The Brewers are World Series champions, but that ring doesn’t put the front office on cruise control. Milwaukee can enjoy the 2026 ride, sure, but the bigger question is what comes next. With 2027 looming and a target now painted on their backs, this winter matters a lot.
One of the biggest decisions sits right in the middle of the roster: William Contreras. He has one more season of team control before free agency after the 2027 season, and the trade chatter has already started.
The case for keeping him, though, is loud. In the World Series, he proved why he belongs in Milwaukee’s long-term plans, winning World Series Most Valuable Player Award behind both his offense and his elite defense.
Even with a high price tag, the Brewers should be figuring out how to keep that relationship intact, or at the very least mapping out a path forward this winter.
Another area that deserves attention is power. Milwaukee’s regular season numbers told a simple story: the Brewers ranked tied for 28th with 154 home runs as a team.
That weakness didn’t define them when the stakes got highest, but adding more pop would still make life easier. There may already be an internal answer waiting.
Andrew Fischer crushed 48 home runs and drove in 114 runs in 2026 across 126 games, and getting him to the big leagues could help solve that problem.
The bullpen, even after carrying the team through the 2026 playoffs, may also need fresh arms. JoJo Romero is set to hit free agency, and Antonio Senzatela is likely to follow.
Trevor Megill has just one more season of team control, which figures to put him in trade-rumor territory too. Milwaukee can never have too much relief depth, and adding one or two bullpen arms would make sense.
Then there’s Abner Ashby, who gave the Brewers one of the most remarkable postseason relief stretches in big league history. He threw 18 scoreless innings in the postseason and piled up 20 strikeouts.
That kind of run is hard to ignore. Ashby has also made clear that he still hopes to start someday, which raises the question of whether 2027 could be the year to try it.
It would give Milwaukee another left-handed option, but it would also thin out the bullpen. For the Brewers, that’s the kind of offseason choice that can shape what comes next.
In Other News...
Cooper Pratt Just Gave Brewers Fans Another Reason To Dream
Cooper Pratts arrival on June 16 already felt like the kind of moment Brewers fans could circle for years, and the rest of the summer only sharpened that feeling. The rookie did not just get his feet wet in the majors, he became part of a run that carried Milwaukee to its first World Series title less than five months later, with strong regular season and postseason production helping make the leap from prospect to big leaguer look awfully smooth.
The bigger reason to keep dreaming is the shape of the future around him. Milwaukee locked Pratt into a long-term extension before he had even played a single big-league inning, giving the club control for years to come and signaling just how much faith it already had in his ceiling. Pratt has sounded equally comfortable with where things are headed, and for a fan base still savoring a championship, that kind of stability is almost as encouraging as the ring itself. [Read more 🡒]
Brewers Title Celebration Included A Personal Moment Fans Will Love
The Brewers World Series championship celebration was already packed with the kind of joy that tends to spill well beyond the trophy presentation, but two players found a way to make the night even more personal. David Hamilton and Dustin May each used the on-field moment to share family news with their wives, turning a team milestone into something a little more intimate and a lot more memorable for fans watching along.
Both couples posed for photos on the field with miniature jerseys bearing their last names and numbers, a small but fitting touch in the middle of a big celebration. It was the kind of scene that fits a championship night in Milwaukee, where the baseball part of the story was only part of what made the evening special. [Read more 🡒]
Brewers Face 3 Tough Roster Calls After Winning It All
After finally winning their first World Series title by beating the Tampa Bay Rays in five games, the Brewers are already staring at the kind of winter that comes with success. A championship changes the conversation, but it does not freeze a roster in place, and Milwaukee could still be forced to sort through questions at first base, in the rotation and in the bullpen as the front office weighs what the next version of the club should look like.
One set of speculative trade ideas tries to map out those next steps by putting a bat and two arms on the board as possible fixes. The thinking is straightforward enough: if the Brewers want to keep the window open after reaching the top, they may need to chase help in more than one area, even if none of these scenarios is rooted in any reported talks or confirmed moves. [Read more 🡒]