For small-market teams like the Milwaukee Brewers to win a World Series, most everything has to fall into place. Not only do the right decisions need to be made, both from the front office and manager, but players need to be firing on all cylinders and they have to remain healthy. In 2026, enough chips fell into place for the Brew Crew to bring home their first-ever World Series title.
It started with Matt Arnold hitting on a February trade that brought three players to the World Series roster: David Hamilton, Shane Drohan, and Kyle Harrison. Arnold also added Gary Sánchez as the backup catcher before making key deadline acquisitions in Dustin May, JoJo Romero, and Antonio Senzatela. Electing not to part ways with Logan Henderson for Tarik Skubal, who was reportedly was a must-have for the Detroit Tigers, also worked out in Milwaukee's favor, as the Brewers won a championship without Skubal, and now have Henderson for the next half a decade.
On the field, Pat Murphy made several important decisions, including rewarding Jake Bauers with the everyday first-base job early in the season, sticking with Hamilton at third base throughout the playoffs, despite Joey Ortiz being one of the better hitters in the league post -All-Star break, and riding Aaron Ashby's left arm throughout the postseason to an MLB-best 18.0 scoreless innings.
This year, every move, decision, and contribution seemed to come together at the right time. There is no guarantee that will happen again in 2027, but already preparations for the upcoming season are taking place. Here, we take a look at the Brewers' three biggest needs during the modified 2026-27 offseason.
What do the Milwaukee Brewers need to address this offseason?
1. Figure out who's on first alongside Andrew Vaughn
Following an impressive second-half run with the Brewers in 2025, Andrew Vaughn appeared to be the favorite to handle the everyday duties at first base heading into this season. Instead, Jake Bauers won the job and has since put himself in a strong position to earn a well-deserved payday. That said, Vaughn still has one year of team control remaining, and Bauers is facing a qualifying offer he's likely to decline, making it likely the Brewers will be looking for a left-handed counterpart to complement Vaughn in 2027.
On the free-agent market, options outside of an unlikely Bauers reunion include Nathaniel Lowe, Rowdy Tellez, and Dominic Smith, as they all offer left-handed bats. However, Milwaukee could just as easily turn to an internal option. Blake Burke, the Brewers' 2024 first-round pick, hit 34 home runs across the Double-A and Triple-A levels last season, while 2025 first-round corner infielder Andrew Fischer launched 48 home runs in High-A and Double-A. Giving someone like Burke or even Fischer an opportunity to ease into a part-time role alongside Vaughn makes plenty of sense.
2. Answers at catcher
After his World Series MVP performance, there is little doubt the Brewers would love to have William Contreras behind the plate in 2027. However, with just one year of team control remaining and the current payroll structure in baseball, Milwaukee faces an important decision this offseason: trade Contreras now and recoup valuable pieces in return, or retain him through 2027, extend a qualifying offer next winter, and receive draft-pick compensation if he signs elsewhere. With CBA negotiations taking place this winter, and a salary floor potential being introduced, a third option that previously seemed unlikely could possibly exist: signing Contreras to a contract extension.
Whatever happens with Contreras, it's important to remember that Gary Sánchez is also headed for free agency. That could leave Jeferson Quero potentially in line for his first extended opportunity at the major-league level. Having Quero mentored under Contreras for a year would be invaluable to his development, though it would limit his playing time and opportunities at the plate. The Brewers also acquired left-handed hitting catcher Bo Naylor from the Cleveland Guardians at the trade deadline, who certainly possesses some upside, but is far from a sure thing. Answering this question of how their catching room will shake out in 2027 remains one of the Brewers' top priorities during the modified offseason.
3. Add right-handed relief pitching depth
Right-handers departing from the pitching staff include Brandon Woodruff, Antonio Senzatela, Dustin May, and Bryse Wilson. Losing those four arms leaves Milwaukee with just nine right-handed pitchers among the 18 pitchers on their 40-man roster. That group includes Quinn Priester, who missed the entire 2026 season with thoracic outlet syndrome, eventually undergoing surgery in July, and All-Star closer Trevor Megill, who may or may not be traded this offseason.
With that in mind, it wouldn't be surprising to see the Brewers take a few low-risk fliers on right-handed pitching this offseason. The free-agent market is considerably stronger on the pitching side than among position players, giving Milwaukee several avenues to explore. Whether that means a reunion with Senzatela, taking a chance on a high-upside free agent like Jonathan Loáisiga, or identifying another under-the-radar arm with the intangibles the organization values, expect the Brewers to make at least one addition in this department.
