The Boston Red Sox are entering a critical offseason, intending to take serious steps to reclaim their relevance. However, the shadow of one franchise-defining misstep—the trade of Mookie Betts—remains huge, threatening to undermine trust in their vision. Four years after trading Betts to the Dodgers, the notion of organizational incompetence continues to weigh heavily on every decision and raises the stakes for new executives.
In February 2020, the Red Sox sent Betts, arguably the most complete player in baseball, and David Price to Los Angeles in a salary-shedding deal that still draws ire. The return—Alex Verdugo, Jeter Downs, and Connor Wong—was underwhelming, especially given Betts’ subsequent dominance. He helped the Dodgers win a World Series that year and has remained an MVP-caliber player, cementing the trade as a cautionary tale of shortsightedness and financial priorities trumping competitiveness. For Red Sox fans, it became emblematic of an ownership group more interested in balancing the books than building dynasties.
Buster Olney recently posted on X, “Boston is aggressive with dollars now, but the Red Sox will have to pay extra to overcome a negative player perception that really started growing when the team wouldn’t pay Mookie Betts.”
This winter, the pressure to remove the stigma has been at its highest ever. The new Chief Baseball Officer, Craig Breslow, has the responsibility of rebuilding a team that does not have an ace pitcher, a reliable bullpen, and the stars that are synonymous with the Boston team.
Some of the names that speculations suggested include Corbin Burnes, Blake Snell, and Juan Soto, but the fan base is slowly losing patience. Many fear this will be another offseason of unfulfilled promises, echoing last year’s puzzling decision to invest in Masataka Yoshida while neglecting an abysmal pitching staff. The lingering mistrust stemming from the Betts trade adds a unique urgency.
Each move this offseason will be scrutinized against the backdrop of 2020. The question isn’t just whether Breslow can build a competitive roster—it’s whether ownership will finally demonstrate the ambition fans demand. For Breslow, the Betts saga serves as both a cautionary tale and a rallying cry.
The Red Sox must prove that they’ve learned from their past mistakes by committing fully to high-impact signings and trades. Anything less than transformative offseason risks leaving the organization adrift in the unforgiving AL East, where rivals like the Yankees and Rays have shown no such hesitations.
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