When the world's at stake,
go beyond the headlines.

In August 1988, with his country bled white by eight years of war against Saddam Hussein’s Iraq, a million dead, the economy in ruins, the revolutionary generation exhausted, Ayatollah Ruhollah Khomeini accepted a U.N. ceasefire. He called it “more deadly than taking poison.” He was drinking from the bitter chalice of defeat.

And then what happened? The Islamic Republic survived. It did not moderate, liberalize, or reckon with its failures. It nursed its wounds, rebuilt its Revolutionary Guard, and spent the next three and a half decades constructing the very proxy network and missile arsenal that the United States and Israel are now trying to destroy. Khomeini’s humiliation became the seedbed of everything that followed.

Fourteen days into the American-Israeli air campaign against Iran, it is worth recalling that history — because we may be about to repeat it.

The opening strikes were, by any military measure, devastating. Supreme Leader Ali Khamenei is dead. Iran’s navy has been sent to the bottom. Its missile stocks are reportedly down by 90 percent, its drone capacity by 95 percent, although as Ukraine has demonstrated, this can be reconstituted in the face of relentless attack. The nuclear program, already set back by last June’s 12-day war, has been hammered further. From the air, the United States and Israel appear to have Iran in a vise.

But Fred Iklé, the defense strategist whose 1971 masterwork Every War Must End shaped Colin Powell’s thinking about the Gulf War, diagnosed the precise trap now yawning before Washington. Governments, Iklé observed, are remarkably adept at starting wars and dangerously inept at ending them. They plan obsessively for the first battle and almost never for the last. Military victory, he warned, is not the same thing as political resolution. Confusing the two is how wars that appear won become conflicts that never truly end.

The Trump administration has offered the Iranian people two contradictory visions of their future: a negotiated peace if they capitulate, or a popular revolution that sweeps the Islamic Republic away. Neither is likely. Iran’s new supreme leader, Mojtaba Khamenei, the slain leader’s son, appointed in the chaotic aftermath of the strikes, has no popular mandate, no clerical legitimacy (the younger Khamenei is neither a true mujtahid nor an authoritative jurist), and no path to survival except total dependence on the Revolutionary Guards and the language of national defiance. He will drink his own bitter chalice. And like his father’s mentor before him, he will survive it.

This is the scenario that deserves more attention than it is getting: not Iranian collapse, but Iranian persistence; wounded, revanchist, and ungovernable by the tools that won the war.

A severely weakened Iran can still do serious damage. It does not need a rebuilt navy or a functioning nuclear program to threaten global energy markets. Mines, shore-based missiles, and fast-attack boats are cheap and deniable. During the Iran-Iraq “Tanker War” of the 1980s, Iran disrupted shipping through the Strait of Hormuz even while losing on land. Today, with Iranian commanders already conditioning any resumption of tanker traffic on the withdrawal of American forces from the Gulf, the threat is explicit. Roughly 20 percent of the world’s oil passes through that strait. Persistent uncertainty about its reliability, not necessarily closure, but chronic insecurity, is itself a profound strategic weapon, one that costs Iran little to wield even as it costs its foes a great deal to counter.

Beyond Hormuz, Iran’s proxy network, though badly degraded, is not destroyed. Hizballah still has weapons and fighters. Shia militias in Iraq retain the capacity to harass American forces, as they are now doing, and pressure Gulf governments. A regime that cannot project conventional power will have every incentive to project asymmetric power; the kind that is maddening, deniable, and nearly impossible to deter through airstrikes alone.

And there is the nuclear question, which is perhaps the most dangerous long-term consequence of a war fought without a termination framework. The strikes appear to have significantly set back Iran’s enrichment capabilities. But a wounded, humiliated Iranian state governed by leaders who have just watched their supreme leader assassinated by Israeli bombs following American intelligence will not permanently abandon the idea of a nuclear deterrent. They will rebuild, covertly and patiently, toward the one capability that they believe will guarantee they can never be struck this way again. The strikes may have bought years but will not buy permanence.

Iklé’s third lesson — the one Washington most needs to hear — is that the conditions for a durable peace must be built into the war’s conduct, not improvised after the shooting stops. The Allied occupations of Germany and Japan worked not because the Allies bombed more effectively, but because they planned meticulously for what came after, embedding political and institutional transformation into the end-state from the beginning. It is worth recalling that the Roosevelt administration set up an entire organization to plan for a post-war Germany two years before U.S. troops crossed the Rhine.

There is no such plan visible in this war. President Donald Trump has said he will know it’s over when he feels it “in his bones.” A vibe, however, is not a strategy.

The bitter chalice is being concocted once again. The question is not whether Iran will be forced to drink it; presumably, they will. The question is what grows from the poisoned soil of that defeat. History’s answer, in 1988, was 35 years of mounting regional catastrophe. We should not assume the answer will be different this time simply because our airstrikes were more accurate.

Steven Simon is a distinguished fellow at the Davidson Institute for Global Security at Dartmouth College and senior research fellow at the Quincy Institute for Responsible Statecraft. He previously served at the State Department and National Security Council Staff. He is the author of Grand Delusion: The Rise and Fall of American Ambition in the Middle East.

Image: ChatGPT