The Sage Steele Show | EP 73: CNN's Voice of Reason: Scott Jennings

Date: September 17, 2025
Host: Sage Steele
Guest: Scott Jennings (CNN commentator, GOP strategist, author, radio host)

Episode Overview

In this candid and dynamic conversation, Sage Steele sits down with CNN contributor Scott Jennings to discuss his meteoric rise as a conservative voice on mainstream media, the intense world of televised political debate, and the post-2024 political landscape in America. Jennings opens up about his experiences on CNN, the lessons from the Trump and Biden presidencies, his mentors, and how personal history and family inform his approach to politics and media. The episode covers everything from the importance of authenticity in public discourse to navigating intense political opposition and media caricatures. The conversation also touches on deeply personal reflections regarding service, legacy, and the future of American politics.

Key Discussion Points & Insights

1. Jennings’ Approach to Political Commentary and Debates (00:38–05:11, 13:55–18:27)

• Jennings criticizes the double standards in media coverage of presidential health and competence, especially contrasting Trump and Biden (00:38).
  • Quote: “One day, Donald Trump couldn’t hold a glass of water and we had every medical person coming out of the woodwork... Joe Biden could barely walk an eye with ours.” – Scott Jennings (00:38)
• He highlights the importance of authentic debate, both on television and in American culture.
  • Quote: “The country is founded on debates. This is the essence of our political culture, so it’s a privilege to participate.” – Scott Jennings (15:45)
• Jennings attributes the success of CNN’s new debate format to its unscripted nature and willingness to showcase genuine ideological clashes.
  • Quote: “We’re not overly scripting these conversations and people like it... Audiences want authenticity. This is why Trump succeeds.” (17:00)
• Discusses preparation and unpredictability of debates, emphasizing research and real-time reaction over canned points (18:27).

2. Reflections on Trump’s Second Term and Its Impact (03:39–07:08, 09:08–12:54)

• Both host and guest reflect on surprises and lessons learned from Trump’s return to office, noting his administration’s speed, preparedness, and focus after the near-fatal assassination attempt.
  • Quote: “It did change his perspective on life, on why he’s here, on what his purpose is here... it was a near-death experience. I’m sure it had a psychological impact on him.” – Scott Jennings (09:08)
• Jennings credits a purposely chosen staff for the administration’s efficiency and willingness to confront entrenched Washington resistance.

3. Media, Authenticity, and Personal Branding (13:55–19:03)

• Jennings discusses the impact of his increasing visibility on CNN, especially as a conservative voice during and after the 2024 election cycle.
• He credits CNN leadership for giving him the space to be unscripted and authentic, mentioning positive relationships with liberal colleagues like David Axelrod and Van Jones.
  • Quote: “CNN…let me do my thing, and they don’t tell me what to say and I don’t really have a script… I get to go out there and be my authentic self.” – Scott Jennings (15:45)
• Emphasizes the shift away from legacy media’s scripted panelists: “The era of scripted puppets is over.” (17:00)

4. Debate Tactic: Composure and Economy of Words (21:38–25:09)

• Jennings explains his calm debate demeanor and the value of keeping arguments concise.
  • Quote: “I believe in the economy of words. I believe in the efficiency of arguments. I often say the least, but I try to say the most, even when I’m saying the least.” (23:20, 24:54)
• Shares advice he received early on: “Pretend you’re at a dinner party and there are no cameras. How would you act in those settings?” (24:06)

5. Relationships and Mutual Respect Amidst Political Differences (25:09–27:50)

• Discusses strong professional and even personal friendships with ideological opposites, including Van Jones and David Axelrod, underscoring respect for those who challenge their own side honestly.
  • Quote: “You can respect people and trust them, even if you don’t necessarily agree with them. And they have certainly earned that out of me.” (26:18)

6. Career Retrospective: GOP Campaigns, Media, and Mentors (42:00–47:56)

• Jennings outlines his path from small-town Kentucky to national GOP campaigns for Bush, Romney, McConnell, and Trump.
• Describes the through line in his work: defending Western civilization, common sense, and free speech (43:53).

7. Discussion on Identity Politics, Merit, and Conservative Role Models (35:02–41:14)

• Sage and Jennings critique tokenism and identity politics, arguing true empowerment comes from merit and character.
  • Quote: “We want people to rise and fall based on talent, hard work, merit. And they truly want people to rise and fall based on identity politics.” – Scott Jennings (37:01)
• They lament the lack of recognition for Black conservatives like Clarence Thomas and Condoleezza Rice, discussing the backlash against “nonconforming” voices.

8. Lessons in Loss and Resilience (33:59–35:02, 28:03–31:42)

• Jennings recounts the heartbreak of the Romney 2012 campaign and being caricatured by media.
• Shares a poignant memory from 2024 election night, describing it as “the revenge of the average everyday American” (28:03).
  • Quote: “This election had been the revenge of the average everyday American…a repudiation of the political information distribution complex.” (28:03)
• Reflects on balancing passion with composure in debate and refusing to take adversaries’ attacks personally.

9. Term Limits, Aging Politicians, and Personal Responsibility (47:56–52:40)

• Engages with the nuanced question of term limits, noting that voters ultimately have the power to enact change.
  • Quote: “We have term limits. They're called elections.” – Scott Jennings (49:36)
• Shares insight on his mentor, Mitch McConnell, his health, and the legacy he’s built for Kentucky.

10. Family, Personal Background, and Public Service (54:05–59:00)

• Scott opens up about his working-class roots, close relationship with his father (a Democrat turned Republican), and how those experiences ground his approach to public service.
• Describes his pride in being a first-generation college graduate and the importance of intergenerational relationships.
  • Quote: “[My dad] was the first person though to tell me Donald Trump was gonna be the next president … he said ‘I’m just telling you, all my friends are talking about it.’” (55:19)

11. Legacy, Fatherhood, and Motivation (59:04–62:54)

• Reflects on the challenges of raising four boys, the sacrifices of public life, and legacy.
  • Quote: “When you have kids… you realize, that is the best advice. If you want to do something nice for someone, do something nice for their kids.” (59:09)
• Expresses his primary motivation: building a better country for the next generation.

12. On New Media, Truth, and Courage (62:21–63:51)

• Both Sage and Scott highlight the importance of courage and truth in a media landscape marked by upheaval and distrust.
  • Quote: “What do you want to have people say about you? She had the courage to tell the truth… Truth has never gone out of vogue. We have to have people courageous enough to tell it.” – Scott Jennings (62:54)

13. Supporting Israel and Recognizing Barbarism (63:56–66:09)

• Jennings explains why he wears a yellow ribbon daily: to keep awareness on Israeli hostages still held after October 7, 2024.
  • Quote: “What happened on October 7 is one of the biggest acts of barbarism and savagery we’ve seen in modern history…The defense of Western civilization depends on that.” (63:58, 66:04)

Notable Quotes & Memorable Moments

• Election Night Vindication:

  • “On election night, when they finally let me out of my cage at 3:38am to admit to the world that Donald Trump had won the election, I gave a speech...what had just happened and how this election had been the revenge of the average everyday American.” – Scott Jennings (28:03)

• On Personal Demeanor and Body Language:

  • “If you were in a real life setting with someone, you would be doing that with them...a little body language or a little bit of [a look]—it makes people feel like, hey, I’m in the room with these folks who are having a real conversation.” – Scott Jennings (24:54)

• Why Authenticity Resonates with Audiences:

  • “The era of scripted puppets is over... This is why Trump succeeds. He’s the most authentic guy in our politics.” – Scott Jennings (17:00)

• On Diversity of Political Thought:

  • “When a prominent African American conservative rises up, they're ignored or attacked relentlessly... Clarence Thomas is a great example.” (37:51)

• Fatherly Pride and Roots:

  • “I’m the son of a garbage man and a factory worker from West Kentucky. If not but for McConnell’s scholarship program, I don’t know that I would have been able to go to college.” (45:12)

• On Courage and the Call to Public Service:

  • “Public service is a calling. I've heard the calling. It's in me. I want to do it someday. I don't know when.” (54:06)

• Moral Clarity on Israel and Terrorism:

  • “What happened on October 7 is one of the biggest acts of barbarism and savagery we've seen in modern history... we have to be able to tell the difference between right and wrong.” (63:58)

Timestamps for Important Segments

• 00:38: Jennings on double standards in media, Biden vs. Trump health narratives
• 03:39: Reflections on Trump’s rapid action and staff
• 09:08: Trump’s near-death experience in Butler, PA and its political/personal impact
• 13:55: Discussion on Jennings’ rise in profile and CNN’s debate format
• 21:38: How Scott stays calm and focuses in heated debates
• 24:54: Advice on being authentic and why less can be more in debates
• 28:03: Jennings’ most memorable on-air moment—Trump’s 2024 win reaction
• 33:59: Lessons from the 2012 Romney campaign and media caricature
• 37:01: Critique of identity-based hiring vs. merit
• 45:09: Jennings on his career path and consistent GOP values
• 49:36: The question of term limits and personal responsibility in aging politicians
• 55:19: Reflection on his father’s early support of Trump and changing political landscape
• 59:09: Legacy, fatherhood, and the motivation for public work
• 62:54: Truth, courage, and the changing media information ecosystem
• 63:58: The yellow ribbon—solidarity with Israeli hostages and moral clarity

Conclusion

Scott Jennings provides a frank, insightful, and at times deeply personal perspective on American politics, media, and leadership. His conversation with Sage Steele illustrates the power of authenticity, the need for respectful but rigorous debate, and the enduring value of truth-telling—even (or especially) in contentious times. The episode is rich with anecdotes, arguments, and moments of vulnerability, making it essential listening for anyone seeking to understand contemporary political punditry and the personal convictions that animate it.

End of Summary