The Milwaukee Brewers have one of the best teams in baseball this year, but their window to win the World Series is as open right now as it's ever going to be.
Pitchers Brandon Woodruff and Freddy Peralta aren't going to be in Milwaukee forever. Peralta is an intriguing trade candidate this offseason, whose contract expires at the end of the 2026 season. Woodruff is headed to free agency this winter and it seems unlikely that he's brought back to Milwaukee.
Bleacher Report's Kerry Miller recently called the Los Angeles Dodgers the most logical free agency fit for Woodruff. Woodruff is projected to sign for $34 million over two years, per Spotrac, which is firmly within the Dodgers' price range.
"Since the beginning of 2020, Brandon Woodruff has a 2.81 ERA," Miller wrote. "Among the 180 pitchers to log at least 350 innings across those six seasons, only Jacob deGrom (2.45) has a lower ERA. But since the beginning of 2023, Woodruff has only made 23 appearances, yet again entering this October on the IL.
"He's great when healthy, but how often will he be? 'Might make 15 starts' has become the Dodgers' sweet spot, as aside from Yoshinobu Yamamoto, their team leaders in innings pitched in 2025 were Clayton Kershaw, Dustin May and Tyler Glasnow. Even though they still have a surplus of quality options in their rotation, they could target 'Woody' as their replacement for 'Kersh.'"
The Dodgers have a lot of star pitchers on their roster, but they're struggling to stay healthy. With these injuries, they could look to go after a pitcher like Woodruff in free agency as a security blanket. Woodruff would be one of the best five pitchers in the organization when healthy and he would do it at a very affordable cost.
But if Spotrac's projection is near his actual contract, the Brewers need to do everything they can to re-sign him. Milwaukee is a pitching factory, with multiple All-Stars being developed in the minor leagues over the last few years, but the Brewers need to hold onto top talent if it's at all possible.
If Woodruff is looking at around $20 million a year for two or three years, the Brewers need to go for it and re-sign him.
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