At a recent press conference, General Dan Caine, Chairman of the Joint Chiefs of Staff, had to step in to stop Donald Trump from revealing classified military information. The moment happened while Trump was talking about the successful rescue of two U.S. airmen in Iran. Trump was asked whether all his military advisers supported the high-risk mission. He admitted they did not all agree. “No, there were military people, very professional, that preferred not doing it,” he said, referring to the rescue attempt carried out after two U.S. jets were shot down over Iran. He then began describing the scale of the military presence, saying, “Somebody said it’s the only time it’s ever been done. I said, that’s not possible. But it is possible. Because you’re going into hundreds of thousands of soldiers along the path. I mean, look at some of the helicopters, how they got hit.” He then turned to General Caine and asked, “How many men did you send altogether? Approximately for the operation?” Caine replied, “I’d love to keep that a secret.” Trump’s Iran deadline puts him in a difficult position as pressure mounts on both sides Trump accepted this and said, “But I will tell you, the number, I’ll keep it a secret. But it was hundreds, and hundreds of these people, that’s pretty good.” All of this took place during an ongoing five-week joint US-Israeli war against Iran. Trump has set a new deadline for Tuesday at 8:00 PM Washington DC time, which is 00:00 GMT on Wednesday, for a new round of strikes. He warned these strikes would be devastating, claiming that within four hours, “every bridge and power plant in the nation will be decimated,” and stated on Monday that “very little is off-limits.” TRUMP: How many men did you send altogether, approximately?CAINE: Uhhhh. I'd love to keep that a secretTRUMP: It was hundreds pic.twitter.com/u9553rEuT6— Aaron Rupar (@atrupar) April 6, 2026 To avoid further strikes, Trump has demanded that Iran agree to a deal “that’s acceptable to me,” which includes ensuring “free traffic of oil” through the Strait of Hormuz. Iran, however, has shown little sign of accepting these terms. They rejected a temporary ceasefire and put forward their own demands, which a U.S. official described as “maximalist.” It is worth noting that Trump has also faced criticism from allies over the Iran conflict, further complicating his position on the world stage. This puts Trump in a difficult spot. If no deal is reached by the deadline, he could extend it, something he has already done three times over the past three weeks. Donald Trump has escalated demands for a deal with Iran, insisting the Strait of Hormuz be reopened ahead of today’s 8 pm EST deadline.Trump has threatened to destroy Iranian infrastructure if his terms aren’t met. https://t.co/NmWMgEMwMW— Bloomberg (@business) April 7, 2026 But repeatedly backing away from strong, public threats risks hurting his credibility. Iran, and the wider world, may begin to conclude that, despite America’s clear military superiority, the U.S. is not negotiating from a position of full strength. Trump, however, pushed back on Monday, saying, “We won. They are militarily defeated. The only thing they have is the psychology of: ‘Oh, we’re going to drop a couple of mines in the water’.” He was referring to Iran’s ability to deter oil tankers from using the Strait of Hormuz through drones, missiles, and mines; a threat he seems to believe is being underestimated by the U.S. side. “We can bomb the hell out of them,” he said. “We can knock them for a loop. But to close the Strait, all you need is one terrorist.” Trump has also said, on multiple occasions on Monday, that he does not want to carry out more devastating strikes. He acknowledged that anything destroyed would eventually need to be rebuilt, and that the U.S. might help with that. “Do I want to destroy their infrastructure? No,” he said. “Right now, if we leave today, it will take them 20 years to rebuild their country.” According to the BBC, he added that following through with his bombing threats could push that timeline to a century. Despite all of this, Trump says he still hopes for a breakthrough. “We have an active, willing participant on the other side,” he claimed. “They would like to be able to make a deal. I can’t say any more than that.” He insists that “every single thing has been thought out by all of us,” but refuses to share details. Whether that reflects real behind-the-scenes progress or strategic bluffing remains unclear. “They have till tomorrow,” Trump said. “We’ll see what happens. I believe they’re negotiating in good faith. I guess we’ll find out.”