Gloves Off with Scott Jennings, CNN’s Conservative Pundit
On with Kara Swisher
New York Magazine
4.2 • 3.2K Ratings
🗓️ 21 November 2025
⏱️ 74 minutes
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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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