Sarah Longwell, pollster, and Tim Miller, ex-Republican strategist, dissect the minds of ex-Trump voters considering Biden. Topics include persuading voters, legal challenges' impact, media biases, and engaging in respectful political discussions.

Sarah Longwell, Publisher of the Bulwark, and Jonathan V. Last, its Editor, dive into the recent election results, revealing a disenchanted voter base dissatisfied with mainstream politicians. They discuss the shortcomings of Biden’s campaign messaging and how demagoguery resonates more than infrastructure bills. The duo reflects on the shifting political landscape and the urgency of protecting democracy. They also touch on the effects of Trump’s influence and the need for authentic outreach to voters amid rising dissatisfaction.

Jon chats with Sarah Longwell, a seasoned pollster who analyzes swing voter reactions, about Kamala Harris’ presidential campaign. They dive into undecided voters' feelings following Biden's withdrawal, the impact of social media, and the intricate perceptions surrounding Harris’ identity. Voter concerns over Harris's viability against Trump and the necessity for a hopeful campaign message are explored, alongside the importance of authenticity in political discourse to engage key demographics.

Republican strategist Sarah Longwell discusses persuading Republican voters to switch from Trump to Biden, analyzing the impact of Trump's felony conviction. Insights into messaging tactics, targeting disillusioned GOP voters, and Biden's campaign strategy to win swing states and undecided voters.

Political strategist Sarah Longwell discusses Trump's financial challenges, selling bibles for legal expenses, and targeting Nikki Haley voters. Lis Smith talks about Robert F. Kennedy's VP pick and countering third-party threats. The podcast explores Biden's economic messaging, Trump's merchandising ventures, campaign fundraising impact, and building an anti-Trump coalition. It also touches on swing voters, women's history month celebrations, and the controversy surrounding the VP selection process.

Political strategist Sarah Longwell discusses the tribal instinct that drives politics in the US, and shares her experience trying to convince people to vote against their political party. Emphasizing the importance of telling a better story about democracy, she explores breaking tribalism, appealing to disaffected Republicans, and valuing democracy over party.

Anna Greenberg, a Democratic pollster, and Sarah Longwell, a Republican strategist and publisher of The Bulwark, join the discussion to dissect the surprising factors behind Donald Trump's electoral victory. They explore shifts in voting dynamics, particularly among women and Latinos, and how economic concerns are reshaping voter behavior. Insights into Trump's appeal and the motivations of his supporters reveal a complex landscape for both parties. The conversation emphasizes the need for Democrats to recalibrate their outreach strategies in an evolving political climate.

Sarah Longwell, a Republican political strategist and co-founder of The Bulwark, discusses the critical political landscape ahead of the 2024 election. She delves into the complexities of undecided voters and the emotional weight of topics like abortion in political engagement. Longwell also emphasizes the importance of listening through focus groups to bridge divides and combat misinformation. Additionally, she explores how AI can transform political communication, questioning its impact on authenticity and trust in messaging.

Sarah Longwell from The Bulwark discusses the GOP's reaction to Hunter's conviction, Trump's potential VP picks, and the impact on the Biden campaign. They also analyze therapy for celebrating wins, the intersection of abortion and economy in politics, local campaign organizing, and speculations on debate tactics and VP selection.

Political strategist Sarah Longwell and columnist A.B. Stoddard discuss Trump's controversial activities, Nikki Haley's endorsement, Biden's policies, and voter perspectives. The podcast also touches on political collusion, women's rights challenges, and casual weekend conversations.