Iran's Art of the Deal(ay)
The Islamist strategy is not to win every battle. It is to remain standing when the negotiations end.
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Donald Trump built his public identity around “The Art of the Deal” — the belief that successful negotiation requires leverage, pressure, unpredictability, and the willingness to walk away.
The Iranian regime has perfected a different art: the art of the deal(ay).
On Sunday, reports emerged that mediators were attempting to revive the memorandum of understanding signed by the United States and Iran on June 17th. The proposed arrangement would renew the ceasefire and reopen the Strait of Hormuz without fees, but only for another 60 days. At the same time, Iranian officials announced that negotiations with Oman over a mechanism to govern shipping through the strait were entering their “final stages.”
That phrase — for another 60 days — contains the entire Iranian strategy.
Iran is not offering to resolve the crisis. It is offering to postpone it. It is not agreeing that one of the world’s most important waterways must remain permanently open to international commerce. It is offering the world a temporary license to use it. It is not abandoning its attempt to control the Strait of Hormuz. It is asking everyone to stop fighting while the Iranian regime negotiates the terms under which it will exercise that control.
In other words, Iran is not negotiating an end to the crisis. It is refinancing the crisis.
The original memorandum was supposedly a breakthrough. It declared an end to military operations, reopened the Strait of Hormuz, began the removal of the American naval blockade, and created a 60-day period for negotiating a permanent agreement.
But look more closely at how it was constructed: Iran promised to use its “best efforts” to guarantee the safe passage of commercial ships without charge “for 60 days only.” The future administration of the strait would then be negotiated with Oman and other Gulf states.
Meanwhile, the framework placed sanctions relief, oil waivers, access to frozen Iranian assets, and an enormous reconstruction and development plan on the table. The most important nuclear questions (including enrichment and the disposition of Iran’s enriched material) were pushed into negotiations over a future final agreement.
The West was being asked to begin delivering tangible benefits while Iran’s most important obligations remained matters for future discussion. This is not accidental ambiguity. The ambiguity is the product. The regime’s objective is to make every basic obligation temporary, conditional, reversible, and renegotiable.
Iran does not permanently reopen the Strait of Hormuz. It opens it for 60 days. It does not dismantle its nuclear infrastructure. It agrees to discuss what might eventually happen to it. It does not surrender its ability to threaten international shipping. It negotiates which routes ships may take and what authority the Iranian regime might exercise over them.
Then, when the temporary period approaches its end, or when Iran decides the agreement is no longer useful, the regime manufactures another dispute.
The route is unacceptable. The inspections are unfair. The sanctions relief is insufficient. The Americans violated the spirit of the agreement. The international community failed to respect Iranian sovereignty. The details require further technical discussion.
The result is another emergency, another round of mediation, another temporary framework, and another celebration in Western capitals that diplomacy has been “saved.”
The original memorandum did not even survive its first few weeks intact. Iran attacked a commercial vessel in the strait just over a week after the agreement was signed, triggering another exchange of strikes. The disagreement centered precisely on the vague language governing Iranian control over shipping routes and future fees.
Now the world is negotiating its way back into essentially the same arrangement. That is not progress. It is a subscription service. Every 60 days, the international community must renew its access to normality.
The most remarkable part of this diplomacy is that Iran is treated as though it is making an extraordinary concession by allowing commercial ships to travel through an international waterway. But Iran helped create the crisis in the first place.
Closing or threatening the Strait of Hormuz gives the Iranian regime leverage because the waterway carried roughly one-fifth of the world’s oil and liquefied natural gas before the war. Disrupting it raises energy prices, frightens Gulf governments, pressures Western voters, and creates immediate demands for de-escalation.
Iran therefore benefits twice. First it benefits from the crisis, then it benefits from temporarily suspending the crisis. This is the basic Iranian business model: Manufacture instability, demonstrate the ability to intensify it, and then demand political or economic compensation for briefly restoring the conditions that existed before Iran disrupted them.
A government takes hostages and demands concessions for their release. A proxy militia attacks shipping and demands recognition as a political actor. A nuclear program advances beyond previously accepted limits and is then partially frozen in exchange for sanctions relief. A waterway is threatened and then reopened for 60 days as though the Iranian regime has bestowed a gift upon humanity.
The regime transforms ordinary compliance into a valuable commodity. And because the agreement is temporary, Iran can sell the same commodity again.
This method is not unique to Iran. It is part of the strategic culture of revolutionary Islamist movements such as Hamas and Hezbollah — movements whose ultimate objectives cannot be reconciled with permanent coexistence and whose continued survival is itself considered a form of victory. Such movements do not necessarily negotiate to reach an agreed destination. They negotiate to survive the journey.
Hamas has repeatedly used phases, sequencing disputes, temporary pauses, partial hostage releases, and demands for guarantees to preserve its leverage. Even the latest Gaza roadmap remains entangled in another dispute over who must move first. Hamas says Israel must cease its operations, withdraw forces, and increase aid before Hamas places its weapons into storage. Israel says meaningful withdrawal cannot occur before genuine disarmament. Previous efforts have repeatedly collapsed around this sequencing problem.
Both sides can accuse the other of delay. Both sides can reject proposals or dispute implementation. But Hamas possesses a particular strategic advantage: It does not need to produce peace in order to claim success. It needs to remain alive, armed, relevant, and capable of rebuilding.
Every temporary ceasefire that leaves Hamas intact can be presented as proof that Israel failed to destroy it. Every prolonged negotiation gives the organization more time to reorganize politically, pressure mediators, manipulate international opinion, and turn the continued captivity of Israelis into bargaining leverage.
The negotiations may appear to be about ending the conflict. For Hamas, they are also about extending the organization’s lifespan. The same is true of the Iranian regime.
Western governments tend to assume that both sides in a negotiation want the negotiation to succeed. That assumption is often wrong. Sometimes one side wants an agreement while the other side wants a process. An agreement creates obligations. A process creates time.
Time allows international pressure to shift. Time allows military forces to recover. Time allows alliances to fracture. Time allows public attention to fade. Time allows elections to approach. Time allows energy prices, economic anxiety, and political exhaustion to weaken the other side’s determination.
The United States wants an answer. Iran wants another meeting. The United States wants a final document. Iran wants another framework. The United States wants the Strait of Hormuz reopened. Iran wants the world to accept that its opening is negotiable. The United States wants Iran’s nuclear threat eliminated. Iran wants another 60 days to discuss what “eliminated” means.
This asymmetry is especially dangerous for U.S. President Donald Trump, who genuinely believes in using overwhelming pressure to produce rapid agreements. That instinct can be effective when the other side believes delay will make its position worse, but Iran believes the opposite.
The regime sees Trump’s hunger for a visible deal as something to exploit. It understands that he wants the dramatic announcement, the capital letters, the breakthrough, the photograph, and the declaration that a war has been avoided. Iran can feed that appetite with the outline of a deal, then the parameters of a deal, then the framework for implementing the parameters, then technical negotiations over the framework, then a temporary extension while the technical negotiations continue.
Trump announced this weekend that he would hold off on new attacks, subject to the rapid completion of an agreement reopening Hormuz and ending Iran’s nuclear threat. Iran, however, immediately separated its talks with Oman over shipping routes from the larger question of whether the strait would actually be fully opened. Washington heard “deal.” The Iranian regime heard “more time.”
The Strait of Hormuz should not be reopened for 60 days as though Iran is doing the world a favor. Permanent freedom of navigation must be treated as the baseline, not as a recurring Iranian concession. Deadlines must carry automatic consequences. Violations must trigger predetermined costs rather than another emergency conference to determine whether the violation was sufficiently serious.
Most importantly, the same obligation must not be purchased repeatedly. Iran should not be rewarded in June for reopening the strait, allowed to challenge the arrangement in July, and then rewarded again in August for reopening it once more. That teaches the Iranian regime that violating an agreement increases the value of its next agreement.
A successful deal must change the underlying reality. It must leave Iran with less ability to threaten shipping, rebuild its nuclear program, finance its proxies, or manufacture another crisis. Otherwise, it is not a deal. It is an intermission.
Donald Trump wrote “The Art of the Deal.” The Iranian regime has answered with “The Art of the Deal(ay).” It creates urgency, offers temporary relief, delays the decisive questions, collects immediate benefits, violates the ambiguous provisions, and then returns to the negotiating table demanding compensation for restoring what it had already promised.
The only way to defeat that strategy is to reverse its central calculation: Delay must stop protecting the Iranian regime, and delay must start costing it.
I have to admit, this is probably the most frustrated I've ever been with President Trump. I supported him, I voted for him, and I still believe he's been the strongest American president for Israel and the Jewish people in my lifetime.
But I simply don't understand the strategy with Iran. It seems to be one ceasefire after another, one extension after another, one negotiation after another. I keep asking myself: what exactly does he think is going to change?
The longer this drags on, the more it seems to play into Iran's strategy. Every delay gives the regime more time. They don't have to win—they just have to outlast the current administration and hope that after 2028 they'll be dealing with a president who is less willing to confront them. That's exactly the concern your article raises.
I understand that President Trump wants the best possible deal, and I respect that instinct. But after so many temporary agreements, ceasefires, and renewed negotiations, there comes a point where repeated delays begin to project weakness instead of leverage. I sincerely hope I'm wrong, because I want him to succeed, but I find this increasingly difficult to understand.
Iran is refinancing the crisis. Beautifully said Joshua! I fear the United States has lost the will to win a war in favor of a “deal”. Instead, we settle for vague MOUs. When are we going to learn that you cannot negotiate with a fanatical regime driven by religious apocalyptic fanaticism? World War II showed us the way to win a war and achieve lasting peace. It was not the tactic of let’s make a deal.