Wars are rarely lost first on the battlefield. They are lost in leaders’ minds − when leaders misread what they and their adversaries can do, when their confidence substitutes for comprehension, and when the last war is mistaken for the next one.
The Trump administration’s miscalculation of Iran is not an anomaly. It is the latest entry in one of the oldest and most lethal traditions in international politics: the catastrophic gap between what leaders believe going in and what war actually delivers.
I’m a scholar of international security, civil wars and U.S. foreign policy, and author of the book “Dying by the Sword,” which examines why the United States repeatedly reaches for military solutions and why such interventions rarely produce durable peace. The deeper problem with the U.S. war in Iran, as I see it, was overconfidence bred by recent success.
Dismissed concerns
Before the conflict involving Iran, Israel and the U.S. escalated, Energy Secretary Chris Wright dismissed concerns about oil market disruption, noting that prices had barely moved during the 12-day war in June 2025 between Israel and Iran. Other senior officials agreed.
What followed was significant: Iranian-aimed missile and drone barrages against U.S. bases, Arab capitals and Israeli population centers. Then Iran effectively closed the Strait of Hormuz, through which roughly 20% of the world’s oil supply passes daily − not with a naval blockade, not with mines or massed anti-ship missiles, but with cheap drones.
A few strikes in the vicinity of the strait were enough. Insurers and shipping companies decided the transit was unsafe. Tanker traffic dropped to zero, although the occasional ship has made it through recently. Analysts are calling it the biggest energy crisis since the 1970s oil embargo.
President Donald Trump expressed anger on March 17, 2026, at allies who did not agree to help the U.S. force the reopening of the Strait of Hormuz to tanker traffic.
Iran’s new supreme leader, Mojtaba Khamenei, has since vowed to keep the strait closed. U.S. Sen. Chris Murphy, a Connecticut Democrat, reported after a closed-door briefing that the administration had no plan for the strait and did not know how to get it safely back open.
With no embassy in Tehran since 1979, the U.S. relies heavily for intelligence on CIA networks of questionable quality and Israeli assets who have their own country’s interests in mind. So the U.S. did not anticipate that Iran had rebuilt and dispersed significant military capacity since June 2025, nor that it would strike neighbors across the region, including Azerbaijan, widening the conflict well beyond the Persian Gulf.
The war has since reached the Indian Ocean, where a U.S. submarine sank an Iranian frigate 2,000 miles from the theater of war, off the coast of Sri Lanka – just days after the ship had participated in Indian navy exercises alongside 74 nations, including the U.S.
The diplomatic damage to Washington’s relationships with India and Sri Lanka,