While the Chicago Cubs surely did not enjoy seeing the Milwaukee Brewers, a bitter NL Central rival, win the World Series this week, they have an opportunity to get back at their foes from Wisconsin right when free agency officially begins on Monday, November 2nd. Longtime Brewers starter Brandon Woodruff is set to be a free agent and with how badly the Cubs need pitching he’d be a perfect fit.
Chicago could potentially lose several starters in free agency. Kevin Gausman, Shota Imanaga, Clay Holmes, and Matthew Boyd will all be on the open market so that’s four starters the Cubs may potentially need to replace for next season. There are plenty of options out there, but stealing Woodruff would give the Cubs a boost and have the added benefit of annoying Brewers fans.
Woodruff is one of several Brewers free agents set to hit the market and knowing how Milwaukee likes to operate, it is likely not going to bring Woodruff back for a contract that will probably be worth somewhere in the $20 million per year neighborhood especially given his lengthy injury history.
The 33-year-old made just nine regular season starts in 2026 due to injury. He made only 12 starts in 2025, missed all of 2024 due to a shoulder injury, and made only 11 starts in 2023 so staying on the mound has been a major issue for him. Still, when he’s been on the mound he’s been really solid. Since 2021 he has a 2.79 ERA in 89 starts with 605 strikeouts in 510 innings.
Woodruff may be going into the offseason fairly healthy
On the bright side though, Woodruff was on Milwaukee’s World Series roster and got to pitch one inning during Game 3 so as long as he doesn’t have any setbacks in the offseason he should be good to go headed into 2027.
Plus, with lockout likely to delay the start of the 2027 campaign there’s a chance that will allow Woodruff more time to rest and recuperate and while the prospect of a shortened 2027 season is scary to think about, that could actually work to Woodruff’s benefit so he wouldn’t have to deal with the strain of trying to make it through a 162-game season.
Woodruff has been a Brewer his entire career and has endeared himself to Brewers fans in his time there. There’s a chance maybe he decides to take a discount to stay with the only team that he has ever known, but if the Cubs offered him a three-year, $60 million deal or something like that he’d have a hard time turning them down.
Chicago would be taking a petty big risk on a guy with a lengthy injury history, but if he could stay healthier and put up the same solid numbers he’s been putting up for years then it would absolutely kill the Brewers to see him dealing for arguably their biggest rival. Brewers reliever Trevor Megill took a shot at Chicago after clinching the title, but. now the Cubs can strike back.
Cubs Can Immediately Sour Brewers’ World Series Win When Free Agency Begins