Boston should have traded Adam Duvall at the trade deadline
Anyone who followed the trade deadline knows that the market for position players was particularly shallow this year. There were a number of contenders that really needed bats that could actually hit for some power and those guys just were not available this go-around. If the Red Sox would have actually made Adam Duvall available, they would have had a number of teams bidding for his services.
In fairness to the Boston front office, one factor that could have gone into the decision to not trade Duvall is that he did not want to be traded yet again at the trade deadline. While his status as a guy with big offensive upside on a very affordable one year deal made him attractive as a trade candidate, there is a chance that moving him against his wishes could make other such players hesitant to sign short term deals with Boston in the future. However, that should have been just a minor consideration at best and with the current composition of Boston's outfield and Ceddanne Rafaela lurking in Triple-A, Duvall is a guy that needed to be moved (preferably for a pitching prospect).
James Paxton should have been dealt by the Red Sox before the deadline
James Paxton's name seems to come up at every trade deadline regardless of where he is playing. When he is healthy, he is a very productive pitcher who shows flashes of brilliance. However, Paxton does seem to be snakebit when it comes to injuries as he missed the 2022 season after having Tommy John surgery and he was far from being a stranger to the injured list before that.
While Paxton has been one of the few bright spots for the Red Sox pitching staff this season, the reality is that he will be an unrestricted free agent after the season and is making just $4 million in 2023. Even with his injury history, he could have garnered a package of prospects for Boston on par with what some of the better rotation rentals got at the deadline. Instead, Boston held on to Paxton and are likely to miss the playoffs with the prospect of getting nothing when Paxton walks after the season on the horizon.