Michael Wolff On Trump's Psyche

Oct 10, 2025

Michael Wolff, a prominent journalist and author known for his in-depth reflections on Donald Trump, opens up about Trump's psyche and behavior. He discusses how Trump's defeat in 2020 fueled a narrative of false victory and how his relentless need for performance may stem from his reality TV background. Wolff also shares insights on Trump’s motivations for running again, shaped by legal challenges and his combative instinct. Furthermore, he offers a look into Trump's complex relationship with Melania and their shared social circles, touching on figures like Epstein.

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INSIGHT

Belief Became Reality After 2020

Michael Wolff argues Trump genuinely came to believe he won 2020 and constructed a conspiratorial reality around it.
He replaced advisors with yes-men to reinforce that reality and dug in obsessionally.

ANECDOTE

Dinner At Mar-a-Lago Proves Conviction

Michael Wolff recounts a Mar-a-Lago dinner where Trump spun disconnected numbers to prove he won the election.
Wolff believed Trump sincerely convinced himself by linking those figures into a false certainty.

INSIGHT

Trump's Monologue Blocks Reality

Wolff says no one can tell Trump anything because he never allows a conversation to occur and dominates every encounter.
That constant monologue made it impossible for aides to explain the election loss or reality to him.

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This is a free preview of a paid episode. To hear more, visit andrewsullivan.substack.com

Michael is a media critic and author. He’s been a columnist for New York magazine, Vanity Fair, British GQ, the Hollywood Reporter, and the Guardian. Among his many books include four on Donald Trump — the third one we covered on the Dishcast, and the latest was All or Nothing: How Trump Recaptured America. He also co-hosts the podcast “Inside Trump’s Head.”

For two clips of our convo — on Trump’s closest lackeys, and examples of the best resistance to Trump — head to our YouTube page.

Other topics: lawfare as central to spurring Trump to run again; his epic comeback after losing in 2020; retribution; Michael’s dinner with Donald and Melania; the near assassination and “Fight!”; 14 years as a reality TV star; his brilliant campaign stop at McDonald’s; how he met Epstein; their obsession with young models; Karoline Leavitt morphing into a model; the cold arrangement of his marriage to Melania; Ghislaine Maxwell; Bill Clinton; how Trump treats female aides; Lindsey Halligan and the Comey indictment; Susie Wiles; Trump’s surprising pick of Vance; his reluctant choice of Pence; Jared Kushner; Stephen Miller and targeting judges; Don Jr and crypto corruption; Musk’s fundraising; January 6; McConnell’s chance to remove Trump; Trump’s strange deference to Netanyahu; the MAGA fissures over Israel and Epstein; the Mossad conspiracy over Kirk; Tucker 2028; Hegseth’s speech to the generals; sending troops into US cities; Trump’s visit with King Charles; Jerome Powell’s backbone; the law firms, universities, and news outlets that caved; Mamdani; the legendary luck of Trump; and what he might do if Dems take back the House.

Browse the Dishcast archive for an episode you might enjoy. Coming up: Charles Murray on finding religion, Karen Hao on AI, Michel Paradis on Eisenhower, David Ignatius on the Trump effect globally, Mark Halperin on the domestic front, and Arthur Brooks on the science of happiness. As always, please send any guest recs, dissents, and other comments to dish@andrewsullivan.com.