Sherwin Hughes takes a deep dive into the legacies of Milwaukee’s past mayors and how their leadership shaped the city we know today. From the era of Frank Zeidler to the more recent tenures of Tom Barrett and others, Sherwin examines their policies, triumphs, and shortcomings. He uncovers how each administration influenced the city's economic development, racial dynamics, and urban growth—and how the decisions made decades ago still reverberate in Milwaukee's challenges today. With sharp commentary and a historical lens, Sherwin explores the question: What does Milwaukee’s past tell us about its future, and what lessons can be learned from its mayors? Join him for an engaging discussion of leadership, politics, and the evolution of one of the Midwest's most complex cities.