Podcast Summary

On with Kara Swisher – "Gloves Off with Scott Jennings, CNN’s Conservative Pundit"

Air Date: November 20, 2025
Host: Kara Swisher
Guest: Scott Jennings, Senior Political Commentator at CNN, longtime Republican strategist, author of "A Revolution of Common Sense"
Expert Question: Tim Miller, The Bulwark Podcast

Episode Overview

This episode features a candid conversation between Kara Swisher and Scott Jennings, a prominent conservative commentator and political strategist. Swisher, known for her incisive interviewing style, digs into Jennings’s enthusiastic support for Donald Trump’s second term, his evolution on Trump and GOP politics, the state of the MAGA movement, infighting within the Republican Party, and the future of American conservatism. Through sharp debate and occasionally “rocky” exchanges, they cover everything from cable news theatrics to deep policy divides, punctuated by a probing question from Jennings’s former anti-Trump colleague, Tim Miller.

Key Discussion Points and Insights

1. Scott Jennings as "Conservative Villain" on CNN

• Debate as Wrestling

  • Jennings views his role on CNN’s "NewsNight" as a “debating show built around conflict” akin to wrestling:
    "It is truly a show built around conflict, the conflict between conservatives and liberals … I think there’s a hunger for it." (05:28)
  • Swisher challenges him on the authenticity of this persona, citing friends who say he’s less confrontational off camera.
  • Jennings sees himself as “a press secretary for half the country,” channeling perspectives of Red America:
    "I am somewhat of a press secretary for half the country … trying to give you an authentic representation of how all this is being absorbed by non-liberal America." (06:59)
  • He insists he does not say anything on TV he doesn’t believe or can’t defend.

• Role of Debate Shows in Polarization

  • Swisher: “Is that good for America, given how polarized we are as a society?” (10:25)
  • Jennings: “I think it’s good for America for them to be more engaged with politics than less … If you can present your arguments in a way that attracts more audience, that’s ultimately a good thing for civil discourse.” (10:31)

2. Jennings’s Journey: Never-Trumper to Trump Enthusiast

• Political Evolution
  • Swisher notes Jennings’s outspoken criticism of Trump—before and after Jan. 6—but observes his new book is “very clear” that he now backs Trump wholeheartedly.
  • Jennings describes the motivation for the book:
    "I thought 100 people would write books about this period attacking him … one person who generally agrees with what he’s doing should write a book about it from our perspective." (03:58)
• Navigating Public Critique
  • Swisher brings up the accusation that Jennings’s pro-Trump “conversion” is just performative, to which he replies he’s “trying to give people an authentic view … of how most Republicans and most conservatives are absorbing the breaking news.” (06:59)

3. MAGA Infighting and the Future of Trumpism

• Epstein Files and MAGA Division
  • Discussion of the House voting to force release of Epstein files, Trump’s pivot to support the bill, and Marjorie Taylor Greene’s public break with Trump: "[Greene’s] been a thorn in our side on Epstein, and now she's running to The View to complain about the president. This doesn't sound like someone who is our friend." (19:44–20:05)
  • Both Swisher and Jennings note Trump’s base obsession with the Epstein issue and how it has become divisive within MAGA ranks.
• Will the MAGA Movement Survive Trump?
  • Jennings doubts anyone—especially VP J.D. Vance—can replicate Trump’s coalition:
    "I don't think anyone can replicate Trump. ... His force of personality has held together people from disparate wings of the Republican Party … the challenge for JD or whoever comes next is how do I carry forward knowing I can't replicate it, but I still have to keep enough people in the tent to win." (20:36)
  • Swisher asks if Vance is the heir apparent; Jennings thinks so—unless circumstances dramatically change. (21:22)

4. Conflicts of Interest and Media Attacks

• Trump Welcomes MBS, Spurns Press
  • Trump’s warm White House reception of Saudi Crown Prince MBS (first visit since Khashoggi murder) and his attack on ABC’s Mary Bruce for questioning him on the relationship:
    "Trump … trying to get them [Saudis] to join the Abraham Accords... [regarding the media] he believes they're hostile to him. I think they are largely hostile to him. And he reacts to them in a way that you would if someone was constantly hostile to you." (26:22–27:25)

5. Media Collusion, Tech Companies & Hunter Biden

• Hunter Laptop Story: “Collusion” or Politics as Usual?
  • Jennings calls the media and tech handling of the Hunter Biden laptop story “one of the biggest lies that was told to try to get Joe Biden over the finish line.” (34:01)
  • Swisher disputes that it was a coordinated “collusion”:
    "There is no proof that tech companies colluded to do this. This is nonsense and he knows it." (32:00)
  • Jennings:
    "You had tech companies and platforms literally not putting the story on their platform and they were actively censoring it on the doorstep of an election.” (32:25)

6. “Common Sense” and Trump’s Second Term (The Book)

• The "Revolution of Common Sense"
  • Title origin: Trump’s inaugural address phrase; idea that he taps into “simple” solutions neglected by elites. (35:46)
  • Swisher critiques the framing—citing contradictory, performative policy examples.
• Elon Musk & Government Data Access
  • Jennings is “not concerned” about Elon’s data access, seeing him as a fiscal reformer, not as a privacy threat:
    "He said, I'm trying to find a way to make America not go bankrupt … I've been given a mandate by the president to find wasteful spending and to cut it." (39:43)

7. Congress, Fiscal Policy, and Executive Overreach

• Jennings calls for Congress to take fiscal responsibility seriously but admits the current Congress is mostly “in step” with Trump due to platform alignment (43:23), while Swisher presses for concern about executive overreach and lack of pushback—even from supposed mavericks like Marjorie Greene.

8. Tim Miller’s Expert Question: Could 2015 Jennings Have Imagined 2025 Jennings?

[47:18–52:27]

• Miller presents a hypothetical:
  —If, in 2015, he’d told Jennings Trump would win twice, lose, instigate Jan. 6, return, and remake the GOP—with Jennings as a supporter—would he have believed it?
• Jennings’s response:
  "2015 Scott would have been totally shocked … But I learned very quickly during that primary not only should it be taken seriously, but it was quite likely to happen … I guess I sobered up a little bit about what's really at stake in this world. And it's not just daily policy fights, but it's about ideologies, and it's about whether we're going to have an American future or something much darker." (48:59–51:22)

9. Lightning Round: Limits of Loyalty to Trump

(54:16–56:12)

• Swisher asks if Jennings would back:
  • A Trump war to take Greenland/Canada/Venezuela?
    Jennings: “No problem with military action against Venezuela. Don’t think we’ll be having any wars with Canada or Greenland.”
  • Trump using the FCC to shutter media?
    Jennings: “The [FCC] should just enforce the law as directed by Congress.”
  • Trump running for a third term?
    Jennings: “No.”
  • Trump blocking polling sites?
    Jennings avoids direct answer, says all legal voters have a right to vote.
  • Trump refusing to leave office?
    Jennings: “We ought to have a peaceful transfer of power just the way we had in 2024.”

10. Career and Personal Reflections

• On Possible Move to CBS/Other Networks
  • Swisher probes reports of CBS interest; Jennings declines to comment but says:
    "I was put on this earth to debate and to do so in a hostile environment." (56:49)
• On Running for Office
  • Jennings leaves door open for future runs, credits Mitch McConnell (more like a grandfather) as mentor (57:23).
  • Swisher asks if McConnell’s break with Trump has influenced him; Jennings says not really, highlighting their shared legacy on the Supreme Court. (58:09)
• On Party Loyalty
  • Swisher: “Would you be a windsock if another candidate takes the party in a new direction?”
  • Jennings: “If someone becomes the nominee of the Republican Party and does what I want 90 or 95% of the time and the Democrat does 0%, it’s a pretty easy choice.” (59:50–60:15)

Notable Quotes & Memorable Moments

• Jennings on His Role at CNN:
  "I am somewhat of a press secretary for half the country … trying to give you an authentic representation of how all this is being absorbed by non-liberal America." (06:59)

• Swisher to Jennings on Performative Smirking:
  “You’ve perfected the smirk, for sure … It’s an expression. Does a drunk agree with the sober kind of thing?” (07:46)

• On Conflict as Civil Discourse:
  "If you can present your arguments in a way that attract[s] more audience, I think that's ultimately a good thing for civil discourse." (10:31)

• Jennings on Trump as a Unique Force:
  "I don't think anyone can replicate Trump. ... His force of personality has held together people from disparate wings of the Republican Party." (20:36)

• Swisher’s pointed challenge:
  "Let’s do a lightning round … Would you support President Trump if he finds a loophole in the 22nd Amendment and runs for a third term?" (54:40)

• Jennings on the possibility:
  "No." (55:38)

• Swisher, on party-line voting:
  "Would you be a windsock … or go along with whatever candidate the GOP offers?" (59:39)

• Jennings, revealing the party calculation:
  "If somebody becomes the nominee of the Republican Party and they do what I want them to do 90 or 95% of the time, and the Democrat nominee … does what I want them to do 0% of the time, it’s a pretty easy choice for me." (60:15)

Important Timestamps

• Debate/show format & authenticity questions: 05:28–10:31
• MAGA infighting, Epstein files, Marjorie Taylor Greene: 14:10–21:52
• Trump/MBS, press conflicts: 26:22–28:52
• Hunter Biden laptop, media collusion: 32:00–35:46
• Common sense & policy: SNAP, Doge/Elon Musk: 35:46–44:16
• Expert question (Tim Miller) and response: 47:18–52:27
• Lightning round (limits of Trump loyalty): 54:16–56:12
• Jennings's career future, Kentucky politics, loyalty to McConnell: 56:12–59:39
• “Windsock” party loyalty question: 59:39–60:15

Tone & Takeaways

Kara Swisher’s signature directness draws out Jennings’s rationalizations, self-awareness, and the tensions between personal belief, party loyalty, and the “performance” of conservative punditry. Jennings is unflappable, expressing both pride in the ideological transformation happening in the GOP under Trump and a pragmatic willingness to back the party, even as foundational conservative tenets shift. The episode leaves listeners with a nuanced, at times combative but civil, examination of modern Republicanism’s identity crisis—and the blurring line between persuasion, performance, and conviction in American politics.