One Starting Pitcher the Cubs Should Definitely Bring Back for 2027

It’s a very busy time for the Chicago Cubs. Free agency has begun, and the General Manager meetings are underway in Las Vegas. Plenty of moves are expected soon, and time is of the essence as a lockout looms. Will the Cubs make something happen?

If one thing is for sure, they have to add to their roster if they want to improve. After being eliminated in the Wild Card by the San Diego Padres, you would think they would focus on top-of-the-line talent in free agency. Sure, signing big-name free agents doesn’t guarantee success, but the Cubs have the money to spend and positions to fill.

However, it sounds as if that will not be the Cubs' focus. According to The Athletic, Sahadev Sharma, it is all but confirmed that they are not planning to go after Tarik Skubal. Instead, they will focus on other routes, including trades and re-signing players on expiring contracts.

Who Should the Cubs Re-Sign this Winter?

A long list of Chicago Cubs players have become free agents, including a handful of starting pitchers. With no big-splash signings expected, can the Cubs re-sign any of their guys to return and stabilize the rotation? That may be how they have to approach it.

Shota Imanaga, Matthew Boyd, Clay Holmes, Kevin Gausman, and David Peterson are among the former 2026 Cubs hitting free agency. Imanaga has had his fair share of struggles, and the Cubs have shown they don't trust him when it matters most. Gausman was an impactful trade acquisition, but he is widely expected to go back to the Toronto Blue Jays. Finally, you have Holmes and Boyd. They both declined their player options to enter the open market.

It’s a tough decision, but the Cubs' best bet would likely be to re-sign Clay Holmes. They traded a top prospect, Jefferson Rojas, to acquire him, and he proved to be a valuable addition to the rotation when the Cubs were desperate to add guys due to injuries. Although he’s not an ace or top-of-the-rotation starter, Holmes provides stability, veteran leadership, and top-tier groundball production.

If the Cubs were to re-sign Holmes, he could be the fourth or fifth option in a revamped rotation. In 2026, he went 6-8, struck out 78, walked 42 batters, and posted a 3.29 ERA. The traditional stats don’t fully justify what he is capable of, particularly when we consider his fit in front of this elite Cubs defense. Last season, Holmes had a 60.8 percent groundball rate, ranking inside the league's 99th percentile.

Indeed, Holmes was the glue that held the rotation together when they needed it most. Bringing him back won’t solve all of their woes, but there is no question that the fit makes a lot of sense for this win-now Cubs team.

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