2. Tim Anderson
The Chicago White Sox very well could trade Tim Anderson this winter.
Tim Anderson has an option this off-season so the Chicago White Sox have a decision to make. They could choose not to take it and let him walk in free agency. They could, however, pick it up and then trade him so that they don't lose him for nothing.
There might be a lot of teams that will only trade him if he agrees to be a second baseman. That is on Tim Anderson to decide as he may not want to make that move. He may be forced to though based on his play over the last year.
For a long time, Tim Anderson was the face of the franchise. That literally went up until this season too so it is one of the farthest falls from grace we've ever seen on the south side. Off-the-field things have played into this but he also went from being an elite hitter to a bad hitter in just a few months.
If a team is willing to take the chance on Anderson, the White Sox should do it. They should pick up his option anyway because there is a chance that he will build his value back up in 2024 so teams are more likely to want him at the trade deadline. White Sox fans wish things were different but 2023 was that eye-opening.