Rick Wilson on Trump, the Midterms, and If a Blue Tidal Wave is Coming
Sep 26, 2026 · 49m
Andy Ostroy and guest Rick Wilson discuss the Supreme Court's ruling on voter rolls, Trump's media ban, and his chaotic UN speech.
S.E. Cupp on Trump, the MAGA Meltdown, the Midterms, the Media Ban, and More
Sep 24, 2026 · 39m
Andy Ostroy and Se Cup discuss the emerging political inflection point against Trump, driven by voter embarrassment and economic betrayal.
Mark McKinnon on 9/11, 'Trump-a-palooza', Paxton v Talarico and Texas Politics, the Midterms, and More
Sep 12, 2026 · 1h 2m
Host Andy Ostroy marks the 25th anniversary of 9/11 by reflecting on personal memories and contrasting George W.
Jessica Tarlov on her New Book, Role on The Five, and if Civil Discourse is Possible in Donald Trump's America
Sep 10, 2026 · 32m
Jessica Tarlov discusses her debut book, *I Disagree: Winning Arguments Without Losing Friends*, which blends memoir with practical advice on constructive debate.
Michael Steele on Trump, DSA, Republican Incompetence, the Midterms, and More
Aug 29, 2026 · 54m
Andy Ostroy and Michael Steele analyze the upcoming midterms, arguing that Trump’s self-serving spending and economic policies are hurting Republican candidates.
Julie Roginsky on DSA, Michigan, Florida, the Midterms, and Natale Harp and the Divinity of Donald Trump
Aug 22, 2026 · 1h 15m
Andy Ostroy and guest Julia Rozinski analyze recent Democratic primary upsets, debating whether progressive victories in Florida and Michigan signal a party shift or a general election liability.