3 roster issues Red Sox have to fix in offseason after 2025 trade deadline neglect

The Boston Red Sox brass talked a big game leading into the 2025 trade deadline. After dealing Rafael Devers in a shocking June shakeup, the Sox looked poised to extend Alex Bregman and perhaps even dive headfirst into the trading pool. With a 10-game winning streak heading into the All-Star break, unanticipated extra cash, and a weak American League, it looked like the stars might have aligned for a Boston team that hasn’t made the postseason since 2021.  

But it apparently wasn’t to be. While Toronto, Seattle, New York, and others got better, Boston remained static. This means the Red Sox will experience more strenuous opposition in their postseason pursuit, and require a bit of extra retooling in the offseason, regardless of how playoff baseball shakes out at Fenway. Trade rumors surrounding Jarren Duran ultimately didn't yield action, but he remains a prime candidate to be moved in the offseason to make room for Roman Anthony amidst an outfield logjam. This and three other areas will have to be big points of focus for Craig Breslow before the spring.

3 roster issues Red Sox have to fix in offseason after 2025 trade deadline neglect

The pitching rotation

Behind Garrett Crochet, there’s little in the way of scary mound presence in Boston's rotation. The trade deadline was filled with rumors of quality pitching help coming to Fenway, including names like Minnesota’s Joe Ryan and Sandy Alcantara of the Marlins. Rental options for the remainder of 2025 like Merrill Kelly, who was dealt by the Diamondbacks and Zac Gallen (who wasn’t moved) will be available in free agency at the season's end.

Nabbing Crochet and then promptly extending him has turned into a massive victory, making Boston significantly better. The Red Sox will need a similar level of aggression this winter to continue improving a pitching squad that has shown flashes of dominance but plenty of weakness over the past few seasons.

Infield depth, and specifically first base

It doesn’t look like Triston Casas will be suiting up again soon for the Sox. His 2025 season came to an end in May, and at least the first few months of the 2026 effort will be played without his services. Casas profiles as a power hitter who can potentially deliver upwards of 40 home runs over a full season. His defense is good, if sometimes “inconsistent,” but the 25-year-old has frequently been named a potential cornerstone of Boston’s future.

An odd approach, to be sure, but Anthony Rizzo is still sitting at home. The soon-to-be 36-year-old was vocal about his opposition to a league minimum contract this year, worrying it would devalue the market for others. This was ahead of an offseason in which a new collective bargaining agreement would be negotiated. After that hurdle passes and a year spent on the shelf has augmented Rizzo’s storied resume, a short-term arrangement might work out for both parties. Going another direction, Pete Alonso will almost certainly opt out of his contract to explore free agency again. Alonso would be a huge swing, but one that might yield significant offensive upside and proven durability at a position that’s long plagued the Sox.

Fixing the black hole at first will shore up the rest of the infield, too. Minor league prospects like Vaughn Grissom, Jhostynxon Garcia, and even Kristian Campbell will have the significant burden of learning a new position lifted off their shoulders. It will make for a better team on the whole.

The bullpen

It feels like a copout to say that the bullpen needs improvement. Every team has issues to iron out here — even a team like Boston, owners of the third best bullpen ERA in baseball. Bullpen support was one of Breslow’s stated goals at this year’s trade deadline, and adding a single rented arm to bolster this group really only scratches the surface. With Aroldis Chapman on a one year deal (and heading toward his 38th birthday), much more action will be necessary to secure long term success in closing out games. Seranthony Dominguez may be available this coming offseason, alongside Devin Williams, Jordan Romano, and the indomitable Kenley Jansen.