending Yankees games together. By then, Witkoff had branched out into offices, picking up properties on the cheap during a real estate crash.

He parted ways with Gluck in 1997 to form the Witkoff Group, with Gluck keeping the residential properties and Witkoff taking the offices, including the former New York Daily News building they had purchased for $110 million in 1995. A year after going it alone, Witkoff partnered with fellow developer Ruby Schron to buy the historic Woolworth building in lower Manhattan for $138 million.

Witkoff was riding high, planning to take his company public and bidding on the New Jersey Nets NBA team. But by the fall of 1998, both the IPO and the Nets bid had failed. So Witkoff pivoted. He started buying up offices and converting them to condos in the early 2000s, bringing in partners to lower his downside, at a time when few others were doing so.

“Nobody in New York was doing condos,” says Knakal. “He’s always been ahead of the curve a little bit.”

It’s been a successful strategy, with Witkoff developing multiple luxury condo and hotel properties in Manhattan, Los Angeles and Miami, as well as several apartment buildings. By bringing in outside investors—many of whom have invested with him across multiple deals—Witkoff is able to put in less cash upfront and get out when he’s made a profit, rather than holding the properties for many years. In 2018, he cashed out of the Times Square Edition hotel, selling his stake to his partners in a deal that valued the building at $1.5 billion.

“He took his money, went home, and then when Covid hit, he was no longer there. It wasn’t his issue,” says Mechanic.

It’s unclear how Witkoff’s dealmaking expertise will translate to his new role as envoy. He has no experience in politics or diplomacy, and few ties to the Middle East, besides being a strong backer of Israel. Witkoff, who is Jewish, told online news site the Bulwark that he helped raise “six-figure and seven-figure donations” from Jewish donors to Trump’s campaign earlier this year, after president Biden said in May that he would halt weapons supplies to Israel if it invaded the city of Rafah.

He also has had experience with foreign investors through his real estate business as a prolific user of the EB-5 visa program, which grants permanent residency to foreign investors who contribute at least $1 million to a U.S. business. In 2015, Witkoff raised $229 million from Chinese state-owned firm Taiping Asset Management for a luxury condo project at 111 Murray Street in Manhattan, plus another $175 million for the development through the EB-5 program.

Dealing with foreign investors has also brought some headaches. Witkoff once partnered with Jho Low, the disgraced Malaysian financier who was indicted in absentia in New York in 2018 for allegedly laundering billions of dollars in illegal proceeds from the Malaysian sovereign wealth fund. In 2013, Low agreed to contribute 85% of the $654 million needed to buy the Park Lane hotel in Manhattan, with Witkoff putting in the remaining 15%. Soon after, Abu Dhabi wealth fund Mubadala bought a 30% stake in the project from Low for $135 million.

But by May 2016, Low went into default, and the U.S. government agreed with Witkoff on a plan to sell the hotel. It ultimately took another seven years before the Qatar Investment Authority purchased it for $623 million in August last year. (Low has denied the charges and reached a $700 million settlement with the Department of Justice in 2019.)

While he’s working for Trump, he’ll leave his firm in the hands of his son Alex, 32, who is already the firm’s co-CEO; his wife Lauren and another son, Zach, are executive vice presidents.

He’ll likely need them to take charge so he has few distractions. Working to implement Trump’s plans in the Middle East won’t be easy. More than a year after Hamas’ October 7th attacks, the war has spread to multiple countries and Trump’s first-term dream of a normalization deal between Israel and Saudi Arabia seems as distant as ever.

“What he’s best at is finding something that’s broken and fixing it,” says Mechanic. “Let’s see if he can take that skillset on the road to the Middle East and come back with a solution.”