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

Could Brewers Reunite With Former World Series Champ Acquired In Salary Dump?

Originally posted on Milwaukee Brewers on SI
By Curt Bishop | Last updated Aug 9, 2025 11:27 AM ET

The Milwaukee Brewers had a relatively modest trade deadline, not making any major moves, though they currently have the best record in Major League Baseball and lead the National League Central by five games over the Chicago Cubs.

One of the moves they made was a trade with the Arizona Diamondbacks to acquire pitchers Shelby Miller and Jordan Montgomery. Miller has slotted right into the Brewers bullpen, while Montgomery is out for the season after undergoing Tommy John surgery. He was included in the deal is nothing more than a salary dump.

However, Brandon Glick of FanSided proposed the idea of Milwaukee reuniting with Montgomery in the offseason, as the veteran left-hander will be a free agent.

"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.," Glick writes.

"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."

Could Brewers Bring Back Veteran Hurler On Cheap Contract For 2026?

Montgomery struggled last season with Arizona, going 8-7 with a 6.23 ERA in 21 starts and four relief appearances after signing with the team just days prior to Opening Day. He opted into the final year of his contract, but underwent Tommy John surgery towards the end of spring training.

However, the veteran left-hander does have a strong track record. He helped the Texas Rangers win their first ever World Series title in 2023, and has proven that he can pitch in the postseason. His injury issues will likely drive his price down.

Perhaps it could be a low-risk, high-reward type deal. Milwaukee brought back Brandon Woodruff following an arm injury on a cheaper contract, and he has since made his return.

Montgomery should be back at some point in 2026, so the Brewers could give him an opportunity to rebuild his value and potentially return to the free agent market in 2027.

So, this move could ultimately prove to be more than just picking up a player because of another team's salary dump. Montgomery could still have some real value when he hits the open market, and the Brewers could take advantage of a much lower price tag.

This article first appeared on Milwaukee Brewers on SI and was syndicated with permission.

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