President Donald Trump walks toward Marine One as he departs the White House, on April 16.
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.
Let’s recap the threats, the deadlines and how Trump explained them away.
1. Date: March 21
Deadline set: March 23
Trump said Iran had to “FULLY OPEN, WITHOUT THREAT, the Strait of Hormuz, within 48 HOURS.” Otherwise, the United States would start striking its power plants.
2. Date: March 23
New deadline set: March 28
With about 12 hours to go, Trump announced a five-day delay. But rather than Iran reopening the Strait of Hormuz, as he had demanded, he instead cited “VERY GOOD AND PRODUCTIVE CONVERSATIONS” between the two sides.
There were two problems with that. One is that Iranian officials denied there were any negotiations at that point. And two was that Trump seemingly had 12 more hours to agitate for his actual demand. Instead, he announced the delay shortly before the financial markets opened up, soothing investors.
Trump said the new March 28 deadline was “SUBJECT TO THE SUCCESS OF THE ONGOING MEETINGS AND DISCUSSIONS.”
3. Date: March 26
New deadline set: April 6
Trump said he was adding eight more days to the deadline, citing an “Iranian Government request” for more time and talks that were “going very well.”
But a top Iranian official said there had only been an “exchange of messages,” not true negotiations. And the US ally in the war, Israel, suggested Iran wasn’t actually serious about negotiating.
Trump claimed at the time that Iranian officials were “afraid to say” how anxious they were to cut a deal for fear of being killed. But nearly a month later, there remains little evidence Iranian officials have ever offered major concessions.
In the days that followed, Trump set out the terms for the April 6 deadline.
The demand was that “a deal” be “reached” and the Strait of Hormuz be “immediately ‘Open for Business.’” If that didn’t happen, he would blow up all of Iran’s electric power plants, oil wells and Kharg Island — as well as possibly all of the country’s desalination plants. (It’s quite possible the things Trump was threatening here would be war crimes.)
He later added that he would “consider” a ceasefire if the Strait of Hormuz were “open, free, and clear.”
Trump re-upped the deadline on April 4, saying Iran had “48 hours before all Hell will reign down on them.”
4. Date: April 6
New deadline: April 7
Despite Iran not cutting a deal or opening up the strait, Trump gave it another day. He did so by citing Easter, even though it’s a holiday he would seemingly have been aware of when he set the deadline.
“I thought it was inappropriate the day after Easter,” he said. “I want to be a nice person.”
He said that if the Iranians didn’t meet the demands, “they’re going to have no bridges, they’re going to have no power plants.”
5. Date: April 7
New deadline: April 21
Trump announced a two-week ceasefire. But again, he didn’t say Iran had met his demands of cutting a deal or opening the strait. Instead, he again cited supposed progress in negotiations and a temporary agreement.
But key aspects of the ceasefire deal were quickly in dispute — including whether Israel had agreed to stop striking Hezbollah in Lebanon, what 10-point proposal was the basis for negotiations, and whether Iran could retain control of the strait.
Trump also said the ceasefire was “subject to the Islamic Republic of Iran agreeing to the COMPLETE, IMMEDIATE, and SAFE OPENING of the Strait of Hormuz.” That doesn’t appear as though it ever happened, but Trump continued with the ceasefire anyway.
6. Date: April 21
New deadline: Unspecified
Trump announced he would give Iran an unspecified extension to come up with a proposal for peace. But again, Tehran hadn’t cut a deal or opened the strait, as he demanded. And he didn’t even cite supposed progress this time.
Instead, Trump cited “the fact that the Government of Iran is seriously fractured.”
But then he undercut his own reasoning in the next clause by saying the leadership being fractured was “not unexpectedly so.” If this was predictable, then why the previous hard deadline?
Sources have told CNN that Trump intends the new extended deadline to be limited, but the White House said later Wednesday that he’s set no “firm deadline.”
“People say I want to get it over because of the midterms, not true,” Trump told Fox News’ Martha MacCallum on Wednesday, saying there was “no time frame” for ending the war.
And in extending the ceasefire, the president said it would continue not just until an Iranian proposal can be submitted, but also until “discussions are concluded, one way or the other.”
That all sounds a lot more open-ended.
There’s an argument to be made that extending the ceasefire is good for the world, in that it doesn’t plunge the Middle East deeper into war.
But you could certainly forgive Iran for concluding, at this point, that Trump simply doesn’t want to follow through on his threats. After all, he’s made extensions despite little or no public evidence that Tehran has met his red-line terms.
And there’s a certain someone who once wagered that this kind of bluffing damaged the negotiating posture of the United States.
After Obama declined to enforce his “red line” of taking military action against Syria if it used chemical weapons, Trump spent years hanging it around his and Hillary Clinton’s necks.
“When he didn’t cross that line after making the threat, I think that set us back a long ways,” Trump reflected in 2017, “not only in Syria, but in many other parts of the world, because it was a blank threat.
“I think it was something that was not one of our better days as a country.”
In his 2016 Republican National Convention speech, Trump called Obama’s red line a “humiliation” because “the whole world knew it meant absolutely nothing.”
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