The Milwaukee Brewers could be in prime position to bring back Jordan Montgomery this offseason, and the idea is gaining traction among fans and insiders alike.
With rotation depth a key offseason focus for the Brewers, adding a veteran left-hander with big-league experience could be a smart move. Brewers pitching rumors and free agent tracker conversations are already highlighting Montgomery as a potential reclamation project with upside.
As teams explore veteran arms to stabilize their rotation for 2026, Jordan Montgomery Brewers signing chatter is rising. Milwaukee’s front office has shown interest in low-risk, high-reward pitching additions, making a reunion with Montgomery an intriguing possibility. Jordan Montgomery could be signed by the Brewers in free agency.
*Prediction*
More MLB Content From TWSN:
Top-3 MLB World Series Contenders
Aaron Judge Needs to Request a Trade from the New York Yankees
Montgomery’s name has come up throughout the offseason as a low-cost but potentially valuable arm for the Brewers, especially since the organization already has familiarity with him after acquiring him at the 2025 trade deadline.
Brewers insider Adam McCalvy noted that a reunion between Montgomery and Milwaukee isn’t far-fetched, pointing out that Montgomery visited American Family Field during his Tommy John rehab and expressed interest in returning to a club with strong pitching development and good defense.
Even though Montgomery hasn’t pitched in 2025 due to elbow surgery, the Brewers could view him as a one-year bounce-back candidate who fits their strategy of maximizing veteran talent without heavy financial commitment.
This year was an injury-plagued mess for Montgomery. He missed the entire 2025 season while recovering from Tommy John surgery, which sidelined him before Opening Day and prevented him from making a single mound appearance.
Before that, his 2024 season with the Arizona Diamondbacks was rough: Montgomery posted a 6.23 ERA in 117 innings with a below-average performance that frustrated both fans and team ownership.
Despite the struggles, his underlying career track record shows sustained success at a high level, and his veteran presence could be a stabilizing force in a Brewers rotation that could use depth and experience.
Montgomery previously signed a one-year, $25 million contract with the Diamondbacks that included vesting options for 2025, but his performance did not match the price tag, and he was eventually sidelined by injury. With his contract now expired and his future open in free agency, Montgomery may be looking for a team willing to bet on his health and veteran savvy.
For the Brewers, signing Montgomery could deliver veteran left-handed depth at a bargain price and provide rotation insurance if young arms falter or injuries arise.
Milwaukee could offer a short-term deal with incentives that align with Montgomery’s need to prove himself after missing a full season. In a market that values pitching depth, Montgomery’s mix of experience and upside makes him a logical candidate for the Brewers’ offseason plans.
In the end, a Brewers reunion with Jordan Montgomery could be a mutually beneficial opportunity, giving Montgomery a chance to reestablish himself while the Brewers bolster a rotation that needs reliable veteran arms for a 2026 playoff push.