Jack Schlossberg
Design Matters with Debbie Millman
Design Matters Media
4.5 • 1.3K Ratings
🗓️ 9 March 2026
⏱️ 42 minutes
🔗️ Recording | iTunes | RSS
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Summary
Jack Schlossberg—writer, lawyer, political correspondent, and the only grandson of President John F. Kennedy—joins live at the On Air Fest to discuss political legacy, internet culture, and the future of Democratic leadership. With humor and candor, he reflects on growing up in a historic political family, the power and peril of social media, the spread of misinformation, and why authenticity and risk-taking are essential to reaching a new generation of voters.
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Transcript
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| 0:00.0 | I've never been less happy to be proven right. |
| 0:03.3 | It wasn't actually that complicated. |
| 0:05.4 | It was just as obvious as it seemed, |
| 0:07.8 | but you just couldn't believe that the people in charge had missed it. |
| 0:14.6 | From the TED Audio Collective, this is Design Matters with Debbie Millman. |
| 0:21.8 | On Design Matters, Debbie talks with some of the most creative people in the world about what they do, |
| 0:26.8 | how they got to be who they are, and what they're thinking about, and working on. |
| 0:31.0 | On this episode, a conversation with Jack Schlossberg, a young candidate for the House of Representatives |
| 0:37.1 | who says that Democrats are way behind Republicans in new media. |
| 0:41.9 | You watch one workout video and you're in this right-wing ecosystem of macho dudes saying insane stuff that's all Trump coded. |
| 0:54.5 | This interview took place on Wednesday, February 25th, 2026 in front of a live audience at the |
| 1:01.0 | on-air fest in Brooklyn. |
| 1:03.0 | My guest today, I just want to give you a little bit more background, was born into one of the |
| 1:09.6 | most storied families in American history. |
| 1:13.1 | But what fascinates me most about him is not his inheritance, but how he's choosing to reinterpret it. |
| 1:22.2 | Jack Schlossberg is the only grandson of President John F. Kennedy, but he is also a writer, a lawyer, |
| 1:29.5 | a political correspondent, a climate advocate, a paddleboarder, and an occasional provocateur. |
| 1:36.6 | At a moment when faith in institutions feels fragile and truth feels negotiable, |
| 1:43.5 | Jack is asking what leadership looks like now and whether optimism has a place in American |
| 1:49.5 | life. |
| 1:50.0 | So I'd like to welcome everybody here in joining Jack Schlossberg and I to this very special |
| 1:56.4 | live episode of Design Matters on the on air fest stage. |
... |
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