Is there any chance the Brewers re-sign Jordan Montgomery?

The Milwaukee Brewers had a quiet, unspectacular trade deadline performance, one that was predicated upon not messing with a good thing. The team is on fire right now, and with so many young pieces set to contribute for years to come, there was no reason to mortgage the future on some expensive rentals.

That being said, the team did bring in one peculiar player at the deadline in their trade for Shelby Miller with the Arizona Diamondbacks: southpaw Jordan Montgomery.

Montgomery is an impending free agent and is out for the season after needing Tommy John surgery in early April. The Brewers are assuming $2 million of his remaining salary (roughly $7.5 million) this year, which helped drive down the cost to acquire Miller.

There doesn't seem to be much else there—the small-market Brewers made a savvy move by eating salary so as not to deal with the prospect cost in a very expensive reliever market. However, what if Milwaukee's true ambition was getting a chance to work with Montgomery ahead of free agency?

Brewers could unite with rehabbing Jordan Montgomery on cheap, short-term pact

Montgomery, who will turn 33 in December, isn't likely to pitch before May or June of the 2026 season. He was also a disaster last year with Arizona, recording a 6.23 ERA and -1.4 bWAR in 117 innings.

Doesn't sound like a very attractive profile, does it? Why would the pitching-rich Brewers even bother trying to re-sign an arm like that?

Well, 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.

And, lest anyone forget, Montgomery was a tour de force prior to his Diamondbacks debacle, pitching to a 3.48 ERA in more than 520 innings with the New York Yankees, St. Louis Cardinals, and Texas Rangers. He was also brilliant for the latter in their run to the 2023 World Series, allowing just a 2.90 ERA in 31 postseason frames.

The thing with a guy like Montgomery is, maybe the Brewers did want to sign him in free agency, but perhaps not enough to beat out 29 other teams to do it. So, they wanted to bring him in now to see what he's got and how he reacts to their system and pitching development team. That kind of information is invaluable, and can really only be ascertained when you have a guy in your building.

Alternatively, maybe the Brewers knew how much they already loved him and how badly they wanted to sign him in free agency. So, in an attempt to give themselves a leg up in his sweepstakes, they brought him in now with the plan of trying to sell him on Milwaukee for the long-term by showing him how great the franchise/fanbase/internal development team is. Again, that's something that can really only be simulated during a free agency visit.

Again, the most logical reason for the inclusion of Montgomery in the Miller deal was using salary to drive down prospect cost. However, a World Series hero not even two years ago, there's a chance the pitching factory in Milwaukee could claim the southpaw as its latest resurrection project.