TRUMP’S DARK OBSESSION

This Is Trump’s Twisted New Fixation: Wolff

Michael Wolff unpacks how Donald Trump’s latest threat to “annihilate” Iran came about.

Donald Trump tasked White House staffers with finding a new word to describe the brutal military offensive against Iran he floated during his United Nations speech this week, author Michael Wolff says.

Trump told the global audience Tuesday that he had a “big decision” to make.

“Will a deal be made with Iran that lets them rebuild and create a far greater country than it ever was before? Maybe the greatest in the Middle East or even the world?” he said. “Or do I annihilate the Islamic Republic, and do it quickly, never giving them a chance to kill and destroy people and countries again? Do I drive them into hell with no chance of survival and no hope of future greatness or generations?”

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On the Daily Beast’s Inside Trump’s Head podcast, Wolff said the 80-year-old president asked that an alternative to “obliterate” be given to him, rather than use his own brainpower.

“I was interested in that word—‘annihilated,’” Wolff told co-host Joanna Coles. “And so I spoke to somebody in the White House who said, ‘Well, you know, his favorite word is ‘obliterated,’ but he needed a new—he specifically asked for a new word.’ So, they went around and they offered him up ‘annihilated,’ which he liked because it was somewhat like ‘obliterated,’ but also that it wasn’t. So he got a new word. It was like presenting Trump with a new word.”

Coles added, “This is like one of those school things where you go in and there’s a new word written on the board and you all learn it and use it throughout the week.”

“Totally,” Wolff agreed, predicting that Trump won’t end up “annihilating” Iran “in the same way he didn’t obliterate Iran.”

After Trump launched strikes on Iran in June 2025, he claimed the country’s nuclear sites had been “obliterated,” even though intelligence reports on the damage didn’t go that far.

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“It’s just Trumpian inflation, Trumpian drama, the Trumpian word. He finds a word that he likes, and we will now hear ‘annihilated’ on a rather regular basis, of course,” Wolff continued.

When reached for comment, the White House criticized Wolff’s credibility.

“Michael Wolff is a professional scumbag and serial liar whose brain has been completely warped by his severe and incurable disease known as Trump Derangement Syndrome,” spokesperson Davis Ingle said.

The Iran war has gone on for nearly seven months, despite Trump claiming weeks into the conflict that the U.S. had “won.” The conflict, and the subsequent rise in gasoline and diesel prices, has jeopardized the GOP’s odds of retaining both chambers of Congress in the midterms. Accordingly, some Republican candidates in close races have since called for an end to the war.

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