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On with Kara SwisherOn with Kara Swisher

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

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…

Ben WiklerguestKara Swisherhost
Jul 23, 202652mWatch on YouTube ↗

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At a glance

WHAT IT’S REALLY ABOUT

Ben Wikler’s roadmap to unrig democracy and beat Trumpism

  1. 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.
  2. He uses the 2025 Wisconsin Supreme Court race—where Susan Crawford beat a Musk-backed effort—as a case study for how clear messaging and grassroots organizing can defeat big-money intimidation tactics.
  3. Wikler says Democrats must run a year-round “permanent campaign” focused on neighborhood teams, relational organizing, and listening that builds trust long before Election Day.
  4. He contends that winning in 2026 state-level offices (governors, secretaries of state, attorneys general, legislatures) is pivotal to preventing election sabotage in 2028 and beyond.
  5. He lays out a sequence of structural reforms—especially ending the Senate filibuster—followed by voting rights measures, anti-gerrymandering changes, Electoral College workarounds, and Supreme Court term limits to “unrig” governance.

IDEAS WORTH REMEMBERING

5 ideas

Wikler frames today as a familiar cycle of oligarchic capture—on faster-forward.

He describes cycles where concentrated wealth tries to “lock in” control, followed by waves of public pushback that rewrite rules to expand democracy. He argues today’s accumulation is faster and potentially supercharged by AI, increasing the urgency of “unrigging” government.

Wisconsin’s 2025 court race is presented as proof that Musk-style money politics can be beaten.

He recounts how the Wisconsin Supreme Court election became a test of whether elections can be “auctioned off,” with Musk funding ads, door-knocking, and offering million-dollar incentives. Wikler says Susan Crawford’s decision to confront Musk directly—rather than avoid provoking him—helped crystallize a simple anti-corruption message.

Control of rule-setting offices (courts, states, localities) is as decisive as winning top-of-ticket races.

Wikler argues winning one marquee race isn’t enough because state legislators, judges, mayors, and other offices “make the rules” that shape everything from voting access to gerrymandering. In Wisconsin, he says the “skeleton key” to unrigging maps was flipping the state Supreme Court majority, after other avenues failed.

He argues Democrats should reallocate focus from late ad bursts to early, sustained organizing infrastructure.

He defines a “permanent campaign” as year-round, neighborhood-level organizing and trust-building—not nonstop TV ads. He says organizing is relatively cheap compared with paid media, but only works when funded early and continuously rather than in the final weeks.

Relational organizing and large-scale listening are positioned as the highest-leverage persuasion tools.

Wikler says the most persuasive voter contact comes from someone the voter trusts, and he claims Musk tried to “manufacture” relational organizing with paid petition/referral schemes. He argues Democrats should do more genuine relational organizing and listening (“bridge-building”) year-round to build trust.

WORDS WORTH SAVING

5 quotes

Go back across the history of the country. There are waves of power that accumulate in a tiny number of hands and people trying to lock in their power and control, and then there are waves of the public rising up and then changing the rules to be able to protect the idea of democracy and expand the circle of freedom.

— Ben Wikler

I feel like he approached politics the way he approached Doge — which is to have a big theory and then apply it without paying any attention to whether it was actually working.

— Ben Wikler

This is why often talking about democracy is actually the worst message if you wanna save democracy. You should, you should focus on what it is that people wanna change in their own lives and how, how the government can be on their side.

— Ben Wikler

We're in a situation right now where no party is likely to get sixty votes in the Senate to overcome a filibuster, and where both parties have a political incentive to stop the other side from doing big things.

— Ben Wikler

We should have the expectation that Trump will use every one of his powers to try to stop the democratic process from working.

— Ben Wikler

Read the available transcript
Wealth and power concentration; plutocratsAI and accelerating wealth accumulationWisconsin Supreme Court race and Elon Musk’s spendingRelational organizing and trust-buildingPermanent campaign and local party infrastructure2026 state-level offices and election protectionFilibuster abolition and democracy reforms (NPVIC, gerrymandering, D.C./Puerto Rico, Supreme Court term limits)

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."

High quality AI-generated summary created from speaker-labeled transcript.

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