9/8 5 PM: Michael Wilbon

Waddle & Silvy break down the Cubs’ devastating bullpen collapse against the Brewers with Jesse Rogers, who explains why Jacob Webb has struggled, whether the front office deserves blame, and how Milwaukee’s culture and player development continue to separate the teams. They also discuss Munetaka Murakami’s slump and the White Sox’s chances of holding onto first place. Tyler Aki makes his NFL playoff and Super Bowl predictions, while Waddle reveals Garrett Bradbury as No. 4 on his list of the Bears’ most important players.

Waddle & Silvy open with the start of football season, breaking down the Bears’ injury report, Tyson Bagent’s back issue, Rome Odunze’s absence, and the excitement surrounding the team’s young talent. They take calls on Colston Loveland, rookie defensive tackle Alex Vandenberg, Munetaka Murakami’s swing, and the ongoing Kyler Gordon situation. The show also features the annual NFL wins pool, as Waddle, Silvy, Charlie, and Tyler draft their teams and debate which clubs will pile up the most victories. Plus, Eddie Olczyk discusses the Cubs, Patrick Kane’s return to Chicago, cancer awareness, and the loss of Bears legend Matt Suhey.

Waddle & Silvy welcome Barstool Big Cat to discuss the Cubs’ bullpen collapse, the Brewers’ continued dominance, and whether Chicago can still make a postseason run. They also break down college football controversy involving Wisconsin, Michigan, and Lane Kiffin before turning to the Bears’ expectations, Tyson Bagent’s injury, Rome Odunze’s calf issue, and the possibility that 2026 is the “year before the year” for Caleb Williams and Ben Johnson’s offense.

Waddle & Silvy examine the Cubs’ dramatic collapse against Milwaukee and debate why the Brewers have been 24 games better over the last three seasons. The guys discuss Jacob Webb’s historic run of blown saves, whether the Cubs’ roster is better suited for the postseason, and the growing anxiety surrounding the White Sox. They also break down Munetaka Murakami’s prolonged slump, debate how the Sox should handle his future, and preview the Bears’ upcoming season.

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!