Gambling for Shoes

Jack digs deep for a new gambling strategy, then dusts off his political science degree to spread misinformation.

12 Nov 202220min

Jack finally hits some NFL paydirt, tip-toes arond Kanye and Kyrie, and meets his first Chicago foe.

4 Nov 202226min

Jack weeps over a horrific week 7, gets mad at Dusty Baker's hands, and is suddenly optomistic about social media.

27 Okt 202227min

Jack's making NFL guarantees then relives some baseball glory and reviews about a week of stand-up.

22 Okt 202219min

Jack picks his favorite NFL teams to gamble on and favorite stand-up comics to watch in this circular reasoning extraordinaire!

14 Okt 202225min

After a week in gambling jail, Jack returns to prove he's a changed man and ready to make smart picks.

7 Okt 202221min

Jack licks his wounds after a brutal week 2, compares Chicago to Venezuela, and attempts to get vulnerable about comedy. Plus fooh-ball!

23 Sep 202225min

Jack toasts himself over a Week 1 victory, denounces sneakerhead culture, and tells his first Chicago train story. Plus shoes!

15 Sep 202227min