At the 2025 trade deadline, the Milwaukee Brewers acquired injured left-hander Jordan Montgomery in a salary dump move by the Arizona Diamondbacks. The 32-year-old underwent Tommy John surgery in early April and, at the time of the trade, was still owed approximately $7.5 million of his $22.5 million salary for the season.
As part of the deal, the Brewers agreed to cover around $2 million of that remaining amount, including a $500,000 bonus Montgomery earned for being traded. With free agency looming and an entire season essentially lost to injury, Montgomery is likely to be a low-risk, short-term signing option this winter.
Milwaukee Brewers urged to pursue a reality where Jordan Montgomery pitches for them
At first glance, the trade for Montgomery looked like nothing more than a financial move from Arizona and a unique way for Milwaukee to simultaneously acquire Shelby Miller. The assumption was that Montgomery would never throw a pitch for Milwaukee. But what if that’s not the case?
There’s a realistic scenario where the Brewers bring him back on a team-friendly, prove-it deal, giving Montgomery a chance to rebuild his value before hitting free agency again in the near future. At Fansided, Contributor Brandon Glick wrote the following:
“Those factors will drive his price way down in free agency. He’ll likely opt for one of the increasingly popular “one-and-one” deals, where he gets a muted salary in the first season of the contract while rehabbing, and then a player option for the second year, so he can decide if he wants to test free agency again after returning.
That should be music to the ears of a small-market team like the Brewers, who are finally reaping the benefits of slow-playing Brandon Woodruff’s recovery.”
Whether or not the Brewers choose to re-sign Montgomery remains to be seen, but the door is certainly open. With his value likely at a low point and Milwaukee’s track record of maximizing pitching talent, a short-term, incentive-laden deal could benefit both sides.
What started as a throw-in to a deadline deal might just turn into a savvy offseason addition, if the Brewers are willing to bet on a bounce-back.
