For the Red Sox, the offseason needs to be on point

Truthfully, the term Red Sox offseason is something of an oxymoron. What the offseason truly is, after all, is the beginning of 2026.

So where, exact, do the Red Sox stand entering the latest "most important offseason" in memory? Generally speaking, they're in pretty good shape - though that hardly means things are perfect. The Sox obviously face some big contractual questions with people like Alex Bregman and Trevor Story, among others, and let's not forget that while they qualified for the postseason, they also finished in third place in the American League East. For organization that spent last offseason talking about about the importance of winning division championships, that isn't a real reason to puff out your chest.

So what are the Sox saying now?

“What I have seen as a player and what I’ve seen over the last couple of years is that with this ownership group, when there is a chance to build a winner and a team that can contend for the postseason, resources aren’t a problem," chief baseball officer Craig Breslow told reporters yesterday. "And I think we’ve talked a lot about how this window of contention is upon us.”

Said Kennedy: “What was rewarding to see this year was these two guys, again, to my right (meaning Breslow and manager Alex Cora), acting with urgency. We didn’t get where we wanted to go — we all know that — but we acted with urgency, certainty, and aggression - and plan to continue to do that as we go forward.”

With all due respect to Kennedy and Red Sox ownership, Cora talked about urgency three years ago, but the highest floors at Fenway Park had one foot in and one foot out. What constitutes urgency now is a matter of debate and something suggests that there is still at least some disconnect between how the fans base (and uniformed personnel) defines urgency and how the non-uniformed personnel does.

As always, time will tell how that out shakes out. In the interim, here's an an overview of the Red Sox' roster and ideal needs as the building begins in earnest for the spring of 2026:

You want questions? From first base to third - and everywhere in between - the Red Sox have gray areas. Bregman and Story could opt out. And did you know that the Red Sox failed to have even a single player at either first base or second base with more than 230 plate appearances at the position? If you think that the right side was a revolving door in 2025, just wait if both Bregman and Story try the free-agent market. If that happens, the Red Sox will almost literally be starting from scratch.

Oh, and then there's this: third base was the only position at which the Red Sox received league play that was above average, at least according to fangraphs. As good as Story was, he ranked 18th in WAR among 31 regulars at his position. (Bregman was seventh.) Does that he mean he stunk? No. And both you and the Red Sox should certainly want him back. But if he's hitting anywhere from third to fifth again, the 2026 probably isn't good enough.

In the end, there's a great deal unsettled here. Certainly, Marcelo Mayer fits in somewhere. At first base, the Sox sound rather cool on Triston Casas. (That really shouldn't be a surprise.) Kristian Campbell couldn't play second base this year and the experiment at first base in the minors sounds like it went poorly. So if you're one of those people who thinks the Sox would be better off if Bregman and Story departed, make certain you know all the options before you decide.

The infield is a bit of a cluster at the moment, folks. Keep an eye on it.

As a team, overall, the position was a push for Red Sox management in 2025. The emergence of Carlos Narvaez certainly gave the Sox an option - especially early - but he faded in the second half and Connor Wong was borderline useless. (Narvaez had nine passed balls, tied for second in the league, and all but cornered the market on catcher's interference.) Still, the Sox have bigger problems going forward, though they would ideally replace Wong with a left-handed-hitting backup who could give Narvaez a break against select right-handers. That market is thin, to say the least.

If you're looking for a positional area of "strength," this is probably it. Using WAR as a standard, Jarren Duran (fourth of 34), Ceddanne Rafaela (sixth of 28) and Wilyer Abreu (13th of 32) all ranked in the top half of players, respectively at left, center and right fields. Roman Anthony will obviously fill one of those positions, and we're not going to waste much time here talking about him. Anthony is a lock who will be a lineup centerpiece for years to come. The only question is whom the Sox put around him to make it all fit.

If the Sox want to make a deal, this is the clear area to trade from, especially when you add Campbell into the mix. (It should be noted that Campbell has particular value to the Sox in this mix because he projects as the best right-handed hitter.) Rafaela is the best defender and only true center fielder. That means that Duran or Abreu could (and should?) be used as trade bait if the opportunity allows. At the trading deadline, the Sox resisted from dealing either in discussions for Minnesota Twins right-handed pitcher Joe Ryan.

How the Red Sox handle this mix should tell us plenty about their level of "urgency" for 2026. All of the players involved are either relatively inexpensive and/or signed for the long term. The point? If the Sox put the emphasis on the contracts rather the players and skill sets, they'll keep them all. And that would be a bad sign.

Simple truth: Garrett Crochet was the difference in 2025. Including postseason, the Red Sox went 90-75 in 165 games, exactly 15 games over .500. They were 24-9 when Crochet pitched, exactly 15 games over .500. Get the picture? The so-so Sox of 2022-2024 were still the So... So... Sox of 2025 when Crochet wasn't pitching. Obviously, some of the younger players on the club should continue to improve. But even all-time Sox aces Roger Clemens and Pedro Martinez couldn't win championships without support.

As for the rest of the rotation, it's in pretty good shape. Lucas Giolito is almost certainly gone, but Brayan Bello, Payton Tolle and Connelly Early are all under team control (via contract or CBA rules) for the foreseeable future. What we don't know is whether any can be a true No. 2 to Crochet the way that someone like Joe Ryan (signed through 2027) could. Presumably, the Sox and Twins will revisit discussions this offseason. The Sox would be smart to get more serious about someone like Ryan sooner rather than later.

One other thing: as we've seen in the playoffs, the New York Yankees (Cam Schlittler) and Toronto Blue Jays (Trey Yesavage) have young arms that have wowed this postseason and both already have better rotations than Boston. Both also finished ahead of the Red Sox in the standings. If you don't get better here, you're falling behind further.

Believe it or not, analytically speaking, this was the highest-performing part of the Red Sox in 2025. Among 147 qualifying relievers in all of baseball this year, Aroldis Chapman ranked second and Garrett Whitlock ranked third in WAR. The return of Justin Slaten at the end of the year further solidified the Sox in the late innings, which is part of the reason Cora stretched his bullpen and probably asked too much of Whitlock at year's end.

The worrisome part: with all due respect to Chapman, who was otherworldly, he isn't likely to repeat the best year of his career at 38 years old. (If he does, then you're that much further ahead.) Slaten gives the Sox a fallback, but the Sox would be wise to build in some depth and contingencies. Overall this year, Sox relievers ranked a collective second in the majors in WAR and ERA. That's obviously excellent. If they can stay in the top 6 (20 percent), that's a big win.

Look, I like Romy Gonzalez and Rob Refsnyder as much as anyone - as long as they're bench and platoon players. I might even be able to live with Masataka Yoshida as a left-handed bat off the bench, though the Sox should absolutely try to find a taker if someone wants to absorb the remaining two years and $37.2 million of his contract. Nick Sogard feels like the most valuable member of the group that includes Nate Eaton and David Hamilton - and we've already mentioned the need for a better backup catcher. Overall, some version of this existing group is a perfectly fine way to start the season. If the Sox can save a few bucks here, fine. But they shouldn't skimp.

One point: you can always find bench pieces as the season develops.