Reporters, analysts and fans have big plans for the Boston Red Sox's 2025-26 offseason. Boston's return to the playoffs after three seasons watching from the couch has revealed some clear needs it must address before becoming a postseason regular again, and many of those additions could come at the Winter Meetings.
Starting on December 10, executives from around MLB, as well as potential trade and free agent candidates will convene in Orlando, Florida to start and finish off some negotiations. Red Sox chief baseball officer made his presence known at last year's meetings when he made the blockbuster of the week by trading for Garrett Crochet. He also acquired Carlos Narváez from the Yankees on the same day.
Both Crochet and Narváez exceeded expectations for the Sox last year, and the Red Sox have been linked to enough stars to make similarly impactful moves this year. The word 'dream' is doing a lot of heavy lifting for this roster, since it's unrealistic for Boston to make all these moves, but this Red Sox lineup would be tough for anyone to beat.
Dream 2026 Red Sox roster if Craig Breslow goes wild at the Winter Meetings
1B: Pete Alonso
2B: Marcelo Mayer
SS: Trevor Story
3B: Alex Bregman
RF: Wilyer Abreu
CF: Ceddanne Rafaela
LF: Roman Anthony
C: Carlos Narváez
DH: Kyle Schwarber
Bench/util: Romy Gonzalez
Bench: Triston Casas
Bench: Rob Refsnyder
Bench: Connor Wong
SP: Garrett Crochet
SP: Joe Ryan
SP: Freddy Peralta
SP: Sonny Gray
SP: Brayan Bello
RP: Aroldis Chapman
RP: Garrett Whitlock
RP: Pete Fairbanks
RP: Justin Slaten
RP: Greg Weissert
RP: Steven Matz
RP: Johan Oviedo
RP: Kyle Harrison
In our dreams, the Red Sox reunite with Bregman and bring Alonso in to round out the infield. Boston traded Rafael Devers to accommodate Bregman last year, and it shouldn't let that go so quickly. His swing is well suited to Fenway Park, despite his lackluster offensive second half of the 2025 season, and he still plays elite defense at the hot corner.
Alonso would add another righty bat to the order and supply the home run power the Sox are desperate to add. He's not a great defender at first base, but his durability is unmatched — he's never played fewer than 152 games in a full season in his seven-year career. A reunion with Rob Refsnyder would also up the righty presence, bring back a veteran and maintain a top-tier lefty masher.
On the subject of home run power, Schwarber would be an excellent addition to the DH spot. The Red Sox are well known to keep their DH spot flexible, but this is a dream roster, and Schwarber's National League-leading 56 home runs would absolutely be dreamy at Fenway Park.
The Sox have already added Gray and Johan Oviedo in trades, but in a dream world, they'd add two more starters — Ryan and Peralta. After the Oviedo trade, it's hard to imagine another pitcher trade happening this winter, let alone two, but Sox fans have already imagined Ryan or Peralta (or both) in the rotation. We slotted Oviedo in the bullpen here just to fit him in, but he's only pitched one full season of work in his career, and he pitched out of the bullpen in his final half-season with the Cardinals in 2022.
Boston's links to Ryan began before the 2025 trade deadline, and fans have been attached to the idea of bringing him in ever since. He has three years of team control on his contract, making him a more long-term investment and allowing the Sox time to potentially work out an extension.
Peralta is one of the most underrated elite pitchers in baseball, and he, Ryan, Gray and Crochet would easily make one of the strongest rotations in the league (subscription required). Unlike Ryan, Peralta would be a true rental on a one-year deal, making trading for him a true win-now move.
Whitlock and Chapman were possibly the most dangerous relief tandem in the American League, and adding Pete Fairbanks to the mix would create the "super bullpen" the Red Sox are rumored to pine after (subscription required). Reuniting with Steven Matz, who excelled in Boston after his transition to a full-time reliever, would add more lefties to the 'pen after the Sox traded three on November 18.
This Red Sox roster is unrealistic, to say the least, especially after the latest rumors on the team's payroll goals. But this Boston squad, reinforced with multiple elite pitchers in the rotation and bullpen along with home run power to go around, is absolutely worth dreaming about.