Cubs' offseason pitching overhaul has 1 dream target, 1 realistic option and 1 costly mistake

Given how the Chicago Cubs have operated in recent years, it might be embedded into the mind of Chicago Cubs fans to feel like the team stands no chance at signing Tarik Skubal. Sure, the Los Angeles Dodgers and New York Mets are going to be viewed as the favorites for Skubal, but shouldn't the Cubs have a seat at the table?

They should. Hand up, I have been guilty of not really including Skubal in think pieces about what the Cubs should do this offseason. Again, this is a Cubs team that went out of their way to confirm they would have no interest in Juan Soto or Corbin Burnes during their respective free agencies. This is also a Cubs team that bowed out of the bidding for Dylan Cease last offseason once it passed $200 million.

1 dream target, 1 realistic target, 1 mistake Cubs could make in their search for pitching offseason

Why bother with mentioning the Cubs as a dream fit for Skubal? Well, we should because the Cubs need to be challenged in this regard. Spending currently appears to be the only advantage the Cubs will haver over the Milwaukee Brewers moving forward and what better way to prove that than by signing Skubal? That is where we shall begin.

Tarik Skubal, dream target

Skubal is the dream target for the Cubs and that is always going to be the case until he signs elsewhere. It's certainly possible that the Dodgers aren't in a position to sign Skubal BEFORE the lockout, and that could create an opening for another team to swoop in before then. With over $100 million coming off their books this offseason, and clean books moving forward, the Cubs can easily fit in a contract for Skubal without worrying about the potential implication that would have under revamped payroll rules.

Sonny Gray, realistic target

Sonny Gray may not have had the impression strikeout numbers with the Boston Red Sox in 2026, but he had just about everything else. He's a finalist for the the most outstanding pitcher award for the American League league, and that speaks to just how good he was last year. He's also a pitcher the Cubs have been connected to throughout the past decade, and this could be an instance where Jed Hoyer finally gets his guy. Unlike Kevin Gausman at the deadline, Gray's 2.70 ERA and 46% ground-ball rate suggest he still has something left in the tank.

Casey Mize, costly mistake

Casey Mize has the feel of a pitcher who is going to be overpaid this offseason. Assessing his market value, spotrac had his next contract valued over $100 million for six years. No team should be willing to make that deal. Mize has flashed potential, but he's also struggled to stay healthy. His free agency has buyer's remorse all over it, and it's hard to ignore the 7.46 ERA he had with the Padres over his last 10 starts that also featured his fastball velocity on the decline.

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