Now almost three weeks removed from being swept out of the wild card round by the New York Yankees, the Boston Red Sox are fully in offseason mode as they look to build a true World Series contender for the 2027 season. However, a looming black cloud hangs over the first month of the offseason, and the 2027 season as a whole, in the form of a seemingly imminent lockout when the current collective bargaining agreement expires at 11:59 p.m. ET on Dec. 1. 

Chief Baseball Officer Craig Breslow and team president Sam Kennedy have been asked about the lockout multiple times, most recently at the team's annual end-of-season press conference on Oct. 5. "I'll put whatever CBA situation aside; it's not really my place to talk through. What I'll say is every offseason is unique; we've seen certain offseasons where free agents sign early, others where it drags out, where there's a flurry of trade activity early, others where significant trades take place after the new year. It's hard to pinpoint how the natural sequence of the offseason will go this year," Breslow said when asked about how the labor situation would impact the offseason.

While Kennedy brushed aside concerns of a lockout as being above his pay grade, saying, "The good news is that labor issues are way above our pay grade. We're moving forward with business as usual as we get into the rest of October, November, December, and January. We'll leave the labor stuff to the Commissioner's Office."

Unfortunately for both Breslow and Kennedy, the team simply cannot look past the lockout and operate business as usual heading into the offseason. The labor dispute between the owners and the MLB Players Association affects the sport's entire economic landscape, with a salary cap and floor system at the heart of the negotiations. 

As Breslow and the rest of the Red Sox front office plan for the offseason ahead of the postseason's conclusion, they'll have to decide which route to take before the lockout: be aggressive and make moves ahead of a lockout, or wait it out and see how the landscape of the sport looks at its conclusion.

Of course, the team will need to make some moves before the lockout begins on Dec. 1. It will have to clear four spots on its 40-man roster to make room for players who ended the season on the injured list. They will also have to begin negotiations with arbitration-eligible players and make some roster decisions ahead of the non-tender deadline on Nov. 20. 

Then there's free agency, which officially opens five days after the World Series concludes. Of course, players will largely dictate free agency. Will free agents look to lock in their contracts ahead of the lockout and secure their money and new homes ahead of a potential new salary cap landscape? Or will they wait things out in hopes that more teams will be willing to open up the checkbooks after the lockout's conclusion and (if the players get their way) no threat of a salary cap looming? 

It seems more likely that the bigger-name free agents like Tarik Skubal, Randy Arozarena, and Freddy Peralta, just to name three, will wait things out in hopes of landing a bigger deal in a non-capped environment. However, role players may opt to lock in their deals while they can. 

While free agency remains up in the air, there figures to be plenty of trade movement ahead of the lockout. The Red Sox were incredibly aggressive ahead of the trade deadline, making two major moves and landing infielder Curtis Mead and catcher Adley Rutschman. One area the Red Sox pursued but didn't move on ahead of the deadline was a long-term answer at shortstop. Could Breslow revisit those discussions to lock in a major upgrade before the lockout, and use free agency to supplement a team that is almost complete and heading into the lockout with an almost finished product? 

Ultimately, though, Breslow is right. The rest of the league will have to set the offseason's cadence. The Red Sox could be the most eager team in the world to make major moves ahead of the lockout, but if the rest of the sport seems determined to wait, they may have no choice.

At least in regard to signing free agents, this seems like the most likely approach the Red Sox and the rest of the league will take. No head of baseball operations will want to lock their team into a deal at market value before the lockout, only for it to become an albatross in a capped environment. And no owner will want to shell out major money to land a free agent just weeks before joining a collective front to institute a salary cap. 

While there could be some movement on the trade front ahead of the lockout, taking a more cautious approach could also create new opportunities. Whether or not there's a salary cap and floor, the sport's economic landscape will change. Whether through increased luxury tax penalties, changes in how contracts are structured, or how money is deferred. 

If the owners do get their way and a cap and floor system is established, teams that are significantly over the cap could look to move quality players to get under the limit, while teams that are spending way below the floor could look to take on bad contracts in order to accumulate enough salary to reach it. If the luxury tax penalties increase to put more pressure on heavy-spending teams, you may see a similar push to shed big-money contracts for quality players. 

Given that the Red Sox find themselves between a rock and a hard place with their payroll expected to exceed the second luxury tax threshold for the third season in a row, a cautious approach seems like the most likely path for Boston to take, at least in terms of adding major dollars to the roster. 

Regardless, we should have a pretty clear idea of how passive or aggressive teams will play in the first week or two of the offseason officially beginning. 

Looking for more on the Red Sox needs heading into the offseason? Zach Coe and David Azer are back on the 'Entering Kenmore' Podcast discussing how close Boston is to winning a World Series, whether the 2026 season was a success, and whether fans should have faith in Craig Breslow's ability to build a World Series contender. Check it out wherever you get your podcasts, or in the YouTube player below: