Will Brewers’ typical Winter Meetings strategy carry over to GM Meetings this year?

Major League Baseball has embarked on what is going to be a modified 2026-27 offseason. The league is all but guaranteed to enter a work stoppage on the night of December 1, as they continue to negotiate a new Collective Bargaining Agreement with the MLB Players' Association. During said work stoppage, also referred to as a lockout, teams won't be able to sign free agents, negotiate trades with one another, or modify their rosters for the 2027 season. As a result, teams are preparing for a busy month of November in hopes of finalizing their roster before the uncertainty of the lockout and the new CBA sets in.

Another casualty of MLB's looming lockout are the Winter Meetings. Scheduled for the first week of December, the Winter Meetings typically serve as an opportunity for front office executives, agents, players, and the media to converse and set the offseason in motion. However, with this year's Winter Meetings scheduled to take place from December 7-9, just one week after the work stoppage is expected to begin, it's all but certain they will be canceled.

Interestingly enough, MLB always hosts another set of offseason meetings called the "GM Meetings" four weeks before the Winter Meetings. The GM Meetings, which technically began yesterday in Las Vegas, typically don't produce as many transactions as the Winter Meetings, in part because they are so much earlier in the offseason. However, with MLB's offseason expected to be accelerated by the upcoming lockout and the Winter Meetings set to be canceled, there's a belief that the GM Meetings will replace the Winter Meetings and produce a level of activity that is atypical for this time of year.

The Milwaukee Brewers have frequently made use of the Winter Meetings to lay the groundwork for offseason trades, begging the question 'will this typical negotiating strategy carry over to the GM Meetings this year?'

Brewers' typical trade strategy suggests early-offseason deal could come in wake of GM Meetings

In each of the four offseasons since MLB's last lockout canceled the 2021 Winter Meetings, the Brewers have executed a trade in the immediate aftermath of the Winter Meetings. Last year, they traded Nick Mears and Isaac Collins to the Kansas City Royals on December 14. In 2024, the Brewers sent Devin Williams to the New York Yankees in exchange for Caleb Durbin and Nestor Cortes on December 13. The year prior, Milwaukee traded for right-hander Taylor Clarke from the Kansas City Royals shortly after the Winter Meetings and executed the Tyrone Taylor and Adrian Houser for Coleman Crow deal with the New York Mets the following week. And back in 2022, the William Contreras three-team blockbuster went down on December 12, five days after the Winter Meetings concluded.

Clearly, the Brewers have used the Winter Meetings as an opportunity to negotiate with other front offices and get deals close to the finish line before finalizing them shortly thereafter. But without any Winter Meetings this year, will the Brewers apply that same strategy to this week's GM Meetings? It's certainly plausible, especially considering the Brewers have several trade candidates they must make decisions on before the work stoppage arrives.

The most likely trade that Matt Arnold and company may be discussing at the GM Meetings is one that sends impending free agent closer Trevor Megill elsewhere. The Brewers have traded four All-Star pitchers in the last four years -- a strategy that was key to their construction of a World Series-caliber roster. Reportedly, they are looking to continue that trend by dealing Megill this offseason, but are challenged by needing to see how the reliever market materializes before doing so. For example, whether or not the New York Yankees are interested in trading for Megill hinges on David Bednar's qualifying offer and subsequent free agency decision.

The Brewers await a qualifying offer decision of their own, with Jake Bauers currently mulling over whether or not to accept the one-year, $23.15 million contract. Should Bauers accept, Andrew Vaughn, who will be a free agent after the season, could emerge as the topic of Brewers trade talks in the coming weeks as well. Milwaukee is reportedly not interested in trading World Series MVP William Contreras this offseason, despite the All-Star catcher entering his final year of team control. The Brewers did the same with Willy Adames back in 2024 before he departed for the San Francisco Giants in free agency.

There's certainly a greater significance placed on this year's GM Meetings due to the anticipated cancellation of the Winter Meetings. Whether or not that means the Brewers' will apply their typical trade negotiation strategy from the Winter Meetings to the GM Meetings remains to be seen, but it certainly wouldn't come as a surprise to see Megill moved in the wake of this week's meeting of front office executives.

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