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Looking ahead to the offseason, it would seem that the biggest need the Chicago Cubs will have is for a top-of-the-rotation starting pitcher. It was a need the team avoided addressing at the MLB trade deadline, and with Justin Steele likely to miss the start of the 2026 season, it feels like avoiding the need once again won't happen.
The two names at the top of the free-agent class of starting pitchers are Framber Valdez and Dylan Cease. Despite Valdez's recent controversy with the Houston Astros, he remains on track for a lucrative long-term deal. Coupling that reality with his age, it doesn't feel like the Cubs would be involved as the top bidder.
Cease's ERA this season is out of character, 4.81, but has an expected ERA of 3.52 with a FIP of 3.67. Striking out over 30 percent of the hitters he has faced this season, Cease will have no shortage of suitors this season, and that doesn't bode well for the Cubs.
One name that the Cubs could be interested in is Milwaukee Brewers' starting pitcher Brandon Woodruff. Shoulder surgery wiped out all of Woodruff's 2024 season and a decent portion of his 2025 season. Now healthy, Woodruff has an ERA of 3.69 through his first 10 starts back and is matching Cease with a strikeout rate over 30 percent.
Woodruff is a free agent after the season, and Jon Heyman of the New York Post has the Cubs among the teams that will be a fit for the veteran starter this offseason.
MLB insider stirs buzz on Cubs stealing Brandon Woodruff from Brewers
Woodruff would check the box of the type of pitcher the Cubs usually covet in free agency. The latest example of that was Matthew Boyd, who returned late in the 2024 season before signing a two-year deal with the Cubs in the offseason.
With Boyd, Shota Imanaga, and Cade Horton forming a capable top half of a starting rotation, Woodruff would give the Cubs a dependable option at the backend to go along with Jameson Taillon. There would be a question of mapping out the potential rotation once Steele is ready, but that likely won't preclude any move the Cubs make this winter.