Bruce Levine and Mike Esposito opened their show by celebrating the 10-year anniversary of Inside the Clubhouse. Former hosts Wayne Randazzo and Matt Spiegel stopped by to ring in the celebration. Later, Levine and Esposito discussed all the big news of the week, including the Cubs' shocking hiring of Craig Counsell as their new manager and White Sox television play-by-play announcer Jason Benetti leaving the organization for the same position with the Detroit Tigers.

Bruce Levine and Mike Esposito opened their show with Levine sharing his latest reporting on the Cubs' plan to pursue Padres star outfielder Juan Soto on the trade market this offseason. Later, the guys took calls from listeners about what the Cubs and White Sox should do this offseason.

In the second hour, Bruce Levine and Mike Esposito were joined by Cubs legend Andre Dawson to discuss the club's 2023 season and the World Series. Later, Tyler Kepner of the Athletic joined the show to break down an epic Game 1 of the World Series, which saw the Rangers rally for a 6-5 win against the Diamondbacks in 11 innings on Friday. Kepner also shared what he has heard about the Cubs' chances of re-signing center fielder/first baseman Cody Bellinger in free agency.

Bruce Levine and Mike Esposito opened their show by discussing the Cubs' plan to improve this offseason as the start of free agency looms. Later, new White Sox director of player personnel Gene Watson joined the show to discuss his role and his plan for improving the organization's roster and farm system.

In the final hour, Bruce Levine and Mike Esposito were joined by former Cubs manager Joe Maddon to discuss the MLB playoffs, how Phillies sluggers Kyle Schwarber and Nick Castellanos are performing and much more.

David Haugh was joined by MLB Network analyst Dan Plesac to discuss the playoff action and why he has loved watching the Phillies this fall. He also previewed the offseasons for the Cubs and White Sox. Plesac believes star center fielder Cody Bellinger is a perfect fit to remain with the Cubs.

In the final hour, Bruce Levine and Mike Esposito listened and reacted to Levine's exclusive interviews with Cubs right-hander Kyle Hendricks and White Sox right-hander Michael Kopech in which they assessed their 2023 seasons and what lies ahead. Later, the guys listened and reacted to Cubs president of baseball operations Jed Hoyer's recent comments on star Cody Bellinger's upcoming free agency, manager David Ross' work in 2023 and more.

In the first hour, Bruce Levine and Mike Esposito were joined by new White Sox assistant general manager Josh Barfield to discuss what attracted him to Chicago and the challenges that lie ahead for the organization. Later, Levine and Esposito held their Stay or Go segment in which they discussed impending free agents from the Cubs and White Sox.