Michael Wolff has written four books about Donald Trump. He spent nine months inside the White House during the first term and has been making increasingly dark predictions about the second term since January 2025.
His latest warning arrived on Tuesday, when he argued that the real problem facing Trump is not the Iran war, the polls or congressional resistance but something much more familiar.
“What Trump has tried to do is impose himself on virtually every aspect of American life or even… world life,” Wolff told his co-host Joanna Coles on the Inside Trump’s Head podcast. “And the problem with that is that if this starts to go wrong, everything then begins to remind everyone that Trump is responsible for this. Everything becomes a negative for Donald Trump.”
The week provided plenty of material for that argument.
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Trump attended Game 3 of the NBA Finals at Madison Square Garden on Monday and was booed during the National Anthem, with Coles, who was present at the game, describing the reaction as a “resounding boo.” He walked out of the Kristen Welker interview on Sunday mid-sentence. He is also building a 5,000-seat UFC arena on the White House South Lawn for his birthday party next week.
A new YouGov survey found 40% of Americans strongly disapprove of the UFC event. Only 12% strongly approve.
To Wolff, these are not separate stories.
“He’s created a set of symbols here that… are going to hurt him rather than help him,” Wolff said. “He shows up at the game in New York and gets booed. He destroys… the White House environment for his own satisfaction and grift.”
Coles saw the pattern too.
“It does feel a little bit like this is all closing in on him, at least in that moment when he stormed out of the interview with Kristen Welker on NBC’s Meet the Press.”
Wolff argued the Welker walkout was not a strategic display of strength.
“This is literally the way he is with everyone. The people around him — his aides, friends, family, you know, Vance, Rubio, Susie Wiles — everybody faces this: that he won’t stop talking, that you can’t disagree with him, that there really is no debate.”
In Wolff’s view, the UFC event belongs in the same category.
“Why is he putting the UFC on the White House lawn when that is obviously a mistake of just a political perception that you would not want. But he can’t see that,” Wolff said.
The argument is not a new one for Wolff. He made a similar case during a June 5 episode of the same podcast, when he said that “this Trump enterprise is coming apart” and predicted the deterioration would be visible “on an almost day-by-day basis.”
Featured image via YouTube screengrab
