Well, Now What?

Alex Bregman is no longer an option.

Fenway Fest was almost a success. After a fun Winter day at Fenway Park (Yes, I was there), my night experienced a quick buzzkill when the tweet from Jeff Passan came across my phone that announced Alex Bregman was signing with the Chicago Cubs. Now, there are so many questions about where this organization is at heading into the 2026 season.

Alex Bregman has signed a 5-year deal with no opt-outs and a full no trade clause. His deal is worth $175M. After an off-season full of questions and waiting with a qualifying offer attached to his name, Alex Bregman now has the security he was looking for.

For this Red Sox team, the Bregman news will be a tough pill to swallow. Bregman was their leader last season. Yesterday Roman Anthony said the following on what he had hoped would happen with Bregman:

“I would love to have him back. I love Breggy. He was a huge part of my success and a lot of the young guys — not only the young guys but many of the guys in the clubhouse. We’re all on the same page as to where we stand with him and what we hope happens… Selfishly, I’d love for him to be hitting behind me for as long as he can. He knows where I stand with that.”

The only narrative in Boston that will be talked about is how the Red Sox chose to create the Rafael Devers debacle by signing Alex Bregman for 1-year. Until the Red Sox go out and add a legitimate bat, if at all, the narrative that the Red Sox signed Bregman to create issues with Devers to eventually get out of the Devers long-term deal will always be there. Maybe the Red Sox never really wanted to commit to Rafael Devers long term but felt forced because they lost Mookie Betts and Xander Bogaerts. Maybe the Red Sox saw an easy out with Alex Bregman.

The answer to all of those “maybes” could easily be, “No” but as of right now, everyone is left making up their own story because ownership and the front office refuse to make a serious addition. And everyone will point to stories like this one from Joon Lee that the Red Sox are cheap.

Everyone will now turn their attention to Bo Bichette. That should be the pivot and some would argue that should have been the move all along anyways. Bichette is four years younger than Bregman. If they offer Bichette a six or seven year deal, they will pay for Bichette’s age 33-34 seasons. According to Red Sox beat reporter Chris Cotillo, the Red Sox were willing to go five years for Bregman, which would have paid Bregman through his age 36. One may say that signing Bichette is just better business based on age.

Right now it’s difficult to imagine the Red Sox signing Bichette. They haven’t made a big splash in free agency since they signed Trevor Story prior to the 2022 season. Also, the reports of the Red Sox wanting to stay under the second luxury tax threshold of $264M are out there and a Bichette signing would put the Red Sox over unless they can find a trade partner for a bigger contract on the roster. With the report of Bo Bichette asking for $300M, a deal with Bichette is going to require the Red Sox to get uncomfortable and go past their projections that they have for a Bichette deal. Frankly, it’s something Craig Breslow has not shown he wants to do or can do.

While it’s easy to jump to conclusions and say, “The Red Sox aren’t going to sign anyone because they are now a cheap organization,” it’s important to wait to see how the chips actually fall before judging. Nothing that the Red Sox have done over the last seven years should give Red Sox fans confidence that Boston will replace the production that Alex Bregman gave them last season. However, there are still options out there that could. And there will be plenty of time to judge if they don’t.

Right now, the 2026 lineup is not as good as the projected lineup was heading into 2025. Last year Alex Bregman was an elite option at third base and Rafael Devers was an elite option at DH. For as much as I’m excited about Marcelo Mayer, there is no comparison if he is the projected third baseman. And a DH of Masataka Yoshida or one of the outfielders doesn’t come close to the bat of Rafael Devers.

The Red Sox should be trying to build on their success from last season where they made the playoffs for the first time since 2021. It’s been four years since the organization has won a playoff series. And the goal for 2026 should be the compete for an AL East title and the AL pennant. Right now, this current Boston roster is not good enough to do either of those things.

President of baseball operations Craig Breslow has some interesting decisions to make. He is staking his entire career with the Red Sox on getting rid of the Devers contract and believing he can build a better team without him. Whether it’s Breslow actually deciding these things or being a puppet for John Henry is irrelevant. Breslow has to get this right or his time in Boston could be over very soon.