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On with Kara Swisher

Gloves Off with Scott Jennings, CNN’s Conservative Pundit

On with Kara Swisher

New York Magazine

Society & Culture

4.23.2K Ratings

🗓️ 21 November 2025

⏱️ 74 minutes

🧾️ Download transcript

Summary

Political commentator Scott Jennings has been called the “conservative explaining Red America to CNN viewers.” As the in-house Republican on CNN’s NewsNight With Abby Phillips debate panels, he often acts as a de facto Trump spokesman at the table. Jennings has been in Republican politics for more than two decades. In the mid-aughts he worked as a Special Assistant to President George W. Bush, and later advised Kentucky Senator Mitch McConnell in multiple campaigns. Jennings was openly critical of President Trump before and during his first term, especially after the January 6th attacks. But in his new book, A Revolution of Common Sense: How Donald Trump Stormed Washington and Fought for Western Civilization, Jennings argues that Donald Trump’s second term is not just a political comeback, but a transformation of the presidency itself. Kara and Scott spar about the Epstein files, discuss what they mean for the MAGA movement, and whether Trump’s policies are really “common sense.” Plus, how Scott turned into a MAGA man and why he likes being the odd-Republican-out at CNN. Note to listeners: This is an extended version of the episode that was originally published on Thursday, November 20th. Questions? Comments? Email us at on@voxmedia.com or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

Scott, you were smirk-free, so that's good.

0:14.6

Hi, everyone, from New York Magazine and the Vox Media Podcast Network.

0:18.1

This is On with Kara Swisher, and I'm Kara Swisher.

0:22.1

Today, I'm sitting down with someone you've probably seen me spar with on cable TV, CNN senior political commentator, Scott Jennings.

0:28.5

You heard that right. As the Wall Street Journal puts it, he's the conservative explaining

0:32.9

Red America to CNN viewers, and for some CNN viewers who are not in Red America, he is the villain.

0:39.8

Jennings has been in Republican politics for more than two decades. In the mid-aughts,

0:43.9

he worked as a special assistant to President George W. Bush and later advised Senator Mitch McConnell

0:48.8

in multiple campaigns. He was openly critical of President Trump before and during his first term, especially after the January 6th attacks, and as recently as 2023.

0:59.9

But at this point, it's fair to say that Jennings is a Trump man. And that's very clear if you read his new book, A Revolution of Common Sense, how Donald Trump stormed Washington and fought for Western civilization.

1:12.2

In it, Jennings argues that Donald Trump's second term is not just a political comeback, but a

1:16.6

transformation of the presidency itself. I wanted to talk to him about that and how his positions

1:22.5

have shifted dramatically over the years on all kinds of talking points. I also wanted to hear what he thinks

1:28.1

of the current MAGA infighting and what the post-Trump future of the Republican Party

1:32.2

will look like. Our expert question today comes from former Republican political strategist,

1:37.6

Tim Miller, host of the Bullwark podcast and a former colleague of Jennings. He has done the

1:43.2

opposite he'll turn to Jennings

1:45.1

and is a never-trumper.

1:47.5

This is going to be a spicy one,

1:49.0

but I also think it's really important

1:50.5

to talk to people you disagree with.

1:52.9

And Scott and I have had a really rocky relationship

...

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