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Inside Trump's Head

How Trump's Threats Have Left Him Exposed: Wolff

Inside Trump's Head

The Daily Beast

News, Society & Culture

4.3696 Ratings

🗓️ 20 February 2026

⏱️ 40 minutes

🧾️ Download transcript

Summary

Michael Wolff and Joanna Coles untangle a week where chaos seems to be the point, including the stunning arrest of Andrew Mountbatten-Windsor in the widening Jeffrey Epstein fallout. Meanwhile in Washington, Trump gathers his Board of Peace to bankroll his grand vision for Gaza while facing a far more combustible reality: a potential military showdown with Iran that he may neither want nor be able to control. As European partners keep their distance and troop buildups raise the stakes, Wolff and Coles probe whether Trump is orchestrating strategic distraction—or simply caught between looking weak and starting a war. With scandals colliding and global order wobbling, is this all part of a master play, or are we watching events slip beyond Trump’s grasp? Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

He's got himself in somewhat of a serious pickle here.

0:05.0

If he doesn't go at this point, I mean, he kind of really looks weak.

0:09.0

It's very complicated.

0:11.0

I mean, Iran is a big country, is a formidable military power.

0:17.0

People in the White House always talk about his reluctance to go to war. He's not going to go to war because it's too complicated for him.

0:27.6

You know, he doesn't like to listen to generals. He doesn't like to be confronted with information. War is an information-heavy activity, to say the very least.

0:46.5

Michael.

0:49.0

There is a sense of, there's too much going on.

0:53.5

I can't keep on top of it. I wake to a, I have a very

0:57.2

bad night because I'm still sleeping off this, this surgery and it means you can only sleep on

1:02.7

your back. I'm a side sleeper. This is too much information, but I had a very spotty night.

1:08.0

And I wake up. Medicated? Still on the, uh, I'm, I'm weaning myself off. I'm

1:13.6

weaning myself off, but. I don't think you can tell the difference, can you?

1:21.1

Well, I don't want you could go down a path in which there's no return. We're not going to do that.

1:26.8

But I've been weaning myself off.

1:28.6

But my point is a terrible night's sleep,

1:30.5

and I wake up to what feels like a hallucination,

1:33.9

which is a text chain full of, oh, my God, oh my God, oh my God,

1:40.1

Andrew, the first member of the British royal family

1:44.0

to be arrested for 400 years,

1:47.5

unless you count Princess Anne, who got briefly arrested when her dog, Dottie, bit two children.

1:56.1

And she was eventually let go with a fine.

...

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