In the second hour, Joe Ostrowski was joined by Sahadev Sharma of the Athletic to discuss the Cubs' managerial search, what lies ahead in their offseason, their missed opportunity to create a dynasty, trade possibilities among their core four players, MLB free agency and more.

Joe Ostrowski opened his show discussing the expected return of Bears quarterback Mitchell Trubisky from a left shoulder injury this Sunday. Ostrowski asked listeners for their thoughts on Trubisky and how the Bears will do against a banged-up Saints squad.

WIP evening radio host Joe Giglio joined Joe to talk about what went wrong in Philadelphia for Gabe Kapler and would he make a good candidate for the Cubs manager opening.

In the third hour, Joe Ostrowski was joined by former Score producer and current 95.3 Tampa Bay program director John "Rock" Mamola to reminisce about old times at The Score and discuss the XFL, Jameis Winston and the Buccaneers and a splash of White Sox.

In the second hour, Joe Ostrowski was joined by Dan Durkin of the Athletic to discuss what he has saw on tape from Bears quarterback Mitchell Trubisky before he was injured. Durkin also discussed the evaluation process for NFL quarterbacks. Later, Ostrowski asked whether you'd rather be the Cubs or Cardinals this season. The Cubs didn't make the playoffs, but the Cardinals were in the process of bowing out in embarrassing fashion against the Nationals in the NLCS.

Joe Ostrowski opened his show reacting to the Packers' 23-22 win against the Lions on Monday night, which got him wondering this: Who's the worst team in the NFC North? He asked listeners for their thoughts as well.

In the final hour, Joe Ostrowski was joined by Dave Sharapan of CG Technology to discuss his favorite plays in the NFL this weekend. Later, 670 executive producer and hockey expert Jay Zawaski joined the show to discuss the Blackhawks' loss to the Flyers in their season opener in Prague on Friday afternoon and what he liked and disliked in Chicago's performance.

In the third hour, Joe Ostrowski was joined by former Bears receiver Earl Bennett to discuss his new podcast venture, his playing days with the organization and what he thinks of the current team. Bennett compared the Bears' quarterback situation to the one he endured with Jay Cutler and Josh McCown in his time with the team and explained why he believes Chase Daniel is a better fit than Mitchell Trubisky for coach Matt Nagy's system.

In the second hour, Joe Ostrowski was joined by Las Vegas radio host and former Raiders pregame and post host Adam Candee to preview the matchup between Chicago and Oakland on Sunday. Candee also broke down why coach Jon Gruden and the Raiders traded star edge rusher Khalil Mack to the Bears in 2018 and if Oakland fans miss Mack.

Joe Ostrowski opened his show discussing the feeling around the NFL that teams should know if they have a franchise quarterback by the third year of that player's career and how it pertains to the Bears' Mitchell Trubisky, on whom the verdict isn't good so far. Ostrowski discussed where Trubisky struggles and what the Bears' other options might be moving forward. He also listened in to some sound from Robert Mays of the Ringer on the Bernstein & McKnight Show explaining why Trubisky isn't a franchise quarterback.