The Chicago Cubs might not have a single starting pitcher heading into 2027

The Chicago Cubs are working their way towards a second straight postseason run, despite a recent rough stretch and a tightening of the NL Wild Card race.

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Although things aren’t looking quite as secure as they were maybe two weeks ago, the team is still expected to at least have a spot in the playoffs and, therefore, a chance to make some noise.

But after this season, there’s a real situation brewing—an extreme dark cloud that could keep them from a third straight postseason run.

Simply put, the Cubs aren’t guaranteed a single healthy starting pitching for their rotation in 2027.

That’s certainly a gut punch of a reality check.

The brutal reality

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First, Matthew Boyd, Shota Imanaga, Kevin Gausman, and David Peterson are all eligible for free agency at the end of this season. As of right now, there’s no inkling that the Cubs are interested in re-signing any of them to the kind of multi-year deal they’d want.

Clay Holmes, meanwhile, has a $12 million player option for 2027. Most expect him to not exercise that option and become a free agent, where he’s currently being regarded one of the top pitchers on the market below Tarik Skubal.

So, right there, that removes five starting pitching options for next season.

Emerging ace Cade Horton had Tommy John surgery this April and is expected to miss much—if not most—of 2027.

Justin Steele had his own elbow surgery last year and suffered a setback in his recovery this season. Nobody can guarantee what kind of shape he’ll be in for 2027.

Ben Brown was having a breakthrough season and had made himself the de facto ace of the rotation right up until being shut down due to his recurring neck issue. A setback in his recovery has put the rest of this season in doubt and, realistically, the rest of his career as a reliable every-fifth-day starting pitcher in doubt as well.

Edward Cabrera has been placed on the shelf on three separate occasions this season and, even when healthy, has not been anywhere near a productive member of the rotation. There’s currently talk about shifting him over to the bullpen, at least temporarily, until a path to keeping him healthy can be figured out.

Rea, Assad, Garrett as “maybe” options

Colin Rea and Javier Assad have been solid swingmen who’ve remained healthy and productive as rotation fill-ins and long-relief options. But, based on the team’s roster moves involving the two, the Cubs clearly don’t have a hefty dose of faith when it comes to giving them the ball as full-time starters.

Trade deadline acquisition Braxton Garrett is a legit wild card in the race for a 2027 rotation spot. Before undergoing the second elbow surgery of his professional career, the lefty had a promising run as a starting pitcher for the Miami Marlins. After missing all of 2025 and much of 2026, the Cubs are hoping that he begins 2027 at full strength. The operative word there, of course, is “hoping.”

For those keeping track, all of this adds up to the Cubs having precisely zero secure, high-end rotation options for the 2027 season. There will be several “maybe” and “possibly” names to keep an eye on, but that’s it.

Chicago will have a lot of money coming off the books this offseason—maybe as much as a nine-figure sum. So, there’s hope that the Cubs will swerve from their usual policy against spending big on free agent pitchers.

For now, though, things look really bad.

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