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I remember first seeing Steve Witkoff in person in May 2024, when he was spending a disproportionate amount of time in a criminal courtroom in Lower Manhattan that had seen better days. Like many of us, he was there to watch then-former President Donald Trump stand trial on 34 counts of falsifying business records in the first degree, in the so-called hush money trial. Witkoff sat in a row of hard wooden benches often occupied by people aiming to make public displays of support for Trump—J.D. Vance, Douglas Burgum, Pam Bondi—who were then all vying for the vice presidency or the Cabinet. Donald Trump Jr. attended, as did Eric Trump and his wife Lara, who was then co-chair of the Republican National Committee.
For the Trump VIPs, being seen by both the packed rows of reporters with coveted courtroom passes and Trump himself was a key part of the ritual. Each day, there was a little flurry of figuring out who had come to watch. To the side of all of this was Witkoff. He is short compared to Trump, his hair gray. He looks like a grandpa, and sounds a little like a Jewish sidekick in a Pixar movie. I’d known of him as a New York real estate mogul from covering Trump’s first presidency, and New York politics and real estate before that, but only vaguely.
One day, I leaned forward to ask Witkoff what brought him to the courtroom that day. He told me he’d come for his friend. That word stuck with me: friend.
In New York, former employees and real estate execs and politicians and people in Trump’s orbit have told me again and again that Trump doesn’t really have friends. He has his family, and also a rotating cast of people who are in his favor at any given moment. And then there is Witkoff, who turned up on even the days that were supposed to be dull, like May 30, 2024, when the jury wasn’t expected to reach a verdict but then, suddenly, did.
After the jury foreman, when asked “How say you?” answered “Guilty,” 34 times, Trump turned to face the back of the room, looking uncharacteristically stricken. He grabbed his son Eric’s hand to shake it and walked out to trash the judge and the proceedings, which he’d soon appeal. Behind him, to the right, barely visible, was Witkoff.
Then Trump’s entourage left in a convoy of black SUVs headed for a Midtown fundraiser, where Trump raised $50 million for his campaign. Neck and neck with Joe Biden in the polls, Trump’s campaign needed the money. What’s more: Beset with legal bills, he’d been pressed to come up with the cash for three civil judgments against him, and now was convicted of 34 felonies.
Exactly two years and one month later, in the miasma of a baking afternoon just days before the July Fourth weekend, we all would learn how astonishingly successful President Donald J. Trump has been in his moneymaking endeavors. The White House released Form 278e, his annual ethics disclosure, a normally nerds-only affair. Biden’s final disclosure was 11 pages long. Trump’s was 927 pages, up from 234 last year.
Everything else about it was bigger too, most astonishingly the bottom line revealed by the document. In 2025, Trump made at least $2.2 billion while also serving as president, making it arguably his most profitable year ever. Even the notoriously conservative Wall Street Journal editorial page was upset with Trump and his family. “They are profiting off the Presidency in ways that demean the office,” it declared. (In an emailed statement, White House spokesperson Anna Kelly said: “All of the President’s assets are held in fully discretionary accounts managed by independent third-party financial institutions. There are no conflicts of interest.”)
The biggest chunk of Trump’s 2025 haul came from his recently founded cryptocurrency enterprise, World Liberty Financial. This was the venture he had set up just before the 2024 election with his three sons—and with Steve Witkoff and his two sons. Witkoff’s son Zach is currently the company’s CEO.
Today, Witkoff is Trump’s “Special Envoy for Peace Missions” in the world’s hottest hot spots.
On the surface, Witkoff seems like Trump, a New York real estate developer turned world dealmaker. But in an administration that privileges snarling visages, Witkoff is nearly universally described as “kind,” or “nice,” a quality he has used to good diplomatic effect.
He is currently involved with the tattered negotiations with Iran, when he is not meeting with Ukrainian President Volodymyr Zelensky or sitting across the table from Russian President Vladimir Putin, or their emissaries, like Kirill Dmitriev, who runs the Russian sovereign wealth fund—a giant pool of money that can be spent to advance Putin’s priorities. Once, diplomatic counterparts who controlled huge sums were regarded warily by U.S. diplomats. But for Witkoff, like his boss, they are like magnetite.
As Witkoff presided over a tenuous ceasefire deal with Hamas and Israel, he surrounded those talks with meetings with big-name Gulf leaders, like Saudi Crown Prince Mohammed bin Salman, and Emirati Sheikh Tahnoon bin Zayed Al Nahyan. Tahnoon—who oversees the United Arab Emirates’ sprawling spying operation and has been called the “Spy Sheikh”—is brother to the Emirati president, that country’s national security adviser, and controls, according to the Wall Street Journal, “more money than almost anyone on the planet,” an estimated $1.4 trillion.
It is no accident that Witkoff’s counterparts, such as Dmitriev and Tahnoon, are—like Witkoff—extremely tight with their countries’ leaders, deeply implicated in foreign negotiations, and steeped in an image of the world as a set of business transactions. Donald Trump has created a new operating system for U.S. foreign policy, one with business deals at the center, one from which he and his family profit, and one that relies in large part on his trusted friend Steve Witkoff to pull off. When asked about this, the White House said in an email, “The center of the President’s foreign policy is ‘America First.’ ”
Last year, for example, at his Miami waterfront estate, Witkoff hammered out a plan with Russia’s Dmitriev for $300 billion in joint Russia–U.S. investment projects—which would come to fruition after some possible future peace. Russia, Ukraine, and the U.S. could all become business partners, Witkoff told the Wall Street Journal, which has broken a stunning series of stories on the envoy: “If we do all that, and everybody’s prospering and they’re all a part of it, and there’s upside for everybody, that’s going to naturally be a bulwark against future conflicts there. Because everybody’s thriving.”
With the UAE, such relationships have moved far beyond the hypothetical. For the entire first year of the Trump administration, the “Spy Sheikh” was a secret 49 percent equity partner in World Liberty Financial, a deal worth hundreds of millions of dollars to the Trump and Witkoff families. This was while the sheikh wanted the Trump administration’s approval for access to sensitive A.I. chips. Which he got. (The UAE Embassy did not respond to requests for comment. The White House, responding on behalf of Witkoff, said that he was not involved in the chip negotiations. World Liberty did not respond to detailed questions but has said that Trump and Steve Witkoff were not involved in the deal for the equity stake.)
There’s more: In the early days of the Trump administration, Zach Witkoff negotiated a business deal where a Tahnoon-led firm deposited $2 billion into World Liberty, rocketing the currency to superstar status in the crypto world. All these transactions took place before Steve Witkoff had fully divested from World Liberty, his own disclosure form shows.
On the World Liberty “Gold Paper,” a document describing the company for potential investors, Witkoff and Trump are each listed as “co-founder emeritus.” “Even if legitimately neither Trump nor Witkoff are involved hands-on in any of the crypto activity, they see the money come in,” Corey Frayer, the senior adviser on crypto at Biden’s Securities and Exchange Commission, told me.
The White House scoffed at this. “All of the President’s assets are held in fully discretionary accounts managed by independent third-party financial institutions. Special Envoy Witkoff has divested from World Liberty Financial,” Kelly said in a statement. But Frayer says the baked-in business model of World Liberty Financial is paying money to be close to the president, with Steve Witkoff playing the functional, if not literal, role of what Frayer calls “chief salesman.”
The White House said, of Frayer, that he “is not involved in the United States’ diplomatic discussions and has no idea what they are talking about.”
To be sure, Witkoff has amassed enormous power, visible in his proximity to the president. To understand how he did that, I spoke with dozens of former Clinton, Bush, Obama, Biden, and Trump administration officials, as well as academics, cryptocurrency and foreign policy experts, real estate moguls, and politicians. Many did not want to speak at all; one developer mistakenly sent me an email that said, “Steer clear..do not want to engage.” The White House did not make Witkoff available for an interview, despite repeated requests over the course of more than a month, but partially answered via email a list of fact-checking questions and requests for comment, and at the last minute sent over glowing tributes from Secretary of State Marco Rubio and various senators and members of Congress. (Rubio referred to their “strong working relationship.”)
Crucially, the White House denied there were any conflicts of interest. “Mr. Witkoff, like all Administration officials, takes seriously his compliance with the government ethics rules,” the White House counsel, David Warrington, said in the email. “As Special Envoy for Peace Missions, he has not and does not participate in any official matters that could impact his financial interests. He has also divested from World Liberty Financial, notwithstanding his ability and willingness to recuse.”
Forty years ago, back in the 1980s, Steve Witkoff was a junior lawyer at a firm working for Donald Trump, and was watching him keenly. “He’d come to 101 Park Avenue, where I was a lawyer. He had this swashbuckling style,” Witkoff told a surprised Tucker Carlson on an early-2025 appearance on Carlson’s podcast. “And I used to say, ‘Well, God, I want to be him. I don’t want to be the lawyer. I don’t want to be the scrivener.’ ”
This is when Witkoff spontaneously—and fatefully—bought Trump a sandwich that changed everything. “It had to be 3 in the morning, those were the days of those crazy hours,” Witkoff testified at Trump’s 2023 New York civil trial for a decadeslong scheme of lying about his property values. (Trump was ordered to pay $355 million, plus interest, but the amount was thrown out by an appeals court that found it “excessive.” The fraud ruling stands, though; Trump is appealing that too.)
“And he was—I knew who he was. He didn’t know who I was. And he didn’t have any money with him and I was ordering from a local delicatessen for the people who were on my team. And he asked me if I would order him a ham-and-Swiss sandwich.” Witkoff did. Years later, when the two ran into each other again, Witkoff said, “he actually remembered who I was, and remembered the sandwich incident. And we just, you know, had just developed a, you know, a friendship as a result of it.”
Witkoff quit his firm and became a developer, first of what weren’t very sexy buildings in Upper Manhattan and the Bronx. He carried a gun strapped to his sock to collect rent and fixed sewage systems himself when they broke down. He slowly built credibility—unlike many in dynastic New York real estate, he was the son of a coat manufacturer—and eventually acquired local landmarks like the Woolworth Building, once the city’s tallest skyscraper, and the Daily News Building, the model for the “Daily Planet” in Superman movies. By the 1990s, with his investments in more elegant buildings downtown, he was playing golf with Trump, and their families hung out together.
“I’ve known Steve for 40 years, and he’s been with me, more or less, one way or the other, every step of the way,” Trump said at Witkoff’s Oval Office swearing-in, in May 2025. But there is little in the public record to document this, other than items in the gossip pages about their golf bouts. Even Witkoff’s friends can’t pin down how the two became so close. Real estate lawyer John Mechanic, a Witkoff partisan, told me—twice—that Witkoff was such a talented dealmaker he could “sell ice to an Eskimo.” Mechanic remembered a party sometime pre-presidency for Witkoff’s wife, Lauren, when Trump was beamed in via video with a birthday greeting, but he couldn’t place when that was. (Witkoff and his wife are separated.)
In 2011, Trump attended the memorial service for Witkoff’s oldest son, Andrew, who tragically died after overdosing on oxycontin. This was shocking news even to people who knew both Trump and Witkoff. “HE DID?” one New York politico exclaimed when I asked him about Trump’s attending the memorial. In New York real estate circles, Trump simply is not known for doing anything for anyone other than himself. But Trump calls Witkoff a “great friend of mine.”
As a sign of his growing skin in the game over the years, Witkoff made political donations in the manner of New York developers (including, in a past life, Trump himself) to whatever party in power could affect their fortunes by getting behind tax abatements, zoning variances, or environmental rules. That means he’s donated to a range that spans from Republican Gov. George Pataki to Sens. Hillary Clinton and Chuck Schumer, and once, even, the ultraprogressive Working Families Party.
In 2016, Witkoff’s donation pattern changed: Big sums were going, almost exclusively, to Trump and the Republican Party. In Trump’s first administration, Witkoff was appointed to the Kennedy Center board, attended a White House opioid summit, and defended Trump on TV, including in 2017, telling Bloomberg television: “I never understood the Russian sanctions, candidly, because all it did was stop Russian investment into this country. And I happen to agree with him that Russia is a natural ally in the fight against global terrorism. And why? Because they have an indigenous population of 30 million Muslims, and I have to believe that he and his administration understand that.”
Still, Witkoff did not appear to be in Trump’s inner circle during his first term. His name was not on a contact list introduced as evidence in Trump’s criminal trial, which was, according to testimony of a former White House aide, “for people that he either spoke to often or might want to speak to.” Other New York real estate executives were on it, along with Tom Brady, Joe Scarborough, Michael Cohen, National Enquirer publisher David Pecker, Trump Organization CFO Allen Weisselberg, and Trump’s (now late) sister Maryanne Trump Barry, a judge on the 3rd U.S. Circuit Court of Appeals.
But after the attack on the Capitol on Jan. 6, as others distanced themselves from Trump, Witkoff remained staunchly loyal: As Trump’s orbit slowly tightened, the relationship strengthened. Zach Witkoff, the son who would later become instrumental in Trump’s presidential wealth-building, was married at Mar-a-Lago in 2022, with the Trumps in attendance. (Zach later named his son Don.) The year before Trump’s reelection, Trump and Steve Witkoff bonded especially tightly. Witkoff made his private jet available to Trump’s campaign, donated buckets of money, and raised even more—including, notably, from American Jews enraged by Biden’s moratorium on selling Israel 2,000-pound bombs.
Witkoff became one of the people who traveled with Trump, showing up not only in courtrooms but seemingly at every important event. J.D. Vance rode Witkoff’s jet to his VP interview with Trump at Mar-a-Lago. Joined by Zach, Witkoff spoke in the run-up to Trump’s acceptance speech on the all-important fourth night of the Republican National Convention. Witkoff appeared at the infamous Madison Square Garden rally at which one speaker called Puerto Rico a “floating island of garbage.”
And the friends solidified their bond—they went into business together. And not just any business, but a perfectly Trumpian business: cryptocurrency.
In his first term, Donald Trump had tweeted, “I am not a fan of Bitcoin and other Cryptocurrencies, which are not money, and whose value is highly volatile and based on thin air. Unregulated Crypto Assets can facilitate unlawful behavior, including drug trade and other illegal activity.”
But by 2024, Trump had made a complete reversal. He showed up at the “Bitcoin 2024” conference, promising a new age in government regulation of the currency. And by “new age of regulation,” he meant there would be next to none. He promised to make the U.S. “the crypto capital of the planet and Bitcoin superpower of the world.” His biggest applause line was that he would fire Gary Gensler, the head of the Securities and Exchange Commission. The cheering was wild, and sustained.
Money sluiced into Trump’s campaign from the crypto world and, soon, directly into Trump’s and Witkoff’s own pockets. “We’re on the verge of something game-changing in Crypto and DeFi,” Steve Witkoff tweeted in early August 2024. He added: “Bringing financial power and freedom back to the people—get ready. #BeDeFiant.” The word DeFiant was a coy wink to this idea of decentralized currency, known as DeFi, the ostensible rationale for the new Trump–Witkoff platform. The plan was for a currency exchange, somewhat like a bank, but that could be floated with anonymous investments and operate without the strictures of regular banks.
In the middle of all of this, on Sept. 15, 2024, Witkoff, Trump’s “golf partner,” as he was referred to then, was approaching the fifth hole with the presidential candidate at Trump International Golf Club in West Palm Beach when he heard the first shot. “I’m a gun carrier, so I shoot, so it’s apparent what that was,” Witkoff told CNN. He remained standing as three more shots rang out, and Secret Service agents hustled the candidate off the course. Trump had survived a second assassination attempt in the span of three months.
The next day, Witkoff was again with Trump, and Don Jr. and Eric Trump, in a shambolic livestreamed announcement of their new crypto venture: World Liberty Financial. Zach and Alex Witkoff were on the founding team, and Zach would run the company. Even Trump’s youngest son, then a first-year student at New York University, was part of the group. Barron Trump was named as the company’s “DeFi visionary.”
In the roar of the final weeks of the presidential campaign, the launch barely registered. However, the Biden SEC certainly noticed. High-level officials there immediately viewed the firm as selling proximity to a potential president, two of them told me. There was a sharp intake of breath, and research began on what, if anything, the regulatory agency should do. “Even if no one said it outright, we were all thinking that if WLF is what it looks like, bringing an enforcement action against Trump would be both necessary and a nightmare,” said Corey Frayer, the crypto expert at the SEC at the time. Then the clock ran out.
“E-Moluments,” American University law professor Hilary Allen calls it. It’s a play on the word emolument, a gift from a foreign leader or domestic government that a president is prohibited under the Constitution from accepting. During the first Trump administration, countries like Saudi Arabia lined up to book rooms at the Trump International Hotel in Washington and other Trump properties. But with crypto, Allen told me, Trump “has found a way to get rid of the hotel and create an infinite number of rooms.”
Trump hadn’t yet won the election, but during this period, while he was promoting World Liberty for his friend and business partner, Witkoff was also debriefing with Jared Kushner about Kushner’s work as senior adviser during Trump’s first term negotiating the Abraham Accords, a series of agreements aimed at normalizing relations between Israel and several Arab countries. Trump “asked Special Envoy Witkoff what he wanted to do in the second administration,” a source familiar with the transition said. Witkoff said he wanted to be the “peace guy.”
But even as he was preparing for that role, he kept up his business activities. As late as Halloween 2024, Witkoff was promoting Bitcoin on X. Not two weeks later, the campaign over and victory secured, Trump named Witkoff “Special Envoy to the Middle East.” (His title was updated on June 30 of last year to “Special Envoy for Peace Missions.”)
Witkoff did not wait until the inauguration to get started—he immediately began working on a Gaza ceasefire alongside Biden officials, a role some experienced diplomats cautiously praised. “I didn’t start with a negative view,” Robert Malley, a high-level negotiator under Bill Clinton, Barack Obama, and Joe Biden, told me. “Certainly in the Middle East, the line between private and public affairs can be pretty tenuous, so one could see how having the kinds of ties Witkoff enjoyed could build a relationship, if not of trust, then at least of familiarity.”
Malley added: “Early on, a number of Gulf countries seemed quite elated. They knew him well. They thought he understood them because he had dealt with them on the business side, and because he enjoyed the president’s trust.” Both Abu Dhabi and Qatar had helped Witkoff out with a troubled deal involving a Park Avenue hotel, and, Malley said, Mideast nations “were quite happy to have someone with the ear of the president who knew them extremely well.”
Soon after the election, Witkoff was in the United Arab Emirates. Axios reported he met with Tahnoon, the “Spy Sheikh,” and “discussed the war in Gaza, the turmoil in Syria and other regional issues.” Even in real time, when so much was not known, it was reported that Witkoff was mixing business and diplomacy. Witkoff, the New York Times noted in December 2024, had “already started to work on trying to negotiate a new peace deal in the region, but he also is simultaneously promoting World Liberty Financial, which the Witkoff and Trump families helped create this year.” (The White House denied that Witkoff ever discussed World Liberty Financial with Tahnoon.)
The next month, an employee of a Tahnoon company went to work for World Liberty as “Chief Strategic Advisor,” a position he held simultaneously with “Head of Crypto and Blockchain” at the Tahnoon-controlled company G-42, his LinkedIn page shows, as first reported in the Pulitzer Prize–winning series by the Times.
Witkoff was doing something else during this period: He was co-chair of Trump’s presidential inauguration committee, which was raising an unprecedented amount of money, nearly a quarter of a billion dollars, doubling Trump’s record-setting 2017 haul, and quadrupling President Joe Biden’s 2021 inaugural fundraising. According to an analysis by the Brennan Center for Justice, the majority of money raised came in chunks of $1 million or more; these donations by themselves surpassed the size of all previous inaugural funds in total. The technology industry led, with nearly $50 million in donations, almost matching the entirety of funds raised by President Barack Obama in 2009. Then came finance, then came energy, followed by healthcare. Cryptocurrency, at $13.5 million, was enough to make it one of the top five donor industries.
At Trump’s swearing-in, Witkoff proved his friend status. He stood as close to the president as anyone not named Trump.
At the start of the second Trump administration, World Liberty almost immediately started to benefit.
On his first full day in office, President Donald Trump’s SEC set up a crypto task force, which right away began deregulating. The SEC and Justice Department dropped or settled cases with key World Liberty investors and partners. Trump gave “A FULL AND UNCONDITIONAL PARDON” to Changpeng Zhao, or CZ, as he’s known, the founder of Binance, who had already served a jail term for allowing “money to flow to terrorists, cybercriminals, and child abusers,” according to former Treasury Secretary Janet Yellen in a 2023 press release. Overreach, the Trump team called it. By the time of CZ’s pardon, Tahnoon’s firm had already used Trump’s cryptocurrency to invest $2 billion in Binance, a move that buoyed the Trump–Witkoff family crypto venture.
This January, WLF applied for a bank charter to the Office of the Comptroller of the Currency, part of the Treasury Department. Of five proposed directors named in WLF’s proposal, two are named Witkoff: Zachary Witkoff and Robert Witkoff, who is Steve Witkoff’s brother. Getting such a charter would give huge latitude to crypto banks, endangering unsophisticated investors, critics say. “Charters are only awarded on a case-by-case basis in alignment with statutory and supervisory criteria,” White House spokesperson Anna Kelly said.
As with everywhere in his government, Trump and his top aides have seen to it that these little-known offices are run by loyalists. “The mere prospect there could be a call is enough to chill agency heads,” Graham Steele, a former Treasury assistant secretary for financial institutions, told me. “You take the obscure office of the Treasury to which World Liberty has applied: If they deny the application, you can assume that person will lose their job. It’s obvious on its face.”
“President Trump proudly made the United States the crypto capital of the world through executive actions, supporting legislation like the GENIUS Act, and other commonsense policies to drive innovation and economic opportunity for all Americans,” Kelly said.
Like Trump, Witkoff is unabashed about performing diplomacy through a business lens. In the Trump administration, this isn’t something to be ashamed of. It’s something to boast about. Because, like Trump’s hype his entire career, one deal, successful or not, begets another.
“The traditional models of diplomacy have resulted in duplicative or even contradictory foreign policy actions,” Kelly said in an email. “The President wants the United States to be treated fairly and he has prioritized using foreign policy to enhance domestic economic prosperity.”
Unlike the president, who is exempt from conflict-of-interest laws, Witkoff is not supposed to be doing business while working as a White House employee. The White House says he has divested from World Liberty and follows all applicable laws. And while Forbes reports that Witkoff’s net worth increased by $300 million while working in the White House, largely due to his investments in World Liberty, no evidence has emerged that Witkoff has sought out such a benefit.
Divestment or no, the upshot is that Zach Witkoff runs a company that is in a position to reap wide benefits from the administration for which his father works, for himself and for the Trump family. In fact, he has already done so, and leaders around the world know this, and seemingly behave accordingly.
“International actors understand there are benefits if they go into business with quasi-public actors,” added Steele, who worked in the Biden Treasury Department until January 2024. “No one needs to say it, it’s just clear.”
Zach Witkoff did not respond to dozens of questions about his father, the Trumps, or World Liberty. But a spokesperson for World Liberty said in a statement: “World Liberty Financial is one of the most successful financial technology companies in the United States. Among its products is USD1, a fully dollar-backed stablecoin that today has a market cap exceeding $4.5 billion USD, making it the fastest-growing fiat-backed stablecoin in history.” Translation: We’ve been enormously successful.
As with Trump, Steve Witkoff has argued that having a network of business relationships is not only fine, it’s good.
In October, after a Gaza ceasefire was announced, Witkoff, alongside Jared Kushner, participated in a wide-ranging interview with 60 Minutes’ Lesley Stahl. Kushner told Witkoff that what others call conflicts, he calls trusted relationships. Witkoff agreed: “Conflict of interest is a terminology used by some, and we call it experience, we really do.”
“You call conflict of interest experience?” Stahl asked.
“Because we don’t think there was a conflict, Lesley, that’s why,” Witkoff replied. “Because we don’t think that we crossed any ethical barriers.” The business relationships, he argued, made him much more sophisticated when it came to diplomatic relationships. They’re what made it all work.
Witkoff has become so ubiquitous in international transactions that his role as the co-founder of Trump’s business has all but faded into the gilt wallpaper of the Oval Office. His appointment as envoy to everywhere has shifted the paradigm, in plain sight.
Steve Witkoff travels through the world like a shadow. He rarely appears in public in the United States. He briefs reporters and does television interviews, but few people would recognize him on the streets of most cities in America. In Israel, this is not true. “Once he became Middle East envoy and was given responsibility for the hostages, he became one of the most famous people in Israel overnight,” an Israeli journalist who has covered him told me.
He received a hero’s welcome in Hostage Square in Tel Aviv after forging a tenuous Gaza ceasefire last October, visibly moved as he was drowned out by appreciative shouts of “Thank you, Witkoff!” Witkoff had met for months with the families of hostages, given them his phone number, and bonded with them over the tragic loss of his own son to the drug overdose, conveying to them, as an as Israeli journalist who covered the negotiations told me, that he deeply understood “the significance of saving even one life for a family.” It’s a connection, a Gazan journalist said, that Witkoff also made with Hamas leaders, being in the unlucky “club of parents who have lost children,” and, this person said, it won him their grudging respect.
And so, on a warm night in early October 2025, after he had negotiated the Israel–Gaza ceasefire, word began to circulate that he would make an appearance at Hostage Square. The crowd extended for blocks, jubilant, “like New York when the Knicks won,” a journalist who was there told me. Taking the stage to shouts of his name, Witkoff went on to thank all the leaders who had participated in the deal “for showing that the future of this region can be built not on the ashes of old hatred but on the promise of shared hope.” Even though his mention of Israeli Prime Minister “Bibi” Netanyahu elicited boos, Witkoff maintained control of the crowd. He nodded to the families of “children who are not coming home, members of a very terrible club that I am a member of myself.”
Then it was back to even thornier negotiations in Russia–Ukraine, and Iran.
Unlike in Israel, Witkoff did not have recent business activity in those portions of the world. He was greeted with suspicion by the Ukrainians, who saw him as a tool of Putin, people familiar with Ukrainian negotiators told me. The White House pushed back on this. “Like President Trump, Special Envoy Witkoff is willing to work with anyone to advance America’s foreign policy interests,” Kelly said. “His results speak for themselves.”
The Iranians see Witkoff’s business ties to the UAE, and Jared Kushner’s ties to the Saudis, not to mention Israel, as cause for deep suspicion as well, people familiar with Iranian negotiators told me. Saying that Kushner “is a volunteer” with a “record of success in helping the President,” Kelly maintained that “his private business activities have nothing to do with the President or the administration.”
Even in Witkoff’s earliest encounters, “there were concerns about Witkoff business ties,” including his earlier dealings with Qatar and the UAE, said Seyed Hossein Mousavian, a former Iranian diplomat who moved to the U.S. and became a scholar at Princeton University. “They knew he had close ties to Netanyahu.” The Iranians believed that “Witkoff had meetings with high-level Israelis before and immediately after” he met with them, Mousavian said.
Witkoff’s job with Iran was particularly difficult, almost every former diplomat I spoke with said. Iranians “know that Trump reneges on everything in all his life,” said George Perkovich, a senior fellow at the Carnegie Endowment for International Peace. This was certainly the pattern in his business life: Trump regularly stiffed lawyers and contractors, negotiating their agreed-upon fees to 20 or 30 percent of what he’d promised, or refusing to pay them at all, as he did to the contractors who built the minarets for the Trump Taj Mahal casino in Atlantic City. The Iranians were keenly aware of this history, Perkovich said, layered on their own experience of Trump’s walking away from Obama’s peace accord in Trump’s first term.
But Witkoff himself had his own liabilities, people who worked in the Clinton, Bush, Obama, Biden, and Trump administrations told me. Like Trump, he is supremely confident in his own dealmaking and will take total control of his interactions. He would take phone calls with the president before, during, and after a meeting. And yet, like Trump, the details never seemed to matter. Frustratingly for career diplomats, Witkoff brushed off the usual cadres of government experts for complex negotiations.
Over and over, the former officials I spoke with said, Witkoff was not in touch with the proper government staff experts and authorities for such a deal. (The White House denied this.) In an early trip to Moscow, Witkoff brought his girlfriend, pro golfer Lauren Olaya. He initially met with Putin without a U.S. interpreter, a move that was seen by former U.S. officials as putting himself in a position naively vulnerable to Russian manipulation.
In the Iran negotiations, people who are in touch with current and former State Department employees told me, he and Kushner often met with Iranians without speaking to the people who could explain the complexities of uranium enrichment, say, or centrifuges. The White House maintained that experts from the State, Defense, and Energy departments have been involved in “all” of Witkoff’s negotiations. But “he doesn’t know what he doesn’t know,” Richard Nephew, an Obama- and Biden-era Iran negotiator, told me. “He has no idea of history,” added Perkovich.
As I write, the bombing in Iran has intensified. The “memorandum of understanding” Trump signed in mid-June in Versailles, providing for a ceasefire and a 60-day window to conclude negotiations, was met at its halfway point with renewed aggression by both sides. Headlines are full of those hated words forever war, but also: glimmers of hope.
A week after the resumption of bombing, an anonymous X account that describes itself as “Iranian” posted that Iran had sent a text message to Vice President J.D. Vance saying that negotiators, “mainly Kushner and Witkoff,” were “more interested in exploiting insider knowledge to profit in financial markets than reaching a deal.”
This is the kind of charge that pings around the internet but usually goes nowhere. And then, on July 16, as the U.S. was expanding its bombing campaign, the vice president amplified the post by responding to it. “This is completely bogus,” he wrote. “I never received a message like this.
“If I had, I would have said: Jared and Steve are trusted members of the president’s team and very dear friends. No one has done more than the two of them to work towards peace and prosperity in the region.”
On his own X account, Zach Witkoff, the son of one of those friends, and CEO of the cryptocurrency business that has generated so much money for the Trump family and his own, reposted Vance’s denial that Steve Witkoff was out to make a profit through his diplomacy.
A couple of posts later, Zach Witkoff added another message, a video recapping the “World Liberty Forum” held at Mar-a-Lago in February. The video prominently featured Zach Witkoff and two of the president’s sons, Don Jr. and Eric, extolling the success of their company. They looked suffused with happiness and the glow of victory. “This is just the beginning,” the video said.
