How Iran Goes Wrong

The strikes were justified but the hardest part is just beginning.

I commissioned the strategic case for intervention in Iran last week. I happen to agree with the premise—Iran is a de facto adversary, intervention is consistent with the National Security Strategy, and they were invested in a path which would make them a permanent and powerful force against U.S. interests. I think Trump was right to invest heavily in both diplomacy and military action when diplomacy failed.

That being said, we must be honest about the ways this could fail. By my observation, many Iran critics are caught in a quagmire of either the irrational or the irrelevant. No, Iran poses no meaningful military threat to us. There is no way they can defeat our military, short of some pyrrhic symbols like expensive radars and limited American casualties. No, Iran is not winning some complicated 4-d chess. They planned for this war, but planning and execution (and the ability to do something about it) are two different things. Finally, no, Trump is not likely to allow us to commit to a protracted ground invasion. The logistics are too difficult, the risks too high, and his entire administration understands the political reality. I wouldn’t be surprised if CIA or special forces were on the ground working with dissident factions, but a real invasion the likes of which is vehemently opposed by the pundit class is unlikely.

A number of anti-war voices aren’t even approaching the conversation from the angle that intervention will fail. Some people are arguing that Iran was never really the enemy. This is either naive or a rhetorical evasion, because admitting Iran is a definite adversary means admitting that some kind of response is just and necessary, and these people would rather relitigate the premise than face reality.

But there are two ways Iran could go deeply wrong. One is very dramatic, the other is quiet, more probable, and in some ways worse.

The dramatic risk is that Iran becomes a failed state. We bomb the regime into total collapse. No successor emerges, we don’t allow it to happen because we bombed every possible leader. The IRGC fragments into regional factions and power centers. The opposition is too weak, uncoordinated, or disunited to govern or even attempt to seize power.

And into this vacuum steps everyone with an interest. Russia, with deep military and intelligence ties to the Iranian security apparatus, backs whichever faction preserves their regional influence. China, Iran’s primary oil customer, backs whichever faction keeps the energy spigot turned on. We back whoever promises to give up the nuclear program. Azerbaijan masses on the border, the Kurds move, every small player with an interest mobilizes to take advantage. A country of 90 million with huge oil reserves becomes a multi-front proxy competition between three great powers and every possible regional actor.

Not like Libya, or even Syria—bigger, richer, and with both China and Russia at the table. This is a real possibility, and something that anyone seriously considering the war must be concerned with.

We're already seeing early signs. The IRGC publicly overruled President Pezeshkian this weekend after he stated Iran would not attack neighboring countries. The IRGC issued a statement calling his comments 'a mistake' and 'demonstrated' this by striking Dubai and Abu Dhabi. The civilian government no longer controls the military. If the regime falls, this is the faction that remains—the one with the guns and apparently the authority to override the president.

All that said, this probably doesn’t happen. Iran is much more durable as a nation than Syria. Total fragmentation assumes fault lines comparable to other sectarian divisions in the region. Iran's are real but less severe. More importantly, Trump seems to have no intention of truly occupying the country, and his administration seems to be broadly against it. Without an occupying force catalyzing the conditions for factional warfare, like Iraq, the most likely postwar dynamic is not collapse but something more ambiguous and more frustrating.

The probable losing scenario is that nothing changes. The boring one. The military campaign succeeds on every tactical metric. Missile infrastructure, navy, nuclear facilities, and every tangible tool for external power projection are destroyed convincingly.

Trump, perhaps rightly, declares victory and we all celebrate as the news cycle moves on. Then, quietly, the status quo reconstitutes. The IRGC’s networks, multi-decade infrastructure, and institutional knowledge remain intact. A covert nuclear program begins again. Proxy networks, damaged but not eradicated, rebuild over a few years. New leadership emerges from the middle ranks that is no less dedicated or hostile to our interests.

Five years from now, we’re looking at the same Iran. Weakened in some ways but deeply humiliated and with a specific grievance against the U.S. and the West that makes the previous few decades look restrained.

The mechanism that produces quiet failure is the trap of declaring premature victory. Trump has every domestic incentive to end this quickly—before the midterms, before gas prices shoot too high, and before the base that supports him begins to label his administration and his future likely successors as incompetent warmongers.

Trump has to thread a needle: he needs to change the country without destroying it. His military advantage, excellent at destruction, can only create some of the conditions required for change. He realistically cannot utilize American forces more than he already is—remote war, limited troops on ground. The factions on the ground that would form a new Iran, or at least pressure the old regime, must be assertive and soon.

Every American military intervention in my generation has succeeded militarily and failed strategically. We can hit our targets, but the aftermath of the bombs leaves something worse or indistinguishable from what existed before. Destroying a regime’s capability is not the same as solving the problem it represented.

Trump has been smarter about this than his predecessors. He shows no real desire to occupy and nation-build—he oscillates between “give me a government to work with” and “Iranian people, take back your country.” The lesson to focus on is the gap between refusing to occupy and having a plan. Trump could succeed in every way that disproves the Twitter doomers—and he likely will—and still fail to win strategically. This is what we must be wary of.

The strikes were justified and the strategic logic is sound. The military execution has been extraordinary. The dramatic risk is that Iran becomes a failed state with great-power proxy competition. The probable risk is quieter and in some ways worse—that the regime absorbs the blow, makes some concessions, and reconstitutes behind a curtain while we move on and a new President takes office.

The administration has genuinely earned our trust. They have shown tremendous strategic depth on foreign policy and the military campaign has been run as well as it realistically could have. It has not earned trust on the aftermath, and likely will not until the dust settles, because there is no credible aftermath we can be certain of.

Trump learned the right lessons from Iraq. Avoid occupation and don’t invest in unrealistic nation-building projects. But the space between those lessons and an actual plan for what comes next is where every American intervention has gone to die. Not occupying is only half of a strategy.