Despite being well into the offseason, December marks one of the busiest times of the year for Major League Baseball. The Winter Meetings took place this past week, where all 30 organizations and their front offices traveled to Orlando to meet with each other along with free agents. Many teams made moves to improve their rosters, but the Red Sox were quiet during the week, letting several targets slip away and sign with other organizations. For President of Baseball Operations Craig Breslow, there are still many problems to solve before Spring Training.
After a 4-0 loss to the New York Yankees in Game 3 of the AL Wild Card series ended the 2025 season for the Red Sox, fans were left with many more questions than answers. The 2025 campaign was a rollercoaster for the team, which included trading away superstar slugger Rafael Devers, a 10-game win streak, Outfielder Roman Anthony’s breakout as a future face of the franchise, and the team’s first Postseason appearance since 2021.
Despite making it to the playoffs, injuries to Anthony, First Baseman Triston Casas, and Starter Lucas Giolito left the Red Sox unable to keep up with the Yankees for three games. Giolito’s injury forced 23-year old Connelly Early into making just his fifth big league start in Game 3, where he struggled, giving up three earned runs and being pulled after less than four innings.
The series exposed the biggest holes in the team’s roster at the time, the main ones being the lack of a #2 Starter to complement Garrett Crochet and the absence of a true everyday power bat after dealing Devers to San Francisco. Shortly after the series, Third Baseman Alex Bregman opted out of the remaining two years of his 3-year, $120 million contract, leaving another hole in an already questionable infield.
The only infielder from last season expected to be in the team’s Opening Day lineup in 2026 at the moment is Shortstop Trevor Story, after he opted in to the remainder of the 6-year, $140 million contract he signed before the 2022 season on November 4th. After playing just 163 games in the first three seasons of his contract, Story played in 157 in 2025 and became one of the biggest offensive contributors to the team down the stretch after a slow start to the year.
At the catcher position, the Sox are expected to return both of their big leaguers in Carlos Narváez and Connor Wong. After struggling to move through the Yankees organization and only playing 6 games for the major league club, Narváez was acquired by the Red Sox on December 11, 2024, where he blossomed, becoming one of the leaders of the team and the catcher of the future. In his rookie season, he finished with a Statcast Run Value of 12, and was a Gold Glove finalist while being solid offensively.
Wong, on the other hand, struggled immensely in 2025, dealing with a nagging hand injury, which he had surgery for on October 9th. Offensively, he batted just .190, had an OPS+ 58 points below league average, and didn’t record an extra-base hit until late July despite playing regularly leading up to that point. Defensively, he made 5 errors and finished with a Statcast Run Value of -3. He is expected to be healthy for Opening Day.
In the outfield, Roman Anthony and Ceddane Rafaela are both expected to return. Rafaela won the Center Field position in Spring Training, and has since developed into one of the best fielders in the sport, winning a Gold Glove this season and finishing 3rd in the majors across all positions with a Statcast Run Value of 22. Offensively, things were not as smooth. He went into the All-Star break batting .271 with 14 home runs and an OPS of nearly .800, but he came down crashing hard in the second half, batting .218 with a .587 OPS and only hitting 2 home runs.
Roman Anthony was called up from AAA Worcester on June 9, and it only took him a month to establish himself as the future face of the franchise post-Devers. Despite suffering an Oblique strain in early September and finishing the season on the IL, Anthony put up 8 home runs and an .859 OPS in his 71-game Rookie campaign. On the defensive side, he spent time in both corner outfield spots, putting up 6 Outs Above Average in both Right and Left Field.
Jarren Duran and Wilyer Abreu both played regularly in the team’s outfield in 2025, but both players have been heavily involved in trade rumors due to the team’s surplus of outfielders and their struggles against left-handed pitching. Duran had a down year in 2025 after finishing 8th in AL MVP voting in 2024. Offensively, he put up a solid .774 OPS in 157 games, but his defense regressed from his 2024 campaign where he was a Gold Glove Finalist in Center Field. Duran lost the CF position to Ceddanne Rafaela in Spring Training, and was forced to switch to Left Field full-time, where he struggled to make reads on balls and finished the year with an OAA of -5 at the position.
For defense, the same cannot be said for Wilyer Abreu, who won his second consecutive Gold Glove and had the second-highest OAA in the Majors for Right Fielders with 11. He also put up a .786 OPS and hit 22 Home Runs in 115 games, although his performance declined severely after he returned from a Calf Strain he suffered in mid-August that sidelined him for over a month. The team was reluctant to play him against left-handed pitching in 2025, although that will change in 2026 if he isn’t dealt, per Manager Alex Cora.
For Duran and Abreu, there isn’t a clear-cut answer as for which to keep and which to trade. Both players have been given a “50% chance” of being traded by Jeff Passan of ESPN. The Red Sox value both players highly, and a trade would have to start with an MLB-ready starter along with other assets. Passan identified the Tigers, Royals, and Giants as trade partners for both players. Neither player has hit well against lefties in their career, although Abreu has not yet had an opportunity to while Duran has.
Duran profiles as the more well-rounded player offensively, with him spreading out his offensive production more than Abreu. His speed on the bases is his best attribute, with him finishing top-2 in triples and stealing more than 20 bases in consecutive years. His defensive struggles are a cause for concern, with the lack of flexibility in his defensive position potentially diminishing his value slightly compared to Abreu. Many of his redeeming defensive qualities such as his arm can be attributed to the Green Monster and short Left Field at Fenway, and a trade would likely result in a regression in those categories. He is 29 and has three seasons of team control remaining.
Abreu is a pure power hitter that mainly hits doubles and home runs, and he gets on-base less frequently than Duran and struggles against velocity. His fielding is his main skill, but Roman Anthony’s short success in Right Field and his unproven status as an everyday player has made fans question the true value of his glove to the team. He is 26 and has four seasons of team control remaining.
For Craig Breslow, the deal will likely come down to whoever gets the better offer in return. Both players fit well in Boston’s outfield, so Breslow’s most likely option is to take the better offer and give the third outfield spot to the remaining player of the two. There’s also a possibility that both players get moved, with Kristian Campbell being designated as an outfielder for the long-term, as well as the off-chance Breslow signs Kyle Tucker or makes a blockbuster trade.
The Red Sox are expected to continue utilizing platoons in 2026, which have become a staple of Alex Cora’s lineups during his tenure. The Red Sox had the seventh-highest team OPS in the Majors against left-handed pitching, mostly due to “lefty-killers” Romy González and Rob Refsnyder. González has four years of team control remaining, and is expected back with the team as a utility infielder. Refsnyder is currently a free agent, but there have been talks for him to return to the club in 2026.
After the Devers experiment at Designated-hitter failed, Cora was put in a predicament with the position. On most days, the position was either filled by one of the outfielders or Masataka Yoshida after he returned from shoulder surgery in early July. The Red Sox were expected to target a full-time DH in Free Agency, but after Kyle Schwarber inked a 5-year, $150 million extension in Philadelphia on Tuesday, those talks were seemingly put to rest.
The team is expected to take the same flexible approach at the position next season as they have in previous years. Some returning options include Yoshida, Triston Casas, and Kristian Campbell. It’s unlikely any external options will be considered unless a trade is made between now and Opening Day.
The same can be said for First Base after Pete Alonso signed a 5-year contract worth $155 million on Thursday. The Red Sox struggled to find an everyday player at the position in 2025 after Casas went down for the season in April, looking to Abraham Toro, Romy González, and Nathaniel Lowe as temporary replacements. Toro played very well in May and June, but he quickly cooled off and was one of the worst hitters in the sport before being Designated for Assignment in August. His replacement, Lowe, was mediocre in his short stint with the team and was Non-Tendered after the season ended.
Triston Casas is an option, but his unreliability and poor defense make him more likely to play at DH if an opportunity even comes for him to play for the Red Sox next season. Romy González will likely spend time there in a platoon role, and could take an everyday role if needed. There are also some external options in Eugenio Suárez and Kazuma Okamoto of NPB’s Yomiuri Giants, although Breslow has shown no real interest in either yet.
Marcelo Mayer is expected to play Second Base next season, although it is unknown if he will take on an everyday role or a more controlled platoon role like he did in 2025. Mayer played well defensively at both second and third base last season, but he struggled offensively, posting a .228 average with a .674 OPS in 44 games before having season-ending wrist surgery in August. Mayer is another player with durability concerns, as the 2021 4th-overall pick is yet to play more than 91 games in a season in his professional career.
Second Baseman Ketel Marte has recently been subject to heavy trade rumors, with the Red Sox reportedly exploring the option of acquiring him. Despite his age, Marte would be a needle-mover for the team both offensively and defensively. He has finished 7th in the majors in back-to-back seasons in OPS, and his career Statcast run value of 8 would be a large upgrade to an infield defense that desperately needs support. A Marte trade would likely include Mayer and one of the team’s top pitching prospects.
HHS student Matthew Volpe thinks very highly of Marte, saying, “I would love to see the Red Sox acquire [him] ,” when asked who he wanted the team to acquire this offseason. “He has great offensive ability, and his leadership skills could provide some security with the Jarren Duran trade rumors.”
A Duran trade, along with a potential Alex Bregman exit could bring into question the identity of the team in 2026. Duran, Bregman, and Trevor Story were the team’s three biggest leaders throughout 2025, and they were one of the biggest reasons why they were able to power through the obstacles that they encountered throughout the year. While losing either of them would be a large loss, let alone both, Marte could take control of the clubhouse and help mentor a group filled with young players.
Fans have identified Starting Pitching as the biggest need for Craig Breslow to address in the offseason. While they have very good young starter depth with players like Payton Tolle, Connelly Early, and Kyle Harrison, the lack of a true #2 behind Garrett Crochet at the top of the rotation is one of the main reasons the Red Sox lost the Wild Card series to the Yankees.
The Red Sox acquired Sonny Gray in a trade with the Cardinals on November 25th that sent Richard Fitts and Brandon Clarke to St. Louis. Gray is 36, and it is unclear whether he will fill the #2 or #4 role for Boston in 2026. He had a high 4.28 ERA in 2025, but a 3.39 FIP suggests that bad luck had more to do with his results rather than poor performance.
Even after acquiring Gray, the Red Sox are still in the trade market for a SP. Some of the options include Freddy Peralta, Tarik Skubal, and Joe Ryan. The Red Sox almost traded for Ryan at the deadline last season, but were unable to get the deal across the finish line in time due to Breslow being unwilling to part with any Major League talent at the time, instead settling on Dustin May, who didn’t work out in his short stint with Boston. Since then, the Twins have declared Ryan as untouchable, and it is unlikely the Red Sox will approach them again.
For HHS student and Baseball captain Casey Joseph, the answer is clear: “I think the Red Sox should trade for Freddy Peralta. I really like his Changeup, and he’s definitely worth extending in my opinion.”
Peralta, 29, has heard his name quite a bit in trade rumors recently after a report that the Brewers did not want to extend him surfaced. He ranked in the 96th percentile for Run Value on Offspeed pitches last season. Some work in Andrew Bailey’s pitching lab could turn him into a perennial Cy Young candidate after he posted an elite 2.70 ERA in 2025, and a trade should be less expensive compared to other pitchers due to him only having one year remaining on his contract with Milwaukee.
Skubal is the reigning back-to-back AL Cy Young Winner, and the Red Sox made some calls to inquire about him after a report came out that stated he and the Tigers were nearly $250 million off on an extension. While it’s unlikely that anything comes of it and it would take an absolute haul for Detroit to even consider it, it’s still worth mentioning, and having the two best pitchers in Skubal and Crochet in the same rotation would be incredibly entertaining to watch.
In the back of the rotation, Connelly Early, Hunter Dobbins, Kutter Crawford, Patrick Sandoval, and Payton Tolle, along with newly-acquired Johan Oviedo are all expected to compete for a spot in Spring Training.
Sandoval, Crawford and Dobbins all suffered injuries that resulted in them missing the majority of 2025, with Crawford and Sandoval missing all of it. Early impressed in his few starts with the Red Sox in 2025, where he had a 2.33 ERA in four regular season starts. He is the most likely to make the rotation out of Spring Training out of that group.
Tolle quickly rose through the ranks in the Red Sox organization in his first full pro season, but he proved to not quite be ready as he didn’t have the secondary pitches to support his fastball, leading to it being the only pitch he threw at times, which opposing players picked up on quickly. Oviedo made 9 starts with the Pirates in 2025, where he put up a solid 3.57 ERA.
For the bullpen, not much is changing. Star Closer Aroldis Chapman is returning after having one of the best seasons in recent memory for the Red Sox, where he had a 1.17 ERA in 67 appearances and held the 3rd-longest hitless streak for any MLB pitcher since 1901. High leverage righty Garrett Whitlock is returning after also having an excellent 2025 where he finished with a 2.25 ERA.
Greg Weissert, Justin Slaten, and Zack Kelly are all also set to return, all of whom were key contributors to the team’s second-best bullpen ERA in the majors. Jordan Hicks, who was acquired in the Devers trade, is also returning after struggling in 2025.
The Red Sox have a bright future ahead of them. But work needs to be done to the current roster, and in its current state, the team likely will not improve much in 2026. However, with the right moves, the Red Sox have the potential to be World Series contenders for this year and beyond.
