Trump has appointed two unconventional figures as his top Iran negotiators: Steve Witkoff and Jared Kushner. Both come from New York real estate and have deep personal ties to the president, but their roles in the administration’s Iran diplomacy are sharply different. Witkoff, a billionaire developer with no prior diplomatic experience, serves as the lead negotiator handling the actual text, verification mechanisms, and sequencing of sanctions relief. He has been unusually transparent in interviews, revealing specific terms like full IAEA access and phased sanctions removal. Kushner, Trump’s son-in-law, operates unofficially as a senior advisor while running Affinity Partners, a private equity firm funded by Gulf sovereign wealth. He manages relationships with Saudi Arabia and the UAE, ensuring regional support for any deal. The administration’s approach prioritizes personal loyalty and business instincts over traditional diplomatic experience. Critics worry this transactional style may sacrifice rigor for speed, especially given Iran’s advanced nuclear program — enrichment at 60% with a breakout time of one to three weeks — and the regime’s history of playing the long game. The recent Strait of Hormuz reopening deal, announced alongside progress on a draft text, raises questions about what concessions were traded for pace.
#3611: Who Are Trump’s Iran Negotiators?
Steve Witkoff and Jared Kushner are Trump’s top Iran negotiators. What does their real estate background mean for diplomacy?
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New to the show? Start here#3611: Who Are Trump’s Iran Negotiators?
Daniel sent us this one — and it's a deceptively simple question. He's asking who are Steve Witkoff and Jared Kushner, the two men Trump has appointed as his top negotiators with Iran. But the real question underneath is bigger. What does it mean that these two specific people — a real estate billionaire and the president's son-in-law — are the ones sitting across the table from Tehran? And what does that tell us about how this administration approaches diplomacy?
It's a fascinating pairing because on the surface they look similar — both come out of New York real estate, both have deep personal relationships with Trump — but their approaches and the roles they've been given are actually quite different. And the results so far, I mean, we just saw the Strait of Hormuz reopening deal announced. Something is working.
Or something is being traded. Let's start with Witkoff, because he's the one who's been most visible in the past few weeks. Who is he?
Steve Witkoff is a billionaire real estate developer who's been friends with Trump for about forty years. They met in the eighties, both working in Manhattan commercial real estate. Witkoff built his own firm, the Witkoff Group, which owns something like seventy properties across the United States and Europe. But here's what's interesting — he had zero diplomatic experience before Trump tapped him. His entire career was buying and selling buildings.
Which is either a disqualification or exactly the qualification Trump wants. I think we know which way the administration sees it.
Trump's view has always been that traditional diplomats get bogged down in process and lose sight of the deal itself. Witkoff's background is in high-stakes negotiation where the only metric that matters is whether the deal closes. And to be fair, Witkoff's track record in this administration has been stronger than a lot of people expected. He was the lead negotiator on the Gaza ceasefire and hostage release framework earlier this year, and by most accounts he was effective.
Effective at what, though? That's the question that keeps nagging at me. There's a difference between closing a real estate deal and negotiating with a regime that has spent forty-five years chanting death to America. In real estate, both sides fundamentally want the deal to happen — they're haggling over price and terms. With Iran, you're dealing with an ideological state that views the negotiation itself as a form of warfare.
Witkoff seems to understand that distinction, at least intellectually. There was an ABC News interview with him just last week where he was asked about the Iran talks, and he said — I'm paraphrasing — that the key difference from a business deal is that in diplomacy, the other side might prefer no deal at all if they believe stalemate serves their interests. So he's not naive about it.
He's also been unusually transparent about what's being discussed. That ABC interview — he revealed details that career diplomats would never put on the record. He talked about the timeline for sanctions relief, the sequencing of verification measures, even hinted at what the administration considers its red lines. That's either strategic or reckless, and I'm not sure which.
Let me read you the key quote from that interview. He said the U.is looking for a deal that includes full IAEA access to all nuclear sites, a permanent cap on enrichment at a level far below weapons-grade, and a mechanism for snapback sanctions if Iran violates terms. In exchange, he said the U.is prepared to lift most economic sanctions in phases tied to verified compliance. That's more specific than anything we heard during the entire Obama-era negotiations.
The Iranians responded how?
They confirmed the broad framework. Iran International reported in late May that both sides had agreed to a timetable for finalizing terms, and the Iranian foreign ministry put out a statement acknowledging the negotiations were in what they called the text-drafting phase. That's significant. They're past talking about talking and into actually writing language.
Which brings us to the Strait of Hormuz announcement. Trump said it's reopening. What's the actual status?
This is where it gets complicated. Iran has been harassing and intermittently blocking commercial shipping through the Strait since late twenty twenty-five, ostensibly in retaliation for tightened sanctions. But the timing of the reopening announcement coincided almost exactly with the peace deal timetable being confirmed. The read is that Iran was using Strait access as leverage, and Witkoff's team called their bluff by making it a precondition for continued talks.
Or they traded something for it. That's the thing with deals — you never get something for nothing. If Iran suddenly agreed to reopen the Strait after months of brinkmanship, they extracted a concession somewhere else.
The question is what. And this is where Kushner enters the picture, because Kushner's role is different from Witkoff's. Witkoff is the front man, the day-to-day negotiator. Kushner is operating at a different level.
Let's talk about Kushner then. Everyone knows the basic biography — married to Ivanka, former senior advisor in the first Trump term, architect of the Abraham Accords. But what's his actual role now?
Officially, he doesn't have one. He's not a government employee. He runs Affinity Partners, a private equity firm that's raised billions, mostly from Gulf sovereign wealth funds. But he's been serving as what the administration calls a senior advisor on Middle East policy, and his involvement in the Iran track has been confirmed by multiple outlets including Arab News.
The president's son-in-law, who runs a firm funded by Saudi and Emirati money, is advising on negotiations with Iran. That's not a conflict of interest — that's a conflict of interests, plural, all holding hands and dancing in a circle.
It's definitely complicated. But the counterargument, and I think this is what the administration would say, is that Kushner's relationships in the Gulf are precisely what make him valuable. The Abraham Accords happened in large part because he had direct, trust-based relationships with MBS, with MBZ, with the Bahraini leadership. Those aren't relationships you build through diplomatic cables. They're built through years of personal engagement.
Also through years of the Saudis investing in his fund. Let's not pretend there's a firewall between Kushner the diplomat and Kushner the businessman. There isn't one, and the administration hasn't even tried to construct one.
They haven't. And that's either a feature or a bug depending on your view of how diplomacy should work. The traditional model says you need career foreign service officers who are insulated from commercial interests. The Trump model says you want people who have skin in the game and understand what all parties actually want, not just what they say in formal meetings.
What's the division of labor between these two? If Witkoff is doing the table work, what is Kushner doing?
From what's been reported, Kushner is handling what you'd call the strategic layer. He's managing the relationships with the Gulf states that have a huge stake in whatever deal emerges. Saudi Arabia and the UAE are terrified of a nuclear Iran — they're also the ones who would benefit most from normalized economic relations if sanctions lift. Kushner's job is to make sure the regional architecture supports the deal rather than undermining it.
Witkoff handles the actual text.
Witkoff handles the actual text, the verification mechanisms, the sequencing. He's been traveling regularly — there have been meetings in Oman, in Geneva, reportedly one round in Doha. The State Department has been involved but the lead negotiator is Witkoff personally, which is unusual. Normally you'd have a career diplomat like Rob Malley or Brian Hook in that chair.
Brian Hook was the Iran envoy under Trump the first time around. What happened to him?
He's still around, actually — he's been serving in an advisory capacity. But he's not the lead. The lead is Witkoff. And that tells you something about how much Trump values personal loyalty and business instincts over diplomatic experience. Hook negotiated the maximum pressure sanctions regime. He knows the Iran file cold. But he's not the guy in the room.
Because he's not Steve Witkoff. He's not someone Trump has known for forty years, someone who's been through deals and busts and lawsuits and all the mess of New York real estate with him. That history matters to Trump in a way that resume lines don't.
And that's not necessarily wrong if you judge by results. The Obama administration had brilliant career diplomats working the Iran file — Wendy Sherman, Bill Burns, people who knew every detail of centrifuge technology and breakout timelines. And they got the JCPOA, which Trump then withdrew from because he thought it was a bad deal. From Trump's perspective, the process doesn't matter. The deal terms matter.
Here's my concern, and I want to push on this. The JCPOA, whatever its flaws, was negotiated by people who understood that you can't trust Iran on intentions — you can only verify capabilities. The entire structure was built around that insight. Are Witkoff and Kushner bringing that same skepticism, or are they approaching this like a transaction where both sides shake hands and everyone goes home happy?
That's the central question. And I think the evidence is mixed. On one hand, Witkoff has been explicit about needing robust verification — he mentioned the IAEA, he mentioned snapback, he mentioned phased sanctions relief. Those are the right building blocks. On the other hand, the speed at which this is moving — we went from no diplomatic contact to a draft text in roughly four months — makes you wonder what's being traded away for pace.
There's an old saying in negotiation: you don't get what you deserve, you get what you negotiate. And the speed point matters because Iran has been playing the long game on this since nineteen seventy-nine. They're patient. They view time as an asset. If they're suddenly in a hurry, I want to know why.
Part of the answer is that Iran's economy is in genuinely terrible shape. The rial has collapsed, inflation is running above forty percent, and the maximum pressure sanctions have cut their oil exports significantly even with Chinese back-channel purchases. The regime has been facing sustained domestic unrest — the Mahsa Amini protests never really ended, they just went underground. So there's real pressure to get sanctions relief.
There's also the nuclear clock. Where is Iran's program right now?
They're enriching uranium to sixty percent at multiple facilities. That's not weapons-grade — you need about ninety percent for a bomb — but the jump from sixty to ninety is technically much shorter than the jump from zero to sixty. Most estimates put their breakout time, meaning the time to produce enough fissile material for one weapon, at somewhere between one and three weeks. That's not a lot of margin.
They're sitting at the table with a gun on it, is what you're saying.
A gun that's mostly assembled, yeah. And that changes the negotiation dynamics considerably. You're not negotiating to prevent a capability anymore — that ship sailed. You're negotiating to cap and verify a capability that already exists, and to prevent weaponization. That's a harder problem.
Which is where Kushner's regional angle gets interesting. If the goal is no longer preventing enrichment but containing it within a verified framework, you need buy-in from the entire neighborhood. You need Saudi Arabia and the UAE to believe the verification is real. You need Israel to not launch a preemptive strike. That's diplomatic work that goes way beyond the text of an agreement with Tehran.
This is where Kushner's value proposition actually makes sense, even if the conflicts of interest make people uncomfortable. He can call MBS directly. He can call MBZ directly. He has their personal cell phone numbers. When he says the deal includes verification measures the Gulf states can trust, he's not just reading a briefing paper — he's someone they've done business with.
The business part being the operative word. Affinity Partners has taken something like two billion dollars from the Saudi Public Investment Fund. That's not a consulting retainer. That's generational wealth being managed by the president's son-in-law while he advises on Middle East policy.
It's two billion from the Saudis, plus significant commitments from the UAE and Qatar. And you're right, it creates an appearance problem that the administration has basically decided to ignore. Their position seems to be that Kushner's business relationships are a private matter and his advisory role is informal enough that formal ethics rules don't apply.
Which is legally true and practically absurd. Everyone understands what's happening. The Gulf states are investing in Kushner's fund because he's the president's son-in-law and a key foreign policy advisor. He's advising on foreign policy in ways that affect the value of those investments. The circle is so tight it's practically a dot.
Yet — and I want to be fair here — the Abraham Accords were a genuine diplomatic achievement. They normalized relations between Israel and several Arab states in a way that decades of traditional diplomacy had failed to do. Kushner's approach, which was essentially to bypass the Palestinian issue entirely and build direct economic and security ties, worked where the conventional playbook didn't.
It worked in the short term. The question is whether it's sustainable without addressing the underlying Palestinian question, which we're now seeing play out in real time. But that's a different episode. For Iran, the Kushner approach seems to be similar — build a regional consensus among the Gulf states, get them invested in the verification architecture, and use economic integration as the carrot for Iranian compliance.
Witkoff handles the actual negotiation with the Iranians while Kushner handles the regional diplomacy. It's a two-track approach that mirrors what Kushner did with the Abraham Accords, where he had separate channels with the Israelis and the Arab states and coordinated between them.
Let's talk about the actual deal taking shape. Based on what Witkoff has said publicly and what's been reported, what are the broad strokes?
Here's what we know. The framework includes a permanent cap on enrichment at three point six seven percent — that's the level needed for civilian nuclear power, far below the sixty percent they're currently enriching at. Iran would have to ship out or downblend its existing stockpile of highly enriched uranium. Full IAEA access to all declared sites, plus a mechanism for challenging inspections at undeclared sites. Phased sanctions relief tied to verified milestones. And some kind of sunset clause, which is the most contentious piece.
Sunsets are where these deals live or die. The JCPOA had them, and critics argued they basically gave Iran a patient path to a bomb once restrictions expired. What's different this time?
Witkoff has been vague on this, which tells me it's still being negotiated. But he's hinted that the administration wants a much longer timeline — twenty to twenty-five years rather than the ten to fifteen in the JCPOA — and that certain restrictions, particularly on enrichment capacity, would be permanent rather than sunsetting. Whether Iran will accept permanent restrictions is the billion-dollar question.
They've said repeatedly they won't. Supreme Leader Khamenei has been explicit that any deal must include a finite timeline for all restrictions. That's been their red line since the beginning of the nuclear negotiations.
That's where the regional component matters. If Saudi Arabia, the UAE, and Israel are all invested in the verification framework and have direct lines to Washington, the argument is that even if restrictions eventually sunset, the cost of cheating would be much higher. Iran would be violating an agreement that the entire region has a stake in, not just one with the United States.
That assumes the region stays aligned. Saudi-Iranian rapprochement, which China brokered back in twenty twenty-three, has been fragile but real. The Saudis have reopened their embassy in Tehran. They're talking about economic cooperation. If that relationship deepens, the regional pressure on Iran to comply with a nuclear deal gets more complicated.
And that's another reason Kushner's role matters. He's trying to keep the Gulf states anchored to the U.-led framework rather than drifting toward a separate accommodation with Iran. The Chinese-brokered Saudi-Iran deal was a wake-up call for Washington — it showed that the U.doesn't have a monopoly on Middle East diplomacy anymore.
Which is ironic given how much criticism the U.gets for being too involved in the Middle East. The moment China steps in to mediate, suddenly everyone remembers why American diplomatic leadership matters.
Chinese mediation comes with Chinese interests attached. The Saudis know that. The Emirates know that. They'd rather have the U.as their primary security guarantor, but they'll hedge if they think Washington is unreliable. Part of Kushner's job is to signal that the U.is very much reliable under Trump.
Let me try to synthesize this. You've got Witkoff running the direct negotiations with Iran, applying a real estate dealmaker's instincts to nuclear diplomacy — speed, personal rapport, a focus on closing. You've got Kushner managing the regional architecture, using personal relationships built through business and the Abraham Accords to keep the Gulf states aligned. And you've got a deal taking shape that looks broadly similar to the JCPOA in structure but with longer timelines and a heavier emphasis on regional integration.
That's a fair summary. The JCPOA comparison is unavoidable, even though the administration would bristle at it. The Obama deal was essentially a transaction — sanctions relief for nuclear restrictions. The Trump deal, if it materializes, seems to be aiming for something bigger — a regional security framework where Iran's nuclear program is constrained not just by an agreement with Washington but by economic and diplomatic ties with its neighbors.
Which is a much more ambitious goal. It's also a much more fragile one, because it depends on regional relationships that can shift with a single election or a single crisis.
It depends on Iran's regime being willing to accept a fundamentally different relationship with its neighbors, which has been the sticking point for forty-five years. The Islamic Republic's entire identity is built on opposition to the regional order — to the Gulf monarchies, to Israel, to American hegemony. Asking them to join that order rather than oppose it is asking for more than a nuclear deal. It's asking for a transformation of the regime's strategic posture.
Which brings me back to my skepticism about the dealmaker approach. A real estate transaction assumes both parties want the deal and are negotiating over terms. But Iran's regime may not want the deal at all if the deal requires them to stop being the Islamic Republic in any meaningful sense. They might prefer sanctions and isolation to normalization, because normalization threatens the revolutionary ideology that justifies their domestic repression.
That's the pessimistic case. The optimistic case, and I think this is what Witkoff and Kushner are betting on, is that the regime's survival instinct will override its ideology. The Iranian economy is in freefall. The population is young, restive, and increasingly secular. The regime can't buy loyalty forever with a collapsing currency. At some point, the material need for sanctions relief outweighs the ideological commitment to resistance.
That's where the domestic Iranian dimension comes in. The deal isn't just between Washington and Tehran. It's between the Iranian regime and the Iranian people, who have been paying the price of sanctions for decades. If a deal lifts sanctions and the economy improves, the regime gets a new lease on life. If it doesn't, they've made concessions for nothing.
Which is exactly why the Supreme Leader has been so cautious about these negotiations. He authorized the talks, but he's been very careful not to endorse them publicly. The Iranian media has been instructed to describe them as discussions, not negotiations. The regime is hedging against the possibility that the deal falls apart or that Trump changes his mind.
Trump changing his mind is a material risk. This is the same president who withdrew from the JCPOA in twenty eighteen, called it the worst deal ever, and then authorized the strike that killed Qasem Soleimani. The Iranians know all of this. They're negotiating with someone who has demonstrated a willingness to walk away from deals and escalate militarily.
They're also negotiating with someone who has demonstrated a willingness to make deals that other presidents wouldn't. The Abraham Accords. The USMCA trade deal. The Phase One China deal. Trump's entire brand is that he closes. And for the Iranians, the fact that Trump is transactional rather than ideological might actually be reassuring — they know what he wants, and they can negotiate over price.
As opposed to an administration driven by human rights concerns or democracy promotion, where the asks would be unpredictable and potentially existential for the regime.
The Trump administration has been very clear that it's not interested in regime change. Witkoff said as much in that ABC interview — he said the U.is not seeking to overthrow the Iranian government, it's seeking a verifiable agreement on the nuclear program. For the mullahs, that's about as good as it gets from Washington.
Which is a remarkable shift from the maximum pressure rhetoric of Trump's first term. Back then it was all about strangling the regime until it collapsed or capitulated. Now it's about making a deal.
That shift is partly because maximum pressure didn't collapse the regime. It hurt the economy badly, it fueled domestic unrest, but the regime survived. The lesson the administration seems to have drawn is that sanctions are leverage for negotiation, not a tool for regime change. Use them to get a deal, not to topple the government.
Where does this leave us? The deal isn't done. The framework is being drafted. Witkoff is in the room. Kushner is working the phones. The Strait of Hormuz is supposedly reopening. What should we be watching for in the next few months?
A few key signposts. First, whether Iran agrees to the permanent enrichment cap or insists on a sunset. That's the single biggest sticking point. Second, whether the IAEA gets the access it's asking for — not just to declared sites but to the undeclared ones where past military dimensions work may have occurred. Third, whether the Gulf states publicly endorse the framework or stay quiet. If the Saudis and Emiratis are on board, that's a strong signal. If they're hedging, something's wrong.
Fourth, whether Congress gets a vote. The JCPOA was structured as a political commitment rather than a treaty specifically to avoid Senate ratification. The current administration hasn't said whether they'd submit this deal for congressional approval, but if it includes permanent commitments on sanctions relief, there's a strong argument that it should go through the Senate as a treaty.
That's a huge open question. The Iran Nuclear Agreement Review Act, which passed in twenty fifteen, requires the administration to submit any Iran deal to Congress for a review period. But the current Congress is Republican-controlled, so the politics are different. The question is whether there are enough Republican skeptics to block a deal that Trump supports.
That's where the Kushner-Witkoff dynamic gets interesting again. They're both Trump loyalists, but they have different constituencies. Witkoff is a businessman who operates in Trump's world. Kushner has his own political network, his own relationships on the Hill, his own complicated history with the Republican foreign policy establishment. If there's a fight over the deal in Congress, those two may not be on the same side of every tactical question.
That's speculative, but it's not crazy. Kushner has been more hawkish on Iran historically than the current negotiation track would suggest. He was a key architect of the maximum pressure campaign in the first term. His pivot to being a deal facilitator is pragmatic rather than ideological, and pragmatism can shift again if circumstances change.
The other wildcard is Israel. Netanyahu has been uncharacteristically quiet about these negotiations. During the Obama years, he was giving speeches to Congress and making his opposition very public. This time, he's been muted. What's going on there?
Partly it's that Netanyahu has a much better relationship with Trump than he did with Obama. He trusts that Trump won't agree to something that leaves Israel exposed. Partly it's that the Abraham Accords changed the calculus — Israel now has open diplomatic relations with several Gulf states, so it's less isolated in its concerns about Iran. And partly, I think, Israel is watching and waiting. They haven't taken a preemptive strike off the table, but they're not going to undermine negotiations that have the potential to cap Iran's program.
Unless they conclude the deal is bad and decide to act. That's always the Israeli wildcard. They've done it before — Osirak in eighty-one, the Syrian reactor in two thousand seven. If they think Iran is stringing the negotiations along while getting closer to a bomb, they have the capability to set the program back unilaterally.
And that's another reason the speed of these negotiations matters. The longer they drag on, the more time Iran has to advance its program and the more tempted Israel might be to act. Closing quickly isn't just Trump's preference — it's a strategic necessity.
To come back to the original question — who are Steve Witkoff and Jared Kushner — I think the answer is more interesting than just their biographies. They represent a theory of diplomacy that treats international relations as a series of transactions between individuals rather than a system of institutions and alliances. Witkoff brings the dealmaker's instinct. Kushner brings the personal network. Together, they're attempting something that career diplomats have tried and failed to do for decades.
Whether they succeed or fail, the attempt itself tells you a lot about how this administration sees the world. It's not about process. It's not about precedent. It's about whether two guys who know how to close a deal can close the hardest deal in international diplomacy.
The hardest deal, and also the one where failure doesn't mean a lost commission — it means a nuclear-armed Iran and potentially a regional war. The stakes are slightly higher than a Manhattan office tower.
I do think it's worth noting, and this is where I'll put my own cards on the table, that I find the whole setup a little unsettling. Not because I object to the outcome — a verifiable deal that caps Iran's program and reopens the Strait is a good thing. But because the process is so concentrated in two individuals with such close personal and financial ties to the president. If Witkoff and Kushner get this right, it'll be a historic achievement. If they get it wrong, there's no institutional backstop. There's no career diplomat who's going to catch the mistake. The whole thing rests on their judgment.
That's the bet. And it's consistent with how Trump has always operated — pick people you trust, give them authority, and hold them accountable for results. The downside is exactly what you said. The upside is that you can move faster and more flexibly than any institutional process would allow.
Which is how we got from no talks to a draft framework in four months. Speed has value. Whether it has enough value to offset the risks of a personalized, deinstitutionalized diplomacy is the question history will answer.
We'll be watching.
And now: Hilbert's daily fun fact.
Hilbert: In Edo period Japan, sumptuary laws dictated that only samurai could wear certain shades of red. Commoners who wore forbidden colors could be fined or imprisoned. The name of the specific crimson dye restricted to the warrior class was kurenai, derived from the Chinese word for red, and its use by merchants was considered a direct challenge to the social order.
Hilbert: In Edo period Japan, sumptuary laws dictated that only samurai could wear certain shades of red. Commoners who wore forbidden colors could be fined or imprisoned. The name of the specific crimson dye restricted to the warrior class was kurenai, derived from the Chinese word for red, and its use by merchants was considered a direct challenge to the social order.
The color of your shirt could get you thrown in jail.
That's our show. Before we go — one thing to keep watching. The deal isn't done, and the next sixty days will tell us whether Witkoff and Kushner have actually cracked this or whether we're heading for another cycle of escalation. Either way, we'll cover it here. Thanks to our producer Hilbert Flumingtop. This has been My Weird Prompts. Find us at myweirdprompts.com or wherever you get your podcasts.
See you next time.
This episode was generated with AI assistance. Hosts Herman and Corn are AI personalities.