In the second hour, Bruce Levine and Matt Spiegel were joined by White Sox general manager Rick Hahn to discuss the team's offseason plans, the upcoming Winter Meetings, the outlook for the 2020 season and more. Later, the guys continued to discuss the White Sox by reacting to a rumor that outfielder Marcell Ozuna is interested in signing with them.

Bruce Levine and Matt Spiegel opened their show by previewing the Winter Meetings and discussing the latest Hot Stove news and rumors as they pertain to the Cubs and White Sox. Later, former Cubs reliever and current free agent Steve Cishek joined the show to discuss his future.

In a shortened second hour, Bruce Levine and Mike Esposito were joined by Cubs Radio play-by-play man Pat Hughes to discuss the latest storylines in the MLB offseason and broadcaster Bob Costas.

Bruce Levine and Mike Esposito opened their show discussing the latest Cubs and White Sox storylines as the start of the Winter Meetings loom in just more than a week. What big decisions will each team have to make? Later, Jim Bowden of MLB Network Radio and the Athletic joined the show to discuss the latest Cubs, White Sox and MLB storylines.

In the second hour, Bruce Levine and Matt Spiegel were joined by analyst Ryan Dempster to discuss the approach the Cubs will have this offseason, whom they may trade and the impact that new manager David Ross will have on the team. Dempster also shared strong thoughts on the Astros' signing-stealing scandal, which the guys later continued to discuss at length.