In the latest episode of Critical Conditions, Claire and I took stock of the increasingly chaotic war around Iran — and reached a grim conclusion: something fundamental in the strategy has to change. The early optimistic on the side of the attackers — despite their massive military advantage — is fading.
The discussion began with Claire’s fury. In her view, the problem is not merely strategic miscalculation but Trump. Claire argued that his public statements have been erratic, inflammatory, and strategically disastrous. The United States, she said, has failed to articulate a clear war aim, a coherent message, or even a stable narrative about why the conflict is being fought.
She raised the possibility that Trump should be removed from office through the 25th Amendment, arguing that every time he speaks he undercuts the Western position and emboldens Tehran. I am no supporter of Trump, who is a national embarrassment, but I do not think that will happen.
Our conversation quickly moved to the strategic reality on the ground. And here we found ourselves largely in agreement. The war’s first days were, undeniably, spectacular. Israeli intelligence penetrated the Iranian regime at astonishing depth. Key figures were eliminated, including Supreme Leader Ali Khamenei. For a brief moment it looked as if the regime might be pushed to the brink.
But wars are not won in the first two days (except the Six Day War, which actually was). The central problem, as we discussed, is that the operation appears to have lacked a clear second phase. The decapitation strikes were effective — perhaps brilliantly so — but what followed has looked increasingly like a drift toward war of attrition. And that is precisely the kind of conflict Iran thrives on. Iran’s strategy seems clear: outlast Israel and the West (and make no mistake: no matter what weaselly leaders say, the entire West wants to free the Iranian people of their miserable ayatollah-murderers). .
Tehran cannot defeat the United States militarily. But it doesn’t have to. Its goal is to stretch the conflict until the political will of democratic societies collapses. Rising oil prices, global economic anxiety, propaganda campaigns, and regional escalation all serve that objective. The longer the war drags on, the more pressure mounts to pull back. This is the playbook the regime prepared over decades.
I assess there are now two strategic choices.
The first option, which Claire actually recommended, is to pause. That would mean halting major offensive operations, allowing tensions to cool, and attempting to force a renewed diplomatic process. The goal would be to bring Iran back to negotiations under immense international pressure — sanctions, diplomatic isolation, and the credible threat that military operations could resume if Tehran refuses meaningful concessions. Such concessions would have to be sweeping: abandoning nuclear ambitions, ending missile proliferation, dismantling proxy militias, and ceasing the regime’s brutal repression at home. But there is a problem with this option.
A pause could easily look like victory for Iran. The regime may come to the table more mulish than ever. It’s impossible to tell whether such an Iran would be chastened enough to not continue its regional jihadist project. Maybe it would, but probably not. Either way it would be devastating to the Iranian people, who will continue to be crushed.
The alternative is to double down — decisively and quickly. That would mean escalating the campaign to target every remaining pillar of the regime’s power structure: command nodes, Revolutionary Guard infrastructure, propaganda organs, and the individuals who run them. The goal would would be forcing the regime either to surrender or to fracture internally — or come to the table in an acquiescent state. And: definitely not allowing the war to drag on.
Neither option is great and both involve enormous risks. But what Claire and I agreed on most strongly is that the current path — drifting into an open-ended war without strategy — is the worst .
Iran, after all, is not simply reacting militarily. It is fighting politically and psychologically. With the internet inside Iran largely dark and information tightly controlled, propaganda is already shaping global perceptions of the conflict. Tehran’s leaders appear convinced they can ride out the storm.
And they may not be wrong. The real danger we discussed is that the regime could emerge battered but intact — able to claim that it survived the combined might of Israel and the United States. If that happens, the consequences would be severe: a more radical leadership in Tehran, a renewed rush toward nuclear weapons, and an emboldened axis of authoritarian states.
So something has to change. Either the war pauses and diplomacy returns under credible pressure, or it escalates quickly enough to force an outcome. What cannot continue is the current limbo — a war that began with breathtaking precision but now risks dissolving into a slow-motion geopolitical disaster.
