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What Should the Cubs Regret Most About 2026? Wasting Pete Crow-Armstrong's Heroics

The biggest regret for the Cubs cost them a historic season.
Sep 18, 2026; Cincinnati, Ohio, USA;  Chicago Cubs outfielder Pete Crow-Armstrong (4) waits on deck to bat against the Cincinnati Reds in the second inning at Great American Ball Park. Mandatory Credit: Aaron Doster-Imagn Images
Sep 18, 2026; Cincinnati, Ohio, USA; Chicago Cubs outfielder Pete Crow-Armstrong (4) waits on deck to bat against the Cincinnati Reds in the second inning at Great American Ball Park. Mandatory Credit: Aaron Doster-Imagn Images | IMAGN IMAGES via Reuters Connect

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The National League Championship Series is in full swing. The Milwaukee Brewers lead the series 2-0 against the Los Angeles Dodgers, and both teams are talented and deep. They are showing the league why they belong, with star talent throughout. The Chicago Cubs had the same aspirations, and it makes fans wonder whether they should have been there instead.

It was a wasted opportunity. What was once a magical season turned into instant regret. Numerous mistakes cost the Cubs a chance at glory. What caused it? Pitching, injuries, and coaching all played a role. All the Cubs can do now is sit back and think about what could have been.

The season was on the verge of being something special. The Cubs scored a total of 850 runs, which ranked first in the league. They led in numerous offensive categories and had a top-tier defense. On top of it all, they got an MVP-caliber season from a young superstar. Pete Crow-Armstrong's magical season at the plate will earn him a special place in Chicago’s heart, but it came at what cost? 

Pete Crow-Armstrong Deserved Better

Pete Crow-Armstrong
Sep 25, 2026; Boston, Massachusetts, USA; Chicago Cubs center fielder Pete Crow-Armstrong (4) at bat against the Boston Red Sox during the first inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images | IMAGN IMAGES via Reuters Connect

Pete Crow-Armstrong will be the National League MVP for the 2026 season. His 40-40 season was something special. He was the first to accomplish this in Cubs history, hitting 45 homers with 40 stolen bags. The stat line is rare; only seven players in MLB history have done it.

Simply put, the Cubs wasted his season, and he is unlikely to get another chance to repeat it. It’s not a knock against Crow-Armstrong. He’ll be a stellar player for years to come. He could win multiple MVP awards and make multiple All-Star appearances. If the Cubs wanted to take full advantage of his play, however, this would have been the perfect time to do so. 

It’s honestly what the Cubs should regret most from the 2026 season. President of Baseball Operations Jed Hoyer built a strong team and found a young superstar to build around. However, Hoyer is also responsible for failing to build the kind of deep rotation and bullpen to ensure Crow-Armstrong's efforts didn't go to waste.

Crow-Armstrong did everything he could to carry the Cubs. To be sure, he struggled in the postseason. He went hitless in seven plate appearances and had only one stolen base. It was nowhere near the version of Crow-Armstrong fans grew used to. It also didn’t help that he faced the likes of Michael King. Still, if anyone earned the benefit of the doubt, it was Crow-Armstrong. And the fact that he didn't get more of an opportunity to make some noise stings.

If the Cubs do not want any future regrets, they need to improve the team around Crow-Armstrong this offseason. He is the rare kind of player who can help drag a team into postseason contention year in and year out. It's the front office's job to support him with the kind of talent that makes such efforts worth it.

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Doug Schwamb
DOUG SCHWAMB

Doug Schwamb has written for sports blogs on FanSided, including Da Windy City and Pippen Ain’t Easy. He graduated with a degree in Journalism from Marquette University, where he wrote for the Marquette Wire Newspaper and covered the men's golf team. Schwamb loves to travel, and his goal is to visit all 30 MLB stadiums with his dad. They're at seven total!

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