On with Kara Swisher Gloves Off with Scott Jennings, CNN’s Conservative Pundit
154 snips
Nov 21, 2025 
Scott Jennings, a longtime Republican political operative and CNN commentator, shares insights from his new book about Trump’s presidency. He discusses his role on CNN's debate panels, likening the format to wrestling, and explains his complex relationship with Trump. Jennings explores the MAGA base's frustrations, the impact of the Epstein files, and the challenges of maintaining Trump's coalition. They also debate what 'common sense' means in Trump’s agenda and reflect on how Trump has transformed the GOP.
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Why He Wrote A Pro‑Trump Book
- Scott Jennings wrote his pro-Trump book to present a sympathetic, insider perspective for center-right readers.
- He claims much of his material came from interviews with Trump, cabinet members, staff, and observation of Trump in early 2025.
Debate Role Compared To Wrestling
- Jennings likens his CNN debate role to wrestling because the show is built around conflict and timed fights.
- He says the format attracts viewers who want both information and entertainment and has broadened conservative reach into CNN's audience.
Sees Himself As A Public Representative
- Jennings frames himself as a de facto press secretary for much of America, representing how non-liberal voters absorb events.
- He insists he won't say things on air he doesn't believe or can't defend and sees value in drawing audiences into politics.
