Design Matters with Debbie Millman Jack Schlossberg
Mar 9, 2026
Jack Schlossberg, writer, lawyer, political correspondent and JFK's only grandson, reflects on growing up in a famous family and his path into politics and media. He discusses internet culture, misinformation, and why Democrats must take bolder, edgier approaches. He also recounts creating viral truth-telling content and his views on rebuilding trust with younger voters.
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How A 10th Grade Humiliation Sparked A Political Obsession
- Jack Schlossberg discovered his family's political legacy after being called out in 10th grade about Kennedy policy and then devouring books and speeches.
- That moment, paired with the 2008 Obama campaign, turned a mortifying classroom event into a lifelong political obsession.
Why Democrats Lag On Social Media
- Democrats often lose online because they prioritize being correct over being compelling, ceding humor and risk to the right.
- Schlossberg argues that being "cool, fun, edgy" plus clear policy sells better to younger voters.
Climate Action Needs Building Not Just Blocking
- Environmental progress requires building large infrastructure, not only blocking development, which means balancing cheap energy and long-term investment.
- Schlossberg learned this at Harvard where policy debate forced him to learn tools like discount rates.
