The Regime that Couldn't Read the Room

Over the last three days, the United States and Israel have killed Iran’s Supreme Leader, gutted the IRGC’s top command structure, and pushed the Islamic Republic itself closer to collapse than at any point in its nearly five decade history. In the hours after the strikes landed, the regime’s response—of launching missiles at the very countries that had been working for months to prevent the attack on Iran—underscored just how badly Tehran’s strategizing had gone.

But this isn’t the first time that Tehran has been misreading its own position—for years, it’s been overestimating what its proxies could deliver, overestimating how much patience Washington had left, and underestimating the extent to which the Trump administration was willing to go to enforce what it sees as American interests.

Stuck in 2015

Looming large over the negotiations here was the 2015 Joint Comprehensive Plan of Action, or JCPOA, which was the landmark agreement between the P5+1 and Iran regarding Tehran’s nuclear program.

By almost any measure, the deal was an extraordinary win for Tehran: they accepted temporary caps on their enrichment activities and agreed to IAEA monitoring, but the restrictions came with built-in sunset clauses that would begin to phase out after 10 to 15 years. The regime would retain the majority of its enrichment infrastructure, just under seal from the IAEA—meaning that the concessions were, inherently, reversible as soon as they sunset.

The logic behind this was based heavily on the liberal institutionalism outlook of the era: if you could bring Iran back into the international community, normalize relations slightly, loosen sanctions, it would begin to feel the benefits. Presumably, it would see the errors of its historically militant ways, and focus on economic development from then, on—especially through working with the alleged “moderates” like then-Iranian President Hassan Rouhani.

The regime, for years, appears to have believed that achieving something along the lines of the original JCPOA was still on the cards. And not for nothing, they came close to resuscitating a modified version of the original deal: by March 2022, a near-finalized text was on the table in discussions based in Vienna.

One key holdup during these discussions was that Iran insisted that any new deal include guarantees that no future American president could withdraw the way Trump had back in 2018. It made sense for them to be concerned about a potential collapse again should a second Trump term be in the cards, though such a demand was both something of a poison pill as well as unenforceable. There simply is no legal way to force the US to stay in an agreement reached without Congressional buy-in. Even with Congressional approval, the wide-reaching executive power of the presidency can largely override many treaties if it so chooses. Iran was demanding something the US structurally could not provide.

While that back and forth dragged on, Russia’s invasion of Ukraine upended global priorities. By the time that the Mahsa Amini protests kicked off later that year, Biden was extremely reluctant to be seen as offering Tehran a lifeline, especially as the regime appeared to be helping Moscow wage its war. The deal was dead, again.

The lesson that Tehran learned from this wasn’t that this was off the table permanently, though—they had come within pages of replicating the 2015 deal, complete with sanctions relief and economic integration with the global community. The failure to secure it, as far as the regime’s diplomatic class was concerned, had been caused by pushing slightly too far at a time when external disruptions had weakened their hand. Fundamentally though, nothing had changed: hold firm, keep enriching, and the Americans will eventually come back for another round of discussions.

Masoud Pezeshkian, who ran as a reformist, wasted little time in stacking his cabinet with JCPOA-era veterans, including making the chief diplomat behind the deal, Mohammad Javad Zarif, his Vice President for Strategic Affairs, and long-time negotiator Abbas Aragchi his foreign minister. The strategy wasn’t exactly ambitious: they wanted back in the deal, even if they would occasionally play this dynamic down in order to make it appear that they were willing to hold out for a better offer.

Not even the Twelve Day War in June 2025 managed to shake this conviction, which should really underscore how profoundly transformative the JCPOA was for the regime’s mindset. At the time, Israel wanted to continue their air campaign and put maximum pressure on Tehran—but Trump called it off, insisting that diplomacy be given a chance. The strikes, in his mind, should serve as a wake-up call that times had changed, and that the Islamic Republic wasn’t in nearly as strong a position as it had previously believed.

The negotiations, however, didn’t go anywhere productive. Tehran held a hard line almost identical to the one that had produced the original JCPOA: Aragchi and Pezeshkian insisted that the discussions remain strictly nuclear. Missiles were off the table, as was Tehran’s desire to rebuild its now-shattered Axis of Resistance. In fact, during the second round of negotiations, Aragchi went further: he explicitly stated that Iran was seeking terms superior to what Obama had offered, all while negotiating from a position that was, by every measurable dimension, weaker than the one they’d held in 2015.

So by the end of February when Iran rejected key parts of the US’ demands, they thought that they could stall for time. Two days later, the bombs fell.

Paper Tigers

The natural question all of this raises is what, exactly, Tehran thought it could achieve given just how much had changed. The JCPOA-era playbook had always rested on a specific set of assets that gave them leverage at the negotiating table: a proxy network capable of threatening retaliation across multiple fronts, a nuclear program advanced enough to create urgency, and weariness inside the US about getting bogged down in another long-term Middle East conflict.

Chief among Iran’s proxy forces has been Hezbollah—for years, the implicit threat was that any move against Tehran would trigger an absolutely devastating barrage from Southern Lebanon into northern Israel. And while Jerusalem had made strides in shoring up its missile defense systems, the scale here would almost certainly have overwhelmed their best equipment. Combined with what were supposed to be simultaneous attacks from Hamas in Gaza, it functioned as an effective blackmail umbrella.

Israel’s 2024 campaign more or less shattered that strategy in a matter of weeks. Hezbollah’s leadership was completely wiped out, roughly half of their precision rockets were destroyed, and they ultimately accepted a ceasefire deal that was tantamount to surrender. This was made all the worse by the collapse of Assad’s Syrian regime in December that year, which cut off a critically important supply line from Iran to Lebanon that had long been used to build up Hezbollah’s missile stockpile.

Now, that’s not to say that Tehran was left empty-handed as 2025 began. Its missile arsenal remained capable and one of the most advanced in the region, even if they weren’t very effective against Israel’s missile defense systems during Operation Rising Lion last summer. And the regime had also spent years cultivating great power partnerships that it believed would cast a deterrence shadow large enough to make American strikes much less likely, if not impossible.

The architecture of it all looked impressive, at least on paper: a 25-year strategic agreement with China and a 20-year partnership with Russia, formalized in January 2025, that together were supposed to signal Iran was no longer isolated.

Now, the regime wasn’t delusional enough to expect that either Beijing or Moscow would be sending troops to the frontlines in case of an all-out war, but it did believe that there would be substantial benefits of having their backing. Russia sent both personnel and hardware to back up Assad in 2015, which proved to be incredibly effective at the time, so it wasn’t exactly unthinkable that either of these powers would step in to some extent to prop up the Islamic Republic.

Suffice it to say, neither did. When the Twelve Day War began, Iran’s allies issued tough statements, and little else All this should have prompted some serious reflection in Tehran: the partnerships they had spent years cultivating were worth about as much as the paper they were printed on the moment that actual military force entered the equation. And yet even still, heading into these latest rounds of negotiations, the regime showed no indication of having absorbed that lesson either.

Repaid in Missiles

While Iran didn’t exactly have many friends across the region as 2026 dawned, it did have decent enough relations with several powerful Gulf states who were willing to go to bat for it diplomatically, urging the US not to take military action. This was in no small measure an act of self-preservation—five of the six GCC states host major US military installations, which - as we’ve seen these past three days - makes them prime targets for Iranian missile attacks. A full-scale regional conflict would almost certainly be catastrophic for them, as we appear to be finding out.

However self-motivated the intentions may have been, though, they nevertheless produced one of the most sustained diplomatic campaigns in modern Middle Eastern history: Qatar’s Emir coordinated with Trump via phone on de-escalation even as the carrier strike groups were already moving into position. Egypt, Turkey, and Qatar together presented both sides with a negotiating framework that attempted to bridge the gap between their positions, including proposed enrichment limits and missile constraints.

The UAE in particular had spent years carefully rebuilding its relationship with Tehran, and was actively invested in preventing the kind of conflict that would undo all of that. Perhaps most dramatically, Oman’s foreign minister flew to Washington and met with Vice President JD Vance at the White House on February 27th—the evening before the operation—in a final, Hail Mary attempt to avert it.

What made all of this so extraordinary in hindsight is that none of this appears to have even registered in Tehran as being a strategic asset worth protecting. The Gulf states were actively working to tone down Washington’s eagerness to strike, and even closed their own airspace to ensure that they would not be seen as assisting in any military action.

None of it mattered. In the hours after Operation Epic Fury killed Khamenei and destroyed major IRGC command centers across Tehran, Iranian ballistic missiles and drones shot off across the region, targeting all the Gulf states that had worked so hard to prevent a war. The IRGC declared that there were no remaining red lines and framed the attacks as self-defense against all American and Israeli assets in the region.

The missiles and drones that they launched didn’t discriminate between the military installations that might have justified the IRGC’s self-defense framing and the civilian infrastructure in their host countries. In Bahrain’s capital Manama, Shahed drones slammed into residential apartment high rises, while a falling missile landed in suburban areas just outside of Doha, Qatar.

The damage in Dubai was perhaps the most jarring. The UAE’s air defenses intercepted most of what came in, but the volume of the barrage meant that debris from destroyed missiles and drones literally rained down across the city. At the city’s airport, passengers filmed themselves evacuating smoke-filled corridors in panic, while explosions were filmed shockingly close to the Burj Khalifa, ultimately resulting in the Fairmont hotel catching on fire.

Over the last day, it’s come to light that segments of the IRGC that launched these attacks were reportedly relying on written orders that were distributed before the operation even began, in the event that communication with central command was severed. While not exactly controversial—militaries the world over have this sort of built-in failsafe—the fact that these orders existed as written at all is deeply telling about how Tehran’s political class viewed the region.

The people who drafted them had every piece of information that we do—and presumably, then some—needed to understand that the Gulf states were the single most effective constraint on American military action, and then produced plans to bomb them anyway.

Within 72 hours, the UAE had shuttered its embassy in Tehran and pulled every diplomat and staff member out of the country, citing unprovoked aggression against its civilians. The GCC’s unified condemnation named Tehran directly, and across the entire Arab world, the focus has largely been not on condemning Washington for its actions, but on Iran for its response.

Piecing It Together

The structural parallels to Russia’s 2022 invasion of Ukraine are difficult to ignore here. When Moscow sent tanks across the border, it might not have managed to accomplish a great deal within Ukraine—but it did accomplish something that decades of Americans complaining about European free riding wasn’t able to. The continent transformed from a defense-averse one into a unified military coalition practically overnight, with Finland and Sweden both applying to join NATO and Germany coming to terms with the flaws of previous Chancellors’ dovish foreign policy.

When historians eventually piece together how the Islamic Republic arrived at this point, they’ll find a regime that did something strikingly similar.

The proxy network that consumed tens of billions of dollars and decades of strategic investment was supposed to make a direct confrontation with Iran too costly to even contemplate—and for a long time, that strategy worked. But once that network was shattered, the regime’s negotiating posture should have changed with it, even if that was a difficult pill to swallow. Instead, Tehran walked into round after round of talks demanding terms more favorable than the ones it had secured back in 2015.

While we can’t say for certain what their motivation was here, it very plausibly could be that the “wait them out” approach had won the day before. Given how close they came to reviving the JCPOA in 2022, the regime’s diplomatic class appears to have assumed that if they couldn’t reach a sufficient deal with Trump, they could simply wait him out again—that Washington wanted a deal more than it wanted a war, and that sufficient patience would eventually produce one.

They were still negotiating on that basis when the bombs started falling.