*Greg Hinz, Political reporter for Crain’s Chicago Business, takes a look at all of the vacancies in City Hall and how they could be filled come election time. 

*Diallo Riddle, Emmy and WGA-nominated writer, actor, and showrunner, joins the program to talk about season three of “South Side” on HBO Max. 

*Rich Lowry from Politico explains why Trump can’t quite quit the victim act. 

*Plus, Jason Nathanson has the latest on Will Smith’s new movie, and our NFL insider has a standoff with our news anchor over the Bears versus Packers game.