Many decisions await the Boston Red Sox this winter, with key needs at several spots on the roster and some integral pieces hitting the open market. How the team attacks the process will go a long way in terms of determining their success in 2026.
To that end, we're here to take a look at what may lie ahead and make some predictions for how things may play out. These might not be the most likely outcomes, but they are daring and all within the realm of possibility. Some may delight Red Sox fans, while others may leave you feeling depressed. Such is life for a Red Sox fan.
3 bold Red Sox offseason predictions to both delight and disappoint fans
Alex Bregman re-signs with the Red Sox for less than expected
Alex Bregman opting out of his contract was a mere formality, but while he's expected to have a more robust market than he did last winter, there's reason to believe that might not be the case.
Of the rumored suitors, many may find options that better fit their budgets and team dynamics. For instance, Detroit Tigers boss Scott Harris has not so subtly hinted that his top prospects will have big roles in 2026, and baseball's No. 2 overall prospect Kevin McGonigle is currently working on his defense at the hot corner in the Arizona Fall League.
Elsewhere, the Mets will be preoccupied with Pete Alonso and fixing their starting rotation. The Dodgers might decide that Max Muncy's playoff prowess and ridiculously affordable $10 million option are a better plan for 2026. The Seattle Mariners might find retaining Eugenio Suárez more budget-friendly, and the Houston Astros' reunion with Carlos Correa closes the door on Bregman bolting back there.
On top of that, another factor stands between Bregman and his lofty contract demands: the expiration of the current Collective Bargaining Agreement next December. The negotiations for a new CBA are expected to be contentious, and uncertainty regarding the luxury tax and/or salary cap structure could depress salaries. Of greater concern for Bregman, the threat of a lockout could cause every team that signs him to pause, considering the fact that they may lose a year of his waning prime.
Ultimately, when the music stops, Bregman and the Red Sox will only have eyes for each other. He's clearly Boston's best option, and he enjoyed his time here. A depressed market brings him back at a discount.
The Red Sox trade for another ace and it won't be Tarik Skubal
The Red Sox are considered by some to be the team with one of the best chances to land Tarik Skubal. For good reason, too. They have a collection of MLB-ready prospects and young players that fill holes for the Tigers without decimating the farm system.
However, it's not just the acquisition cost for the generational ace that matters, but also the massive dollar amount necessary to get an extension done. Boston no longer has Rafael Devers' contract on the books, but John Henry has been wishy-washy about spending big in recent years.
The Red Sox's priority recently has been locking up their young core as early as possible, indicating their desire to keep payroll manageable. That doesn't mean they won't spend at all, but a record-setting deal for Skubal might not be in the cards.
Two alternatives stand out — Freddy Peralta of the Milwaukee Brewers and Hunter Greene of the Cincinnati Reds. Peralta would require an extension or else be a one-year rental, while Greene is already signed to a relatively cheap deal that runs through 2028 with a club option for 2029 that comes in at $21 million.
Big picture, the Red Sox need to think about the state of the rotation as a whole. Garrett Crochet leads the way, but Brayan Bello's playoff start highlighted some cracks that make him a questionable No. 2. Lucas Giolitio isn't entirely trustworthy either. Beyond those two, Connelly Early deserves a spot, Payton Tolle needs more seasoning, and who knows what you're going to get from Kutter Crawford and Patrick Sandoval, as both come back from serious injuries and have dealt with inconsistencies in the past.
Peralta or Greene would come much cheaper and slot in well as the second part of a one-two punch atop the rotation. Or, the Red Sox could really go crazy and trade for both. The cost in terms of prospects and dollars would be roughly equivalent to Skubal alone.
More realistically, only one arrives in Boston, but for those dreaming of a super rotation, it could be built without Skubal.
The Red Sox will trade Marcelo Mayer
This one ties in to the first two. If Bregman comes back, the pathway for regular at-bats for Marcelo Mayer gets complicated. While second base is a possibility for Mayer, the full outfield might push Ceddanne Rafaela to the keystone more often in 2026.
Combine that with the potential trade for an ace, and Mayer will be a player that many of these clubs might ask for. Keep in mind, the Tigers (Skubal), Brewers (Peralta), and Reds (Greene) are all looking to contend despite the prospect of trading their aces.
As a result, all three of those clubs will be on the prowl for major-league-ready talent. Furthermore, Mayer would fit Detroit's roster like a glove, while the Brewers could turn Caleb Durbin into a super-utility man and slot Mayer in at the hot corner. For the Reds, more moving parts would be required, but they could do what seems inevitable and move Elly De La Cruz to center, opening up shortstop for Mayer.
Given the state of the trade market, it seems that everyone will be asking for Mayer, and Boston won't be able to make a move without him headlining the trade package.