Iran is getting under Trump's skin by using his 'Art of the Deal' against him: analyst

Iran has discovered Trump's vulnerability — and it's exploiting it relentlessly. According to Slate columnist Ian Prasad Philbrick, Tehran's leadership is weaponizing the president's own playbook to keep him perpetually off-balance as he searches for an exit from the war.

The strategy is simple, ruthless, and devastatingly effective: study Trump's ghost-written "Art of the Deal," master his negotiating tactics, and turn them back on him with surgical precision.

On day 23 of the war, Iran's Revolutionary Guard spokesman Ebrahim Zolfaghari delivered a pointed message directly to the camera, the Iranian flag over his shoulder.

"Trump, you are fired," Zolfaghari said, recycling the president's signature catchphrase from The Apprentice. "Thank you for your attention to this matter," he added, mocking Trump's preferred closing phrase.

This wasn't random mockery. According to historian Ali Ansari of the University of St Andrews, the Persian translation of Trump's 1987 book The Art of the Deal has developed a devoted following inside the Islamic Republic. Iran's leadership has studied it carefully.

The psychological warfare extends far beyond insults. Iran has borrowed Trump's entire online playbook: Iranian embassy X accounts post cartoons mocking his negotiating position, compare him to a hapless cartoon bulldog, and reference the Epstein files. State media airs AI-generated propaganda videos depicting Iranian victory — mirroring the White House's TikTok-style hype reels cobbled together from movies and video games.

When Trump submitted a 15-point ceasefire proposal demanding uranium enrichment limits, missile restrictions, and Strait of Hormuz access, Iran responded with equally maximalist demands: war reparations, control of the strait, and an end to U.S.-Israeli strikes on Iranian leaders — positions Tehran likely knows Trump won't accept.

The gambit is exposing Trump's core weakness: his desperation to declare victory and escape situations spiraling beyond his control. Trump warned in his own book: "The worst thing you can possibly do in a deal is seem desperate to make it."

Iran understands this intimately. When Trump boasted the war was proceeding "ahead of schedule" and that Iran was "begging to make a deal," Tehran responded with calculated defiance, announcing it would "not allow Trump to determine the timing of the war's end."

A bewildered Trump posted on Truth Social: "The Iranian negotiators are very different and 'strange.'"

Battlefield realities remain grim for Iran. The war has depleted its missile reserves, destroyed much of its navy, and killed several top leaders. Its remaining leadership may be bluffing, projecting strength while privately seeking peace.

But for now, Iran's psychological strategy is working. The president who wrote the book on deal-making is being outmaneuvered by an adversary who simply read it, Philbrick wrote.