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.

The National League All-Stars take down the American League in the 2025 MLB All-Star Game! Pete Crow-Armstrong made the most of his All-Star debut, flashing the glove and showing off his speed, while Kyle Tucker delivered defensively with a highlight-reel catch in left field. The CHGO Cubs crew breaks down PCA’s big night, Tucker’s impact, and what this All-Star performance means for the Cubs and beyond. Don’t miss our full recap and analysis from the Midsummer Classic!

Who are the 10 most important Cubs as the second half of the 2025 season begins? The CHGO Cubs crew breaks down which players must deliver if the Cubs want to stay in the playoff hunt after the All-Star break. From key contributors like Pete Crow-Armstrong, Kyle Tucker, and Seiya Suzuki to under-the-radar X-factors like Matthew Boyd, Daniel Palencia, and Michael Busch, we rank the players who matter most. Don’t miss this in-depth midseason breakdown packed with insight, analysis, and bold predictions!