President Donald Trump has repeatedly set deadlines in his second term — and repeatedly moved them — raising questions about whether his timelines are strategy or bluster.
Whether it’s five days, two weeks, or “very soon,” the pattern has surfaced across much of Trump’s second-term agenda, from tariffs to legislative fights to military operations in Iran and Venezuela.
Still, the frequency with which Trump issues timelines has experts and Trumpworld insiders questioning the true goals behind the latest instance. Some sources say the president’s timetable threats may have ulterior motives, like calming domestic and global energy markets, tempering the public’s souring perceptions of the war, or even obscuring a new offensive against the regime in Tehran.
One Trumpworld insider, a longtime, out-of-government adviser to the president, suggested to the Washington Examiner that Trump’s temporary ceasefire was simply a part of “the art of the deal.”
“Look, President Trump’s main concern regarding Iran is promoting peace, both for Americans and its allies. For decades now, Iran has been the largest, most brazen state sponsor of terror across the globe, and it’s not even close,” that person said. “I’d say that the way he’s been waging this war — seeking to limit economic pain on the people of Iran as opposed to the terrorists in Tehran, pushing for a peace deal as opposed to full-scale regime change — should be applauded. But I’m not surprised that Democrats and the fake news are trying to spin this into a loss.”
Last weekend, Trump gave Iran 48 hours to open the Strait of Hormuz or he’d, as White House press secretary Karoline Leavitt put it, “unleash hell” on Iran’s energy infrastructure. Some 36 hours later, however, the president threw out that ultimatum and set a five-day deadline for Iran to agree to the United States’ peace terms surrounding the war. And on Thursday, more than a day before that window expired, Trump again moved the deadline, announcing in a statement that negotiations would instead continue for an additional 10 days.
“As per Iranian Government request, please let this statement serve to represent that I am pausing the period of Energy Plant destruction by 10 Days to Monday, April 6, 2026, at 8 P.M., Eastern Time,” he wrote Thursday evening on Truth Social, just hours after telling reporters at his Cabinet meeting that Iran was ‘begging’ for a deal because ‘they have been just beat to s***.’ Talks are ongoing and, despite erroneous statements to the contrary by the Fake News Media, and others, they are going very well.”
Guy Snodgrass, who served as James Mattis’ communications chief during his stint as Trump’s secretary of defense, told the Washington Examiner that the opening of negotiations indicates that “Trump is on his heels as he can’t force Iran to surrender.”
“There is a higher than average likelihood that he thought this would be a quick decapitation strike like midnight hammer and Venezuela,” Snodgrass said. “However, Iran is proving tougher. U.S. had the element of surprise and the first 48-72 hours were the window for strategic success. Now, however, the strategic outcome resides with Iran.”
Snodgrass said the Trump administration has exhausted its military leverage short of deploying U.S. troops to Iran.
“If [Trump] walks away today, history views it as a failure — significant strategic goals weren’t achieved: no regime change, no nuclear materials seized and removed, Hormuz closed, etc.,” he said. “We’ve also expended a significant amount of treasure — money and weaponry — to only have achieved tactical outcomes. We’d be worse off than before the campaign.”
TRUMP IS BETTING ON HIMSELF, AND HIS CELLPHONE, TO CONTROL THE EPIC FURY NARRATIVE
Jennifer Kavanagh, the director of military analysis at Defense Priorities, agreed that Trump will need to reauthorize strikes to move Iran’s negotiating position, even before negotiations cease.
“Yes, I think it’s possible,” she told the Washington Examiner when asked if Trump could break his own timeline. “Trump does have a penchant for escalating on the weekend, when the markets are closed.”
White House press secretary Karoline Leavitt declined to say, when asked by the Washington Examiner, if Trump might strike Iran before the deadline expires but suggested the option is still on the table.
“You’re asking me to tell you if the commander-in-chief would authorize very strong strikes against the Iranian regime,” she said during Wednesday’s White House press briefing. “That’s not something I would ever reveal from this podium, true or not.”
Max Meizlish, a research fellow at the Foundation for Defense of Democracies’ Center on Economic and Financial Power and a former Treasury Department official, said that Trump’s current negotiating window had little to do with military policy and was wholly focused on calming the oil markets, a goal in which the president has achieved some success.
“Trump is actually having a pretty effective approach in this regard because oil prices are lower than what many analysts who are smarter than me would have been looking at,” he said.
However, Meizlish noted Iran’s public statements, denying that constructive negotiations were taking place even while clearly backchanneling with American intermediaries, mirrored Trump’s strategy.
“They don’t quite have the bully pulpit of Trump, but when you think about all they need to do is actually just come out and deny things that have any semblance of market stabilization — it creates uncertainty in the market,” he explained. “For the Iranians, that’s good because as much as they would like to win kinetically, it doesn’t seem like they’re really going to do that. So the option for them is to undermine any attempt by the United States to create stability in the market. And as long as they can do that, they can create more economic consequences for the United States and for global trading partners.”
The result is a standoff not just on the battlefield, but in global markets, with both sides using messaging as a weapon.
Whatever Trump’s reasons were for reopening negotiations, the president seems clearly unhappy with the progress of the talks.
“The Iranian negotiators are very different and ‘strange.’ They are ‘begging’ us to make a deal, which they should be doing since they have been militarily obliterated, with zero chance of a comeback, and yet they publicly state that they are only ‘looking at our proposal,’” he wrote on social media Thursday morning. “WRONG!!! They better get serious soon, before it is too late, because once that happens, there is NO TURNING BACK, and it won’t be pretty!”
Peter Loge, a professor at George Washington University’s School of Media and Public Affairs and the director of the Project on Ethics in Political Communication, suggested to the Washington Examiner that, based on Trump’s comments, the public should have little hope for a peaceful resolution in the near-term.
WHITE HOUSE PROJECTS OPTIMISM HOURS AFTER IRAN REJECTS US PEACE PLAN
“Unfortunately, President Trump hasn’t given people a lot of reasons to take his deadlines seriously,” he wrote in a statement. “President Trump has a history of trying to win in the moment, without a concern for the consequences of the win. He built and opened casinos in a rush of publicity, only to see the casinos fail and people lose their jobs. He was concerned with the ratings of his reality TV show, but he wasn’t invested in the effects of the show’s contestants. It’s easy to read his actions in Iran the same way, winning a market opening or getting attention online, without consideration for what comes next.”