The end of the 2026 season has been a rocky road for the Chicago Cubs. September was one of two months that saw them post sub-.500 marks on the season with an 11-13 record. They finished exactly .500 in their last 10 games. They dropped two winnable games against the Red Sox and two winnable games against the Marlins. It felt like they might be limping into the Postseason even before star third baseman Alex Bregman took a foul ball to the face, resulting in multiple fractures and multiple missed games for one of the Cubs best hitters in the second half.
Oh, you thought that was the bad news? There’s more! While that string of bad luck alone would have (probably) played the Cubs out of hosting a Wild Card Series at the Friendly Confines of Wrigley Field, Mother Nature wanted to get in on the action too. A freak September nor’easter descended upon Boston in the waning days of the 2026 season and MLB’s “solution” to this was the following itinerary for the Chicago Cubs:
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Thursday, Sept. 24: Day game at Wrigley, fly to Boston
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Friday, Sept. 25: Doubleheader in Boston, fly to Tampa
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Saturday, Sept. 26: Impromptu off day in Florida!
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Sunday, Sept. 27: Play one game in Tropicana Field to finish the season for #reasons, fly to San Diego
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Monday, Sept. 28: Workout day for the Wild Card Series
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Tuesday, Sept. 29: Begin best of three Wild Card Series in San Diego. First pitch scheduled at 10PM Eastern Time
It’s not particularly becoming in baseball to complain about certain things. After all, both teams have the same weather, the same umpires, the same roster rules and restrictions. They don’t have the same talent, but they did that to themselves and frankly, any difference in injury risk is likely a result of player decisions and tradeoffs someone made along the way as well. But this isn’t so much complaining as observing that MLB has chosen to deal the Cubs an absolutely brutal hand en route to the Postseason, which will kick off for them in San Diego tomorrow.
The question is, how will they handle it? You don’t have to look further than Bregman for answers. Bregman DH’d against the Red Sox and while it took a few at bats to get his timing back, he eventually did this [VIDEO].
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It’s obviously an incorrect inference to suggest that two swings of the bat can salvage a downturn that likely reflects a depleted bullpen pitching on fumes. That said, stranger things have happened in this season that saw the Cubs win 10 games in a row twice and lose 10 straight in another stretch. It feels like the deck is stacked against the Cubs, but this isn’t really a team that has thrown in the towel or given up at any sign of adversity this season.
This team lost Cade Horton, Justin Steele had a setback, Ben Brown emerged as a legit TOR starter before being lost for the season and they kept winning anyway. Pete Crow-Armstrong looked like he was struggling early, only to emerge as the first 40-40 man in franchise history and the likely NL MVP. Alex Bregman hitting home runs with a broken face might just be the 2026 iteration of the Cubs channeling the 2016 team’s “We Never Quit.”
There’s no such thing as an easy road to a championship. The Cubs road continues tomorrow at Petco Park, and I doubt they’ll let something as trivial as jet lag define their season.
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