After a half decade's worth of underwhelming offseason acquisitions, the Boston Red Sox returned to a big market level of spending in 2025. Craig Breslow's savvy moves helped propel Boston back to the postseason, but just appearing in October is not the end goal.
The Red Sox have a solid few deficiencies to addres on their roster before they'll be able to pull off a longer playoff run. They lacked power in their offense and their rotation ran out of steam (and healthy options) in the final stretch. It could take some big signings and blockbuster trades to address their issues, and not every fan is confident they'll take the necessary risks to acquire such talent.
Red Sox insider Alex Speier of The Boston Globe seems to have faith in the front office, however. The reporter appeared on the October 22 episode of the "Sox Prospects" podcast to discuss Boston's offseason needs and how it could go about addressing them. He noted a distinct change in Breslow's postseason verbiage from 2024 to 2025, which went from a need to improve without mortgaging the future to a need to improve the 2026 team by any means necessary.
“I would be really surprised if the Red Sox had a run-it-back offseason. I would be pretty surprised if they had a... looking to just move food around the plate offseason," Speier said. "I think that there are going to be some big swings again in this offseason, potentially measured by the end of the collective bargaining agreement.”
The Red Sox could take "big swings" in many ways this offseason, from more blockbuster trades to pricey free agent deals. The free agent signing they should prioritize most is a reunion with Alex Bregman.
Red Sox insider Alex Speier sees 'big swings' coming from Red Sox front office this offseason
Bregman opted out of the final two years of his original deal with Boston to seek a longer-term contract this offseason — he hopes to sign with a team he can play the rest of his career with. The Red Sox can, and should, be that team after trading Rafael Devers away and seeing the impact of Bregman's rock-solid all-around play and leadership in the clubhouse.
The Sox also need a jolt of power in their lineup, and a reunion with 2021 fan-favorite Kyle Schwarber could be just the shot in the arm they're looking for. Schwarber crushed a career-high 56 home runs and 132 RBI in 2025, and he could quickly resolve Boston's power outage and troubles with runners in scoring position. It would also be able to land him for a lower price and on a shorter-term deal than Pete Alonso due to his position and age. The Red Sox like to keep their DH spot flexible, but signing Schwarber and changing their method sounds like a risk worth taking.
Boston could also take a big swing on the trade market, which is expected to feature multiple elite starters this winter. The Red Sox have been linked to or named as a possible landing spot for Joe Ryan, Tarik Skubal, Freddy Peralta and Hunter Greene. Each of these players would require a massive trade package, and some options are more attainable and worth the risk than others.
A deal for Skubal would be the riskiest of them all. The 2024 Cy Young Award winner (who's about to win another) would warrant an insane trade package of multiple top prospects and big league talent, but his proximity to free agency is the real risk. Skubal is represented by agent Scott Boras, and he discourages his clients from signing extensions before seeing what the free agent market has to offer, and Skubal is more than likely in line to become the highest paid pitcher of all time next winter.
A trade for Ryan or Peralta would make more sense. Not only is Skubal another undeniable ace the Red Sox don't need since they have Garrett Crochet in their No. 1 spot, Ryan has more years of control remaining on his contract that Boston could use to get him to sign an extension. Peralta is also one year removed from free agency, but he isn't the same caliber of pitcher as Skubal, so he'll be available at a lower, less-risky price (although, not much lower, as he's still an elite arm).
The Red Sox have plenty of money and an elite farm system to use to improve their 2026 squad this offseason, and by many accounts, Breslow has big moves on his radar. Boston has let itself be outbid for major free agents and held onto top prospects in recent years — we'll see if it fully embraces its competitive window this winter.