2. Tim Anderson
The White Sox are in a tricky spot with Anderson.
On the one hand, they have a $14 million team option they can pick up for him next season. Before this year, that would've been a no-brainer for the two-time All-Star, but they may decline it now that he's having the worst season of his career (career-low .568 OPS).
If Chicago declines it, Cleveland should make a move for Anderson in free agency, especially since his poor 2023 will lower his price tag. Anderson's only 30 and was an excellent all-around player prior to this season, so he's worth betting on to rebound.
If the White Sox pick up the option, they may still try to trade Anderson next summer before he hits free agency. The Guardians could still make a play for the former batting champion at that time if they need a boost for the stretch run.
Either way, Anderson is a player worth pursuing, as he'd also likely benefit from a change of scenery.