Kirk has chosen sides. He is fully on Team White Sox Dave in the battle with John Cusack (00:01:30). The "Say Anything" actor and Barstool Chicago's White Sox Dave got into it over the weekend when WSD challenged Cusack for rooting for both Chicago baseball teams. Jon Gruden resigned as coach of the Oakland Raiders after old emails displaying homophobic and racist behavior is comes to light (00:05:48). Justin says goodbye to KMS over the weekend (00:27:23). Trenni is engaged after years of battling adversity for being "Boston famous" (00:35:12). Kirk outlines what it would take to get him back on WEEI (00:47:12). Tim in Canton gets to the bottom of the pizza by the slice in Iowa debate (00:58:12) & much more.

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