3 Chicago Cubs facing a literal 2027 make-or-break season

The Chicago Cubs finished the 2026 season with a whimper, dropping two straight in their best-of-three Wild Card series with the San Diego Padres.

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It was a disappointing end to a season that began with expectations of winning the NL Central Division and even generated some World Series talk at one point.

Now, the team is facing an uncertain offseason that will see several veteran assets potentially walk away via free agency. They are also looking at a pitching staff that needs a full restocking and a quick, successful rebuild if they want to win within their current window of opportunity.

Between potential free agent acquisitions and other roster maneuverings, the Cubs must also account for players who are out of minor league options and must either make the 26-man roster out of Spring Training or be lost.

Chicago has three of those use-or-lose players standing on deck coming into the 2027 season.

Use or lose: Kevin Alcantara, Jordan Wicks

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Outfielder Kevin Alcantara is young and still developing, but he’s reached the point where he’s out of options and is potentially facing the end of his run with the Cubs.

The 24-year-old crushed the ball at Triple-A Iowa this past season and plays plus defense at all three outfield spots, but he also showcased some of his weaknesses as a hitter with a whole lot of swings and misses. In the majors, the offensive holes in his game have been especially glaring, accounting for 11 strikeouts in just 24 plate appearances in 2026.

The thought is that Alcantara will make the big league squad out of absolute necessity as outfielders Seiya Suzuki, Ian Happ, Michael Conforto, and Tyrone Taylor could all be lost to free agency. He’s also likely to get a long leash because of that need.

But the Cubs really can’t do anything with him, other than keep him arounf and hope for the best. Not making the Opening Day roster or being demoted from the roster during the season would force him on to the waiver wire, where another team would surely claim him.

Pitcher Jordan Wicks is in the same situation as Alcantara.

Chicago’s No. 1 draft pick in 2021 has had several cups of coffee in the majors, but he’s never been able to stick. He’s now out of options. If he can’t make the big league roster and can’t stay there, he’ll be gone.

The lefty will be given every opportunity to contribute to the major league Cubs. The team desperately needs pitching, especially the innings a starter can contribute. With the team’s entire end-of-season starting rotation becoming free agency-eligible, as well as a good chunk of their bullpen, there will be plenty of opportunity to stick around. If he can’t cut it, it’s waiver time and good-bye time.

The Braxton Garrett gamble

Another pitcher facing a Cubs make-or-break 2027 is Braxton Garrett.

The 29-year-old lefty was acquired from the Miami Marlins at this year’s trade deadline at a cost of well-regarded first base prospect Jonathon Long and pitching prospect Jace Beck.

Unlike Wicks, Garrett has had sustained big league success—in 2023 he started 30 games and posted a 3.66 ERA. Elbow surgery in late 2024 cost him the entire 2025 season and much of the 2026 season. He’s expected to be ready to go by the spring of 2027 and he’ll definitely get his chance to win a spot in the starting rotation. If he doesn’t, though, he’ll also likely be an ex-Cub.

Chicago could move to trade Alcantara, Wicks, and Garrett this offseason and at least secure something for them. But given the team’s current roster needs, it’s more probable that they’ll keep these players around to the very end.

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Source: https://www.chicitysports.com/chicago-cubs-facing-a-literal-2027-make-or-break-season-garrett-wicks-alcantara/