Summary
Overview
A special episode featuring conversations from CrookedCon about fighting the Trump administration and lessons learned from successful 2025 Democratic campaigns. Features legal strategists Skye Perryman and Norm Eisen discussing their litigation efforts against Trump, followed by campaign managers from winning races in New York, New Jersey, and Virginia analyzing their victories and the future of the Democratic Party.
Fighting Trump Through Litigation: Strategy and Impact
Skye Perryman of Democracy Forward and Norm Eisen of Democracy Defenders Fund discuss their extensive legal campaign against the Trump administration. They explain how litigation serves not just to stop illegal actions but to empower people to publicly challenge government overreach. Their organizations have filed over 200 cases, winning major battles on issues from birthright citizenship to federal funding, often collaborating with state attorneys general and other advocacy groups.
- Democracy Forward prepared for Trump's second term by studying Project 2025 and planning litigation strategy as early as 2023
- Litigation serves multiple purposes: stopping harmful actions, exposing government misconduct, and empowering people to publicly assert their rights
- The organizations have successfully blocked federal funding freezes, preserved SNAP benefits, stopped birthright citizenship attacks, and saved thousands of civil service jobs
- Norm Eisen filed the first lawsuit against Trump in both of his presidential terms, starting with a Doge membership application that led to discriminatory rejection
- They've met Trump's 'flood the zone' strategy with 'rule of law shock and awe,' filing cases immediately after illegal actions
" The ability to initiate litigation against your government when your rights are violated was a really powerful one, not just to stop terrible things...It's also the ability of people to stand up publicly and say, I have rights that you cannot take away, and I'm going to force you publicly to defend what you were doing to me, what you were doing to my community, and what you were doing to my neighbors. "
" We have met flood the zone with rule of law shock and awe. "
The Role of Litigation in a Fractured Media Environment
The strategists explain how their legal work has evolved to fill gaps left by declining investigative journalism. Court filings now serve dual purposes—winning cases and exposing stories that shape public narratives. They discuss how individual stories from plaintiffs, like deportees and federal workers, have changed public perception and even influenced figures like Joe Rogan. The work involves round-the-clock preparation, with teams working through nights to respond to Trump's actions.
- Court cases now feed news narratives rather than vice versa, with journalists reporting on court filings due to underinvestment in investigative journalism
- Individual plaintiff stories, like Mr. Garcia's case challenging the Alien Enemies Act, have shifted public opinion even among unexpected audiences
- The legal team operates 24/7, with lawyers staying up all night to file cases immediately after Trump actions
- Some cases were drafted months in advance (like the birthright citizenship complaint over summer 2024), allowing rapid response
" What we know about this administration is they know what to do with weakness. They know what to do with it. Split people off, pick people off, engage in a settlement. They do not always know what to do with strength. "
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