9/8 5 PM: Michael Wilbon

Waddle & Silvy welcome Michael Wilbon to discuss the Bears’ stadium saga, the proposed White Sox ballpark, and the future of Chicago sports. Wilbon also reacts passionately to the controversial Michigan–Western Michigan finish and the state of college-football journalism. The show features a hilarious “In Chicago or Not in Chicago” quiz for Tom Waddle, along with a heartfelt tribute to Bears legend Matt Suhey.

Waddle & Silvy remember Bears legend Matt Suhey, discuss the importance of special teams, and examine Caleb Williams’ development heading into the 2026 season. The show also features an extended trip inside Waddle’s World, where Tom weighs in on college-football chaos, LSU’s potential SEC expulsion, Clemson’s decline, the NFL’s confusing Australia trip, Aaron Judge’s return, Shohei Ohtani’s pitching status, and some bizarre news stories.

Waddle & Silvy react to the Bears’ first depth chart of the 2026 season, including the unsettled secondary and the latest developments involving Kyler Gordon. The guys discuss Rome Odunze’s injury, Ozzy Trapilo’s recovery, Jaylon Johnson’s emergence as a “Ben guy,” and what the Bears must improve defensively. They also debate the Cubs’ fading division hopes, the White Sox’s playoff push, Jacob Misiorowski’s complaints about Wrigley Field, and Caleb Williams’ first press conference before the season opener.

Carmen joins Jesse to talk the White Sox ahead of their matchup with the Twins. We also get to what to watch for, and preview the weekend!

Taylor McGregor joins Jesse to talk week one in College Football and the Cubs. We also get to Quick Bitch!

Kevin Gausman joins Jesse on Waddle and Silvy after his night SHOVING against the Brewers. We also discuss if it's right to root for both the Sox and the Cubs!

Jesse is in for Waddle and Silvy to send you off into your holiday weekend! Jesse recaps the stars coming out to watch PCA at Wrigley last night and is joined by Barstool Big Cat!

Waddle & Silvy welcome Jeff Joniak to discuss the Bears’ expectations heading into the 2026 season. Rich shares his 10–7 prediction, praises Caleb Williams and Colston Loveland, and explains why he believes the Bears can take a major step forward. Jeff provides a practice report, including updates on Rome Odunze, D’Andre Swift, Austin Booker, and the Bears’ defensive line. The show also covers the Cubs’ fading division hopes, the White Sox’s playoff push, Jacob Misiorowski’s complaints about the Wrigley Field mound, and Munetaka Murakami’s troubling slump.

Waddle & Silvy welcome Rich Eisen to discuss the Bears’ outlook, Caleb Williams, Colston Loveland, and Rich’s 10–7 season prediction. The guys also react to Rome Odunze and D'Andre Swift leaving practice early, examine the White Sox’s playoff hopes and Luis Castillo’s struggles, and listen to highlights from Caleb Williams’ appearance on Hot Ones.