Jon Lovett, co-founder of Crooked Media and host of "Lovett or Leave It," engages in a thought-provoking discussion with Tim Miller. They tackle how the worst people feel validated in their beliefs while the best are filled with uncertainty. Lovett shares insights on the alarming normalization of Trump's practices, particularly regarding immigration policy. They explore the emotional toll of political disillusionment and emphasize the importance of resilience in facing a tumultuous climate. Laughter and reflection flow as they navigate the complex landscape of contemporary American society.

Bill Kristol, a prominent conservative commentator and author known for his Never Trump stance, joins Tim Miller to discuss the alarming shift in U.S. politics. They explore Trump's team potentially selling out Ukraine and the implications of Elon Musk's increasing involvement in political affairs. Kristol shares insights on how key Senate Republicans may compromise constitutional duties and cautions against election denialism on both sides. The episode reflects on the power of wealthy individuals in shaping global diplomacy against the backdrop of rising tensions.

James Carville, a legendary Democratic strategist known for his impactful role in Bill Clinton's campaigns, joins Tim Miller for a lively discussion. They tackle how Trump has betrayed his voters and the political narratives that could define the opposition. Carville critiques Kamala Harris' recent appearance on "The View" and its implications for her future. They ponder the need for the Democrats to re-engage with working-class voters and reconsider their messaging to shake off the grip of identity politics.

Ben Wittes, Editor-in-chief of Lawfare and a senior fellow at the Brookings Institution, dives into the chaotic landscape of Trump’s legal battles. He argues that the justice system failed democracy, as Trump's indictments seemed to enhance his appeal among supporters. The conversation also touches on the implications of judicial decisions and the erosion of democratic norms. Wittes reflects on the political ramifications of past actions, including the U.S.'s stance on Ukraine, and the emotional toll of navigating these tumultuous times.

Tom Nichols, a Professor emeritus at the Naval War College and Atlantic staff writer, dives into the complexities of American politics. He discusses the necessity of confronting Trumpism directly to secure a democratic future. The conversation highlights the shifting motivations of Trump voters, critiques Democratic disconnects, and examines the decline of incumbent parties ahead of 2024. Nichols stresses the importance of accountability, citizen engagement, and the challenges of election coverage in an increasingly chaotic political landscape.

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.

David Frum, an astute political commentator and author renowned for his insights on American politics, joins Tim Miller for a thought-provoking discussion. They reflect on how Never Trumpers should take pride in standing against a perceived fraud. Frum suggests that voting for Kamala Harris represents a blend of progressive and conservative choices. They delve into the complexities of the Electoral College, the emotional dynamics of candidates, and the current challenges facing the Republican Party—all while teasing Tim's final predictions for the election.

Bill Kristol, a prominent conservative political commentator and contributing editor at The Bulwark, joins Tim Miller to discuss the shifting dynamics of current elections. They dive into the gender gap in early voting, particularly linked to abortion, and analyze how the Dobbs decision could shape the political landscape. Kristol also critiques the Trump team's handling of these issues, touches on concerning voter trends, and reflects on the implications of violent rhetoric in today’s politics.

Ann Selzer, President of Selzer & Company and renowned Iowa pollster, discusses a surprising lead for Kamala Harris in Iowa's polls. She highlights how shifting voter sentiments, particularly among women 65 and older, play a crucial role in this unexpected trend. The conversation dives into the implications of Iowa's new strict abortion law and how it may be reshaping political dynamics. Ann emphasizes the complexities of polling accuracy and the importance of understanding demographic trends in navigating electoral outcomes.

Mehdi Hasan, editor-in-chief of Ziteo and author of 'Win Every Argument,' joins Tim Miller for a deep dive into political dilemmas. They critique misleading media narratives around Trump's presidency and the accountability necessary for historical events like January 6th. The conversation shifts to the role of young voters, especially within Arab American communities, and the troubling rise of divisive political ads. Hasan also addresses the curious case of Jill Stein and the risks she poses for electoral strategies, all while balancing anxiety about Trump's potential comeback with a sense of hope.