The Great Battlefield

Jesse Leyrich, a Democratic strategist, writer, and media creator, joins the conversation to examine who might lead Democrats into 2028. He discusses promising contenders, Obama’s organizing legacy, authenticity in political communication, and lessons from Hillary Clinton’s 2016 campaign. He also explores disinformation, party renewal, independent voters, competitive primaries, and building political media through newsletters, podcasts, and viral clips.

Jackie Payne, founder of Galvanize USA and Galvanize Action, discusses mobilizing moderate women through research, culture, and digital storytelling. She explores the rise of Dear Grace, AI and news habits, economic anxiety, political distrust, and the leadership traits undecided voters seek. The conversation also examines long-term civic engagement and resisting authoritarianism without deepening polarization.

Jen Thompson, a lawyer, former Republican campaign manager, and higher-education leader, recounts managing Jim Talent’s 2002 Senate victory and the doubts that changed her political path. She explores her conservative upbringing, a life-altering car accident, starting over in Australia, decades spent writing Wild Pivot, therapy, Trump’s ego, political deconversion, and finding courage through memoir and Substack.

Ty Cobb, an attorney and former federal prosecutor who served as special White House counsel, reflects on his career and time in the Trump administration. He discusses Trump’s character, the loss of institutional guardrails, Republican submission, presidential immunity, and threats to election integrity. Cobb also explores democratic resistance, accountability, civic engagement, and why Trumpism could persist through 2028.

Ben Brodsky, a political digital consultant and founder of Common Sense Empathy, discusses the evolution of online political organizing. He explores how the Tea Party mobilized through Facebook, better ways to moderate and analyze comments, and the challenges of building on an unpredictable platform. The conversation also covers influencers, paid persuasion, anonymity, and creating more responsible digital communities.

Susannah Randolph, a Florida environmental and political organizer and Sierra Club Florida director, traces her path from grassroots activism to campaigns and congressional politics. She recalls a massive voter-registration drive, viral attacks on Rick Scott, and a difficult congressional race. Randolph also explores Florida’s rightward shift, voting restrictions, data centers, cross-party environmental organizing, and the state’s political future.

Doug Gordon joins The Great Battlefield podcast to talk about his career in political communications and co-founding Upshift Strategies, where they help progressive organizations develop compelling messaging.

Eric Ming joins The Great Battlefield podcast to talk about his career in politics and how the State + Local Election Alliance is working to elect local officials who will protect democracy.

Garrett Gruener returns to The Great Battlefield podcast to talk about how he's building relational organizing and social networking tools with the use of AI.

Kunal Goel joins The Great Battlefield podcast to talk about his career, including his time at BallotReady and starting his own firm Kunal Unplugged, where he's helping political tech startups and advocacy groups turn research into high performing content.