When the billionaire developer Steve Witkoff was tapped as the Trump administration’s Middle East envoy last November, several of his former associates in the real estate industry applauded the unorthodox appointment to a high-profile role overseeing some of the most sensitive foreign policy issues facing the United States.

Even as he had no diplomatic experience, Witkoff, a close friend of President Donald Trump, won praise as a shrewd negotiator and creative dealmaker with sharp business instincts who could draw on decades of experience navigating New York City’s cutthroat real estate market — where he had once been known to carry a handgun during his early years overseeing distressed properties.

But more than three months into his new posting, Witkoff, whose portfolio has expanded beyond the Middle East, is now facing scrutiny from a growing number of critics casting doubt on his qualifications as he assumes a leading role in nuclear negotiations with Iran as well as direct discussions with Russia to end its war against Ukraine.

Among some of Witkoff’s fellow developers who are already souring on his early tenure as Trump’s top envoy, there is skepticism that his insistent focus on striking a deal above all else, an asset in his former job, may be a liability as he engages in high-stakes negotiations with bad-faith actors such as Iran and Russia seeking potentially dangerous concessions from the United States.

“They came in almost wanting a deal more than anything, and that’s not a very good negotiation posture,” Dan Kodsi, a developer in Miami, where Witkoff also owns property, told Jewish Insider of the envoy’s team. “I think they showed their hand way too early, almost like having a deal was more important than having a good deal.”

Kodsi, who said he voted for Trump in the most recent election, suggested that Witkoff’s skills as a developer could potentially be useful in diplomatic efforts. “Developers deal with very tough situations. We’re always facing a wall — always looking for a door or a window to escape,” he explained in a recent interview. “It makes us good at being able to persevere and get around things and to get a deal done.”

But the “problem,” he said, is there are limitations to those analogies, particularly during negotiations with ruthless dictators in which traditional business incentives are irrelevant. “This is not business. It’s not like, ‘I’ll give you more money and we will make a deal,’” he said. 

By initially suggesting that the U.S. was open to compromise with Iran, Witkoff left his team exposed with little leverage, Kodsi told JI, even as Trump has dangled the threat of military action to thwart the regime’s nuclear ambitions. “These guys have not kept any cards in their back pocket for negotiation,” he said of Witkoff and his team, which now includes a group of technical experts led by Michael Anton, the State Department’s director of policy planning.

Witkoff, for his part, has continued to use business analogies to clarify his approach to the ongoing negotiations, even while acknowledging he is now pursuing goals that are far more lofty than any real estate transaction.  

“The enormity of it sort of struck me,” he said of his meeting with Russian President Vladimir Putin last week, in a WABC Radio interview on Tuesday. “I’ve been in the real estate business, and in the past, it was buying a bigger building, or building a bigger building,” he added. “And this was much more about saving people’s lives, ending the carnage, being there on behalf of the American people, on behalf of President Trump. I had to pinch myself.”  

“From what I can tell, these guys are just trying to make a deal,” Henry Liebman, a top developer in Seattle, said. In the process, he added, “it almost seems like they’re getting played.”

He described a similar feeling about the nuclear talks with Iran — which he called “an existential issue for the world, nuclear and weaponization.”

“It felt like I was a fiduciary, that I was doing something larger than myself on behalf of, again, the United States government and President Trump, with strong directives from him as to what he wanted to achieve,” Witkoff said in the radio interview with John Catsimatidis and Rita Cosby.

Henry Liebman, a top developer in Seattle, argued that Witkoff and his team appear “naive” in their dual efforts to negotiate with Iran and Russia, which he characterized as misguided. “With Iran, you can’t let them have nukes and you can’t have them supporting proxies” in the region such as the Houthis in Yemen, he told JI, while describing proposed land concessions to Putin as “not a good idea.”

“From what I can tell, these guys are just trying to make a deal,” Liebman reiterated. In the process, he added, “it almost seems like they’re getting played.”

In recent weeks, Witkoff has drawn backlash over contradictory remarks about Iran’s ability to enrich its own uranium, a key issue in the ongoing talks, as well as a series of stumbles in which he has praised Putin and suggested he had been “duped” by Hamas amid failed negotiations to release the hostages held by the terrorist group in Gaza.

His continued lack of clarity about permissible continued nuclear enrichment by Iran has raised alarms among conservatives who are skeptical that Witkoff is in command of technical details crucial to reaching a deal with the Islamic Republic distinct from the agreement brokered by the Obama administration a decade ago — which opponents had viewed as a pathway to a nuclear weapon. 

Trump, who recently said that the talks are going “very well” and suggested that “a deal” is imminent, pulled out of the original agreement during his first term.

Witkoff has not publicly shared details on the latest round of negotiations with Iran that concluded in Oman last weekend. Though he said in a statement in mid-April that Iran “must stop and eliminate its nuclear enrichment and weaponization program” in order for a deal to “be completed,” he has reportedly told Trump administration officials that seeking full dismantlement, which the Iranians have resisted, is unlikely to result in a deal.

His mixed messaging has raised questions about whether Witkoff is now on course to simply revive an old agreement that has long been anathema to most Republicans.

In his radio interview on Tuesday, Witkoff sought distance from the original nuclear deal with Iran, calling it “fundamentally flawed because the sanctions sunsetted, and yet the mandate as to how you’re supposed to conduct yourself — not enriching, not weaponizing — that did not sunset,” he said, referring loosely to terms of the agreement. 

“I am concerned that in the face of ill-thought tariff policy, and resistance to Ukraine-Russia resolution, he and his administration are looking for a victory — any victory — and that early compromise on Iran is a bad thing,” Steve Minn, a real estate developer in Minneapolis, told JI. “We have Iran on the ropes,” he said. “Let’s keep Saudi Arabia and Egypt eager to see Iran diminished.”

“You and I both know, in business, one-way options don’t make sense,” he added. “Theyre not fair, and that was a one-way option for the Iranians, and it’s got to be rectified.”

As a fourth round of discussions with Iran is expected to be held in Rome on Saturday, Steve Minn, a real estate developer in Minneapolis who describes himself as an “Israel hawk” and voted for Trump three times, also voiced reservations about the current trajectory of U.S. talks with the Islamic Republic.

“I am concerned that in the face of ill-thought tariff policy, and resistance to Ukraine-Russia resolution, he and his administration are looking for a victory — any victory — and that early compromise on Iran is a bad thing,” Minn told JI. “We have Iran on the ropes,” he said. “Let’s keep Saudi Arabia and Egypt eager to see Iran diminished.”

In a statement to JI on Wednesday, Anna Kelly, a White House spokesperson, said Witkoff “is a trusted friend of President Trump, and he left behind a massive business enterprise to serve our country as a special envoy.”  

“His results speak for themselves, including the release of Marc Fogel from Russia and hostages trapped in Gaza,” Kelly continued. “The president is incredibly proud of all Mr. Witkoff has accomplished to help restore peace through strength, and he will continue to leverage Mr. Witkoff’s talents to advance his America First foreign policy vision.”  

“He’s not going to go in there and be the best person in diplomacy on Day One, but he knows that he has a mission and he has to get Problem A solved — and there are all these different variables in the problem he has to think about,” Eric Benaim, the founder and CEO of Modern Spaces, a residential brokerage firm in New York City, told JI. “It’s just like a negotiation of anything.”

To be sure, Witkoff still has several defenders in the real estate world who feel that he is doing a good job with a uniquely challenging set of issues. “I cannot think of any one instance where I thought Steve is underprepared or overwhelmed,” Joseph Moinian, an Iranian-born real estate developer in New York City who has known Witkoff for years, told JI. “With him you know that the best outcome is the one he has achieved.”

“If anyone thinks that he is ‘in over his head’ it is not because he is incapable,” Moinian said earlier this week, “it is because the problems are extremely and increasingly impossible.”

Eric Benaim, the founder and CEO of Modern Spaces, a residential brokerage firm in New York City, likewise expressed satisfaction with Witkoff’s approach and said he believed that a background in real estate development is helpful to shake free of a status quo that has hindered progress in the region, even as he acknowledged there is a “learning curve” for such diplomatic work.

“He’s not going to go in there and be the best person in diplomacy on Day One, but he knows that he has a mission and he has to get Problem A solved — and there are all these different variables in the problem he has to think about,” Benaim told JI. “It’s just like a negotiation of anything.”

But as Witkoff has struggled to find his footing on Middle East policy and other key issues, Eric Anton, a veteran real estate broker and Jewish Republican in New York City who has worked on deals with the developer, suggested the newly minted envoy could be reaching a point at which he is over-leveraged as he takes on a dizzying array of responsibilities in his initial months on the job.

“He’s got so much on his plate,” Anton told JI, “ it’s like drinking 20 milkshakes.”