There Are Two Moves The Red Sox Must Make As They Reset For The 2026 Season
The Red Sox held their season-ending press conference Monday morning. It was a mostly dull affair, which is the norm when Craig Breslow opens his mouth. Holy moly. If you're having trouble sleeping, go watch Monday's media availability.
Anyway, it took 12 minutes into the almost 45-minute press conference to get to a question about Alex Bregman. They could have spent the entire time talking about the third baseman, because he's one of the two biggest priorities for the team as they try to reset for another playoff run in 2026.
Yes, it's that simple - Breslow and Co. must do these two things in the offseason.
1. Bring Back Bregman.
So, he's going to opt out - from MLB.com
"Bregman can opt out of the final two years and $80 million -- $40 million of which is deferred -- of the three-year, $120 million deal he signed with the Red Sox last February. According to a source, it’s a near certainty that Bregman will opt out and test free agency for a second straight year, this time without a qualifying offer attached to him.
Bregman’s annual average salary of $40 million, even with the deferrals, puts him in elite company, though he’ll be entering his age-32 season in 2026, giving him incentive to find a deal that takes him past ‘27.
“I struggle to see him sustaining that level of AAV [annual average value],” an American League executive said. “But the total guarantee should be well north of $80 million.”
The Sox have to find a way to retain him. A 2025 All-Star, Bregman made an immediate impact on the team. Yes, a right quad injury cost him 43 games and clearly affected his bat. But the 2024 Gold Glove winner played Gold Glove-level defense for the Red Sox.
He made plays like this look easy all summer. Beyond the baseball impact, Bregman clearly had a mentoring and coaching impact on these young teammates.
Many on the Sox roster went out of their way to credit Bregman for helping them this season. From calling the catcher at 2 AM to talk pitchers to helping guys fix their swings - I don't think it's an overstatement to call him the most important guy in the Sox clubhouse not named Alex Cora.
What kind of message would it send to the fans if, after you traded away Rafael Devers in an effort to save money, you just let Bregman opt out and sign somewhere else? I'll answer that question - a shitty one.
Like, this one is simple - you have to bring him back. No excuses.
2. Go find a legit No. 2 pitcher.
The Red Sox had three days in Minnesota to work on a trade for the Twins' Joe Ryan at the deadline, and reports had Breslow waiting until the last minute to get a deal done. If that's the way it went down, then shame on Breslow.
He has a chance to make things right in the offseason.
Ryan is the obvious fit behind Garrett Crochet in the Sox rotation. Just 29 years old, the right-hander was a 2025 All-Star who was Top 10 in the American League in ERA, SO/9, WHIP, and WAR - he's really good. The fact that you talked to the Twins about him at the deadline should put you in a good position to know what it would take to get him.
Jarren Duran, Payton Tolle, plus prospects? Do it.
Jarren Duran, Connelly Early, plus prospects? Yeah, that would be more painful. But you'd have to seriously consider it.
Manager Alex Cora expressed his excitement about the team's pitching during Monday's press conference. That's fine, but in the group of Brayan Bello, Early, Tanner Houck…there's no No. 2 starter there. Maybe down the road, but not now.
I guess Logan Webb is a possibility. Paul Skenes seems like a pipedream. There will be other names that come up, but the team needs to find the guy behind Crochet in the rotation.
Then there's first base. There's figuring out what happens with Trevor Story and Kristian Campbell. We'll see what happens with Cora's coaching staff; those things are all down the To-Do List.
Breslow, Cora, and Sam Kennedy all agreed on Monday that the team didn't accomplish what it wanted to in 2025 and that they can't be complacent this offseason.
If that's the case, then it's simple - bring back Bregman, get a No. 2 pitcher, and go from there.