The Red Sox entered this offseason with big talk and bigger expectations. But as the calendar inches toward the holidays, Boston remains one of only two teams in the majors yet to make a major-league signing. That’s not just surprising-it’s concerning for a club that promised to be aggressive and now finds itself watching key targets slip away.
After striking out on Pete Alonso, who was arguably their top priority, the Sox are back at square one. And the names still in play-Cole Ragans, Ketel Marte, Alex Bregman, and Bo Bichette-represent drastically different paths forward.
Two are trade candidates. Two are free agents.
But at this point, Boston can’t afford to be picky. They need to land one.
Let’s start with Alex Bregman. For a while, he looked like the cleanest fit.
Boston had reportedly signed him last year to a three-year, $120 million deal-though that came late in the offseason, when Bregman was still on the outside looking in and the market had cooled. This time, it’s different.
Bregman’s camp is reportedly eyeing a six-year deal, according to ESPN’s Jeff Passan, and that’s a big jump from what the Red Sox are comfortable offering. Boston’s front office has been firm about sticking to a three-year window, and that gap is growing harder to bridge.
To make matters more complicated, the Arizona Diamondbacks are now in the mix. Reports suggest they’ve “possibly” offered Bregman the six-year deal he’s seeking.
Ken Kendrick, Arizona’s owner, has shown a willingness to spend when he thinks the team is close-and this could be one of those moments. If Bregman ends up in the desert, it could trigger a domino effect.
According to Ken Rosenthal, there’s a scenario where the D-backs could retain Ketel Marte if they land Bregman. That would effectively wipe two of Boston’s rumored targets off the board in one move.
Which brings us to Bo Bichette.
Bichette doesn’t have Bregman’s glove, but he brings something Boston badly needs: consistency. He’s a proven bat and, perhaps more importantly, he’s reportedly open to moving off shortstop to play second base full-time.
That’s a big deal for a team trying to build around top prospect Marcelo Mayer at short. Bichette’s flexibility would give Boston clarity in the infield and align with their long-term vision-something this front office values deeply.
But once again, the issue isn’t fit. It’s philosophy.
The Red Sox have shown a clear reluctance to hand out long-term deals. Whether that’s coming from the front office or ownership’s fear of getting burned by a bad contract, the result is the same: Boston keeps falling just short in the bidding wars for top-tier talent.
They were hesitant with Alonso. They’re hesitant with Bregman.
And if they wait too long, Bichette could be next.
At some point, the pursuit of “optionality” starts to look like indecision. And in a competitive market, indecision is the fastest way to get left behind.
Boston doesn’t need both Bregman and Bichette. But they absolutely need one of them.
The roster has holes, the fan base is restless, and the AL East isn’t getting any easier. The Red Sox have the resources.
They’ve cleared the payroll space. Now they need to show conviction.
Because if they don’t act soon, they won’t just be selling flexibility-they’ll be selling fans on patience. Again.