Rumor season is upon us, and plenty have been circulating about the Red Sox and their potential offseason targets. After a very quiet and unsuccessful Winter Meetings and failing to sign Pete Alonso, the Red Sox are back at square one. The four biggest names that have been called out in rumors, either by trade or free agency, are Cole Ragans, Ketel Marte, Alex Bregman, and Bo Bichette. As for Bichette and Bregman, those two are free agents, and the Red Sox are willing to make do with one of them.
With time rapidly slipping away on the top remaining infield bats, however, the Red Sox need to do something soon. They're one of the last two teams that haven't made a single major-league signing. After all that talk before the meetings? That's laughable.
After being punched in the gut by Pete Alonso, the other pursuits haven't seemed promising, and Boston appears reluctant to commit fully to any of them. Alex Bregman, for one, was originally viewed as the best fit for Boston after they signed him last year to a three-year deal worth $120 million. The only reason he received less money is that it was February at the time, and he wasn't on a major league team yet. Fittingly enough, he fell into Boston's lap. But now, not so much.
He was seemingly aiming for five years, and the Red Sox are only willing to go for three. But then, Jeff Passan on ESPN reported that Bregman is seeking a six-year agreement as part of his next contract. This decreases his chances of a reunion in Boston by a mile.
Recent rumblings have also suggested that the Arizona Diamondbacks are seriously pursuing Bregman. In fact, they've "possibly" offered Bregman six years, according to Underdog's Jared Carrabis. Ken Kendrick has been willing to open his wallet if his team has a chance to win. That would be a move that would have ripple effects across the market, at least where Boston is concerned. Ken Rosenthal from The Athletic reported that there is a scenario where Arizona can keep Marte if they sign Bregman. If that happens, it would quietly remove two more from Boston's "interested" players list. This would also back Craig Breslow into a corner. That corner leads directly to Bo Bichette.
"Please, Bo, take me with you," Breslow, (probably).
Unlike Bregman, Bichette is not a finished product defensively, but he offers consistency, and that's something Boston has been lacking. Perhaps more importantly, Bichette has reportedly shown a willingness to move off shortstop and play second base full-time. That would help Boston clearly align its infield with Marcelo Mayer and their long-term plans. That flexibility matters, especially for a front office obsessed with optionality.
Still, the larger issue looms. The Red Sox do not believe in long-term deals. Whether it's philosophical restraint or ownership's fear of bad contracts, Boston has consistently stopped short of the aggressive commitments required to land top-tier free agents. That hesitation has already cost them Alonso, and it may soon cost them Bregman as well.
If Breslow waits too long, Bichette could follow a similar path, and suddenly, the Red Sox will be left with trying to sell patience instead of actually proving progression. At some point, choosing flexibility over conviction begins looking the same as standing still.
The Red Sox don't need both Bregman and Bichette due to roster construction. They absolutely need one, though, and it is time the front office started to act like it.