The Chicago Cubs' recent history with the Silver Slugger award may not be as illustrious as some Cubs fans may think it would be, considering the team saw the arrivals of Kris Bryant, Anthony Rizzo, Javier Baez, and Kyle Scwarber at the Major League level, Only two member of the Cubs' World Series core won the Silver Slugger award during their time with the team, Rizzo (2016) and Baez (2018). The last Cubs player to win the award was Cody Bellinger, winning it as the National League's utility player in 2023.
In the history of the Cubs organization, their two most prominent winners are Ryne Sandberg and Sammy Sosa.