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Both players reached the top of their sport in Chicago. Derrick Rose became the youngest MVP in NBA history and looked ready to lead the Bulls back to championship glory before devastating injuries changed the trajectory of his career. Kris Bryant helped break the Cubs’ 108-year World Series drought, won NL MVP, and was on a Hall of Fame pace before injuries and roster changes reshaped his future. So which career leaves fans wondering more? What if D-Rose never tears his ACL? What if Bryant stays healthy and remains the face of the Cubs dynasty? How many championships are we talking about? How different does Chicago sports history look?
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"Derrick Rose or Kris Bryant? Which Chicago Star Has the Bigger “What If?”" is an episode of CHGO Chicago Cubs Podcast. Runtime 7 min. Published February 13, 2026. Hit play above to stream it here, or open the free Spot Sports app for background play and offline downloads.