Way-too-early prediction for Cubs’ starting rotation at the start of the 2027 season

The Chicago Cubs' pitching staff should look very different at the start of the 2027 season. While that is mostly tied to the reality that many of the pitchers who occupied spots in the team's rotation this past year are free agents, it's also just the reality of the Cubs' needing to have a different vibe to their pitchers after consecutive years of that being the team's biggest limitation.

Jed Hoyer has also confirmed that most of the Cubs' available resources this offseason will be geared toward adding pitching, both in the rotation and bullpen. For the purpose of this exercise, we're going to put our prediction hats on and predict what the Cubs' rotation will look like on Opening Day 2027.

Here's a way-too-early look at how the Chicago Cubs' starting rotation will look next season

There's going to be some semblance of realism here. As fun as it is to dream about, we're not going to mention Tarik Skubal. Along those lines, were not going to say that the Cubs are going to trade for Logan Webb despite how perfect the fit is.

Sonny Gray

Unlike last offseason, when the biggest addition to the rotation was a trade for Edward Cabrera, the guess is that Jed Hoyer turns to the free-agent market for his big-ticket addition to the pitching staff. Enter Sonny Gray, who is fresh off posting a 2.72 ERA with the Boston Red Sox. Not to mention, his career groundball rate of 49.4% would be a tremendous fit for the Cubs' defense.

Clay Holmes

Combining the fact that the Cubs gave up one of their top prospects for Clay Holmes at the deadline, and how Jed Hoyer talked about Holmes at his end-of-season press conference, the hunch the Cubs will go out of their way to get Holmes back. His September struggles were mostly tied to command, and the larger sample size points to him being a fine No. 2 in a rotation.

David Peterson

If something worked, it wouldn't make complete sense for the Cubs to move away from it. The best trade the Cubs made in 2026 was adding David Peterson after he was booted from the New York Mets' rotation. After his move to the Cubs, he kept the ball on the ground, and posted an ERA of 3.70 in tick over 80 innings pitched. It won't be the sexiest of moves, but the Cubs should make Peterson's return a priority this offseason.

Justin Steele

While Justin Steele didn't make his return to the big-league club in 2026, he did finish the season healthy. When we last saw Steele, he was at the top of the Cubs' rotation, but it likely will be some time before he accomplishes that status once again. Steele's production in 2027 shouldn't be viewed as an expectation, but he should be capable of rounding out the rotation at the very least.

Edward Cabrera

The Cubs need Edward Cabrera to be a part of the rotation and have success. If that doesn't happen, Cabrera is going to wind up being one of the biggest whiffs of Hoyer's tenure. He finished the 2026 season in the bullpen, but he likely will be afforded a rotation spot to open 2027.

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