Joe Ostrowski opened his show by going in-depth on the Bears' overtime loss to the Saints on Sunday. Are the Bears truly finding themselves in real trouble? Should they consider going back to Mitchell Trubisky at quarterback? Later, with election night in full swing, Ostrowski posed this question to listeners: If you were to elect one player to stay from each of the major Chicago sports teams for the next four years, whom would you choose?

In the final hour, Zach Zaidman was joined by Kevin Fishbain of the Athletic to preview the Bears-Saints game Sunday. Later, Zaidman took calls from Score listeners to get their reactions to the White Sox's hiring of Tony La Russa as their new manager, the expectations for the Bears against the Saints and more.

In the second hour, Zach Zaidman was joined by Score baseball insider Bruce Levine to discuss the Cubs' decision to decline left-hander Jon Lester's $25-million option for 2021 and more. Former Bears offensive lineman Jermon Bushrod then joined the show to reflect on his NFL career and to discuss how Chicago's offensive line can improve against the New Orleans Saints on Sunday. Later, Fox 32 television host and analyst Lou Canellis joined the program to discuss the latest Bears storylines and the White Sox's hiring of Tony La Russa as their new manager.

Zach Zaidman opened his show with a rundown of the latest Chicago sports stories. ESPN play-by-play commentator Jon "Boog" Sciambi then joined the show to discuss the Cubs' decision to decline left-hander Jon Lester's $25-million option for the 2021 season and what to make of Rays manager Kevin Cash pulling ace Blake Snell when he was rolling in the sixth inning of the decisive Game 6 of the World Series that the Dodgers rallied to win. Later, WBBM analyst Jay Hilgenberg joined the program to preview the Bears-Saints game Sunday.

In the second hour, Joe Ostrowski discussed the Bears' inability to find an offensive identity behind quarterback Nick Foles and how they're preparing for the Saints on Sunday. Ostrowski then replayed a segment on his Bet Sweats show on Radio.com Sports in which guest Dan Back told the story of a daily fantasy sports player who lost $997,000 because of a rather meaningless statistical correction in the Bears' loss to the Rams on Monday night. To close, Ostrowski listened back to the best of White Sox ace Lucas Giolito's interview on the Danny Parkins Show earlier in the day.