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Donald Trump’s Iran Trap

The US president and Iran’s supreme leader, Ali Khamenei, are on a collision course.

michael_doran
michael_doran
Senior Fellow and Director, Center for Peace and Security in the Middle East
Michael Doran
President Donald Trump speaks during a visit to Fort Bragg in North Carolina on February 13, 2026. (Getty Images)
Caption
President Donald Trump speaks during a visit to Fort Bragg in North Carolina on February 13, 2026. (Getty Images)

For years, Donald Trump defined himself against the architects of the Iraq War. He cast Middle Eastern interventions as moral vanity projects paid for in American blood and treasure. He promised no more regime change. No more endless wars.

Yet as nuclear talks with Iran falter, American warships mass off Iran’s shores and bombers move into range. The president who rose by denouncing George W. Bush now finds himself reviving the logic of Bush’s Middle East policy.

How did we get here? More importantly: What does this moment reveal about American power—about what truly changes, and what never does?

The answer begins with the ambiguous outcome of last June’s 12-day war. Trump and his supporters—myself included—hailed Operation Midnight Hammer, which struck Iranian nuclear facilities, as a major military success. At the same time, Israel’s Operation Rising Lion dismantled Iran’s air defenses and severely degraded its ballistic missile capabilities.

On June 23, Trump cast the U.S.-brokered ceasefire as a triumph of American strength. On Truth Social, he declared that Israel and Iran had come to him “almost simultaneously” seeking “PEACE!” because “the time was NOW.” He promised “LOVE, PEACE, AND PROSPERITY” for both. The next day, his envoy Steve Witkoff spoke of a “long-term peace agreement that resurrects Iran” and delivers prosperity—one that would go “beyond even the ceasefire.”

Trump’s theory of victory was straightforward: The strikes had hurt. Iran had been forced back to the table. Military pressure would now yield diplomatic results. The desire for economic recovery among Iran’s elite would temper ideological rigidity.

But Supreme Leader Ali Khamenei offered a dramatically different theory. Two days after the ceasefire, in a televised address, he declared that the Islamic Republic had won. Through missile strikes on the U.S. Al Udeid base in Qatar, Iran had delivered “a severe slap to the face of America.” The United States, he claimed, had “gained nothing.” The attacks on Iran’s nuclear facilities had “done nothing significant.” America, he argued, intervened only to prevent Israel’s collapse.

Americans dismissed Khamenei’s remarks as bluster. To be sure, he and other officials exaggerated Iran’s successes and downplayed its losses. Their immediate priority was regime survival—preventing unrest, suppressing dissent, rooting out Israeli spies. Anything short of triumphalism would have signaled weakness. But there was more than bluster in their claims.

Itai Brun, the former head of research in Israel’s Military Intelligence Directorate and one of Israel’s most incisive analysts of Iran and its proxy network, has long argued that Tehran’s “theory of victory” is indispensable to understanding its conduct. His framework directs attention to four core claims the regime has advanced since last June’s war—claims that, taken together, amount to a coherent doctrine of victory.

First, the regime endured. Khamenei—and indeed, Iran’s proxies—measure success in continuity. If the regime survives intact—if the supreme leader remains in power, if missile production continues, if nuclear know-how remains in place—then Iran has not lost. Survival equals victory.

Second, Iran fought the United States, the greatest power on Earth, yet it was Washington, not Tehran, that called for a ceasefire. Tehran never formally accepted it; it simply stopped shooting. The regime therefore presents Washington’s use of Qatari intermediaries to seek a cessation of hostilities as proof that Trump blinked. As one Iranian military commander put it bluntly: “If Trump asked for a ceasefire, it wasn’t because of his strength—it was because he was genuinely afraid.”

Third, Iran’s missile strikes inflicted serious damage on Israel. They punctured the aura of Israeli invulnerability and caused significant harm to critical infrastructure, much of which Israel has kept from public view.

Fourth, knowledge cannot be bombed away. When Trump declared Iran’s nuclear program “obliterated,” Khamenei’s response was contemptuous: “Very well, let him keep imagining.”

Trump understands better than any of his predecessors that Iran’s nuclear program, missile arsenal, and proxy network are instruments of regional domination. Where he has miscalculated is in assuming that visible shows of force would quickly produce compromise.

Iran operates on a different theory of war. It celebrates steadfastness. Civilian deaths and military losses are tragic but acceptable. Time is an ally. Conflict with the United States is not a technical dispute to be solved through compromise but a prolonged ideological struggle. No single round is decisive.

Recent protests did not soften Khamenei; they hardened him. The more pressure the regime feels at home, the greater the danger of appearing weak abroad. Concessions risk signaling vulnerability not only to Washington but to Iran’s own streets. In an authoritarian system built on fear and ideological resolve, external compromise can accelerate internal unraveling.

Khamenei also believes he can outlast Trump. He sees American polarization, war fatigue, and coalition fragility. He notes major regional powers—Saudi Arabia and Turkey—urging restraint in Washington. He observes the strain on U.S. interceptor stockpiles. He understands that China benefits from Iran’s ability to tie down American forces and therefore works quietly to strengthen Iran’s ballistic missile capabilities.

For Khamenei, the struggle over missiles, proxies, and nuclear capability is existential. Concessions risk unraveling the regime’s deterrent posture, internal authority, and strategic partnership with Beijing. He prefers confrontation, betting that Iranian endurance will outlast American patience.

This calculation leaves Trump in a strategic vise. If he pursues regime change outright, he risks repeating Bush’s mistake of open-ended transformation. If he repeats the June model—delivering a severe blow but leaving Khamenei in power—the Islamic Republic will again declare victory, rebuild its missile and nuclear programs, and wait out the political clock in Washington.

Is there a way to square the circle?

The political objective of American military coercion must be stated clearly and pursued relentlessly. There are no visible fractures in the Iranian security establishment, and Khamenei rules with an iron fist. Yet there are divisions within the broader elite. Former president Hassan Rouhani has argued for an “Iran First” course—domestic reform, economic recovery, political liberalization, and reduced confrontation with the West. He has warned that the regime “should not silence people and should instead implement reforms so that the population does not seek foreign intervention,” and he has urged efforts to “mitigate tensions with the United States.”

Rouhani does not control the system. But his platform exposes a fault line that Washington can exploit.

President Trump should make clear that military operations will not cease until the political structure enforcing rigid adherence to Iran’s current strategy is reformed. That means, first and foremost, the abdication of Ali Khamenei. The supreme leader and his immediate family must leave the country. A caretaker government—led by Rouhani or a similar figure willing to pivot toward internal reform and external de-escalation—must assume authority.

Any transitional authority must publicly accept clear terms: no uranium enrichment; strict limits on ballistic missiles; an end to military and financial support for regional proxies; and the release of political prisoners.

If Khamenei remains in power, regime survival will equal victory, and compromise with America will be synonymous with defeat. A policy that seeks to soften him rather than remove him simply invites another “victory” in Tehran.

Read in The Free Press.