Skip to main content

Cubs should keep tabs on Brandon Woodruff after Brewers World Series roster gamble

Cubs can't afford to leave any stone unturned this offseason
ByRich Eberwein
2026 World Series workout day and media availability
2026 World Series workout day and media availability | Aaron Gash/GettyImages

With the Chicago Cubs looking to bolster their pitching staff any way they can this offseason, Milwaukee Brewers righty Brandon Woodruff is a name that should be on their radar. After going down with shoulder inflammation in July, Woodruff made a surprisingly quick recovery and was added to the Brewers' World Series roster on Friday.

In July, the 33 year old initially told the media that he would need season-ending shoulder surgery, which would have been his second shoulder procedure in the last three years. But Woodruff was able to avoid that when imaging found his shoulder had healed more than expected. Now, he's in a position to help the team that drafted him back in 2014 win its first World Series title.

A surprise add to the Brewers' World Series roster, Brandon Woodruff could be a future Cubs target.

The World Series could give Woodruff the chance to show teams that he is healthy enough to sign a new contract when he hits free agency next month. Although he's the longest-tenured Brewer and hasn't pitched for another team in his career, Milwaukee is not keen on re-signing guys once they hit free agency because of their tight operating budget.

This is where the Cubs — a team with a much more lenient budget and money to play with this offseason — could swoop in with a contract offer. Don't get me wrong, we need to see how Woodruff looks first because this would be a risky play. Woodruff's shoulder issues have limited him to just 32 starts over the last four seasons, and he missed the entirety of the 2024 campaign after his last surgery. Plus, he needs to get through the World Series unscathed.

While the shoulder has been a concern for a while, Woodruff pitches at an extremely high level when he is healthy. His career 3.10 ERA and 29.1% strikeout rate are stellar marks that the Cubs would love to incorporate into their pitching staff. Woodruff also has a rapport with Cubs manager Craig Counsell, who coached Woodruff for seven years.

Woodruff's return adds an interesting wrinkle to this year's World Series, and the Cubs would be wise to consider anyone they can to replace their soon-to-be-barren pitching staff.

Add us as a preferred source on Google