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After a tumultuous departure from the Cardinals, Caray joined the Oakland Athletics, where he struggled with the team’s management but built a loyal following. His next move took him to the Chicago White Sox, where he thrived during a challenging period for the team. Caray's knack for publicity was key, as he secured bonuses based on attendance, helping to draw fans to the ballpark.
Caray's career reached new heights when he began announcing for the Chicago Cubs. His association with WGN, a superstation, catapulted him to nationwide fame. Fans were drawn to his exuberance, unfiltered opinions, and the memorable tradition of leading the crowd in a rendition of "Take Me Out to the Ball Game" during games.