In his second hour, Joe Ostrowski was joined by Capital Bureau chief Mark Maxwell to discuss the issues the state has encountered with the legalization of gambling. Later, Ostrowski explained the ins and outs of how mobile gambling will work in Illinois.

Joe Ostrowski opened his show by wondering where the Cubs will finish in the NL Central this season and which teams they're better than in the division. Later, Ostrowski questioned what the Cubs will do with the Marquee Sports Network with the start of the season just around the corner.

In the final hour, Joe Ostrowski replayed White Sox right-hander Michael Kopech's interview on the McNeil & Parkins Show earlier in the day in which he eloquently detailed his mental health struggles and what he has done to address them. Later, the crew discussed who's the most likable Chicago athlete.

In the third hour, Joe Ostrowski discussed the Bulls' struggles and how the season hasn't gone as planned for them. More and more people seems to be laughing at the Bulls if they're not indifferent about them. What will bring change for the organization? Later, Ostrowski played back some of the White Sox television analyst Steve Stone's interview on the Mully & Haugh Show earlier in the day. Stone expressed plenty of excitement for the season.

In the second hour, Joe Ostrowski was joined by Josh Nelson of the Sox Machine podcast to discuss a variety of White Sox topics ahead of SoxFest this weekend. The guys broke down the team's strengths and weaknesses, discussed how excited fans should be and shared expectations for the 2020 season.

Joe Ostrowski opened his show by discussing the Cubs' impending launch of their Marquee Sports Network, which will broadcast all of their local games. Marquee hasn't yet reached a deal with Comcast, which provides cable for more than half of Chicago. Is there going to be a deal done in time for the 2020 season? Later, Bryan Perez of NBC Sports Chicago joined the show to provide insight on some of the players whom the Bears could and should target in the NFL Draft.

In the final hour, Joe Ostrowski reflected on the biggest storylines out of Cubs Convention over the weekend. He then took calls from listeners on what they thought of Cubs owner Tom Ricketts getting booed when he brought up the team's new Marquee Sports Network. Later, Ostrowski welcomed in Julie DiCaro for transition.

In the second hour, Joe Ostrowski discussed the Chiefs-49ers matchup in the Super Bowl and which team he believes has the edge. Ryan Hovart of of 105.7 The Fan in Milwaukee then joined the show to discuss the Packers' loss to the 49ers in the NFC Championship Game and if Green Bay will experience regression in 2021. Later, Bryan Perez of NBC Sports Chicago joined the program live from the Senior Bowl in Mobile, Alabama. He discussed whom the Bears could be eyeing in the NFL Draft.

Joe Ostrowski opened his show by reacting to the news of Derek Jeter and Larry Walker being elected into the Baseball Hall of Fame. Ostrowski also looked at the voting results for other players on the ballot, including those with ties to the Cubs and White Sox.

In the final hour, Joe Ostrowski discussed Bears legend Devin Hester's credentials for the Pro Football Hall of Fame. Will he be the next former Bear to enter the Hall of Fame? If not him, who will be next? Ostrowski also welcomed in Julie DiCaro for transition, where they discussed the most recent developments in the MLB cheating scandals and what new shows are worth watching.