As the Winter Meetings kick off on December 7, the Milwaukee Brewers enter a crucial period to finalize their offseason plans, with many deals often coming together during this time. In their push to strengthen the roster and set priorities for 2026, two pressing questions emerge that could have a major impact on the team’s strategy.
2 burning questions the Milwaukee Brewers must address at this year’s Winter Meetings
1) What is the state of the payroll?
There have been conflicting reports about just how tight the Brewers’ 2026 payroll is. After a team of reporters at The Athletic suggested the Brewers are concerned about payroll, Matt Arnold, the organization’s President of Baseball Operations, poured water on the situation, telling MLB.com’s Adam McCalvy, that the team doesn’t need to shed payroll before the 2026 season. Regardless, Brandon Woodruff accepting a $22.025 million qualifying offer may have complicated some plans or initially be limiting their flexibility, which could lead to Milwaukee finding creative ways to shed payroll in an effort to increase their ability to make more offseason or in-season additions.
One way to do that while acquiring valuable pieces would be trading higher-salary players like Freddy Peralta or Trevor Megill. However, with Peralta set to make $8 million in 2026 and Megill projected, by MLB Trade Rumors, for an arbitration salary of $4.2 million this year, trading either wouldn’t be a huge change to the payroll. Alternatively, the team could restructure Woodruff’s deal, with the most logical move being a deferral of some of his 2026 salary to a later date, rather than a long-term extension. If payroll isn’t a concern, however, Milwaukee could have more room to make key signings, bolstering an already impressive roster that finished last season with the best record in baseball. If such a move does happen at the Winter Meetings, one that adds anything to the 2026 payroll, it would be a signal to Brewers fans that the payroll situation is nothing to worry about.
2) Are the Brewers content with “running it back?”
Like last offseason, the Brewers enter 2026 with most of their core players returning. Coming off a three-peat in their division and their first NLCS appearance since 2018, it would be tempting to simply roll out the same roster and rely on internal growth. Last season, progress from Brice Turang, the continued rise of Jackson Chourio, the emergence from Chad Patrick, Quinn Priester, and Issac Collins, and the flashes of star potential of Jacob Misiorowski all helped propel the team forward, even with José Quintana being their most significant free-agent addition.
Sometimes, though, it pays to be aggressive. In 2019, for example, the Brewers went “all-in” by signing one-year, high-value deals with Mike Moustakas and Yasmani Grandal. Doing something similar to strengthen an already impressive lineup could be exactly what the team needs to achieve its postseason goals, especially with power house teams spending more than ever on impact players. With a new CBA on the horizon, the timing for a bold move feels right.
With questions surrounding payroll and whether to run back the same talented core, knowing there are legit concerns about a lower-spending roster’s ability to contend for a World Series, the Brewers would be wise to have an approach in mind before Winter Meetings begin. This will allow the team to approach negotiations strategically, make informed decisions during the meetings, and chart a clear path for the rest of the offseason.
