The 2026 and 2027 Major League Baseball offseason has officially begun, albeit under a cloud of uncertainty. The primary driver of this unease is the ongoing collective bargaining agreement negotiations between the league and its players. There is a near certainty that an owner implemented lockout will commence on December 2 if a new deal is not reached. This looming deadline casts a shadow over all current activities, mirroring the atmosphere that preceded the previous lockout in the 2021 and 2022 season.
Due to the prospect of a hastened pace, offseason rumors have already begun to circulate widely. The expectation is that a significant level of activity on both the trade and free agency fronts will occur before the lockout begins in early December. This pattern aligns with what was observed leading up to the last work stoppage. However, this time around, the potential for drastic changes in the next collective bargaining agreement may prompt teams with large budgets to fortify their rosters before those changes are implemented.
MLB Network reports that notable transactions could take place at the upcoming General Managers Meetings, which are scheduled to run from November 10 to 12 in Las Vegas. In a typical offseason, these meetings are primarily used for behind the scenes groundwork, with the major moves usually reserved for the December Winter Meetings. However, unless the current lockout is resolved quickly, which is considered highly unlikely, there probably will not be a Winter Meetings this year. Consequently, the GM Meetings are expected to be more active than usual.
Amidst this shifting landscape, free agent ace Tarik Skubal remains the most prominent figure in the market. The 29 year old left handed pitcher, who was the reigning back to back American League Cy Young winner until later this week, is considered a fit for any of the 30 teams in Major League Baseball. Until recently, the most serious bidders for his services were expected to be the Los Angeles Dodgers, the New York Mets, and the Chicago Cubs. The Dodgers notably acquired Skubal from the Detroit Tigers leading up to last season's trade deadline.
However, the field of serious contenders for Skubal may now be reduced to just two teams. Reports from The Athletic indicate that the Chicago Cubs are expected to stay on the sidelines when the bidding for the ace gets serious. This development comes as a surprise to many, given the team's clear need for rotation help for the 2027 season and beyond. The decision reflects a strategic choice to wait rather than engage in a high stakes bidding war under the current uncertain conditions.
For Cubs fans, this news is likely to be disappointing. Many supporters have been waiting for the Ricketts family, the team's ownership group, to invest in the payroll at levels that befit a big market contender. The decision to sit out the Skubal pursuit suggests a cautious approach to spending as the team navigates the complexities of the impending lockout and the potential changes in labor rules. The market for other position players and pitchers will likely see a realignment as teams adjust their strategies in response to the Cubs' move.
The lack of a Winter Meetings this offseason means that the November GM Meetings in Las Vegas will carry significantly more weight. Teams that are looking to make moves must do so now, as the window for negotiation before the lockout closes is narrow. This compressed timeline could lead to accelerated decision making and potentially more aggressive offers from teams willing to invest heavily before the rules change. The coming days will be crucial in determining the shape of many rosters for the next season.
As the baseball world watches the negotiations closely, the focus remains on how quickly a deal can be struck. If the lockout proceeds as anticipated on December 2, the lack of a Winter Meetings will leave a gap in the traditional offseason calendar. This unusual circumstance is forcing teams to adapt their usual timelines, making the current period one of the most active and unpredictable in recent memory. The outcome of these early moves will set the tone for the remainder of the offseason and the upcoming season.
