The Pitcher The Cubs Need To Sign This Offseason

The Chicago Cubs will need to acquire pitching this offseason. 

The Cubs are set to lose four key starters to free agency. Shota Imanaga and Kevin Gausman will be free agents, and Matthew Boyd (mutual option) and Clay Holmes (player option) will likely be free agents since neither pitcher will likely exercise their options. 

Now the Cubs could look to re-sign a few of those pitchers. They desperately need pitching help, and the team already knows all four of them. Imanaga, Gausman, Boyd, and Holmes also showed some nice things throughout the year. 

However, there are reports circulating that the writing may be on the wall for Imanaga, and Gausman could head back to Toronto to finish his career. It’s unclear whether Boyd and Holmes will return or whether either would welcome it. 

Either way, the Cubs need to acquire a few starting pitchers this winter. They need a true No. 1 pitcher and someone who can step up when the team needs it most. Chicago didn’t have that pitcher this past season. Boyd allowed four runs across four innings in Game 1 of the National Wild Card Round, and Gausman allowed three runs across 3 ⅓ innings in Game 2. 

Tarik Skubal should obviously be at the top of the Cubs’ wish list. The two-time Cy Young winner is exactly the type of pitcher that this team needs. He’s one of the best pitchers in baseball and would solve that need for a true No. 1 

Realistically, it’s hard to imagine the Cubs spending big money on a pitcher of Skubal’s caliber. The front office would have to dish out over $300 million, and that just doesn’t seem like something Tom Ricketts would be willing to do. 

Instead, the Cubs should pivot to acquire another pitcher who has shown to be a true No. 1. 

Michael King should be at the top of the Cubs’ free agent target list. The Padres starter could decline his player option for the 2027 season, making him a potentially coveted free agent this offseason. 

King is coming off a strong 2026 campaign in which he finished with a 3.21 ERA and 159 strikeouts over 185 innings pitched. The veteran right-hander also threw seven shutout innings with eight strikeouts against the Cubs in Game 1 of the NLWC. 

The Cubs desperately need top-of-the-line starting pitching this offseason. King would certainly upgrade this rotation and would be that No. 1 ace that the team was looking for this past season.