The Boston Red Sox were back to playing October baseball in 2025, which was a big step in the right direction for the franchise after missing the postseason the last three years. While the Boston brass is celebrating that return, it’s also promising not to get complacent this winter.
A return to the playoffs was nice, but that’s not the ultimate goal in Boston. The goal is to add World Series banners, and the Red Sox came up short this October. The optimism around the team is only giving more fuel to manager Alex Cora and chief baseball officer Craig Breslow, who are gearing up for another big winter to push the organization into becoming a true World Series contender.
“I think we’ll be playing for the same thing next year; to win the AL East, have a deep run in October, and hopefully win the World Series,” Cora said Monday at the team’s season-ended press conference at Fenway Park.
Cora said he’s heard from a number of players — including young Boston players who were hurt for the playoff run — who are all eager to attack the offseason hard to put them in the best position to take that next step in 2026. The front office is going to follow suit this winter.
The Red Sox had an aggressive offseason last winter, which sparked the team’s return to the postseason. Breslow parted ways with some of the organization’s top prospects to land ace Garrett Crochet, who was the stud at the front of the rotation the Red Sox have needed. Breslow also signed veteran closer Aroldis Chapman, who had a renaissance season and was one of the most dominant closers in the game. He also signed Alex Bregman to be a big bat for the top of the lineup and a vocal leader in the clubhouse, and the veteran worked wonders for the young players the Red Sox integrated throughout the 2025 season.
While the Red Sox were able to end their playoff draught and won Game 1 of the Wild Card round against the Yankees in New York, Boston’s postseason run ended with back-to-back losses to their biggest rival. While there is a lot of good to take from the 2025, there is also an important lesson to guide the brass through this offseason.
“The most significant of which is to remind ourselves there is no guarantee we pick up where we left off at the end of 2025. Expecting everyone to take a step forward could cause us to he complacent and fall flat,” Breslow told reporters Monday.
The Red Sox got complacent after making a run to the ALCS in 2021, and then suffered through three October-less seasons. The franchise cannot afford to take a similar path after losing in the Wild Card round in 2025.
Breslow didn’t want to get into the details of the organization’s offseason plan, but the team is going to once again get aggressive to try to return to the upper echelon of title contention.
“We’ll be open to all possible pathways to improve the team,” said Breslow. “There are a number of ways to improve the club and we’ve demonstrated a willingness to attack those. I think we will again this offseason.”
Red Sox will look to add more pitching in offseason
“When we talk about pursuing opportunity to improve the team, bringing in pitching is certainly one of them,” Breslow said Monday.
Breslow admitted to stating the obvious a bit, because everyone in baseball is always looking to add more pitching. But more is clearly needed after Crochet was the only reliable arm in the rotation come October.
Brayan Bello and Lucas Giolito were solid behind Crochet during the regular season, but Bello faltered in the playoffs and Giolito was lost to an elbow injury just ahead of the postseason. Frambler Valdez, Chris Bassitt, Dylan Cease, and Zac Gallon are a few of the upcoming free agent pitchers Boston could pursue, and Breslow could always kick the tires on a Joe Ryan trade with the Twins after he came up short for the Minnesota ace at the trade deadline.
Breslow is pleased with the organizational pitching depth with guys like Connelly Early, Payton Tolle, and Kyle Harrison in the mix to start games in 2026. But they could just as easily be used in a trade package for more established pitching.
“I think we feel good about the farm system and the depth we have, the young talent,” said Breslow. “I don’t think this is an either/or outcome. We want to have a winner in the Major Leagues while also maintaining a healthy farm system.
“Everything has to be on the table as we look to improve the team in 2026,” he added.
Do the Red Sox have too many outfielders?
The Red Sox are stacked in the outfield with star prospect Roman Anthony, Jarren Duran, Ceddanne Rafaela, and Wilyer Abreu atop the depth chart. But that logjam forced Cora to play some musical chairs during the regular season, though the depth was valuable when Anthony went down in August with an oblique injury.
Cora also said he’s up to the task of cycling through his four outfielders if needed for a full season.
“If I have four, I can manage them. You find ways and at the end of the day, the deeper the better,” said Cora. “That’s something we had tested at the end of the season. We can’t control injuries and can’t control slumps. As far as managing, yeah, you can do it.”
The Red Sox have an $8 million club option on Duran, who struggled in 2025 after his All-Star campaign in 2024. Breslow wouldn’t share his thoughts on Duran’s option, but he did speak glowingly about the outfielder.
“I’m not ready to speak specifically about players or contract situations. But we’ve seen what Jarren means to this team and we’re glad he wears a Red Sox uniform,” said Breslow.
Red Sox looking to improve their defense
There is no sugar-coating Boston’s defense in 2025. It was the worst in baseball, with the Red Sox leading everyone with 116 errors and sitting last in the Majors with a .980 fielding percentage. In the playoffs, the Red Sox were burned when a pair of catchable fly balls ended up hitting the turf in Yankee Stadium. Each of those outfield miscues tied in directly to losses in Games 2 and 3.
Something clearly needs to change on the defensive front for Boston.
“We made errors, but we were a lot better,” Cora said of the defense as a whole. “There were a lot of things we didn’t do early in the season, and we got better, especially in the outfield group. We didn’t play good defense in the playoffs, but overall it’s a good unit.”
Those changes are already being implemented in the minor leagues, according to Breslow.
“What some of our defensive lapses have done is made us take a look internally around the way we are developing players and our focus on defense in the minor leagues,” said Breslow, adding that the team is changing up some of its methods. “I think we’re going to see the rewards for that.”
Alex Bregman’s future with Red Sox
Bregman has an opt-out built into his contract and is expected to exercise it after the conclusion of the World Series. Breslow didn’t want to get into his contract discussions with the player or his agent, Scott Boras, but used Monday as an opportunity to praise Bregman for his impact on the field and in the clubhouse.
“It’s best to keep those conversations internal. Alex has the right as structured in his contract, and he’s going to do what is best for his family. At the same time, I won’t miss a chance to talk about his contributions to the team, in the field, in the clubhouse,” he said. “His influence has rubbed off on his teammates and by all accounts, he has loved his time in Boston.”