Trump had to crush Iran instead of making deals. He didn’t — now he pays the price.

Last April, President Trump scolded Ukrainian President Volodymyr Zelensky on warfare. Trump told Zelensky, “When you start a war, you got to know you can win.”

That advice was inapt to begin with — Ukraine didn’t start the defensive war in which it is now engaged — but it has aged especially poorly.  

Trump started a war with Iran this February. Now, 201 days later, he is still trying to figure out how to win. And of course, knowing you can win a war is not enough. Training, preparation, overwhelming force and violence of action win wars. By the time the order is given to the military to fight and win, all probable outcomes must have been wargamed and branches and sequels developed to counter them.

Equally as important to knowing how to win is knowing the enemy, as Sun Tzu famously wrote. The enemy always gets a vote, but “you improvise, you overcome, you adapt.” You do not hit the pause button to see if the enemy has had enough yet or to make a deal. Momentum is a force-multiplier, and start and stop tactics are the enemy of momentum.

At the onset of Operation Epic Fury, the assumption Trump made was that Iranians would rise up and “take back their country” once the upper tier of Iranian leadership had been killed. They did not — not because they did not want to, but because conditions had not been set. Adm. Brad Cooper of U.S. Central Command repeatedly urged Iranian civilians to stay in their homes as U.S. and Israeli airstrikes targeted military infrastructure.

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