Brewers' $22 Million Offseason Gamble Was A Big Mistake

The Milwaukee Brewers brought back one of their veteran pitchers this offseason despite his injury history, and it has not gone great.

Aug 4, 2025; Atlanta, Georgia, USA; A detailed view of a Milwaukee Brewers hat and glove in the dugout against the Atlanta Braves in the fourth inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images | IMAGN IMAGES via Reuters Connect

The Milwaukee Brewers boast the best record in baseball, even though the team decided to stay conservative over the offseason and at the trade deadline.

Milwaukee has had consistent success for nearly a decade, reaching the postseason in seven of the last eight seasons, and is on track to reach the playoffs again this season, even though the team ranks in the bottom half of the league in payroll. Despite their continued success, the Brewers have yet to make a deep postseason run and reach the World Series, most recently getting swept by the Los Angeles Dodgers in the NLCS last year.

The Brewers had the opportunity to make a big swing at the trade deadline and were rumored to be in the running to acquire Tarik Skubal, but ultimately acquired Dustin May and JoJo Romero from the St. Louis Cardinals instead. Milwaukee has been conservative since the offseason, focusing on locking down players like Cooper Pratt and Luis Lara long-term, with the team's largest financial commitment coming from Brandon Woodruff's $22 million qualifying offer.

Woodruff can't stay on the field

Jun 28, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers pitcher Brandon Woodruff (53) high fives teammates in the dugout during the sixth inning against the Chicago Cubs at American Family Field. Mandatory Credit: Jeff Hanisch-Imagn Images | IMAGN IMAGES via Reuters Connect

Though Woodruff performed well to begin the season, posting a 2.98 ERA with 47 strikeouts in nine starts, the 33-year-old suffered a shoulder injury requiring surgery and will miss the rest of the season. With his injury history and the significant time he'll miss again this season, Woodruff's $22 million contract easily makes him one of the most overpaid players in the league.

"When Brandon Woodruff made the surprise decision to accept his qualifying offer from the Brewers, it changed the math of their offseason, and that unexpected payroll commitment for a club that operates with a small-market budget is a big part of the conversation here," Bleacher Report's Joel Reuter wrote on Wednesday. "The 33-year-old was excellent over nine starts before arm fatigue preceded a season-ending shoulder injury. The Brewers have been one of the best teams in baseball, but Woodruff has not delivered relative to the significant slice of the payroll pie he is occupying."

Woodruff has not delivered for the Brewers this season based on how much he's actually played. It was a gamble for Milwaukee to extend the 33-year-old a qualifying offer due to his injury history, but they would have received draft compensation had Woodruff declined and signed elsewhere.

Woodruff has spent his entire nine-year career with the Brewers and is a fan favorite, so it's not surprising that he would want to stay, but after pitching in only 23 games since 2023, before this season, his injury history should have been a greater concern.

Now, Milwaukee is stuck paying $22 million this season for an injured pitcher instead of reallocating the money to bringing in more talent for a playoff run.