Aug 4, 2025; Atlanta, Georgia, USA; A detailed view of a Milwaukee Brewers hat and glove in the dugout against the Atlanta Braves in the fourth inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images Brett Davis-Imagn Images

Why Brewers Should Re-Sign Jordan Montgomery Quickly

Originally posted on Milwaukee Brewers on SI
By Patrick McAvoy | Last updated Oct 21, 2025 3:44 PM ET

The Milwaukee Brewers are going to face a few major decisions in the starting rotation this offseason.

One involves Freddy Peralta and the other biggest one is Brandon Woodruff. Peralta has an $8 million club option for the 2026 season, which is a no-brainer to pick up. For him, the question is whether to trade him a year before he hits the open market or roll the dice on the 2026 season.

Woodruff has a $20 million mutual option, which doesn't seem very likely to be picked up. If not, could the Brewers end up re-signing him?

José Quintana isn't guaranteed to return as well, but that's not as big a question as Peralta and Woodruff's future. Regardless, the Brewers should bring in another arm no matter what and a perfect option could be Jordan Montgomery.

The Brewers should re-sign Jordan Montgomery

Milwaukee actually acquired Montgomery in a trade with the Arizona Diamondbacks this past summer, but he missed the entire season due to injury. Montgomery never pitched a game for the Brewers and will hit the open market this offseason looking to rebuild his value after a bad 2024 season and injury-filled 2025 campaign. That's where the Brewers could come in. Milwaukee has proven over and over again that it can bring in veteran pitchers and find success. Take a look at Quintana, for example.

Even with Woodruff, the Brewers re-signed him knowing he would miss the 2024 season. He rehabbed with the team and came back ready to roll in 2025. Montgomery is a guy who had a 3.48 ERA across 94 starts from 2021 through 2023 with the New York Yankees, St. Louis Cardinals, and the Texas Rangers. He's a big-game pitcher who won a World Series with the Rangers, but struggled in Arizona after signing way too late.

If the Brewers could bring back Montgomery, and do so quickly, it would give the front office more flexility to make decisions for the rotation as well.

Rolling the dice on Montgomgery on a cheap, prove-it deal would give the team depth at their disposal no matter what happens with Peralta, Woodruff, and Quintana. The Brewers' championship window is open. There's an argument that the Brewers shouldn't let any of those guys walk, but adding Montgomery back would be a nice insurance policy.

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

More must-reads: