Should Brewers Let Two-Time All-Star Pitcher Walk In Free Agency?

The Milwaukee Brewers have an important decision to make on one of their longest-tenured players this offseason.

Apr 22, 2026; Detroit, Michigan, USA; Milwaukee Brewers right fielder Sal Frelick (10) glove and hat sit on the Brewers dugout steps covered in infield dirt during their game against the Detroit Tigers at Comerica Park. Mandatory Credit: Lon Horwedel-Imagn Images | IMAGN IMAGES via Reuters Connect

The Milwaukee Brewers boast the best record in baseball, backed by one of the most intimidating pitching staffs in the league.

The Brewers appear to be on track to win their fourth division title in a row, or at the very least, reach the playoffs for the eighth time in the past nine seasons, and their pitching has played a major role in their success this year. Milwaukee's pitching staff has the second-best ERA in the league at 3.47, and the starting rotation specifically has a 3.46 ERA, which ranks third among teams.

Jacob Misiorowski's ascent to one of the best pitchers in baseball has definitely been a big part of the Brewers' success. But the rest of the rotation has been solid as well, despite lacking consistency, as no other pitcher has thrown 100 innings besides the superstar fireballer. Bolstering the thin starting rotation was one of Milwaukee's biggest trade-deadline needs, so the team brought in Dustin May to round out the rotation and also added relievers JoJo Romero and Antonio Senzatela.

With most of their rotation locked down after this season, the Brewers will have to decide what they want to do with two-time All-Star hurler Brandon Woodruff, as MLB.com's Theo DeRosa, Manny Randhawa and Shanthi Sepe-Chepuru called the 33-year-old the team's "biggest impending" free agent.

"Woodruff announced in mid-July that he would need a second surgery on his right shoulder, which knocked the right-hander out for the rest of 2026 and potentially beyond," DeRosa, Randhawa and Sepe-Chepuru wrote on Sunday. "Woodruff said he isn’t ready to call it a career, but the two-time All-Star, a pending free agent, might not be back with the Brewers in 2027. After a delayed start to the season, Woodruff had a 2.98 ERA in nine starts in 2026, striking out 47 in 45 1/3 innings. Depending on the length of his latest recovery process, he could be back in time to help a club next season."

Milwaukee should bring Woodruff back, but on a cheaper contract

Jul 4, 2026; Phoenix, Arizona, USA; Milwaukee Brewers pitcher Brandon Woodruff (53) throws in the third inning against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Rick Scuteri-Imagn Images | IMAGN IMAGES via Reuters Connect

Woodruff has spent his entire nine-season career with the Brewers, and despite his injury history, remains a valuable pitcher. Though he was limited to just nine outings this season, the former All-Star posted a 2.98 ERA. His performance hasn't been his problem; it's the fact that he hasn't pitched a full season since 2022.

The Brewers brought back Woodruff this season on a $22 million qualifying offer, yet with him injured again, it's hard to imagine a team signing the veteran hurler to a lucrative contract for more than a year or two.

Milwaukee has plenty of promising young pitchers in addition to Misiorowski, including Quinn Priester, Kyle Harrison and Logan Henderson, and that's not even counting a few solid prospects that are nearing the big leagues. The Brewers should consider bringing Woodruff back on a cheaper short-term contract as a veteran presence and to give their young pitchers more time to develop.