Mike Stephen explores the legacy of one of the most successful sports figures of the 19th century with Nancy Hays, author of Riding for America: The Story of Isaac Murphy, Sports Icon of the 19th Century, gets an update on the community-building work of HelloBaby from founder Debbie Frisch, and spotlights Chicago Pride Hockey.

Mike Stephen talks with local food journalist Nick Kindelsperger about his quest to eat at every restaurant in the Loop, learns about the challenges Chicago street vendors face from Maria Orozco, development manager for the Street Vendors Association of Chicago, and discusses an approach to addressing the affordable housing crisis with Illinois Answers Project investigative reporter Alex Nitkin.

Mike Stephen revisits a few previous segments from the show that explore the relationship between brewing, distilling, bar culture, and Chicago history.

Mike Stephen learns how bricks tell the history of Chicagoland with Will Quam, author of the new book Fire and Clay: How Bricks Reveal the Hidden History of Chicago, and then chats with Akele Spencer, a resident of the South Side and member of Southside Together, about his opposition to a new microelectronics park being built in his community.

Mike Stephen discusses the potential impact of food assistance cuts on Illinois grocery stores with Capitol News Illinois reporting intern Jenna Schweikert, learns how the local organization Timeless Gifts brings music education to youth from founder Joan Collaso, and discovers the secret history of local blues guitarist Luther "Guitar Junior" Johnson.

Mike Stephen explores the controversy of Chicago Public Schools using public money to take students to a protest with Nick Kryczka, assistant professor of secondary education for social studies at the College of Education at National Louis University, and then chats with Injustice Watch senior reporter Dan Hinkel about how difficult it is to clear a wrongful conviction in Cook County.

Mike Stephen visits the shop of Mach MachinesMusical Instruments in Oak Park and talks to owner Dave Showalter, chats with Rima Ziuraitis, a Naperville woman who volunteered in the Ukraine War, and discovers the Secret History of guitarist Vince Black.

Mike Stephen talks to Takeout 25 founder Ravi Parakkat about 20fy.ai, an artificial intelligence system that is being used to help local restaurants, gets a preview of Goatstock in Norridge with Music Graphics Chicago co-owners Deb Sonzo and Jamie Riani, and chats with Chicagoan Todd Kessler about his new music.

Mike Stephen visits the Northern Illinois Scholastic Press Association conference to discuss the future of journalism with Prospect High School teacher Jason Block and Prospect seniors Tessa Trylovich and Stella Palm and then discovers the Secret History of jazz guitarist Eddie Condon.

Mike Stephen chats with Roya Samarghandi, chief advocacy and innovation officer at The Chicago Bar Foundation, about a new program that allows residents to get legal aid at their local library, explores the ongoing debate around public money for private schools with Chalkbeat Chicago's Reema Amin, and gets the lowdown on a local organization that helps youth enter the workforce called Leaders in Transformational Education from CEO Candace Thier.