Cubs Roundup, Sept 28: Cubs' 25 Best Individual Seasons, 40-40 Chase, & Bullpen Strategizing

[North Side Baseball]

Here is some of the latest Cubs analysis and history from around the internet. The roundup highlights Pete Crow-Armstrong's historic 2026 season, Cubs' September 28 history, Aaron Civale's potential playoff role, and his 40-40 season matching Ty Cobb's 1909 feat.

• 25 greatest individual seasons in Chicago Cubs history (Cubbies Crib). Ranks Pete Crow-Armstrong's 2026 season among the 25 greatest individual Cubs seasons, highlighting his 7.5 fWAR, 32 HR, 109 RBI, and defensive accolades, featuring legendary seasons from Cubs greats like Anthony Rizzo, Billy Williams, and Ron Santo.
• Chicago Cubs history unpacked — September 28 (Bleed Cubbie Blue). A roundup of memorable Cubs moments in history that happened on September 28, including Gabby Hartnett’s “Homer in the Gloamin’” in 1938 and Randy Myers putting his martial arts skills to use against a surprised fan who attempted to charge the field.
• Aaron Civale could be the surprising answer to the Cubs' biggest playoff question (Cubbies Crib). Aaron Civale could be the Cubs' answer to their playoff bullpen needs. He's thrived as a reliever with a 1.57 ERA and 0.5 fWAR since the trade deadline, making him a strong candidate for a high-leverage role in the playoffs.
• Cubs’ Pete Crow-Armstrong Matches 1909 Ty Cobb in Baseball History (heavy.com). Pete Crow-Armstrong matched Ty Cobb’s 1909 40-40 season with 45 homers and 41 steals, tying the league lead in homers and becoming the first player since Cobb to lead the league in homers and have 40+ steals.