The Boston Red Sox have put themselves in quite a tough spot this offseason. After watching Alex Bregman sign a five-year, $175 million contract with the Chicago Cubs in free agency, the Red Sox are at serious risk of losing all the positive momentum they generated in 2025.
Boston hasn’t exactly stood pat this offseason, as it’s swung trades for Sonny Gray, Johan Oviedo and Willson Contreras. The problem is that in free agency, the team has yet to sign a single player to a major-league contract.
With teams across the league making notable upgrades, the Red Sox appear to be treading water, which may be a generous description in the wake of Bregman’s departure. If you ask MLB insider Jeff Passan of ESPN, he doesn’t believe the Sox are dead just yet, but he thinks they need a big move in order to keep up with the rest of the American League East.
“Getting Bichette, who’s the obvious choice with Bregman gone and Ketel Marte off the trade market, would provide a huge boost,” Passan wrote. “There are other pivots to make — Nico Hoerner, Brendan Donovan or Isaac Paredes, with the right-handed bats more appealing — but ultimately all that matters is: Do they have enough talent?
There are far worse places to start than with Garrett Crochet and Roman Anthony, but the answer, compared to their peers, is: No.”
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Options still exist for the Red Sox when it comes to shoring up its roster. Bo Bichette is a prime fit in free agency, but it remains to be seen if the front office will be able to do enough to bring him to town. The trade market is flush with targets, although that could require the team to give up some of its top prospects.
The Red Sox need to get uncomfortable, which is a tough pill to swallow, as the offseason did not need to play out like this. There’s still time to right the ship, but the longer the Sox wait, the bigger the hole they have dug themselves into will become.
Featured image via Kamil Krzaczynski/Imagn Images
