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

The Chicago Cubs enter the second half of the 2025 season in first place — but can Pete Crow-Armstrong help lead them to a division title? The CHGO Cubs crew breaks down PCA’s impact, Kyle Tucker’s All-Star caliber play, and what the team needs to do to stay on top in a competitive NL Central. With stars like Seiya Suzuki and Nico Hoerner stepping up, the Cubs are built for a serious postseason push. Don’t miss this deep dive into the Cubs’ playoff chances and the rising roles of their biggest names.

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!

Shota Imanaga delivered a dominant performance as the Chicago Cubs took down the New York Yankees to win the series in the Bronx. Dansby Swanson & Michael Busch both crushed a home run, Pete Crow-Armstrong had a strong game, and the offense stepped up behind Imanaga’s gem. The bullpen held firm late as the Cubs closed out a big win heading into the second half. Join the CHGO Cubs crew for full postgame reaction, analysis, and what this series win means for the North Siders!

Cody Bellinger is heating up — and not in a Cubs uniform. As the Cubs face the Yankees this weekend, fans are left wondering: did Chicago make a mistake trading Bellinger? The CHGO Cubs crew breaks down his recent hot streak, how his absence is affecting the lineup, and what it means for the Cubs’ playoff push. Don’t miss this timely discussion during a crucial series in the Bronx. 

Pete Crow-Armstrong and Colin Rea powered the Chicago Cubs to a big win, helping the team avoid a sweep just before a key series against the New York Yankees. Rea was sharp on the mound, while PCA made an impact on both sides of the ball with his defense and energy. The CHGO Cubs crew breaks down the victory, what it means heading into the second half, and how the Cubs can build momentum.

The Cubs dropped Game 2 to the Twins, losing the series in Minnesota as the offense sputtered once again. Despite Cade Horton making an appearance, he struggled on the mound and couldn’t halt the Twins’ momentum. Meanwhile, Kyle Tucker, Seiya Suzuki, Pete Crow-Armstrong, and Dansby Swanson all failed to ignite the lineup. The CHGO Cubs crew breaks down Horton’s tough outing, the offense’s continued woes, and what needs to change heading into the next stretch.

The Chicago Cubs dropped the series opener to the Minnesota Twins as Shota Imanaga struggled early and couldn’t find his rhythm on the mound. The offense didn’t help, with key bats like Pete Crow-Armstrong, Kyle Tucker, and Dansby Swanson falling flat at the plate. The CHGO Cubs crew breaks down what went wrong, from Imanaga’s outing to the lineup’s lack of production. With the playoff race tightening, the Cubs need answers fast — don’t miss the full postgame analysis and reaction.

Seiya Suzuki was one of the hottest hitters in the National League—and still didn’t get the All-Star nod. On today’s CHGO Cubs Podcast, we break down the biggest Cubs All-Star snubs and debate whether Suzuki, Nico Hoerner, Shota Imanaga, and others were unfairly left off the roster. Additionally, we react to the full NL and AL All-Star selections and discuss what they mean for the Cubs moving forward. Join us as we dive into the controversy and fan reactions surrounding this year's biggest snubs.