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WATCH: What Trump fears most

I go deep into the inner life of Trump and MAGA with Gabriel Sherman, veteran chronicler of Trump and the right, and writer of the biopic "The Apprentice"

We just finished talking with Gabriel Sherman, the screenwriter behind The Apprentice, the new film exploring Donald Trump’s formative years and his relationship with the brutal, amoral lawyer and kingmaker Roy Cohn, whose three rules shape Trump’s every move to this day:

  1. Attack. Attack. Attack.

  2. Admit nothing. Deny everything.

  3. Claim victory and never admit defeat.

When Cohn was dying of AIDS, his protege Donald Trump — on the rise after learning all he could from Cohn’s lessons in power — abandoned him. Cohn told journalist Wayne Barrett that he couldn’t believed Trump had done it, that Donald “pisses ice water.”

And coming from one of the most vicious figures of the 20th century, that says a lot about Trump — or at least the Trump that Cohn had helped make.

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We talked to Sherman — a veteran reporter who’s covered Trump for decades, since he started at The New York Observer as a real estate reporter — about what the old Trump can tell us about the new one; why fictionalization allowed him to access deeper truths about the man; the fragile Musk relationship; and Trump’s biggest fear.

If you want to understand and thwart the Donald Trump of today — the one the younger man invented out of what he learned from his tyrannical father, who divided the world into killers and losers, and Cohn, who taught him the rules for dominating both — you won’t want to miss this conversation.


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We’ve another great live conversation coming up tomorrow. Friday, February 28, at 12:30 p.m. Eastern, we’ll be talking to Stephen Wertheim, the historian and theorist of America’s place in the world. To join us, download the Substack app and turn on notifications. You’ll get an alert when we’re live and you can watch from your iOS or Android device.

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