God this is tough...
1) A.J. - Total asshole (nothing wrong with this. i'm an asshole). But he was our asshole. Loved his fire and became a fan for life when he punked that loser Michael Barrett . He represents the attitude I want to see in a White Sox player. Get under the skin of the other team, make them get emotional and screw up, play your ass off, and fire up the fan base.
2) Frank. Guy was my childhood idol and I wanted to be him when I grew up. Such a good person and just an absolute terror at the plate. Legitimately must have been terrifying for pitchers to see him walk up to the plate.
3) Buehrle - Best White Sox pitcher in my lifetime. I honestly feel that he could still be a successful pitcher today, and could have pitched till he was 45
4) Paulie - I mean he's basically Frank lite. Another great guy, who was so consistent for the Sox as a leader and middle of the order presence. I think he was extremely underrated nationally during his time with the Sox
5) Jim Thome - How can you not like a guy who is country strong, eats a ton of hot dogs, and blasts 500ft homers?