Two Men's Hubris Ignited a War Neither Can Win

"On the eve of each war at least one of the nations miscalculated its bargaining power," historian Geoffrey Blainey once wrote. In his words, "every war comes from a misunderstanding. And every war is an accident."

The U.S.-Iran war—or rather, its latest and most dramatic iteration—grew from precisely such miscalculations between two men who couldn't be more different, yet share one fatal flaw. Donald Trump and Ali Khamenei both suffer from a vainglorious hubris that has warped their strategic judgment.

For Trump, this conflict represents the ultimate deal—a high-stakes gamble with the Middle East as his negotiating table. For Khamenei, whose compound became a target for airstrikes, it's something far simpler: a fight for survival.

The Dealmaker vs. The Survivor

Trump's hubris manifests as performative strength. Having built his brand on being the ultimate dealmaker, he finds military action more palatable than even the appearance of being out-negotiated. Khamenei's hubris stems from ideological rigidity—he views his theocracy as divinely mandated and has just overseen historic mass murder to secure his rule.

Trump has long approached geopolitics with an amateur's certainty. According to a 2016 New Yorker account, as far back as 1990, Trump offered unsolicited advice to a U.S. nuclear negotiator on handling the Soviets: "Arrive late, stand over the counterpart, stick a finger in his chest, and say, 'Fuck you!'"

He saw the complexities of enriched uranium and ballistic missiles as secondary to the theater of dominance. And in that arena, he believes he holds the upper hand against Iran—a view reinforced by his 2018 withdrawal from Obama's nuclear deal, his 2020 killing of Iran's top general, and his 2025 bombing of Iran's nuclear sites, all gambits that cost him little.

When Easy Wins Create Dangerous Expectations

The apparent ease with which the Trump administration replaced Nicolás Maduro with Delcy Rodríguez in Venezuela this January likely reinforced Trump's confidence. As General David Petraeus recently cautioned, just as the swift fall of the Taliban in 2001 fueled unrealistic expectations for regime change in Iraq, Maduro's lightning capture may have led Trump to believe such scenarios are easily replicable in Iran.

If Trump's hubris has been fortified by experience, Khamenei's has persisted despite it. Long after Iran's regional proxies and nuclear program had been significantly degraded by Israel and the United States, Khamenei continued speaking as one assured that God was on his side and the present crisis could simply be endured.

He dismissed the United States as a "corrupt, repressive, illogical," and "crumbling empire," citing Jeffrey Epstein's "evil island" as the sinister culmination of 300 years of Western civilization. Washington, Khamenei claimed, lacks the "staying power" for a true confrontation with Iran. More dangerous than any American warship, he recently taunted Trump, "is the weapon that can send that warship to the bottom of the sea."

Four Types of Misgovernment

Historian Barbara Tuchman once described four kinds of misgovernment stemming from a leader's hubris: tyranny, excessive ambition, incompetence, and "folly"—pursuing policies contrary to the nation's interests. Khamenei's Islamic Republic has checked every box. Despite decades of evidence of his worldview's failure, his belief in its righteousness remains unshaken. He appears more prepared to die a martyr than capitulate, his endgame reduced to the simple clarity of living to fight another day against America.

Trump exhibits the hubris of excessive ambition—if not for a specific outcome, then for his own ability to bring about epoch-making consequences. Yet the range of options he debated during negotiations—from broad diplomatic deals to military operations aimed at toppling the regime—suggested a man uncertain of his own appetite, torn between ordering a side salad or a 32-ounce tomahawk steak.

Even his choice of representatives—son-in-law Jared Kushner and Middle East special envoy Steve Witkoff—seemed better suited to part-time real estate negotiations conducted between rounds of golf. Trump's address to Iranian forces on the night of the strikes sounded like a closing argument across a negotiating table: "Lay down your weapons and have complete immunity. Or, in the alternative, face certain death."

Different Games, Different Stakes

For the Islamic Republic, this standoff is an all-consuming ideological war for both personal and regime survival. These represent two fundamentally different distortions of reality: one leader views the world as a transactional playground where everything has a price, while the other views his own survival as a world-historic necessity, regardless of the ruin it brings his people.

America's military superiority is overwhelming, but in this contest, it's not necessarily decisive. The two sides are playing for different stakes: Washington seeks transformative victory, while Tehran seeks only to survive. As Henry Kissinger noted of guerrilla warfare, the insurgent wins by not losing, while the conventional power loses by not winning.

In very few theaters do American values and interests converge as seamlessly as they do in Iran. A tolerant, representative Iranian state would both transform citizens' lives and fundamentally reorder Middle Eastern geopolitics toward stability and prosperity. But Washington has lately wavered in its commitment to those values, stripping itself of its most potent tools of influence.