How Do We Push Back on Authoritarianism? (Crooked Con)

What It Covers

Pod Save America hosts conversations from Crooked Con featuring Democracy Forward's Skye Perryman and Democracy Defenders Fund's Norm Eisen on litigation strategies against Trump, plus campaign strategists Alex Ball (Mikey Sherrill), Morris Katz (Zoran Mamdani), and Samson Signore (Abigail Spanberger) analyzing their 2025 gubernatorial victories in New Jersey, New York, and Virginia through affordability-focused messaging.

Key Questions Answered

• •Litigation as narrative tool: Democracy Forward and Democracy Defenders Fund filed over 200 cases against Trump administration actions, using court filings to expose government misconduct in a fractured media environment where investigative journalism lacks resources. Court documents detailing individual stories of harm now drive public narratives, with journalists reporting on legal filings rather than lawyers following news coverage, fundamentally shifting how information reaches voters.
• •Affordability messaging dominance: All three winning campaigns centered exclusively on cost reduction rather than Trump's personality or culture wars. Spanberger won Virginia by 15 points, the largest margin since JFK, by focusing on economic consequences of Trump policies like federal workforce cuts and healthcare premium spikes. Sherrill led on traditionally Republican traits including lowering taxes and utility costs by summer 2024, winning 25 percent of Republicans.
• •Early paid media strategy: Spanberger campaign started paid advertising months earlier than typical Virginia races to credential the candidate as former CIA officer and federal law enforcement focused on economy before Republicans deployed 80 million dollars in anti-trans attack ads. This inoculation approach made culture war messaging fall flat because voters already associated the candidate with economic solutions rather than social issues.
• •Influencer infrastructure building: New Jersey campaigns developed 35 political influencers as alternative to dying legacy media, creating special access events and coordinated ecosystem. Traditional polling missed results by double digits, with one poll showing Ciattarelli winning black voters 60-40 when Sherrill actually won 95-5. Digital infrastructure proved essential where conventional media coverage consistently underestimated campaign momentum and misread voter sentiment.
• •Cross-partisan coalition building: Mamdani won over 10 percent of Trump voters and flipped Trump-won neighborhoods while increasing turnout in immigrant communities. Democracy Defenders Fund recruited two dozen conservatives including Bill Kristol and Freedom Caucus founder Joe Walsh for Supreme Court briefs on tariffs, demonstrating issues transcend partisan labels. Successful campaigns built coalitions across ideological spectrum rather than conforming to establishment electability assumptions.
• •Questionnaire elimination proposal: National organization questionnaires force candidates to check boxes on policy positions for endorsements and resources, creating vulnerability to opposition research. These intensive forms particularly trap state house candidates without experience into positions used against them in attack ads. Replace written questionnaires with candidate interviews allowing nuanced discussion rather than binary yes-no responses that provide ammunition for opponents.