Gloves Off with Scott Jennings, CNN’s Conservative Pundit episode artwork

EPISODE · Nov 21, 2025 · 1H 12M

Gloves Off with Scott Jennings, CNN’s Conservative Pundit

from On with Kara Swisher · host Vox Media

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 [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 [email protected] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Gloves Off with Scott Jennings, CNN’s Conservative Pundit

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This episode was published on November 21, 2025.

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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...

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