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Know Your Enemy

From Neocon to Never-Trump (w/ Bill Kristol)

Know Your Enemy

Matthew Sitman

Ronald Reagan, Conservative Movement, Politics, Right Wing, Society & Culture, National Review, Socialists, Reactionaries, News, History, William F Buckley, Conservatism, Leftists Look At Conservatism

4.72.2K Ratings

🗓️ 23 March 2026

⏱️ 71 minutes

🧾️ Download transcript

Summary

Matt and Sam talk to Bill Kristol about his journey from neoconservative thought leader to anti-Trump "liberal."

Transcript

Click on a timestamp to play from that location

0:00.0

All right, welcome listeners to episode 132 of Know Your Enemy. I'm Matt Sitman, your podcast co-host, and I'm here as always with my great friend, Sam Adler Bell. Hello, Sam.

0:10.7

Hi, Matt. I am so excited to put this episode out into the world.

0:15.0

It's a corker. Yes, I will say that this guest probably is our most requested guest, at least at this point.

0:22.9

By a certain segment of the audience anyway.

0:25.4

Yes. And I think for good reason. We've wanted to talk to Bill Crystal for a while now.

0:32.8

You know, this is a podcast that deals, among other things, with conversions and trajectories and changing minds,

0:39.4

people on the left who moved right, people on the right who moved left. So Bill was, you know,

0:44.4

the themes of this podcast, kind of in human form, people who've moved left to right, right to left,

0:50.4

Bill's all the above. In some ways, Bill does not need an introduction.

0:55.9

But for listeners who don't know him, well, there's so much we could say.

1:00.1

Currently, he is one of the most prominent never Trump figures in our politics.

1:05.0

He's stayed that way, become even more anti-Trump.

1:08.6

But prior to that, I mean, he's had a long career. He was Dan Quayle's

1:12.8

chief of staff when Quayle was vice president. Bill Crystal was a speechwriter. He founded the

1:18.1

weekly standard in 1995, you know, was a major proponent of the Iraq War after 9-11,

1:24.0

which we do discuss. And, you know, has just been at the center of our politics

1:29.2

for decades now. I mean, in his pedigree. Yes, yes. He's the son of godfather of neoconservatism,

1:36.6

Irving Crystal, and Gertrude Himmelfar, herself a very accomplished historian and writer as well.

1:42.4

So he is kind of neocon royalty. We do talk about that.

1:46.6

Bill was a student of Harvey Mansfields when he did his Ph.D. at Harvard, where his first year there,

1:51.9

he was the roommate of Alan Keyes, former Maryland and then Illinois Senate candidate. He ran against Obama.

1:58.4

And I should say, of all these biographical details about Bill

...

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