The Boston Red Sox have clinched a playoff spot for the first time since 2021, and they'll look to continue their run of postseason dominance against the New York Yankees. Boston hasn't lost a playoff series against its biggest rival since 2003.
It might feel like an odd time to be looking back at last offseason, but on the other hand, the Red Sox are still feeling the (good and bad) effects of their very active winter. Boston’s offseason was positive on the whole, especially when considering that new additions Alex Bregman and Aroldis Chapman have both had All-Star seasons in 2025, with Chapman being particularly dominant.
At the same time, Boston’s front office made some mistakes in the offseason, and a few of them might come back to haunt the Red Sox once the postseason begins.
3 offseason moves the Red Sox might feel the bad consequences of in October
Signing Walker Buehler
Boston released Buehler on August 29, keeping him completely out of the postseason mix (a wise decision), but what if the Red Sox had never brought Buehler on board in the first place? His 7-7 record and 5.45 ERA in 22 starts for Boston amounted to a waste of a signing, especially when you consider the opportunity cost for the Red Sox: by placing faith in Buehler, the Red Sox avoided bringing in a better arm.
Maybe if Buehler never donned a Red Sox uniform, Boston would have been motivated to work Connelly Early into the big league rotation earlier, which, by the looks of it, would have reaped positive rewards for the season. Instead, Buehler’s failures in Boston caused a negative domino effect, forcing the Red Sox to take whatever they could get at the trade deadline in the form of another starter, which ultimately turned into Dustin May (another flop).
All in all, Boston’s rotation feels one ultra-reliable arm short heading into the postseason, and some of that is a result of the failed Buehler experiment.
Not having Roman Anthony in the Opening Day lineup
This qualifies as an offseason decision, as it's pretty clear that Boston concocted a full 2025 plan for Anthony well ahead of Opening Day. Also, this isn’t at all to suggest that Anthony would have avoided injury by starting his season in MLB — that would be a preposterous claim. More so, it’s an acknowledgement that the Red Sox would likely have a much better record right now if Anthony had been in the lineup since day one, which in turn would have resulted in a better playoff seeding.
Boston’s handling of its "Big Three" prospects in 2025 (Anthony, Marcelo Mayer, and Kristian Campbell) still leaves one perplexed. Campbell was the only one of the three on the Opening Day roster, and he’s also the only one who was ultimately sent back down to Triple-A after a rough May and June in the big leagues. Anthony was the last of the three to be called up, despite being by far the most ready to contribute.
Boston’s supposed reasons for delaying Anthony’s call-up have been widely and tirelessly discussed, but a simple truth remains: having Anthony in the Opening Day lineup would have likely led to far more regular-season wins for Boston, which fans might be thinking about during what promises to be an extremely difficult wild-card series (presuming the Red Sox get in).
Failing to retain Kenley Jansen
Obviously, Chapman is Boston’s closer, and no one in baseball would be able to overtake him for that role this season. But from the Red Sox’s perspective, Jansen would be an awesome arm to have right now in the bullpen, especially given the failures of some of the team’s relievers.
Kenley Jansen is the AL Reliever of the Month! Kenley in July:
— SleeperAngels (@SleeperAngels) August 4, 2025
▫️2-0
▫️0.00 ERA
▫️5 saves
▫️13 strikeouts pic.twitter.com/C3xQh6eqPG
Did Boston not push more aggressively to keep Jansen because they were expecting something from Liam Hendriks in 2025? If so, that was a gross miscalculation, as Hendriks didn’t end up being a contributor at all due to poor performance and further injuries.
On the other hand, Jansen has made 60 appearances for the Angels this season, and the four-time All-Star is still evolving. Having Jansen as a setup option for Chapman would be such a comfort for the Red Sox entering the playoffs, and they could have made it happen last winter.