Bulwark Takes: JFK’s Grandson CLAPS BACK at “Fake” Kennedy Politics (w/ Jack Schlossberg) – July 26, 2025
In this engaging episode of Bulwark Takes, The Bulwark team delves into the intersection of legacy, politics, and social media with special guest Jack Schlossberg, the grandson of President John F. Kennedy. Hosted by Tim Miller and Cameron Caskey, the discussion navigates through personal anecdotes, political strategies, and contemporary issues affecting the Kennedy legacy.
Introduction and Guest Background
The episode opens with Tim Miller introducing Jack Schlossberg, highlighting his unique position as a younger voice in a traditionally storied family. Cameron Caskey adds humor by referencing Jack’s YouTube show, Test Drive with Jack Schlossberg, emphasizing Jack’s modern approach to engaging with audiences.
Jack Schlossberg shares insights into his recent ventures:
“[00:24] Jack Schlossberg: Let's get started.”
Social Media Strategy and Political Engagement
A significant portion of the conversation centers on the utilization of social media in modern political campaigns. Tim and Cameron discuss the challenges and opportunities Democrats face in engaging younger demographics online. Jack provides his perspective on effective digital strategies, stressing the importance of authenticity and risk-taking.
Cameron Caskey critiques the Democratic Party’s hesitancy:
“[15:26] Cameron Caskey: It was like, I was like, I don't want to, like, like, this was like, what, 2023?”
Jack concurs on the need for more aggressive social media tactics:
“[20:56] Cameron Caskey: We're doing it now... like speaking directly.”
RFK Jr., Epstein Files, and Conspiracy Theories
The discussion takes a critical turn towards Robert F. Kennedy Jr. and the controversies surrounding him, particularly in relation to the Epstein Files. The hosts express frustration with how legacy figures are co-opted for contemporary political agendas.
Tim Miller addresses the complexities of confronting conspiracy theories:
“[27:09] Tim Miller: Probably it works when Trump does it...”
Jack Schlossberg emphasizes accountability:
“[30:09] Cameron Caskey: That's kind of what I mean...”
The conversation highlights the tension between maintaining a respected family legacy and addressing current political misinformation.
Democrats' Social Media Challenges
The trio debates the effectiveness of Democratic strategies on platforms like TikTok and Instagram. Cameron Caskey points out the need for clear messaging and embracing new forms of communication to resonate with younger voters.
Jack Schlossberg comments on language usage:
“[40:01] Jack Schlossberg: Them calling things coded. Everything isn't something coded.”
Rapid-Fire: Gen Z Trends and Pandemic Activities
In a lighthearted segment, Tim, Cameron, and Jack engage in rapid-fire questions about Gen Z trends and activities during the pandemic.
Cameron Caskey shares personal experiences:
“[41:51] Cameron Caskey: I don't really think in terms of like, that's Gen Z.”
Jack Schlossberg humorously critiques certain trends:
“[39:53] Tim Miller: Okay, Dante, put 10 points on the screen.”
Boomer Mailbag: Social and Political Expectations
The hosts address listener questions, touching on sensitive topics like consent in Gen Z relationships and the portrayal of LGBTQ+ individuals in politics.
Old Vanilla's Question:
“Gen Z women are expected to consent to being choked and slapped during sex. Is this common or just sensationalized?”
Cameron Caskey responds thoughtfully:
“[53:23] Cameron Caskey: Is it common to be expected? I don't know.”
Closing Thoughts and Future Discussions
As the episode wraps up, the hosts reflect on the evolving nature of political engagement and the importance of leveraging digital platforms to foster meaningful change. They hint at future discussions, including a deeper dive into Hunter Biden’s defense and the broader implications of political legacy.
“[59:20] Tim Miller: Thanks for watching, folks.”
Notable Quotes
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Jack Schlossberg on social media engagement:
“[20:56] Cameron Caskey: We're doing it now... like speaking directly.”
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Cameron Caskey on Democratic Party’s approach:
“[15:26] Cameron Caskey: It was like, I was like, I don't want to, like, like, this was like, what, 2023?”
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Tim Miller on Gen Z activism:
“[57:15] Tim Miller: I think young people have seen these big marches happen...”
Conclusion
This episode of Bulwark Takes offers a comprehensive look at how legacy figures like Jack Schlossberg navigate the complexities of modern politics and social media. Through candid conversations and insightful critiques, Tim, Cameron, and Jack explore the challenges Democrats face in engaging younger voters and maintaining a respected family legacy amidst contemporary political turmoil.
Whether you're a longtime listener or new to Bulwark Takes, this episode provides valuable perspectives on the evolving landscape of American politics and the role of social media in shaping public discourse.