5. Tyler Glasnow
Adding a starter like Tyler Glasnow would help their rotation get better.
The Chicago White Sox don't really need another right-handed pitcher since signing Mike Clevinger but they would certainly make room if they can add a guy like Tyler Glasnow who is one of the best pitchers in the league. Seeing a guy like this come to the south side would be truly special.
Glasnow missed the second half of 2021 and most of 2022 recovering from Tommy John surgery but he is a guy that is capable of winning a Cy Young Award. If he came and teamed up with Dylan Cease and Michael Kopech, the White Sox would have a great front of the rotation.
The Rays may or may not trade him but leaning towards them moving him feels right. They always seem to let guys like this go before they get mega contracts. The White Sox do the same thing usually but their window is supposed to be open right now while Glasnow is under control.
If this is a Rays team that is going to make this guy available, the White Sox should look into it because he would make their team so much better right away.
The White Sox are not that fun of a team but making one of these deals would certainly make them fun, at least for a little while. Until one happens, however, it is hard to see them making any moves of significance.