As the nation heads into the 2026 midterm elections, questions about race, class, and the future of America’s cities are once again at the center of public debate. This talk explores what Ray Flynn’s Boston—its neighborhood politics, its struggles over inequality, and its experiments in progressive urban governance—can teach us about those challenges today. Drawing on The Battle for Boston, author Don Gillis joins former Mayor Raymond L. Flynn and longtime policy advisor Neil Sullivan to examine how the city confronted housing segregation, tenant rights, and neighborhood development in an era of deep social division. Their conversation offers a historically grounded look at how cities navigate conflict, build coalitions, and shape democratic life—insights newly resonant as voters prepare to head to the polls.