Former RNC Chair and MSNBC host Michael Steele comes to the table with a candid, funny, and deeply personal conversation about his accidental rise through the Republican Party and the moral compass that guided his leadership. We reflect on the loneliness of party chairmanship, Chair Steele’s resistance to Trumpism, and the broken culture of politics today. With stories from the farm to the convention floor, this episode is part family reunion, part political therapy. And ends with one of our best-ever Sit Your Ass Down Awards. -- Timestamps -- 00:00 - From South Carolina Farms to Political Stages 05:34 - Reshaping the Presidential Primary Process 13:01 - Michael Steele's Unconventional Journey to Politics 28:45 - Inside the Fight to Change Political Party Culture 43:55 - Michael Steele on the GOP's Current State 01:03:18 - Navigating Political Futures, SYAD, and Final Reflections

U.S. Representative Lauren Underwood of Illinois joins us to talk about the moment she left a career in health care to run for office—and the fight that’s kept her going. From defending the ACA to confronting America’s maternal health crisis, she brings both policy chops and personal stakes to her work as one of the most effective members of Congress. She breaks down what power really looks like in Washington, how the Congressional Black Caucus uses it, and why the difference between life and death for millions too often comes down to politics. Also: Congress is just like middle school. -- Timestamps -- 00:00 - Lauren Underwood's Journey to Capitol Hill 05:37 - How Congresswoman Underwood Gets Bills Passed 09:59 - The Fight for the House in 2026 15:10 - A Nurse's View on America's Broken System 18:27 - The Black Maternal Health Caucus 25:33 - Seniority and Impact in the Black Caucus 36:54 - Hobbies and Friendships in the Halls of Congress 43:40 - SYAD 48:40 - Credits