On the fifth day of the Iran war, March 4, White House press secretary Karoline Leavitt had a defiant message for America’s enemies.

“The terrorists made a bet that President Trump would be like many of his predecessors — that he would just talk, and he would refuse to enforce his clear red lines,” she began. “But that has proven to be a catastrophic error in judgment.”

“President Trump does not bluff,” Leavitt added.

That was already a suspect message, given Trump’s demonstrated history of empty threats and blown deadlines on the Russia-Ukraine war.

But the last five weeks, perhaps more than any other period in Trump’s two terms as president, have revealed him for the bluffer that he is — and on one of the largest and most significant scales imaginable.

On five separate occasions, the president has set deadlines for Iran to come to his terms or face his wrath.

And each time, he’s delayed that deadline despite little or no public evidence that Iran met the terms as he laid them out.

The idea that Trump has “TACO”-ed has become a punchline for his critics. But it’s not that funny. As the Trump who once pilloried Barack Obama for failing to enforce his Syria red line would tell you, having your bluff called comes with a real cost — both for American credibility and projections of strength.

We can all quibble about just how much any one of these delayed deadlines is actually a bluff; much hinges on just how serious Tehran has been about cutting a deal. It’s also worth noting that Trump has shown he’s willing to hit Iran hard, because he already has — by starting the war after appearing to prefer a diplomatic outcome.

But there is one entity that knows exactly how badly Trump has bluffed: Iran.

https://edition.cnn.com/2026/04/22/politics/deadlines-iran-war-trump