Top 10 Biggest “What Ifs” in Chicago Cubs History! | CHGO Cubs Podcast

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Recorded17 Jul 2025

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What if the Cubs never traded Kris Bryant or Anthony Rizzo? What if Sammy Sosa stayed a Cub — or Alex Gonzalez made the play in 2003? In this episode of the CHGO Cubs Podcast, we rank the Top 10 biggest “What Ifs” in Chicago Cubs history — from the collapse of the 1969 Cubs to moments that nearly derailed (or could've extended) the 2016 championship run. These are the franchise-altering twists that could have changed everything at Wrigley Field. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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