Alex Bregman’s one-year stint in Boston was mostly what the Red Sox hoped for-at least until the final stretch. Through mid-August, Bregman was living up to the billing, performing like one of the top players in baseball when healthy.

But over his last 35 games, his production fell off in a noticeable way. The slump dragged his season OPS down to .821 over 114 games.

That’s still solid, no doubt-but when you’re pulling in $40 million a year, “solid” doesn’t quite match the paycheck.

Now the Red Sox find themselves at a bit of a crossroads. They brought Bregman in not just for his stats, but for what he represents-a winning mentality, a veteran presence, a player who’s been through October and knows what it takes to win.

He was a cultural tone-setter and played a key role in trying to reestablish the kind of identity the Red Sox have been chasing. But the question looming large is how far the front office is willing to go to keep that presence in the building.

According to insider reports, if Bregman chooses to opt out-and all signs point in that direction-the Red Sox could hesitate to commit to a long-term deal. A five-year offer, or anything exceeding that, may push them past their comfort zone.

And it makes sense. By the time Bregman reaches the back end of that deal, he’d be 36 or 37, and handing out $35 million-plus per year at that stage of a player’s career requires real conviction-not just in who Bregman is now, but who he’ll be in three, four, or five years.

That’s where ownership comes into the spotlight. Principal owner John Henry will be the one cutting the checks, and his appetite for big baseball spending has been inconsistent in recent seasons. Red Sox fans know he’s been more than willing to open the vault for Liverpool FC, but back in Boston, there’s been a sense of restraint-at least compared to other big-market clubs.

This offseason could change that. Boston doesn’t just have a Bregman decision on its hands.

There’s serious buzz around the team being in play for heavy-hitting free agents like Kyle Schwarber and Pete Alonso-both would fill a glaring power void in a lineup that, notably, didn’t feature a single 30-home run hitter this past season. Those are the kinds of additions that signal a real push to contend.

But circling back to Bregman, it’s worth remembering that it took Boston quite a while to get a deal done with him last offseason. The holdup?

A reluctance to go long-term. So, the question now becomes: Did a year in the clubhouse-and everything Bregman brought on and off the field-change that stance?

Boston has a lot to figure out over the coming months, and how they approach negotiations with Bregman could set the tone for the rest of their offseason. It’s a pivotal moment-one that’ll show whether the Red Sox are serious about spending like a big-market team again, and whether they see Bregman as part of that future, or just a one-year chapter in the club’s ongoing rebuild.

Either way, this winter’s decisions are going to say a lot about the Red Sox, not just in 2026, but well beyond.