Waddle & Silvy

Latest Episodes:

7/1 3 PM: Colson Montgomery's standing Jul 01, 2026

Show notes

Silvy and Tyler discuss if Colson Montgomery is held in proper regard among Chicago baseball fans. Then, they run through Waddle's World and play Florida or Ohio.

7/1: The Waddle & Silvy FAFO Show Jul 01, 2026

Show notes

Tyler and Silvy kick things off on their video stream by discussing the hellish weather outside. They also discuss the visceral reaction their power rankings elicited.

6/30 4 PM: Michael Wilbon Jun 30, 2026

Show notes

Tyler and Silvy discuss another Chicago stadium saga in Tales From the Stylist's Chair before they weekly conversation with Michael Wilbon.

6/30 3 PM: Caleb Williams: QB or playmaker? Jun 30, 2026

Show notes

Tyler and Silvy discuss a quote from Mark Schlereth on where Caleb Williams stands in the NFL hierarchy. They also discuss the 50 best HBO shows in Waddle's World.

6/30 2 PM: Top 10 baseball players in Chicago Jun 30, 2026

Show notes

Tyler and Silvy break down their top 10 players in Chicago baseball right now. They also discuss the breaking news that Kawhi Leonard has been traded back to the Toronto Raptors.

6/29 4 PM: Rob Demovsky and Courtney Cronin Jun 29, 2026

Show notes

Tyler and Silvy are joined by ESPN NFL Nation's Packers insider Rob Demovsky joins Tyler and Silvy to discuss where things stand between the Bears and Packers. Then, they are joined by Bears insider Courtney Cronin to discuss this point in the Bears' offseason.

6/29 3 PM: Sox moving into playoff mode Jun 29, 2026

Show notes

Tyler and Silvy discuss the White Sox weekend that saw them take 2 of 3 from the Royals. They also break down the Blazers trade for Ja Morant and run through Waddle's World.

6/29 2 PM: Cubs scrape their way through Milwaukee Jun 29, 2026

Show notes

Tyler steps in for Waddle as he and Silvy recap the Cubs' series win over the Brewers in what could be remembered as a pivotal matchup in the 2026 season.

6/26 5 PM: Len Kasper and David Kaplan Jun 26, 2026

Show notes

Waddle and Silvy are joined by White Sox play-by-play voice Len Kasper to preview the Sox's upcoming series against the Royals and discuss what the club needs to do to build some momentum. Later, ESPN Chicago's David Kaplan checks in live from Milwaukee ahead of the Cubs' showdown with the Brewers, breaking down the NL Central matchup, the Cubs' recent surge, and what's at stake in a pivotal divisional series.

6/26 4 PM: A Tale of Two Caleb's Jun 26, 2026

Show notes

Waddle and Silvy discuss the two biggest Calebs making headlines in Chicago. The guys react to Caleb Williams' appearance on Pardon My Take and what the Bears quarterback had to say as he enters a new season. They also break down new Bulls forward Caleb Wilson's introductory after being selected fourth overall in the NBA Draft, sharing their first impressions and expectations for the franchise's newest young star.

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