Ryan Dempster breaks down Cleveland vs. Chicago must-win Game 5

Name: Ryan Dempster breaks down Cleveland vs. Chicago must-win Game 5
Uploaded: 2026-10-08T14:41:24Z
Duration: 1 min 22 s
Description: World Series Champion Ryan Dempster joins the show to discuss the American League Division Series matchup between the Cleveland Guardians and Chicago White Sox, explaining why Game 5 is a daunting task but not a definitive must-win for the Sox at home.

Wake Up Barstool · FS1 · Aired Yesterday · 1m 22s

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World Series Champion Ryan Dempster joins the show to discuss the American League Division Series matchup between the Cleveland Guardians and Chicago White Sox, explaining why Game 5 is a daunting task but not a definitive must-win for the Sox at home.