About two weeks after he made international headlines for helping to negotiate a Gaza ceasefire, Steve Witkoff took a break from his globe-trotting schedule on the Upper East Side.
The developer-turned-diplomat joined other dignitaries, including Israeli President Isaac Herzog and Pennsylvania Senator John Fetterman, for the inaugural service at the Altneu shul in late January.
Plenty of familiar faces from his day job in real estate attended the opening of the Manhattan synagogue. There was Ruby Schron, who partnered with Witkoff to buy the landmarked Woolworth Building in 1998 — a deal that helped catapult his career; Len Blavatnik, his partner on the multi-billion-dollar One High Line project in West Chelsea; and Nikki Kushner, who heads Kushner Companies and is sister to Jared Kushner, who held the Middle East envoy position during Trump’s first term.
The day was almost a perfect distillation of the spheres — politics, real estate and Jewish causes — that have made him a central figure, if an unlikely one, in the early days of President Donald Trump’s second administration.
“The thing that really struck me was that he was all in, absolutely committed to giving his all,” Gideon Etra, one of Altneu’s board members, said.
Etra is also in real estate (he’s co-founder of a company focusing on industrial properties) and said he sees parallels between the business and navigating high-stakes agreements with world leaders.
“If you can negotiate all the intricacies of financing a development, zoning and all the competing parts, I think some of the skillset is transferable to solving geopolitical issues,” he opined. “It’s very much a problem-solving ethos.”
Witkoff, 68, with salt-and-pepper hair, appears to have transitioned surprisingly well from dealmaking to foreign affairs — from the luxury condos he’s developing in Miami and New York to now-frequent press scrums outside the White House and spots on Sunday morning talk shows, not to mention negotiations with the world’s roughest leaders.
Where Trump is brash and confrontational, Witkoff is soft-spoken and easygoing. And though bashing Trump is like the local pastime in blue America, it’s hard to find anyone who will say anything personally disparaging about his friend Witkoff.
Witkoff acknowledges his style diverges from Trump’s “swashbuckling ways.” Trump, he told Tucker Carlson in a recent interview, “sets the table in a pretty powerful way” ahead of Witkoff’s diplomacy.
“He predates the kind of newer institutional style of real estate. He’s one of the true dealmakers. There aren’t that many left.”
“This is his ethos, this is how he operates. And so I’m really following him,” he said to Carlson. “Why reinvent the wheel? Why not copy the master?” he said elsewhere in the interview.
Witkoff’s earned a reputation for working out hairy real estate deals. His most important skill, according to people who know him, is finding each stakeholder’s pressure point in order to break an impasse.
In his pre-Trump career Witkoff was a real estate lawyer at Dreyer & Traub, then a landlord with Larry Gluck in the Bronx and Harlem. He’d do maintenance himself — and security, toting a gun in his gym bag. The two built their stature and their networks. Larry eventually became one of the largest rental landlords in New York City. Witkoff got into office buildings, then condos, working on 70 properties altogether.
“He predates the kind of newer institutional style of real estate,” said one New York developer. “He’s one of the true dealmakers. There aren’t that many left.”
But he’s got another skill, too. People — lenders, partners and leaders of friendly and hostile countries — seem to like him.
Around the world
Just after the new year, Witkoff was in Israel to deliver a message: Trump wanted the ceasefire in place by Inauguration Day. To stick to the timeline, the real estate developer with no experience in international politics wanted to sit down with Israeli Prime Minister Benjamin Netanyahu on a Saturday. The leader reportedly refused: It was Shabbat.
“In salty English,” as Middle East Eye put it, Witkoff insisted “on the Saturday face-to-face.” It worked. The two sides hammered out an agreement that would see the release of 33 hostages.
That box checked, Witkoff became a major figure in the Trump administration overnight. He invited New York City Mayor Eric Adams to Trump’s D.C. inauguration, helping to extend an olive branch, and was at Mar-a-Lago when Adams and Trump met to discuss how the White House and Gracie Mansion could work together.
This wasn’t just any overture to a mayor of a hostile city; the Adams situation is fraught with conflict. Not long after the inauguration, Trump’s acting deputy attorney general reportedly reached out to Adams to discuss dropping federal charges accusing the mayor of bribery and soliciting illegal foreign campaign contributions from Turkish nationals.
Then, in February, he spent close to three and a half hours with Russian president Vladimir Putin to discuss the war in Ukraine and the release of American schoolteacher Marc Fogel.
On an episode of “Face the Nation,” he said the main goal of the meeting was to establish rapport.
“To me, the assignment was trust building,” he explained. “I think that President Trump believes — and I believe because he believes it — that trust-building starts with good, proper communication.”
That prompted host Margaret Brennan to note that it was an extraordinary amount of face time with Putin. She asked if Witkoff had any intelligence officers to help.
A wry smirk spread across her guest’s face as he responded. “I had … It was just me.”
Mr. Fix-it
Even among real estate’s high-powered dealmakers, there’s a special reverence held for the fixers. Lenders like a guy who can stop big investments from going bad.
When work stalled at the Steinway Tower on Billionaire’s Row, for example, the project’s group of lenders called Witkoff. He joined as a consultant in about 2021 to help oversee construction of the supertall condo tower at 111 West 57th Street. It opened in 2022.
One of the Steinway lenders, Marc Rowan’s Apollo Global Management, also turned to Witkoff to shepherd construction at 589 Fulton Street, an apartment tower in Downtown Brooklyn after the private equity firm foreclosed on the previous developers.
He also helped straighten out the pair of twisting condo towers over the High Line Park in West Chelsea formerly known as the XI, among the biggest boondoggles in recent memory. He took over what son Alex Witkoff called “a good asset with a bad financial structure.”
Witkoff had an in with the project: He already knew one of the XI’s lenders, Monroe Capital, his partner in Miami on the Shore Club Resort & Residences in Miami Beach.
The XI was in bad shape. The previous developer, Ziel Feldman’s HFZ Capital Group, had paid a lot for the development site and struggled to sell condos when the company imploded under alleged fraud from president Nir Meir. Chicago-based Monroe Capital had lent money to HFZ and had some skin in the game.
Figuring Witkoff could get the project back on track might not have been the only reason Monroe’s CEO, Ted Koening, picked him.
Koenig had first gotten to know Witkoff when his company was interviewing potential partners for Shore Club.
“We talked to all the top developers in town,” he remembered. “Steve wasn’t the biggest; he wasn’t the best capitalized and he wasn’t the most experienced. But I liked him.”
After teaming up in Miami, Witkoff and Monroe took over the XI with Blavatnik, the Ukrainian-born billionaire. They straightened out the capital stack and in August of last year landed a $1.15 billion dollar loan to refinance the project.
The development — now One High Line — passed the $1 billion sales mark last year and is on its way to selling half of its condos.
“Together with Steve we did a nice job of making lemonade out of lemons,” Koening said.
Man of faith
For all his loyalty, Witkoff has only rarely taken a stand for a Trump policy that affected his business.
This was 2018, after he had purchased the 9-million-square foot Fontainebleau in Las Vegas for $600 million two years earlier. Lawsuits and bankruptcy had stalled the project, a money pit, for years following the Great Financial Crisis. When Witkoff picked it up, it was 75 percent complete. He planned to get it across the finish line.
He joined Trump in Las Vegas for a press conference promoting the president’s tax reforms.
In his speech, Witkoff blamed poor GDP growth during the Obama years and said Trump’s policies would change that, resulting in economic growth and 11,000 jobs in Nevada.
“President Trump has changed all of that with the tax reform package and the overall fiscal stimulus that this package represents,” he said. “And we will create a solid investment for ourselves, and thereby make a contribution to U.S. GDP growth because of all of this, and because of the President’s policies.”
“I think that President Trump believes — and I believe because he believes it — that trust-building starts with good, proper communication.”
In other words, the Fontainebleau would get built, thanks to Trump.
Witkoff reportedly struggled to get financing. Construction shut down when Covid hit. And in February 2021, Witkoff and his partners sold the project back to its original developer.
So what does Witkoff want?
By the end of March, a tentative deal for the second phase of the Israel-Gaza truce had fallen apart, and war threatened the region again. Putin said he’d stop attacking Ukrainian energy facilities but did not agree to a 30-day ceasefire the U.S. wanted.
Still, Witkoff was on Fox and Tucker Carlson, talking about his rapport with Russia’s president. On air, he has an ease that transcends his lack of experience. He converses about world leaders and affairs as easily as he would a condo’s capital stack.
Not everyone likes that. After Witkoff discussed Russia on Carlson’s show and in an interview on Fox in late March, the Wall Street Journal’s editorial board fumed about his takes.
“Mr. Witkoff parroted one specious Russian talking point after another,” the editorial went, suggesting he hadn’t found Putin’s pressure points or engaged in his “good, proper communication.”
One High Line wasn’t built in a day, but in real estate, Witkoff had wealth, industry respect and prestige projects, though he has divested his stake in his company to his children, to avoid conflicts of interest, Bloomberg reported.
For years, Witkoff’s loyalty to Trump rested on adoration. “I wanted to be him,” is the kind of thing he says (in this case, to Carlson, about their early days in New York City). But the friendship deepened over the years. The president consoled Witkoff when his son Andrew died of an opioid overdose in 2011, Witoff said at the Republican National Convention last summer.
During an interview with Jared Kushner in February hosted by the Future Investment Initiative Institute in Miami, Witkoff was clearest about why he stepped away from his successful business for the envoy job.
Witkoff said he felt privileged to work for Trump and to do something that makes an impact.
“I’m excited when I wake up in the morning, looking at my texts and my emails,” he said. “It feels very consequential for me.”