The (second) most painful trade Brewers could make at the Winter Meetings

It may seem like the Milwaukee Brewers are destined for a quiet offseason, with much of their record-breaking 2025 squad set to return for the 2026 season. However, President of Baseball Operations Matt Arnold and the rest of Milwaukee's front office have some very significant decisions to make this offseason, with implications that could determine the direction of the club for the foreseeable future.

With Milwaukee coming off of a National League Championship Series appearance, just their fourth appearance in the championship series in the history of their franchise, Arnold and company have to decide whether or not 2026 is a season in which they go "all-in" or if they continue their strategy of making moves that allow the Brewers to keep their competitive window open for an extended amount of time. Adopting the latter strategy would look like trading away their players on expiring contracts, most notably Freddy Peralta, who would otherwise serve as the team's ace in 2026, in an effort to add players to their roster who can impact their organization for several years to come. Such a strategy would involve replacing the traded players with new individuals who allow the Brewers to once again qualify for the postseason, but don't impact the organization’s ability to field competitive teams in the future.

Already, plenty of rumors have surfaced regarding the other teams' interest in Milwaukee's top starter, Peralta, which should come as no surprise to Brewers fans seeing as their team has traded away pitchers entering their final season of team control in each of the last two offseasons. Peralta's departure, while it would theoretically allow Milwaukee to restock their farm system with new talent that could potentially impact the major league roster immediately, would be detrimental to the Brewers' chances of winning a World Series in 2026. As such, losing Peralta to a team more serious about competing for a World Series title in 2026 would be the most painful trade the Brewers could make at the Winter Meetings, despite the fact that it could increase their chances of fielding a competitive roster beyond the 2026 campaign.

When it comes to painful trades, which take into account the short-term impact of the deal rather than how it could reshape the future of Brewers baseball, the second-most painful trade, behind the obvious potential dealing of Peralta, would be a trade of Milwaukee's 2025 closer, Trevor Megill. That's not to say that there doesn't exist a scenario where trading Megill makes sense, especially if Milwaukee is met with an overwhelming offer, but his departure would be just behind Peralta's in terms of viable trade candidates whose removal from the Brewers' 2026 roster would have the biggest impact on Milwaukee's ability to win a World Series next season.

Trading Trevor Megill during the Winter Meetings would be the second-most painful trade the Brewers could make next week, trailing only a potential Freddy Peralta deal

There are several reasons that the Brewers will consider moving Megill this offseason, and each of them holds merit. From the fact that Megill likely just pitched the best season of his career, to the fact that Abner Uribe appeared ready for the closer's role by season's end, to the fact that Megill is set to make a substantial salary in 2026 after a highly successful 2025 campaign, there exists a justification to move Megill this offseason. However, what the flame-throwing right-hander offers to the 2026 Brewers, a team that by all means should expect to compete for a World Series, is potentially more impactful than what he could bring in via trade.

For starters, even if Uribe does take over the closing duties in 2026, a decision that likely won't be made without giving Megill a shot, the Brewers would still have a need for Megill's services as one of the best set-up men in all of baseball. Megill led all pitchers with more than 40 innings of work in 2025 in Stuff+, a metric that assigns a score to each pitcher’s arsenal of pitches based on the velocity and movement of each of their offerings. With a Stuff+ score of 128, Megill was deemed to be a "nastier" pitcher than Jhoan Duran and Mason Montgomery, who were the centerpieces of blockbuster deadline deals last summer. So long as Megill's flexor strain, which he sustained during the final month of the regular season, is nothing to be too concerned about, there's no reason to believe that he won't be an effective reliever once again in 2026.

Therefore, moving him during the Winter Meetings, while it absolutely makes sense in some regards, would be detrimental to the Brewers' chances in 2026. The trade, while it could bring in MLB-ready players like the Devin Williams deal did an offseason ago, would likely be a forward-thinking move that once again prioritizes sustained success over a one-year splurge. For the patient Brewers fan, that might not be too painful to endure, but for those wanting a World Series title as soon as possible, it would be rather difficult to stomach.