Every Milwaukee Brewers free agent and their possible big-market poachers

For the first time in franchise history, Milwaukee Brewers are officially World Series champions. But while the state of Wisconsin will be celebrating this one for a long, long time, Matt Arnold and the team’s front office have already pivoted to their title defense next season (you know, assuming there is a next season). And that means making several tricky decisions regarding members of this run who are now set to hit free agency.

Of course, Milwaukee is better off here than most; one of the upsides of being a small-market team that builds through drafting and developing is that you don’t deal with nearly as much roster turnover. The Brewers are only scheduled to have four outright free agents this offseason, as well as three option decisions to make.

Still, that list features several big names — including a franchise icon and their playoff MVP.

Milwaukee Brewers have some difficult free agency decisions to make this winter

How will the Brewers handle their seven potential free agents, and where will they all ultimately end up? Here’s the complete list below.

How much does Brandon Woodruff have left in the tank?

It’s almost impossible to imagine Woodruff playing for any other team than the one that drafted him in the 11th round back in 2014. The Brewers love the right-hander, and the feeling appears to be very much mutual. So the question is less whether Woodruff will sign elsewhere next season, and more whether he’ll play next season at all.

Woodruff has given no indication that he’s considering retirement; on the contrary, he just slogged through months of rehab to get back on the mound in the World Series. But he’ll turn 34 in February, with a lengthy injury history behind him. I’d bank on the two sides coming to an agreement on a short-term deal for 2027, but don’t be shocked if he chooses to hang it up for good now that he’s finally reached the top of the mountain.

William Contreras could be traded after historic playoff run

There’s approximately a zero percent chance that Contreras is allowed to hit free agency; he has a $14 million team option for 2027, a bargain based on his production this season. Once the Brewers pick that option up, though, will they look to trade him a year before free agency — much in the same way they’ve done with stars like Corbin Burnes, Devin Williams and Freddy Peralta?

Recent history certainly points to yes; Milwaukee would much rather flip him for future value than lose him for nothing next offseason. That’s a tough pill to swallow based on everything he’s meant to this franchise and its first-ever World Series run, but that’s the business that small-market teams are in.

Brewers will let Jake Bauers cash in elsewhere

Bauers is one of the feel-good stories of this Brewers run, a former prospect bust who put together a career year at the plate this season. Now, as he hits free agency, he’ll be looking to cash in with some well-earned security.

I just don’t think that security will come from Milwaukee. After all, this is what the Brewers do: They find diamonds in the rough, help polish them off and then wish them well as they get paid elsewhere. The Brewers outfield is pretty full for 2027, and they can pretty easily find a new platoon partner for Andrew Vaughn at first on the cheap. They’re much more likely to try to identify the next Bauers rather than sacrifice valuable payroll space to keep the old one, as plenty of teams needing first-base help (Mets, anyone?) are happy to give him a three- or four-year deal.

Milwaukee has more than enough pitching depth as it is

The Brewers simply churn out quality pitchers too regularly to be paying market price. That makes decisions simpler around several pending free agent pitchers, from starter Dustin May to relievers JoJo Romero and Antonio Senzatela. Even if they choose to let all three walk, they can still enter next year with a rotation featuring Jacob Misiorowski, Logan Henderson, Kyle Harrison, Quinn Priester, Robert Gasser and more and a bullpen featuring the three-headed monster of Trevor Megill, Abner Uribe and Aaron Ashby. This is what Milwaukee does, and it won’t change any time soon.