In the final hour, Chris Rongey took calls from listeners on the White Sox's moves and spending this offseason. He then had a conversation with caller "Brad in Gardner" -- who has worked at two different prisons. To end the show, Rongey shared the story of a Chicago coach who used to steal Listerine.

In the second hour, Chris Rongey welcomed on Russell Dorsey of the Sun-Times to discuss the Cubs' quest to fill out their starting rotation, the team's lack of spending this offseason and the White Sox's financial resources. After that, Rongey discussed what he called "Tom Brady fans." Later, he wondered whether the White Sox have reached their payroll threshold for the 2021 season.

Filling in for Joe Ostrowski, Chris Rongey opened his show by reacting to Texans star quarterback Deshaun Watson requesting a trade out of Houston. What does it mean for the Bears? Brad Spielberger of Pro Football Focus then joined the show to discuss the latest Watson trade rumors, the Bears' future salary cap outlook and the NFL coaching carousel. Later, Rongey discussed the news that the Cubs will watch veteran right-hander Jeff Samardzija throw in a workout soon.

In the final hour, Chuck Swirsky was joined by Eric Edholm of Yahoo Sports to discuss Northwestern football coach Pat Fitzgerald signing a contract extension to remain at the school through 2030. Later, Swirsky welcomed on longtime friend and Score football expert Hub Arkush to reminisce about their experiences in sports media and to discuss the future of the Bears' quarterback position.

In the second hour, Chuck Swirsky was joined by Bears Radio play-by-play man Jeff Joniak to discuss the latest storylines surrounding the team as it begins the offseason. Jon Greenberg of the Athletic then joined the show to discuss the complexities of modern-day sports journalism. Later, Cubs Radio color analyst Ron Coomer joined the program to discuss the team's strengths and the MLB offseason.