After nearly 45 years, the Milwaukee Brewers finally returned to the World Series and earned their first championship.
The Brewers have been a dominant team for years, winning 90 or more games in each of the past four seasons, but they took it to a new level this year. Milwaukee won a franchise-record 103 regular-season games and went 11-2 in its World Series run. Now that celebrations are over, however, it's time to look ahead to how the team can maintain its dominance heading into next season.
Milwaukee has four notable free agents who have officially entered free agency following its World Series run, including Brandon Woodruff , Dustin May , JoJo Romero and Jake Bauers . May and Romero joined the Brewers in a trade deadline deal this year, while Bauers and Woodruff have been with the team for years. Heading into free agency, Milwaukee should focus on bringing back Woodruff on a discounted contract and letting May walk.
Oct 26, 2026; St. Petersburg, Florida, USA; Milwaukee Brewers first baseman Jake Bauers (9) reacts after striking out against the Tampa Bay Rays during the first inning in game three of the 2026 World Series at Tropicana Field. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | IMAGN IMAGES via Reuters Connect
May is a fine starter, but he failed to live up to the Brewers' expectations when trading for him. Despite being a four-time World Series champion, the 29-year-old pitcher didn't serve as the No. 3 pitching option Milwaukee had hoped for. May struggled after being dealt to the Brewers, posting 5.65 ERA with 38 strikeouts across 10 starts.
May spent the first five and a half seasons of his career with the Los Angeles Dodgers but has bounced between teams over the last couple of years. Though he boasts a 4.12 career ERA, if the Brewers couldn't trust May this postseason, why would they bring him back?
Woodruff, on the other hand, has been a consistent rotation piece for Milwaukee for years. The nine-year veteran has spent his entire career with the Brewers, and though he's struggled with injuries, he's still been great when healthy. The 33-year-old hurler posted a 2.98 ERA through nine starts this season, and returned from injury just in time to appear in the World Series, where he allowed one run on two hits in one inning against the Tampa Bay Rays.
The Brewers had Woodruff on a one-year, $22 million contract after he accepted a qualifying offer last year, but retaining him this offseason would likely not be that expensive. Spotrac projects the two-time All-Star will command a contract around $11 million, a big discount compared to what Milwaukee spent this season.
Woodruff's a fan favorite, and despite an extensive injury history, which has limited him in each of the past four seasons, he still boasts a career 3.10 ERA. If the Brewers can bring him back on a more team-friendly contract this offseason, they should. It will be interesting to see how Milwaukee tackles the offseason after winning it all.
This article was originally published on www.si.com/mlb/brewers/onsi as One Brewers Free Agent They Can't Afford to Lose and One They Can .
