Democrats need to stop being ‘boring’ (with Jack Schlossberg) | The Conversation episode artwork

EPISODE · Jun 21, 2026 · 39 MIN

Democrats need to stop being ‘boring’ (with Jack Schlossberg) | The Conversation

from The Playbook Podcast · host POLITICO

Jack Schlossberg joins Dasha to talk about his campaign for New York’s 12th congressional district, his viral online persona and why he thinks Democrats need to be more “controversial” in the Trump era.  Schlossberg discusses what he says Democrats got wrong in 2024, why he believes attention is political power, how the party can reach young male voters, and why he sees himself as part of a new generation trying to change Democratic politics. He also weighs in on his Kennedy family legacy, RFK Jr., Israel and Gaza, impeachment, super PAC spending, and why he says he has “no regrets” about anything he’s posted online. Have thoughts for the show? Text or leave us a voicemail at 202-643-1536.

Jack Schlossberg joins Dasha to talk about his campaign for New York’s 12th congressional district, his viral online persona and why he thinks Democrats need to be more “controversial” in the Trump era.  Schlossberg discusses what he says Democrats got wrong in 2024, why he believes attention is political power, how the party can reach young male voters, and why he sees himself as part of a new generation trying to change Democratic politics. He also weighs in on his Kennedy family legacy, RFK Jr., Israel and Gaza, impeachment, super PAC spending, and why he says he has “no regrets” about anything he’s posted online. Have thoughts for the show? Text or leave us a voicemail at 202-643-1536.

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Democrats need to stop being ‘boring’ (with Jack Schlossberg) | The Conversation

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This episode was published on June 21, 2026.

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Jack Schlossberg joins Dasha to talk about his campaign for New York’s 12th congressional district, his viral online persona and why he thinks Democrats need to be more “controversial” in the Trump era.  Schlossberg discusses what he says Democrats...

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