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On with Kara SwisherOne man’s bold plan to defeat Trumpism—once and for all
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CHAPTERS
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Why “unrigging America” is a recurring fight—and what’s different now
Kara Swisher asks Ben Wikler whether the U.S. is always doomed to cycles of concentrated economic power and political capture. Wikler argues the country repeatedly oscillates between elite power consolidations and public pushback, but says today’s wealth-and-power concentration is accelerating faster than before.
- •Wikler describes historical “waves” of concentrated power followed by waves of democratic reform.
- •He says the current moment features unusually rapid, large-scale accumulation of wealth and influence.
- •Kara frames the discussion around whether business elites inevitably “rig” the system over time.
- •Wikler positions the present as both familiar (historical precedent) and uniquely intense (speed and scale).
AI, platform dominance, and the next acceleration of wealth and power
Wikler connects recent tech-platform dominance to a looming AI-driven concentration of wealth and control. He compares this era to earlier industrial transformations that caused mass job disruption and required labor and progressive reforms to convert growth into broadly shared gains.
- •Wikler argues AI could concentrate economic power even more than prior tech platform shifts.
- •He cites the idea that a few companies can centralize value (e.g., advertising) and destabilize institutions.
- •He compares today’s disruption to the first Progressive Era’s industrial upheaval and migration to cities.
- •He emphasizes that democratic rule-setting and reform were necessary historically to improve living standards.
Wisconsin’s 2025 Supreme Court race as a test case for money and intimidation
Kara turns to Wikler’s Wisconsin experience, focusing on the 2025 Wisconsin State Supreme Court election that drew massive spending and attention. Wikler describes the atmosphere of fear around Elon Musk’s political influence and why the race became a high-stakes test of whether elections could be effectively “bought.”
- •Kara notes the race’s unprecedented spending and Musk’s support for the Republican candidate.
- •Wikler describes a climate where officials in both parties feared attracting Musk’s targeting.
- •He portrays the election as a planned demonstration of Musk-and-Trump political dominance in a “sleepy” down-ballot context.
- •He highlights Musk-backed messaging that linked the judicial race directly to supporting Trump.
How Musk lost: making the contest about democracy being for sale
Wikler explains how Susan Crawford’s message and grassroots organizing reframed the race into a moral and democratic choice. He emphasizes both the clarity of Musk as a foil and the importance of continuing to show up despite fear that challenging a powerful donor could backfire.
- •Wikler recounts Crawford’s line about facing “the world’s richest man in a fight for democracy.”
- •He describes thousands of organizers working through long-standing community relationships.
- •He argues the campaign made the race about whether Wisconsin could be “bought” or “auctioned off.”
- •He discusses the debate over whether attacking Musk would provoke more spending—and says confronting the bully worked.
What Musk got right (and wrong): relational organizing and manufactured trust
Kara asks what Musk did effectively and what failed. Wikler says Musk pursued a theory-driven approach without adapting to results, but correctly recognized that trusted relationships are powerful in turning out and persuading voters—then tried to simulate that with financial incentives.
- •Wikler says the strongest influence on voting is hearing from someone a voter trusts.
- •He describes Musk’s petition-and-referral tactic as an attempt to “manufacture” relational organizing via money.
- •He links similar tactics to other right-leaning organizing strategies and Musk’s America PAC.
- •He argues Democrats have more work to do to scale relational organizing, pointing to efforts he says some groups are making.
The “permanent campaign” model: winning by organizing the whole ballot
Wikler generalizes Wisconsin’s approach into a national strategy that targets every level of government. He argues winning top-of-ticket races isn’t enough; parties must build ongoing local infrastructure to influence low-visibility contests that can cascade into national power shifts.
- •Wikler calls for a “permanent campaign” focused on local organizing rather than nonstop advertising.
- •He says far-right efforts target mayors, judges, and state legislators to shape voting rules and maps.
- •He describes flipping Wisconsin’s Supreme Court majority as the “skeleton key” that unlocked broader reform.
- •He cites examples of small-margin races and voter drop-off in down-ballot contests as decisive.
What races matter most in 2026—and why state control protects 2028
Kara asks which local races deserve attention. Wikler prioritizes governors, secretaries of state, attorneys general, and state legislative races in battleground states, arguing that because states run elections, these offices can block attempts to undermine future presidential outcomes.
- •Wikler says the Constitution places election administration primarily at the state level.
- •He argues Trump’s future attempts to overturn outcomes depend on state-level vulnerabilities.
- •He describes Wisconsin’s 2020 dispute as hinging on a narrow state Supreme Court decision.
- •He outlines battleground-state pathways and emphasizes building protections before 2028.
Managing Democratic internal divisions: debate, primaries, and unifying for the general election
Kara raises tensions between centrists and the left and worries about the Democratic brand. Wikler argues post-loss debate is healthy and often necessary for durable recovery, but says the key test is whether party factions unite after primaries to win general elections.
- •Wikler frames internal conflict as normal and potentially productive after electoral defeat.
- •He says voters want real change and many Democrats feel the party must improve at winning.
- •He stresses the importance of rallying behind nominees immediately after primaries.
- •He contrasts the GOP as centered on one person with Democrats as a coalition held by broad principles.
Making voters feel included: neighborhood teams, listening at scale, and trust-building
An outside question asks how state parties can rebuild legitimacy through process rather than ideology. Wikler describes Wisconsin’s neighborhood teams and “bridge-building” conversations that ask voters what matters to them, aiming to earn trust over years through listening, follow-through, and repeated contact.
- •Wikler describes volunteer neighborhood teams that meet locally and repeatedly engage the same voters.
- •He explains “bridge-building” as asking questions and listening outside election crunch time.
- •He argues trust is scarce and is built by hearing people out, acting, and then reporting back.
- •He warns that abstract democracy messaging can fail if it doesn’t connect to people’s daily needs.
“Field margins” and the case for ending the Senate filibuster
Kara and Wikler discuss razor-thin electoral margins and why that instability makes governing difficult. Wikler argues the core problem is a system that blocks policy delivery, focusing on the filibuster as a structural barrier that prevents majorities from enacting change and fuels public whiplash.
- •Wikler says most races are predictable, but a tiny set of close contests determines control.
- •He argues repeated power swings are historically unusual and driven by dissatisfaction with stalled governance.
- •He claims the filibuster prevents either party from delivering on major issues with narrow majorities.
- •He traces the filibuster’s origins and argues it has increasingly been used to block legislative agendas.
Filibuster objections and accountability: why Wikler still wants it gone
Kara points out the filibuster can also block Trump-aligned bills, raising the tradeoff. Wikler responds that Republicans protect the filibuster because their priorities can often pass through other routes, while the filibuster blocks reforms that would increase accountability and reduce plutocratic “ratchet effects.”
- •Kara raises that the filibuster can stop harmful legislation and “can be abused.”
- •Wikler argues governance in a “straitjacket” undermines democracy and accountability.
- •He contends Republicans’ key goals often don’t require overcoming the filibuster.
- •He labels the SAVE Act a “stunt bill” that many senators prefer not to vote on.
DNC funding, party strategy, and sustaining year-round organizing infrastructure
Kara asks what needs to change at the DNC, referencing financial strain and fundraising challenges. Wikler argues donors respond to clear paths to victory and proposes rigorous targeting of decisive races, while also emphasizing that sustained organizing is comparatively cheaper than paid media and must begin early to build trust.
- •Wikler says parties raise money best by showing how contributions can change election outcomes.
- •He discusses new rules allowing federal party committees to fund candidate campaigns more extensively.
- •He describes Wisconsin’s approach of raising through the party and supporting key races.
- •He argues permanent organizing is cost-effective compared with ad-heavy campaign budgets and must be funded early.
If Democrats win in 2028: sequencing structural reforms from popular vote to court reform
Kara asks what would need to happen under a Democratic governing trifecta and how to prioritize major reforms. Wikler lays out a sequence: state-level action on the National Popular Vote Interstate Compact, then immediate filibuster removal, followed by voting rights and anti-gerrymandering measures, representation reforms, and Supreme Court reform—favoring 18-year term limits.
- •Wikler argues the National Popular Vote Interstate Compact could be advanced through state victories.
- •He calls for ending the filibuster immediately once Democrats have a Senate majority.
- •He discusses national voting rights protections and a ban on partisan gerrymandering.
- •He favors Supreme Court 18-year active-term limits with senior status to reduce partisanship and stabilize the institution.
Midterm risks: Trump’s pressure campaign and defending election administration locally
Kara asks about Trump’s claims of election corruption and threats toward election officials. Wikler expects continued attempts to interfere with election processes and says court challenges can help, but stresses that local and state officials are the critical line of defense and should run scenario planning and preparation.
- •Wikler says Trump will use every available power to obstruct or distort democratic processes.
- •He lists tactics he says Trump has tested before: seizing ballots, seizing machines, and prosecuting officials.
- •He points to ongoing legal preparation to challenge federal overreach in court.
- •He emphasizes local planning, community organizing, poll workers/observers, and early voting to reduce vulnerabilities.
What “half the plan” would change—and what Wikler would prioritize as DNC chair
Kara asks what improvements would result if only part of Wikler’s agenda were achieved, and then asks what he’d do if he ran the DNC. Wikler argues that a national popular vote would transform participation by making every vote matter, and says his top DNC priority would be publishing state-by-state long-term plans that connect local races to national outcomes and motivate sustained engagement.
- •Wikler says a national popular vote would end most voters feeling like “spectators” in safe states.
- •He argues more competitive House elections and anti-gerrymandering measures would broaden meaningful representation.
- •He suggests Supreme Court reform could open possibilities for addressing money in politics.
- •As hypothetical DNC chair, he would create and publicize detailed long-term “unrigging” plans for every state to show how local wins add up.
Publisher timestamps
- 0:00Ben Wikler's plan to save democracy
- 3:53Why AI could create unprecedented wealth and powerRead this chapter
- 5:42How Elon Musk lost Wisconsin
- 14:29The Democratic strategy for winning againRead this chapter
- 19:35Can Democrats overcome their internal divisions?Read this chapter
- 29:22Why Ben Wikler wants to end the filibusterRead this chapter
- 39:30What Democrats should do if they win in 2028Read this chapter
- 45:27Trump's election strategy and the 2026 midtermsRead this chapter
- 51:33What Wikler would do as DNC chairRead this chapter
