Milwaukee Brewers fans are very, very far away from thinking about next year right now; they've never gotten to celebrate a World Series title before, and you better believe they're going to make the most of it after their team polished off a five-game win over the Tampa Bay Rays on Wednesday night. Jackson Chourio and the gang will never have to buy a drink in Wisconsin again.

However, as one door closes, another opens. Just because the Brewers have a championship parade to plan doesn’t mean their work is done. On the contrary: If we know one thing about this front office, it's that they're constantly tinkering, always looking for ways to find value on the margins. And while they finally scaled the mountain this year, mounting a title defense against the Los Angeles Dodgers and other contenders in 2027 will be a tall task — especially considering the departures they could face this winter.

Some of those departures will be simply free agency running its course, while others will be the sorts of tough, proactive decisions you need to make when you're a small-market team. Either way, Milwaukee has some tough goodbyes ahead of them this offseason.

C William Contreras

We'll start with the most difficult pill to swallow. Contreras has blossomed into a star since coming to Milwaukee, and he's coming off a legendary postseason run both at the plate and behind it. But he's also about to enter his final year of team control in 2027, and the Brewers under Matt Arnold have a long history of flipping their stars early rather than losing them for nothing in free agency.

And make no mistake: Contreras will command a haul, even for just one season of his services. He's been that good, and the catching situation around the league is that shaky. They did it with Devin Williams and Freddy Peralta, and Contreras is almost certainly next in line.

RHP Trevor Megill

Megill hasn't gotten nearly as much trade buzz, but there's reason to think Milwaukee could look to be a year early here as well. He's grown into one of the best high-leverage relievers in baseball over the last few years, but he'll also be 33 next season, with arm trouble in his recent past that should give the Brewers pause. Oh, and he'll be a free agent next winter, too.

All of which points to a potential deal, especially considering how successful the Brewers have been in building bullpens on the cheap over the years. If they were willing to flip Williams to the New York Yankees a year before his free agency, why wouldn't they do the same with Megill? Selling high at such a volatile position is almost always the smart long-term play.

OF/1B Jake Bauers

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.

RHP Dustin May

May was an intriguing add at the trade deadline, a former top prospect with a very live arm who showed flashes of upside with the St. Louis Cardinals. It didn't quite work out as expected in Milwaukee, although he has rebounded in a relief role in October.

That said, the starting pitching market is such that May is bound to find suitors who will pay him to be a part of their rotation next year (and maybe in 2028, too). Milwaukee is overflowing with viable starters every year, and they'll likely feel no need to throw $15 million a year or so at another one.

LHP JoJo Romero

Romero was the other piece coming to Milwaukee in the May deal, and he's largely been as advertised — especially in the NLCS and the World Series, where he's consistently neutralized lefties. But again, much like with Megill and May above, the Brewers simply churn out quality pitchers too regularly to be paying market price. Romero will likely see a high seven-figure or low eight-figure deal in free agency, and Milwaukee's resources are better spent elsewhere given the arms they have in house.