One man’s bold plan to defeat Trumpism—once and for all

ℹ️ EPISODE INFO

Released

July 23, 2026

Duration

52m

Channel

On with Kara Swisher

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

Can Democrats actually beat Donald Trump—and if so, how? Kara sits down with political strategist Ben Wikler, former chair of the Wisconsin Democratic Party and author of This Is the Plan, to break down what Democrats need to do before the 2026 midterms and the 2028 presidential election. They discuss how Wikler helped defeat Elon Musk-backed candidates in Wisconsin, why he believes Democrats need a permanent organizing strategy instead of campaign-season politics, and why local races may matter more than Washington. They also debate the filibuster, Project 2025, Democratic infighting, election security, AI's role in concentrating wealth and power, and whether America's political system can still be repaired. 00:00 Ben Wikler's plan to save democracy 03:53 Why AI could create unprecedented wealth and power 05:42 How Elon Musk lost Wisconsin 14:29 The Democratic strategy for winning again 19:35 Can Democrats overcome their internal divisions? 29:22 Why Ben Wikler wants to end the filibuster 39:30 What Democrats should do if they win in 2028 45:27 Trump's election strategy and the 2026 midterms 51:33 What Wikler would do as DNC chair Subscribe: https://goo.gl/FRleYo Apple Podcasts: https://podcasts.apple.com/us/podcast/on-with-kara-swisher/id1643307527 Spotify: https://open.spotify.com/show/42ntT7XnfdbbYetUQu0vu5?si=ddbc94321e3948af FOLLOW US Instagram: https://www.instagram.com/onwithkaraswisher/?hl=en TikTok: https://www.tiktok.com/@onwithkaraswisher?is_from_webapp=1&sender_device=pc LinkedIn: https://www.linkedin.com/in/kara-swisher-b7213 Threads: https://www.threads.com/@onwithkaraswisher Bluesky: https://bsky.app/profile/onwithkaraswisher.bsky.social

🎤 SPEAKERS

• Ben Wikler

  guest

  Democratic political organizer and party leader focused on state-level election strategy and pro-democracy reforms.

• Kara Swisher

  host

  Journalist and podcast host of "On with Kara Swisher."

🧾 EPISODE SUMMARY

In this episode of On with Kara Swisher, featuring Ben Wikler and Kara Swisher, One man’s bold plan to defeat Trumpism—once and for all explores Ben Wikler’s roadmap to unrig democracy and beat Trumpism Ben Wikler argues the U.S. is in a rapid new wave of concentrated wealth and power that threatens democratic accountability, with AI potentially accelerating that trend.

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