The Milwaukee Brewers weren’t just a pleasant surprise in 2025-they were one of the best teams in baseball, period. Quietly and methodically, they put together a 97-win season, the most in franchise history, and finally broke their postseason drought by taking down the rival Cubs in a hard-fought NLDS. That series win meant a little more, too-beating former manager Craig Counsell and the Cubs added a layer of satisfaction for Milwaukee fans.
Sure, their playoff run ended in a sweep at the hands of the eventual champion Dodgers in the NLCS, but the Brewers made a statement. This wasn’t a fluke.
This was a team built on elite pitching, sound defense, and just enough timely hitting to get the job done. And while the offense still has work to do, the Brewers head into 2026 with a clear identity-and a whole lot more respect.
The rotation was the heartbeat of the 2025 squad, and that’s not expected to change. But there’s a wrinkle heading into 2026 that could give Milwaukee even more depth on the mound: Jordan Montgomery might be back in the fold.
Let’s rewind for a second. At the trade deadline last season, the Brewers made a few under-the-radar moves to bolster their pitching staff.
One of those was acquiring reliever Shelby Miller from the Diamondbacks. Miller only pitched in 11 games before getting hurt, but the real intrigue came from the fine print of that deal.
To get Miller, the Brewers also absorbed the remainder of Jordan Montgomery’s 2025 contract-roughly $7.5 million-despite the fact that Montgomery was rehabbing from Tommy John surgery and didn’t throw a pitch all year.
At the time, it looked like a pure salary dump. Most assumed Montgomery would never actually suit up for Milwaukee.
But now? That’s changed.
According to reports, the Brewers and Montgomery have kept the door open for a reunion in 2026. Despite a rocky end to his time with the Diamondbacks, Montgomery apparently made a strong impression in Milwaukee.
He even showed up at American Family Field in September to make a donation to the Brewers Community Foundation-right around the time he learned he’d earned a $500,000 bonus for being traded. That’s not the kind of gesture you make if you're completely checked out.
Montgomery is expected to start throwing bullpen sessions in January, which puts his availability for Opening Day in question. But if the Brewers can work out a deal that accounts for the risk-think incentives or a short-term prove-it contract-a return feels very much on the table.
And it would make a lot of sense. In eight big league seasons, Montgomery owns a 46-41 record with a 4.03 ERA.
That’s solid, dependable production. But his last full season in 2023 was even better: a 3.20 ERA over 30+ starts while splitting time between the Cardinals and Rangers.
That version of Montgomery would be a huge asset to a Brewers rotation that currently lacks a left-handed starter.
Right now, Milwaukee’s rotation leans righty-heavy. Unless they stretch out Aaron Ashby, DL Hall, or newly acquired Angel Zerpa-each of whom spent most of last season in the bullpen-there’s no clear lefty presence. Montgomery could fill that void, offering experience, balance, and postseason poise to a staff that already knows how to carry a team.
And with Freddy Peralta’s future still uncertain amid trade rumors, the Brewers would be wise to shore up their depth sooner rather than later.
Montgomery may have been a forgotten name in 2025, but in 2026, he could be a key piece of a Brewers team looking to prove last season was just the beginning.