Brewers Projected To Lose Injured Pitcher To Red Sox In Free Agency

This former All-Star never got a chance to shine with the Brewers.

May 26, 2025; Milwaukee, Wisconsin, USA; General view of a Milwaukee Brewers logo during warmups prior the game against the Boston Red Sox at American Family Field. Mandatory Credit: Jeff Hanisch-Imagn Images | Jeff Hanisch-Imagn Images

The Milwaukee Brewers are heading into a pivotal offseason after falling just short of a World Series appearance in 2025. Their impressive postseason run ended in the National League Championship Series, leaving the front office with several tough roster decisions to make — especially when it comes to the starting rotation.

This winter, the Brewers will see several key pitchers hit free agency, including Brandon Woodruff, José Quintana, and Jordan Montgomery. While ace Freddy Peralta is expected to stay put, the rest of Milwaukee’s pitching staff could look very different when the 2026 season begins.

Montgomery was acquired from the Arizona Diamondbacks in the Shelby Miller deal but did not pitch for Milwaukee after undergoing Tommy John surgery before the season. His market will be difficult to predict given his injury, but Kerry Miller of Bleacher Report predicts that a team from the American League East will snag him this winter.

Brewers Could Lose Injured Pitcher To Red Sox In Free Agency

Sep 22, 2024; Milwaukee, Wisconsin, USA; Arizona Diamondbacks starting pitcher Jordan Montgomery (52) pitches in the first inning against the Milwaukee Brewers at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images | Benny Sieu-Imagn Images

“News of Monty needing a second TJ surgery broke just days before the 2025 campaign began, which means he's probably going to miss a significant chunk of 2026,” Miller wrote. “But someone will probably take a shot on him with a contract similar to what Shane Bieber signed last winter ($10M with a $16M player option for a second season) when he was at the same point in his TJ recovery.”

Miller predicts that Boston will sign Montgomery to a one-year, $6 million contract with a $14 million player option for 2027 — a low-risk, high-reward deal for a team in desperate need of pitching depth.

For Milwaukee, Montgomery’s departure would hardly come as a surprise. He never appeared in a game for the Brewers, so losing him in free agency doesn’t change their immediate plans. The team should probably focus on re-signing either Woodruff or Quintana, or perhaps exploring lower-cost options such as Walker Buehler or Chris Bassitt to stabilize the rotation.

With several holes to fill and limited payroll flexibility, the Brewers will need to be strategic in how they approach free agency. But as far as Montgomery goes, his loss won’t sting — it simply closes the book on a short-lived chapter that never really began.

The Brewers will need to add some starting pitching, however, and that is something that can't go unnoticed this winter.

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