Trump made a catastrophic miscalculation — and the worst ones are still ahead

Donald Trump has always been the king of the colossal miscalculation, and 99 percent of the time not because of errors in strategy — because that word doesn’t exist in Trump’s brain. In there, miscalculations occur because of grotesque arrogance.

He miscalculated the New York real estate market badly enough to go bankrupt six times. He miscalculated the casino business, his business partners, his wives, and his friends, the heinous Jeffrey Epstein among them.

And now he may have miscalculated his approach to an entire civilization. Let’s call it what it is: a fury of epic miscalculations.

Trump’s decision to launch Operation Epic Fury (You see what I did there?) against Iran may go down as the most contemptible miscalculation of his long career, possibly in U.S. history.

The New York Times has reported in detail on the alarming breadth and depth of the miscalculations behind this war with Iran. It shows Trump, whose career is defined by a belief that he is always the smartest man in the room, now leading a room full of people who appear to have no idea what they’re doing.

The group that cooked up “Epic Fury” isn’t a room of seasoned strategists. It’s a room of yes men, blindly led by the would-be author of The Art of Miscalculation.

The absolute worst of the worst is Pete Hegseth, the Secretary of “War,” an in-over-his-empty-head TV personality whose favorite words appear to be “warrior” and “kill.”

Hegseth has never commanded a large contingent of soldiers in combat and has never run anything remotely resembling the Pentagon’s global war machine.

Marco Rubio, Secretary of State, has never negotiated a major international treaty or intervened in a war. He’s also serving as Trump’s National Security Adviser but he appears to have a third job: nodding yes every time Trump makes a boneheaded, critical miscalculation.

And who exactly is Energy Secretary Chris Wright? He spent his career in the oil industry making money first, second, and third. He is now out of his league. That became glaringly obvious when he said U.S. strikes against Iran would not cause long-term disruptions to global oil markets, according to the Times.

Collectively, Trump's advisers are the “Misanthropes of Miscalculation” — a brainless trust who clearly lack even a basic understanding of Iranian humanity and whose ignorance has led to disastrous assumptions.

Trump and his inner circle appear to have believed that a few airstrikes would somehow trigger the collapse of the Iranian government, and that the Iranian people would greet American bombs as celebratory liberation balloons.

Instead, Iran did what nations tend to do when attacked. It closed ranks, lashed out, and turned the war into a regional firestorm.

Iran has been ruled by religious fanatics for almost 50 years. That ideology is embedded in its political and social fabric. It doesn’t suddenly disappear because Trump thinks it should.

None of this should have been surprising.

Iran’s identity is built on resisting foreign intervention. The Islamic Republic has spent decades telling its people the United States is an imperial aggressor. With a bombs-away miscalculation, Trump handed them that narrative.

This is what happens when foreign policy is conducted by reckless people who treat history like something skimmed through CliffsNotes — if that.

To ignore the deep history of the region, its religious factions, and the extreme diversity of its people is to guarantee catastrophic miscalculation.

For nearly two weeks, the administration has struggled to explain what this war was supposed to accomplish. One day it was about nuclear weapons. The next, regime change. Then nukes again. Then “sending a message.” Then protecting Israel. Then an “imminent threat.”

Whatever the cause du jour is, Rubio usually says the opposite. Nobody knows what the hell is going on.

Meanwhile, the consequences have been exactly what any sober strategist would have feared, and what the miscalculator-in-chief apparently dismissed.

Iran responded not just by striking Israel and U.S. forces but by expanding the battlefield across the Middle East. American bases, embassies, and allies suddenly found themselves targets of Iranian missiles and drones.

Trump didn’t just miscalculate Iran. He miscalculated the entire region.

Did he think Iran would simply play dead? That it would not unleash retaliation across the Middle East? The assumption borders on strategic delusion.

And then there’s the global economy.

Iran’s threat to the Strait of Hormuz, the narrow artery through which roughly a fifth of the world’s oil flows, sent energy markets into panic.

The world, not just America, is now laughing at Trump’s promises to lower prices on “Day One” and end wars on “Day One.” Instead, he has delivered Day 11, and counting, of a war with costs far beyond Iran’s borders.

Trump promised there would be no American boots on the ground. But wars have an ominous way of ignoring false assurances, and already the language coming out of Washington has begun to shift.

The American public is rapidly losing patience. Polling shows a historic majority against this war, and it’s only going to get worse.

They see gas prices climbing. They see lives lost. They see incredible incompetence, and they are p—ed as hell. And they haven’t seen anything yet.

When Trump miscalculates this badly, he doesn’t reassess. He doubles down. He escalates. He looks for the next dramatic move that will prove he was right all along.

Every failure becomes someone else’s fault. Every setback demands a bigger gamble. If Trump’s past is any guide, the worst miscalculations are ahead.

• John Casey was most recently Senior Editor, The Advocate, and is a freelance opinion and feature story writer. Previously, he was a Capitol Hill press secretary, and spent 25 years in media and public relations in NYC. He is the co-author of LOVE: The Heroic Stories of Marriage Equality (Rizzoli, 2025), named by Oprah in her "Best 25 of 2025.”