President Donald Trump in Dearborn, Michigan, January 13, 2026. REUTERS/Evelyn Hockstein
President Donald Trump is "stuck" in a conflict that appears doomed to swallow up his presidency, and according to his one-time biographer, it is all because he has run up against an enemy who knows precisely "how to play him."
Michael Wolff is a longtime reporter and author, best known for his extensive coverage of Trump's personal and political histories, including a series of books about the chaos of his first term. In the latest episode of his Daily Beast podcast, "Inside Trump's Head," he touched on the disintegration of Trump's Iran ceasefire deal, making a bold proclamation about where the ordeal ranks across his entire political career.
“This is the worst mistake he has made," Wolff said, adding that the Iranians have been able to play Trump by way of "trolling," later adding. "These presidents get into these forever wars, and they can’t get out of them."
Wolff argued that Trump now finds himself trapped in the sort of foreign conflict that can "bring presidencies down," something that Iran is keenly aware of.
"These presidents get into these forever wars, and they can’t get out of them," he added.
Wolff further claimed that Trump had effectively told Iran, "I’ll give you any kind of agreement you want if you just stop this war," even going so far as to offer to pay them, something he had relentlessly attacked former President Barack Obama for supposedly doing with his Iran deal.
“They keep coming back,” Wolff said of Iran. “This is a whole process of trolling Donald Trump.”
Trump has now threatened to attack Iran with "1000 Missiles" if they attempt to assassinate him, even reportedly laying out instructions for Vice President JD Vance on how to approach the situation if he is killed. Wolff suggested, however, that "the death thing is probably more clearly related to his polling numbers than it is to whatever threats the Iranians are making."
Wolff also noted that the notion of threats against his life "does get under [Trump's] skin, and he is somewhat paranoid about this."
Veteran journalist Simon Marks made similar arguments last week, suggesting that Trump "fundamentally lacks the skills and temperament to successfully manage a diplomatic deal with" a country that operates like Iran, which does not operate anything like the world of New York real estate dealing that he is used to, and is not interested in giving him something he can tout as a victory.
