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Jameson Taillon's Cubs tenure has likely come to an end

Sunday's loss may have been the last time Taillon pitches in a Cubs uniform
May 27, 2026; Pittsburgh, Pennsylvania, USA;  Pittsburgh Pirates second baseman Brandon Lowe (5) circles the bases on a three-run home run against Chicago Cubs starting pitcher Jameson Taillon (50) during the third inning at PNC Park. Charles LeClaire-Imagn Images
May 27, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Pirates second baseman Brandon Lowe (5) circles the bases on a three-run home run against Chicago Cubs starting pitcher Jameson Taillon (50) during the third inning at PNC Park. Charles LeClaire-Imagn Images | IMAGN IMAGES via Reuters Connect

The Chicago Cubs offense has been among the best in all of MLB, as they've cemented themselves as a team that wants to make a playoff run in October. However, a World Series hopeful team should at no point be punting every 5th game of the regular season, but that's exactly what is happening with Jameson Taillon.

After Taillon's last few starts, Craig Counsell was sure to finally take action, and he did after Sunday's loss in Pittsburgh, saying he would not commit to Taillon making his next scheduled start. This came after the Cubs offense nearly made an astonishing comeback after being down 7-1 through 3 innings. Taillon never really gave the Cubs a chance to win that game, and that is exactly where the problem lies.

Taillon's performance even more reason for Chicago to be aggressive at the trade deadline

With Cade Horton and Justin Steele both sidelined until 2027, the Cubs projected playoff rotation would have Ben Brown, Shota Imanaga, and Matthew Boyd pitching the first 3 games. While this isn't horrible, it's not a frontline playoff rotation that you can trust. Despite his elite start, Ben Brown has never pitched in the playoffs, and it's to be seen how he returns from his injury. Imanaga has struggled with limiting the long ball, which is not a good combination with playoff baseball.

Last season, you were able to get something out of Taillon in October, but that ship has clearly sailed, and his poor performances are even more reason for Chicago to go out and make a blockbuster move. The Cubs have been linked to Tarik Skubal, and that's the kind of move that would seriously elevate this team in October. Not only that, but you'd no longer be sending out a guy every 5th game who you have zero faith in to make a quality start.

On top of a potential blockbuster Skubal trade, the Cubs can, and should take a flyer or two on a few back-end of the rotation starting pitchers. If Jed Hoyer and the Cubs make the right moves, this team is more than capable of snatching the division away from the Milwaukee Brewers.

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