This story was excerpted from Ian Browne’s Red Sox Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.
BOSTON -- After a satisfying but all-too-brief trip back to the postseason, the Red Sox are now looking to take the next step and make sure there are some home playoff games in 2026.
Here are some questions that will need to be answered before that happens.
Will Alex Bregman be back?
At the very least, it was interesting to hear Bregman go just a little past tense following the Wild Card Series elimination game at Yankee Stadium.
“It was an honor to wear this uniform,” Bregman said.
At the same time, Bregman positioned himself as a player who didn’t want to leave the group he became so close to, sitting in full uniform by his locker for nearly an hour after his team was knocked out.
All signs point to Bregman using the first opt-out of the three-year, $120 million contract (much of if deferred) he signed in February. His agency, led by Scott Boras, believes that Bregman will have a more lively market this winter than he did last year without a qualifying offer attached to him.
Given what Bregman has meant to Boston as a leader and mentor, it wouldn’t be surprising if the Sox try to restructure his deal to keep him around a few more years.
“I think it’s best to keep those conversations internal,” said Red Sox chief baseball officer Craig Breslow. “Obviously, Alex has the right, kind of as structured in his contract, to opt out and he's going to do what's best for his family.
“At the same time, I will not miss an opportunity to talk about his contributions on the field, in the clubhouse, to the coaching staff, to the front office. Every conversation we've had, I learned something. I think that impact and influence has rubbed off on his teammates, and by all accounts, he's loved his time in Boston as well.”
The question of whether Bregman stays or not is significant because it will have an impact on how much the Red Sox will allocate to fill other needs this winter.
Can the outfield stay as is?
Before Roman Anthony got injured on Sept. 2, the Sox had a logjam in the outfield. In Anthony, Ceddanne Rafaela, Jarren Duran and Wilyer Abreu, Boston had four everyday-caliber players for three spots. The injury to Marcelo Mayer enabled Cora to play Rafaela at second for a stretch, but that seemed a waste of his defensive prowess. The most logical move would be to package a trade for a premium starting pitcher from a position of strength. Duran holds an $8 million club option, but also has three years of club control left, which could make him an attractive trade target.
Who’s on first?
When Triston Casas finished third in the American League Rookie of the Year Award voting in 2023, he seemed primed to be Boston’s first baseman of the future. But then came a fractured left ribcage injury that kept him out for four months in 24, a sluggish first month-plus of ‘25 followed by a season-ending ruptured left patellar tendon. So where does the club view Casas now? Is he the starting first baseman entering ‘26?
“I don't think it makes a ton of sense on October 6 to say someone is or isn't our first baseman. We'll see how things play out,” said Breslow. “Unfortunately, Triston has missed a significant amount of time over the last two years. We've also seen what he's capable of doing when he’s healthy.”
What is the fit going forward for Kristian Campbell?
There is no case in Red Sox history to compare Campbell to. The club went into Spring Training believing he could be their starting second baseman and quickly signed him to an eight-year, $60 million contract. Campbell rewarded that faith when he was the American League’s Rookie of the Month in April. But he fell on hard times after that, posting a .426 OPS in his subsequent 126 at-bats before going to Triple-A Worcester for the rest of the season. In the Minors, he was deployed here, there and everywhere, starting 31 games at first, 11 games at second, 10 in center, nine at DH, five in left and seven in right.
“Again, stopping short of a role, I think Kristian learned a lot about himself. We learned a lot about him,” said Breslow. “He's a tireless worker. And we saw that from Spring Training through his time in the big leagues when he was the AL Rookie of the Month to when he was struggling and sent down. I’ve got a ton of confidence, both in the work he's going to commit to this offseason and what he's going to mean for this organization. I don't think it makes a ton of sense to try to pin him to a role outside of saying he's going to feel the support of the entire organization. And we know what he’s capable of.”
What will the starting rotation look like by Spring Training?
The hope is that the Sox take some pressure off Garrett Crochet by acquiring a No. 2 starter. If not, a No. 3 would still help. Brayan Bello is definitely back. Lucas Giolito went into the offseason with some irritation in his right elbow and shares a mutual option with the club, so his status is uncertain. Kutter Crawford should return to the mix after missing all of ‘24 with a knee injury and then a right wrist injury he suffered while doing some maintenance in his home. Richard Fitts and Hunter Dobbins will go into the offseason trying to get healthy. Expect Breslow to be aggressive in his pursuit of more help in the rotation.