A month into bombing Iran, Donald Trump is learning what every general since the Prussian era already knew: plans don’t survive first contact with the enemy. The difference is that Trump seems to have skipped the planning part entirely.
When the US and Israel launched their initial strikes on February 28, killing Iran’s Supreme Leader Ayatollah Ali Khamenei and his closest advisors, the expectation was simple. A quick victory. Maybe even a popular uprising that would topple the regime. Instead, the Islamic Republic is still standing, still fighting back, and Trump is discovering exactly why his predecessors treated the idea of a voluntary war with Iran like a third rail.
The regime in Tehran didn’t crumble. Four weeks in, with 1,464 Iranian civilians dead according to human rights monitors, the government apparatus is functioning smoothly. No mass protests. No collapse. Just a ruthless, well-organized adversary that was forged in eight years of war with Iraq and built on institutions rather than individuals.
The Planning Problem
Dwight Eisenhower said something that should be framed in every war room: “Plans are worthless, but planning is everything.” He knew what he was talking about, having orchestrated the D-Day landings. The point wasn’t that plans matter. It’s that the discipline of making them, of thinking through contingencies and adapting when reality doesn’t cooperate, is what separates competent military strategy from improvisation.
Trump, by contrast, seems to be making this up as he goes. When Fox News Radio asked him 13 days in when the war would end, his answer was telling. He didn’t know. It would end “when I feel it, feel it in my bones.” That’s not strategy. That’s gambling.
His inner circle isn’t helping. These are people in jobs to back up decisions, not challenge them. Speaking truth to power apparently doesn’t fit the job description. This lack of real planning, this reliance on gut instinct and inner-circle yes-men, blunts the raw firepower advantage that the US military possesses. You can have the world’s most devastating armed forces, but without clear political direction, they become less effective.
The Geography Problem
Here’s what nobody planned for, or at least nobody planned well: the Strait of Hormuz. Iran controls this narrow entrance to the Persian Gulf, and they’re proving that geography can be a more effective deterrent than any military alliance. Around 20% of the world’s oil supply flows through there. When Iran’s Islamic Revolutionary Guard Corps tightened control, global financial markets went into a spin.
The beauty of it, from Iran’s perspective, is the asymmetry. The US and Israel can’t match Iran’s ability to close this waterway without capturing and occupying massive stretches of Iranian territory. That’s a level of commitment Trump clearly didn’t anticipate. Meanwhile, Iran can enforce control with cheap drones launched from hundreds of kilometers away in their mountainous interior.
General Sir Richard Shirreff, the former deputy commander of NATO, pointed out on BBC Radio 4 that any basic war game would have shown this outcome. Any competent planning would have included it. Apparently, someone skipped that exercise.
The Red Sea is next. The Houthis, part of what Iran calls the “axis of resistance,” just fired missiles at Israel for the first time since the February strikes. They have their own chokepoint to work with, the Bab al Mandab strait. If they resume attacks on shipping in that area, Saudi Arabia loses its western sea route. If they push further, cutting off the Asia-to-Europe route through the Suez Canal, you’re looking at an economic catastrophe that makes the current crisis look quaint.
Netanyahu’s Different War
Benjamin Netanyahu has thought about this war for four decades. He recorded a video statement from the roof of Israel’s military headquarters, speaking with actual clarity about war aims. He wants to damage the Islamic Republic enough to ensure Israel’s future security. That’s a regional power’s calculus, different from Trump’s much broader global challenges, but at least it’s a coherent one.
Netanyahu got what he wanted from Trump. A US president willing to go to war alongside Israel against Iran. Previous administrations, despite close ties between the countries, never wanted to go there. They believed containment was the answer. They thought the risks were simply too great.
They were probably right.
What Now?
Trump is at an inflection point. He could declare victory and say America has destroyed Iran’s military capability. Mission accomplished. That Iran’s control of the Strait of Hormuz isn’t his problem. That would tank world financial markets and horrify allies everywhere. A wounded, angry Iranian regime would have every incentive to keep squeezing the global economy.
More likely, he escalates. There are 4,000 US Marines on ships heading to the Gulf. The 82nd Airborne is on standby. The US could attempt amphibious landings on Iranian islands, maybe trying to capture Kharg Island, Iran’s main oil terminal. That would be difficult, dangerous, and risky.
Iran might actually welcome it. They want to drag the Americans into a longer war of attrition. They calculate their capacity for pain is greater than Trump’s.
The Real Issue
Trump’s biggest problem is that he and Iran have different definitions of victory and defeat. For the Iranian regime, mere survival is a win. They’ve survived far worse. Meanwhile, Trump seems to believe he can force surrender through military pressure and threats. The White House press secretary said Trump is “prepared to unleash hell” if Iran doesn’t accept defeat.
But here’s the thing: if Iran had actually been defeated militarily, the regime would have already collapsed. You don’t need to threaten someone who’s already beaten. Trump wouldn’t be threatening escalation if the war was actually over.
Arab diplomatic sources have told reporters that Iran was offering a path toward a nuclear deal when the US abruptly abandoned diplomacy. One source said “you know the Iranians were offering everything.” Maybe that’s an exaggeration. Maybe not. But it suggests there was room for negotiation when the bombs started falling.
The White House leaked a 15-point peace plan that reads less like a negotiation framework and more like terms of surrender. Iran countered with equally unacceptable demands, including recognition of their Strait of Hormuz control, reparations, and American base removal from the region.
Unless both sides find middle ground that doesn’t currently exist, a deal seems unlikely. But without one, Trump faces a choice between humiliation or escalation. Neither is appealing.
The Suez Moment
Back in 1956, the UK and France went to war with Israel after Egypt’s Gamal Abdul Nasser nationalized the Suez Canal. They achieved all their military objectives and were forced to withdraw by President Eisenhower. For Britain, it was the beginning of the end of their imperial dominance in the Middle East.
When historians look back on America’s competition with China to be the world’s dominant power, Trump’s poorly planned war against Iran might look like a similar waypoint. A moment when the US stumbled, when a leader confused military capability with strategic wisdom, when the costs of a war of choice became impossible to ignore.
The thing about learning from history is that you have to actually do the learning part first.
