Connor Wong
The catcher position for the Red Sox has been a pillow fight to the death in 2023 between Connor Wong and Reese McGuire. Neither player has been particularly awesome this year and while Connor Wong has been the slightly better defensive player between the two this season, he still gets the nod as the catcher that needs to go after the 2023 season.
Wong and McGuire have been weirdly similar this season in terms of production, but McGuire's production came in less than half of the plate appearances after Reese missed a chunk of time due to an oblique injury. Meanwhile, Wong has posted an 83 wRC+ in nearly 300 plate appearances in 2023 and it sure hasn't seemed like he has brought much to the table in terms of game-calling if Boston's pitching this season is any indication. Boston just needs a better catcher and unfortunately for Connor, that means they should probably move on from him.
Alex Verdugo
This is a controversial one because Alex Verdugo's production on the field has not been the problem here whatsoever. Verdugo has slashed .269/.340/.420 in 2023 with a perfectly reasonable 105 wRC+ especially for a guy who has been good defensively in the outfield. Verdugo is heading into his final arbitration season and shouldn't be prohibitively expensive next season. However, there is more going on in Verdugo's case than just the numbers.
Given Verdugo's recent benching and his history of lacking maturity as a professional, it is pretty clear that the relationship between him and the organization isn't at a high point right now. When you combine that with the fact that Boston has outfield help coming from the minor leagues in Ceddanne Rafaela, Boston should strongly consider trading Verdugo this offseason. Even if he isn't an organizational fit for them, he could be a very valuable trade chip that could help them address their pitching woes during the offseason.