MLB insider's latest Brandon Woodruff free agency prediction will enrage Brewers fans

The longest-tenured Milwaukee Brewer faces an incredibly difficult decision this offseason.

Brandon Woodruff, who joined the Brew Crew back in 2017, has been through thick and thin in Milwaukee. From making four postseason starts to enduring a lengthy rehab process to anchoring some of the best Brewers starting rotations in franchise history, Woody has meant the world to the Brewers over the last nine years. Now, more than likely, Woodruff will hit the open market this winter, leaving his future in Milwaukee in question.

It's not a guarantee that Woodruff becomes a free agent when the 2025 season comes to an end; a strange contract wrinkle exists that could keep him in a Brewers uniform for another year. Included in his contract is a $20 million mutual option for the 2026 season, meaning if the Brewers and Woodruff both believe that $20 million is a fair price for his services next year, the long-time Brewer could avoid free agency altogether this offseason. Additionally, the Brewers hold a $10 million buyout if either side rejects the option, meaning they will at least pay Woody $10 million whether he stays in Milwaukee or not.

However, what is far more likely is that Woody rejects his side of the mutual option and searches for a multi-year deal. Woodruff will turn 33 years old before the start of the 2026 season, and if he can secure a contract in the 4-5 year range that guarantees him a strong salary through the later years of his career, that's going to be hard to pass up. With his performance this season, he's proven that he can be an effective pitcher even after his major shoulder surgery, and his veteran presence and years of experience are an added bonus.

Assuming Woodruff and the Brewers don't agree on the mutual option, which is generally the case with mutual options, the question then becomes: can the Brewers compete with the rest of the league when it comes to their offer to Woodruff? While spending the last 11 years in the Brewers' organization should have a significant impact on Woody's decision, one MLB insider thinks Milwaukee's starter is destined for a big-market club.

MLB insider Jon Heyman lists Cubs, Dodgers, Mets, and Braves as potential landing spots for Brandon Woodruff

It would be hard enough to see Woodruff don the jersey of an MLB team other than the Brewers, but seeing him land with one of their NL rivals would be even more difficult to stomach. The New York Post's Jon Heyman listed three of the four teams that have eliminated the Brewers from the postseason in their last four appearances and the team's arch-rival, the Chicago Cubs, as the potential landing spots for Woodruff. Whether that's a genuine prediction or just rage bait for the Brewer faithful, the fact remains that Woodruff is going to be a popular name on the free agent market this offseason.

The Brewers will do everything in their power to retain their long-time fan favorite, and Woodruff will likely be willing to work with them to some extent in order to stay in Milwaukee, but should his price tag climb to the $100 million dollar range, which it easily could, it's going to be tough for the cash-strapped Brewers to strike a deal.

Given the fact that Frankie Montas signed a deal with an Average Annual Value (AAV) of $17 million/year at age 32 and Nathan Eovaldi commanded a three-year, $75 million deal ($25 million AAV) at age 35 this past offseason, Woodruff getting five or even six years at an AAV of at least $20 million is not out of the question. The injury history is the only thing that would prevent Woody from walking away with such a deal.

It won't be an easy offseason for Brewers fans who are now used to seeing their star players leave in free agency or as part of a blockbuster trade, but watching Woody go to one of the teams listed above would be especially difficult. Whether it's striking a team-friendly deal at the beginning of the offseason or getting creative with how they allocate the money of an eventual long-term contract, the Brewers need to exhaust every possibility before they part ways with Woody.