Oct 15, 2026 5:10 PM

With four starters hitting free agency, Chicago must aggressively rebuild its rotation. Pursuing superstar Tarik Skubal could solve the crisis, provided the front office outspends elite rivals.

The Chicago Cubs desperately need to address their pitching this upcoming offseason. 

The Cubs have several key starters set to hit free agency at the conclusion of the World Series. Shota Imanaga and Kevin Gausman are both free agents, while Matthew Boyd (mutual option) and Clay Holmes (player option) both have options that will likely be declined. That means Boyd and Holmes will likely head to free agency as well. 

With the Cubs losing four of five starters from this past season, they will have to be aggressive to replace those pitcher. They could easily look to re-sign some of those starters, but it looks like the writing might be on the wall for Imanaga and Gausman might want to head back to Toronto. 

Well, what better way to upgrade the pitching than to get one of the best pitchers in baseball? 

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Los Angeles Dodgers starting pitcher Tarik Skubal is set to be a free agent this upcoming offseason. Skubal, who was traded from the Detroit Tigers to the Dodgers at the deadline, will look for a big day in free agency. 

While some insiders don’t expect the Cubs to outbid other teams like the New York Mets or Dodgers for Skubal’s services, Cubs insider Patrick Mooney of The Athletic doesn’t put it past the front office to make a move for the two-time Cy Young winner. 

“The Cubs check all those boxes,” Mooney said on the recent North Side Territory podcast. “Skubal is from Arizona. His family is rooted there. He has a home base not far from the Cubs’ Mesa facility. When the entire focus is on pitching, you have to look at the best pitching out there. You have already tried to acquire him at the trade deadline. You’ve done a ton of homework on him already.”

Obviously, the Cubs are going to be one of several teams that will try to sign Skubal this offseason. Recent history suggests that the Dodgers are going to do everything they can to re-sign one of the best pitchers in baseball. 

It’s hard to imagine the Cubs going out and spending all this money on a pitcher. While he would solve a pretty big need, paying over $350 million to a pitcher doesn’t necessarily feel like something Chicago’s front office would do. 

Mooney, though, doesn’t believe that the Cubs could be counted out. They need pitching help, and Skubal would obviously solve a big pitching need. 

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