Trump is failing at the business of war

Mar. 16, 2026, 7:49 PM EDT

ByNicholas Grossman

The Iran was is exposing President Donald Trump’s unfitness for national leadership. The lie-filled bluster and escalation he relied on to succeed in business and domestic politics aren’t workingand the situation is out of his control. The world is interconnected and other people get a say, including oil companies and energy markets. But Trump never understood that, and since he has no other moves, he’s kept doubling down despite no plausible path to victory, making things worse.

With Venezuela, Trump said he attacked to take oilequating his personal rapaciousness with national interest. After U.S. special operations forces ousted Venezuelan president Nicolas MaduroTrump found the rest of the Venezuelan regime more pliable, including now-interim President Delcy Rodriguez, and told U.S. energy companies to go get Venezuela’s oil.

Except those companies didn’t want it. Which shouldn’t have been a surprise. Venezuela’s oil deposits are dirty, needing considerable refinement, and drilling isn’t profitable unless oil is priced higher than it was at the time. The infrastructure is poor, and U.S. companies would have to spend billions developing it. And the security situation was volatile after the U.S. military overthrew the national leader. Oil is flammable, and platforms would be a target if an insurgency develops.

But apparently it was a surprise to the White House. Trump berated energy executivesbut that didn’t work. They won’t throw away money just because he told them to.

With the Iran war, Trump is trying to bully not only energy companies, but the entire global energy market. Except the war is disrupting supply, making prices rise no matter what he says.

Trump ordered the U.S. military to attack Iran, and hasn’t articulated a clear goalbut did issue existential threats. At various times he’s called for regime change, told Iranians to overthrow the government, and demanded “unconditional surrender.”

And this comes after Trump reneged on the Iran nuclear deal without cause in his first term. That showed Iran that the United States in general, and Trump specifically, cannot be trusted to honor any agreement, and will react to concessions by demanding more.

In response to the U.S.-Israeli attack, Iran played its biggest card, closing the Strait of Hormuz. It’s a narrow choke point at the end of the Persian Gulf, and a kink in the waterway leaves it exposed to a lot of Iran’s coastline. About 20% of the world’s oil passes through Hormuz, and it isn’t hard for Iran to stop the traffic.

Iran can’t prevent U.S. and Israeli forces from flying over the gulf, and they probably couldn’t keep the U.S. Navy out of it, but to close the strait, they don’t need to. They only have to make shipping companies afraid to sail, and insurance companies think the risk of insuring the ships is too high. With threats, a few attacks on tankers, and now possibly sea mines, Iran has.

Again, this shouldn’t have been a surprise. For example, “Closing Time: Assessing the Iranian Threat to the Strait of Hormuz” by Caitlin Talmadge appeared in the leading journal International Security in 2008.

To address this crisis of his own making, Trump tried saying the war is almost over and the U.S. already won. It made the oil price drop back down for a bit, but as U.S.-Israeli bombardment continued and market disruptions got worse, it rose again.

Trump tried telling ships to traverse the Strait of Hormuz, but most wouldn’t, and a few who did exploded, presumably at Iran’s hand.

He tried releasing oil from America’s strategic reserve, and some other countries did from theirs. But that’s a Band-Aid on a gaping wound, and had little impact.

Then he tried bombing Kharg, an island in the gulf that Iran uses for oil exports. The apparent logic is that hindering Iran’s shipping will get Iran to stop blocking everyone else’s.

That recalls one of Trump’s go-to moves in business: the bad faith lawsuit. He’d break a contract, screw someone over, and dare them to sue him. Or would initiate legal action himself. Either way, he bet that he’d have more resources and greater tolerance for a protracted legal fight, and the other party would settle even when the facts were on their side.

That won’t work with Iran.

By making the threat existential, Trump set the bar for the Iranian regime at survival, and incentivized them to use whatever leverage they have. America’s military can overwhelm Iran’s, and is doing a lot more damage to Iran than the Iranians can do back. But even without its main source of revenue, Iran can keep up a defensive war for a while. Especially since the only thing it really needs to do is keep getting some shots off, such as with relatively cheap, domestically-produced Shahed dronesor small boats laden with explosives. The U.S. probably can’t stop that by force without a large ground invasion and indefinite occupation of Iran’s gulf coastline—a massive, costly undertaking—and maybe not even then.

Much of the time when Trump was in the private sector and messed up, his rich dad bailed him out or he’d declare bankruptcy. Instead of holding equity or debt, Trump would have the business pay him a salary and bonusesso that money was gone when the company went under, and his partners and contractors would take most of the losses.

When Trump stiffed lenders, there was usually someone else he could get to give him money. That’s how the Trump Organization ended up with a lot of Russian financing — by that point, just about everyone else wouldn’t touch him.

Now he’s done that to America. After a year of Trump denigratingthreatening, and tariffing U.S. alliesno one is willing to help rescue the U.S. from a mess of its own making, no matter how much he browbeats them.

Trump started something that quickly spiraled and seems out of ideas. There’s no one to sue, no rules to manipulate, just the hard realities of resource shortages and war.

And there’s a good chance Iran can tolerate being bombed more than the U.S. can tolerate a rapidly rising oil price and the economic damage it causes.