In this special episode, Sherwin sits down with former Milwaukee Mayor Tom Barrett for an honest and wide-ranging conversation about the city's challenges and progress during Barrett's tenure. From tackling segregation and economic inequality to navigating political tensions and public health crises, Sherwin and Mayor Barrett reflect on the decisions that shaped Milwaukee — and the lessons that can guide its future. Tune in for candid insights, behind-the-scenes stories, and a hopeful look at what it takes to lead a divided city toward unity and growth.