MLB Insider Makes Brewers-Brandon Woodruff Free Agency Prediction

The Milwaukee Brewers are one of the best teams in baseball, and they have a real shot at the World Series if they can stay hot.

Milwaukee's roster is loaded with under-the-radar talent from top to bottom. It also has a talented farm system with the perfect mix of projectable teenage prospects and MLB-ready prospects.

But the immediate future of the franchise will be figured out in the offseason. Milwaukee could turn to the trade block or free agency to upgrade its roster, but there are also some big decisions to make.

FanSided's Robert Murray recently predicted the Brewers would retain free agent pitcher Brandon Woodruff in the offseason. Woodruff is going to be the Brewers' biggest decision of the offseason.

MLB insider predicts Brewers to retain Brandon Woodruff in free agency

Aug 25, 2025; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Brandon Woodruff (53) delivers a pitch abasing the Arizona Diamondbacks in the first inning at American Family Field. Mandatory Credit: Mark Hoffman/USA Today Network via Imagn Images | Mark Hoffman/USA Today Network via Imagn Images

"If I was diabolical, I would put Woodruff with the Chicago Cubs. Alas, I will not do that. The Cubs need pitching and his long-time manager in Milwaukee, Craig Counsell, is now Chicago's manager. I wouldn’t be surprised if they had interest in Woodruff last year, but really, Woodruff was never leaving Milwaukee," Murray wrote. "Woodruff loves the Brewers. The organization loves him, everything he stands for and the leadership that he provides.

"Woodruff belongs in Milwaukee. He’ll retire with the Brewers. And I wouldn’t be surprised if he leaves money on the table to stay with the Brew Crew in the winter. Oh, and not to mention that he’s a very good right-handed pitcher who has posted a 3.32 ERA in 11 starts coming off a significant shoulder injury."

Woodruff is going to be the Brewers' biggest free agent of the offseason, and they're facing a very uphill battle to re-sign him. Woodruff has a mutual option, but he's likely going to decline it and opt for free agency.

But the Brewers will have the advantage in free agency if they're willing to offer a deal worth a similar amount of money to the other suitors. It's likely that he's looking for a multi-year deal, and the Brewers need to fork up the money to retain him.

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