Discussing Biden's potential moves, the worst and weirdest of the Republican convention, and winning elections in Wisconsin. The guests explore Trump's persona, social media comparisons, and the impact of the Dobbs decision on abortion access. With a trivia game about Wisconsin and playful banter, the episode offers a mix of political insight and humor.

Errin Haines, Jill Habig, and Tyler Yarbro discuss judicial gerrymandering, Florida's abortion laws, Justice Sotomayor's potential retirement, and the impact of conservative efforts on state courts. They highlight the fight for reproductive rights, political complexities, and challenges to prosecutorial independence in various regions.

Errin Haines, a political journalist celebrated for her sharp insights, joins Jessica Tarlov, cohost of Fox News's The Five, to discuss the nuances of the current election season. They analyze Kamala Harris's push to win over women voters and Trump's unusual appeal to this demographic. Tarlov shares her experiences as a Democrat in a conservative space, revealing the challenges and strategies for engaging with opposing views. The conversation also touches on the complexities of political messaging and the importance of addressing undecided voters in today's polarized climate.

Former U.S. Attorney and legal experts discuss the two-tiered justice system and Trump's legal tactics, detailing the upcoming Hush Money trial. They cover racial disparities in sports coverage, dire humanitarian crisis in Gaza, and courthouse security preparations for high-profile trials.

Errin Haines, Editor-at-Large for The 19th and a prominent voice on women's rights, dives into the implications of Donald Trump's return to the White House. She discusses the emotional fallout from the election and the challenges ahead for women's rights. Demographic voting behavior and the paradox of reproductive rights are examined, revealing a complex political landscape. Haines also critiques the Democratic Party's strategies and underscores the urgent need for solidarity in navigating upcoming battles over women's rights.

Charlamagne tha God, an influential host known for his thought-provoking political commentary, joins journalist Errin Haines and LaTosha Brown, co-founder of Black Voters Matter, among others, for a live discussion on election night. They dive into the emotional challenges of voter engagement, especially in Black communities. The panel reflects on grassroots mobilization and the implications of systemic racism surrounding elections. Insights on Kamala Harris’s role in the political landscape and the necessity of young voices in shaping the future are also highlighted.

Brittany Packnett Cunningham, an activist and educator, joins sports journalist Cari Champion and Errin Haines, founder of The 19th, to discuss their collective vision for change as 'The Machetes.' They explore Kamala Harris’ impact on diversity in politics and the importance of unity within the Democratic party. The conversation ignites excitement around civic engagement and the power of grassroots movements. They also reflect on the historical contributions of Black women and how to dream bigger for the future.

Jemele Hill, a sharp political commentator, joins Elie Mystal, a legal analyst with a keen eye on justice, and Errin Haines, a journalist dedicated to race and equity. They discuss the political dynamics seen in the Trump-Harris debate, highlighting critical moments and audience reactions. The conversation flows from the significance of economic issues to the crucial role of live fact-checking. They also tackle complex social topics, including racial identity in politics, while keeping the tone lively with humor and relatable anecdotes.

Kamala Harris, the newly minted Vice President and candidate, faces off against former President Donald Trump in a high-stakes debate. Errin Haines, an editor-at-large for The 19th, analyzes the critical strategies Harris must use to win over undecided voters. The discussion touches on Trump's alarming threats regarding election integrity and the political fallout with the NYPD commissioner’s resignation. As both candidates prepare, the episode dives into the contrasting campaign approaches and the debate's potential impact.

Michael Bennet, Colorado’s senior U.S. Senator, and Errin Haines, an editor-at-large of The 19th, break down Donald Trump’s recent appearance at a major event in Chicago. They delve into the implications of Trump's rhetoric on race, especially regarding his treatment of the African-American community. The conversation also touches on Kamala Harris's inspiring political journey amidst the chaos and challenges of navigating identity politics. They emphasize the need for systemic change to combat economic inequality and discuss the resilience of Black women in leadership.