In season 2, episode 88, Crawly and Dustin discuss the 40-man roster moves that the Cubs made ahead of an important deadline recently and look ahead to the deadline for MLB teams to either tender contracts to players or let them enter free agency. They then discuss the latest Cubs news, including updates on the coaching staff, the Cy Young and Manager of the Year awards being handed out and the organization getting screwed out of hosting the All-Star Game in 2025. Crawly also interviews Kevin Schwartz, the owner of Schwartz Sports Memorabilia, about the Chicago Sports Spectacular in Rosemont this weekend. The Chicago Sports Spectacular is a 400-plus vendor table show selling sports memorabilia and collectables. Many former Cubs will be signing at this event.

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