Sammy Sosa
Sammy Sosa owning the White Sox would be a bad look for both the White Sox and the Cubs. For the Cubs, they can’t even mend things with him so him coming to the White Sox organization in any way would be bad. They haven’t done much to recognize him in recent years despite him being a great player for them for a long time. Yes, there is a lot of controversy surrounding his playing career but he was a part of the times that saw that be prevalent.
For the White Sox, it would be a bad look too. They traded Sosa to the Cubs after the 1991 season for a return value that wasn’t even worth it. He then went on to, despite the steroid era stuff, have a very nice career for the Cubs. He was an NL MVP, six-time silver slugger, and seven-time all-star. He is probably never going to get into the Hall of Fame despite having borderline Hall of Fame numbers because of the steroid stuff but he helped the Cubs win lots of baseball games and not the White Sox.
If he came to them as their owner one day, that would be tough to look at as fans. He has been the face of a terrible trade made by the White Sox for a long time so keeping him away from the organization at all costs is probably a good idea.