As was mentioned, the early '90s pitching was great; Black Jack, Alex Fernandez, Wilson Alvarez, Jason Bere... ****, how depressing those guys only won one lousy division title.
Late '90s was pretty brutal, though my favorite for no particular reason was Mike Sirotka. I still have a jersey of his. The 2000 Sox had a great ride thanks to some career years from Sirotka, James Baldwin, Jim Parque, and most surprisingly, Cal Eldred. I still have no idea how those guys won 90+ games.
Don Cooper has been in the White Sox organization since 1998 and became the MLB Pitching Coach in 2002 and since then, I think the Sox have had some tremendous talent. The '05 team was spectacular, the only had 6 guys make a start all season long. That is insane. But even then it seems like they've turned a real corner at developing arms. Guys like Quintana and Santiago are real keepers. A decade ago, the Sox were promoting guys like Gary Glover, Josh Stewart, David Sanders, Mike Porzio, and Jon Adkins out of their minor league system. So in that regard, things are better.